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$385,000

JUST INSIDE THE T-DOCK! An easy access premium 63 x 23.5 ft. slip, with a unique configuration; it has a pier extension, a 9 ft wide finger pier, and the extended portion is a concrete floating dock providing alternate boarding options. The slip is located on the north side of the pier. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village that includes restaurants, shopping - close to Publix, CVS, and other specialty shops - recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Yacht Club members have access to private Yacht Club facility which includes private clubhouse with TV, conference table, comfortable furnishings just for relaxing. Exterior amenities include private pool, grills, outside tables, chase lounges, and convenient bathhouse. Other amenities include dining at the Key Club's unique restaurants, Islandside & Harbourside golf courses, tennis courts and beach facilities, Fitness Centre, Mind and Motion Studio, and Spa. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association before entering the marina. A current photo must be submitted. Max length of vessel allowed is 58 LOA, usable beam is 19 ft at the head of the slip.

A4706843 MLS

JUST INSIDE THE T-DOCK! An easy access premium 63 x 23.5 ft. slip, with a unique configuration; it has a pier extension, a 9 ft wide finger pier, and the extended portion is a concrete floating dock providing alternate boarding options. The slip is located on the north side of the pier. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village that includes restaurants, shopping - close to Publix, CVS, and other specialty shops - recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Yacht Club members have access to private Yacht Club facility which includes private clubhouse with TV, conference table, comfortable furnishings just for relaxing. Exterior amenities include private pool, grills, outside tables, chase lounges, and convenient bathhouse. Other amenities include dining at the Key Club's unique restaurants, Islandside & Harbourside golf courses, tennis courts and beach facilities, Fitness Centre, Mind and Motion Studio, and Spa. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association before entering the marina. A current photo must be submitted. Max length of vessel allowed is 58 LOA, usable beam is 19 ft at the head of the slip.

2800 Harbourside Drive Unit E-21, Longboat Key

$670,000

Welcome to Paradise! Fall in love with this turnkey furnished two- bedroom two bath End Unit condo! Relax and enjoy beautiful unobstructed views of Sarasota Bay from nearly every room in the house. The bright newly remodeled open concept kitchen has new cabinetry, quartz countertops and a large breakfast bar. You can even catch a sunset from the oversized westerly kitchen window. On the far side of the home is the master suite with an ensuite bath with a walk-in shower and dual sink vanity. The walk-in closet has built-in shelves and is large enough to accommodate the one-year-old stackable washer and dryer. The second bedroom has built in closets and drawers along with a built-in desk making it ideal for guests or a home office. Both bedrooms access the lanai that has an amazing view with its floor to ceiling windows. Additional features in the home include a whole house water filter, hurricane impact windows 2023, HVAC 2021, water heater 2022,microwave and range 2023 and a brand-new refrigerator. This home is extremely spacious and provides ample storage. There are two linen closets, three walk in closets and three sets of custom boudoir built-ins. There is also a ground level private storage room at your assigned under building parking space which happens to be located next to the Elevator. This condo is also located directly across from one of the community pools. Enjoy three beach access points (including one private), 26 acres of tropical surroundings including a 1/2 mile of nature trails, two heated pools, fitness center and sauna, clubhouse, tennis and pickleball courts, boat docks (waitlist) kayak launches, kayak storage and two marinas. You are also just minutes away from championship golf courses, restaurants, shopping, St. Armands Circle, Downtown Sarasota, and Anna Marie Island. This waterfront condo community and its great location has something for everyone to enjoy!

2 Beds ⋅ 2 Baths ⋅ TB8550356 MLS ⋅ E Building BLDG.

Welcome to Paradise! Fall in love with this turnkey furnished two- bedroom two bath End Unit condo! Relax and enjoy beautiful unobstructed views of Sarasota Bay from nearly every room in the house. The bright newly remodeled open concept kitchen has new cabinetry, quartz countertops and a large breakfast bar. You can even catch a sunset from the oversized westerly kitchen window. On the far side of the home is the master suite with an ensuite bath with a walk-in shower and dual sink vanity. The walk-in closet has built-in shelves and is large enough to accommodate the one-year-old stackable washer and dryer. The second bedroom has built in closets and drawers along with a built-in desk making it ideal for guests or a home office. Both bedrooms access the lanai that has an amazing view with its floor to ceiling windows. Additional features in the home include a whole house water filter, hurricane impact windows 2023, HVAC 2021, water heater 2022,microwave and range 2023 and a brand-new refrigerator. This home is extremely spacious and provides ample storage. There are two linen closets, three walk in closets and three sets of custom boudoir built-ins. There is also a ground level private storage room at your assigned under building parking space which happens to be located next to the Elevator. This condo is also located directly across from one of the community pools. Enjoy three beach access points (including one private), 26 acres of tropical surroundings including a 1/2 mile of nature trails, two heated pools, fitness center and sauna, clubhouse, tennis and pickleball courts, boat docks (waitlist) kayak launches, kayak storage and two marinas. You are also just minutes away from championship golf courses, restaurants, shopping, St. Armands Circle, Downtown Sarasota, and Anna Marie Island. This waterfront condo community and its great location has something for everyone to enjoy!

4600 Gulf Of Mexico Drive Unit 301, Longboat Key

$495,000

This is it! a condo right on the beach and Gulf! Wake up in the morning, open the drapes, and there it is! Then, after a full day on the Key, sit back and watch a glorious sunset from your private balcony! This condo has been lovingly updated throughout, with everything you need to enjoy a weekend or the winter; when you're not using it, you may have the condo leased by onsite management, and enjoy an income year round- the best of both worlds! The pool and deck are a few steps away, and beach chairs are available to take right out to the water's edge. The Seahorse is in an ideal location on Longboat, with a Publix grocery, pickleball, tennis, boat rentals all about five minutes away. Go restaurant exploring on the Key-The Drydock, Chart House, Mar Vista, Shore and many others about 5 minutes away. Thinking about a round of golf? public golf courses are just 12 miles away. At the Seahorse Beach Resort, you have found your beach getaway, where you'll be warmly greeted.

1 Baths ⋅ A4706240 MLS ⋅ Seahorse Beach Resort BLDG.

This is it! a condo right on the beach and Gulf! Wake up in the morning, open the drapes, and there it is! Then, after a full day on the Key, sit back and watch a glorious sunset from your private balcony! This condo has been lovingly updated throughout, with everything you need to enjoy a weekend or the winter; when you're not using it, you may have the condo leased by onsite management, and enjoy an income year round- the best of both worlds! The pool and deck are a few steps away, and beach chairs are available to take right out to the water's edge. The Seahorse is in an ideal location on Longboat, with a Publix grocery, pickleball, tennis, boat rentals all about five minutes away. Go restaurant exploring on the Key-The Drydock, Chart House, Mar Vista, Shore and many others about 5 minutes away. Thinking about a round of golf? public golf courses are just 12 miles away. At the Seahorse Beach Resort, you have found your beach getaway, where you'll be warmly greeted.

3453 Gulf Of Mexico Drive Unit 237, Longboat Key

$699,000

Enjoy direct Sarasota Bay views and deeded private beach access from this updated fourth-floor residence in Fairway Bay, an established gated Bay Isles community within the Longboat Key Club setting. Residence #442 at 2020 Harbourside Drive offers 1,312 square feet of bright, airy living space with two bedrooms and two bathrooms—an inviting coastal retreat where the bay becomes part of everyday life. Floor-to-ceiling views from the kitchen, dining area, and living room create a memorable backdrop for daily living and entertaining, while the private balcony is an ideal place to begin the day with a Sarasota Bay sunrise or settle in for the evening as the sky changes over the water. Keep watch for passing boats, coastal birds, and the occasional manatee in the bay below. The residence has been thoughtfully updated with a kitchen featuring granite countertops, a granite breakfast bar, stainless-steel appliances, and a newer microwave. A front-loading LG washer and dryer are included for everyday convenience. Ceramic tile flooring extends throughout the main living areas and guest spaces, while the primary bedroom features warm wood flooring. Fairway Bay offers a resort-inspired waterfront lifestyle with scenic walking paths, a heated swimming pool and spa, fitness facilities, social spaces, tennis courts, and paddle sports. Beyond the bayfront setting, owners enjoy deeded access to the Bay Isles Beach Club, providing a private connection to Longboat Key’s renowned Gulf beaches. It is the best of both waterfront worlds: tranquil Sarasota Bay just outside your door and the Gulf of Mexico’s white-sand shoreline close by. The community’s central island location makes it easy to walk or bike to nearby conveniences, including grocery shopping, pharmacy services, and tennis. For those who wish to expand their recreational options, membership opportunities may be available through the nearby Longboat Key Club, with its golf, tennis, dining, fitness, spa, and full-service deep-water marina amenities. St. Armands Circle is moments away for boutique shopping and acclaimed dining, while downtown Sarasota offers a vibrant extension of the island lifestyle with arts, culture, restaurants, and waterfront attractions. This is a rare opportunity to enjoy a beautifully updated fourth-floor bayfront residence where views, private beach access, resort-style amenities, and the effortless rhythm of Longboat Key living come together.

2 Beds ⋅ 2 Baths ⋅ A4705717 MLS ⋅ M-4 BLDG.

Enjoy direct Sarasota Bay views and deeded private beach access from this updated fourth-floor residence in Fairway Bay, an established gated Bay Isles community within the Longboat Key Club setting. Residence #442 at 2020 Harbourside Drive offers 1,312 square feet of bright, airy living space with two bedrooms and two bathrooms—an inviting coastal retreat where the bay becomes part of everyday life. Floor-to-ceiling views from the kitchen, dining area, and living room create a memorable backdrop for daily living and entertaining, while the private balcony is an ideal place to begin the day with a Sarasota Bay sunrise or settle in for the evening as the sky changes over the water. Keep watch for passing boats, coastal birds, and the occasional manatee in the bay below. The residence has been thoughtfully updated with a kitchen featuring granite countertops, a granite breakfast bar, stainless-steel appliances, and a newer microwave. A front-loading LG washer and dryer are included for everyday convenience. Ceramic tile flooring extends throughout the main living areas and guest spaces, while the primary bedroom features warm wood flooring. Fairway Bay offers a resort-inspired waterfront lifestyle with scenic walking paths, a heated swimming pool and spa, fitness facilities, social spaces, tennis courts, and paddle sports. Beyond the bayfront setting, owners enjoy deeded access to the Bay Isles Beach Club, providing a private connection to Longboat Key’s renowned Gulf beaches. It is the best of both waterfront worlds: tranquil Sarasota Bay just outside your door and the Gulf of Mexico’s white-sand shoreline close by. The community’s central island location makes it easy to walk or bike to nearby conveniences, including grocery shopping, pharmacy services, and tennis. For those who wish to expand their recreational options, membership opportunities may be available through the nearby Longboat Key Club, with its golf, tennis, dining, fitness, spa, and full-service deep-water marina amenities. St. Armands Circle is moments away for boutique shopping and acclaimed dining, while downtown Sarasota offers a vibrant extension of the island lifestyle with arts, culture, restaurants, and waterfront attractions. This is a rare opportunity to enjoy a beautifully updated fourth-floor bayfront residence where views, private beach access, resort-style amenities, and the effortless rhythm of Longboat Key living come together.

2020 Harbourside Drive Unit 442, Longboat Key

$399,000

Pre-Construction. To be built. Welcome to PARADISE!!! Award winning beaches/sunsets on the Gulf side and a beautiful bay on the other. Sunrise to sunset this location can only make you smile. Beautifully located 55+ Community. Own the land you live on in Longboat Key. Enjoy the huge community heated pool and recently remodeled dockside clubhouse next to your brand new, 2026, elevated 6 feet up, 2-bedroom, 2 bath, open floorplan home. Bring your boat as you are only footsteps away from your own private marina. If you prefer the beach, go the opposite direction. You don't even have to worry about a chair. Twin Shores Beach and Marina have their own deeded entrance with brand new future Tiki Hut and complimentary chairs to watch the sunset. All of this is located in the middle of Historic Longboat Key. Down the street, Bayfront Park has pickle ball, tennis, basketball, playground, swings, picnic pavilions, big dog and little dog fenced parks with new turf, walking paths, kayak launch/storage and bathrooms. Go south and find your grocery and liquor store, banks, pharmacy and newly added large outdoor pavilion with bathrooms. Wonderful restaurants, shopping, golf, and fishing make island living incredible. See you soon!!! Hurry, Paradise Awaits!

2 Beds ⋅ 2 Baths ⋅ A4706247 MLS

Pre-Construction. To be built. Welcome to PARADISE!!! Award winning beaches/sunsets on the Gulf side and a beautiful bay on the other. Sunrise to sunset this location can only make you smile. Beautifully located 55+ Community. Own the land you live on in Longboat Key. Enjoy the huge community heated pool and recently remodeled dockside clubhouse next to your brand new, 2026, elevated 6 feet up, 2-bedroom, 2 bath, open floorplan home. Bring your boat as you are only footsteps away from your own private marina. If you prefer the beach, go the opposite direction. You don't even have to worry about a chair. Twin Shores Beach and Marina have their own deeded entrance with brand new future Tiki Hut and complimentary chairs to watch the sunset. All of this is located in the middle of Historic Longboat Key. Down the street, Bayfront Park has pickle ball, tennis, basketball, playground, swings, picnic pavilions, big dog and little dog fenced parks with new turf, walking paths, kayak launch/storage and bathrooms. Go south and find your grocery and liquor store, banks, pharmacy and newly added large outdoor pavilion with bathrooms. Wonderful restaurants, shopping, golf, and fishing make island living incredible. See you soon!!! Hurry, Paradise Awaits!

96 Twin Shores Boulevard, Longboat Key

$2,398,000

Ideally situated at the north end of Longboat Key within the confines of The Preserve of Longbeach rests this stunning modern coastal residence. The tastemaker’s tastemaker who owns this masterpiece has imbued it with a seamless design incorporating an open floorplan where the great room, dining area and kitchen reflect a rare integration of all living space. An immediately accessible covered loggia terrace further expands these spaces, but also belies an astounding outdoor arena that houses a pool, lush landscaping and yet another covered sitting area. The first floor primary suite spaciously allows for King size bedding, a sitting area, access to the aforementioned terrace, and a striking en suite w/soaking tub. A forth bedroom or Den is adjacent to a half bath and full sized utility room. Both upstairs bedrooms come w/en suites and capacious closets. 3 of the 4 bedrooms have direct balcony and/or terrace access. The great room features a fireplace which serves as a focal point of earthiness and ease. Bathed in timeless paint treatments, heirloom modern lighting and fixtures the appointments lend for a spectacular dwelling. Exquisite flooring, custom cabinetry, stone counters and Viking appliances resonate a profoundly less but more aesthetic. A 3 car garage allows for easy maneuverability. A whole house elevator maximizes usage for all. Ideal as a family home, secondary Gulf Coastal residence, part-time rental or whatever your family’s dynamic demands. This very particular stretch of sand, surf and sky offers accessibility to a myriad of dining venues, as charming & kitschy as you’d like, or more refined, boat ramp access and recreational opportunities at your leisure. We await your visit, and anticipate your future legacy within the heart that is this home..

4 Beds ⋅ 4 Baths ⋅ TB8547173 MLS

Ideally situated at the north end of Longboat Key within the confines of The Preserve of Longbeach rests this stunning modern coastal residence. The tastemaker’s tastemaker who owns this masterpiece has imbued it with a seamless design incorporating an open floorplan where the great room, dining area and kitchen reflect a rare integration of all living space. An immediately accessible covered loggia terrace further expands these spaces, but also belies an astounding outdoor arena that houses a pool, lush landscaping and yet another covered sitting area. The first floor primary suite spaciously allows for King size bedding, a sitting area, access to the aforementioned terrace, and a striking en suite w/soaking tub. A forth bedroom or Den is adjacent to a half bath and full sized utility room. Both upstairs bedrooms come w/en suites and capacious closets. 3 of the 4 bedrooms have direct balcony and/or terrace access. The great room features a fireplace which serves as a focal point of earthiness and ease. Bathed in timeless paint treatments, heirloom modern lighting and fixtures the appointments lend for a spectacular dwelling. Exquisite flooring, custom cabinetry, stone counters and Viking appliances resonate a profoundly less but more aesthetic. A 3 car garage allows for easy maneuverability. A whole house elevator maximizes usage for all. Ideal as a family home, secondary Gulf Coastal residence, part-time rental or whatever your family’s dynamic demands. This very particular stretch of sand, surf and sky offers accessibility to a myriad of dining venues, as charming & kitschy as you’d like, or more refined, boat ramp access and recreational opportunities at your leisure. We await your visit, and anticipate your future legacy within the heart that is this home..

6840 Longboat Drive S, Longboat Key

$289,000

A 58 ft. x 20 ft. Boat Slip at Longboat Key Moorings Marina. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and discreet, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Yacht Club members have access to private Yacht Club facility which includes private clubhouse with TV, conference table, comfortable furnishings just for relaxing. Exterior amenities include private pool, grills, outside tables, chase lounges, and convenient bathhouse. Other amenities include dining at the Key Club's unique restaurants, Islandside and Harbourside golf courses, tennis courts and beach facilities, Fitness Centre, Mind and Motion Studio, and Spa. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association. Max length of vessel allowed is 53 LOA, usable beam is 18 ft at the head of the slip. A current photo of the vessel must be provided, and the vessel approved by the Association before entering the marina.

A4705272 MLS

A 58 ft. x 20 ft. Boat Slip at Longboat Key Moorings Marina. This is a Yacht Club slip; purchase of the slip requires purchase of membership in the Longboat Key Club. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and discreet, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Yacht Club members have access to private Yacht Club facility which includes private clubhouse with TV, conference table, comfortable furnishings just for relaxing. Exterior amenities include private pool, grills, outside tables, chase lounges, and convenient bathhouse. Other amenities include dining at the Key Club's unique restaurants, Islandside and Harbourside golf courses, tennis courts and beach facilities, Fitness Centre, Mind and Motion Studio, and Spa. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association. Max length of vessel allowed is 53 LOA, usable beam is 18 ft at the head of the slip. A current photo of the vessel must be provided, and the vessel approved by the Association before entering the marina.

2800 Harbourside Drive Drive Unit M-10, Longboat Key

$3,999,990

Exceptional waterfront living meets serious Longboat Key boating in this beautifully updated 4300 sf residence in Country Club Shores. Expansive water views, flexible living spaces and deeded beach access create a home designed for the Florida lifestyle. From the moment you enter, the water takes center stage and you know you're home. Generous living and dining spaces give the interior a sophisticated yet relaxed coastal feel. Inside, enjoy the high ceilings, Italian tile floors and a fireplace - and be transported through the wall of windows to blue waters of your pool and dock. The beautifully appointed kitchen is designed for both entertaining and everyday living with Sub-Zero French-door refrigeration and Wolf double ovens and cooktop, Asko dishwasher, new quartz countertops and a floating island with seating. Separate dining areas provide plenty of room for everything from casual mornings to entertaining a crowd. The primary suite offers a private retreat with a balcony and long-range water views - complete with a spacious bath featuring dual sinks and a walk-in shower. Additional oversized suites both upstairs and downstairs offer flexibility for a study or gym. Even more unique is the home's ability to accommodate extended family and guests. A separate entrance opens to its own living area and full bath, while upstairs are two additional bedrooms, a full bath and private sauna—creating a wonderfully versatile space for guests, multigenerational living or extended stays. Outside is where this property truly distinguishes itself. A generous pavered waterfront deck surrounds the Pebble-finish pool and spa, creating multiple areas for lounging, dining and entertaining. The fenced backyard leads to an impressive boating setup with two boat lifts—approximately 24,000 lbs. and 20,000 lbs.— newer seawall and composite dock plus a fish-cleaning station - making it exceptionally well equipped for the boating enthusiast. You're only four homes from the open waters of Sarasota Bay - providing immediate water access and minutes to the open Gulf. And if beach is more your style - enjoy the neighborhood's deeded access to the Gulf of Mexico- right across the street! Significant improvements add another level of value and peace of mind - including a newer roof (2020), all impact windows and doors, updated seawall and dock infrastructure (including plumbing and electrical service to the dock), extensive paver patio, pool resurfacing, interior and exterior painting, tankless hot water heater, landscaping and gas service ready to go for the next owner. And there's room for the toys with a two-car garage with workshop area and storage. You're only five minutes to vibrant St. Armand's Circle for shopping and dining - and a short drive to downtown Sarasota's cultural and entertainment venues. A special home to enjoy everything that makes Longboat Key living so special.

5 Beds ⋅ 5 Baths ⋅ A4702902 MLS

Exceptional waterfront living meets serious Longboat Key boating in this beautifully updated 4300 sf residence in Country Club Shores. Expansive water views, flexible living spaces and deeded beach access create a home designed for the Florida lifestyle. From the moment you enter, the water takes center stage and you know you're home. Generous living and dining spaces give the interior a sophisticated yet relaxed coastal feel. Inside, enjoy the high ceilings, Italian tile floors and a fireplace - and be transported through the wall of windows to blue waters of your pool and dock. The beautifully appointed kitchen is designed for both entertaining and everyday living with Sub-Zero French-door refrigeration and Wolf double ovens and cooktop, Asko dishwasher, new quartz countertops and a floating island with seating. Separate dining areas provide plenty of room for everything from casual mornings to entertaining a crowd. The primary suite offers a private retreat with a balcony and long-range water views - complete with a spacious bath featuring dual sinks and a walk-in shower. Additional oversized suites both upstairs and downstairs offer flexibility for a study or gym. Even more unique is the home's ability to accommodate extended family and guests. A separate entrance opens to its own living area and full bath, while upstairs are two additional bedrooms, a full bath and private sauna—creating a wonderfully versatile space for guests, multigenerational living or extended stays. Outside is where this property truly distinguishes itself. A generous pavered waterfront deck surrounds the Pebble-finish pool and spa, creating multiple areas for lounging, dining and entertaining. The fenced backyard leads to an impressive boating setup with two boat lifts—approximately 24,000 lbs. and 20,000 lbs.— newer seawall and composite dock plus a fish-cleaning station - making it exceptionally well equipped for the boating enthusiast. You're only four homes from the open waters of Sarasota Bay - providing immediate water access and minutes to the open Gulf. And if beach is more your style - enjoy the neighborhood's deeded access to the Gulf of Mexico- right across the street! Significant improvements add another level of value and peace of mind - including a newer roof (2020), all impact windows and doors, updated seawall and dock infrastructure (including plumbing and electrical service to the dock), extensive paver patio, pool resurfacing, interior and exterior painting, tankless hot water heater, landscaping and gas service ready to go for the next owner. And there's room for the toys with a two-car garage with workshop area and storage. You're only five minutes to vibrant St. Armand's Circle for shopping and dining - and a short drive to downtown Sarasota's cultural and entertainment venues. A special home to enjoy everything that makes Longboat Key living so special.

560 Chipping Lane, Longboat Key

$399,000

Gulf views! Just bring your flip flops and bathing suit to this move-in ready 2br/2ba condo on the 2nd floor in Beach Harbor Club. This beautifully maintained Gulf-to-bay community offers boat slips on the bay and private beach access on the Gulf side, as well as pool, clubhouse, gym and private beach access just across the street! This unit has been tastefully updated to include an all-new bright open kitchen with custom cabinetry, stone counters and high-end appliances, including a Fisher & Paykel fridge, a two-drawer Cafe dishwasher, and a Cafe two-oven, six-burner stove. Flooring throughout was replaced with a light blond luxury vinyl plank. Both baths had updates including cabinetry and same quartz countertops found in the kitchen. The AC was replaced in 2024. This home also has a sweet view of the Gulf from the outdoor seating area in the front. The monthly fee includes water, trash, internet, cable, and pest control, as well as the usual insurances, and exterior maintenances. Beach Harbor Club is an active and amenities-rich community with boat docks, a pool, a gym, private beach access, kayak storage, a ground-level storage closet for beach gear, a beautiful clubhouse and just upstairs from this unit is a wonderful rooftop deck for sunset viewing. No effort required to start living your beach life dream today!

2 Beds ⋅ 2 Baths ⋅ A4704650 MLS ⋅ 3802 BLDG.

Gulf views! Just bring your flip flops and bathing suit to this move-in ready 2br/2ba condo on the 2nd floor in Beach Harbor Club. This beautifully maintained Gulf-to-bay community offers boat slips on the bay and private beach access on the Gulf side, as well as pool, clubhouse, gym and private beach access just across the street! This unit has been tastefully updated to include an all-new bright open kitchen with custom cabinetry, stone counters and high-end appliances, including a Fisher & Paykel fridge, a two-drawer Cafe dishwasher, and a Cafe two-oven, six-burner stove. Flooring throughout was replaced with a light blond luxury vinyl plank. Both baths had updates including cabinetry and same quartz countertops found in the kitchen. The AC was replaced in 2024. This home also has a sweet view of the Gulf from the outdoor seating area in the front. The monthly fee includes water, trash, internet, cable, and pest control, as well as the usual insurances, and exterior maintenances. Beach Harbor Club is an active and amenities-rich community with boat docks, a pool, a gym, private beach access, kayak storage, a ground-level storage closet for beach gear, a beautiful clubhouse and just upstairs from this unit is a wonderful rooftop deck for sunset viewing. No effort required to start living your beach life dream today!

3802 Gulf Of Mexico Drive Unit A203, Longboat Key

$2,675,000

Freshly updated and directly overlooking Sarasota Bay, this four-bedroom waterfront residence in guard-gated Corey’s Landing returns to the market with significant interior enhancements just completed. Most notably, beautiful brand-new oversized porcelain tile flooring now extends throughout the main living areas, creating a fresh, sophisticated look while visually connecting the home’s open living spaces. The fireplace wall has also been thoughtfully scaled back, opening the sightlines and creating a more effortless flow between the living room, dining room and eat-in kitchen. These new improvements complement an exceptional Longboat Key lifestyle centered around the water. Located behind the gates of Bay Isles, the more than 3,100-square-foot residence combines direct Sarasota Bay frontage, updated dock with 14,000-lb boat lift and deeded access to the private Bay Isles Beach Club on the Gulf of Mexico—a particularly desirable combination for those seeking both boating and beach access. The newly updated main level is designed to draw your attention toward the bay. The oversized porcelain tile provides a clean, cohesive foundation throughout the common areas, while soaring ceilings, abundant natural light and walls of glass enhance the home's open, airy feel. The dramatic bayfront living room features cathedral ceilings, a gas fireplace and impact-rated sliding glass doors opening to the screened waterfront terrace, where wide water views create a beautiful backdrop for morning coffee, entertaining and evenings overlooking Sarasota Bay. The primary suite is conveniently located on the first floor, offering a spacious walk-in closet plus two additional closets and a private en-suite bath. Two additional guest bedrooms on this level—one currently used as a study—share a beautifully updated full bathroom. Upstairs, guests enjoy a private retreat with a loft-style bonus area featuring a built-in entertainment center and an oversized en-suite bedroom finished with elegant tilework. Extensive upgrades enhance comfort and long-term value, including a new tile roof (2023), two A/C systems (2022), remodeled kitchen and baths, recessed lighting, storm windows on the bayside, a new electrical panel, exterior lighting, updated landscaping, sprinkler system, and a new screen enclosure. Corey’s Landing offers a maintenance-free waterfront lifestyle with 24-hour guard-gated security, community tennis courts, and a heated pool and spa. Ownership also includes deeded access to the private Bay Isles Beach Club, where residents enjoy Gulf-front relaxation with pavilion seating, beachside gatherings, and direct access to the white sands of Longboat Key. Ideally positioned behind the gates of Bay Isles, this residence is moments from the Longboat Key Club’s championship golf and tennis facilities, nearby marinas, and island dining. St. Armands Circle, Lido Beach, and downtown Sarasota’s renowned cultural venues, galleries, waterfront parks, and restaurants are all within easy reach—bringing together boating, beach access, and the best of Sarasota’s coastal lifestyle.

4 Beds ⋅ 4 Baths ⋅ A4704713 MLS

Freshly updated and directly overlooking Sarasota Bay, this four-bedroom waterfront residence in guard-gated Corey’s Landing returns to the market with significant interior enhancements just completed. Most notably, beautiful brand-new oversized porcelain tile flooring now extends throughout the main living areas, creating a fresh, sophisticated look while visually connecting the home’s open living spaces. The fireplace wall has also been thoughtfully scaled back, opening the sightlines and creating a more effortless flow between the living room, dining room and eat-in kitchen. These new improvements complement an exceptional Longboat Key lifestyle centered around the water. Located behind the gates of Bay Isles, the more than 3,100-square-foot residence combines direct Sarasota Bay frontage, updated dock with 14,000-lb boat lift and deeded access to the private Bay Isles Beach Club on the Gulf of Mexico—a particularly desirable combination for those seeking both boating and beach access. The newly updated main level is designed to draw your attention toward the bay. The oversized porcelain tile provides a clean, cohesive foundation throughout the common areas, while soaring ceilings, abundant natural light and walls of glass enhance the home's open, airy feel. The dramatic bayfront living room features cathedral ceilings, a gas fireplace and impact-rated sliding glass doors opening to the screened waterfront terrace, where wide water views create a beautiful backdrop for morning coffee, entertaining and evenings overlooking Sarasota Bay. The primary suite is conveniently located on the first floor, offering a spacious walk-in closet plus two additional closets and a private en-suite bath. Two additional guest bedrooms on this level—one currently used as a study—share a beautifully updated full bathroom. Upstairs, guests enjoy a private retreat with a loft-style bonus area featuring a built-in entertainment center and an oversized en-suite bedroom finished with elegant tilework. Extensive upgrades enhance comfort and long-term value, including a new tile roof (2023), two A/C systems (2022), remodeled kitchen and baths, recessed lighting, storm windows on the bayside, a new electrical panel, exterior lighting, updated landscaping, sprinkler system, and a new screen enclosure. Corey’s Landing offers a maintenance-free waterfront lifestyle with 24-hour guard-gated security, community tennis courts, and a heated pool and spa. Ownership also includes deeded access to the private Bay Isles Beach Club, where residents enjoy Gulf-front relaxation with pavilion seating, beachside gatherings, and direct access to the white sands of Longboat Key. Ideally positioned behind the gates of Bay Isles, this residence is moments from the Longboat Key Club’s championship golf and tennis facilities, nearby marinas, and island dining. St. Armands Circle, Lido Beach, and downtown Sarasota’s renowned cultural venues, galleries, waterfront parks, and restaurants are all within easy reach—bringing together boating, beach access, and the best of Sarasota’s coastal lifestyle.

3530 Mistletoe Lane, Longboat Key

$799,999

Welcome to your Longboat Key PENTHOUSE, where unobstructed PANORAMIC WATER VIEWS from every room create a breathtaking backdrop from the moment you walk through the door. Recently renovated from top to bottom and offered TURNKEY FURNISHED, this residence is ready to enjoy from day one. The BRAND-NEW KITCHEN showcases quartz countertops, custom cabinetry, and all-new stainless-steel appliances, opening seamlessly to the bright and airy living space. Both bathrooms have been completely updated with modern finishes and quartz countertops, creating a fresh, cohesive feel throughout the home. Other thoughtful updates throughout include luxury vinyl flooring throughout, fresh carpeting in the bedrooms, beautifully remodeled, IMPACT WINDOWS, generous storage, and the convenience of an in-unit washer and dryer. Located in the pet-friendly waterfront community of Windward Bay, residents enjoy an impressive collection of amenities including boat slips, two swimming pools, a fitness center, sauna, tennis and pickleball courts, and three beach access points. NO upcoming special assessments, FULLY FUNDED reserves, and a PASSED Milestone. Perfectly positioned on Longboat Key, this penthouse offers the relaxed island lifestyle while keeping you conveniently connected to the dining, shopping, beaches, and entertainment of Longboat Key, St Armands, and Anna Maria Island. Whether you're searching for a full-time residence or your own Florida getaway, this turnkey waterfront penthouse is ready to welcome you home.

2 Beds ⋅ 2 Baths ⋅ A4704564 MLS ⋅ Windward Bay BLDG.

Welcome to your Longboat Key PENTHOUSE, where unobstructed PANORAMIC WATER VIEWS from every room create a breathtaking backdrop from the moment you walk through the door. Recently renovated from top to bottom and offered TURNKEY FURNISHED, this residence is ready to enjoy from day one. The BRAND-NEW KITCHEN showcases quartz countertops, custom cabinetry, and all-new stainless-steel appliances, opening seamlessly to the bright and airy living space. Both bathrooms have been completely updated with modern finishes and quartz countertops, creating a fresh, cohesive feel throughout the home. Other thoughtful updates throughout include luxury vinyl flooring throughout, fresh carpeting in the bedrooms, beautifully remodeled, IMPACT WINDOWS, generous storage, and the convenience of an in-unit washer and dryer. Located in the pet-friendly waterfront community of Windward Bay, residents enjoy an impressive collection of amenities including boat slips, two swimming pools, a fitness center, sauna, tennis and pickleball courts, and three beach access points. NO upcoming special assessments, FULLY FUNDED reserves, and a PASSED Milestone. Perfectly positioned on Longboat Key, this penthouse offers the relaxed island lifestyle while keeping you conveniently connected to the dining, shopping, beaches, and entertainment of Longboat Key, St Armands, and Anna Maria Island. Whether you're searching for a full-time residence or your own Florida getaway, this turnkey waterfront penthouse is ready to welcome you home.

4800 Gulf Of Mexico Drive Unit PH 3, Longboat Key

$399,000

Have you ever dreamed of living on the water on Longboat Key, with your boat just steps from your back door? Imagine starting your morning with coffee outside in front of your dock and breakfast in the sun-filled breakfast nook overlooking the canal, spending the afternoon boating or kayaking on Sarasota Bay, and ending the day with your toes in the sand along the Gulf. Here, that can simply be your everyday life. Beautifully remodeled two years ago and offered furnished, this 1-bedroom, 1-bath canal-front end unit is ready to enjoy from day one. The bright coastal interior features a renovated kitchen that opens to the living room, an updated bathroom, newer appliances, impact-resistant windows and doors, and beautiful tile flooring throughout. A wall of windows surrounding the breakfast nook draws your eye toward the water and creates the perfect spot to linger over breakfast. At the end of the day, retreat to the spacious bedroom, where a long window brings in plenty of natural light and offers another glimpse toward the water. But the real magic begins outside. Step out to your own waterfront setting with a two-year-old dock just beyond your door, new pavers and a seawall replaced in 2021. Grab one of the included kayaks for a peaceful paddle, cast a line from the dock, or hop aboard your boat and head out to Sarasota Bay and the Intracoastal Waterway. There's even room along the side of the property to store your boat trailer. And on Longboat Key, life on the water is only half the story. When you're ready for the beach, Gulf access is just a short walk away. Joan M. Durante Park is practically next door, offering 32 acres of trails, gardens and gorgeous Sarasota Bay views, while island restaurants, shops, a deli, and bike and kayak rentals are all close to home. Perfectly positioned between Sarasota and Anna Maria Island, you can head south toward St. Armands Circle and downtown Sarasota or north toward the laid-back charm of Anna Maria Island. A newer metal roof and flood insurance included in the HOA fee offer additional peace of mind. Parking is easy with paver parking out front plus your own carport. Whether you're searching for your own island retreat, a waterfront investment, or simply a place where boating, beach days and sunsets become part of your routine, this is your opportunity to experience the Longboat Key lifestyle you've been dreaming about.

1 Beds ⋅ 1 Baths ⋅ A4704345 MLS ⋅ #1 BLDG.

Have you ever dreamed of living on the water on Longboat Key, with your boat just steps from your back door? Imagine starting your morning with coffee outside in front of your dock and breakfast in the sun-filled breakfast nook overlooking the canal, spending the afternoon boating or kayaking on Sarasota Bay, and ending the day with your toes in the sand along the Gulf. Here, that can simply be your everyday life. Beautifully remodeled two years ago and offered furnished, this 1-bedroom, 1-bath canal-front end unit is ready to enjoy from day one. The bright coastal interior features a renovated kitchen that opens to the living room, an updated bathroom, newer appliances, impact-resistant windows and doors, and beautiful tile flooring throughout. A wall of windows surrounding the breakfast nook draws your eye toward the water and creates the perfect spot to linger over breakfast. At the end of the day, retreat to the spacious bedroom, where a long window brings in plenty of natural light and offers another glimpse toward the water. But the real magic begins outside. Step out to your own waterfront setting with a two-year-old dock just beyond your door, new pavers and a seawall replaced in 2021. Grab one of the included kayaks for a peaceful paddle, cast a line from the dock, or hop aboard your boat and head out to Sarasota Bay and the Intracoastal Waterway. There's even room along the side of the property to store your boat trailer. And on Longboat Key, life on the water is only half the story. When you're ready for the beach, Gulf access is just a short walk away. Joan M. Durante Park is practically next door, offering 32 acres of trails, gardens and gorgeous Sarasota Bay views, while island restaurants, shops, a deli, and bike and kayak rentals are all close to home. Perfectly positioned between Sarasota and Anna Maria Island, you can head south toward St. Armands Circle and downtown Sarasota or north toward the laid-back charm of Anna Maria Island. A newer metal roof and flood insurance included in the HOA fee offer additional peace of mind. Parking is easy with paver parking out front plus your own carport. Whether you're searching for your own island retreat, a waterfront investment, or simply a place where boating, beach days and sunsets become part of your routine, this is your opportunity to experience the Longboat Key lifestyle you've been dreaming about.

707 Saint Judes Drive S Unit 1, Longboat Key

$200,000

The middle pier, right in front at Longboat Key Club! I-12, a 45 ft x 21 ft. slip in the marina. Purchase of this slip does require membership in the LBK Club. This is the only north-south pier in the marina; plenty of deep water and cool breezes. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and discreet, on-site maintenance and concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 40 LOA; beam depends on the vessel. Call to discuss.

A4704169 MLS

The middle pier, right in front at Longboat Key Club! I-12, a 45 ft x 21 ft. slip in the marina. Purchase of this slip does require membership in the LBK Club. This is the only north-south pier in the marina; plenty of deep water and cool breezes. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and discreet, on-site maintenance and concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 40 LOA; beam depends on the vessel. Call to discuss.

2600 Harbourside Drive Unit I-12, Longboat Key

$225,000

A much sought after inside-the-T 48 x 23.5 foot slip at Longboat Key Club Moorings! Club membership is not required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina village that includes restaurants, shopping - close to Publix, CVS, and other specialty shops - recreational and social activities, and discreet, on-site maintenance and concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 43 LOA; beam depends on the vessel. Call to discuss!

A4703861 MLS

A much sought after inside-the-T 48 x 23.5 foot slip at Longboat Key Club Moorings! Club membership is not required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina village that includes restaurants, shopping - close to Publix, CVS, and other specialty shops - recreational and social activities, and discreet, on-site maintenance and concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 43 LOA; beam depends on the vessel. Call to discuss!

2600 Harbourside Drive Unit Q-10, Longboat Key

$835,000

Welcome to this beautifully situated 2 or 3 bedroom 2.5-bath villa overlooking the second hole of the Harborside White Egret Golf Course. Designed with an inviting sense of openness, the residence features soaring vaulted ceilings accented by rich wood beams, contemporary lighting, and skylights that fill the interior with abundant natural light. The thoughtfully designed floor plan creates an effortless flow between the living, dining, family, and kitchen areas, making the home equally suited to relaxed everyday living or entertaining. The spacious primary suite is privately positioned toward the rear of the home and offers direct access to the screened lanai. Step outside to enjoy tranquil views of the picturesque waterway, complete with fountains, with the manicured golf course providing a beautiful backdrop. Adjacent to the living and dining areas, a versatile additional room with its own closet and access to the second bath offers flexibility as a den, home office, or third bedroom. Additional features include a two-car garage, central vacuum system, and an updated pool deck surface. Ideally positioned to take advantage of the peaceful golf-course setting, this residence offers an exceptional opportunity to create a home in a desirable Bay Isles community. HUD Case #093-659100. Initial Disposition: IN, Equal Housing Opportunity.

3 Beds ⋅ 3 Baths ⋅ A4703789 MLS

Welcome to this beautifully situated 2 or 3 bedroom 2.5-bath villa overlooking the second hole of the Harborside White Egret Golf Course. Designed with an inviting sense of openness, the residence features soaring vaulted ceilings accented by rich wood beams, contemporary lighting, and skylights that fill the interior with abundant natural light. The thoughtfully designed floor plan creates an effortless flow between the living, dining, family, and kitchen areas, making the home equally suited to relaxed everyday living or entertaining. The spacious primary suite is privately positioned toward the rear of the home and offers direct access to the screened lanai. Step outside to enjoy tranquil views of the picturesque waterway, complete with fountains, with the manicured golf course providing a beautiful backdrop. Adjacent to the living and dining areas, a versatile additional room with its own closet and access to the second bath offers flexibility as a den, home office, or third bedroom. Additional features include a two-car garage, central vacuum system, and an updated pool deck surface. Ideally positioned to take advantage of the peaceful golf-course setting, this residence offers an exceptional opportunity to create a home in a desirable Bay Isles community. HUD Case #093-659100. Initial Disposition: IN, Equal Housing Opportunity.

2321 Harbour Oaks Drive, Longboat Key

$216,000

Super city skyline views along with easy boat access! This 45 x 20 foot slip at Longboat Key Club Moorings is located on the north side of O-dock. Club membership is not required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and on-site concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 40 LOA; beam depends on the vessel. Call for more information.

A4703254 MLS

Super city skyline views along with easy boat access! This 45 x 20 foot slip at Longboat Key Club Moorings is located on the north side of O-dock. Club membership is not required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and on-site concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 40 LOA; beam depends on the vessel. Call for more information.

2600 Harbourside Drive Unit O-07, Longboat Key

$139,000

GET EXCITED ABOUT THIS ONE on Longboat Key! Not just because of the LOCATION, but because of the opportunity to finish making it your own which includes the following (not yet installed) materials: new windows, new flooring, new cabinetry, high-end appliances, ship-lap, as well as the furnishings. AND, you will get to enjoy the NEWLY RENOVATED CLUBHOUSE, which is almost complete. Brand new Tiki Hut coming soon on the beach, as well. Did I mention the extremely affordable HOA fees, which is rare on Longboat Key? Twin Shores is a unique 55+ Gulf-to-Bay community offering access to both the beach and Sarasota Bay. This charming 1-bedroom, 1-bath home (with another full-bath outside) is ready for its next owner to complete the renovation and create their own island retreat. (Also, the owner had plans to install the existing shuttered doors to create an optional temporary 2nd bedroom for overnight guests!) Renovation work has already begun, giving you the opportunity to finish the home to your personal taste and style. This home can be your inviting Longboat Key getaway or full-time island residence. What truly sets this opportunity apart is that Twin Shores has the best of both worlds in this resident-owned Gulf-to-Bay cooperative community, with private deeded Gulf beach access, Sarasota Bay access, marina, community pool and clubhouse. Spend your mornings walking the beach, your afternoons boating or relaxing by the pool, and your evenings enjoying game nights in the clubhouse as well as everything Longboat Key has to offer. Opportunities at this price point on Longboat Key are increasingly hard to find. Offered AS-IS. Renovation is incomplete and the appliances, cabinetry, flooring, and windows at the property are included in the sale. Twin Shores Beach and Marina offers a saltwater/heated community pool, a marina with boat slips available for lease (current waitlist), a beautiful, new clubhouse (almost completed) with plenty of community activities and social events. This community offers an array of outdoor activities because of its beach-to-bay location: Enjoy kayaking, paddle boarding, biking, boating and fishing. Love pickleball? Bayfront Park is a short walk or bike ride away which offers pickleball for all levels. Twin Shores Beach and Marina is a remnant of Old Florida with extremely affordable community fees at $280/month which includes water, sewer, trash, pool maintenance, clubhouse, management, marina, maintenance grounds and common area taxes. Enjoy million-dollar sunrises from the marina and million-dollar sunsets from the deeded beach without the typical Longboat Key million-dollar-plus price tag!

1 Beds ⋅ 1 Baths ⋅ A4702801 MLS

GET EXCITED ABOUT THIS ONE on Longboat Key! Not just because of the LOCATION, but because of the opportunity to finish making it your own which includes the following (not yet installed) materials: new windows, new flooring, new cabinetry, high-end appliances, ship-lap, as well as the furnishings. AND, you will get to enjoy the NEWLY RENOVATED CLUBHOUSE, which is almost complete. Brand new Tiki Hut coming soon on the beach, as well. Did I mention the extremely affordable HOA fees, which is rare on Longboat Key? Twin Shores is a unique 55+ Gulf-to-Bay community offering access to both the beach and Sarasota Bay. This charming 1-bedroom, 1-bath home (with another full-bath outside) is ready for its next owner to complete the renovation and create their own island retreat. (Also, the owner had plans to install the existing shuttered doors to create an optional temporary 2nd bedroom for overnight guests!) Renovation work has already begun, giving you the opportunity to finish the home to your personal taste and style. This home can be your inviting Longboat Key getaway or full-time island residence. What truly sets this opportunity apart is that Twin Shores has the best of both worlds in this resident-owned Gulf-to-Bay cooperative community, with private deeded Gulf beach access, Sarasota Bay access, marina, community pool and clubhouse. Spend your mornings walking the beach, your afternoons boating or relaxing by the pool, and your evenings enjoying game nights in the clubhouse as well as everything Longboat Key has to offer. Opportunities at this price point on Longboat Key are increasingly hard to find. Offered AS-IS. Renovation is incomplete and the appliances, cabinetry, flooring, and windows at the property are included in the sale. Twin Shores Beach and Marina offers a saltwater/heated community pool, a marina with boat slips available for lease (current waitlist), a beautiful, new clubhouse (almost completed) with plenty of community activities and social events. This community offers an array of outdoor activities because of its beach-to-bay location: Enjoy kayaking, paddle boarding, biking, boating and fishing. Love pickleball? Bayfront Park is a short walk or bike ride away which offers pickleball for all levels. Twin Shores Beach and Marina is a remnant of Old Florida with extremely affordable community fees at $280/month which includes water, sewer, trash, pool maintenance, clubhouse, management, marina, maintenance grounds and common area taxes. Enjoy million-dollar sunrises from the marina and million-dollar sunsets from the deeded beach without the typical Longboat Key million-dollar-plus price tag!

36 Twin Shores Boulevard, Longboat Key

$574,900

NEW AND IMPROVED PRICE! There is a certain ease to life on Longboat Key, where mornings can begin with a walk to the beach, afternoons unfold by the pool or on the tennis court, and dinner beside the water is never far from home. Set within Cedars East at Cedars Tennis Resort & Club, this beautifully maintained three-level townhome offers a refined way to experience one of Florida’s most desirable barrier-island lifestyles. Natural light is one of the first things you notice. An abundance of windows fills the home with sunshine, creating a bright, calm, and serene atmosphere that feels perfectly suited to its coastal surroundings. New luxury vinyl plank flooring extends through the entry and main living level, giving the home a fresh, cohesive look, while carpeting along the staircase and throughout the third-floor bedroom level adds warmth and comfort to the private spaces. The second floor brings the kitchen, dining, and living areas together in an easy, welcoming flow designed for relaxed everyday living and effortless entertaining. Just beyond the living room, the screened balcony creates a peaceful outdoor retreat for morning coffee, casual dining, quiet reading, or unwinding at the end of the day. A convenient half bath completes this level. Upstairs, the primary suite offers a private ensuite bath with dual sinks and a comfortable sense of separation from the main living areas. The second bedroom features a walk-in closet and is positioned near the full guest bath and upstairs laundry closet. The washer and dryer are approximately three months old and are included with the home. Thoughtful improvements add both style and confidence, including a roof replaced in 2024, a 2024 HVAC system serviced in April 2026, updated interior paint, refreshed flooring, newer toilets, faucets, light fixtures and vents, and a new garage door. Garage parking adds welcome convenience along with room for bicycles, beach equipment, and additional storage. Life at Cedars Tennis Resort & Club is centered around the outdoors and the relaxed sophistication of Longboat Key. Enjoy tennis and pickleball, spend the afternoon by the heated community pool, stay active in the fitness facilities, or gather for a meal without leaving the neighborhood. Nearby beach access makes Gulf days easy to enjoy, while waterfront restaurants, island cafés, marinas, biking routes, and the natural beauty of Longboat Key are all close at hand. For buyers considering investment potential, the property has a strong short-term rental history and is already heavily booked from December through June 2027, offering the advantage of established demand and reservations already in place. All rentals remain subject to current association rules, approval requirements, and the terms of existing reservations. From fresh seafood and sunset dinners to quiet mornings near the shore, this location places the best of Longboat Key within easy reach. St. Armands Circle, Anna Maria Island, and the cultural attractions of Sarasota are also nearby, allowing you to enjoy the island’s peaceful atmosphere without feeling removed from everything the area has to offer. Whether envisioned as a full-time residence, seasonal retreat, or income-producing coastal getaway, this is an opportunity to enjoy thoughtful updates, abundant natural light, resort-inspired amenities, garage parking, and the unmistakable lifestyle of Longboat Key. ¤ Please see 3D Tour and Video ¤

2 Beds ⋅ 3 Baths ⋅ N6144572 MLS ⋅ 508 BLDG.

NEW AND IMPROVED PRICE! There is a certain ease to life on Longboat Key, where mornings can begin with a walk to the beach, afternoons unfold by the pool or on the tennis court, and dinner beside the water is never far from home. Set within Cedars East at Cedars Tennis Resort & Club, this beautifully maintained three-level townhome offers a refined way to experience one of Florida’s most desirable barrier-island lifestyles. Natural light is one of the first things you notice. An abundance of windows fills the home with sunshine, creating a bright, calm, and serene atmosphere that feels perfectly suited to its coastal surroundings. New luxury vinyl plank flooring extends through the entry and main living level, giving the home a fresh, cohesive look, while carpeting along the staircase and throughout the third-floor bedroom level adds warmth and comfort to the private spaces. The second floor brings the kitchen, dining, and living areas together in an easy, welcoming flow designed for relaxed everyday living and effortless entertaining. Just beyond the living room, the screened balcony creates a peaceful outdoor retreat for morning coffee, casual dining, quiet reading, or unwinding at the end of the day. A convenient half bath completes this level. Upstairs, the primary suite offers a private ensuite bath with dual sinks and a comfortable sense of separation from the main living areas. The second bedroom features a walk-in closet and is positioned near the full guest bath and upstairs laundry closet. The washer and dryer are approximately three months old and are included with the home. Thoughtful improvements add both style and confidence, including a roof replaced in 2024, a 2024 HVAC system serviced in April 2026, updated interior paint, refreshed flooring, newer toilets, faucets, light fixtures and vents, and a new garage door. Garage parking adds welcome convenience along with room for bicycles, beach equipment, and additional storage. Life at Cedars Tennis Resort & Club is centered around the outdoors and the relaxed sophistication of Longboat Key. Enjoy tennis and pickleball, spend the afternoon by the heated community pool, stay active in the fitness facilities, or gather for a meal without leaving the neighborhood. Nearby beach access makes Gulf days easy to enjoy, while waterfront restaurants, island cafés, marinas, biking routes, and the natural beauty of Longboat Key are all close at hand. For buyers considering investment potential, the property has a strong short-term rental history and is already heavily booked from December through June 2027, offering the advantage of established demand and reservations already in place. All rentals remain subject to current association rules, approval requirements, and the terms of existing reservations. From fresh seafood and sunset dinners to quiet mornings near the shore, this location places the best of Longboat Key within easy reach. St. Armands Circle, Anna Maria Island, and the cultural attractions of Sarasota are also nearby, allowing you to enjoy the island’s peaceful atmosphere without feeling removed from everything the area has to offer. Whether envisioned as a full-time residence, seasonal retreat, or income-producing coastal getaway, this is an opportunity to enjoy thoughtful updates, abundant natural light, resort-inspired amenities, garage parking, and the unmistakable lifestyle of Longboat Key. ¤ Please see 3D Tour and Video ¤

508 Forest Way, Longboat Key

$200,000

Nestled in a beautifully protected marina on the exclusive Longboat Key. No Longboat Key Club Membership is Required. This premium 48x20-foot wet slip accommodates vessels up to 43 feet and provides a true vacation lifestyle with full-time live-aboard privileges. Boating enthusiasts will enjoy seamless, unrestricted deep-water access to Sarasota Bay, the Intracoastal Waterway, and the Gulf of Mexico with zero fixed bridges. The slip is fully equipped with robust dual 50-amp and dual 30-amp electrical hookups, while the marina provides comprehensive dockside services including both diesel and gasoline at the fuel dock and complimentary vessel pump-outs by professional dock hands. Owners also enjoy the flexibility to lease the slip to marina-approved vessels. Life at the marina combines everyday convenience with resort-style perks, featuring stunning, unobstructed sunrise and sunset views daily. The property includes water, sewer, cable TV, and Wi-Fi, alongside access to a well-maintained bathhouse, coin laundry facilities, a secure package delivery center, and free bicycle rentals. Parking is highly accessible with multiple spaces located directly next to the dock. Ownership integrates you into the Bay Isles HOA, which ensures peace of mind through 24-hour guarded gates, active security, and immaculate common area maintenance. For just $600 a year, owners can also join the walkable Bay Isles Beach Club to enjoy newly renovated beachfront facilities, volleyball nets, and picnic areas with grills. To complete the luxury experience, a complimentary community shuttle is available to transport you directly to the premier shopping and dining at St. Armand's Circle or the Longboat Key Club Resort properties.

A4701807 MLS

Nestled in a beautifully protected marina on the exclusive Longboat Key. No Longboat Key Club Membership is Required. This premium 48x20-foot wet slip accommodates vessels up to 43 feet and provides a true vacation lifestyle with full-time live-aboard privileges. Boating enthusiasts will enjoy seamless, unrestricted deep-water access to Sarasota Bay, the Intracoastal Waterway, and the Gulf of Mexico with zero fixed bridges. The slip is fully equipped with robust dual 50-amp and dual 30-amp electrical hookups, while the marina provides comprehensive dockside services including both diesel and gasoline at the fuel dock and complimentary vessel pump-outs by professional dock hands. Owners also enjoy the flexibility to lease the slip to marina-approved vessels. Life at the marina combines everyday convenience with resort-style perks, featuring stunning, unobstructed sunrise and sunset views daily. The property includes water, sewer, cable TV, and Wi-Fi, alongside access to a well-maintained bathhouse, coin laundry facilities, a secure package delivery center, and free bicycle rentals. Parking is highly accessible with multiple spaces located directly next to the dock. Ownership integrates you into the Bay Isles HOA, which ensures peace of mind through 24-hour guarded gates, active security, and immaculate common area maintenance. For just $600 a year, owners can also join the walkable Bay Isles Beach Club to enjoy newly renovated beachfront facilities, volleyball nets, and picnic areas with grills. To complete the luxury experience, a complimentary community shuttle is available to transport you directly to the premier shopping and dining at St. Armand's Circle or the Longboat Key Club Resort properties.

2600 Harbourside Drive Unit P-05, Longboat Key

$425,000

Easy access and docking at this 75 ft. x 26 ft. Boat Slip at Longboat Key Moorings Marina on D-dock. Located on the West side of the marina. Ample turning radius between piers, so lots of room to maneuver. Direct access to Sarasota Bay and the ICW; 15 minutes to the Gulf. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village and restaurants, shopping (close to Publix, CVS, and other shops), recreational and social activities, on-site maintenance and concierge services. Each slip includes wifi, water, pump out and metered electric, along with trash pick up and dockhands to assist. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association. A current photo must be submitted. Max length of vessel allowed is 70 LOA, usable beam is 23 ft at the head of the slip. Each vessel must be approved by the Association's Board of Directors prior to entering the marina by submitting a current photo and boat specs.

A4701620 MLS

Easy access and docking at this 75 ft. x 26 ft. Boat Slip at Longboat Key Moorings Marina on D-dock. Located on the West side of the marina. Ample turning radius between piers, so lots of room to maneuver. Direct access to Sarasota Bay and the ICW; 15 minutes to the Gulf. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village and restaurants, shopping (close to Publix, CVS, and other shops), recreational and social activities, on-site maintenance and concierge services. Each slip includes wifi, water, pump out and metered electric, along with trash pick up and dockhands to assist. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association. A current photo must be submitted. Max length of vessel allowed is 70 LOA, usable beam is 23 ft at the head of the slip. Each vessel must be approved by the Association's Board of Directors prior to entering the marina by submitting a current photo and boat specs.

2800 Harbourside Drive Unit D-16, Longboat Key

$6,495,000

This spectacular waterfront pool home was just completed in 2026 and is built with uncompromising craftsmanship and every attention to detail. A West Indies-inspired residence in the coveted neighborhood of Emerald Harbor on Longboat Key, it offers expansive water views from every room of the wide canal and Harris Bayou, granting easy access to the intracoastal waterway and the Gulf of Mexico. Walls of glass open to covered porches with remote screens that allow for easy indoor-outdoor living. Features include an incredible chef's kitchen with high-end appliances and a totally separate prep kitchen; Of the 4 bedrooms, there are two primary suites, and all of them have their own stunning en-suites. Each one has access to a covered balcony and all have those stunning water views; A fire pit, private dock, outdoor shower and pool bath, plus deeded beach access complete the Longboat Key lifestyle. Every luxury amenity expected in a home of this caliber makes this a truly special offering.

4 Beds ⋅ 6 Baths ⋅ A4699408 MLS

This spectacular waterfront pool home was just completed in 2026 and is built with uncompromising craftsmanship and every attention to detail. A West Indies-inspired residence in the coveted neighborhood of Emerald Harbor on Longboat Key, it offers expansive water views from every room of the wide canal and Harris Bayou, granting easy access to the intracoastal waterway and the Gulf of Mexico. Walls of glass open to covered porches with remote screens that allow for easy indoor-outdoor living. Features include an incredible chef's kitchen with high-end appliances and a totally separate prep kitchen; Of the 4 bedrooms, there are two primary suites, and all of them have their own stunning en-suites. Each one has access to a covered balcony and all have those stunning water views; A fire pit, private dock, outdoor shower and pool bath, plus deeded beach access complete the Longboat Key lifestyle. Every luxury amenity expected in a home of this caliber makes this a truly special offering.

711 Old Compass Road, Longboat Key

$850,000

Just reduced priced to sell quickly! Stunning gulf views are the focal point of this raised level 1st floor condo located at the Bayport Beach & Tennis Club, two bedroom, two bath has an additional flex room with a Murphy Bed and built-ins can be used as a third bedroom, newer kitchen with quartz countertops, Updates in the bathrooms with whirlpool tub in guest bedroom. Spacious primary bedroom with built-in drawers and walk-in closet, ceramic tile thru-out with LVP floors in the guest bedroom, 3 new hurricane windows, A/C 2025, hot water heater 2026. Hurricane shutters. There is plenty of outdoor space just out the sliding glass doors is a large patio to set up a grill, dine outside, or just relax and enjoy the beautiful sunset views. Lots of storage space throughout the unit and a storage closet in your covered carport. The beautiful 27 acre tropically landscaped grounds boast both Gulf to Bay access. There is 1200 feet of private pristine beach on the Gulf with chairs, umbrellas and lounge chairs provided for your use, plus a kayak launch and fishing pier on Sarasota Bay. The amenities offered include a Jr. size Olympic pool, Clubhouse, fitness center, four Har-Tru tennis courts and nature trails, New roof and exterior painted in the last few months by the HOA, professional on-site management.

2 Beds ⋅ 2 Baths ⋅ A4701332 MLS ⋅ C BLDG.

Just reduced priced to sell quickly! Stunning gulf views are the focal point of this raised level 1st floor condo located at the Bayport Beach & Tennis Club, two bedroom, two bath has an additional flex room with a Murphy Bed and built-ins can be used as a third bedroom, newer kitchen with quartz countertops, Updates in the bathrooms with whirlpool tub in guest bedroom. Spacious primary bedroom with built-in drawers and walk-in closet, ceramic tile thru-out with LVP floors in the guest bedroom, 3 new hurricane windows, A/C 2025, hot water heater 2026. Hurricane shutters. There is plenty of outdoor space just out the sliding glass doors is a large patio to set up a grill, dine outside, or just relax and enjoy the beautiful sunset views. Lots of storage space throughout the unit and a storage closet in your covered carport. The beautiful 27 acre tropically landscaped grounds boast both Gulf to Bay access. There is 1200 feet of private pristine beach on the Gulf with chairs, umbrellas and lounge chairs provided for your use, plus a kayak launch and fishing pier on Sarasota Bay. The amenities offered include a Jr. size Olympic pool, Clubhouse, fitness center, four Har-Tru tennis courts and nature trails, New roof and exterior painted in the last few months by the HOA, professional on-site management.

713 Bayport Way Unit 713, Longboat Key

$500,000

An easy access slip with the views to along with the superb amenity package, Slip B-16 at Longboat Key Club Moorings Marina provides one of the most desired locations as a Yacht Club Member slip in the Marina. With the slip measuring 85 x 29.5, and a usable beam of 25 feet and a long and extra wide finger pier. This 'inside the T-head' slip location provides close proximity to the Marina Village, Restaurant, and Pool. The Longboat Key Club Moorings Marina is a World Class deep water marina providing direct access to Sarasota Bay and ICW. Yacht Club membership at the Longboat Key Club Moorings provides members access to the private clubhouse, which is well appointed with TV, conference room, private pool area, outside seating and tables, grill, and bathhouse all in a relaxing atmosphere. Additionally, the Longboat Key Club offers multiple restaurants, world class tennis and golf facilities, fitness center, with spa and beach access. The Club also reciprocates with 400 of Clubs throughout the country. The Marina is also located within close proximity to Publix, CVS, and world class shopping at St. Armand's Circle. The longest vessel this slip will accommodate is 80 feet. Beam depends on the vessel type and measure. Vessel must be approved by the Board of Directors prior to entering the Marina. Membership in the Longboat Key Club is required.

A4700188 MLS

An easy access slip with the views to along with the superb amenity package, Slip B-16 at Longboat Key Club Moorings Marina provides one of the most desired locations as a Yacht Club Member slip in the Marina. With the slip measuring 85 x 29.5, and a usable beam of 25 feet and a long and extra wide finger pier. This 'inside the T-head' slip location provides close proximity to the Marina Village, Restaurant, and Pool. The Longboat Key Club Moorings Marina is a World Class deep water marina providing direct access to Sarasota Bay and ICW. Yacht Club membership at the Longboat Key Club Moorings provides members access to the private clubhouse, which is well appointed with TV, conference room, private pool area, outside seating and tables, grill, and bathhouse all in a relaxing atmosphere. Additionally, the Longboat Key Club offers multiple restaurants, world class tennis and golf facilities, fitness center, with spa and beach access. The Club also reciprocates with 400 of Clubs throughout the country. The Marina is also located within close proximity to Publix, CVS, and world class shopping at St. Armand's Circle. The longest vessel this slip will accommodate is 80 feet. Beam depends on the vessel type and measure. Vessel must be approved by the Board of Directors prior to entering the Marina. Membership in the Longboat Key Club is required.

2600 Harbourside Drive Unit B-16, Longboat Key

$425,000

Seeking an opportunity to enjoy the Longboat Key lifestyle? This turnkey, two-bedroom, two-bath residence overlooks the Intracoastal Waterway and offers 1,072 square feet of living space. The view out the back of the condominium is simply magical. Sparkling water, beautiful sunsets, and, of course, manatees. This residence comfortably sleeps six, has direct access to the Harbour walking path, and also includes an in-home washer and dryer. Longboat Harbour offers an extensive collection of resident amenities, including a dedicated parking space, sauna, outdoor pools, putting green, kayak and paddleboard launch with storage, pickleball and tennis courts. Boat docks are available on a first-come, first-served basis for less than $600 annually, subject to availability. Residents also enjoy a recreation center with activities including poker, table tennis, billiards, arts and crafts, woodcarving and grilling areas. A deeded, private beach provides convenient access to the Gulf, along with storage, restrooms and showers. The condominium association has completed new roofing, providing added peace of mind. If you've been waiting for the right way to live, I think you just found it.

2 Beds ⋅ 2 Baths ⋅ A4700306 MLS ⋅ 4390 BLDG.

Seeking an opportunity to enjoy the Longboat Key lifestyle? This turnkey, two-bedroom, two-bath residence overlooks the Intracoastal Waterway and offers 1,072 square feet of living space. The view out the back of the condominium is simply magical. Sparkling water, beautiful sunsets, and, of course, manatees. This residence comfortably sleeps six, has direct access to the Harbour walking path, and also includes an in-home washer and dryer. Longboat Harbour offers an extensive collection of resident amenities, including a dedicated parking space, sauna, outdoor pools, putting green, kayak and paddleboard launch with storage, pickleball and tennis courts. Boat docks are available on a first-come, first-served basis for less than $600 annually, subject to availability. Residents also enjoy a recreation center with activities including poker, table tennis, billiards, arts and crafts, woodcarving and grilling areas. A deeded, private beach provides convenient access to the Gulf, along with storage, restrooms and showers. The condominium association has completed new roofing, providing added peace of mind. If you've been waiting for the right way to live, I think you just found it.

4390 Exeter Drive Unit 107, Longboat Key

$3,995,000

Discover the rare opportunity to create a legacy waterfront estate in the prestigious Harbor Section of Bay Isles, one of Longboat Key's most coveted boating communities. Tucked behind double gated, guard-secured entry, this exceptional 0.41-acre homesite boasts an impressive 135 feet of deep-water frontage, offering effortless access to Sarasota Bay and the Gulf of Mexico. Designed for those who embrace the waterfront lifestyle, the expansive canal frontage provides possibilities for multiple vessels and seamless days on the water. As a Bay Isles resident, you'll also enjoy deeded private access to the Bay Isles Beach Club, where miles of pristine Gulf beaches await. Perfectly positioned directly across from the world-renowned St. Regis Longboat Key Resort, this premier location places luxury amenities at your doorstep while maintaining the privacy and exclusivity of a gated waterfront enclave. Championship golf, marinas, waterfront dining, boutique shopping at St. Armands Circle, and the arts, culture, and fine dining of downtown Sarasota are all just minutes away. Whether you envision a contemporary coastal masterpiece or a timeless waterfront retreat, this remarkable homesite offers the ideal canvas to build the custom residence you've always imagined in one of Southwest Florida's most distinguished waterfront communities. Architectural plans are available upon request, with engineering complete. Capitalize on the extensive development work already completed, saving valuable time and expense while accelerating the path toward permitting and construction. An existing residence is situated on the property; however, the property is being marketed for its exceptional homesite and development potential.

A4698387 MLS

Discover the rare opportunity to create a legacy waterfront estate in the prestigious Harbor Section of Bay Isles, one of Longboat Key's most coveted boating communities. Tucked behind double gated, guard-secured entry, this exceptional 0.41-acre homesite boasts an impressive 135 feet of deep-water frontage, offering effortless access to Sarasota Bay and the Gulf of Mexico. Designed for those who embrace the waterfront lifestyle, the expansive canal frontage provides possibilities for multiple vessels and seamless days on the water. As a Bay Isles resident, you'll also enjoy deeded private access to the Bay Isles Beach Club, where miles of pristine Gulf beaches await. Perfectly positioned directly across from the world-renowned St. Regis Longboat Key Resort, this premier location places luxury amenities at your doorstep while maintaining the privacy and exclusivity of a gated waterfront enclave. Championship golf, marinas, waterfront dining, boutique shopping at St. Armands Circle, and the arts, culture, and fine dining of downtown Sarasota are all just minutes away. Whether you envision a contemporary coastal masterpiece or a timeless waterfront retreat, this remarkable homesite offers the ideal canvas to build the custom residence you've always imagined in one of Southwest Florida's most distinguished waterfront communities. Architectural plans are available upon request, with engineering complete. Capitalize on the extensive development work already completed, saving valuable time and expense while accelerating the path toward permitting and construction. An existing residence is situated on the property; however, the property is being marketed for its exceptional homesite and development potential.

1600 Harbor Sound Drive, Longboat Key

$1,999,000

Discover an exceptional chance to complete a vision of waterfront luxury in the highly sought-after community of Country Club Shores on Longboat Key. This canal-front home offers the rare opportunity to pick up where the current owner left off—finishing a sophisticated coastal residence with the majority of major structural work already completed. For discerning buyers seeking to capture immediate equity and create a bespoke waterfront retreat, this property represents outstanding value in prime Longboat Key real estate. Set on a spacious 110’ x 110’ canal-front lot, the home features a fully reconstructed seawall and a private dock equipped with a 13,000-pound Platinum Series boat lift, providing effortless access to Sarasota Bay and the sparkling Gulf of Mexico. The residence is framed for approximately 3,089 square feet under air, offering 5 bedrooms and 3 bathrooms in an elegant coastal ranch-style layout designed for seamless indoor-outdoor living. Substantial improvements have already been executed to the highest standards: a brand-new roof, complete framing, exterior walls, plumbing and electrical rough-ins, natural gas lines, insulation, HVAC ductwork, and impact-resistant windows and doors. Premium materials and finishes—including custom Italian cabinetry, Miele appliances, designer fixtures, and additional high-end components—convey with the property. Engineer-prepared plans provide a clear roadmap for completion, empowering the next owner to personalize the final touches while benefiting from the extensive work already invested. Located in one of the best positions within the desirable Country Club Shores community, this fixer-upper presents the perfect canvas to realize the seller’s vision of an amazing luxury waterfront home. Imagine waking to serene water views, launching your boat from your private dock, and enjoying the effortless Florida lifestyle that defines Longboat Key. Just moments away, enjoy world-class amenities and recreation: championship golf at the prestigious Longboat Key Club, pristine Gulf beaches for sun-soaked days, and the vibrant dining and shopping scene at St. Armands Circle. Explore Sarasota’s renowned fine and performing arts venues, upscale boutiques, and waterfront restaurants—all while residing in this sought-after enclave. Whether you crave boating adventures, cultural experiences, or relaxed coastal living, this location delivers unparalleled convenience and luxury. Don’t miss this unique opportunity to complete a standout waterfront property and unlock its full potential in one of Florida’s most desirable communities.

5 Beds ⋅ 3 Baths ⋅ A4699685 MLS

Discover an exceptional chance to complete a vision of waterfront luxury in the highly sought-after community of Country Club Shores on Longboat Key. This canal-front home offers the rare opportunity to pick up where the current owner left off—finishing a sophisticated coastal residence with the majority of major structural work already completed. For discerning buyers seeking to capture immediate equity and create a bespoke waterfront retreat, this property represents outstanding value in prime Longboat Key real estate. Set on a spacious 110’ x 110’ canal-front lot, the home features a fully reconstructed seawall and a private dock equipped with a 13,000-pound Platinum Series boat lift, providing effortless access to Sarasota Bay and the sparkling Gulf of Mexico. The residence is framed for approximately 3,089 square feet under air, offering 5 bedrooms and 3 bathrooms in an elegant coastal ranch-style layout designed for seamless indoor-outdoor living. Substantial improvements have already been executed to the highest standards: a brand-new roof, complete framing, exterior walls, plumbing and electrical rough-ins, natural gas lines, insulation, HVAC ductwork, and impact-resistant windows and doors. Premium materials and finishes—including custom Italian cabinetry, Miele appliances, designer fixtures, and additional high-end components—convey with the property. Engineer-prepared plans provide a clear roadmap for completion, empowering the next owner to personalize the final touches while benefiting from the extensive work already invested. Located in one of the best positions within the desirable Country Club Shores community, this fixer-upper presents the perfect canvas to realize the seller’s vision of an amazing luxury waterfront home. Imagine waking to serene water views, launching your boat from your private dock, and enjoying the effortless Florida lifestyle that defines Longboat Key. Just moments away, enjoy world-class amenities and recreation: championship golf at the prestigious Longboat Key Club, pristine Gulf beaches for sun-soaked days, and the vibrant dining and shopping scene at St. Armands Circle. Explore Sarasota’s renowned fine and performing arts venues, upscale boutiques, and waterfront restaurants—all while residing in this sought-after enclave. Whether you crave boating adventures, cultural experiences, or relaxed coastal living, this location delivers unparalleled convenience and luxury. Don’t miss this unique opportunity to complete a standout waterfront property and unlock its full potential in one of Florida’s most desirable communities.

525 Sloop Lane, Longboat Key

$950,000

Move right in and start enjoying the Longboat Key lifestyle! Perfectly positioned behind the gates of highly sought after Bay Isles, this beautifully renovated residence combines elegant updates, low-maintenance living, and one of the area's most desirable resort-style communities. Every major improvement has already been completed, allowing you to simply unpack and begin enjoying paradise. The thoughtfully redesigned kitchen is the heart of the home, featuring all-new appliances, a wine refrigerator, custom all-wood cabinetry with convenient pull-out shelving, and an open design that flows effortlessly into the spacious living and dining areas. New tile flooring extends throughout the kitchen, living room, and primary suite, while new carpet creates warm, inviting guest bedrooms. The impressive list of recent upgrades provides exceptional peace of mind, including a new tile roof with hurricane-rated skylights, hurricane-impact windows and doors, new HVAC system with UV air purification lights, tankless water heater, water softener, new garage door opener, fresh interior paint throughout, and beautiful plantation shutters installed throughout the home. One of the home's most outstanding features is the enormous private screened lanai, creating an exceptional outdoor living space rarely found in this price range. Complete with an awning for covered grilling and tranquil pond views, this oversized outdoor retreat is perfect for morning coffee, afternoon relaxation, entertaining friends, or enjoying Florida's spectacular sunsets. A charming garden patio, accessible from both the guest bedroom and laundry room brings in the Florida sunlight and a place to grow tropical plants or a private herb garden. Ownership in Bay Isles includes exclusive access to the private Bay Isles Beach Club, where residents enjoy deeded Gulf-front beach access complete with gated parking, pavilions, picnic facilities, grills, restrooms, and miles of Longboat Key's world-famous white sand beaches. Flood insurance is conveniently included within the HOA fees, providing additional value and peace of mind. Just minutes away, the Longboat Key Moorings Marina offers deep-water boating accommodations, waterfront dining, and one of the Gulf Coast's premier marinas. Residents also have the opportunity to apply for membership at the renowned Longboat Key Club, featuring championship golf, world-class tennis and pickleball, resort pools, spa facilities, fitness centers, private beach amenities, and exceptional waterfront dining. Beyond the gates, enjoy the sophisticated coastal lifestyle that makes Longboat Key one of Florida's most sought-after destinations. Discover award-winning restaurants, waterfront dining, boutique shopping, art galleries, and charming cafés throughout Longboat Key, while nearby St. Armands Circle and Lido Key offer additional upscale shopping, fine dining, entertainment, and beach experiences just a short drive away. Downtown Sarasota's vibrant arts, theater, and cultural attractions are also conveniently close. Whether you're searching for a year-round residence, seasonal retreat, or luxurious lock-and-leave home, this extensively updated Bay Isles residence offers an exceptional combination of quality, comfort, location, and resort-style amenities that is truly difficult to match.

3 Beds ⋅ 3 Baths ⋅ A4699679 MLS

Move right in and start enjoying the Longboat Key lifestyle! Perfectly positioned behind the gates of highly sought after Bay Isles, this beautifully renovated residence combines elegant updates, low-maintenance living, and one of the area's most desirable resort-style communities. Every major improvement has already been completed, allowing you to simply unpack and begin enjoying paradise. The thoughtfully redesigned kitchen is the heart of the home, featuring all-new appliances, a wine refrigerator, custom all-wood cabinetry with convenient pull-out shelving, and an open design that flows effortlessly into the spacious living and dining areas. New tile flooring extends throughout the kitchen, living room, and primary suite, while new carpet creates warm, inviting guest bedrooms. The impressive list of recent upgrades provides exceptional peace of mind, including a new tile roof with hurricane-rated skylights, hurricane-impact windows and doors, new HVAC system with UV air purification lights, tankless water heater, water softener, new garage door opener, fresh interior paint throughout, and beautiful plantation shutters installed throughout the home. One of the home's most outstanding features is the enormous private screened lanai, creating an exceptional outdoor living space rarely found in this price range. Complete with an awning for covered grilling and tranquil pond views, this oversized outdoor retreat is perfect for morning coffee, afternoon relaxation, entertaining friends, or enjoying Florida's spectacular sunsets. A charming garden patio, accessible from both the guest bedroom and laundry room brings in the Florida sunlight and a place to grow tropical plants or a private herb garden. Ownership in Bay Isles includes exclusive access to the private Bay Isles Beach Club, where residents enjoy deeded Gulf-front beach access complete with gated parking, pavilions, picnic facilities, grills, restrooms, and miles of Longboat Key's world-famous white sand beaches. Flood insurance is conveniently included within the HOA fees, providing additional value and peace of mind. Just minutes away, the Longboat Key Moorings Marina offers deep-water boating accommodations, waterfront dining, and one of the Gulf Coast's premier marinas. Residents also have the opportunity to apply for membership at the renowned Longboat Key Club, featuring championship golf, world-class tennis and pickleball, resort pools, spa facilities, fitness centers, private beach amenities, and exceptional waterfront dining. Beyond the gates, enjoy the sophisticated coastal lifestyle that makes Longboat Key one of Florida's most sought-after destinations. Discover award-winning restaurants, waterfront dining, boutique shopping, art galleries, and charming cafés throughout Longboat Key, while nearby St. Armands Circle and Lido Key offer additional upscale shopping, fine dining, entertainment, and beach experiences just a short drive away. Downtown Sarasota's vibrant arts, theater, and cultural attractions are also conveniently close. Whether you're searching for a year-round residence, seasonal retreat, or luxurious lock-and-leave home, this extensively updated Bay Isles residence offers an exceptional combination of quality, comfort, location, and resort-style amenities that is truly difficult to match.

2350 Harbour Oaks Drive, Longboat Key

$395,000

Pre-Construction. To be built. Welcome to PARADISE!!! Award winning beaches/sunsets on the Gulf side and a beautiful bay on the other. Sunrise to sunset this location can only make you smile. Enjoy the huge community heated pool and recently remodeled dockside clubhouse next to your brand new, 2026, elevated over 6 feet, 2-bedroom, 2 bath, open floorplan home. HURRY and you can help design your new home and deck. Bring your boat as you are only footsteps away from your own private marina. If you prefer the beach, go the opposite direction. You don't even have to worry about a chair. Twin Shores Beach and Marina have their own deeded entrance with brand new Tiki Hut and complimentary chairs to watch the sunset. All of this is located in the middle of Historic Longboat Key. Down the street, Bayfront Park has pickleball, tennis, basketball, playground, swings, picnic pavilions, big dog and little dog fenced parks with new turf, walking paths, kayak launch/storage and bathrooms. Go south and find your grocery and liquor store, banks, pharmacy and newly added large outdoor pavilion with bathrooms. Wonderful restaurants, shopping, golf, and fishing make island living incredible. See you soon!!! RUN, don't walk, paradise awaits! *** Lot #96 is also available and under construction. ***

2 Beds ⋅ 2 Baths ⋅ A4699581 MLS

Pre-Construction. To be built. Welcome to PARADISE!!! Award winning beaches/sunsets on the Gulf side and a beautiful bay on the other. Sunrise to sunset this location can only make you smile. Enjoy the huge community heated pool and recently remodeled dockside clubhouse next to your brand new, 2026, elevated over 6 feet, 2-bedroom, 2 bath, open floorplan home. HURRY and you can help design your new home and deck. Bring your boat as you are only footsteps away from your own private marina. If you prefer the beach, go the opposite direction. You don't even have to worry about a chair. Twin Shores Beach and Marina have their own deeded entrance with brand new Tiki Hut and complimentary chairs to watch the sunset. All of this is located in the middle of Historic Longboat Key. Down the street, Bayfront Park has pickleball, tennis, basketball, playground, swings, picnic pavilions, big dog and little dog fenced parks with new turf, walking paths, kayak launch/storage and bathrooms. Go south and find your grocery and liquor store, banks, pharmacy and newly added large outdoor pavilion with bathrooms. Wonderful restaurants, shopping, golf, and fishing make island living incredible. See you soon!!! RUN, don't walk, paradise awaits! *** Lot #96 is also available and under construction. ***

71 Twin Shores Boulevard, Longboat Key

$4,300,000

Experience timeless coastal luxury in this exceptional custom estate, perfectly positioned in the prestigious Country Club Shores on the sought-after south end of Longboat Key. Constructed by renowned John Cannon Homes, this classical waterfront residence showcases the exceptional craftsmanship, architectural detail, and quality for which the builder is celebrated. Soaring ceilings, elegant millwork, walls of glass, and exquisite finishes create a light-filled home that perfectly frames the surrounding water views while offering nearly 4,400 square feet of beautifully designed living space. Ideally situated just one home from Sarasota Bay, this rare waterfront property captures sweeping bay views while providing the privacy, protection, and peace of mind that come with its prime location and newer construction. Beautifully updated in 2025 by Brista Homes, the residence features four bedrooms, five full baths, a spacious game room, and a generous loft office with breathtaking bay views—an inspiring space for working remotely or simply relaxing while enjoying spectacular sunsets. Multiple indoor and outdoor living areas are thoughtfully designed for effortless entertaining and everyday coastal living. Light-filled interiors blend refined custom details with relaxed elegance. The gourmet kitchen, appointed with newer appliances (2022), opens seamlessly to the living and dining areas, creating an inviting setting for intimate family gatherings or grand-scale entertaining. The luxurious primary suite is a private sanctuary featuring direct pool access, an elegant tray ceiling, and dual custom walk-in closets. Upstairs, guest suites offer en-suite baths and generous closets, providing exceptional privacy and comfort for family and visitors alike. Extensive recent improvements include a new roof (2025), updated windows, new balusters, and thoughtfully selected designer finishes throughout, creating a residence that perfectly balances timeless elegance with today's modern conveniences. Outdoor living is equally extraordinary. Expansive terraces, a sparkling pool, and tranquil waterfront views create the perfect backdrop for the coveted Florida lifestyle. For boating enthusiasts, the deep-water canal frontage features a composite dock, a 12,000-pound boat lift, and a newer seawall, providing immediate access to Sarasota Bay and just minutes to the Gulf of Mexico. Country Club Shores is one of Longboat Key's most prestigious waterfront communities, encompassing 19 picturesque streets with distinctive nautical and golf-inspired names. The homeowners association maintains the beautifully landscaped common areas and hosts a variety of neighborhood social events, fostering an exceptional sense of community. Residents enjoy convenient beach access and an unbeatable location just minutes from the world-class shopping and dining of St. Armands Circle, as well as the acclaimed restaurants, theaters, galleries, and cultural attractions of downtown Sarasota. Offering panoramic water views, exceptional boating, beach access,and an outstanding south Longboat Key location, this is a rare opportunity to own an extraordinary waterfront residence where timeless architecture, modern luxury, and the very best of Florida coastal living come together.

4 Beds ⋅ 5 Baths ⋅ A4699348 MLS

Experience timeless coastal luxury in this exceptional custom estate, perfectly positioned in the prestigious Country Club Shores on the sought-after south end of Longboat Key. Constructed by renowned John Cannon Homes, this classical waterfront residence showcases the exceptional craftsmanship, architectural detail, and quality for which the builder is celebrated. Soaring ceilings, elegant millwork, walls of glass, and exquisite finishes create a light-filled home that perfectly frames the surrounding water views while offering nearly 4,400 square feet of beautifully designed living space. Ideally situated just one home from Sarasota Bay, this rare waterfront property captures sweeping bay views while providing the privacy, protection, and peace of mind that come with its prime location and newer construction. Beautifully updated in 2025 by Brista Homes, the residence features four bedrooms, five full baths, a spacious game room, and a generous loft office with breathtaking bay views—an inspiring space for working remotely or simply relaxing while enjoying spectacular sunsets. Multiple indoor and outdoor living areas are thoughtfully designed for effortless entertaining and everyday coastal living. Light-filled interiors blend refined custom details with relaxed elegance. The gourmet kitchen, appointed with newer appliances (2022), opens seamlessly to the living and dining areas, creating an inviting setting for intimate family gatherings or grand-scale entertaining. The luxurious primary suite is a private sanctuary featuring direct pool access, an elegant tray ceiling, and dual custom walk-in closets. Upstairs, guest suites offer en-suite baths and generous closets, providing exceptional privacy and comfort for family and visitors alike. Extensive recent improvements include a new roof (2025), updated windows, new balusters, and thoughtfully selected designer finishes throughout, creating a residence that perfectly balances timeless elegance with today's modern conveniences. Outdoor living is equally extraordinary. Expansive terraces, a sparkling pool, and tranquil waterfront views create the perfect backdrop for the coveted Florida lifestyle. For boating enthusiasts, the deep-water canal frontage features a composite dock, a 12,000-pound boat lift, and a newer seawall, providing immediate access to Sarasota Bay and just minutes to the Gulf of Mexico. Country Club Shores is one of Longboat Key's most prestigious waterfront communities, encompassing 19 picturesque streets with distinctive nautical and golf-inspired names. The homeowners association maintains the beautifully landscaped common areas and hosts a variety of neighborhood social events, fostering an exceptional sense of community. Residents enjoy convenient beach access and an unbeatable location just minutes from the world-class shopping and dining of St. Armands Circle, as well as the acclaimed restaurants, theaters, galleries, and cultural attractions of downtown Sarasota. Offering panoramic water views, exceptional boating, beach access,and an outstanding south Longboat Key location, this is a rare opportunity to own an extraordinary waterfront residence where timeless architecture, modern luxury, and the very best of Florida coastal living come together.

657 Halyard Lane, Longboat Key

$625,000

Simply magnificent! This beautifully renovated residence offers the perfect blend of sophisticated design, comfort, and effortless coastal living. Thoughtfully updated with designer finishes throughout, this move-in-ready home features an open, light-filled floor plan highlighted by floor-to-ceiling windows and a spectacular 38-foot covered terrace overlooking lush tropical gardens. Accessible from the living room and both bedrooms, the expansive terrace is the perfect place to enjoy your morning coffee, entertain guests, or relax with refreshing Gulf breezes. The updated kitchen flows seamlessly into the dining and living areas, creating an inviting space for everyday living and entertaining. Beautiful wood flooring, custom architectural details, stainless steel appliances, and abundant natural light add warmth and elegance throughout the home. The spacious primary suite serves as a private retreat with terrace access and a beautifully renovated ensuite bath featuring light wood cabinetry and granite countertops. The generous guest bedroom also opens to the terrace and includes a built-in Murphy bed, offering exceptional flexibility for visiting family and friends or a home office. Life at The Islander Club is truly resort-inspired. Residents enjoy over 400 feet of private Gulf-front beach, a heated beachfront swimming pool, a newly renovated state-of-the-art fitness center, two new sauna rooms, a Har-Tru® tennis court, two pickleball courts, a beautifully updated social room, library, secure key-fob entry, on-site management, and exceptional lock-and-leave convenience. Adding even greater value, The Islander Club has recently completed an extensive program of capital improvements, including exterior restoration and stucco repairs, balcony waterproofing, new roofs on both residential towers, clubhouse, and carports, modernized pool facilities with new tile, resurfacing, and equipment, refreshed landscaping and lighting, hurricane-rated windows and doors, and a completely renovated fitness center. These significant investments provide both peace of mind and long-term value for future owners. Whether you are searching for a full-time waterfront residence, a seasonal escape, or an exceptional investment opportunity, this beautifully updated condominium offers the very best of Longboat Key's coveted beachfront lifestyle.

2 Beds ⋅ 2 Baths ⋅ A4699335 MLS ⋅ 2301 BLDG.

Simply magnificent! This beautifully renovated residence offers the perfect blend of sophisticated design, comfort, and effortless coastal living. Thoughtfully updated with designer finishes throughout, this move-in-ready home features an open, light-filled floor plan highlighted by floor-to-ceiling windows and a spectacular 38-foot covered terrace overlooking lush tropical gardens. Accessible from the living room and both bedrooms, the expansive terrace is the perfect place to enjoy your morning coffee, entertain guests, or relax with refreshing Gulf breezes. The updated kitchen flows seamlessly into the dining and living areas, creating an inviting space for everyday living and entertaining. Beautiful wood flooring, custom architectural details, stainless steel appliances, and abundant natural light add warmth and elegance throughout the home. The spacious primary suite serves as a private retreat with terrace access and a beautifully renovated ensuite bath featuring light wood cabinetry and granite countertops. The generous guest bedroom also opens to the terrace and includes a built-in Murphy bed, offering exceptional flexibility for visiting family and friends or a home office. Life at The Islander Club is truly resort-inspired. Residents enjoy over 400 feet of private Gulf-front beach, a heated beachfront swimming pool, a newly renovated state-of-the-art fitness center, two new sauna rooms, a Har-Tru® tennis court, two pickleball courts, a beautifully updated social room, library, secure key-fob entry, on-site management, and exceptional lock-and-leave convenience. Adding even greater value, The Islander Club has recently completed an extensive program of capital improvements, including exterior restoration and stucco repairs, balcony waterproofing, new roofs on both residential towers, clubhouse, and carports, modernized pool facilities with new tile, resurfacing, and equipment, refreshed landscaping and lighting, hurricane-rated windows and doors, and a completely renovated fitness center. These significant investments provide both peace of mind and long-term value for future owners. Whether you are searching for a full-time waterfront residence, a seasonal escape, or an exceptional investment opportunity, this beautifully updated condominium offers the very best of Longboat Key's coveted beachfront lifestyle.

2301 Gulf Of Mexico Drive Unit 44N, Longboat Key