Longboat Key Homes with Community Mailbox Community Features

Longboat Key Homes with Community Mailbox Community Features

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Newest Longboat Key Homes with Community Mailbox Community Features

$4,290,000
2 Beds 3 Baths A4702788 MLS Champagne BLDG.
Tucked into the Champagne Building at The Residences at The St. Regis Longboat Key, unit 312 is a fully furnished coastal residence done right. Ceilings soar, glass walls stretch floor to ceiling, and the craftsmanship shows in every corner of this thoughtfully laid-out home. Step off the private elevator and into a great room capped by a dramatic tray ceiling and a sculptural bubble chandelier, where sliding glass doors open the space up to the terrace and the greenery beyond, letting the space extend beyond the walls. The kitchen is built for chef and entertainer alike. Glossy custom cabinetry, waterfall-edge counters with a leathered finish, a book matched quartz backsplash, and a full Wolf and Sub-Zero lineup, gas cooktop, double wall ovens, paneled refrigeration all give it the look of a showroom and the function of a real working kitchen. The island is the centerpiece for memories to be made with friends and family. The primary suite feels like its own retreat, tucked away from the living space with a wall of glass framing the grounds below. The bath is spa-worthy: dual vanities under illuminated round mirrors, a frameless glass rain shower, and a walk-in closet custom-fitted with enough drawers and shelving for a serious wardrobe. A second ensuite bedroom offers privacy for guests, and a well-appointed bath handles the rest. A discreet wet bar with wine storage and ice maker sits ready for evening cocktails, and wide-plank, wood-look porcelain tile runs throughout, warming up every room without competing with the views. Outside, the private terrace comes with its own Wolf gas grill, an easy spot for dinner under Longboat Key's evening skies. This is one of only 69 residences in the first branded residential community on the Gulf of Mexico with 800 feet of private beachfront. Ownership here comes with real perks: St. Regis Butler and Concierge service on call, a private Residents' Clubhouse and fitness center, a resident-only pool and spa, and beachside cabanas set aside just for owners. Steps beyond that, the full resort opens up: a heated infinity-edge pool, a drifting lazy river, a meandering saltwater lagoon home to a family of resident Aldabra tortoises, several chef-driven restaurants, and an oceanfront spa with vitality pools and a full menu of treatments. It's the kind of amenity list that makes staying home feel like a vacation. St. Armand’s Circle and downtown Sarasota are just minutes away, but out here on this stretch of Longboat Key, the pace slows down and the world feels a little further off. Here, you're not just buying a home, you're buying into the St. Regis way of doing life, every single day.

1591 Gulf Of Mexico Drive Unit 312, Longboat Key

$599,900
2 Beds 3 Baths A4706685 MLS N/A BLDG.
Discover your ultimate island escape in this beautifully updated, fully furnished, and pet-friendly 2-bedroom, 2.5-bathroom townhome located within the desirable Cedars Tennis Resort & Club on Longboat Key. Set across a lush, village-like community enveloped by nature on the island's scenic north end, this property offers a rare combination of relaxed coastal living and an excellent short-term rental opportunity featuring a flexible two-week policy. Step inside to find a turnkey, coastal-chic interior highlighted by crisp shiplap accents, warm wood-style flooring, and elegant metallic hardware throughout. The updated kitchen features white shaker cabinetry, premium stone countertops, custom tile backsplash, and a breakfast bar with seating, all while offering a subtle peekaboo views of the glistening Gulf of Mexico. It flows seamlessly into a bright dining space framed by a shell-pendant chandelier and an inviting living room that opens through sliding glass doors to a private, screened lanai framed by tropical palms and water views. Upstairs, the layout is designed for comfort and convenience. The primary suite serves as a serene retreat with water views, large closet space, and barn-door entry into an upgraded bathroom featuring dual vanities, white shiplap walls, and a walk-in shower with floor-to-ceiling marble tile and gold hardware accents. Just down the hall, the secondary bedroom, which also catches a peekaboo Gullf view, is accompanied by a second full bathroom and ther is also a dedicated upstairs laundry closet with front-loading washer and dryer units. Outside, the property enjoys tranquil views of lush tropical foliage and a quiet island setting, complete with recent structural and mechanical improvements like updated windows, a brand new roof, 2021 air conditioning units, and a private garage with recently install hurricane rated garage door. Cedars Tennis Club provides an unmatched resort-style atmosphere. Meander along lit boardwalks winding through mangroves to access an exceptional array of community amenities, including a heated Junior Olympic-sized swimming pool, a vibrant tiki bar, nine Har-Tru tennis courts, three Har-Tru pickleball courts, a clubhouse with a pro shop, a 24-hour fitness center, an on-site Google 5-star restaurant Hugo's II, a fishing pier, and a kayak launch (please note that some amenities require an additional club membership). When you are ready to venture out, you are within easy walking distance of Longboat Key's world-renowned sugary white sand beaches, the tranquil trails of Joan Durante Park, and local culinary staples like Harry's Deli & Continental Kitchen, Lo-Key Bar and Grill and Euphemia Haye Restaurant & The Haye Loft. For broader entertainment, shopping, and cultural experiences, St. Armands Circle, downtown Sarasota, the Ringling Museum complex, Mote Marine and Anna Maria Island are just a short drive away. Whether you are searching for the dream beach house, a lucrative investment property, or your own private full-time retreat complete with stunning evening sunsets, this Longboat Key gem delivers on every front.

521 Forest Way, Longboat Key

$1,495,000
3 Beds 3 Baths A4706065 MLS N/A BLDG.
3BR/2.5BA, 2,219 sf end-unit villa in gated Harbour Oaks at Bay Isles. Fairway views across hole #3 (White) of the Longboat Key Club golf course, plus a full-sized private heated pool on a large screened lanai. Three sliders open the living spaces to that outdoor room—ideal for gatherings, quiet evenings, and southwest-oriented sunsets over the greens. Renovated in a clean modern-farmhouse style: shiplap fireplace, new lighting and ceiling fans, paneled interior doors with dark hardware, and a wood-and-glass front door. The open, refreshed kitchen flows into the dining area overlooking the pool and golf course. The primary suite is a true retreat with multiple closets including a walk-in, double sinks, a newly tiled glass-enclosed shower, and a bathroom skylight. Two additional bedrooms and a bonus office with golf-course and garden-atrium views give the household room to work, guest, and spread out. Practical updates include a new roof with the assessment paid and a large two-car garage with epoxy floor and organized storage for beach and sports gear. Harbour Oaks residents have use of the private Bay Isles Beach Club on the Gulf (parking available). Longboat Key Club golf, tennis, pickleball, and dining are nearby by optional separate membership; the marina is a short walk, with slips available separately. Move-in ready Longboat Key living: golf-course backdrop, private pool, beach-club access, and lock-and-leave convenience behind the Bay Isles gates. Schedule your private showing and start living the island lifestyle.

2101 Harbourside Drive Unit 1103, Longboat Key

$1,495,000
2 Beds 2 Baths A4706200 MLS 5461 BLDG.
Step directly onto the sand from this pristine beachfront condo, where panoramic views of the ocean set the scene for total relaxation. Designed with an open-concept layout, the living area features 24x48 Carrara-style matte porcelain floor tile, wall-to-wall glass sliding doors that frame uninterrupted water views and open to a private covered balcony with a powered retractable screen as well as a security screen on both the balcony and master bedroom windows and all new impact windows and sliders. The Chefs kitchen features endless counter space and quartzite counter tops with full height quartzite backsplash, a breakfast bar, soft close cabinets and drawers, multiple custom drawers insert with organizers, dividers and pull outs. The luxury stainless-steel appliances include Sub Zero paneled triple-column integrated refrigeration suite with a 36” refrigerator, 18” freezer and 24” wine tower, a Marvel undercounter refrigerated beverage center, Café induction cooktop/double convection range and Café glass range hood. The ocean facing main bedroom with balcony access, offers a custom geometric coffered ceiling design with inset lighting, custom-built walk-in closet, Hunter Douglas dual electric shades with light filtering and black out shades. The elegant primary bath features custom cabinetry with under-cabinet lighting and generous storage including linen tower, pull out laundry hamper, built-in makeup area, dual vanities, marble counter tops, custom Glass enclosure and two shower heads with polished nickel individual Hansgrohe thermostatic valves. The large guest bedroom with wall-to-wall windows has a custom closet with mirrored pocket closet door as well as Hunter Douglas dual electric shades with light filtering and black out shades. The Guest bathroom has marble countertops, mosaic marble floor, European style floating vanity with under-cabinet lighting, double shower heads with Hansgrohe thermostatic valve and a custom glass enclosure. The laundry closet has a full-sized LG front loading washer and dryer with laundry folding quartzite countertop over the washer and dryer and upper cabinetry for storage. This residence comes with an enclosed under building parking space and a large storage closet with shelving. Amenities include a heated swimming pool surrounded by lush landscaping, tennis and pickleball court, beautiful dune walkway over to the beach, a grilling area, private beach access and an on-site property manager. This is a well-maintained boutique community of 2 buildings with only 26 total residences, pet friendly and walkable to 5 restaurants.

5461 Gulf Of Mexico Drive Unit 304, Longboat Key

$12,750,000
3 Beds 4 Baths A4684683 MLS Armand BLDG.
Presented in the most coveted beachfront enclave at The St. Regis Longboat Key Resort, this is a rare opportunity to own a spectacular residence in the prestigious Armand building — the closest to the Gulf, with breathtaking, unobstructed views of the Gulf of Mexico. Encompassing nearly 5,000 square feet and offered fully furnished, this extraordinary home was masterfully designed by the award-winning Rowland and Broughton of Aspen, Colorado. Thoughtfully curated throughout, it lives like a private single-family home while enjoying the legendary St. Regis services and amenities, including butler service and in-residence dining. The gracious great room is designed for effortless entertaining, featuring porcelain wood plank flooring and dramatic accordion doors that fully retract to a sprawling terrace with a private gas grill and panoramic views of the Gulf, resort, and saltwater lagoon — creating seamless indoor-outdoor living. The chef’s kitchen is a true showpiece, anchored by a large statement island clad in exquisite Pininfarina Crystal quartzite with a dramatic waterfall edge — blending sculptural beauty with everyday functionality. The space is impeccably appointed with dual Cove dishwashers, a Wolf six-burner cooktop, Wolf double ovens and microwave, and a Sub-Zero refrigerator. A charming breakfast area offers built-in storage and shelving, along with an ice maker and beverage refrigerator for ultimate convenience. A private club room provides the perfect setting for lounging or game day gatherings, highlighted by custom built-ins and striking in-wall wine storage. The luxurious owner’s suite captures sweeping Gulf views and opens directly onto the expansive terrace. A stunning feature wall wrapped in Bijou Knits wallpaper by Phillip Jeffries adds refined texture and sophistication, complementing the custom built-ins that define this serene retreat. The spa-inspired bath features dual oversized vanities (including a dedicated makeup area), illuminated mirrors, a soaking tub, seamless glass shower, two private water closets with Toto electric toilets, and custom closets. Two additional guest suites offer comfort and privacy. The second features custom built-ins with a king Murphy bed, integrated desk, generous closets, and a bath with double vanities and glass shower, opening to terrace views of Sarasota Bay. The third is equally spacious, also opening to the terrace with bay views and offering double vanities and custom closets. An elegant laundry room continues the home’s elevated aesthetic with custom cabinetry, a utility sink, and SM Quartz by Santa Margherita countertops. Throughout, porcelain wood plank floors, electronic shades, and a state-of-the-art Crestron smart home system enhance everyday living. The integrated technology package — valued at approximately $400,000 — controls lighting, blinds, televisions, and music throughout the home. This is an exceptional opportunity to own one of the most refined residences on Longboat Key — where five-star resort living meets the privacy and comfort of a grand coastal home. Residents enjoy a private clubhouse with fitness center, resident-only pool and spa, St. Regis Butler and Concierge services, an oceanfront spa, dining venues, beachfront cabanas, lazy river, and saltwater lagoon. Set on 17 acres of pristine beachfront just 3.5 miles from St. Armands Circle, this home invites you to embrace the legendary St. Regis lifestyle.

1561 Gulf Of Mexico Drive Unit 404, Longboat Key

$425,000
2 Beds 2 Baths A4704453 MLS G BLDG.
MAJOR $74,000 PRICE REDUCTION, don't miss this newly priced opportunity. Experience the best of Bay-to-Gulf living in this beautifully furnished condominium located on the top-floor in Building G at Longboat Harbour. Featuring 2 bedrooms and 2 bathrooms, this move-in-ready residence offers peaceful canal views, thoughtful updates, and exclusive access to a private, gated beach club on the Longboat Key Gulf Beach, just steps away. Building G also offers a special community feature: a dedicated bump-out area designed for residents’ outdoor gatherings and entertaining. This exclusive feature is available to only two buildings within Longboat Harbour, and Building G is one of them. The bright and inviting interior features a carpet-free design with luxury vinyl plank flooring throughout with tiled bathrooms. New lighting fixtures, custom window treatments and ceiling fans add a fresh, updated touch, while the kitchen is appointed with granite countertops and a stylish backsplash. The updated primary bathroom provides additional comfort and modern appeal with custom vanity and cabinet storage. A new HVAC system installed in 2025 offers added peace of mind. Step outside to the spacious screened lanai, where beautiful canal views create a relaxing backdrop for everyday living, and on those lucky days, you may even catch a glimpse of manatees swimming peacefully through the water. Enhanced by a ceiling fan, this private outdoor space is perfect for enjoying morning coffee, reading a good book, entertaining guests, or unwinding at the end of the day. The condominium is being sold furnished with carefully selected pieces that complement the home’s coastal style and create a warm, comfortable atmosphere. Whether you are searching for a full-time residence, seasonal getaway, or coastal vacation retreat, this property is ready to enjoy from the moment you arrive. Longboat Harbour at Longboat Key offers an exceptional waterfront lifestyle with access to both Sarasota Bay and the beautiful Longboat Key Beach. The community’s private, gated beach club provides a convenient place to relax on the sand, enjoy the Gulf breeze, and take in beautiful Florida sunsets. Residents also enjoy an impressive selection of resort-style amenities, including four heated swimming pools, a fully equipped fitness center, tennis and pickleball courts, fishing piers, kayak & bicycle storage, and boat slips available on a first-come, first-served basis. The community clubhouse/banquet hall offers social events and activities, providing plenty of opportunities to meet neighbors and enjoy an active coastal lifestyle. Ideally situated on Longboat Key, this gated waterfront community offers convenient access to some of the area’s best dining, shopping, and entertainment while maintaining a peaceful and private setting. Whether used as a serene retreat, vacation property, or full-time residence, this furnished condominium provides everything needed to experience the very best of Longboat Key’s Bay-to-Gulf lifestyle. Schedule your private showing or request your virtual tour today, don't miss out this GEM on Longboat Key.

4370 Chatham Drive Unit 304, Longboat Key

$2,675,000
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
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

$139,000
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

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