Sarasota/Crescent Beach/Siesta Key Homes with Association Recreation - Owned Community Features

Sarasota/Crescent Beach/Siesta Key Homes with Association Recreation - Owned Community Features

Welcome to the enchanting coastal paradise of Siesta Key, nestled in the heart of Sarasota County, Florida. Known for its powdery white sands and vibrant turquoise waters, Siesta Key is a dream destination for beach lovers and those seeking a serene lifestyle. This idyllic island community offers a perfect blend of natural beauty, lively local culture, and luxurious living.

Crescent Beach, one of Siesta Key's most cherished spots, boasts stunning sunsets and gentle waves, making it an ideal location for relaxation and recreation. Residents and visitors alike can enjoy a plethora of outdoor activities, from paddleboarding and kayaking to beach volleyball and sunbathing. The nearby Siesta Key Village is brimming with charming boutiques, delightful restaurants, and lively nightlife, ensuring there’s always something to do just moments from your doorstep.

For those seeking a sense of community, the homes in Siesta Key with Association Recreation offer a unique lifestyle experience. These owned community features provide residents with access to exclusive amenities, including swimming pools, tennis courts, and clubhouses, fostering a vibrant social atmosphere. Whether you’re looking to mingle with neighbors or enjoy a quiet evening under the stars, these communities cater to all preferences.

With its stunning natural landscapes, thriving local culture, and community-oriented living, Siesta Key is not just a place to live; it’s a lifestyle to embrace. Discover your dream home in this picturesque paradise and experience the best that Florida has to offer!

Newest Sarasota/Crescent Beach/Siesta Key Homes with Association Recreation - Owned Community Features

6005 Midnight Pass Road Unit S6, Siesta Key
$839,000
2 Beds ⋅ 2 Baths ⋅ A4709210 MLS
Escape the winter blues with this turnkey furnished free-standing villa ready for IMMEDIATE occupancy with DEEDED SIESTA KEY BEACH and BAY access steps away in a non age restricted community. No logistical headaches having to furnish a property in order to occupy or rent it. This beautifully decorated and extensively updated, maintenance-free, open floor plan, villa can be your very own piece of paradise. Offering two spacious bedrooms and bathrooms, a flex (den) space, a full size washer/dryer, and your very own lush private patio oasis, all designed with comfort and style in mind. Added peace of mind comes from no flooding or storm damage sustained from recent storms. Some of the many updates include an extensive renovation to replace the old 1960s cast iron drain lines under the property’s slab with all-new PVC lines. Once completed, designer selected wood look tile flooring was added throughout the majority of the home. This intrusive, time-consuming, and costly project has already been completed, putting a new owner at ease regarding future concerns and major costs. The roof and A/C are new as of 2025, exterior painting will be completed by December. The primary bathroom has been completely updated, along with new hardscaping and landscaping. Handpicked light fixtures and ceiling fans have been installed, along with brand new solid core doors throughout the home to reduce noise from room to room. New coastal colors and tones have been added to the interior, along with all new appliances within the past two years. For accessibility 36 inch doorways and grab bars are present, as well as smart home features such as keyless electronic front door entry, nest thermostat, and ring door bell. The residence invites plenty of natural light into the home, with multiple windows and sliding glass doors enhancing the appeal of the split floor plan. The primary and expansive guest suite are located on opposite sides of the villa, providing ample space and privacy for all. The kitchen features an abundance of soft close cabinets, granite countertops, a large pantry, water filter system, and stainless steel appliances. Throughout the villa, you will find plenty of built-in storage closets, crown molding, as well as both a walk-in shower (primary) and a soaking tub (guest). Open your three sliding glass doors to create a seamless extension of your living space into your private tropical sanctuary, complete with an outdoor shower. The guest suite includes its own private outdoor space with a water fountain. When you are ready to venture out and enjoy your surroundings, there is an endless list of options to keep you busy. Enjoy your morning coffee while watching the sunrise/wildlife at the community’s bay front park with a new seawall. Here, you will find a kayak launch with two storage racks specifically for your use. Head out on the water kayaking/paddle boarding among dolphins and manatees. The community’s bay front park includes a day dock for residents’ use. Choose between relaxing on the beach with the sand between your toes or reading a book by the pool, with deeded access to the beach and one of the largest heated pools on Siesta Key via Aloha Kai across the street. Catch the free trolley to enjoy a casual lunch or a fine dining dinner. Owners can rent their property on a monthly basis with three weekly rentals permitted a year (outside of Jan-March) and can have one pet. The monthly HOA fee is $1,113. Come enjoy winter on Siesta Key!

6005 Midnight Pass Road Unit S6, Siesta Key

1229 Moonmist Circle Unit P6, Siesta Key
$625,000
2 Beds ⋅ 2 Baths ⋅ G5118459 MLS ⋅ N/A BLDG.
TURNKEY FURNISHED, FREE-STANDING VILLA ON SIESTA KEY! TAKE YOUR GOLF CART TO PUBLIC BEACH! Ideally located in the highly desirable Polynesian Gardens along the Intracoastal Waterway, this charming 2-bedroom, 2-bath villa offers the privacy and feel of a single-family home with the convenience of low-maintenance, lock-and-leave living. TWO DOGS ALLOWED! LOW HOA FEES. An excellent choice for a personal island retreat. One of only ten villas overlooking the expansive community pool, this home features a private entrance, covered carport, screened lanai, and inviting outdoor living spaces surrounded by lush tropical landscaping. Relax around the LP gas fire pit or enjoy the Florida sunshine just steps from the community pool. The villa is also positioned at one of the higher elevations within the community. Major updates include a NEW ROOF (2023), HVAC SYSTEM (2023), WATER HEATER (2025), NEW GUTTERS (2025), programmable Nest thermostat, remote-entry touch keypad lock, and remote camera system. (OVER $100,000 OF RENOVATIONS HAVE BEEN DONE.) Enjoy everything the Siesta Key lifestyle has to offer! Spend your days fishing or watching dolphins and manatees from the community dock and fishing pier overlooking the Intracoastal Waterway. Walk or take your GOLF CART to nearby dining, shopping, coffee shops, nightlife, grocery stores, marina access, and local favorites including Captain Curt’s. World-famous Siesta Key Beach, known for its powdery white quartz sand, is just across the street. Hop aboard the free trolley to Siesta Key Village for even more dining, shopping, and entertainment. Rental history is available in the attachments. Whether you’re looking for your own island getaway, a seasonal rental, or an easy-care Florida retreat, this villa offers an exceptional opportunity to enjoy the ultimate Siesta Key lifestyle. MOVE IN, RENT OUT, OR SIMPLY RELAX!

1229 Moonmist Circle Unit P6, Siesta Key

6006 Midnight Pass Road Unit 11, Siesta Key
$449,000
1 Beds ⋅ 1 Baths ⋅ A4708157 MLS ⋅ B BLDG.
Your opportunity to own on Siesta Key at an exceptional value with nearly 200 feet of deeded beach frontage! The lowest-priced condo on Siesta Key, this charming TURN KEY, 1-bedroom, 1-bath plus two additional sleeper sofas at Casa Mar has been refreshed by new owners including some new plumbing in the bathroom and offers an incredible opportunity for an island retreat, seasonal escape or income-producing vacation rental. The possibilities are endless! Walk to Siesta Key’s world-famous white quartz sand beaches and the turquoise waters of the Gulf of Mexico, this beachside condo offers 600 sq. ft condo of interior living, 108 sq. ft. of screened-in lanai, AND a brand new outdoor paver patio that is being completed as we speak which will be so cute set up as an outdoor seating area! Inside, vintage island character meets relaxed coastal living with freshly painted vaulted wood-beamed ceilings, timeless terrazzo flooring, abundant natural light, and an open living area flowing seamlessly to the screened lanai, an ideal spot for morning coffee or unwinding after a day at the beach. The kitchen features solid-surface countertops, eat-in dining area and opens to the main living space, while the spacious bedroom offers ample storage including built-in closet cabinetry. The bathroom includes a walk-in shower. Recent improvements include a new A/C in 2025, new building roof in 2024, water heater in 2021, and partial impact windows. An assigned covered carport is located directly outside your ground floor private entrance, making everyday access effortless with no stairs to navigate. Casa Mar delivers the Siesta Key lifestyle buyers dream of with private deeded beach frontage, two covered beach pavilions, two community pools, tennis and pickleball, basketball, clubhouse, four BBQ grilling areas with picnic tables, and community laundry facilities. The condo fee includes cable TV, internet, water/sewer, building insurance, and grounds maintenance. Even better, the Siesta Key Breeze Trolley stops right at the Casa Mar entrance on Midnight Pass Rd, offering convenient transportation around the island whether you’re enjoying a night on the town in the village or Turtle Beach on the south end. Whether looking for an affordable slice of Siesta Key to call your own, a lock-and-leave beach getaway that can also serve as both a vacation home and an income generating vacation rental, this is one you won't want to miss. Siesta Key Beach! Exceptional amenities! Weekly rentals! AND the lowest-priced condo on Siesta Key, this is your chance to own your piece of the island!

6006 Midnight Pass Road Unit 11, Siesta Key

5600 Beach Way Drive Unit 207, Siesta Key
$739,000
2 Beds ⋅ 2 Baths ⋅ A4708437 MLS ⋅ 5600 BLDG.
LOCATION, LOCATION, LOCATION! This beautifully updated 2 bed, 2 bath home, ideally located directly across from world-famous Siesta Key Beach. Offering views of the pool, lush landscaping, and a partial ocean view, this gorgeous turnkey furnished residence combines a relaxed coastal setting with an exceptional location. The thoughtfully updated interior features luxury vinyl plank flooring throughout and a stunning kitchen with custom cabinetry, quartz countertops, a subway and mosaic-style backsplash, and a center island with convenient breakfast seating. The defined dining and living areas provide a comfortable space for both everyday living and entertaining, with sliding glass doors extending the living space onto the balcony and bringing the outdoors in. The primary suite offers an ensuite bath, walk-in closet, and its own sliders leading to the balcony. The spacious guest bedroom includes a Murphy bed cabinet, providing flexibility for guests when needed, along with a second full bath. Benefiting from hurricane impact windows for peace of mind this tastefully decorated home is ready to enjoy from day one! Step outside and enjoy the peaceful surroundings from the private balcony or take advantage of the unbeatable location just across from Siesta Key Beach. Stroll to the Village for its lively music, dining, and shopping, or hop aboard the free beach trolley for an easy way to explore the island. With Sarasota's downtown arts, culture, dining, and entertainment just a short drive away, along with the boutiques, restaurants, and waterfront atmosphere of St. Armands Circle, this property offers the perfect balance of beach living and convenience. Whether you're looking for a vacation home, a place to escape and enjoy the Florida lifestyle, or an investment opportunity, this inviting Siesta Key residence offers a wonderful combination of location, updates, and relaxed coastal living.

5600 Beach Way Drive Unit 207, Siesta Key

1350 Siesta Bayside Drive Unit 1350B, Siesta Key
$899,000
3 Beds ⋅ 2 Baths ⋅ A4708214 MLS ⋅ 1350 BLDG.
Experience turnkey island living in this second-floor, three-bedroom townhome residence at Gulf & Bay Club Bayside on Siesta Key. Offered fully furnished and operating as an active rental with strong income history, this two-story getaway presents an outstanding opportunity for personal enjoyment and investment potential in one of Sarasota’s most desirable beach communities. Spanning nearly 1,500 square feet, the light-filled layout features tile flooring throughout the main living areas, high ceilings, and an open living/dining design ideal for gathering and entertaining. The updated granite kitchen is equipped with stainless-steel appliances, custom cabinetry, breakfast bar seating, built-in planning desk, and a sunny dining nook with additional storage. French doors open to the screened terrace, where added windows transform this space into a true year-round Florida room—an upgrade not commonly found in many Bayside residences. This enhancement expands the usable living area and allows you to enjoy the outdoor setting in every season, whether hosting guests or relaxing after a day at the beach. The primary suite is conveniently positioned on the main level and offers a walk-in closet, granite-appointed en-suite bath, and direct access to the enclosed terrace. Upstairs, a versatile loft provides flexible living space, while two guest bedrooms share a full bath—creating an ideal layout for visiting family or rental guests. This residence includes a deeded garage space and benefits from weekly rental flexibility, further enhancing its income-producing appeal. Unique Opportunity: We also have a second Gulf & Bay Club Bayside residence available in nearby Building 1328 on the first floor. Purchasing both properties would provide a rare chance to own five bedrooms within the same community—perfect for larger family gatherings, seasonal hosting, or multigenerational stays. Owners would enjoy the flexibility to occupy one unit while renting the other or maximize rental income throughout the year. Gulf & Bay Club Bayside is known for its coastal architecture and resort-style amenities. Residents enjoy heated swimming pool, tennis and pickleball courts, fitness center, clubhouse, grilling stations, and a fishing dock on the Intracoastal Waterway. Deeded beach access directly across the street places Siesta Beach’s renowned quartz sands and Gulf waters just moments away. Located in the heart of Siesta Key, this residence offers convenient access to Siesta Village’s restaurants, boutiques, and live music. Boating, paddleboarding, and waterfront dining are close by, while downtown Sarasota—home to the Sarasota Opera House, Selby Gardens, The Bay Park, and St. Armands Circle—is just a short drive away. Whether seeking a beach retreat, a rental investment, or the flexibility of dual-unit ownership on Siesta Key, this Gulf & Bay Club Bayside residence delivers location, versatility, and exceptional lifestyle value.

1350 Siesta Bayside Drive Unit 1350B, Siesta Key

1328 Siesta Bayside Drive Unit 1328C, Siesta Key
$699,000
2 Beds ⋅ 2 Baths ⋅ A4708199 MLS ⋅ Gulf & Bay Club Bayside BLDG.
Welcome to Gulf & Bay Club Bayside, one of Siesta Key’s most desirable resort-style communities. This turnkey-furnished residence offers the perfect blend of coastal comfort, modern updates, and access to Siesta Key’s world-famous beaches. Designed with a bright, open layout and porcelain tile flooring throughout, the interior feels fresh and inviting from the moment you step inside. Oversized windows and glass sliders fill the home with natural light and extend the living space to the screen-protected lanai, creating an ideal spot to relax after a day at the beach. The updated kitchen features stone countertops, contemporary cabinetry, quality appliances, and generous storage. The dining and living spaces connect effortlessly, giving the residence a comfortable flow for both everyday living and seasonal enjoyment. Both bedrooms provide privacy for owners and guests, and the primary suite features a walk-in closet, en-suite bath, and direct access to the lanai. A second bedroom serves well as a guest room, home office, or multi-use space. Unique Opportunity: We also have a second Gulf & Bay Club Bayside residence available in the same building on the second floor, a townhome layout. Purchasing both properties would provide a rare chance to own five bedrooms within the same community—perfect for larger family gatherings, seasonal hosting, or multi-generational stays. Owners would enjoy the flexibility to occupy one unit while renting the other or maximize rental income throughout the year Gulf & Bay Club Bayside is known for its beautiful coastal architecture and outstanding amenities. Residents enjoy two heated swimming pools, tennis courts, pickleball, a well-equipped fitness center, grilling stations, a fishing dock on the Intracoastal Waterway, and a stylish clubhouse. The community’s deeded walking beach access—located directly across the street—places you moments from Siesta Beach’s unique shores and turquoise water, making it effortless to enjoy sunrise or sunset strolls, and spontaneous beach days. Situated in the heart of Siesta Key, the location offers quick access to the island’s best attractions. Explore nearby Siesta Village, known for its open-air restaurants, boutique shops, live music, and laid-back coastal atmosphere. Boaters will appreciate the proximity to the Intracoastal Waterway, marinas, and local rental options. For even more dining, arts, and entertainment, vibrant downtown Sarasota is just a short drive away—home to the Sarasota Opera House, Van Wezel Performing Arts Hall, Selby Gardens, the Ringling Museum, St. Armands Circle, and an ever-growing culinary scene. Whether you’re seeking a full-time residence, a seasonal getaway, or an investment opportunity with weekly rentals permitted, this Gulf & Bay Club Bayside property delivers the ideal combination of location, lifestyle, and value on Siesta Key.

1328 Siesta Bayside Drive Unit 1328C, Siesta Key

4708 Ocean Boulevard Unit E4, Siesta Key
$2,199,000
3 Beds ⋅ 3 Baths ⋅ A4707998 MLS ⋅ Windward Passage BLDG.
Expansive floor-to-ceiling sliders open wide to welcome refreshing Gulf breezes and showcase unobstructed, panoramic water views, turning your open-floorplan living space into an indoor/outdoor oasis. With over 2,300 square feet, this light-filled condominium lives like a private home suspended above shimmering waters. The gourmet kitchen is both elegant and functional, featuring quartz countertops, custom wood cabinetry, and premium appliances, including a Thermador refrigerator and freezer, Wolf double ovens, Wolf microwave, and a Thermador induction cooktop. Panel-ready finishes, a built-in beverage cooler, and exceptional storage make this space ideal for both everyday living and entertaining. Rich acacia engineered wood flooring adds warmth and sophistication throughout the main living areas. The spacious primary suite captures sweeping Gulf views and offers a serene escape, complete with a beautifully renovated spa-inspired bath featuring split vanities and a large walk-in shower. Two additional bedrooms and stylishly updated baths are thoughtfully positioned on the opposite side of the residence for added privacy. Impact-rated windows and sliders provide peace of mind, eliminating the need for hurricane shutters. A private two-car garage with ample storage adds to the home’s convenience. Windward Passage features a Gulf-side pool, lushly landscaped grounds, and a pet-friendly setting. Perfectly positioned on the sought-after north end of the key, you’re just a short walk to the Village for charming boutiques, dining, and live entertainment.

4708 Ocean Boulevard Unit E4, Siesta Key

5855 Midnight Pass Road Unit 605, Siesta Key
$719,000
2 Beds ⋅ 2 Baths ⋅ A4706819 MLS ⋅ Harbor Towers Y & R BLDG.
Harbor Towers 605 represents a unique opportunity to live on a high floor in the building with the coveted south-facing views looking over the pool. Welcome to Harbor Towers, your home at the beach- this perennial favorite building is now better than ever after undergoing massive exterior renovations which include strengthening and impact glass windows and sliding doors for all units! The unique and large grounds of Harbor Towers provide a spectacular setting with lots of space to enjoy the coastal lifestyle. You are not just buying a home, you're buying into a Yacht and Tennis Club, with har-tru tennis courts, a recently revamped marina with inexpensive boat mooring prices, a heated community pool, fitness center, meeting area, community kayak area and much much more. This unit has been renovated and lovingly cared for over the years. Besides the impeccable view down the Intracoastal Waterway, this unit offers well maintained luxury featuring tile floors throughout, kitchen update in 2021, in unit washer/dryer combo, full furniture package included- just to name a few. This unit must be seen to be appreciated. It is currently positioned in the rental program, but can be removed if desired. Pick your desired lifestyle- keep it all to yourself or earn some income to help pay for your investment. Harbor Towers is well taken care of and well managed. Onsite management, security and well funded reserves make this complex a true winner. This unit also has a covered carport spot that is included in the purchase. Don't wait on this opportunity- these types of units don't come to market very often. Schedule your private showing today!

5855 Midnight Pass Road Unit 605, Siesta Key

8701 Midnight Pass Road Unit 304A, Siesta Key
$649,000
2 Beds ⋅ 2 Baths ⋅ A4706193 MLS ⋅ 8701 BLDG.
Experience the ultimate Bayfront lifestyle on Siesta Key in this turnkey furnished 2BR/2BA residence at Turtle Bay. Tucked away on the serene south end of the island, this spacious condo blends modern coastal luxury with vibrant island living. Wake up to spectacular sunrises over the Intracoastal from your private, enclosed lanai, and wind down with sunsets via deeded beach access directly across the street. The generous primary suite features a walk-in closet, and a private entrance to the lanai. An in-unit laundry room includes a full-size washer/dryer and extra storage—a rare luxury on the Key! Additional upgrades include hurricane-impact windows to perfectly frame the water views. One of the most valuable features is the private, oversized 1-car garage providing secure parking and ample gear storage. Pet-friendly Turtle Bay offers premium amenities: brand-new boat docks/slips (just $300/year and you can add your own hoist), an updated fishing pier, kayak launch/storage, heated pool/spa, lighted tennis/pickleball courts, shuffleboard, clubhouse, and grilling area. Enjoy maintenance-free ease with on-site management, secure entry, and elevators. Leave your car behind and take the free trolley to nearby Siesta Village, South Village, or Point of Rocks snorkeling. Just minutes to Stickney Point Bridge and 20 minutes to downtown Sarasota. Perfect as a full-time residence, seasonal escape, or a great investment income opportunity.

8701 Midnight Pass Road Unit 304A, Siesta Key

116 Vista Hermosa Circle Unit 108C, Siesta Key
$400,000
2 Beds ⋅ 2 Baths ⋅ N6145721 MLS ⋅ 116 BLDG.
Your Siesta Key Lifestyle Awaits — The Time to Own Is Now! Welcome to one of Sarasota’s most sought-after coastal destinations, where the beauty of Siesta Key is right outside your door. This completely updated ground-floor residence captures the true essence of coastal living with a soft, neutral palette and a relaxed, welcoming atmosphere. This property sets itself apart from all the others—it makes you feel right at home at the beach the minute you arrive. The spacious bedrooms provide plenty of room for family and guests, with the oversized guest bedroom large enough to accommodate two full-size beds, comfortably sleeping four. The beautifully refreshed kitchen features new appliances, quartz countertops, updated cabinetry, and a new tile backsplash that perfectly complements the home’s coastal-inspired design. Extend your enjoyment outdoors in the enclosed lanai, offering privacy and a comfortable space to enjoy year-round. There is also the possibility of adding a paver extension to the lanai, creating even more outdoor living space for relaxing and entertaining. A convenient in-unit laundry closet with washer and dryer adds to the ease of everyday living, while storm windows and doors provide added peace of mind. And then there’s the lifestyle! Spend your days enjoying the world-famous sands of Siesta Key Beach, explore the beauty of Selby Gardens, shop and dine at St. Armands Circle, or head into downtown Sarasota for its incredible restaurants, arts, culture, and waterfront attractions. And don’t miss one of the area’s most anticipated fall events—the Siesta Key Crystal Classic Sand Sculpting Festival. Come be part of the fun, experience the incredible artistry, and enjoy yet another reason why life on Siesta Key is so special. The time is now to make this coastal retreat your own and be ready for the 2027 season. Whether you’re looking for a full-time residence, a beach escape, or your own piece of the Siesta Key lifestyle, this beautifully updated home offers something truly special. Come see for yourself why this one feels different. Your beach lifestyle begins the minute you arrive.

116 Vista Hermosa Circle Unit 108C, Siesta Key

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