Longboat Key Homes with 55+ Only

Longboat Key Homes with 55+ Only

Welcome to Longboat Key, Florida, a stunning barrier island that offers a unique blend of tranquility, natural beauty, and vibrant community life. Nestled along the sparkling Gulf Coast, Longboat Key boasts pristine beaches, lush landscapes, and an inviting atmosphere that attracts residents and visitors alike. With its year-round sunshine and warm climate, this idyllic locale is the perfect retreat for those seeking a peaceful lifestyle by the sea.

One of the highlights of Longboat Key is its thriving 55+ community, which provides a welcoming environment for active adults looking to enjoy their golden years. Here, you will find an array of charming homes tailored to meet the needs and desires of those aged 55 and older. These residences often feature spacious layouts, modern amenities, and easy access to beautiful outdoor spaces, ensuring that you can enjoy a relaxed and fulfilling lifestyle.

In addition to its picturesque homes, Longboat Key offers a wealth of recreational opportunities. Residents can indulge in a variety of activities, from golfing at world-class courses to exploring the scenic walking and biking trails. The island is also home to an array of dining options, boutique shopping, and cultural attractions that cater to diverse tastes.

Whether you’re looking to spend your days lounging on the beach, engaging in social events, or exploring the stunning surroundings, Longboat Key’s 55+ community provides the perfect backdrop for a vibrant and fulfilling lifestyle. Discover your dream home in this serene paradise and embrace the joys of coastal living today!

Newest Longboat Key Homes with 55+ Only

2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code

Experience the best of Longboat Key in this beautifully appointed coastal retreat, nestled within the highly sought-after 55+ community of Spanish Main Yacht Club! This newly remodeled 2-bedroom, 2-bathroom residence is offered fully furnished turnkey with all brand-new, high-end coastal furnishings. Ideally situated just steps from the active marina and a picturesque seawall—perfect for peaceful mornings, frequent dolphin and manatee sightings, and stunning bayfront sunrises—you'll also enjoy Gulf-side beach sunsets just a short stroll away. Thoughtfully designed, the home offers premium mattresses dressed in organic cotton linens and a fully stocked kitchen, providing a refined, move-in ready living experience from the moment you arrive. Residents enjoy access to a fantastic array of community amenities, including a private marina with available boat docks and kayak storage, deeded beach access, a heated community pool, and shuffleboard courts. Ideally located just minutes from the upscale dining and boutiques of St. Armands Circle and a scenic drive to Anna Maria Island, this property offers the perfect blend of active-adult tranquility and local accessibility. Whether you are boating, fishing, or relaxing in the bright, inviting Florida room, this is a rare opportunity to live the ultimate Longboat Key lifestyle.

914 Spanish Drive S Unit 76, Longboat Key

2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code

Experience the ultimate Longboat Key lifestyle in this beautifully renovated single-story villa located in the highly sought-after 55+ waterfront community of Spanish Main Yacht Club. This move-in-ready 2-bedroom, 2-bath residence features a bright, open floor plan, brand-new appliances, updated finishes throughout, and a spacious Florida room perfect for relaxing or entertaining. Ideally situated just steps from the community marina, enjoy peaceful mornings watching manatees and dolphins while taking in breathtaking sunrise views over Sarasota Bay. Deeded private beach access to the Gulf of Mexico is just a short stroll away, offering unforgettable sunset walks along the sugar-sand beaches. Residents enjoy a maintenance-free lifestyle with exceptional amenities, including a heated community pool, clubhouse, library, shuffleboard courts, and marina with boat docks and kayak storage (subject to availability). An active social environment makes Spanish Main Yacht Club one of Longboat Key's most desirable waterfront communities. Conveniently located just minutes from the world-class shopping and dining of St. Armands Circle and the charm of Anna Maria Island, this villa is ideal as a year-round residence, seasonal getaway, or investment opportunity. Don't miss your chance to own a slice of paradise on Longboat Key.

683 Spanish Drive S Unit 214, Longboat Key

2 Beds ⋅ 2 Baths ⋅ Twin Shores Mobile Home SubDv. ⋅ 34228 Zip Code

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

2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code

Welcome to 578 Spanish Drive S, a completely renovated 2 bedroom, 2 bathroom villa in Spanish Main Yacht Club on Longboat Key. Renovated completely with thoughtful attention to detail, this move-in ready residence showcases high-quality modern finishes while providing access & amenities to one of Longboat Key's established waterfront communities with a deepwater marina and deeded beach access. The redesigned interior features an open kitchen centered around a quartz waterfall edge island, soft close cabinetry, with all new stainless-steel appliances, including a wine refrigerator and a refrigerator with a built-in craft ice maker. Luxury vinyl plank flooring extends throughout the home, complemented by a smart thermostat for everyday convenience. Every room reflects the comprehensive renovation, and the home is further enhanced by a 2012 tile roof, new PGT hurricane impact windows, and sliding glass doors that open to a private paver patio overlooking a wooded landscaped setting. Spanish Main Yacht Club offers private deeded beach access to the Gulf of Mexico, a heated community pool, clubhouse, shuffleboard courts, and a pet-friendly environment. The community’s deepwater marina offers approximately 40 boat slips available for lease, accommodating vessels up to 40 feet with water and electric service, while providing direct boating access from Sarasota Bay to the Gulf of Mexico. Residents also enjoy opportunities for fishing, kayaking, paddleboarding, and other waterfront recreation. Located near Publix, St. Armands Circle, downtown Sarasota, shopping, dining, cultural attractions, botanical gardens, Anna Maria Island, and Sarasota-Bradenton International Airport, this extensively renovated villa offers an exceptional combination of updated interior finishes, outdoor living, boating amenities, and convenient access to the best of Longboat Key and the surrounding Sarasota area. Please see attached document for the full list of renovations & upgrades and full walkthrough video and virtual walkthrough. Not required to be 55 to purchase.

578 Spanish Drive S, Longboat Key

1 Beds ⋅ 1 Baths ⋅ Gulfshore Of Longboat Key SubDv. ⋅ 34228 Zip Code

BEAUTIFULLY REMODELED: This home is the epitome of simple elegance with a bit of modern flair. It has been remodeled to create a home that is very open and full of light. It features a large Living Room with a wall-mounted TV and a fireplace; a kitchen that has all new cabinets and granite counter tops; a Primary bedroom, with a small attached room that could easily be converted to a small bedroom. The full Bath features a step-in shower. In addition, there is an outside bath house, that has been totally remodeled, and has a toilet, sink and shower that is perfect for when you return from the beach. Gulfshore of Longboat Key is located on a perfect parcel of land. It has it all – approximately 450-500 feet of private access to a pristine sand beach on the turquoise waters of the Gulf of Mexico, a marina on Sarasota Bay, large community heated pool, remodeled clubhouse with a commercial kitchen, and a well-maintained and managed campus. Gulfshore is proud of their financial management and the very affordable cost of living that has resulted. Truly, Gulfshore is a remnant of Old Florida that is just six miles from the world-famous St. Armand’s Circle. St. Armand’s has a plethora of great restaurants and world-class shopping. Gulfshore does not permit rentals or pets and it is a 55+ community. Please call now to schedule your personal showing and to view your future home and live the Florida dream.

3710 Gulf Of Mexico Drive Unit E22, Longboat Key

2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code

Welcome to Spanish Main Yacht Club, one of Longboat Key's most beloved waterfront communities, where 55-plus living unfolds at an easy, unhurried pace between the Gulf of Mexico and Sarasota Bay. Tucked along a quiet street lined with tidy single-story villas and swaying palms, this fully renovated two-bedroom retreat captures the old-Florida charm that makes this island enclave so special, paired with the fresh, move-in-ready updates. Behind the arched front entry and crisp white stucco exterior with its white tile roof, a bright open interior welcomes you, where neutral tile floors run throughout and natural light pours through plantation-shuttered windows. The renovated kitchen is the heart of the home, outfitted with white shaker cabinetry, quartz countertops, a waterfall-edged peninsula, a soft glass-tile backsplash, and crisp white appliances, all opening to a generous living and dining area finished with crown molding and an easy coastal feel. A versatile bonus room wrapped in windows, with a door to the back patio, makes a wonderful sunroom, reading retreat, or home office. Both bedrooms are comfortable and well-appointed, served by two beautifully updated bathrooms, one with a tub and shower framed in subway tile, the other a glass walk-in shower with a mosaic floor and designer fixtures. A covered carport with room for a golf cart, plus interior storage for kayaks and beach gear, adds everyday ease. Brick paver walkways and lush tropical landscaping wrap the home, and the concrete tile roof is just over five years young. Life at Spanish Main is built around the water and the warmth of neighbors. Residents enjoy a heated pool overlooking the basin, a clubhouse, shuffleboard courts, kayak storage and launch, and a deep-water marina with boat slips available for a monthly fee, offering quick access to Sarasota Bay and the Gulf beyond. Best of all is the community's private Gulf beach access, just a short stroll away, along with shaded benches lining the lagoon and a waterfront green where slow mornings and golden evenings by the water become a way of life. Beyond the community, the white sand of Longboat Key's Gulf beaches is moments away, with the boutiques and dining of St. Armands Circle, downtown Sarasota's culture, and the laid-back charm of Anna Maria Island all within easy reach. Come experience the rare blend of comfort, community, and coastal beauty that makes this villa a place to call home. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**

602 Spanish Drive S Unit 115, Longboat Key

2 Beds ⋅ 2 Baths ⋅ Gulfshore Of Longboat Key SubDv. ⋅ 34228 Zip Code

WELCOME TO PARADISE! This unit epitomizes the perfect beach home. When you step through the front door, you will know that you have entered “House Beautiful”. The blend of colors and furnishings will make you feel that you are home. This home features a nice-sized living room, totally upgraded separate kitchen and dining room, two bathrooms and two bedrooms. This home has 1,052 sq. ft. of living area. This home is located just steps from Sarasota Bay. There are limited views of Sarasota Bay from the Living Room, Dining Room, Kitchen and the second bedroom. It has a new Mini Split A/C, and hot water heater. The roof is vinyl and has a brand new elastomeric coating with a 5 year warranty. This unit also has new skirting and new edging on the roof soffits. Gulfshore of Longboat Key is located on a perfect parcel of land. It has it all – private access to a pristine sand beach on the turquoise waters of the Gulf of Mexico, a marina on Sarasota Bay, large community pool, clubhouse with a commercial kitchen, a well-maintained and managed campus and very reasonable HOA fees. Truly, Gulfshore is a remnant of Old Florida that is just six miles from the world-famous St. Armand’s Circle. Gulfshore does not permit rentals or pets and it is a 55+ community. Please call now for an appointment to view your future home and relax in paradise.

3710 Gulf Of Mexico Drive Unit G20, Longboat Key

2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code

Calling all boaters. If you have ever considered living on Longboat Key in sunny beautiful Florida, now is your chance! This amazing villa is available and ready for you to move to paradise! 711 Spanish Dr. S. is a 2 bedroom/2bath home that has been newly renovated in 2025/2026 and it is beautiful! Entering the home your eyes are immediately drawn upwards to the gorgeous open beam 10’-12’ ceiling over the kitchen and dining area. The kitchen is complete with all new wood cabinets, new stainless top of the line appliances, undermount sink, Quartz counter tops, and an oversized island with a dark blue base which brings in a beautiful pop of color. The open floor plan flows easily with luxury vinyl connecting all the rooms. The dining living combination is airy and bright. The primary bedroom is divided from the Florida room with textured glass pane sliding doors that allow the light in but keep the space quiet and private. Beautifully renovated primary bath is tastefully appointed. The guest bedroom and bath have been updated with the same quality and fine design as the entire villa. The large Florida room houses the stacked washer and dryer in their own space. A stylish glass back door leads to the brick patio perfect for your potted plants and just sitting and enjoying the perfect Florida weather. A newly installed PVC gate secures the common area shared by the adjoining villa. Perfect area for grilling, storage of bikes, beach chairs, paddle boards and more. There is also easy access to the unit's storage room. This is a must see! Make it your new home with all hurricane rated windows and doors, and so much more. This vibrant 55+ community of Spanish Main Yacht Club neighborhood is full of wonderful neighbors, and lots of amenities, shuffleboards, swimming pool, private deeded beach access to the gorgeous Longboat Key beaches and the warm Gulf waters. Fishing, boating and so much more. The expansive 40 slip Marina in the envy of all boaters as the lease is extremely inexpensive to lease, you won’t believe it. Call for details. Close to St Armands Circle and downtown Sarasota makes this location perfect for shopping, dining, theater, botanical gardens, airport and more. All 212 units in Spanish Main Yacht Club are under FEMA regulations, guidelines and stringent adherence to rebuild specifications. All FEMA regulations completed including inspections. Come and enjoy your soft place to land in this world.

711 Spanish Drive S, Longboat Key

2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code

This must-see hidden gem on the north end of Longboat Key offers a quintessential Florida lifestyle. Waterview’s galore as you walk into your newly completed, renovated Florida paradise home, on a deepwater marina and canal, which epitomizes beauty and style. Boat lovers will want the location of this totally turnkey furnished 1,423-square-foot standalone two-bedroom, two-bath home, with your upgraded composite boat dock just 15 feet behind your villa. Completely remodeled, this home provides contemporary classic design features that create an open airy gorgeous living space. All new stainless appliances in 2026, air-conditioner 2025, roof 2019 and more. The open kitchen design with a large island, new quartz countertops, plenty of beautiful new cabinets with roll-out drawers and a contrasting white and gray classic color scheme. Great counter space makes the kitchen ideal for entertaining and enjoying the coastal casual lifestyle. Beautiful porcelain tile flows throughout the home, providing continuity from room to room. An oversized skylight in the great room with retractable shade provides lots of extra natural brightness. The large primary bedroom is complete with a fully refashioned en-suite bath with gorgeous granite countertops and custom-tiled shower. A spacious walk-in closet provides plenty of room for your coastal style wardrobe. The second bath mimics the maintained class and elegance of this home with granite counters and tiled shower. The lanai has been transformed into extra living space with a cozy study and separate office nook. The study is an ideal spot to curl up with a book or just sit privately and watch the beautiful white pelicans float by with dolphins and manatees alongside. This flexplace can also house extra sleepover guests. The double lanai facing the water allows a panoramic view and full access to your large, elevated brick paver patio and dock from floor-to-ceiling, impact-grade patio doors. Go outside to a private oasis that overlooks the wide-open canal, marina and bay views. Sit, dine, entertain or sunbathe while you enjoy the abundant wildlife from the comfort of your patio paradise, or hop in your boat secured to your 5-by-25-foot dock and head out to one of the many Longboat Key restaurants. Some of the best waters to explore in Sarasota for fishing, sandbar enjoyment, kayaking and swimming right in your backyard. You have direct access to the Intracoastal Waterway and a quick boat ride to the Gulf of Mexico. Impact windows and new hurricane-rated doors throughout. The Spanish Main maintenance-free community has a wonderful neighborhood feel with heated pool, deeded beach access, a 40-foot slip marina with social events galore, making every day feel like a vacation as you lounge in the sun poolside and enjoy the sea The deeded beach access is ideal for those numerous beach days and magnificent sunsets. Pet-friendly, maintenance-free, and an active 55-plus community are added benefits for your enjoyment. Only a short drive to fantastic shops and restaurants, including Anna Maria Island, plus cultural events Sarasota and St. Armands Circle have to offer. This villa has been fully renovated in compliance with FEMA standards due to hurricane flooding in 2024.

900 Spanish Drive N, Longboat Key

2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code

Discover Longboat Key waterfront living at its very best at 718 Spanish Dr N, a beautifully updated freestanding villa in the sought-after Spanish Main Yacht Club. This home has been completely renovated to today’s highest standards following Hurricane Ian, delivering a fresh, high-end coastal finish throughout with meticulous craftsmanship and premium materials. Just steps from your door, enjoy private deeded beach access to the powder sands and turquoise color of the Gulf of Mexico — perfect for sunrise walks, beachcombing, or sunset gatherings. Boaters will appreciate the community’s deep-water marina with boat slips priced around $1,200 annually that have direct access to the Intracoastal Waterway, and quick passage to the open Gulf, along with kayak racks and fishing right at hand. Inside, the bright open-concept 2-bedroom, 2-bath villa showcases an elevated, contemporary coastal design. The gourmet kitchen is a true entertainer’s dream, featuring sleek modern cabinetry, elegant stone countertops, a spacious island, and high-end stainless steel appliances. Sunlight pours through the generous windows and sliders, highlighting the beautiful new flooring that flows seamlessly into the living and dining areas. A sun-drenched Florida room/lanai offers flexible space, ideal for a home office, artist studio, or casual living — all overlooking lush tropical landscaping and a peaceful community setting. Both bedrooms are generously sized with ample closet space, while the updated baths feature contemporary fixtures and finishes for a spa-like feel. Additional highlights include a private outdoor shower, a spacious carport for your island toys, and thoughtful storage throughout. This vibrant, friendly 55+ community (can be under 55 to purchase) offers a heated pool, a clubhouse with marina views, shuffleboard courts, and a welcoming social atmosphere. Maintenance-free living, beautifully landscaped grounds, and covered parking complete the carefree Longboat Key lifestyle. Whether you seek a full-time waterfront residence, seasonal escape, or outstanding investment, 718 Spanish Dr N offers turnkey luxury with effortless deeded beach access and marina convenience in one of Longboat Key’s most desirable waterfront enclaves. Minutes to St. Armand's Circle, downtown Sarasota, and Anna Maria Island, yet tucked away in paradise. Don’t miss this rare opportunity to own a freshly renovated gem in Spanish Main Yacht Club — where high-end coastal living meets the best of island boating and beach life!

718 Spanish Drive N, Longboat Key

2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code

1 Block from private beach, completely remodeled 1100 sq ft modernized condo with open concept and lot of windows. Custom kitchen, completely gutted and new insulation and drywall. Custom glass-walls, 3 A/C zones. Villa is in 55 plus community with private beach and marina, clubhouse, shuffle board, in peaceful LongBoat Key.

541 Spanish Drive N, Longboat Key

2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code

Virtually Staged. Welcome to Spanish Main Yacht Club waterfront community and your new home! Light and bright, this stand-alone villa is all new and beautifully updated in 2026. White marble-like large porcelain tile floors that span the entire living area, providing a continuous flow throughout the villa. The new kitchen boasts stainless steel appliances, white quartz countertops, new cabinetry, lighting and more. Attractive updates in the primary en suite bedroom and guest bath as well. A nice added feature is the spacious interior laundry room. Beautiful, lush backyard view with privacy and an extra brick paver side yard and outdoor space. A short stroll to the privately deeded beach entrance to gorgeous Gulf beaches. Two minutes to have your toes in the soft, pearly sand. This is a boater’s paradise with slips available for an extremely inexpensive lease and direct access to Sarasota Bay, the Intracoastal waterway and azure waters of the Gulf. Only a short drive to the fantastic shops, restaurants and cultural events Sarasota and St. Armands Circle have to offer. This is a great investment opportunity and chance to enjoy Longboat Key living. The community is in the build-back stage due to damage from hurricanes in 2024 and is almost complete. All 212 units in Spanish Main are under FEMA requirements, guidelines, and stringent adherence to rebuild specifications and inspections from Town of Longboat Key. This is an opportunity to continue to make this villa your custom home.

554 Spanish Drive S, Longboat Key

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