Longboat Key Listings

Some or all of the listings below are provided by the Longboat Key office.
$900,000 (USD)
Active

Osprey Area Single Family Home

Active

21 Bayhead Lane Osprey, FL 34229

3 Bed
2 Baths
2216 sqft
MLS# A4664085
Looking for a home you can fall in love with? The search is over! Once you see this thoughtfully updated, impeccably maintained 3 bedroom, 2 bath home in The Oaks Preserve you will know you have found your home-sweet-home. From the moment you pull up to the pavered driveway, the care taken to maintain this property is evident. Walk past the two-car garage to the pretty, double front doors with leaded glass and step into the light-filled interior. Here you will find everything you need for comfortable Florida living. There is a dedicated home office off the entryway, with plantation shutters and a ceiling fan. The formal dining area features a lovely decorative ceiling, and a beautiful built-in buffet with glass-fronted cabinetry. The great room features another gorgeous piece of built-in furniture; floor to ceiling sliding glass doors connect the screened lanai and this room, making it bright and airy. The open kitchen, with breakfast bar, features beautiful new granite counters, stainless appliances, a chef’s desk, built-in wine and beverage cooler. The adjoining breakfast nook is flooded with natural light that streams through the aquarium window and offers an amazing view over the pool and spa. The master suit is huge and has a sitting area with a built-in window seat and large walk-in closets with glass front storage. The spacious master bedroom has been updated with granite countertops, and features dual sinks, a tub and separate shower and has marble wall accents. The two guest bedrooms are good sized and offer ample closet space. The second bathroom has been tastefully updated with granite counter and marble accents. The 2 car garage, with epoxy floor, is air conditioned with plentiful storage. Situated in the Bishopscourt neighborhood, behind the secure gates of The Oaks Preserve, this beautiful home backs a lush, tropical preserve providing privacy for the sparkling pool and spa. The lanai has two separate areas surrounding the pool. A large, covered area with an outdoor kitchen and ceiling fan, the perfect place for al fresco dining in the shade, and pool and spa area, covered by a cage, allowing for frolicking in the sunshine. Or meet your neighbors for a dip in the Bishopscourt community pool. The Oaks Club amenities include two championship golf courses, an award-winning tennis program, pickle ball and croquet courts, and a state-of-the-art fitness center. With three outstanding restaurants, and a wide variety of social and recreational options, there is no need to look any further than here for the perfect place to enjoy the best of Florida country club living. Club membership is required with homeownership.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Steve Abbe
$899,000 (USD)
Active

Sarasota Area Single Family Home

Active

521 &Amp 523 Ohio Place Sarasota, FL 34236

5 Bed
4 Baths
1589 sqft
MLS# A4668124
Virtual Tour
Picture-Perfect Laurel Park Opportunity! Located in one of Sarasota’s most beloved historic neighborhoods, THIS RARE OFFERING OFFERS NOT ONE - BUT TWO CHARMING HISTORIC COTTAGES set on lush, tree-shaded grounds. Just steps to everything downtown Sarasota and the bayfront - this is Laurel Park living at its best. Step inside the Gold Cottage, where classic bungalow charm meets an open, inviting design. With 2 bedrooms and 1 bath, this light-filled retreat flows seamlessly to a spacious tropical courtyard—a truly special gathering space for morning coffee or evenings under the stars. The Turquoise Cottage welcomes you through its screened front porch, perfect for a good book or card games with friends. Inside, you’ll find 3 bedrooms and 2.5 baths - plus a flexible floor plan with private upstairs access—ideal for guests or rental income opportunities. Together, the two cottages offer a total of 5 bedrooms and 3.5 baths and are offered turnkey furnished, ready to enjoy with family, friends, or tenants. This property offers a unique mix of old and new - with updated baths, appliances and AC's - in a setting that has a vintage charm of yesteryear and tree-lined streets with a true neighborhood vibe. Enjoy the convenience of natural gas, wood floors, open kitchens and separate laundry. A peaceful and tropical lot in this historic neighborhood is a rare find. No HOA, not in a flood zone, no storm damage plus the city rental rules support flexibility - making this property ideal as an investment, full-time home, or seasonal retreat. Live in one cottage and rent the other—or create a multi-generational sanctuary just steps from everything Sarasota has to offer. Walk to shopping, dining, weekly farmers market and cultural events. A great Florida lifestyle!
Listing Courtesy of STELLAR / Coldwell Banker Realty / Monica Verinder
$899,000 (USD)
Active

Longboat Key Area Condominium

Active

1125 Gulf Of Mexico Drive 101 Longboat Key, FL 34228

2 Bed
2 Baths
1172 sqft
MLS# A4672544
Virtual Tour
Step into a bright, inviting coastal retreat just moments from the sand at Beachplace on Longboat Key. This beautifully furnished first-floor residence in Building 3 offers true walk-down convenience from the private wraparound terrace—an effortless way to enjoy the Gulf-front lifestyle. Designed for comfort and ease, the interior features porcelain tile flooring throughout, plus new impact windows and walls of sliders installed in 2021–2022, creating a light-filled setting that feels connected to the outdoors.
The spacious living and dining area is framed by floor-to-ceiling glass, opening directly to the screened lanai with views of the community’s lush landscaping, pool deck, and the Gulf’s sparkling waters. The updated eat-in kitchen includes all-white appliances, LED lighting, Corian countertops, and a convenient breakfast bar pass-through—ideal for casual meals or entertaining.
The private primary suite features wood-grain tile flooring, French-door terrace access, a large closet, and an en-suite bath. A split floor plan ensures comfort for guests, with the second bedroom tucked away for privacy and located next to a well-appointed full bath. Additional conveniences include Turnkey Furnishings and one coveted under-building covered parking space plus an additional assigned outdoor space, a rare benefit in this sought-after Gulf-front community.
Residents of Beachplace enjoy resort-style amenities that enhance the coastal lifestyle. A wonderful Gulf-front community, Beachplace offers 24-hour guard-gated entry, an on-site management team, a stylish clubhouse, fitness center, tennis courts, pickleball, and an expansive Gulf-front deck with heated swimming pool and spa. Walking paths, lush gardens, and direct beach access create a tranquil environment for relaxation.
Perfectly located on the south end of Longboat Key, this residence places you minutes from world-class shopping and dining at St. Armands Circle, renowned golf and tennis clubs, marinas, the cultural venues of downtown Sarasota, and the exceptional beaches that make this area one of Florida’s most desirable coastal destinations.
Whether you're searching for a seasonal escape or a full-time beachfront home, this Beachplace residence delivers impressive value, thoughtful updates, and a premier location along Longboat Key’s pristine shoreline.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Roger Pettingell
$897,000 (USD)
Active

Sarasota Area Land

Active

5510 Merrimac Drive Sarasota, FL 34231

Bed
0 Baths
sqft
MLS# A4642711
Virtual Tour
Exceptional Waterfront Lot in Prime Sarasota Location with designed home ready for you to build. Discover over a quarter acre of prime waterfront at the end of a prestigious cul-de-sac in an established boating community. This 13,500 SF lot boasts an impressive 300 feet of waterfront, offering breathtaking sunrise and sunset views with refreshing cross breezes from the water on both sides of the home.
Located just minutes from the heart of Sarasota, this rare homesite provides easy access to the Gulf beaches, a quick 10-minute boat ride to the Intracoastal Waterway, and close proximity to dozens of waterfront dining options. Top-rated schools, including Pine View, Riverview, and Philippi Shores, are nearby, along with upscale shopping, fine dining, and vibrant cultural attractions. Enjoy the convenience of a short walk to Phillippi Estate Park or a 10-minute bike ride to the beach. This is a unique opportunity to build your dream waterfront retreat in one of Sarasota’s most desirable locations!

ABOUT THE PROPOSED HOME FOR THE SITE:
Luxury Waterfront Estate – New Construction
This exceptional waterfront estate offers up to 6,000 SF of luxury living with over 300 linear feet of waterfront. Enjoy breathtaking sunrise and sunset views from your private balcony and panoramic water views from every room.
Designed for the most discerning buyer, this home features state-of-the-art luxury appliances and finishes, solid concrete construction, and hurricane-resistant design with all impact windows and doors. Smart home automation includes automated lighting and climate control for modern convenience.
The resort-style waterfront pool and spa create the ultimate outdoor oasis, while the rooftop sky deck offers a stunning vantage point for entertaining. A separate 700 SF guest house provides privacy for visitors, and the three enclosed garage spaces ensure ample storage for vehicles and watercraft.
Experience the pinnacle of waterfront luxury in one of Sarasota’s most sought-after locations!
Listing Courtesy of STELLAR / Coldwell Banker Realty / Steve Abbe
$895,000 (USD)
Active

Longboat Key Area Condominium

Active

4235 Gulf Of Mexico Drive T101 Longboat Key, FL 34228

1 Bed
1 Baths
720 sqft
MLS# A4673158
Virtual Tour
Experience effortless beachfront living from this turnkey-furnished, direct Gulf-front retreat at Turtle Crawl Inn on Longboat Key. Positioned on the ground floor, Residence T-101 offers a rare walk-out patio that places you just steps from the turquoise waters of the Gulf of Mexico. It’s the ideal setting for savoring morning coffee with the sound of the surf or unwinding at sunset with uninterrupted shoreline views.

Inside, the professionally designed interior balances coastal comfort with modern updates. Imported contemporary porcelain flooring from Italy flows throughout the open layout. The kitchen features updated cabinetry, stone countertops, white appliances, and a layout that connects seamlessly to the dining and living areas. Impact windows with plantation shutters and impact glass sliders enhance both peace of mind and indoor comfort, while allowing natural light to fill the space.

The spacious bedroom provides ample room for guests, and the updated 2015 bathroom offers clean, timeless finishes. Step outside to your travertine-tiled Gulf-front patio—your own private vantage point overlooking the beach, dunes, and horizon.

Turtle Crawl Inn is known for its relaxed resort experience, offering a wealth of amenities to enjoy or share with rental guests. The community includes a heated swimming pool, beachside cabanas, gas grilling stations, picnic areas, fishing opportunities, and a putting green and shuffleboard courts. Deeded beach access completes the coastal lifestyle.

Located on the mid-island stretch of Longboat Key, this property places you moments from island attractions, waterfront dining, and everyday conveniences. Bayfront Park, Joan M. Durante Park, and multiple marinas are just minutes away for boating and outdoor recreation. Head north to the boutiques and restaurants of Anna Maria Island, or travel south to St. Armands Circle for luxury shopping, cafés, and Sarasota’s renowned arts and cultural venues. Whether used as a personal getaway or as an income-producing rental, this Gulf-front residence combines convenience, comfort, and premier beach access in one exceptional package.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Roger Pettingell
$879,000 (USD)
Active

Longboat Key Area Condominium

Active

1095 Gulf Of Mexico Drive 503 Longboat Key, FL 34228

2 Bed
2 Baths
1503 sqft
MLS# A4648009
Virtual Tour
One or more photo(s) has been virtually staged. Enjoy comfortable, coastal living in this well-appointed 2BR/2BA residence on the sought-after south end of Longboat Key. With over 1,500 sq. ft., this home features a neutral color palette and thoughtful design that enhances the natural beauty just outside. The kitchen offers classic white cabinetry with glass accents, granite countertops, stainless-steel appliances, and recessed lighting. A breakfast bar opens to the dining area, which flows into the spacious living room. Large sliding glass doors lead to the terrace, offering views of Sarasota Bay, the peaceful community lake and fountain, and the Gulf of Mexico - perfect for watching sunsets. The primary suite is light and airy, with terrace access and a full wall of glass. The en suite bath includes dual vanities, a walk-in shower, and a separate water closet. The guest suite also features generous space, plenty of storage, and its own full bath. Beachplace is a 31-acre gated community known for its mid-century modern design by Tim Seibert and its outstanding amenities: private beach access, a Jr. Olympic-sized pool, spa, kiddie pool, clubhouse with social activities, two fitness centers, sauna, tennis and pickleball courts, EV charging, and grilling stations. Rentals are allowed 12 times per year with a 30-day minimum. Residents also enjoy proximity to the prestigious Longboat Key Club, offering an exceptional lifestyle with 45 holes of championship golf, a world-class tennis center, a full-service marina, spa and wellness center, fine dining, and a private beach club - making it easy to enjoy the best of resort-style living just moments from home.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Bruce Myer
$849,000 (USD)
Active

Longboat Key Area Condominium

Active

2301 Gulf Of Mexico Drive 36N Longboat Key, FL 34228

2 Bed
2 Baths
1235 sqft
MLS# A4649187
Virtual Tour
One or more photo(s) has been virtually staged. Front-row Gulf views and beachfront living set this 2BR/2BA residence apart at the Islander Club of Longboat Key. With over 1,235 sq. ft. of light-filled space set just above the sand, savor sweeping vistas of the shoreline and SPECTACULAR SUNSETS over the Gulf. White tile floors and neutral tones throughout create a sense of openness that draws focus to the stunning natural surroundings. A wall of glass sliders in the living room opens to the expansive terrace, where salty breezes and soft waves make every day feel like a vacation. The terrace spans the full width of the residence and can be accessed from both bedrooms, blending indoor and outdoor living in perfect balance. It’s a space with strong potential to match the lifestyle it serves. The primary suite is bathed in natural light, with floor-to-ceiling windows, a walk-in closet and a private bath with a separate water closet. The guest bedroom is equally inviting, with generous space and direct Gulf views. Islander Club is a highly desirable Gulf-front community offering resort-style amenities, including a beachfront pool, tennis courts, a fitness center, library, and billiards room, along with a secure, gated entrance. Conveniently located in the heart of Longboat Key, you're just minutes from St. Armands Circle, downtown Sarasota, and everything the area has to offer. Additionally, while membership to the Longboat Key Club is not required, it is available for residents seeking enhanced amenities. The club offers Restaurants, lounges, beach & poolside facilities, spa, fitness center, tennis courts, and access to 45 holes of championship golf.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Bruce Myer
$849,000 (USD)
Active

Sarasota Area Condominium

Active

800 N Tamiami Trail 321 Sarasota, FL 34236

2 Bed
2 Baths
1734 sqft
MLS# A4675025
Virtual Tour
Welcome to an exciting blend of privacy, space and style in this unique multilevel end-unit townhome with your own private entrance, set within the coveted Alinari at Rosemary Place in downtown Sarasota. Enjoy 1,734 sq. ft. of remodeled interior living space & your very own private 942 sq. ft. Rooftop Deck with sweeping views of Sarasota Bay, Sarasota city skyline, resort-style pool & spa deck, & unforgettable sunsets. 1 of only 6, private townhomes located just off the pool—& the only one currently available—this residence is truly a rare offering. Upon entering at your very own private entrance, cross the threshold & enjoy soaring 18-foot ceilings showcasing ample windows that create an expansive, light-filled interior that seamlessly blends w/the outdoor scenery with high-end finishes, including custom Venetian plaster walls, designer lighting, custom plantation shutters and freshly painted interior. The kitchen is well-appointed with quartz countertops, large bar counter, stainless steel appliances, custom designer soft close cabinetry with ample storage space and an oversized pantry. The adjacent spacious dining area has ample room for 6-8 and flows seamlessly into the living room creating the perfect open-concept floor plan for relaxing and entertaining with friends. The versatile 2nd bedroom/den with an adjacent full bath was previously used as both by the current owner. See images of the custom Murphy Bed with storage. Town records classify unit as a 1BR, but it lives comfortably as a 2BR thanks to the sleek sliding partition door. Open the French doors to a spacious oversized terrace (approx. 642 sq. ft.) which is one of 3 private outdoor spaces. Upstairs, the expansive Primary Suite features its own private balcony, walk-in closet and large en-suite bath with dual sinks, soaking tub, large separate walk-in shower and linen closet. Continue to your very own Private Rooftop Terrace Retreat, which spans the full length of the residence and sets the stage for true luxury overlooking the city skyline and Sarasota Bay making it an inviting space for relaxation, al fresco dining or entertaining. Additional highlights include an oversized laundry room w/built-in cabinetry, retractable screens for airflow throughout, generous storage, two AC units, custom window treatments, upgraded ceiling fans, custom stainless stair railing, beautiful tile floors and two elevators adjacent to the unit. Alinari residents enjoy 24-hour concierge and security with onsite management staff, an 80’ heated lap pool & spa, fitness center, private cinema, outdoor grilling, business center, club room with bar and entertaining kitchen, social and tea rooms, wine cellar with personal locker (a favorite spot for casual wine gatherings), billiards, three guest suites to accommodate additional overnight guests, a large dog park, designated garage parking, a climate controlled storage unit, indoor bicycle storage and an active social committee that plans engaging events throughout the year Alinari residents can rest assured as the building was built at 16’ feet above sea level and is located in an X flood zone and has passed its structural survey with no assessments coming up. Total indoor and outdoor living space: 3,389 sq. ft. all just minutes from Sarasota Bay, Van Wezel, St. Armands Circle, Lido Beach, Sarasota’s vibrant downtown shopping, fine dining, marinas, and expansive arts and cultural offerings.
Listing Courtesy of STELLAR / Coldwell Banker Realty / Tracey Stetler