Location: Longboat Key
Do Not Show Listings
2550 HARBOURSIDE DR #333, LONGBOAT KEY, FL 34228
$1,495,000183 Days on yellowkey MLS ID: A4678404
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 3067 Built: 1990 Tax: $9,185 (2025)Community: Marina BayCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,185
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Set within a living canopy of mangroves and coastal trees, this BAYFRONT residence invites a more immersive relationship with Sarasota Bay—where filtered light, birdsong, and gentle water movement define everyday living. Behind the gates of Bay Isles on Longboat Key, this approximately 3,000-square-foot waterfront residence offers the ease and scale of a single-family home with the security and convenience of condominium living. With three bedrooms and two-and-a-half baths, the layout lives expansively, enhanced by abundant storage and thoughtful separation of living spaces. Floor-to-ceiling glass sliders in the main living areas and primary suite face east, capturing peaceful sunrise light over Sarasota Bay in a setting best described as park-like waterfront—where mature coastal trees frame the water, creating a serene, private “treehouse” ambiance. Boats glide through the mangrove preserve and lagoon toward open bay waters, accompanied by birdsong and rustling leaves. Two balconies extend the living space outdoors, including a nearly 400 sq ft screened lanai ideal for relaxed coastal living. The primary suite features bay views from bed, terrace access, dual walk-in closets, and a spa-like bath with a freestanding soaking tub, dual vanities, and a glass-enclosed shower. The second and third bedrooms share access to a west-facing balcony, offering sunset light and cross-breezes. The kitchen is both functional and social, featuring quartz countertops, a Sub-Zero refrigerator, generous prep space, a built-in desk nook, mini-fridge and wet bar—well suited for entertaining or casual mornings. A dedicated walk-in laundry room adds practicality with a butcher-block workspace, hutch, and tool cubby. Comfort and peace of mind are prioritized with two A/C zones, new condensers (2025), and two hot water tanks (2021) equipped with a flood-stop device. Brand new carpet and paint. Additional highlights include air-conditioned storage, one assigned garage parking space, and exceptional closet capacity—five linen closets, three pantry closets, and three walk-in closets. Residents enjoy on-site management, a fitness center, tennis and pickleball courts, a heated resort-style pool, car washing area, and EV charging stations. The building features a brand-new roof completed in 2025. Pet-friendly. The location is as compelling as the home itself: secure, serene, and walkable. Adjacent to the Longboat Key Club Marina, and just blocks from Publix, CVS, the post office, and banking, this location allows for a genuinely walkable daily rhythm—rare on Longboat Key. As part of Bay Isles, residents also enjoy access to the Bay Isles Beach Club, a private Gulf-front retreat with gated parking, pavilions, grilling areas, restrooms, and seating for sunset views. Deeded beach access ensures a premier spot on the sand. Membership to the nearby Longboat Key Club is available, offering championship golf, world-class tennis, a full-service spa and wellness center, waterfront dining.
Listing is courtesy of: INVESTMENTS IN SARASOTA (941-894-6059)
Listing Agent: Lee Mirman (941-587-0740)
1105 GULF OF MEXICO DR #401, LONGBOAT KEY, FL 34228
$899,000162 Days on yellowkey MLS ID: A4680369
REDUCED by $100,999 (10.1%) on 05/23/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1172 Built: 1981Monthly Fee: $1,600 Tax: $8,733 (2025)Community: Beachplace IiSpa: YesCondo
Taxes:$8,733
Remarks: Direct Ocean view from this Bright Airy corner unit in desirable building five. Catch the view of the Gulf of Mexico and Sunsets from your balcony. To see this property is to fall in love with easy living! You need to visit this unit to get a sense of the remarkable views , especially the amount of light that permeates the entire interior. Beachplace is a perfect get away on the south end of Longboat Key, and comprise many amenities. Pickle Ball, Tennis, two exercise facilities, Olympic pool, with designated lap lanes, over size hot tub , covered baby pool . Electric car chargers, gas grill, two types of workout facilities on almost 31 acres of lush landscaped grounds. Please visit to see why this building and unit are the best of BEACHPLACE!
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: James Weingart (440-623-9068)
4325 GULF OF MEXICO DR #305, LONGBOAT KEY, FL 34228
$999,00086 Days on yellowkey MLS ID: A4690883
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1336 Built: 1975 Tax: $11,669 (2025)Community: Tiffany PlazaCondo
Taxes:$11,669
Remarks: Direct beachfront living! This beautifully updated 2-bedroom, 2-bath residence offers unobstructed Gulf of Mexico views and front-row access to a slice of Longboat Key’s most quiet and uncrowded shoreline. Available fully furnished and turnkey, this condo is ready for immediate enjoyment as a primary residence, seasonal escape, or investment property. The spacious open layout connects the kitchen, dining, and living areas, creating a bright and functional space designed to maximize natural light and water views. The private balcony is the perfect place to spot dolphins, manatees and other wildlife while enjoying morning coffee or evening sunsets. With only 42 residences, Tiffany Plaza offers a more private and welcoming atmosphere than larger condominium communities, with an active clubhouse and strong sense of community among owners. Residents also enjoy close proximity to Bayfront Park, featuring dog parks, tennis, pickleball, kayak facilities, fitness classes, and beautiful bay front walking paths.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Daniel Goldman (516-761-1911)
240 SANDS POINT RD #4104, LONGBOAT KEY, FL 34228
$1,025,00056 Days on yellowkey MLS ID: A4694224
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 640 Built: 1982 Tax: $9,435 (2025)Community: Inn On The Beach Ph IiCondo
Taxes:$9,435
Remarks: Introducing a highly sought-after first-floor Junior Suite in Building 4, boasting stunning Gulf views and now available for purchase. This fully renovated unit is part of the hotel program, generating over $118K in gross income for 2025, with more than $79K already booked through April 2026, indicating the potential for even greater earnings this year. Enjoy an expanded deck alongside a covered terrace that offers direct beach access. Positioned at the northern end of the gulf side, Building 4 provides owners with a sense of privacy from pool activities while still being close to all amenities. As an owner, you gain access to the exclusive offerings of the 410-acre Longboat Key Club, including five fine dining options, 45 holes of championship golf, the award-winning Tennis Gardens, a spa and wellness center, a pristine white sand beach with umbrellas and waitstaff, and a full-service marina. The renovated rooms, main dining area, pool, and guest services enhance the experience at this award-winning property, recognized with accolades such as the AAA Four-Diamond Award and Condé Nast Travelers' Top Florida Resorts. Embrace the Longboat Life today!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Ian Addy, Pa (941-961-8850)
2600 HARBOURSIDE DR #B-13, LONGBOAT KEY, FL 34228
$500,00056 Days on yellowkey MLS ID: A4694623
Bed: Bath: 0.0 Monthly Fee: $675 Tax: $5,375 (2025)Community: Bay IslesDock-Rackominium
Taxes:$5,375
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: A 100 ft. x 28 ft. Boat Slip at Longboat Key Moorings Marina; extra long finger pier, wide beam, extra wide finger pier, and deep water. Huge turning radius, with easy access slip with the views to match the superb amenity package, Slip B-13 at Longboat Key Club Moorings Marina provides one of the most desired locations as a Yacht Club Member slip in the Marina. With the slip measuring 100 x 28, and a usable beam of 25 feet and a long and extra wide finger pier. This location provides close proximity to the hospitality room and Pool. This is a Yacht Club slip. Enjoy all the amenities of the private Longboat Key Club as a Yacht Club Member. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Yacht Club members have access to private Yacht Club facility which includes private clubhouse with TV, conference table, comfortable furnishings just for relaxing. Exterior amenities include private pool, grills, outside tables, chase lounges, and convenient bathhouse. Other amenities include dining at the Key Club's unique restaurants, Islandside and Harbourside golf courses, tennis courts and beach facilities, Fitness Centre, Mind and Motion Studio, and Spa. Longboat Key Moorings is truly a World Class facility. Buyer must join the Longboat Key Club on or before the closing date. Longest vessel this slip will accommodate is 95 feet LOA, with the beam depends on the make of the vessel. All vessels must be approved by the BOD prior to entering the Marina. A current photo and specs of the vessel must be submitted for review.
Listing is courtesy of: LBRE LLC (941-383-8383)
Listing Agent: Jennifer Wilson (941-809-7592)
4825 GULF OF MEXICO DR #202, LONGBOAT KEY, FL 34228
$890,000225 Days on yellowkey MLS ID: A4674248
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1393 Built: 1970 Tax: $11,058 (2024)Community: WestchesterSpa: NoCondo
Taxes:$11,058
Tax Year: 2024
Remarks: The unobstructed Gulf View greets you as you enter this 2nd floor unit. The spacious living area overlooks the large screened lanai out to the Gulf of Mexico. All units at The Westchester community have new impact resistant sliders and windows that meet Miami Dade code in order to reduce insurance premiums for all. This unit also has extra protection as both lanais have electric shutters that also help with energy cost while you are away. The windows, sliders and shutter cost were the responsibility of the owners. Brand new Hunter Douglas honeycomb blinds on both sliders. A/C is 3 years new, water heater 1 year ago. The entire unit is freshly painted and the ceilings refinished. A new GE Profile combo washer/dryer was just installed so you won’t need to use the community laundry. The galley kitchen is tastefully updated with soft close cabinetry and quartz countertops. The refrigerator was replaced 2 years ago; it has a purified water option for drinking water and ice. The primary bedroom has a private lanai that overlooks the Gulf. Both en-suite bedrooms are split to offer privacy. Both have walk in closets as well as a second closet in the main bedroom area. The primary bathroom was renovated with a beautiful shower and dual vanity; The second bath was also renovated and has a large Kohler soaking tub and Kohler fixtures. The guest bedroom is large enough to accommodate 2 double beds. There are 3 entry storage closets as well as a large private storage room downstairs close to your assigned carport space. Westchester is situated on 7 acres with 700 feet of beach. There are loungers on the beach, 2 heated pools, 3 beachside tiki huts, pickleball/tennis court, kayak/bicycle storage, BBQ grills and shuffleboard. The new clubhouse with fitness center is currently under construction. The Gulf side of the property is undergoing improvements to the pool area as well as landscaping. Westchester is a very well managed property with in-house manager and maintenance staff. The unit is being offered unfurnished. BE SURE TO CHECK OUT THE VIRTUAL TOUR LINK FOR THE 3D TOUR - BETTER THAN PICTURES!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Debbie Lane (941-376-9267)
2600 HARBOURSIDE DRIVE #H-04, LONGBOAT KEY, FL 34228
$275,00057 Days on yellowkey MLS ID: A4694327
Bed: Bath: 0.0 Built: 1985Monthly Fee: $37,001 Tax: $2,306 (2025)Community: Bay IslesDock-Rackominium
Taxes:$2,306
Remarks: A favorite dock in the Marina! This 55 x 20 foot slip at Longboat Key Club Moorings is located at the Marina Village along the seawall! Easy access on and off the water to this H-dock slip. Club membership is not required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and discreet, on-site maintenance and concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 50 LOA; beam depends on the vessel. Call to discuss!
240 SANDS POINT RD #4102, LONGBOAT KEY, FL 34228
$950,000317 Days on yellowkey MLS ID: A4663925
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 640 Built: 1982 Tax: $10,451 (2025)Community: Inn On The Beach Ph IiCondo
Taxes:$10,451
Remarks: Highly desirable and rarely available 1st floor walkdown Junior Suite with Gulf views in Building 4 now available. This completely renovated unit is currently in the hotel program and reported healthy income in 2023 and 2024. There is an expanded deck in addition to the covered terrace, which provides direct access to the beach. Building 4 is situated farthest north on the gulf side where owners value privacy from the pool activities, but are still close to all of the amenities. As an owner, you are able to take advantage of the amenities offered by the 410 acre member-only Longboat Key Club while using your owner time. These include fine dining in 5 exclusive restaurants, 45 holes of Championship golf, the award-winning Tennis Gardens, spa/wellness center, white sand beach with umbrellas and waitstaff and a full-service marina. The renovated rooms, main dining area, pool and guest services provide an enhanced product and elevated experience to a property that already accumulates a multitude of awards including the AAA Four-Diamond Award and Condé Nast Travelers Top Florida Resorts. Start enjoying the Longboat Life today!
250 SANDS POINT RD #5106, LONGBOAT KEY, FL 34228
$960,000191 Days on yellowkey MLS ID: A4676698
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 634 Built: 1982 Tax: $7,306 (2025)Community: Inn On The Beach Ph IiCondo
Taxes:$7,306
Remarks: Completely renovated first floor walkdown Junior Suite with spectacular views of Longboat Key Club’s Golf Course currently in the hotel program now available. There is an expanded deck in addition to the covered terrace, ideal for watching a wide variety of wildlife and golfing activity. Building 5 is positioned where owners value privacy from the hustle and bustle of the main entrance and pool activities but are still close enough to enjoy the pool and beach without having to pack the car and drive anywhere. Gross income realized in 2023 was $130,895 and in 2024 was $117,719. As an owner, you are able to take advantage of the amenities offered by the 410 acre member-only Longboat Key Club while using your owner time. These include fine dining in 5 exclusive restaurants, 45 holes of Championship golf, the award-winning Tennis Gardens, spa/wellness center, white sand beach with umbrellas and waitstaff and a full-service marina. The renovated rooms, main dining area, pool and guest services provide an enhanced product and elevated experience to a property that already accumulates a multitude of awards including the AAA Four-Diamond Award and Condé Nast Travelers Top Florida Resorts. Start enjoying the Longboat Life today!
5055 GULF OF MEXICO DR #421, LONGBOAT KEY, FL 34228
$549,000123 Days on yellowkey MLS ID: A4684543
REDUCED by $26,000 (4.5%) on 05/20/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1484 Built: 1973 Tax: $8,224 (2024)Community: Club Longboat Beach & TennisSpa: YesCondo
Taxes:$8,224
Remarks: Set within the highly regarded Club Longboat Beach & Tennis on Longboat Key, this 2BR/2BA residence offers an excellent opportunity to create something truly special in one of the island’s most amenity-rich communities. Just under 1,500 sq. ft. and located on the second level, the residence enjoys a comfortable layout where the primary suite opens to a private terrace, bringing in light and breezes throughout the day. The dining area features a tray ceiling and flows easily into the living room, where a full wall of sliders leads to an open terrace and invites indoor and outdoor living to blend naturally. The space is ready for your personal design vision, offering a solid canvas in a location where lifestyle often takes center stage. Life at Club Longboat Beach & Tennis is known for its mix of recreation, flexibility and beachfront access. Residents enjoy 750 feet of pristine shoreline, eight Har-Tru tennis courts, pickleball courts, two heated pools, a fitness center and a relaxed, social atmosphere. Pet-friendly with 2 pets, no weight restrictions and a rental policy allowing one-month minimum stays up to twelve times per year, this residence is ideal for a full-time escape, seasonal retreat or investment opportunity.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Bruce Myer (941-376-5311)
3710 GULF OF MEXICO DR #G20, LONGBOAT KEY, FL 34228
$349,90061 Days on yellowkey MLS ID: A4693944
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1052 Built: 1991Monthly Fee: $290 Tax: $1,729 (2025)Community: Gulfshore Of Longboat KeyManufactured Home
Taxes:$1,729
Remarks: 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.
Listing is courtesy of: EDGEWATER REAL ESTATE, INC (941-778-8104)
Listing Agent: Bill Shuttleworth (941-779-8877)
615 DREAM ISLAND PL #210, LONGBOAT KEY, FL 34228
$949,90077 Days on yellowkey MLS ID: TB8503989
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1509 Built: 1985 Tax: $11,560 (2024)Community: Harbour Villa Club At The BuccaneerSpa: YesCondo
Taxes:$11,560
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
Remarks: Paradise at Harbour Villa Club – Waterfront Luxury with a boat slip on Longboat Key! Enjoy this condo year round, or rent it weekly when you cannot be there- you choose! Discover this fully renovated 2BR/2BA condo with panoramic views of the gorgeous Sarasota Bay. Bright and spacious, the open floor plan features soaring 9 ft ceilings, custom finishes, a gourmet kitchen with top-of-the-line appliances and a sleek wet bar. The primary suite offers stunning water views, dual closets, and a spa-inspired bath. The second bedroom is spacious and set apart from the primary. Step into the enclosed lanai for breathtaking 180° water views and added living space— perfect for relaxing or entertaining. This unit comes with a deeded 40' boat slip #3 which features upgraded power and plumbing, new wraps, caps, marine grade bumpers and a deck box- a rare bonus that can accommodate a 55' vessel! Harbour Villa Club is nestled in a quiet corner and you can walk or bike to the beach, area restaurants, and beloved Harry's Corner Store. This is a pet friendly community with covered parking, storage, elevators, kayak and bike storage, private dock, heated pool, tennis/pickleball courts, grills and beautiful landscaping. Weekly rentals allowed. Call today!
Listing is courtesy of: CENTURY 21 BILL NYE REALTY (813-782-5506)
Listing Agent: Lori Lahart (813-297-9610)
524 HORNBLOWER LN, LONGBOAT KEY, FL 34228
$2,900,00074 Days on yellowkey MLS ID: A4692210
Bed: 3 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3045 Built: 1964Monthly Fee: $8 Tax: $14,777 (2025)Community: Country Club Shores Sec 2Spa: YesSingle Family
Taxes:$14,777
Remarks: Tucked along one of the most sought-after canals in Country Club Shores, 524 Hornblower Lane is a waterfront residence that fully embodies the Longboat Key lifestyle, where boating access, beach proximity, and refined coastal living intersect with intention. Set on a 0.28-acre canal-front homesite with 107 feet of water frontage, the property offers what experienced boaters immediately recognize as premier water: wide, deep canals with quick, unobstructed access to Sarasota Bay and the Intracoastal. A composite dock, dual boat lifts accommodating vessels up to approximately 38 feet, and a dedicated jet ski lift create a true boating compound, designed for both serious use and effortless enjoyment. Behind its stately, columned façade, the residence spans over 3,000 square feet of living space, thoughtfully updated over time with an effective build year of 2005 and continued improvements, including impact-rated glass, a newer metal roof (2025), and recently replaced mechanical systems. The layout is both functional and flexible, with three bedrooms, three full baths, and a half bath arranged across a two-story design that balances everyday livability with elevated entertaining. The main living areas unfold with a coastal-modern sensibility, wood flooring, crown molding, and expansive sliders that frame views of the pool, lanai, and canal beyond. The kitchen, finished in a soft seafoam palette, blends custom shaker cabinetry, quartz surfaces, and professional-grade KitchenAid appliances with a dedicated beverage station, creating a space that feels equally suited for quiet mornings or hosting at scale. A standout feature of the home is its full entertainment space; an expansive theater and bar lounge designed as a destination in itself. With a projector system, surround sound, custom wet bar, and multiple gathering zones, it introduces a layer of lifestyle rarely found in properties of this scale. A cylindrical tube elevator provides a striking architectural moment while connecting this space directly to the private primary suite above. Upstairs, the primary suite is positioned to take full advantage of the waterfront setting, with a private balcony overlooking the canal, an oversized walk-in closet, and a spa-like bath complete with a jetted soaking tub, dual vanities, and a glass-enclosed shower with dual heads. Outdoors, the experience is equally intentional. A resort-style saltwater pool and spa anchor multiple seating and entertaining areas, complemented by an outdoor kitchen and low-maintenance landscaping that keeps the focus on the water. What elevates 524 Hornblower beyond its physical attributes is its location within the broader context of Longboat Key. Deeded beach access provides a direct connection to the Gulf, while proximity to St. Armand's Circle and the St. Regis Longboat Key Resort places world-class dining, shopping, and amenities just minutes away. The result is a rare dual lifestyle, boating on one side, beach on the other, anchored by one of the island’s most established and desirable neighborhoods. At its core, this is a property defined by access: to water, to the Gulf, to the lifestyle that has long made Longboat Key one of Florida’s most enduring coastal addresses.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
610 HIBISCUS WAY, LONGBOAT KEY, FL 34228
$2,650,00079 Days on yellowkey MLS ID: A4691880
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2788 Built: 2026Monthly Fee: $78 Tax: $5,312 (2024)Community: The Preserve/LongbeachSpa: YesSingle Family
Taxes:$5,312
Remarks: Pre-Construction. To be built. Welcome to a luxurious modern retreat in The Preserve on Longboat Key. This exquisite residence boasts 4 bedrooms and 4.5 bathrooms across 2,788 square feet of impeccable design. Built with Italian flooring, cabinetry, and fixtures, the home exudes a timeless elegance. Enjoy the ultimate privacy and relaxation with a spacious primary bedroom, complemented by a spa-like ensuite. The primary wing extends its allure outdoors with a wrap-around balcony, offering panoramic views of the lush surroundings. The open-concept living spaces seamlessly blend style and functionality, creating an ideal environment for both entertaining and everyday living. The kitchen is a culinary masterpiece, featuring top-of-the-line appliances and sleek design, the sliding glass doors invite natural light to illuminate the interiors, enhancing the overall ambiance. Step outside to a meticulously landscaped yard, where outdoor living spaces beckon for gatherings or peaceful solitude. Enjoy the convenience of being just a short stroll from exceptional restaurants, upscale shopping, and breathtaking sunsets. Experience the sophisticated yet relaxed lifestyle that comes with being a resident of the North Village on Longboat Key.
Listing Agent: Rinat Sikdar (941-993-9292)
667 EL CENTRO, LONGBOAT KEY, FL 34228
$380,000311 Days on yellowkey MLS ID: A4664572
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1327 Built: 1969Monthly Fee: $1,340 Tax: $6,206 (2024)Community: Spanish Main Yacht Club CondoVilla
Taxes:$6,206
Remarks: New photos coming on this beautifully updated free-standing villa in Spanish Main Yacht Club on Longboat Key, a warm and vital boating community with private beach access, pool, clubhouse and boat slips. The community is undergoing a renaissance of sorts as many units (including this one) did have water intrusion in the summer storms of 2024. This owner contracted with the community contractor. has paid related assessment and work is nearly completed! This unit has a bright open floor plan and hurricane windows. Main living area has tile flooring and both bedrooms will have new carpet. There are two bonus areas, one is adjacent to the primary bedroom and could be a private reading area or office and the other adjoins the great room. Once completed, this unit will have two new baths, new appliances, kitchen updated, new doors and new paint throughout. This villa is on the corner and has a much-desired additional parking pad, giving as many as four parking spaces depending on car size. The laundry room, typical of Florida, is in a separate room under the carport. Longboat Key is paradise. A barrier island off Sarasota, where you can find wonderful restaurants, community tennis facilities, parks, bike lanes and a short drive to Sarasota and Anna Maria Island.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Holly Switow (941-735-3186)
718 SPANISH DR N, LONGBOAT KEY, FL 34228
$435,000112 Days on yellowkey MLS ID: A4687749
REDUCED by $14,500 (3.2%) on 05/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1327 Built: 1969 Tax: $2,539 (2025)Community: Spanish MainVilla
Taxes:$2,539
Remarks: 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!
Listing is courtesy of: SARASOTA REAL ESTATE GROUP (941-922-8400)
Listing Agent: John Woodward (941-922-8400)
2600 HARBOURSIDE DR #O-11, LONGBOAT KEY, FL 34228
$239,000430 Days on yellowkey MLS ID: A4652529
REDUCED by $11,000 (4.4%) on 05/13/2026
Bed: Bath: 0.0 Built: 1985Monthly Fee: $302 Tax: $2,725 (2025)Community: Longboat Key Club MooringsDock-Rackominium
Taxes:$2,725
Remarks: Easy Access for Docking your Boat! A 45 ft. x 22.5 ft. Boat Slip on the north side of O-dock pier at Longboat Key Moorings Marina. This slip requires Club membership. Unique set up inside the T-dock. Lots of space, and privacy. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Yacht Club members have access to private Yacht Club facility which includes private clubhouse with TV, conference table, exquisite comfortable furnishings just for relaxing. Exterior amenities include private pool, grill, outside tables, chase lounges, and bathhouse. Other amenities include dining at the Key Club's unique restaurants, Islandside and Harbourside golf courses, tennis courts and beach facilities, Fitness Centre, Mind and Motion Studio, and Spa. Longboat Key Moorings is truly a World Class facility. Excellent sailboat water, easy in and out at the inside of the T-dock, with a wide finger pier too. Longest boat permitted in the slip is 40 feet. Beam depends on the boat model. Call to discuss.
1095 GULF OF MEXICO DR #102, LONGBOAT KEY, FL 34228
$725,00066 Days on yellowkey MLS ID: A4693425
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1392 Built: 1981 Tax: $9,531 (2025)Community: Beachplace IiSpa: YesCondo
Taxes:$9,531
Remarks: A rare private walk-down residence in the highly sought-after Beachplace community on Longboat Key. This property offers the convenience of direct terrace access to the beautifully landscaped grounds below, overlooking a serene pond with fountains and offering a charming peekaboo view of the Gulf. Spacious and largely original, presenting the perfect canvas for a buyer to customize and create their ideal coastal retreat while enjoying the exceptional location and layout. The light-filled interior features an open living and dining area with walls of glass that connect seamlessly to the outdoor living space, creating an inviting indoor-outdoor lifestyle just moments from the beach. The split-bedroom floor plan offers privacy and functionality, while the terrace provides a peaceful setting to relax and enjoy the lush tropical surroundings. Whether updating immediately or renovating over time, this residence offers tremendous potential within one of Longboat Key’s premier Gulf-front communities. Beachplace is renowned for its resort-style amenities and beautifully maintained grounds. Residents enjoy 24-hour guard-gated entry, on-site management, a clubhouse, fitness center, tennis and pickleball courts, heated swimming pool and spa, private beach access, walking paths, and expansive tropical landscaping throughout the community. Ideally positioned on the south end of Longboat Key, Beachplace is just minutes from the fine dining, boutiques, and waterfront charm of St. Armands Circle, as well as downtown Sarasota’s cultural attractions, marinas, golf clubs, and world-class beaches. Whether you are searching for a seasonal getaway, investment opportunity, or full-time coastal residence, this property presents exceptional value and the opportunity to create a personalized beachfront retreat in one of Longboat Key’s most desirable locations.
Listing Agent: Rich Polese (941-914-7115)
1918 HARBOURSIDE DR #902, LONGBOAT KEY, FL 34228
$1,299,000155 Days on yellowkey MLS ID: A4680710
2 Days Off yellowkey (back on 5/12/2026)
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1748 Built: 1982Monthly Fee: $146 Tax: $11,598 (2025)Community: Fairway Bay 1Spa: YesTownhouse
Taxes:$11,598
Remarks: Under contract-accepting backup offers. Welcome to a masterfully reimagined two-bedroom, 2.5-bath FURNISHED town home offering breathtaking, full open views of Sarasota Bay and the vibrant city skyline with its OWN PRIVATE BOAT SLIP. Arguably the most exquisite residence in the esteemed Fairway Bay community at Bay Isles on Longboat Key. The property underwent a meticulous down-to-the-studs renovation in 2020 that included filling in the 100 square foot atrium on the second floor, blending high-end craftsmanship with its unparalleled waterfront setting. The interior is a showcase of custom artistry, featuring warm wood ceilings, solid White Oak stairway treads, an elegant custom iron stairway railing, inset cabinets, Sonos sound system and a Lutron smart lighting system for effortless ambiance control. The gourmet kitchen is a chef’s dream, anchored by a custom White Oak island with quartz tops, Fisher Paykel built-in appliances, and charming built-in banquet seating breakfast niche. Sophisticated touches continue throughout, including a custom iron wine rack, grass wallpaper, designer light fixtures and sleek tile flooring in every room. Retreat to the primary suite, where soaring wood ceilings and a custom walk-in closet provide a sanctuary of comfort. The bath is light, bright and features a furniture-quality inset vanity and an enclosed wet room complete with a standalone soaking tub. The other bedroom on the second floor also has an en-suite bath that features furniture-quality vanity and beautiful walk-in shower. The second-floor laundry with full size LG front-loaded machines makes doing laundry a breeze. For ultimate peace of mind, the home features an impact-rated bayfront living room window and rear exterior door, complemented by a Garrison Hammerhead Aluminum Flood Barrier System installed in 2025. This system includes reinforced cement pilings just inside the garage door with easy-to-use slide-in aluminum slats designed to prevent water intrusion. As part of the Bay Isles community, residents enjoy world-class amenities including 24-hour gated security, swimming pools, tennis and pickleball courts, and exclusive access to the private Bay Isles Beach Club. Just minutes from the cultural heart of downtown Sarasota and upscale shopping of St. Armands Circle, this home offers a lifestyle of effortless elegance.
Listing Agent: Liz Nason (941-350-2243)
1000 LONGBOAT CLUB RD #304, LONGBOAT KEY, FL 34228
$874,50093 Days on yellowkey MLS ID: A4689434
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1409 Built: 1972 Tax: $3,950 (2025)Community: Privateer SouthCondo
Taxes:$3,950
Middle School: Brookside Middle
Remarks: Experience elevated coastal living in this beautifully renovated two-bedroom, two-bath golf-front condominium, ideally situated behind the gates of the prestigious Longboat Key Club in the sought-after community of Privateer South on Longboat Key. Thoughtfully redesigned with a refined coastal aesthetic, this residence showcases a seamless blend of modern elegance and relaxed waterfront living. From the moment you enter, you are welcomed by an open-concept layout filled with natural light, enhanced by expansive windows and tranquil golf course views. The fully updated kitchen features sleek cabinetry, premium finishes, and a clean, contemporary design that flows effortlessly into the spacious living and dining areas—ideal for entertaining guests or enjoying quiet evenings at home. Every detail has been carefully curated to provide both style and functionality. The primary suite offers a serene retreat, complete with a beautifully appointed en-suite bath and generous closet space, while the guest bedroom and bath provide comfort and privacy for visitors. Both bathrooms have been tastefully renovated with modern fixtures and finishes, creating a spa-like atmosphere throughout the home. Residents of Privateer South enjoy a true resort-style lifestyle with an impressive array of amenities. Relax by the sparkling beachfront pool overlooking the Gulf of Mexico, maintain your wellness routine in the fully equipped fitness center, or gather with neighbors in the inviting social room. On-site management ensures ease of ownership and peace of mind. Perfectly positioned between the Gulf and Sarasota Bay, this exceptional property offers convenient access to world-class dining, shopping, and cultural attractions, all while being tucked away in a secure, gated enclave. Whether you are seeking a full-time residence or a luxurious seasonal retreat, this golf-front condominium delivers the very best of Longboat Key living.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Judy Kepecz-Hays (941-587-1700)
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