Displaying: For Sale
Location: Longboat Key
Property Type(s): Condos
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Longboat Key - 247 properties found
1145 GULF OF MEXICO DR #401, LONGBOAT KEY, FL 34228
$1,250,000160 Days on yellowkey MLS ID: A4678330
0 Days Off yellowkey (back on 5/19/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1172 Built: 1980 Tax: $13,294 (2025)Community: Beachplace ICondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$13,294
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Under contract-accepting backup offers. This highly desirable 4th floor corner residence at Beachplace boasts full direct views of the Gulf from almost every room. Renovated in a coastal contemporary style with long plank porcelain tile flooring throughout, the island lifestyle is readily apparent upon entering. The kitchen offers azure water views while meal prepping, stainless steel appliances, breakfast bar, granite counters and a closet pantry. The primary bedroom pampers owners with access to the covered terrace, spacious primary bathroom offering dual vanities and expansive water views. Highlights include impact windows, TWO Parking Spaces, new entry door, updated flooring in the bedrooms and new interior doors. With an excellent rental policy of 1 month minimum/12 times a year, there is healthy income potential - call for more details. Beachplace offers a 24-hour manned guard gate, heated swimming pool & spa, tennis courts, fitness center, clubhouse, on-site management and miles of pristine beach to relax, enjoy and explore. Conveniently located on the south end of Longboat Key just minutes from the fine dining and shopping on St. Armands Circle and a short drive over the bridge to the cultural hub of downtown Sarasota. Your Longboat Life awaits! RENTALS IN PLACE CONVEY WITH SALE.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Ian Addy, Pa (941-961-8850)
2110 HARBOURSIDE DR #536, LONGBOAT KEY, FL 34228
$749,00066 Days on yellowkey MLS ID: A4685244
REDUCED by $50,000 (6.3%) on 05/12/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2031 Built: 1988 Tax: $12,286 (2025)Community: Fairway Bay 3Spa: YesCondo
Taxes:$12,286
Remarks: Under contract-accepting backup offers. Completely reimagined with an uncompromising eye for detail, this furnished, southeast-facing 3-bedroom residence in The Atrium of Fairway Bay offers refined living with sweeping views across the lagoon, mangroves, open bay, and Sarasota skyline beyond. Thoughtfully remodeled with no expense spared, the flexible layout feels both elegant and exceptionally functional. Rich wood floors run throughout the main living areas, grounding the residence in warmth and sophistication while complementing the shimmering water and city views beyond the glass. A curated mix of tile, wood, stone, and carefully selected colors creates a distinctive ambiance throughout. In the living room, a full wall of sliders opens to a covered terrace that invites the outdoors in and captures the tranquil beauty of the surrounding vistas. Recessed lighting, 8-inch crown molding, plantation shutters, custom-built cabinetry, and a dry bar with wine fridge elevate the space with both style and purpose. The kitchen is beautifully tailored for daily living and entertaining alike, featuring a large custom island with cooktop, granite counters, tile backsplash, tray ceiling, Bosch stainless steel appliances, a built-in desk, and an oversized custom pantry that adds rare storage and convenience. The primary suite is a spacious retreat, highlighted by a dramatic corner wall of floor-to-ceiling glass and slider access to the terrace. Its bath is generously sized and beautifully finished with dual vanities, warm wood accents, and a glass walk-in shower with built-in bench. Two additional bedrooms provide flexibility for guests, a home office, or den, complemented by a beautifully updated full bath. Additional features include an in-residence laundry room and a top-tier AC system equipped with ultraviolet germicidal UV light and an Ecobee smart programmable thermostat. Located behind the gates of Bay Isles, The Atrium of Fairway Bay offers a relaxed, amenity-rich lifestyle with two community pools, tennis courts, fitness facilities, beautifully landscaped bayfront walking paths, kayak access, and deeded Gulf beach access through the Bay Isles Beach Club. Residents also enjoy 24-hour gated security, with optional access to Longboat Key Golf & Tennis Country Club memberships and deepwater slips.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Bruce Myer (941-376-5311)
615 DREAM ISLAND PL #210, LONGBOAT KEY, FL 34228
$949,90055 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
Tax Year: 2024
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)
836 EVERGREEN WAY, LONGBOAT KEY, FL 34228
$995,000195 Days on yellowkey MLS ID: A4674750
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2813 Built: 1991Monthly Fee: $1,644 Tax: $4,852 (2025)Community: Cedars East Sec 3Condo
Taxes:$4,852
Remarks: Bay Views! Investor Dream Home! A double condo unit which feels like a single-family home, because it is not attached to anything but sunshine, the bay and dreams! Elevated among the treetops on the bay side of Longboat Key, it features 2 oversized garage spaces, wood floors throughout the first elevated living level, an open great room with a large open kitchen for entertaining, an inviting wood-burning fireplace, screened lanai for bay breezes and a office/den/flex room. Upstairs you will find 2 guest bedrooms which share a full bath and a primary bedroom with a view of Sarasota Bay through a wall of windows and a screened lanai where you can catch the sunset glow over the treetops. The ensuite primary bath features dual sinks and 2 large walk-in closets. Amenities in the premier tennis community include exceptional access to Bay waters, perfect for launching a kayak, fishing and enjoying the tide pools. Enjoy a boardwalk stroll through mangroves and watch the sunrise from a private bayside dock (no boat access). Pool membership comes with home ownership. Tennis, pickleball and fitness center access is available through Cedars East Resort at an annual rate. Update, redesign and make it your home or income opportunity today!
Listing Agent: Eileen Saunders (662-404-0816)
455 LONGBOAT CLUB RD #408, LONGBOAT KEY, FL 34228
$2,399,000159 Days on yellowkey MLS ID: A4678407
0 Days Off yellowkey (back on 5/16/2026)
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2780 Built: 1990 Tax: $19,252 (2025)Community: PierreCondo
Taxes:$19,252
Remarks: Behind the gates of the renowned Longboat Key Club, this stunning residence at The Pierre offers a rare opportunity to enjoy elevated coastal living paired with the ease and sophistication of a true resort lifestyle. Completely renovated by Brista Homes, this 3-bedroom, 3.5-bath condominium is spacious, refined, and thoughtfully curated, with three oversized bedrooms each featuring a private ensuite with natural stone and engineered wood flooring throughout for a relaxed yet refined coastal feel. The sleek modern kitchen by Cucine Ricci showcases clean lines, quartz countertops, and high-end finishes that blend style and function, while tranquil golf course views with glimpses of Sarasota Bay fill the living spaces and the balcony offers additional views of the Gulf of Mexico. With a membership opportunity, the world-class golf, dining, and resort amenities of the Longboat Key Club are just steps away. The Pierre is known for its exceptional service and amenities, including a 24-hour concierge, iconic “P”-shaped waterfront pool, deeded beach access to one of Florida’s most beautiful coastlines, tennis and shuffleboard courts, a fitness center with sauna, a club room with catering kitchen, and three private guest suites for visiting family and friends. Ideally located near St. Armands Circle and downtown Sarasota, this residence offers premier shopping, dining, arts, and culture while preserving the privacy and tranquility of gated island living and the very best of the Longboat Key lifestyle. Furnishings are negotiable.
Listing is courtesy of: BRISTA REALTY LLC (941-373-0500)
Listing Agent: Gina Ursini (941-812-4894)
1925 GULF OF MEXICO DR #G8-302, LONGBOAT KEY, FL 34228
$629,00098 Days on yellowkey MLS ID: A4686871
REDUCED by $20,000 (3.1%) on 05/15/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1257 Built: 1978Monthly Fee: $1,607 Tax: $6,897 (2025)Community: Seaplace ViSpa: YesCondo
Taxes:$6,897
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: Experience the Best of Gulfside Living at Seaplace on Longboat Key! Welcome to this beautifully maintained 2-bedroom, 2-bath residence offering the perfect blend of comfort, style, and coastal charm. This light-filled unit features an updated kitchen with rich wood cabinetry, granite countertops, and ample storage—ideal for both everyday living and entertaining. The spacious primary suite offers a relaxing retreat with generous closet space and an en-suite bath, while the guest bedroom provides comfort and privacy for visitors. Both bathrooms are tastefully updated, and the open-concept living and dining areas flow seamlessly to the screened lanai. Step outside to your private lanai with hurricane impact screening, where you can enjoy tranquil views and refreshing Gulf breezes. The home is further enhanced with hurricane-impact windows, providing peace of mind and energy efficiency. Residents of Seaplace enjoy approximately ½ mile of pristine Gulf beach frontage and an exceptional array of amenities across 42 beautifully landscaped acres. Highlights include two heated swimming pools and spas, Har-Tru tennis courts, scenic walking trails, a fitness center, and a clubhouse with kitchen, library, and sauna. Additional features include a playground, grilling areas, on-site management, and a 24-hour staffed gatehouse. Whether you're seeking a full-time residence, seasonal retreat, or investment opportunity, this property offers a low-maintenance island lifestyle in one of Longboat Key’s most desirable communities. Enjoy breathtaking sunsets, beachside strolls, and resort-style living—schedule your private showing today!
Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
Listing Agent: Michael Renick Pllc (941-400-8735)
4400 EXETER DR #305, LONGBOAT KEY, FL 34228
$324,90063 Days on yellowkey MLS ID: A4691085
0 Days Off yellowkey (back on 5/15/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 837 Built: 1970 Tax: $2,819 (2025)Community: Longboat HarbourSpa: NoCondo
Taxes:$2,819
Remarks: Under contract-accepting backup offers. Welcome to coastal living on coveted Longboat Key. Priced to move, this beautifully maintained 1-bedroom residence at 4400 Exeter Dr Unit 305J offers an exceptional opportunity to own in one of the island’s most desirable waterfront communities. Inside, you’ll find a bright open floor plan with warm wood flooring, an updated kitchen featuring stone countertops, stainless appliances, breakfast bar seating, and abundant custom storage. The spacious living area flows seamlessly to the enclosed lanai where tranquil water and tropical garden views create the perfect setting for morning coffee or evening relaxation. The generous primary suite includes large windows, great natural light, and access to a beautifully updated bath with dual vanities and modern finishes. Enjoy resort-style amenities including waterfront grounds, boat docks, pool, lush landscaping, and close proximity to deeded beach access, golf, tennis, dining, and shopping. Whether you’re seeking a seasonal retreat, investment property, or year-round island lifestyle, this value-priced Longboat Key residence is ready for immediate enjoyment. Opportunities at this price on Longboat Key do not last. Schedule your private showing today.
Listing is courtesy of: SVN COMMERCIAL ADVISORY GROUP (941-387-1200)
Listing Agent: Larry Starr (941-914-6869)
2301 GULF OF MEXICO DR #43N, LONGBOAT KEY, FL 34228
$1,000,000104 Days on yellowkey MLS ID: A4686190
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970 Tax: $10,915 (2025)Community: Islander Club Of LongboatCondo
Taxes:$10,915
Remarks: One or more photo(s) has been virtually staged. Perfectly positioned in the sought-after Islander Club Condominium, this 2-bedroom, 2-bath residence offers commanding Gulf and beach views from the living room, dining room, and both bedrooms. Expansive windows frame the sparkling waters of the Gulf of Mexico, creating a breathtaking backdrop for everyday living while showcasing spectacular sunset skies each evening. Situated front and center on the 4th floor, the residence enjoys one of the most desirable vantage points in the building, elevated enough for panoramic shoreline views yet close enough to feel immersed in the beauty and rhythm of the beach below. Competitively priced, the condominium presents a rare opportunity for the next owner to create their own vision of coastal living. Whether designing a sophisticated modern retreat or a relaxed island escape, the residence offers a blank canvas ready to be transformed to your personal taste and style—truly a chance to make it your own. Residents of the Islander Club enjoy a collection of resort-style amenities including direct access to the pristine Gulf Beach, a beachfront Olympic size swimming pool, tennis courts, fitness center, clubhouse, library, and beautifully landscaped tropical grounds. Located on the coveted south end of Longboat Key, the community offers convenient access to Publix, the world-class shopping and dining of St. Armands Circle as well as the vibrant arts, cultural venues, and waterfront restaurants of downtown Sarasota. Go ahead – Make it your own and have it your way!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Steve Nursey (941-356-7010)
2185 GULF OF MEXICO DR #243, LONGBOAT KEY, FL 34228
$2,300,000398 Days on yellowkey MLS ID: A4651046
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2445 Built: 1996 Tax: $27,759 (2024)Community: Villa Di Lancia Ph 1Spa: YesCondo
Taxes:$27,759
Remarks: Experience the pinnacle of island living in this exquisite 3-bedroom, 3-bath penthouse at Villa di Lancia, a prestigious Gulf-front enclave on Longboat Key. One of only 38 residences in this gated, resort-style community, this rare offering boasts a 195 sq ft balcony with sweeping Gulf views—plus glimpses of Sarasota Bay and the downtown skyline. Meticulously maintained by the original owner and offered turnkey furnished, pride of ownership is evident throughout, and the timeless layout invites your vision for contemporary updates. The views from the main living area and primary suite are simply breathtaking, and there is a large covered portion of the balcony to provide shade if needed. The unit has a natural gas fireplace and cooktop, solid core doors, wood cabinetry and stone counters throughout, and a ceiling height of 9’ 9”. The second bedroom has a walk in closet and ensuite bathroom, plantation shutters, and expansive views across the golf course to Sarasota Bay. The third bedroom is currently used as a den, but could be easily restored to a third bedroom. It also has golf course and bay views. The kitchen is well designed with shaker style cabinetry, granite countertops, a central island with pull out drawers and a planning desk, but there is good potential to expand or reimagine as desired. Villa di Lancia residents enjoy direct beach access, lushly landscaped grounds, a staffed gatehouse, and an impressive suite of amenities: har-tru tennis courts (also striped for pickleball), a fitness center, sauna, resort-style pool, hot tub, and elegant clubhouse for social gatherings. Onsite property management, maintenance, and concierge-level services ensure carefree living. Just minutes from the world-class shopping and dining of St. Armands Circle and the vibrant arts scene of Downtown Sarasota, Villa di Lancia offers the perfect blend of privacy, luxury, and convenience. This unit has one assigned garage parking space which is deep enough to fit two vehicles and a private storage unit. EV charging station on site.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-907-2000)
Listing Agent: Bev Murray (941-724-4995)
2410 HARBOURSIDE DR #142, LONGBOAT KEY, FL 34228
$2,695,000108 Days on yellowkey MLS ID: A4685398
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 3382 Built: 1993 Tax: $26,071 (2025)Community: Marina BaySpa: YesCondo
Taxes:$26,071
Remarks: Positioned on the fourth floor of Marina Bay Building I, this fully renovated bayfront residence offers sweeping views across Sarasota Bay and the Harbourside Golf Course from one of Longboat Key’s most exclusive gated communities. Encompassing more than 3,300 square feet of interior living space, this three-bedroom, three-and-a-half-bath residence blends the scale and privacy of a single-family home with the convenience of condominium living. From the moment you enter, walls of floor-to-ceiling glass sliders and oversized windows frame panoramic water and golf course vistas while filling the home with natural light. The open great-room layout creates a comfortable flow between the living, dining, and entertaining spaces, enhanced by engineered hardwood flooring, crown molding, custom built-ins, tray ceilings, and thoughtfully designed lighting. The chef’s kitchen was completely redesigned in 2024, showcasing custom shaker-style cabinetry, quartzite countertops, and an extended island finished in complementary natural wood. High-end appliances include a Viking induction range, Miele built-in coffee station, wine refrigerator, and reverse-osmosis filtration system. A tile backsplash, pantry storage, and built-in planning desk complete this functional and beautifully designed culinary space. The kitchen connects seamlessly to the casual dining area and adjacent media room, creating an ideal setting for everyday living and entertaining. Additional improvements include two new HVAC systems installed in 2025 and remote-controlled storm shutters on all waterfront openings installed in 2024, offering comfort, efficiency, and peace of mind. The primary suite serves as a private waterfront retreat with direct terrace access and serene bay views. Renovated in 2024, this spacious suite features dual walk-in closets with built-in storage systems, and an updated en-suite bath offering dual vanities, soaking tub, and glass-enclosed shower. Two additional guest suites are positioned on the west side of the residence in a split layout, each with walk-in closets, en-suite baths, and access to a shared terrace for visiting family and guests. Secure under-building parking and elevator access add everyday convenience. Marina Bay is an intimate waterfront community of only 60 residences, located behind the gates of Bay Isles. Residents enjoy 24-hour guard-gated security, on-site management, a fitness center, tennis courts, grilling area, and a heated bayfront swimming pool and spa with a scenic sundeck. Ownership also includes deeded access to the private Bay Isles Beach Club, where residents enjoy Gulf-front pavilions, gated parking, and direct access to the white-sand beaches of Longboat Key. Ideally located on the south end of the island, Marina Bay is just minutes from Harbourside Golf Course, the Longboat Key Club marina, and waterfront dining. St. Armands Circle offers boutique shopping and restaurants nearby, while downtown Sarasota’s theaters, galleries, and cultural venues are only a short drive away. From boating and golf to sunset walks along the Gulf, this residence places the best of Longboat Key and Sarasota living within easy reach.
Listing Agent: Roger Pettingell (941-387-1840)
1095 GULF OF MEXICO DR #102, LONGBOAT KEY, FL 34228
$725,00044 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 is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Rich Polese (941-914-7115)
1000 LONGBOAT CLUB RD #304, LONGBOAT KEY, FL 34228
$874,50071 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)
1000 LONGBOAT CLUB RD #403, LONGBOAT KEY, FL 34228
$974,500143 Days on yellowkey MLS ID: A4680791
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1409 Built: 1972Monthly Fee: $1,565 Tax: $9,673 (2025)Community: Privateer SouthCondo
Taxes:$9,673
Remarks: Experience refined coastal living behind the gates of the Longboat Key Club at Privateer South — a serene waterfront retreat where the Gulf sets the rhythm of each day. This exclusive Longboat Key enclave blends timeless Old Florida charm with resort-style amenities. Residents enjoy access to the Longboat Key Club’s championship golf, tennis, deep-water marina, fine dining, and private beach club, while Privateer South offers intimate beachfront living in a 12-story tower at 1000 Longboat Club Road. This fourth-floor corner residence is a fully renovated two-bedroom, two-bath home that captures the essence of coastal elegance. Floor-to-ceiling windows and sliding glass doors open to wraparound balconies with eastern, southern, and partial Gulf views. Begin your mornings with sunrise over Sarasota Bay and the Intracoastal Waterway, as soft hues of pink and gold fill the open living and dining spaces. By afternoon, enjoy sweeping southern views of powder-white sand and turquoise Gulf waters, accompanied by the gentle sound of waves. The interior renovation reflects modern sophistication and comfort. A sleek galley kitchen with quartz countertops, stainless steel appliances, and custom cabinetry flows seamlessly into the bright living-dining area. Neutral tones, shiplap accents, and high-end finishes create an inviting, light-filled space ideal for entertaining or relaxing. The primary suite features desirable southern exposure and a refreshed en-suite bath with dual vanities and a walk-in shower. The second bedroom offers flexibility as a guest room, office, or private retreat, with the guest bath refreshed as well, in a clean, contemporary style. Daily living feels effortlessly indulgent. From the lobby, take the elevator to the heated Gulf-front pool and spa, complete with lounge seating overlooking the shoreline. Manicured pathways lead to private beach access, where dunes, complimentary chairs and umbrellas, and uncrowded sands create the perfect setting for sunset walks and frequent dolphin and pelican sightings. Residents also enjoy beachside grilling, on-site tennis, and the simple pleasures of Gulf coastal living. Gated security, covered parking, and the low-density South tower — with approximately 62 residences — provide both privacy and a welcoming community atmosphere shared by seasonal and full-time residents alike. Evenings on the balcony are unforgettable, with brilliant sunsets fading into star-filled skies over the Gulf. Inside, the open layout invites relaxed dinners, quiet reading, and peaceful nights accompanied by the sound of the water. This beautifully renovated corner residence offers the perfect balance of comfort, elegance, and breathtaking scenery in one of Florida’s most sought-after barrier island communities.
843 BAYPORT WAY #843, LONGBOAT KEY, FL 34228
$670,00051 Days on yellowkey MLS ID: TB8505224
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1983 Tax: $5,838 (2025)Community: Bayport Bch & Ten Ph FSpa: NoCondo
Taxes:$5,838
Remarks: This exceptionally clean and well maintained 2-bedroom, 2-bath residence in Bayport Beach and Tennis Club is offered turnkey (with a few exclusions), ready for immediate enjoyment. Currently the lowest-priced unit in the community, it also presents a rare opportunity for a new owner to customize and renovate at their own pace—adding personal style while building value. Ideally positioned as a bright and private second-floor end unit with no neighbors above, this home is filled with natural light. Kitchen, dining, living room open design with split bedrooms for privacy. The primary suite features a walk-in closet and a dedicated office niche—perfect for today’s work-from-home lifestyle. Two inviting outdoor living spaces—a private open-air deck and a screened lanai overlooking the tropical gardens—create the perfect setting to relax and unwind. Additional highlights include covered parking, ample guest parking, two private storage areas plus an owner’s closet, and the convenience of an in-unit full-size washer and dryer. Set on 27 acres of beautifully landscaped grounds on Longboat Key, Bayport is a sought-after gulf-to-bay community designed by renowned architect Tim Seibert. Residents enjoy 1,200 feet of deeded private beach access along the Gulf of Mexico. Community amenities are exceptional, including a Junior Olympic-size heated pool—one of the largest on the Key—four Har-Tru tennis courts, a fitness center, fishing pier, and kayak launch. Beach chairs and umbrellas are provided, and a full calendar of seasonal social activities fosters a vibrant yet relaxed coastal lifestyle. Meandering shell pathways and meticulously maintained tropical landscaping complete the serene setting. Experience the best of island living with breathtaking sunrises over the bay, unforgettable sunsets on the beach, and everything in between.
Listing is courtesy of: HOME SOLD REALTY LLC (833-700-2782)
Listing Agent: Camilo Perez (833-700-2782)
4485 GULF OF MEXICO DR #402, LONGBOAT KEY, FL 34228
$745,000189 Days on yellowkey MLS ID: A4675789
REDUCED by $15,000 (2.0%) on 05/12/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1022 Built: 1973Monthly Fee: $1,050 Tax: $4,183 (2024)Community: Arbomar AptsCondo
Taxes:$4,183
Remarks: Experience exceptional beachfront living in this beautiful Gulf-front residence at Arbomar on Longboat Key. Unit 402 is a 2-bedroom, 2-bath condominium offering direct, unobstructed Gulf of Mexico views and immediate beach access, making it the most affordable 2-bedroom, 2-bath opportunity on Longboat Key with true Gulf frontage. The residence features a bright, open layout designed to capture stunning water views and coastal breezes. Significant recent improvements provide exceptional value and peace of mind, including a new roof, new balconies and walkways, updated carports, and new doors and impact-rated windows throughout the community. Inside, the home is move-in ready with a newer AC system and newer appliances, ideal for full-time living, a seasonal retreat, or an income-producing beach getaway. Arbomar offers elevator access, a heated beachfront pool, fitness center, and a welcoming, well-maintained community. All special assessments will be paid in full by the seller at closing, eliminating future capital expense concerns for the buyer. Perfectly positioned on Longboat Key, Arbomar is just minutes from St. Armands Circle, Sarasota’s dining and cultural attractions, and world-class golf—while delivering the rare luxury of direct Gulf views and private beach access at an exceptional value.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Richard Tyson (941-999-1179)
3070 GRAND BAY BLVD #644, LONGBOAT KEY, FL 34228
$799,00066 Days on yellowkey MLS ID: A4690677
1 Days Off yellowkey (back on 5/12/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1329 Built: 1995Monthly Fee: $83 Tax: $6,324 (2025)Community: Grand Bay 6Condo
Taxes:$6,324
Remarks: Under contract-accepting backup offers. Penthouse-Level Condo at Grand Bay – Longboat Key Experience luxury living in this beautifully appointed penthouse-level residence at Grand Bay, located behind the gates of Bay Isles on Longboat Key. This spacious 2-bedroom, 2-bath condo offers an open and airy floor plan with stunning east-to-west exposure, capturing both sunrise and sunset from dual balconies with sweeping views of Sarasota Bay, the city skyline, and the golf course. As a penthouse-level home, it also features an added ceiling height of one foot, enhancing the sense of space and light throughout. Both bedrooms are en-suite, with the primary suite featuring dual closets (including one walk-in) and luxurious marble vanities in the bath. The home showcases elegant bamboo flooring in the main living area, marble tile in the bathrooms, and plush carpet in the bedrooms. Floor-to-ceiling sliding glass doors at both ends of the unit flood the space with natural light. The chef’s kitchen is equipped with a Sub-Zero refrigerator, Blue Pearl granite countertops, a breakfast bar, and an in-kitchen laundry room. Recent upgrades include a new AC system in 2021 and a water heater in 2020. The residence also comes with two deeded parking spaces and a private garage-level storage locker, and it is offered furnished for immediate enjoyment. Grand Bay’s exceptional amenities include 24-hour guard-gated Bay Isles entry, an additional Grand Bay gated entrance, secure coded lobby access, on-site property management, and a pet-friendly environment. Residents enjoy two resort-style pools, a state-of-the-art fitness center, tennis courts, and membership to the Bay Isles Beach Club. There are no current or pending assessments. Enjoy the perfect blend of luxury, privacy, and convenience in one of Longboat Key’s premier waterfront communities.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: Nicole Hammons-Dovgopolyi (941-966-8000)
448 GULF OF MEXICO DR #A205, LONGBOAT KEY, FL 34228
$599,00064 Days on yellowkey MLS ID: A4690875
REDUCED by $30,000 (4.8%) on 05/11/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1306 Built: 1970 Tax: $5,089 (2025)Community: Bay HarbourCondo
Taxes:$5,089
Remarks: Set within an intimate 39-residence waterfront enclave, this Bay Harbour retreat captures the essence of refined island living. Framed by swaying palms and 720 feet of shimmering Sarasota Bay frontage, the community feels like a private tropical sanctuary, where beautiful sunrises paint the sky and waterfowl dive gracefully for fish along the shoreline. Boaters will appreciate the ideal marina location, offering a quick, scenic ride to the Gulf of Mexico. The marina is fully equipped with electrical service, fresh water and a fish-cleaning station, while the seawall provides front-row views of dolphins and playful manatees. A kayak launch adds even more ways to enjoy life on the water. Inside, this spacious two-bedroom, two-bath residence spans 1,300-plus square feet of light-filled living with captivating views of Bay Harbour Marina and Sarasota Bay. Both bedrooms feature walk-in closets, and the kitchen blends style and function with wood cabinetry with glass fronts, stainless-steel appliances, solid-surface countertops and tile flooring throughout. The generous primary suite offers an en-suite bath and a peaceful vantage point overlooking the turquoise bay waters. Offered furnished, the home includes an in-unit washer and dryer, covered assigned parking, ample guest parking and elevator access. Bay Harbour’s amenities elevate the experience with a heated pool, grilling area and first-come boat slips accommodating vessels up to 42 feet. Owners may have one pet. Positioned in south Longboat Key, you’re just 15 minutes from downtown Sarasota, home to upscale shopping, acclaimed dining, galleries, theater, opera, ballet and vibrant arts scene. And for everyday indulgence, you can visit or bike to St. Armands Circle, a beloved destination of boutiques, cafés and coastal charm.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Kathleen Wingate (813-731-3332)
604 SPANISH DR N, LONGBOAT KEY, FL 34228
$465,00094 Days on yellowkey MLS ID: A4687282
0 Days Off yellowkey (back on 5/11/2026)
REDUCED by $30,000 (6.1%) on 04/28/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1357 Built: 1967 Tax: $2,486 (2025)Community: Spanish Main Yacht Club CondoSpa: NoCondo
Taxes:$2,486
Remarks: Longboat Key waterfront lifestyle at its finest is now yours to discover. We are proud to present this stunning, fully renovated waterfront two-bedroom, two-bathroom freestanding villa-arguably a premier location within the Spanish Main Yacht Club. Situated in the middle of the north shore of serene Lake Spanish Main, it provides breathtaking views in every direction. The effortless waterfront views are the star of the show, especially enjoyed from your oversized paver patio-ideally designed for perfect island lounging-but also from nearly every room in the home. The waterfront backyard of this residence is framed by mature Black Olive trees that provide dappled shade while perfectly preserving the bright southern light and glistening water. This "center-of-everything" location is truly unbeatable, offering effortless access to your private deeded beach, the deep-water marina, the community pool, and boat slips. Modern Luxury Meets Coastal Comfort- Inside, a comprehensive renovation features custom tile flooring throughout, immediately setting an elevated, modern tone. The gourmet kitchen is an entertainer's dream, boasting custom cabinetry, designer stone countertops, and new stainless steel appliances centered around a first-class island with updated statement lighting. The open-concept floor plan flows seamlessly from the kitchen into an elegant dining area and a spacious family room, where natural light pours in alongside expansive lake views. Beyond, a sun-drenched Florida room?perfectly suited for an artist's studio and private office?offers southern-facing windows where you can watch the sunlight glisten off the water. Private Retreats-The primary suite is a sanctuary of its own, featuring a walk-in closet, generous proportions, Lake Views and a fully renovated ensuite bath. The guest wing is equally impressive, offering an ample bedroom and a stunningly renovated bathroom with a contemporary walk-in shower. Rounding out this exceptional property are the interior workshop, laundry room, additional storage, outdoor shower and a spacious carport perfectly sized for all your island toys. New Windows installed 2019, 2022 brought a new Roof and AC.
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)
Listing Agent: Jesse Griffin (941-822-6165)
4825 GULF OF MEXICO DR #504, LONGBOAT KEY, FL 34228
$825,00055 Days on yellowkey MLS ID: A4689724
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1393 Built: 1970Monthly Fee: $1,656 Tax: $12,908 (2025)Community: Westchester AptsCondo
Taxes:$12,908
Remarks: Discover coastal living at its finest in this beautifully positioned 2-bedroom, 2-bath condominium on one of Longboat Key’s most sought-after stretches. This residence offers spectacular, breathtaking views from both private lanais—perfect for enjoying sunrise coffee or evening sunsets over the water. Inside, the layout is bright and inviting, with seamless indoor-outdoor flow that maximizes the scenery from multiple vantage points. Whether you’re looking for a full-time residence or a serene getaway, this condo delivers both comfort and location. The community is elevating its appeal with exciting enhancements, including upcoming clubhouse renovations featuring a boutique fitness center, newly refreshed landscaping, and a hot tub addition to the pool deck—creating a true resort-style atmosphere with two heated pools, beach cabanas, car wash station, a tennis and pickleball court, shuffleboard court, kayak rack, outdoor storage and a welcoming grilling convenience behind Club 72. This split plan FURNISHED 5th floor panoramic view, master en-suite unit awaits YOU! Enjoy the best of island living with pristine beaches, nearby dining, and a relaxed yet refined lifestyle—all just moments from your door. R&R IS THE PACE, LBK IS THE PLACE!!!!
Listing Agent: Toni Giliberti (941-284-9208)
4835 GULF OF MEXICO DR #106, LONGBOAT KEY, FL 34228
$749,900139 Days on yellowkey MLS ID: A4677656
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1393 Built: 1970 Tax: $6,331 (2024)Community: Westchester AptsSpa: NoCondo
Taxes:$6,331
Remarks: Waterfront Living on Longboat Key – Direct Gulf Access Experience the best of coastal living on beautiful Longboat Key. This first-floor residence offers effortless access and an unbeatable connection to the water, with direct access to the stunning Gulf of Mexico just steps from your door. Recently updated, the home features brand-new flooring throughout, along with all-new hurricane-impact windows, sliding glass doors, and a hurricane front door—providing peace of mind and modern comfort. Enjoy seamless indoor-outdoor living with easy walk-out access, perfect for morning beach strolls, sunset views, or simply embracing the relaxed Gulf Coast lifestyle. Whether you’re looking for a full-time residence, vacation getaway, or investment opportunity, this property offers exceptional value in a highly sought-after location. Year after year, The Westchester has been considered to be the most sought after location on Gulf of Mexico Drive. This two bedroom, two bath 1,393 sq. ft. condominium holds many family memories, which could now be yours. Experience the beautiful views of the Emerald waters from both lanais. Unit has recently been completely painted. Unit is move-in ready to be enjoyed! Both bathrooms contain generous walk-in closets, with a washer/dryer installed in the guest closet. Come witness Resort Style amenities of two heated pools, beach cabanas, car wash station, a tennis and pickleball court, shuffleboard court, kayak rack, outdoor storage and a welcoming grilling convenience behind Club 72. This split plan, first floor, master en-suite unit awaits your TLC. Kitchen includes side-by-side beverage refrigerators. R&R IS THE PACE, LBK IS THE PLACE!!!!!
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