Location: Longboat Key
Do Not Show Listings
2425 GULF OF MEXICO DR #14E, LONGBOAT KEY, FL 34228
$1,675,000101 Days on yellowkey MLS ID: A4686539
REDUCED by $25,000 (1.5%) on 06/25/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1470 Built: 1973 Tax: $13,728 (2025)Community: Sea Gate ClubSpa: YesCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$13,728
Elementary School: Southside Elementary
High School: Riverview High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Back on the market, buyer's financing fell through. Home inspection already completed and all good, and appraisal from bank already completed with no issues. Amazing and Unobstructed 14th Floor Gulf and Beach Views! This is the perfectly remodeled unit you've been waiting for, with stunning sky views! Open floor plan, tile floors throughout, gorgeous open kitchen, and split bedroom floor plan. Just move right in and enjoy the views and amenities. The building has been completely remodeled. New roof, new windows, new railings, new pool, new storage lockers, updated elevators, new parking lot paving. NO PENDING SPECIAL ASSESSMENTS! Every owner has paid over $130K in the last 5 years to update the building and facilities.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Robert Delaney (941-315-3185)
1965 GULF OF MEXICO DR #G5-103, LONGBOAT KEY, FL 34228
$649,00034 Days on yellowkey MLS ID: A4694695
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 933 Built: 1977Monthly Fee: $1,500 Tax: $3,123 (2025)Community: Seaplace IiiSpa: YesCondo
Taxes:$3,123
High School: Booker High
Remarks: Experience coastal living at its finest in this beautifully updated ground-floor residence at Seaplace on Longboat Key. This 2-bedroom, 2.5-bath condominium in the desirable G5 building offers northwest Gulf views and stunning sunset skies from the screened lanai, just steps from the beach. The bright, open-concept floor plan features a sleek modern kitchen with glossy cabinetry, quartz countertops, stainless steel appliances, and a spacious breakfast bar perfect for entertaining. Floor-to-ceiling mirrors enhance the natural light and create a spacious, contemporary feel throughout the living and dining areas. The primary suite offers a peaceful retreat with an updated en-suite bath, while the guest bedroom provides comfort and privacy for family and visitors. Hurricane-impact sliding glass doors and windows provide peace of mind and energy efficiency. Whether you are seeking a vacation getaway, seasonal retreat, investment property, or full-time residence, this move-in-ready condo checks every box. Seaplace is a gated Gulf-front community situated on 42 beautifully landscaped acres spanning from the Gulf to the Bay. Residents enjoy resort-style amenities including 24-hour guard-gated security, a newly remodeled clubhouse, two heated swimming pools, kiddie pool, two hot tubs, three Har-Tru tennis courts, walking trails, fitness center, and private beach access with beach chairs and umbrellas provided. Conveniently located near the Longboat Key Club, St. Armands Circle, and Sarasota’s dining and cultural attractions. Schedule your private showing today and start enjoying the Longboat Key lifestyle!
Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
Listing Agent: Michael Renick Pllc (941-400-8735)
1925 GULF OF MEXICO DR #G8-302, LONGBOAT KEY, FL 34228
$629,00099 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: $1,467 Tax: $6,897 (2025)Community: Seaplace ViSpa: YesCondo
Taxes:$6,897
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!
2600 HARBOURSIDE DRIVE #R-13, LONGBOAT KEY, FL 34228
$400,000Listed 06/25/2026 10:59AM MLS ID: A4697978
Bed: Bath: 0.0 Built: 1985Monthly Fee: $540 Tax: $3,753 (2025)Community: 7981 Longboat Key Moorings MarinaDock-Rackominium
Taxes:$3,753
Remarks: Stunning Sarasota Bay Views! An easy access slip with the views to go along with the superb amenity package, Slip R-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 80 x 23.5, and a usable beam of 19 feet and extra wide finger pier. This is a desired 'inside the T-head' slip location. The Longboat Key Club Moorings Marina is a World Class deep water marina providing direct access to Sarasota Bay and ICW. Yacht Club membership at the Longboat Key Club Moorings provides members access to the private clubhouse, which is well appointed with TV, conference room, private pool area, outside seating and tables, grill, and bathhouse all in a relaxing atmosphere. Additionally, the Longboat Key Club offers multiple restaurants, world class tennis, pickleball and golf facilities, fitness center, with spa and beach access. The Marina is also located within close proximity to Publix, CVS, and world class shopping at St. Armand's Circle. The longest vessel this slip will accommodate is 75 feet. Beam depends on the vessel type and measure. Membership in the Longboat Key Club is required.
Listing is courtesy of: LBRE LLC (941-383-8383)
Listing Agent: Jennifer Wilson (941-809-7592)
1445 GULF OF MEXICO DR #101, LONGBOAT KEY, FL 34228
$1,180,000119 Days on yellowkey MLS ID: A4684021
REDUCED by $15,000 (1.3%) on 06/25/2026
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2092 Built: 1982 Tax: $11,749 (2025)Community: Players Club IiiSpa: YesCondo
Taxes:$11,749
Remarks: Step into this highly desirable corner residence featuring three bedrooms, three full baths, and an expansive 36’ x 11’ sunroom at The Players Club. You’ll immediately be drawn to the impressive 31-foot balcony, offering sweeping views of the resort-style pool, lush, landscaped grounds, and breathtaking sunsets over the Gulf of Mexico. The outdoor space is perfect for alfresco dining, entertaining friends, or simply enjoying the tranquil Gulf breezes. Inside, the sun-filled kitchen is thoughtfully designed with custom cabinetry and a built-in breakfast table that expands both workspace and storage. It flows seamlessly into the main living and dining areas, creating a warm and open environment for entertaining or daily living. Just off the kitchen, elegant French doors open to a generous multipurpose sunroom that can serve as a home office, reading retreat, casual lounge, or even a fourth bedroom for guests. The owner’s suite provides a private sanctuary with a spa-inspired bathroom featuring a soaking tub, separate glass-enclosed shower, dual vanities, and a spacious walk-in closet. The second bedroom functions as a true secondary master, complete with dual sinks, a full vanity, and a fitted walk-in closet, offering comfort and privacy for family or visitors. A third bedroom adds flexibility for guests, workspace, or hobbies. A unique feature of this residence is the private garage, offering rare security and convenience for residents, plus an additional covered parking space underneath the building for extra guest or secondary vehicle use. Set on 11 acres of beachfront with 560 feet of Gulf frontage, The Players Club offers abundant green space, four Har-Tru tennis courts, a 70-foot heated saltwater pool, spa, fitness center, renovated clubhouse with catering kitchen, outdoor grilling areas, putting green, on-site management, and fully funded reserves. Just minutes from St. Armands Circle, downtown Longboat Key, and Longboat Key Club, with championship golf, premier tennis, and a deep-water marina, this corner residence blends privacy, convenience, and resort-style coastal living. Units with this versatile layout and resort-ready features are highly sought after. Offered partially furnished. Seller is willing to discuss a subsidy on the quarterly condominium fee for reserve increase over the next two years!
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
1425 GULF OF MEXICO DR #408, LONGBOAT KEY, FL 34228
$975,000196 Days on yellowkey MLS ID: A4674194
REDUCED by $25,000 (2.5%) on 06/25/2026
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1707 Built: 1983 Tax: $11,336 (2025)Community: Players Club IvCondo
Taxes:$11,336
Remarks: Step inside and be immediately greeted by stunning, uninterrupted views of the Gulf of Mexico, setting the tone for this exceptional Players Club residence. This home is being sold FURNISHED, you just need to bring your toothbrush. The well-appointed kitchen features generous counter space and *stainless steel appliances*, making meal preparation a delight—especially with your own gulf view backdrop. Continue into the spacious living room, where expansive windows draw in the coastal scenery and lead seamlessly to the covered balcony. It’s the perfect place to unwind, entertain, or simply take in the soothing sound of the waves. The primary suite offers private balcony access, a split bathroom layout, and an oversized walk-in closet. Visitors will appreciate the two spacious guest suites ideally located for optimal privacy and relaxing at the end of the day. The Players Club elevates coastal living with resort-style amenities, including a beautifully updated clubhouse featuring a state-of-the-art fitness center, social and catering spaces, four Har-Tru tennis courts, and a heated saltwater pool and spa. The community is ideally located just a short drive from the dining and boutiques of St. Armands Circle and the vibrant cultural offerings of downtown Sarasota. Additional conveniences include on-site management, and a 24-hour staffed gate, ensuring comfort and peace of mind. This residence blends light-filled interiors, generous living spaces, and world-class amenities—offering an exceptional opportunity to enjoy the best of life on the desired southern end of Longboat Key.
Listing Agent: Mairead Smialek (847-334-4848)
3460 WINDING OAKS DR #38, LONGBOAT KEY, FL 34228
$1,150,00024 Days on yellowkey MLS ID: A4695005
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2608 Built: 1988 Tax: $10,320 (2025)Community: Winding OaksSpa: YesCondo
Taxes:$10,320
Elementary School: None
High School: None
Middle School: None
Remarks: Tucked within Winding Oaks, one of Longboat Key’s most sought-after villa communities, this 3BR/3BA residence offers the scale and comfort of a single-family home paired with the simplicity of maintenance-free living. From the paver drive and walkway to the stepped front entry, the residence creates an inviting first impression before opening into a home defined by volume, light and connection to the outdoors. Step inside and soaring ceilings immediately create a sense of openness, while high-set windows invite natural light to move throughout the living spaces. Tile flooring and soft neutral tones create a clean backdrop that complements the peaceful setting just beyond the glass. Renovated in November 2025, the kitchen has been thoughtfully opened and redesigned into a true centerpiece for gathering and everyday living. A substantial island with seating anchors the space, along with stone countertops, white cabinetry, stainless steel appliances, a range hood, wine refrigerator and tile backsplash. An abundance of windows and an adjoining sitting area create a bright, welcoming space whether hosting guests or enjoying a quiet morning. The dining area transitions naturally into the living room, where cathedral ceilings, a corner fireplace and sliding glass doors connect the interior to the outdoors. Beyond, an expansive screened deck overlooks the community lake and fountain, creating a peaceful setting with multiple areas for dining, relaxing or entertaining. Privacy walls on either side enhance the feeling of seclusion while keeping the water views front and center. The primary suite is spacious and calming, featuring vaulted ceilings, engineered wood floors, a wall of sliding glass doors opening to the deck and a large walk-in closet with extensive built-ins. Also renovated in November 2025, the primary bath offers dual vanities, a walk-in shower, dressing area and separate water closet. Guest accommodations are equally well planned. One bedroom includes an en suite bath and walk-in closet, while another is currently configured as an office space with sliding glass doors opening to a private patio. Updated baths throughout, an in-residence laundry room and a 2-car garage add convenience. Set within the Harbourside golf course community, Winding Oaks offers a serene environment with a gated entrance, community pool and spa, and access to the full range of Bay Isles amenities, including deeded beach access through the private Bay Isles Beach Club.
Listing Agent: Bruce Myer (941-376-5311)
2450 HARBOURSIDE DR #244, LONGBOAT KEY, FL 34228
$2,050,0009 Days on yellowkey MLS ID: A4697202
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 3083 Built: 1990 Tax: $20,065 (2025)Community: Marina BayCondo
Taxes:$20,065
Remarks: Welcome home to this corner 3 bed/3.5 residence with sweeping southeast bay and city views at Marina Bay behind the Bay Isles gates on Longboat Key. This showstopping residence has been recently renovated with designer inspired flooring, fixtures and thoughtful details throughout. The kitchen and dining rooms are positioned to capture direct views of Sarasota Bay while offering every convenience including a full wet bar area with wine refrigeration, custom cabinetry, breakfast bar, cabinet pantry and large laundry room with another closet pantry. The expansive living area features incredible wall space for works of art with natural light from the floor to ceiling sliders surrounding the wraparound screen terrace which frames the city skyline and Sarasota Bay. The primary suite has its own private wing and boasts a large shower with multiple shower heads, floating vanity, designer stone tilework, two large walk-in closets and a peaceful bedroom sanctuary with access to the west terrace and tranquil sunset skies. Both guest bedrooms are ensuite with ample closet space (one walk-in and one built-in) and recently renovated bathrooms. Other highlights include hurricane shutters, plantation shutters, automatic shades in the main living area, an under-building parking space, semi-private elevator and membership to the Bay Isles Beach Club on the Gulf. The Beach Club is a private, gated retreat for Bay Isles residents offering a large outdoor pavilion, tropical cabanas, grills and picnic facilities, private showers and restrooms. Marina Bay is a pet friendly community with on-site management, heated pool & spa, gas grill area, fitness room, tennis and pickleball courts. Located nearby the Longboat Key Club Marina, Publix, CVS, Post Office and minutes from St Armands and the cultural hub of downtown Sarasota. Get ready to start your Longboat Life today!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Ian Addy, Pa (941-961-8850)
510 HARBOR GATE WAY, LONGBOAT KEY, FL 34228
$4,395,000227 Days on yellowkey MLS ID: A4671696
Bed: 4 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 5080 Built: 1996Monthly Fee: $208 Tax: $42,201 (2024)Community: Bay IslesSpa: YesSingle Family
Taxes:$42,201
Tax Year: 2024
Remarks: A Waterfront Work of Art. Experience a one-of-a-kind waterfront residence on Longboat Key — now offered at an exceptional new value. Designed around three interconnected circular "pods," the residence flows like a choreographed dance. There are no awkward hallways, no wasted corners, no spaces that feel like afterthoughts. Curved walls carry throughout every room — even into the garage — creating a cohesive design statement that's genuinely rare in residential construction at any price point. This architectural masterpiece is a sculptural composition of flowing living spaces connected by custom corridors, delivering remarkable privacy, abundant natural light, and seamless indoor–outdoor living. The dramatic Great Room pod showcases soaring wood-paneled ceilings and expansive walls of glass that frame tranquil water views. The circular primary suite is a private retreat featuring a spa-inspired bath with dual showers, a lounge area, private office, and direct access to the pool and spa terrace. At the heart of the home, the striking circular kitchen is both artful and functional, centered around a curved island beneath a two-story ceiling and skylight, with a thoughtfully designed radial appliance layout. Two en-suite guest bedrooms open to private patios, while the fully self-contained Secondary Primary Suite above the impressive 32' x 23' three-car garage offers independent HVAC, a luxury bath with steam shower and sauna, and flexible living space ideal for extended guests or multigenerational living. Outdoors, the property embraces the waterfront lifestyle with protected deep sailboat water, a private dock with a 12,000-pound lift, and a resort-style pool and spa designed for entertaining and relaxation. Located behind the 24-hour guarded gates of Bay Isles, residents also enjoy exclusive access to the Bay Isles Beach Club on the Gulf of Mexico.
Listing Agent: John August (941-320-9795)
230 SANDS POINT RD #3205, LONGBOAT KEY, FL 34228
$996,000263 Days on yellowkey MLS ID: A4667440
REDUCED by $29,000 (2.8%) on 06/25/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 634 Built: 1982 Tax: $9,514 (2025)Community: Inn On The Beach Ph ICondo
Taxes:$9,514
Remarks: Spectacular Gulf and Sunset views are enjoyed from this west facing Junior Suite in Building 3. The direct beach view through the swaying palms perfectly encompasses the resort lifestyle and the vision guests have of tropical landscapes when making reservations. This completely renovated residence is currently in the hotel program and reported healthy income in 2023 and 2024. 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 your Longboat Life today!
2020 HARBOURSIDE DR #457, LONGBOAT KEY, FL 34228
$724,0003 Days on yellowkey MLS ID: A4696667
0 Days Off yellowkey (back on 6/25/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1442 Built: 1984 Tax: $9,366 (2025)Community: Fairway Bay 2 Ph 1Spa: YesCondo
Taxes:$9,366
Remarks: Under contract-accepting backup offers. Located on the 5th-floor penthouse level of Fairway Bay, this corner 2BR/2BA residence offers beautiful views of Sarasota Bay, the downtown skyline, manicured grounds, pool, and mangrove channels. Garage parking, a rare and desirable feature on Longboat Key, adds to the appeal. From the moment you enter, a wall of sliders draws your eye through the living room to the bay beyond. Tile floors run through the main living areas, and the open layout includes a spacious living room with a flexible bump-out area ideal for extra seating, a reading nook, or workspace. The dining area flows to the kitchen, which features a functional layout, breakfast bar, and adjoining eat-in area with sliders opening to the side terrace. The primary suite offers bay views, built-ins, a walk-in closet, direct terrace access, and a bath with dual vanities, separate water closet, and excellent potential for updating. The guest bedroom is comfortable and includes an en suite bath. The corner terrace extends the living space outdoors, offering a peaceful setting from morning light on the water to the evening glow of downtown. One of the true highlights of Bay Isles living is deeded private beach access through the Bay Isles Beach Club, a resident-only Gulf-front retreat with an on-site attendant, covered gathering and picnic areas, restrooms, changing rooms, barbecue grills, volleyball court, and beach accessory storage. Fairway Bay residents also enjoy 24-hour gated security, tennis courts, fitness facilities, walking paths, and the benefits of Bay Isles living. Optional Longboat Key Club memberships offer access, depending on category, to championship golf, Har-Tru tennis, private dining, beach and pool club facilities, spa, fitness center, wellness studio, club events, and marina amenities. Deepwater slips may also be available separately.
3606 FAIR OAKS PL, LONGBOAT KEY, FL 34228
$4,999,00031 Days on yellowkey MLS ID: A4694394
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3842 Built: 2000Monthly Fee: $833 Tax: $29,486 (2025)Community: Queens HarbourSpa: YesSingle Family
Taxes:$29,486
Remarks: Nestled behind the gates of the highly celebrated Bay Isles community, this exceptional five-bedroom waterfront residence at 3606 Fair Oaks Lane offers the perfect blend of luxury, comfort, and peace of mind with an impressive list of recent upgrades and improvements. Designed for effortless coastal living, this beautifully updated home showcases refined interiors, expansive outdoor living spaces, and direct boating access, all within one of Longboat Key’s most sought-after neighborhoods. From the moment you arrive, the home’s meticulous maintenance and thoughtful renovations are immediately apparent. A roof just two years old, hurricane shutters on all windows and doors, and multiple updated mechanical systems provide exceptional value and confidence for years to come. Inside, the residence has been extensively renovated in 2026 with stunning new engineered wood flooring flowing throughout the home, creating a warm and welcoming coastal aesthetic. The spacious floor plan offers five generously sized bedrooms, ideal for accommodating family and guests while maintaining privacy and flexibility for today’s lifestyle needs. The heart of the home is the beautifully refreshed kitchen, complete with brand-new KitchenAid appliances installed in 2026, blending modern functionality with timeless design. Adjacent living and dining areas are filled with natural light and seamlessly connect to the outdoor entertaining spaces, creating an inviting atmosphere perfect for both everyday living and hosting gatherings. Every bathroom in the home was completely renovated in 2026 with stylish finishes and contemporary details that elevate the home’s overall elegance. Extensive system upgrades include three HVAC systems replaced in 2022, 2023, and 2026, along with a new hot water heater installed in 2026, ensuring maximum efficiency and comfort throughout the property. Outdoor living is equally impressive and designed to embrace the Florida waterfront lifestyle. The pool area underwent a significant transformation in 2025 with new pool decking, a resurfaced pool finish, updated waterline tile, and a new gas pool heater, creating a true private resort setting. In 2026, the addition of a fully equipped outdoor kitchen elevated the entertaining experience even further, offering the perfect backdrop for waterfront dining and sunset gatherings. Boating enthusiasts will appreciate the new 10,000-pound boat lift installed in 2025 along with a beautifully updated dock and deck, providing quick and convenient access to Sarasota Bay and the Gulf waters beyond. Combining luxury updates, exceptional outdoor amenities, and a premier location within the coveted Bay Isles community, with private beach club access, this extraordinary Longboat Key residence presents a rare opportunity to enjoy refined waterfront living with every major improvement already completed.
Listing is courtesy of: SARASOTA TRUST REALTY COMPANY (941-366-1619)
Listing Agent: Renee Preininger (941-400-4235)
6750 GULF OF MEXICO DR #163, LONGBOAT KEY, FL 34228
$490,000116 Days on yellowkey MLS ID: A4683547
0 Days Off yellowkey (back on 6/4/2026)
REDUCED by $10,000 (2.0%) on 05/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1449 Built: 1970 Tax: $4,337 (2024)Community: Whitney BeachCondo
Taxes:$4,337
Remarks: Under contract-accepting backup offers. Virtually Staged. Tucked within the intimate Whitney Beach community on Longboat Key's serene north end, this beautifully reimagined two-bedroom, two-bath end unit occupies one of the community's most coveted positions — a corner residence offering protected water views over Bishop's Bayou from both the kitchen and living room, sheltered from the wake and noise of the open Intracoastal. At 1,449 square feet, the thoughtfully renovated interior features quartz countertops, stainless GE appliances, a light coastal palette, and quality finishes that reflect genuine investment in the space. Additional end-unit windows flood every room with natural light and an airy, open feel throughout. The floor plan is equally flexible — two generous bedrooms with en-suite baths, a bright 9-by-14-foot flex space ideal as a home office, sitting room, or overflow guest accommodation, plus dedicated storage. Step outside and the lifestyle unfolds immediately — deeded private beach access to the turquoise Gulf is just a short stroll across Gulf of Mexico Drive, while bayside docks offer the perfect perch for fishing or simply watching the day pass. Whitney Beach delivers the rest with two pools, tennis, barbecue stations, kayak storage and launch, and lush walking paths. Boat slips are available to sublet, and rentals are permitted with a one-month minimum — everything the discerning seasonal owner needs to simply arrive and enjoy.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Karen Whitaker (941-724-6969)
521 BAYPORT WAY #521, LONGBOAT KEY, FL 34228
$619,90012 Days on yellowkey MLS ID: TB8518960
REDUCED by $29,100 (4.5%) on 06/24/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1980Monthly Fee: $1,978 Tax: $5,669 (2025)Community: Bayport Bch & Ten Ph ACondo
Taxes:$5,669
Remarks: BACK ON THE MARKET and offering an exceptional investment opportunity at Bayport Beach & Tennis Club. Unit 521 is PRICED BELOW a recent June 2026 independent appraisal and currently the lowest-priced residence in the Bayport Beach & Tennis Club complex, we feel this beautifully updated condominium represents one of the best values on Longboat Key for a primary residence, seasonal retreat, vacation home, or investment property. Features include impact-resistant windows and sliding glass doors, City-permitted interior remodeling, a newer air conditioning system, covered parking, private storage, and numerous thoughtful upgrades throughout. The recent June 2026 independent appraisal, City permit records, association budget, reserve information, and HOA documents are available electronically upon request. Discover the essence of coastal resort living within Bayport's beautifully landscaped 27-acre Gulf-to-Bay community featuring 1,200 feet of private deeded Gulf of Mexico beachfront, direct Sarasota Bay access with a fishing pier and kayak launch, mature tropical landscaping, scenic walking trails, and an outstanding collection of resort-style amenities. Residents enjoy a heated Junior Olympic lap pool, four Har-Tru tennis courts, fitness center, clubhouse, community room, kayak launch and storage, professional on-site management, and one of Longboat Key's most desirable waterfront lifestyles. Conveniently located just minutes from Publix, Ace Hardware, Pickle ball facilities, waterfront dining, boating, championship golf, St. Armands Circle, The Ringling Museum, dog parks, and the cultural attractions of downtown Sarasota, Bayport offers the perfect balance of island tranquility and everyday convenience. Whether you're searching for a full-time residence, seasonal getaway, vacation home, or long-term investment, this move-in-ready residence offers exceptional value in one of Florida's premier Gulf-to-Bay communities. Experience the relaxed elegance, natural beauty, and resort lifestyle that have made Bayport Beach & Tennis Club one of Longboat Key's most sought-after addresses. Come experience why so many residents say that living at Bayport isn't just owning a home—it's embracing a year-round island resort lifestyle that others only experience on vacation.
Listing is courtesy of: PERSONAL REALTY ADVISERS (727-317-7653)
Listing Agent: Rob Coscia (239-770-2683)
4725 GULF OF MEXICO DR #314, LONGBOAT KEY, FL 34228
$724,900202 Days on yellowkey MLS ID: A4673798
REDUCED by $25,000 (3.3%) on 06/24/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1104 Built: 1974 Tax: $10,125 (2024)Community: Sand CayCondo
Taxes:$10,125
Remarks: Welcome to Sand Cay Beach Resort—one of Longboat Key’s premier vacation destinations. VACATION WHEN YOU WANT - GENERATE INCOME WHEN YOU DON'T - TURNKEY GULF-SIDE INVESTMENT WITH REAL RETURNS. Rarely available third-floor condo truly impresses with soaring vaulted ceilings exclusive to top-floor residences, a beautifully updated kitchen, and tasteful coastal-inspired finishes throughout. A well-established vacation rental with a strong income history, this property is an ideal opportunity for both personal enjoyment and investment. Nestled within an intimate beachfront community offering 340 feet of pristine Gulf frontage, Sand Cay provides an exceptional resort-style experience. Residents and guests enjoy first-class amenities including tennis courts, shuffleboard, a heated pool, basketball area, barbecue stations, a full-time on-site manager, and a convenient in-house rental program. Perfectly located, the resort is just minutes from the boutique shops and fine dining of St. Armands Circle and the vibrant arts and cultural attractions of downtown Sarasota. Light and bright, this third-floor garden-view condo is ideally situated between the pool and the beach. The inviting floor plan features two bedrooms, two bathrooms, a spacious living and dining area, an updated and fully equipped kitchen, a cozy den/office nook, and a private balcony with an awning—ideal for morning coffee or unwinding after a day by the Gulf. Your slice of Longboat Key paradise awaits. Schedule your showing today.
Listing Agent: Michael Albano, Pa (941-993-9571)
2020 HARBOURSIDE DR #417, LONGBOAT KEY, FL 34228
$899,00084 Days on yellowkey MLS ID: A4686674
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1715 Built: 1984 Tax: $6,538 (2025)Community: Fairway Bay 2 Ph 1Spa: YesCondo
Taxes:$6,538
Remarks: A vibrant expression of style and care, this 2BR/2BA corner residence set on the first living level of Fairway Bay offers 1,715 +/- sq. ft. of thoughtfully designed space in one of Longboat Key's most amenity-rich communities behind the gates of Bay Isles. From the moment you step inside, the attention to detail is clear, creating an interior that feels both polished and inviting. Luxury vinyl plank floors establish a warm foundation, complemented by soft sage tones and the natural blues and greens that draw your eye through the living space toward the water beyond. The living room has been expanded to create a more generous gathering space filled with natural light, while additional enclosed space near the kitchen adds flexibility for a private workspace or extended living. The open terrace off the living area offers views across the bay and toward the Sarasota skyline and direct walkdown access to walking trails, a kayak launch, pool, fitness center, and other community amenities, just steps away. The kitchen has been beautifully updated with a charming breakfast bar accented by shiplap, along with stone countertops, all-white cabinetry, stainless steel appliances and a clean tile backsplash. An abundance of storage and a tucked-away workspace add both function and convenience without interrupting the flow. The primary suite is spacious and serene, offering bay views and a thoughtfully redesigned bath with dual vanities, a glass walk-in shower with porcelain tile and epoxy grout. Additional features include plantation shutters and solar blinds, high-impact glass and storm protection on all openings. Residents of Fairway Bay enjoy a full array of amenities, including deeded beach access and a private beach club, 24-hour gated security, pool, tennis and pickleball courts, fitness facilities and all the privileges of Bay Isles living. Optional memberships to the Longboat Key Golf & Tennis Country Club and access to deepwater slips are available. The residence also includes covered parking and accommodates pets up to 15 pounds.
775 LONGBOAT CLUB RD #401, LONGBOAT KEY, FL 34228
$1,595,000117 Days on yellowkey MLS ID: A4681439
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1510 Built: 1984 Tax: $13,823 (2025)Community: Beaches Of Longboat Key Ph-1Spa: YesCondo
Taxes:$13,823
Remarks: Discover Coastal Elegance at The Beaches of Longboat Key! Nestled behind the renowned gated entrance of the Longboat Key Club, The Beaches offers an unparalleled Gulf-front retreat on one of Florida's most exclusive barrier islands. This stunning 4th-floor, 2-bedroom/2-bath residence boasts direct western exposure, delivering breathtaking, forever Gulf of Mexico views and spectacular sunsets that paint the sky in vibrant hues every evening. Step inside to find stylish, move-in-ready finishes, including brand-new porcelain tile flooring throughout the living areas and elegant marble in both bathrooms. The updated kitchen shines with fresh cabinetry, a new GE Profile refrigerator, and dishwasher—perfect for effortless entertaining or quiet evenings at home. The spacious living room and both bedrooms feature impact-resistant sliders that open to a private balcony, seamlessly blending indoor comfort with the soothing sights and sounds of the beach and surf just steps away. Residents enjoy an exceptional array of resort-style amenities: 24-hour concierge service for added security and convenience, Gulfside heated pool and spa, Modern fitness center, Two Har-Tru tennis courts, Social room with a full catering kitchen, Direct beach walkway with complimentary beach chairs (and often umbrellas) provided. Additional perks include two assigned parking spaces in the secure garage and a dedicated storage unit. Priced to impress in this highly sought-after community, this turnkey condo combines modern luxury, prime beachfront access, and the prestige of Longboat Key Club living—without requiring club membership. Opportunities like this rarely last long on Longboat Key. Don't miss your chance to own a slice of paradise—schedule your private showing today!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Larry Brzostek (941-993-3125)
624 SAINT JUDES DR, LONGBOAT KEY, FL 34228
$700,000218 Days on yellowkey MLS ID: A4672840
REDUCED by $49,900 (6.7%) on 06/11/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1387 Built: 1957 Tax: $8,692 (2025)Community: Longboat KeySingle Family
Taxes:$8,692
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
Remarks: You’ve watched, you’ve waited, and now the moment to act is here. The seller is ready to pivot their investment strategy, and they’ve authorized a limited-time price adjustment on this property. Effective immediately, the price has been reduced to $700,000—but this offer is locked in only until next Friday. If this was the home you were waiting for, the hesitation ends today. Let’s get you into your new property before this window closes. The stunning Cali-Modern residence has a new, more attractive price! Presenting an amazing opportunity for this stunning, fully renovated residence where Cali-Modern design meets the tranquil elegance of Longboat Key. Presenting a stunning, fully renovated residence where Cali-Modern design meets the tranquil elegance of Longboat Key. This sophisticated, move-in ready home offers an abundance of good vibes and professional quality, available now on the highly sought-after North End of exclusive Longboat Key. Sleek, chic, and absolutely move-in ready, this property is an instant atmosphere setter. From the moment you step inside, you'll feel the coastal modern bliss. Enjoy the clean, modern lines, vaulted ceilings, and stunning stone tile floors, all bathed in gorgeous southern sun light. The upgraded kitchen and bathrooms sparkle with new features, complemented by new appliances. This home has been lovingly and extensively renovated, offering quality and style that goes well beyond the expected. You will find thoughtful design and premium features in every corner. Step outside to your own private backyard oasis, the perfect spot to sip a sunset cocktail. Fully fenced and private this oasis sets up perfectly for the future pool. And talk about location! You are literally steps from both Gulf and Bay access. This home boasts unbeatable walkability to island favorites like Harry's Deli and The Continental Kitchen, Euphymya Haye and the Hayloft, Lo-Key Island Grille, Cedars East Tennis and Fitness Resort and many others. The best-kept secret? A private back gate leads you directly into the 32 acres of Joan Durante Park, offering pure, natural Florida coastal hammock. This park is a true gem filled with nature walking trails, fishing piers, playground for the kids and multiple Bay access points (perfect for the kayak launch) No fuss, no stress. With a standing seam metal roof, Hardi board siding, newer double-pane windows, New interior, new appliances and offered fully furnished, this charmer is ready for your island life to begin immediately. Don't wait, come feel the charm for yourself!
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)
Listing Agent: Jesse Griffin (941-822-6165)
2326 HARBOUR OAKS DR, LONGBOAT KEY, FL 34228
$800,000122 Days on yellowkey MLS ID: A4683180
REDUCED by $99,000 (11.0%) on 06/19/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2282 Built: 1986Monthly Fee: $143 Tax: $10,215 (2025)Community: Harbour Oaks 2Villa
Taxes:$10,215
Remarks: PRICE IMPROVEMENT – REDUCED $99,000! Discover refined coastal living in this impeccably maintained, fully furnished end-unit villa on Longboat Key, now offered at an exceptional new value following a $99,000 price reduction. Offering nearly 2,400 square feet of thoughtfully designed living space, this residence combines the privacy and feel of a single-family home with the ease of maintenance-free living, all just moments from the Gulf's pristine beaches. Vaulted ceilings, abundant natural light, and an open floor plan create an inviting atmosphere throughout. Multiple living and entertaining areas include a formal living room with a wood-burning fireplace and expansive sliding glass doors leading to a spectacular 740-square-foot private terrace overlooking tranquil pond views. Timeless coastal finishes include rich wood flooring, plantation shutters, granite countertops, updated cabinetry, and a skylight that fills the kitchen with natural light. Recent improvements include a new roof and new air-conditioning system, both completed in 2025. Two private atriums add architectural character and natural beauty, while a versatile office with a built-in Murphy bed can easily serve as a fourth bedroom. The spacious primary suite offers a private retreat, complemented by comfortable guest accommodations. Additional features include a private two-car garage with organized storage, a heated community pool and spa, and exclusive membership to the gated Bay Isles Beach Club with private Gulf-front beach access and dedicated parking. Ideally located near world-class beaches, boating, waterfront dining, and the renowned Longboat Key Club's golf, tennis, pickleball, marina, and dining amenities, this exceptional residence offers the ultimate island lifestyle. Private, elegant, fully furnished, and now priced to sell, this is a rare opportunity to own one of Longboat Key's most desirable villa residences.
Listing Agent: Rachel Tritschler (941-993-5892)
705 JUNGLE QUEEN WAY, LONGBOAT KEY, FL 34228
$2,795,00016 Days on yellowkey MLS ID: A4696488
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3083 Built: 2011 Tax: $38,157 (2025)Community: Shipmans AddSpa: YesSingle Family
Taxes:$38,157
Remarks: Tucked away on the coveted north end of Longboat Key, this custom-designed coastal contemporary residence offers a rare blend of modern architecture, boating access, and waterfront living. Designed by architect Mark Sultana of DSDG, the home was completed in 2011. Positioned along a protected saltwater canal with private dockage and just moments from the Gulf's sandy shoreline, this island retreat captures tranquil water views, tropical surroundings, and spectacular sunsets from multiple levels. Spanning nearly 3,100 square feet, the four-bedroom layout is designed for effortless indoor-outdoor living. The main level serves as the heart of the home, where soaring 18-foot whitewashed cypress ceilings crown the open great room. A contemporary gas fireplace with gray glass tile anchors the living area, while walls of impact-rated glass fill the residence with natural light and frame views of the canal and lush mangroves beyond. The open-concept design seamlessly connects the living room, dining area, and gourmet kitchen, creating an ideal environment for both entertaining and everyday enjoyment. The chef's kitchen is appointed with custom solid-wood cabinetry by Campbell Designs, quartz countertops, glass tile backsplash, breakfast bar, oversized pantry, water filtration, and premium appliances. Thoughtful details such as Lutron lighting system, built-in audio throughout the interior and exterior, impact-rated doors and windows, soft-close drawers, metal barrel roof, propane-fueled pool heater and outdoor grill, oversized two-car garage with workshop, abundant storage, and dedicated kayak storage enhance both function and style. An open staircase crafted from powder-coated aluminum with blonde maple treads creates an architectural focal point while connecting the living spaces. The second level is devoted to private accommodations, including two guest bedrooms sharing a beautifully appointed bath, with one currently configured as a den. The upper floor is highlighted by the primary suite featuring dual walk-in closets, a private waterfront terrace, and spa-inspired bath with freestanding soaking tub, marble-topped dual vanity, oversized glass shower, and separate water closet. Adding exceptional flexibility, a detached cabana suite overlooks the pool deck and serves as a private guest retreat. Complete with a full bath, walk-in closet, morning kitchen, and separate entrance, this space functions perfectly as a fourth bedroom, guest quarters, home office, or artist's studio. Outdoor living is equally impressive. White terrazzo terraces on each floor overlook the 36-foot lap pool and spa with waterfall feature, creating a private tropical setting enhanced extensive landscape lighting, mature exotic foliage, and lush zoysia grass. The private IPE wood dock includes an 8,000-pound lift, kayak launch, water and electric service, and underwater lighting for boating enthusiasts. Located on one of Longboat Key's most desirable stretches, residents enjoy deeded access to the island's pristine Gulf beach just across the street, waterfront dining, marinas, and scenic biking paths. The Longboat Key Club's golf and tennis facilities are nearby, while St. Armands Circle offers boutique shopping and acclaimed restaurants just minutes away. Downtown Sarasota's cultural attractions are easily accessible, creating an exceptional coastal lifestyle that blends privacy, recreation, and convenience.
Listing Agent: Roger Pettingell (941-387-1840)
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