Location: Longboat Key
Do Not Show Listings
729 SAINT JUDES DR S #3, LONGBOAT KEY, FL 34228
$449,00076 Days on yellowkey MLS ID: A4685189
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 630 Built: 1966 Tax: $1,994 (2025)Community: Saint Judes AptsSpa: NoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,994
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2025
Middle School: Martha B. King Middle
Remarks: Live that Longboat Key waterfront lifestyle and have your own boat lift without the multi-million dollar price. Cute and conveniently located, this on-grade one bedroom condominium unit that is located on a saltwater canal on Longboat Key, features its own 10,000 lb boat lift, and is one block to the gulf beaches and adjacent to Durante Park. Everything new in 2025, including a washer and dryer and hot water demand unit. The condo is completely furnished with an updated living space, complete with open kitchen that features granite countertops, stainless steel appliance and plenty of storage. The modern wood-look tile and updated sliders and windows make for an open feeling living area. There is a paver patio and dock behind the condo for enjoying the sunsets on the canal. A number of shops and restaurants within walking distance. Schedule your showing today!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Steven Schield (941-650-1010)
2089 GULF OF MEXICO DR #G1-108, LONGBOAT KEY, FL 34228
$675,00094 Days on yellowkey MLS ID: A4683552
REDUCED by $24,000 (3.4%) on 04/08/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 933 Built: 1974Monthly Fee: $1,250 Tax: $6,817 (2025)Community: Seaplace ICondo
Taxes:$6,817
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to G1-108, a recently remodeled and fully-furnished residence in Seaplace! Overlooking the pristine sands and sunsets of the Gulf, this first-floor 2 bedroom/2 bathroom residence offers unparalleled access to the beach and resort-style amenities. In early 2025, this residence was extensively remodeled, including impact-resistant hurricane door, new bathrooms and a new kitchen with stainless steel appliances and modern cabinetry. The master suite is a cozy, spacious retreat with a walk-in closet and bathroom. The second bedroom is the perfect space for family and guests, featuring 2 twin beds and a full bathroom. The home also features a new lanai, a comfortable place to relax and soak in the views. Sliding door and all windows are hurricane impact rated. Complimentary with the residence is one parking spot and a designated storage space - perfect for storing any extra beach gear. This residence is being offered furnished. Seaplace is a premier, 24-hour gated and guarded community on Longboat Key. The community boasts 2 swimming pools and hot tubs, a clubhouse and fitness center, fire pit, playground, grilling station, outdoor showers and three Har-Tru tennis courts. Perhaps the most stand-out amenity of this community is its direct beach access already set with lounge chairs and umbrellas. All you have to bring is yourself, your sunscreen and your towel! Going to the beach could not get any easier. Just a short distance from grocery shopping, local boutiques and first-class restaurants and entertainment, G1-108 is perfectly situated to give you that beachfront lifestyle you’ve been looking for. Everything that Longboat Key, St. Armand’s Circle, Anna Maria Island and Downtown Sarasota have in store is at your fingertips. Whether as your primary residence, second home or investment opportunity, G1-108 cannot be missed!
Listing is courtesy of: COLDWELL BANKER REALTY (941-739-6777)
Listing Agent: David Denardo (203-321-9109)
1561 GULF OF MEXICO DR #304, LONGBOAT KEY, FL 34228
$13,000,00077 Days on yellowkey MLS ID: A4685495
Bed: 3 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4891 Built: 2024 Tax: $94,589 (2025)Community: St. Regis Longboat KeySpa: NoCondo
Taxes:$94,589
Elementary School: Southside Elementary
High School: Sarasota High
Middle School: Booker Middle
Remarks: Experience the pinnacle of coastal luxury in the highly sought-after Armand building at The St. Regis Longboat Key, where breathtaking Gulf of Mexico views set the stage for an extraordinary living experience. This residence is absolutely breathtaking and is a must see. Designed for both grand entertaining and effortless everyday living, the expansive great room showcases a sophisticated wet bar and wine refrigerator, all enhanced by striking designer light fixtures and elegant sheers that create a soft, ethereal ambiance. Accordion glass doors seamlessly extend the space onto a sprawling wraparound terrace—complete with a private gas grill and unforgettable sunset vistas. Thoughtfully designed, this gracious room transitions beautifully between formal gatherings and relaxed coastal living. The chef’s kitchen is a true centerpiece, featuring premium Poggenpohl cabinetry, a Sub-Zero refrigerator, Wolf double ovens and gas cooktop, dual dishwashers, and a separate breakfast area with bar and microwave. A large island offers additional seating, making it as functional as it is elegant. Or just order room service! The owner’s suite is a private sanctuary, offering stunning Gulf views and a wet bar perfect for morning coffee or evening unwinding. Dual spa-inspired bathrooms provide two luxurious and private retreats—one with custom closets, an oversized vanity, seamless glass shower, and private water closet; the other with a large vanity, dedicated makeup area, custom closets, seamless shower, and private water closet. A spacious and comfortable club room creates an additional venue for entertaining, complete with a wet bar and beverage refrigerator. Two additional guest bedrooms are equally well-appointed, each opening onto a private terrace. One offers Gulf views, custom closets, and a luxurious bath with a large vanity, makeup area, seamless glass shower, and private water closet. The third bedroom is thoughtfully designed for comfort and privacy, featuring accordion doors to the terrace and a beautifully finished bathroom with a large vanity and makeup area, freestanding soaking tub, seamless glass shower, and private water closet. An elegant powder room adds convenience for guests. Additional highlights include a large laundry room with sink, built-in cabinetry, and hanging rack. The residence is offered fully turnkey, with exquisite furnishings curated by the renowned Marc-Michaels Interior Design—featuring designer-selected finishes, statement lighting, refined furniture pieces, and custom window treatments that create a cohesive, sophisticated aesthetic throughout. Modern living is elevated by fully integrated smart home technology, including iPad-controlled systems, electronic sheers, and blackout shades—delivering both convenience and ambiance at the touch of a button. Nestled within the first branded residential community and ultra-luxe 5 star resort on the Gulf of Mexico. The Residences at The St. Regis Longboat Key blend legendary service with the allure of a seaside getaway. Spanning over 17 acres with 800 feet of direct beachfront, this community offers unparalleled amenities, including the signature St. Regis Butler and Concierge services, a world-renowned St. Regis Spa, in residence dining. Resident only amenities include a clubhouse, fitness center, pool/spa and beach area. Enjoy your private resident only amenities, while having access to all the resort has to offer. Live like you are on vacation all year round!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Lynn Morris, Pllc (941-400-4526)
4401 GULF OF MEXICO DR #601, LONGBOAT KEY, FL 34228
$995,000116 Days on yellowkey MLS ID: A4679728
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1524 Built: 1972 Tax: $14,214 (2024)Community: Longboat Harbour TowersCondo
Taxes:$14,214
Tax Year: 2024
Remarks: Two-bedroom, two-bath residence offering sweeping sixth-floor views of the Gulf of Mexico from Longboat Harbor Towers. This rare southwest corner condominium has completely unobstructed views west and south providing one of the most interesting and protected waterfront visages available anywhere on the key. In largely original condition, this spacious property presents an exceptional opportunity for renovation and customization in one of Longboat Key’s most coveted waterfront locations. Few properties combine this level of potential with such a remarkable setting. Positioned directly on the Gulf with more than 400 feet of pristine beach frontage, this fully amenitized community also enjoys eastern views of Sarasota Bay and the downtown Sarasota skyline—delivering breathtaking sunrises and sunsets from the same home. The southwest exposure also provides much more to view and enjoy with site lines extending down the entire length of the key. Common areas have been recently renovated and include a beachfront, heated, saltwater pool, a complete exercise room and spacious lounge with pool baths. Longboat Key is a sought-after barrier island community known for its relaxed coastal lifestyle, pristine beaches, and upscale residential atmosphere. Ideally located just minutes from the cultural and social energy of Sarasota, residents enjoy convenient access to world-class arts, dining, and entertainment while maintaining a sense of privacy and tranquility. A short drive south leads to iconic St. Armands Circle, renowned for its eclectic mix of boutiques, fine dining, cafés, and year-round events. Beyond St. Armands, downtown Sarasota offers theaters, galleries, live music, waterfront parks, and a thriving culinary scene, making Longboat Key an exceptional blend of island serenity and vibrant city living. This seller also has a BOAT SLIP for sale at The Boathouse, adjacent to the Dry Dock Restaurant just minutes away. Buy the condo and the slip for a complete Florida lifestyle!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: David Jennings (941-650-7354)
415 L AMBIANCE DR #A301, LONGBOAT KEY, FL 34228
$6,100,00054 Days on yellowkey MLS ID: A4688759
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3380 Built: 1992 Tax: $46,418 (2025)Community: L Ambiance 1Spa: YesCondo
Taxes:$46,418
Remarks: Rare corner Gulf-front residence with expansive wraparound terrace and views. An exceptional residence in L’Ambiance, where sweeping water views and refined coastal design converge. This light-filled corner home is defined by an expansive wraparound terrace, offering multiple seating areas and uninterrupted vistas of the Gulf - creating a seamless connection between indoor and outdoor living. Walls of glass frame the horizon from the main living spaces, enhanced by high-impact glass throughout, where generous scale and an open layout provide an effortless setting for both intimate living and entertaining. The kitchen is thoughtfully designed with extensive custom cabinetry, stone surfaces, and a functional layout complemented by a dedicated dining area. A private split-bedroom plan enhances comfort and separation, while a flexible den or media room offers additional space for guests or a home office. Throughout the residence, polished flooring and plantation shutters add a layer of understated sophistication. This residence includes two garage parking spaces, a private wine locker, and additional storage, offering both convenience and security. L’Ambiance offers a boutique beachfront setting with concierge service, a well-appointed fitness center, three guest suites for visiting family and friends, two Har-Tru tennis courts, and an expansive resort-style pool and spa set within beautifully maintained tropical grounds, all with direct beach access. Ideally positioned on the south end of Longboat Key and adjacent to the Longboat Key Club, with optional membership offering access to championship golf, tennis, marina, dining, and a full-service spa, this is a rare opportunity to experience elevated beachfront living.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Bruce Myer (941-376-5311)
1211 GULF OF MEXICO DR #709, LONGBOAT KEY, FL 34228
$1,749,00051 Days on yellowkey MLS ID: A4686985
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1827 Built: 1985 Tax: $14,725 (2025)Community: PromenadeSpa: YesCondo
Taxes:$14,725
Remarks: Set on the 7th floor of the Promenade on Longboat Key, this 2BR/2BA residence offers more than 1,800 square feet of living space with sweeping sunset views across the Gulf, stretching to Sarasota Bay and beyond. From the moment you step into the private entry foyer, the home opens to a light-filled interior where water and sky are always in view. Neutral tones and tile flooring create a clean, comfortable backdrop throughout, while the split floor plan provides privacy for both the primary and guest suites. The combined living and dining areas are oriented toward the Gulf, with a striking corner of windows and sliding glass doors that frame the shoreline, the community pool below, and the bay in the distance. The terrace naturally extends the living space—an ideal spot to unwind and take in the changing colors of the evening sky. The kitchen is spacious and thoughtfully designed, with stone countertops, detailed tilework, stainless steel appliances, and a casual eat-in area positioned to enjoy the view. A separate dining area, complete with a wine refrigerator, offers flexibility for both everyday meals and entertaining. The primary suite is generously sized, featuring a full wall of glass with direct terrace access. Two large walk-in closets provide ample storage, and the bath includes a soaking tub, glass-enclosed shower, and dual vanities. The guest bedroom enjoys its own views of both the Gulf and the bay, along with an en suite bath for added comfort. Additional highlights include an in-residence laundry room, secure building access, and one under-building parking space. Residents of the Promenade enjoy a full-service lifestyle with concierge, 24-hour security, a newly renovated lobby and common areas, two fitness centers, club rooms, four Har-Tru tennis courts, a heated lap pool, spa, and nearly 400 feet of beachfront. The location offers easy access to the shops and dining of St. Armands Circle, blending convenience with a relaxed coastal setting. Membership to the Longboat Key Club is optional and available to residents, offering access to an array of resort-style amenities. These include 45 holes of championship golf, award-winning tennis facilities, a full-service spa and fitness center, multiple waterfront dining venues, a private beach club, marina, and a calendar of social events and activities.
100 SANDS POINT RD #114, LONGBOAT KEY, FL 34228
$2,100,00082 Days on yellowkey MLS ID: A4685212
3 Days Off yellowkey (back on 4/6/2026)
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2094 Built: 1966 Tax: $14,826 (2025)Community: Sands PointSpa: YesCondo
Taxes:$14,826
Remarks: Completely updated and offered furnished, this spectacular direct Gulf-front residence at Sands Point delivers the rare combination of expansive living space, modern design, and immediate beach access. True three-bedroom, three-bath Gulf-front residences are seldom available in this sought-after Longboat Key community, making this nearly 2,100-square-foot getaway a standout opportunity. This residence has undergone an extensive renovation that reimagines the interior with a bright, open layout designed to showcase panoramic Gulf views. Floor-to-ceiling glass sliders and expansive windows frame the turquoise waters and sugar-white shoreline beyond, while opening directly to the beachfront patio—placing the sand and surf just steps from your door. Major improvements throughout the residence include impact windows and sliders, new drywall, updated electrical and plumbing systems, newer ductwork, and a new HVAC system—creating a move-in ready coastal retreat where every detail has already been thoughtfully addressed. Inside, the thoughtfully redesigned interior blends coastal comfort with modern finishes. Wide-plank porcelain tile flooring with a warm wood finish flows throughout the residence, connecting each space with a clean contemporary aesthetic. The open great-room layout seamlessly links the chef’s kitchen, dining area, and living room, creating a welcoming environment for entertaining or relaxed beachfront living. The gourmet kitchen serves as the centerpiece of the home, featuring an oversized waterfall-edge island with dine-in seating, custom cabinetry, quartzite countertops, striking Sea Glass tile backsplash, and high-end stainless steel appliances. With the kitchen positioned to overlook the living area and Gulf beyond, every gathering benefits from a dramatic waterfront backdrop. The primary suite occupies the south side of the residence, offering privacy, tranquil water views, and a spacious walk-in closet. Its spa-inspired quartzite bathroom includes dual sinks and a large walk-in shower designed with modern finishes. Two guest bedrooms are arranged on the north side of the residence, each with access to beautifully updated quartzite bathrooms, providing comfort and privacy for visitors. The residence also includes a covered parking space conveniently located just outside the front door. Sands Point is a private Gulf-front enclave located behind the gates of the prestigious Longboat Key Club. Residents enjoy a relaxed resort setting with a beachfront geothermal-heated pool and spa, private clubhouse, shaded tiki huts along the shoreline, and beautifully maintained grounds. A short stroll leads to the community marina, where boat slips are available on a waitlist basis. Positioned on the southern end of Longboat Key, this location places you minutes from championship golf and tennis at the Longboat Key Club, the boutiques and restaurants of St. Armands Circle, and the vibrant arts and dining scene of downtown Sarasota. From boating and beach walks to waterfront dining and cultural events, this exceptional residence offers effortless access to the best of the Gulf Coast lifestyle.
Listing Agent: Roger Pettingell (941-387-1840)
2020 HARBOURSIDE DR #417, LONGBOAT KEY, FL 34228
$899,00054 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 1Condo
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.
3010 GRAND BAY BLVD #482, LONGBOAT KEY, FL 34228
$1,845,000462 Days on yellowkey MLS ID: A4640667
11 Days Off yellowkey (back on 1/19/2026)
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2250 Built: 1999 Tax: $15,440 (2024)Community: Grand Bay 4Condo
Taxes:$15,440
High School: Booker High
Middle School: Pine View School
Remarks: Under contract-accepting backup offers. This FURNISHED waterfront residence offers panoramic views of Sarasota Bay and the Gulf of Mexico, seamlessly complementing its neutral, sophisticated interior. An elegant double-door entry leads to an open floor plan with gleaming ceramic tile floors and floor-to-ceiling glass that highlights the stunning scenery. BRAND NEW IMPACT WINDOWS THROUGHOUT. The split layout ensures privacy, with a guest en-suite featuring bay views. The bright, modern kitchen includes a striking tile backsplash, white cabinetry, stainless steel appliances, stone countertops, and a tray ceiling. A breakfast bar connects to an informal dining space, perfect for daily use. The great room provides ample space for both relaxation and entertaining. The primary suite offers terrace access, his-and-hers bathrooms, and a walk-in closet with custom shelving. The wraparound terrace showcases expansive water views, ideal for enjoying both sunrises and sunsets. Residents enjoy top-tier amenities, including a 24-hour guard-gated entry, secure under-building parking, a clubhouse, a fitness center, two Har-Tru tennis courts, and two heated pools with a spa. Deeded access to a private beach and membership to the Bay Isles Beach Club enhance this exceptional lifestyle. Located just minutes from Downtown Sarasota and St. Armands Circle, this home offers luxury, convenience, and breathtaking waterfront living.
2295 GULF OF MEXICO DR #64S, LONGBOAT KEY, FL 34228
$625,000158 Days on yellowkey MLS ID: A4675582
0 Days Off yellowkey (back on 3/1/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970 Tax: $6,088 (2025)Community: Islander Club Of LongboatCondo
Taxes:$6,088
Remarks: Under contract-accepting backup offers. PRICE REDUCED! Don’t miss this opportunity, schedule your showing today! Beachfront Living at Islander Club on Longboat Key Experience relaxed beachfront living at the Islander Club, one of Longboat Key’s most established and sought-after Gulf-front communities. Located directly on the Gulf of Mexico, this beautifully updated 2-bedroom, 2-bath residence offers true resort-style living in a premier island setting. Situated on the 6th floor along the desirable south/southeast side of the building, the residence spans more than 40 feet, capturing stunning Gulf views and refreshing coastal breezes. Inside, the home has been thoughtfully refreshed with new luxury engineered wood flooring, fresh coastal-inspired paint, and updated lighting throughout. The open floor plan creates a bright, airy atmosphere, with the kitchen flowing seamlessly into the main living area. Large impact windows in the primary bedroom bring in abundant natural light while framing uninterrupted Gulf views. The primary suite includes a private ensuite bath, a full-size washer and dryer are conveniently located inside the unit, and additional storage off the living room adds everyday functionality. Residents of the Islander Club enjoy an impressive collection of resort-style amenities set on an expansive stretch of private beachfront. Community features include over 400 feet of private beach frontage, two fishing jetties, Har-Tru tennis courts, a beachfront heated pool and spa, a fitness center, saunas, and a newly renovated clubhouse with a full kitchen, library, billiards, and table tennis. The community also offers secure gated entry, elevators, professional on-site management, and 24/7 maintenance, providing both comfort and peace of mind. The location is equally exceptional. The Longboat Key Club is just a short bike ride or drive away, offering world-class golf, dining, tennis, and pickleball. The boutiques and restaurants of St. Armands Circle are less than four miles away, with downtown Sarasota’s cultural attractions, shopping, and dining just beyond. This turnkey beachfront condominium offers the perfect opportunity to enjoy effortless coastal living in one of Longboat Key’s most desirable Gulf-front communities. Simply bring your flip-flops and start enjoying the island lifestyle.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Harold Kaufman (508-525-5938)
1065 GULF OF MEXICO DR #402, LONGBOAT KEY, FL 34228
$845,000239 Days on yellowkey MLS ID: A4666641
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1392 Built: 1981 Tax: $8,124 (2025)Community: Beachplace IiiCondo
Taxes:$8,124
Remarks: This stunning 2 bed/2 bath residence comes turnkey furnished offering a full view of the Longboat Key Islandside Golf Course and partial views of the Gulf, Sarasota Bay, and the Sarasota city skyline through Hurricane Impact Sliders installed in 2024. The kitchen has been opened up to the living/dining area providing a beautiful view over the golf course greens while owners are creating culinary delights in the kitchen. There is a breakfast bar, a laundry closet, pantry, and plenty of solid wood cabinet space for storage. The primary suite pampers owners with access to the southeast-facing terrace along with a spacious primary bath offering dual vanities, an updated tile shower, and abundant closet space. The split floor plan allows for maximum privacy for both the primary and the ensuite guest bedroom. Other highlights include ceramic tile flooring throughout, stone counters, a coveted underbuilding parking space and an excellent rental policy of 1 month minimum 12 X per year. Beachplace offers a 24-hour manned guard gate, heated swimming pool & spa, tennis courts, dedicated pickleball 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.
Listing Agent: Ian Addy, Pa (941-961-8850)
1281 GULF OF MEXICO DR #111, LONGBOAT KEY, FL 34228
$1,050,00058 Days on yellowkey MLS ID: A4688079
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1392 Built: 1999 Tax: $9,956 (2025)Community: Water Club 01 At Longboat KeyCondo
Taxes:$9,956
Remarks: Welcome to a little piece of paradise on Longboat Key at the stunning gated Gulf-front condominium community of Water Club, which offers a coastal lifestyle complete with direct access to sandy beaches, high-end amenities and exceptional security and concierge services. This designer-inspired, furnished two-bedroom, 2.5-bath condominium is on the newer north building's plaza level and features nearly 1,400 square feet, 10-foot ceilings, double crown molding, plank wood flooring in the living areas, natural colors and floor to ceiling storm impact windows and doors. An open floor plan offers garden views from the spacious living room and the kitchen, which has both a breakfast bar and a seating area. A beautiful kitchen renovation was completed in December 2025 with handsome wood cabinets, stone countertops and GE Profile appliances. The split plan allows privacy for owners and guests in the two separate primary en-suite bedrooms, each with large windows, custom drapes and carpet, wall closets with built-ins and baths with combination tub/showers. ?An expansive balcony with glass railing barriers can be accessed through the living area and one of the primary suites. This lovely condo conveniently has a stack washer and dryer, linen closet, underbuilding storage unit and assigned parking and its own front desk concierge. Behind the 24-hour guarded-gate is true luxury living with a modern clubhouse, state-of-the-art fitness room, locker room and spa, sauna, bar and lounge, library, game room, ballroom and catering kitchen and outside terrace for gatherings and watching sunsets over the Gulf waters. Besides the magnificent beach and Florida-friendly landscaped grounds, the outdoor amenities include a peaceful courtyard, fire pit, resort-style pool and hot tub and new Har-tru tennis courts. Water Club is conveniently near island golf courses and Publix, and a short distance from St. Armands Circle and downtown Sarasota for dining, shopping, entertainment and cultural venues.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Kathleen Ucci (941-302-2344)
3040 GRAND BAY BLVD #213, LONGBOAT KEY, FL 34228
$1,550,000127 Days on yellowkey MLS ID: A4678941
Bed: 2 Bath: 3.5 Liv Area Sq Ft: 2550 Built: 1996 Tax: $8,474 (2025)Community: Grand Bay 2Condo
Taxes:$8,474
Remarks: Beautifully positioned within Grand Bay on Longboat Key, this 2-bedroom + den residence offers 2,550 sq ft of light-filled living with a private elevator opening directly into the home. Expansive Sarasota Bay views, two generous terraces, and seamless indoor–outdoor flow create an ideal setting for sunsets, bay breezes, and relaxed coastal living. Set behind the gated Bay Isles entrance, residents enjoy resort-style amenities, deeded beach access, and a lifestyle defined by location, comfort, and waterfront elegance. The spacious primary suite offers a tranquil retreat with direct terrace access, peaceful water views, a large walk-in closet, and a spa-like bath featuring dual vanities, a soaking tub, and a walk-in shower. The generous kitchen featuring a Sub-Zero refrigerator and causal eat-in dining, den, and guest suite each open to a second terrace that overlooks Bay Isles’ beautifully landscaped grounds and tennis courts. The den offers versatility for a home office or additional living space, while the guest suite features an en-suite bath and private access to the expansive terrace. A dedicated wine and storage room adds a thoughtful layer of convenience and elegance, blending seamlessly into the home’s well-planned layout. Grand Bay residents enjoy an array of resort-style amenities, including two pools, a fitness center, tennis courts, a clubhouse, and deeded beach access through the Bay Isles Beach Club. Set behind the secure gates of Bay Isles, this residence offers the perfect blend of space, privacy, and the coveted Longboat Key lifestyle.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Dianne Anderson (941-350-3513)
1425 GULF OF MEXICO DR #308, LONGBOAT KEY, FL 34228
$1,140,000146 Days on yellowkey MLS ID: A4676606
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2149 Built: 1983 Tax: $12,342 (2025)Community: Players Club IvCondo
Taxes:$12,342
Remarks: Enjoy the best of Gulf-front living in one of the largest units, this 3-bedroom, 3-bath residence with a flexible study/den/4th bedroom, in a gated community located on the sought-after south end of Longboat Key. This residence offers sweeping views of the Gulf of Mexico and includes an enclosed lanai with new telescopes, hurricane windows, and a spacious interior with tile floors in the main living areas and a neutral color palette. A wall of sliding glass doors in the living room opens to a spacious enclosed terrace—perfect for relaxing, dining, and enjoying the sounds of the surf through the new telescoping hurricane windows. The kitchen is large enough for all the chefs in the family. Corian countertops, a tile backsplash, and a breakfast bar that connects easily to the living space. The primary suite includes a king-size bed, wake up to view of the Gulf, access to the terrace, and an en-suite bath with a large walk-in shower. For your guests, the second bedroom has an en-suite bathroom. The third bedroom provides a great space for guests or a home office. The private terrace offers views of the beautifully maintained grounds, the beach, and the Gulf beyond. 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, 4 Har-Tru pickleball courts, a putting green, and a heated saltwater pool and spa. Players Club is located just a short drive to St. Armands Circle, where you will enjoy the shopping and dining experiences. Just over the Ringling Bridge, there are many theater options downtown Sarasota. Additional conveniences include on-site management and a 24-hour staffed gate, ensuring comfort and peace of mind.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Diane Smith (941-313-4957)
1955 GULF OF MEXICO DR #G6-311, LONGBOAT KEY, FL 34228
$1,049,00059 Days on yellowkey MLS ID: A4687954
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1492 Built: 1978 Tax: $8,677 (2025)Community: Seaplace IvCondo
Taxes:$8,677
Remarks: Experience the coastal gulf front living lifestyle to its fullest, in this 3-bedroom 2 bath condo with views of the Gulf from inside as well as the 2 balconies. Make this your new oasis and enjoy the sunsets off one of your two separate balconies (one off the main living area and another private balcony for the primary bedroom). Start experiencing this 3-bedroom condo at Seaplace which is located on a pristine beach area of Longboat Key. There is an array of amenities across the 42 beautifully landscaped acres, including two heated swimming pools and spas, Har-Tru tennis courts, scenic walking trails, a fitness center and a new gulf front firepit area. The clubhouse offers a kitchen, library, fitness area and sauna. Additional features include playground, grilling areas, on-site management, and a 24-hour staffed gatehouse.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Bruce A Meyer, Pa (941-266-8152)
1085 GULF OF MEXICO DR #404, LONGBOAT KEY, FL 34228
$950,00065 Days on yellowkey MLS ID: A4686960
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1503 Built: 1981 Tax: $5,482 (2025)Community: Beachplace IiiCondo
Taxes:$5,482
Remarks: Coveted Southern exposure offering morning sun with a very tropical feel over looking the Longboat Key Club golf course. With palm trees and beautifully landscaped grounds right outside your windows and privacy on your balcony. Featuring two bedrooms and two bathrooms, this spacious residence is open and airy with a beautifully updated kitchen, bathrooms and impact windows, this is the largest two bedroom available at Beachplace offering 1503 sq. ft. This residence also includes TWO under building parking spaces and one outside parking space that convey with the property. Beachplace offers a very nice fitness center, a guard gated entry, a Junior Olympic sized swimming pool, a splash pool, hot tub, tennis, pickle ball, grilling area and the beach is equipped with lounge chairs and umbrella's. Beachplace offers a Jr. Olympic sized swimming pool with swim lanes, a splash pool, hot tub, fitness center, grilling area, tennis, pickle ball and a 24 hour guard gated entrance. All furnishings are included and this would make a great rental.
Listing Agent: Maggie Hicks (941-321-1759)
669 SPANISH DR N #21, LONGBOAT KEY, FL 34228
$339,000364 Days on yellowkey MLS ID: A4653816
0 Days Off yellowkey (back on 3/30/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1087 Built: 1969 Tax: $5,733 (2024)Community: Spanish Main Yacht Club CondoCondo
Taxes:$5,733
Remarks: One or more photo(s) has been virtually staged. Priced to sell - Fully renovated villa ready for immediate occupancy! Welcome to Spanish Main Yacht Club, a sought-after 55+ waterfront community on Longboat Key, where coastal living meets exceptional value. This 2-bedroom, 2-bath villa-style condo offers 1700 SqFt of interior living space, 1087 of it under air, with endless potential to make it your dream home. This stand-alone condo has undergone FEMA-approved storm mitigation and a full rebuild. Bring your vision and decorate to suit your personal style—below market value! Step inside to find a spacious open-concept living and dining area, perfect for entertaining. The adjoining Florida room offers additional flexible space, bathed in natural light—ideal for morning coffee or quiet evenings. The primary suite features an en-suite bathroom, closet and indoor laundry room. Enjoy private beach access just steps away, or take advantage of the community marina with first-come, first-served boat slips, kayak racks, and direct access to Sarasota Bay. Amenities include a heated outdoor pool, shuffleboard courts, a clubhouse with game room, library, and frequent community events. This pet-friendly community offers covered carport parking, guest spaces, and maintenance-free living, all set within beautifully maintained, palm-lined grounds. Just minutes from St. Armand’s Circle and Anna Maria Island, this location offers world-class shopping, dining, and entertainment, plus access to some of Florida’s finest white sand beaches. Whether you're looking for an investment, full-time residence or a vacation getaway, this villa offers endless potential in one of Longboat Key’s most desirable communities. Seller says bring offers—don’t miss your chance to own a piece of paradise!
Listing is courtesy of: AUM FLORIDA REAL ESTATE LLC (855-286-3573)
Listing Agent: Geoff Scalera (941-321-4158)
701 SAINT JUDES DR S #3, LONGBOAT KEY, FL 34228
$259,000147 Days on yellowkey MLS ID: O6370226
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 630 Built: 1966 Tax: $3,873 (2024)Community: Saint Judes AptsCondo
Taxes:$3,873
Remarks: DIRECT WATERFRONT OPPORTUNITY IN LONGBOAT KEY! Here's your rare chance to own a waterfront property with direct access to the Intercoastal Waterway! Perfectly located for vacation rentals, this canal-front 1-bedroom, 1-bathroom end unit offers incredible potential for income, especially with high demand bookings from January to April. This property boasts 21 feet of water frontage and a newly installed seawall (June 2021). Enjoy the Florida lifestyle with easy access to boating, kayaking, and fishing. Additional outdoor amenities include a paver patio. Just steps away from a private beach access, kayak launch, and deeded beach entry. The property also has direct access to the scenic Joan M. Durante Park, with 32 acres of walking trails, gardens, recreational areas, and breathtaking Sarasota Bay views. Take a short walk to top-rated restaurants, shops, a deli, bike and kayak rentals, and more. Plus, you're just a short drive to St. Armands Circle and Anna Maria Island! This is the most economical waterfront property you'll find in all of Longboat Key!
Listing is courtesy of: NIZZ REALTY INC (954-526-5105)
Listing Agent: Filitsa Sterner Mistretta (941-928-3666)
6800 GULF OF MEXICO DRIVE #184, LONGBOAT KEY, FL 34228
$475,00062 Days on yellowkey MLS ID: A4687722
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1287 Built: 1970 Tax: $6,630 (2025)Community: Whitney BeachCondo
Taxes:$6,630
Remarks: Beautifully renovated in 2023, with dazzling views of the Gulf of Mexico and the private beach across the way, this 2nd floor island retreat is located in a charming Gulf-to-Bay community, nestled between the azure blue water of the Gulf of Mexico and serene Bishops Bayou, where Manatees & Dolphins play. This lovely 2nd level end-unit features an open floor plan, enhanced by a gorgeous designer kitchen with quartz countertop & backsplash and bronze hardware, which overlooks the dining-living room combo, all offering Gulf views. The Florida room overlooks one of the two sparkling swimming pools, which are at your disposal. Hurricane resistant sliding doors and windows offer peace of mind, and the roof has recently been replaced. Luxury vinyl flooring extends all the way through the living space, including the primary suite, which is tucked away for optimal privacy. The screened front patio is the perfect spot to relax and enjoy the turquoise water views, and there is a 9' x 5' storage room for all your toys. Just bring your flip flops & beach wear and start enjoying the laid-back island lifestyle. Two heated pool, tennis & pickleball courts, 23 boat slips, a vintage boathouse/clubhouse, grilling stations, kayak launch, shuffleboard, private deeded beach directly across the road with gazebos and beach lounges plus those amazing sunsets. Two large pets are welcome and the condo can be rented 6 times per year with one month minimum. After a fun-filled day kayaking, beach strolling, fishing or boating, first-class restaurants and casual eateries are located within a short walk, bike or boat ride. Coffee, smoothie & donut shops, liquor store, 24-hour gym, Pilates studio & beauty salon, boutiques and more are just a block away. Don't miss this wonderful opportunity to make your dreams of living on Longboat Key come true!
Listing is courtesy of: ROSEBAY INTERNATIONAL REALTY, INC (941-366-7673)
Listing Agent: Tina Rudek Stark, Pa (941-920-0303)
2425 GULF OF MEXICO DR #1E, LONGBOAT KEY, FL 34228
$1,450,000188 Days on yellowkey MLS ID: A4672789
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1470 Built: 1973Community: Sea Gate ClubCondo
Taxes:
Tax Year:
Remarks: One or more photo(s) has been virtually staged. Welcome to this rarely available Seagate direct beachfront residence, where unmatched coastal living meets exceptional convenience. Step from your private terrace straight onto the sand, an experience that truly defines beachfront living. Perfectly situated across from the Publix Bay Isles Shopping Center and just moments from the world-famous Longboat Key Club and Resort, this location offers the best of Longboat Key at your doorstep. This beautifully renovated two-bedroom, two-bath residence, just under 1,500 square feet, features a bright, open floor plan with stunning Gulf views from every room. The split-bedroom layout provides two generously sized suites with abundant storage. Designer finishes shine throughout, and no detail has been overlooked. The chef’s kitchen boasts Quartz countertops, custom backsplash tile, bright white cabinetry, new appliances, and a wine cooler, perfect for entertaining. Enjoy alfresco dining on your private terrace overlooking the gardens, pool, and shimmering Gulf waters. Few properties offer the luxury of stepping directly from your home into the sand or strolling a few steps to what often feels like your very own private pool. Seagate is celebrated for its meticulous grounds and exceptional amenities. Meandering pathways wind through lush tropical gardens, while dedicated storage for kayaks and paddle boards makes it easy to explore the turquoise Gulf. Relax under the palm-thatch huts, unwind in the spectacular resort-style pool and spa, or stay active in the state-of-the-art fitness center that rivals those in five-star hotels. The newly renovated club room provides an elegant gathering space for conversation, games, watching TV, or preparing meals in the chef’s kitchen. Perfectly positioned on the coveted south end of Longboat Key, Seagate offers unmatched access to St. Armands Circle and all of the island’s finest dining, shopping, and recreation. This is truly an extraordinary opportunity to own within one of Longboat Key’s most beloved and impeccably maintained beachfront communities.
Listing Agent: Ryan Heers (941-726-1703)
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