Location: Longboat Key
Do Not Show Listings
2425 GULF OF MEXICO DR #1A, LONGBOAT KEY, FL 34228
$1,595,0002 Days on yellowkey MLS ID: A4688987
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1470 Built: 1973 Tax: $9,602 (2025)Community: Sea Gate ClubSpa: NoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,602
Elementary School: Southside Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: This is the gorgeous ground floor, walk-out unit next to the beach you've been looking for. Do you prefer to live like a single family home, no elevator, and walk straight out to the beach? Then this is the One! Welcome to Sea Gate Club on beautiful Longboat Key, perfectly positioned near mid-island, and close to shopping at Publix or CVS. As you enter this very private End Unit #1A, you're greeted by Direct and Unobstructed Gulf and beach views as far as the eye can see. Unit #1A has been extensively updated over the last few years, featuring an open kitchen with a huge island, updated cabinets and countertops, and gorgeous porcelain tile flooring. 350' of direct and private beach frontage! This unit is offered Turnkey-Fully Furnished with very tasteful furniture that you'll actually want to keep. Sea Gate Club condos are comprised of 89 units, spread across 15 floors. The building has been extensively updated over the past few years. Recent updates include a new pool and hot tub, new roof, newer hurricane rated windows, newer exterior stucco and paint, new elevator doors, climate-controlled bike storage, and paddleboard/kayak storage. Now is the perfect time to buy in this beautiful building, as there are NO current or pending assessments! Hurry before it's gone, this one is beautiful.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Robert Delaney (941-315-3185)
779 SAINT JUDES DR N, LONGBOAT KEY, FL 34228
$492,000266 Days on yellowkey MLS ID: O6326464
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 882 Built: 1972 Tax: $5,814 (2024)Community: Villa Dos PalmasCondo
Taxes:$5,814
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: PRICE REDUCTION ! Coastal Elegance Meets Effortless Island Living in Longboat Key Experience the ultimate Gulf Coast lifestyle in this beautifully maintained 2-bedroom, 1.5-bath canal-front residence, perfectly positioned within one of Longboat Key's most desirable waterfront communities. Whether you're searching for a full-time sanctuary or a refined seasonal retreat, this exceptional property delivers comfort, style, and location in perfect harmony. Inside, a thoughtfully updated kitchen takes center stage-featuring brand-new appliances, sleek contemporary countertops, and modern cabinetry designed for both everyday living and effortless entertaining. Solid block construction offers durability and peace of mind, while the newer roof enhances long-term value and security. Step outside and immerse yourself in true island living. With deeded beach access just moments away, you can transition from morning coffee to toes-in-the-sand within minutes. Enjoy leisurely strolls to some of the island's most beloved dining destinations, including Harry's Continental Kitchens, Solorzano's Pizzeria, Lazy Lobster, Lo' Key Island Café, and the iconic Euphemia Haye Restaurant. The property also includes a private 1-car carport and dedicated exterior storage-adding convenience to coastal charm. Perfectly situated on a generous canal-front lot, this residence is a short walk to the sparkling waters of the Gulf of Mexico and only 15 minutes from the sophisticated boutiques and fine dining of St. Armands Circle. Wake to peaceful bay breezes. Spend your afternoons basking on pristine white sands. End each day with spectacular Gulf sunsets painting the sky in gold and coral hues. This is more than a condo-it's a lifestyle. Don't miss your opportunity to own a piece of paradise on Longboat Key.
Listing is courtesy of: BROKERS REAL ESTATE GROUP INC (407-770-1464)
Listing Agent: Alessandro Rosa (407-460-6589)
1425 GULF OF MEXICO DR #408, LONGBOAT KEY, FL 34228
$1,075,000117 Days on yellowkey MLS ID: A4674194
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 is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Mairead Smialek (847-334-4848)
4621 GULF OF MEXICO DR #14F, LONGBOAT KEY, FL 34228
$710,000191 Days on yellowkey MLS ID: A4664627
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 900 Built: 1973 Tax: $11,151 (2025)Community: Casa Del MarCondo
Taxes:$11,151
Remarks: Investment Opportunity with low HOA fees! Beautifully updated and decorated two-bedroom, two-bath unit with vaulted ceilings can sleep up to 6 at Casa Del Mar on Longboat Key. Casa Del Mar is a popular beach resort with short-term rentals located directly on the Gulf. Use the condo for your own vacation and enjoy all Longboat Key has to offer while collecting income the rest of the year. This turnkey furnished condo is tiled throughout and offers views of the tropically landscaped courtyard and partial Gulf views from the extended living area. The primary ensuite bedroom is furnished with a king size bed and built-in cabinetry. The guest bedroom is furnished with 2 twin beds, built-in cabinetry with a full bath in the hallway. The kitchen has stone counters, solid wood cabinets and stainless appliances. Community amenities include a huge 30’ x 60’ gulf front heated pool, grill area, tennis, pickleball and basketball. Complimentary beach lounges are provided for guests and umbrella rentals are available. Casa Del Mar’s on-site management handles year-round bookings along with all the details so you can enjoy your investment stress-free. Annual gross income for #14F: 2023 $45,131, 2024 $59,833, and 2025 $56,388. Great location convenient to St Armand’s Circle with shops, fine and casual dining, and entertainment and a short drive over the bridge to the southwest cultural hub of downtown Sarasota.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Ian Addy, Pa (941-961-8850)
1930 HARBOURSIDE DR #145, LONGBOAT KEY, FL 34228
$599,0002 Days on yellowkey MLS ID: A4686987
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1270 Built: 1982 Tax: $8,215 (2025)Community: Fairway Bay 1Spa: YesCondo
Taxes:$8,215
Remarks: Set on the 4th floor of Building 1 in Fairway Bay, this beautifully styled 2BR/2BA residence captures sweeping views across the mangroves, a navigable channel and Sarasota Bay beyond—creating a vibrant waterfront backdrop from nearly every room. Upon entry, engineered wood flooring draws your eye to a wall of glass at the rear of the residence, where shifting blue and green tones take center stage. The layout flows effortlessly from the updated kitchen into the dining area and living room, allowing the view to remain the focal point throughout. The kitchen has been thoughtfully redesigned with striking stone countertops, low-profile white cabinetry, a refined tile backsplash and stainless-steel appliances. The living room opens to an expansive terrace through a full wall of sliders, offering a front-row perspective of the mangroves and channel, where boats pass by and manatees are often seen gliding through the water—creating a setting that feels both peaceful and connected. The primary suite serves as a private retreat with rich wood flooring, direct terrace access and a well-appointed bath featuring dual vanities and a separate water closet. The guest bedroom is comfortably sized, and the guest bath has also been tastefully updated. Residents of Fairway Bay enjoy a bayside lifestyle with deeded beach access through the private Bay Isles Beach Club, one underbuilding parking space, 24-hour gated security, walking trails, a heated pool, tennis courts and a fitness center. Membership opportunities at the Longboat Key Golf & Tennis Country Club and access to deepwater slips are available, and small pets up to 15 pounds are welcome.
Listing Agent: Bruce Myer (941-376-5311)
1211 GULF OF MEXICO DR #709, LONGBOAT KEY, FL 34228
$1,749,0002 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.
2045 GULF OF MEXICO DR #M1-502, LONGBOAT KEY, FL 34228
$469,500110 Days on yellowkey MLS ID: A4675820
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 928 Built: 1974 Tax: $6,201 (2025)Community: Seaplace IiCondo
Taxes:$6,201
Remarks: A perfect coastal retreat located in Seaplace, and now at an unbeleivable price! This is one of Longboat Keys most desirable beachfront communities. A light and bright 2 bedroom, 1 plus bath, 5th floor condo with a beautiful Bay view. (the photos of the view just do not do it justice!) An exceptional location in the highly sought-after Gulf-front M1 building means you can have your toes in the sand in mere moments. It is beautifully turn-key furnished and meticulously maintained and is ready for its next appreciating owner. The large primary bedroom has its own private ensuite portion of the bath with a sink that can be shut off from a full bath, making it what one would call a 1 bath PLUS. The 2nd bedroom offers a perfect spot for visitors to help you enjoy this amazing way of life to the fullest. Seaplace offers resort style living with unmatched amenities that include 2 large pools and hot tubs; a kiddie pool; 3 har-tru tennis courts; a recently renovated Gulf-front clubhouse; a fitness center; library; gas grills; a one-mile paved walking path surrounding the lush 42-acre property, and a gatehouse with 24-hour security. Located near the newly opened St.Regis Resort, St.Armands Circle and the cultural epicenter of downtown Sarasota, you’ll be close to world-class restaurants, hotels, entertainment, arts, culture, and shopping. Come see this fabulous condo soon and make your island living dream a reality in 2026!
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
576 SUTTON PL, LONGBOAT KEY, FL 34228
$359,000110 Days on yellowkey MLS ID: A4675729
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1270 Built: 1972 Tax: $6,222 (2024)Community: Sutton PlaceSpa: YesCondo
Taxes:$6,222
Elementary School: Anna Maria Elementary
High School: Manatee High
Middle School: Martha B. King Middle
Remarks: Best Beach Villa Value on Longboat Key! - Experience effortless coastal living in this lovely 2-bedroom, 2-bath end-unit bayside villa offering the highly sought-after Bay-to-Beach lifestyle on Longboat Key. Beautifully appointed and sold turnkey, this ground-floor residence is truly Martha Stewart–perfect—move-in ready and designed for relaxed elegance. The villa welcomes you with an enclosed den/Florida room, a serene retreat where you can unwind while enjoying tranquil views of lush greenery and native birdlife. Hurricane impact windows and doors throughout ensure peace of mind while maintaining a quiet, comfortable interior. The open-concept living space is ideal for both everyday living and entertaining. A spacious family room and dining area flow seamlessly from the renovated kitchen, which features rich maple cabinetry, solid granite countertops, and an inviting, functional layout. Every detail has been thoughtfully curated, from custom cornices and blinds to coordinated bedding and decorative pillows—straight out of Serena & Lily. Additional highlights include a separate laundry room with pantry storage, complete with a garden door that opens to peaceful landscaping and provides direct access to the private marina, kayak storage, and an electric kayak launch—perfect for embracing the boating lifestyle right outside your door. This pet-friendly villa offers unmatched convenience and value with a private carport, extra guest parking just steps away, a new washer and dryer, a recently upgraded air-conditioning system and tankless water heater. Just across Gulf of Mexico Drive, enjoy exclusive access to your private beach facility, featuring gated parking, restrooms, showers, and chair storage—true resort-style living. Spend your days boating, kayaking, or soaking up the sun, then end each evening watching breathtaking sunsets over the sugar-sand beaches of the Gulf. This exceptional Longboat Key villa is move-in perfect and ready to enjoy—just bring your flip-flops. Opportunities like this are rare, and this one will not last long.
Listing Agent: Kathy Callahan (941-900-8088)
4805 GULF OF MEXICO DR #103, LONGBOAT KEY, FL 34228
$699,00089 Days on yellowkey MLS ID: A4677568
1 Days Off yellowkey (back on 4/6/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1393 Built: 1970 Tax: $6,331 (2024)Community: Westchester AptsSpa: NoCondo
Taxes:$6,331
Remarks: Under contract-accepting backup offers. NEW Best Price Opportunity Beach Front! Thoughtfully Updated with high- quality finishes! Experience refined Gulf-front living in this first-floor, Gulf-view residence with direct walk-out access to a private sandy beach. This pristine 2-bedroom, 2-bath home showcases an updated kitchen and spa-inspired baths, impact-resistant sliding doors that open seamlessly to two screened lanais, and a generously sized guest suite accommodating two double beds. A private laundry room with full-size washer and dryer, two interior storage closets, and a spacious exterior storage unit add exceptional convenience. Offered furnished with select exclusions. Milestone inspections are complete and assessments paid in full—delivering confidence and long-term value. Westchester is an exclusive, impeccably managed beachfront community set on 7 acres with 700 feet of shoreline, featuring two heated pools, beach loungers, tiki huts, pickleball and tennis courts, shuffleboard, BBQ grills, kayak and bicycle storage, and on-site management. A new clubhouse with a fitness center and enhanced Gulf-side pool and landscaping are underway. A rare opportunity for elevated coastal living and investment excellence. CHECK THE VIRTUAL TOUR, and reserve your private viewing
Listing Agent: Malihe Karimi (941-376-5099)
4621 GULF OF MEXICO DR #16B, LONGBOAT KEY, FL 34228
$649,900474 Days on yellowkey MLS ID: A4632978
3 Days Off yellowkey (back on 4/6/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 900 Built: 1972 Tax: $7,292 (2024)Community: Longboat Key Casa Del MarSpa: NoCondo
Taxes:$7,292
High School: Bayshore High
Remarks: Under contract-accepting backup offers. Imagine the serene sands of the Gulf, just steps away, offering the ideal blend of luxury and opportunity with rental income while you're away. An on-site rental office ensures seamless bookings for your beautifully renovated condominium with new A/C at Casa Del Mar. You and your guests will relish the gulf-front pool, tennis courts with pickleball, grilling area and picnic tables, all while basking in the soothing embrace of the gulf waters as the simple, fulfilling life awaits. For those who wish to travel light, the unit is turnkey furnished, fully equipped, and ready to provide your ideal beach getaway. Upgrades include new kitchen and baths, quartz countertops and tile throughout, and stainless-steel appliances. The unit comes with a washer and dryer. just a short drive to local restaurants, Anna Maria Island, local parks, grocery shopping, CVS, places of worship, banks, world-renowned St, Armands Circle, top-rated Sarasota and all it offers.
Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (941-364-4000)
Listing Agent: Dennis Girard (941-809-0041)
554 SPANISH DR S, LONGBOAT KEY, FL 34228
$435,0006 Days on yellowkey MLS ID: A4688632
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1326 Built: 1971 Tax: $2,179 (2025)Community: Spanish Main Yacht Club CondoCondo
Taxes:$2,179
Remarks: Welcome to Spanish Main Yacht Club waterfront community and your new home! Light and bright, this stand-alone villa is all new and beautifully updated in 2026. White marble-like large porcelain tile floors that span the entire living area, providing a continuous flow throughout the villa. The new kitchen boasts stainless steel appliances, white quartz countertops, new cabinetry, lighting and more. Attractive updates in the primary en suite bedroom and guest bath as well. A nice added feature is the spacious interior laundry room. Beautiful, lush backyard view with privacy and an extra brick paver side yard and outdoor space. A short stroll to the privately deeded beach entrance to gorgeous Gulf beaches. Two minutes to have your toes in the soft, pearly sand. This is a boater’s paradise with slips available for an extremely inexpensive lease and direct access to Sarasota Bay, the Intracoastal waterway and azure waters of the Gulf. Only a short drive to the fantastic shops, restaurants and cultural events Sarasota and St. Armands Circle have to offer. This is a great investment opportunity and chance to enjoy Longboat Key living. The community is in the build-back stage due to damage from hurricanes in 2024 and is almost complete. All 212 units in Spanish Main are under FEMA requirements, guidelines, and stringent adherence to rebuild specifications and inspections from Town of Longboat Key. This is an opportunity to continue to make this villa your custom home.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Kimberly Freiwald (941-256-6775)
1915 HARBOUR LINKS CIR #6, LONGBOAT KEY, FL 34228
$1,950,0006 Days on yellowkey MLS ID: A4688148
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2476 Built: 2002 Tax: $19,319 (2025)Community: Bay IslesSpa: YesCondo
Taxes:$19,319
High School: Sarasota High
Remarks: Welcome to Emerald Pointe South in the gated Bay Isles community on Longboat Key. This well-maintained residence offers a light and open floor plan with spacious living and dining areas, ideal for everyday living and entertaining. Sliding glass doors provide abundant natural light and lead to a private screened lanai overlooking lush tropical landscaping. The kitchen features ample cabinetry, solid surface countertops, a breakfast nook, and recent updates including a new microwave, dishwasher, and stove. The primary suite offers dual walk-in closets and an en-suite bath with dual vanities, soaking tub, and separate shower. Two additional bedrooms, each with en-suite baths, are located on the second floor, providing privacy for guests or family. Residents enjoy access to the private Bay Isles Beach Club. Ideally located just minutes from St. Armands Circle and downtown Sarasota, this home offers convenient access to dining, shopping, and beaches. Perfect as a full-time residence or seasonal retreat, this property captures the best of Longboat Key living.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Cathy Palmer (678-524-1104)
100 SANDS POINT RD #114, LONGBOAT KEY, FL 34228
$2,100,00033 Days on yellowkey MLS ID: A4685212
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)
3500 GULF OF MEXICO DR #104, LONGBOAT KEY, FL 34228
$649,00085 Days on yellowkey MLS ID: A4675727
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1486 Built: 1980 Tax: $5,798 (2025)Community: Buttonwood CoveCondo
Taxes:$5,798
Remarks: Major Price Reduction – Seller Says It’s Time to Sell! Rarely available 3-bedroom, 2.5-bath condo in Buttonwood Cove on Longboat Key, just steps across the street from deeded beach access to the beautiful Gulf of Mexico. This light-filled unit is right across the road from the Gulf with peekaboo views from the front guest bedrooms and full peaceful bay views from all living areas and owners bedroom, creating the perfect island setting from sunrise to sunset. The spacious layout includes an open living and dining area, a private Gulf-facing lanai, and three generously sized bedrooms, providing plenty of room for family and guests. Buttonwood Cove is a boutique waterfront community of only 56 residences offering resort-style amenities including a heated pool, tennis and pickleball courts, fishing pier, kayak launch, and boat docks. Recent community improvements include newer roof, elevators, driveways, exterior paint, and Trex docks, and the association is up to date on milestone inspections. Under-building parking, private storage, and deeded beach access with chairs provided make island living easy. Located just minutes from St. Armands Circle, Longboat Key Club, downtown Sarasota, and SRQ Airport, this is a fantastic opportunity to own a spacious 3-bedroom beachside condo on Longboat Key at a newly reduced price. Seller is motivated — schedule your showing today.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Samantha Kotlik (941-447-2175)
3060 GRAND BAY BLVD #195, LONGBOAT KEY, FL 34228
$1,695,00085 Days on yellowkey MLS ID: A4677880
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2250 Built: 1994 Tax: $10,399 (2025)Community: Grand Bay 1Spa: YesCondo
Taxes:$10,399
Remarks: One or more photo(s) has been virtually staged. Positioned high on the south side and 9th floor of Building One, this turnkey-furnished residence at Grand Bay offers expansive Sarasota Bay, golf course and downtown views, refined interiors, and effortless resort living on Longboat Key. Spanning nearly 2,300 square feet, the open layout is framed by walls of glass and a wraparound terrace with access from nearly every room—creating a seamless connection between indoor spaces and the ever-changing water views below. Recently refreshed with new contemporary furnishings included, the residence is truly move-in ready. The spacious great room flows naturally into the dining area and kitchen, creating an inviting setting for entertaining or relaxed daily living. Floor-to-ceiling glass sliders bring in abundant natural light while showcasing views of the bay, marina, and downtown Sarasota. The primary suite is a private retreat with terrace access, generous closet space, and a well-appointed en-suite bath. Two additional bedrooms provide flexibility for guests, office use, or extended stays, each positioned to enjoy natural light and views. Electric storm shutters throughout offer convenience and peace of mind. This residence includes two deeded parking spaces and an additional storage unit, a valuable combination rarely available at this elevation. Grand Bay is one of Longboat Key’s most sought-after gated communities, offering residents a full suite of resort-style amenities including two heated swimming pools with sundecks, Har-Tru tennis courts, a modern fitness center, clubhouse, and an active social calendar. On-site management and 24-hour security ensure a well-maintained, secure environment. As an exclusive benefit, owners enjoy deeded access to the private Bay Isles Beach Club, where Gulf-front pavilions, grilling areas, and pristine shoreline create the perfect setting for beach days and sunset gatherings. Located behind the gates of Bay Isles, Grand Bay balances privacy with proximity. Just minutes away are the boutiques and restaurants of St. Armands Circle, the cultural offerings of downtown Sarasota, championship golf and marina access at Harbourside, and the beaches of Lido and Siesta Key. From boating and tennis to theater, dining, and art, this residence places the best of Sarasota living within easy reach. A rare opportunity to enjoy turnkey bayfront living in one of Longboat Key’s premier communities.
1914 HARBOUR LINKS CIR #10, LONGBOAT KEY, FL 34228
$1,495,0007 Days on yellowkey MLS ID: A4686139
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2180 Built: 2001 Tax: $12,540 (2025)Community: Emerald Pointe SouthSpa: NoCondo
Taxes:$12,540
Remarks: Tucked behind the gates of Bay Isles in the Emerald Pointe community, this 3BR/3.5BA residence offers 2,180+/- sq. ft. of thoughtfully designed living space with a layout that blends privacy, flexibility and inviting outdoor living. From the moment you arrive, a paver drive framed by lush landscaping and a striking 2-story façade with barrel tile roof set a warm and welcoming tone. A paver walkway leads to the courtyard entrance that defines the home’s character. This open yet private space is bathed in natural light and features a covered and screened sitting area with an all-season kitchen, creating a unique setting for entertaining or quiet relaxation. Just off the courtyard, a separate casita with its own full bath offers ideal space for a home office, guest suite or creative retreat. Inside, the home feels open and spacious, with large tile flooring, high ceilings and a thoughtful mix of clerestory and transom windows that bring light into every corner. Neutral tones and layered textures add depth without distraction. The living room is both functional and inviting, featuring a fireplace, built-in wine refrigerator, and ice maker that enhance the space for everyday living or hosting. The kitchen has been beautifully updated and connects naturally to the main living areas. It features stone countertops, all-white cabinetry, stainless steel appliances, a tile backsplash and a breakfast bar, along with a dining area highlighted by a striking aquarium window that looks back into the courtyard. The primary suite is located on the main living level in a private wing, offering direct access to the pool and a generous walk-in closet. The bath is well appointed with dual vanities, a freestanding tub, a walk-in shower and refined tilework. Upstairs, a guest bedroom provides comfort and privacy, complete with wood flooring, a walk-in closet, desk space and an en suite bath. At the back of the home, a screened lanai and pool overlook a peaceful lake with fountain, where large-panel screening keeps the view open and unobstructed. Additional features include an in-residence laundry room and a two-car garage with abundant storage. Residents of Emerald Pointe enjoy a maintenance-free lifestyle along with access to the private Bay Isles Beach Club, offering white sand beaches just minutes away. Optional membership to the Longboat Key Club further enhances the lifestyle with championship golf, tennis and pickleball, a private beach club, marina, spa and wellness amenities, multiple dining venues, and an active social calendar.
4540 GULF OF MEXICO DR #204, LONGBOAT KEY, FL 34228
$595,000180 Days on yellowkey MLS ID: A4667631
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1312 Built: 1975 Tax: $9,451 (2024)Community: Windward BayCondo
Taxes:$9,451
Remarks: MOTIVATED SELLER! FULLY FUNDED RESERVES FOR 2026! PET FRIENDLY! NO UPCOMING SPECIAL ASSESSMENTS! 3 BEACH ACCESS POINTS! MILESTONE INSPECTION PASSED! Welcome to your island retreat, an impeccably renovated 2-bedroom, 2-bath residence offering luxury Longboat Key living at its finest with preserved mangrove and Sarasota Bay views. Every detail has been thoughtfully updated ,this home has been renovated from top to bottom, featuring new flooring, new plumbing, new electrical, new lighting, hurricane-impact windows with shutters for peace of mind and MORE! The brand-new kitchen showcases quartz countertops, custom cabinetry, and all-new stainless-steel appliances, creating a beautiful space that opens to the bright and airy living area. Both bathrooms have been updated with modern finishes and quarts countertops as well. A Murphy bed in the office area adds versatility, perfect for guests or additional workspace. Enjoy deeded beach access directly across the street for endless days on the sand, or take advantage of boat slips available for residents, ideal for boaters looking to explore Sarasota Bay and the Gulf. Windward Bay is a pet-friendly, amenity-rich community offering multiple pools, tennis and pickleball courts, a fitness center with sauna, kayak storage, and walking paths along the bayfront. Perfectly situated near world-renowned restaurants on Longboat Key, St. Armands Circle, and Anna Maria Island, this home combines effortless luxury with the ultimate coastal convenience. Move-in ready and maintenance-free, your Longboat Key lifestyle awaits!
Listing is courtesy of: VRI HOMES (800-531-2885)
Listing Agent: Paulina Vasiliev, Pllc (941-225-5383)
2109 GULF OF MEXICO DR #1303, LONGBOAT KEY, FL 34228
$1,075,00086 Days on yellowkey MLS ID: A4677817
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1463 Built: 1984 Tax: $9,654 (2025)Community: Sunset BeachCondo
Taxes:$9,654
Remarks: Discover effortless beachfront living in this beautifully furnished and renovated 2-bedroom, 2-bath residence. A rare opportunity to own a refined boutique beachfront escape of only 65 residences—where sophistication meets the relaxed elegance of Gulf Coast living. Captivating Gulf views are enjoyed from EVERY room. The light and airy interior welcomes you with a sun-filled, open-concept layout framed by floor-to-ceiling impact glass windows capturing breathtaking Ocean vistas. The living, dining, and kitchen spaces connect seamlessly, creating a welcoming environment for both entertaining and everyday relaxation. The renovated kitchen is thoughtfully designed for modern coastal living, complete with Cambria quartz countertops, an oversized island perfect for meal prepping as well as breakfast seating, LG stainless steel appliances, and soft-close cabinetry complete the package. Step onto the private balcony to enjoy morning coffee or evening cocktails as spectacular vibrant sunsets unfold over the water and paint the sky. The primary suite serves as a tranquil coastal sanctuary, featuring expansive Gulf views, the gentle rhythm of the surf, spacious walk-in closet, and a beautifully appointed ensuite bath. The guest bedroom provides both privacy and beautiful water views, making it ideal for hosting friends and family. An interior laundry room with additional cabinetry adds convenience and functionality. Covered under-building parking and additional storage complete this exceptional offering. Sunset Beach, an intimate private beachfront community without the crowds of a larger complex but still offers resort-inspired amenities including a heated pool, spa, fire pit, BBQ grills, and direct access to powdery white sand beaches just beyond your doorstep. Ideally positioned near St. Armands Circle, the Longboat Key Club, marinas, dining, shopping, and entertainment, this home offers the perfect balance of location and coastal beauty. A rare opportunity to own an exceptional Gulf-front retreat designed for the relaxed rhythm of island life. (Second bedroom virtually staged)
Listing Agent: Wendy Leventhal (941-376-4894)
4234 GULF OF MEXICO DR #J1, LONGBOAT KEY, FL 34228
$599,00027 Days on yellowkey MLS ID: A4685764
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1150 Built: 1973 Tax: $2,273 (2025)Community: Pelican Harbour & Beach ClubCondo
Taxes:$2,273
Remarks: Go and Show! Renovated - Waterfront - Pet-Friendly - Discover relaxed coastal living in this beautifully renovated two-bedroom, two-bath bayfront condominium positioned to capture stunning sunrise views over the water. With an open floor plan and expansive bay views from the great room, this residence blends comfort, style and the best of waterfront living. The updated interior features porcelain tile flooring throughout, a bright and airy living space, and a bayfront lanai where you can start your mornings watching the sun rise over the water. The kitchen is equipped with new appliances, and the home also includes in-unit laundry for everyday convenience. Recent improvements provide peace of mind, including a new air-conditioning system, new water heater and hurricane-rated doors. The spacious primary suite offers a private en-suite bath, while the guest suite enjoys direct access to the second bath, creating an ideal layout for family and friends. The condominium is nicely furnished, making it move-in ready. Residents enjoy a full range of resort-style amenities, including private beach access, community pool, tennis courts, pickleball courts, boat docks accommodating vessels up to 28 feet, a clubhouse, organized social activities, bike storage, kayak storage and launch, and on-site maintenance. The well-maintained association has completed numerous recent upgrades, such as new roof, hurricane-rated carports, new docks, freshly painted buildings, and newly re-surfaced tennis and pickleball courts, ensuring long-term value and appeal. You'll also appreciate the association's pet-friendly policy. Association fees include building and flood insurance, cable, water, sewer, trash, escrow reserves, and comprehensive grounds and building maintenance, offering low-maintenance ownership. In a desirable mid-key location, this property is ideal for enjoying the best of island life with exceptional boating, kayaking, and easy access to the bay and Gulf. Whether you’re looking for a full-time residence, seasonal retreat or investment opportunity, this bayfront condominium delivers the ultimate Florida waterfront lifestyle.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Michael Seamon (941-586-1802)
4900 GULF OF MEXICO DR #203, LONGBOAT KEY, FL 34228
$699,000154 Days on yellowkey MLS ID: A4670932
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1325 Built: 1975 Tax: $8,395 (2025)Community: Windward Bay AmdCondo
Taxes:$8,395
Remarks: IN THE COVETED "B" BUILDING, A STRATEGIC PRICE REFINEMENT NOW POSITIONS THIS EXCEPTIONAL RESIDENCE AS THE MOST COMPELLING OFFERING AT WINDWARD BAY! A BAYFRONT BEAUTY! VIEWS THAT STEAL THE SHOW! Discover the ultimate in Florida Gulf-to-Bay living with this beautifully remodeled 2-bedroom, 2-bath luxury condo offering jaw-dropping, multi-million-dollar water views of Sarasota Bay. From the moment you enter, you’ll be drawn into a world where comfort, beauty and the quiet grace of nature welcomes you like an old friend. Wake up to spectacular sunrises over the sparkling bay and unwind with mesmerizing sunsets on the Gulf, directly across the street. Watch playful dolphins, jumping fish, gentle manatees, and vibrant Florida birdlife from your Florida Room or while preparing meals in your updated kitchen overlooking the shimmering waters. Your primary suite is a serene waterfront retreat, perfect for moonlit nights and sunrise mornings. Every detail of this condo has been thoughtfully designed to create a lifestyle of tranquility and relaxation, including remote controlled blinds in the Florida Room. Located in pet-friendly Windward Bay, where two pets are welcome, this community offers the best of Longboat Key Coastal Dream Living. From dolphins at dawn to sunsets on the Gulf—every day is paradise. Community Highlights: Enjoy three beach access points (including one private), 26 acres of lush tropical surroundings including ½ mile of nature trails, two heated pools for year-round enjoyment, fitness center and sauna, clubhouse for social gatherings, tennis and pickleball courts, boat docks (waitlist) and kayak launches for water enthusiasts, covered parking and storage. With convenient access to Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez fishing village, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. The Windward Bay Association has been busy with a multitude of improvements and updates in the last few years including: Brand new roofs, resealing the buildings bayfront exteriors and painting of all the midrises in 2023/2024. Private roads were repaved and a new 1/2 mile long salt-tolerant privacy hedge was planted in October 2025. Windward Bay is a financially healthy Condo Association with a proactive Board. The Milestone Inspection and Capital Reserve Study are complete and Monthly Condo Fees for 2025 were actually reduced and 2026 Condo Fees only increased by $13 a month. This is more than a home—it’s a lifestyle. Experience the beauty, serenity, convenience, and the maintenance free life you’ve always dreamed of. GREAT NEWS, PAST CAPITAL IMPROVEMENT ASSESSMENTS WERE PAID IN FULL BY SELLER, NOT ADDED TO MONTHLY DUES! Schedule your private showing today and make paradise yours!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Debby Mccaig (941-544-1713)
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