Location: Longboat Key
Do Not Show Listings
100 SANDS POINT RD #114, LONGBOAT KEY, FL 34228
$2,100,00039 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$14,826
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
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 is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Roger Pettingell (941-387-1840)
3500 GULF OF MEXICO DR #104, LONGBOAT KEY, FL 34228
$649,00091 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
$1,695,00091 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.
2109 GULF OF MEXICO DR #1303, LONGBOAT KEY, FL 34228
$1,075,00092 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
$599,00033 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)
4350 CHATHAM DR #205, LONGBOAT KEY, FL 34228
$259,90067 Days on yellowkey MLS ID: A4681134
0 Days Off yellowkey (back on 4/4/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 667 Built: 1969 Tax: $4,627 (2024)Community: Longboat HarbourCondo
Taxes:$4,627
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2024
Middle School: Martha B. King Middle
Remarks: Under contract-accepting backup offers. Resort-style living at Longboat Harbour! This move in ready one bedroom, one bath condo is one of the best get-aways in the area. From your lanai, the serene view down the canal makes for a great place to have your morning coffee or enjoy a sunset cocktail. Steps away, you have private gated access to the Gulf beaches including a pavilion with washrooms, lockers and parking. If you like, this condo can be an incredible investment opportunity, earning rental income from day one. In 2025 the A/C unit was replaced, water heater 2023. In 2025, all the roofs were replaced, along with the elevators in Building E. There is private storage, assigned covered parking, and plenty of guest parking. The pool nearest you has been resurfaced and new pavers added throughout the complex. Longboat Harbour is a friendly community with numerous amenities and an on-site management team. It boasts four heated pools, tennis and pickleball courts, putting green, and kayak storage with launch. For boating enthusiasts, slips are available for powerboats and sailboats up to 34 feet on a first-come, first-served basis. At the clubhouse there is a fully equipped gym (with sauna and lockers) and the renovated community room overlooking the bay hosts many social occasions and private parties. Whether for a warm winter getaway, year-round residence or investment opportunity, Longboat Harbour is resort-style living at its best!
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Tracey Fiedler (303-809-2582)
2301 GULF OF MEXICO DR #91N, LONGBOAT KEY, FL 34228
$825,00083 Days on yellowkey MLS ID: A4675895
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970 Tax: $9,973 (2025)Community: Islander Club Of LongboatCondo
Taxes:$9,973
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to an exceptional opportunity to create a beachfront residence tailored to your own vision in this 3BR/2BA, 9th-floor residence at the Islander Club on Longboat Key. From the moment you step through the foyer, the horizon unfolds, revealing sweeping blues and greens that trace the shoreline and stretch across the Gulf, forming a breathtaking backdrop that changes throughout the day. Wood floors flow throughout the residence, complementing the natural palette beyond the glass. The living room is defined by a full wall of sliders that open to an expansive terrace positioned directly above the beach. From here, the sights and sounds of the shoreline become part of daily life. The expansive balcony extends along the Gulf side of the residence, extending the outdoor living space and offering multiple vantage points along the coast. The kitchen features white cabinetry, contrasting black stone countertops, white appliances, and a clean tile backsplash, with a convenient serving window connecting to the living area for easy entertaining. The primary suite offers its own wall of sliders opening to the terrace and uninterrupted views of the beach and Gulf beyond. The second bedroom provides comfortable space for family or visitors, while the flexible layout allows for thoughtful updates that can enhance both style and functionality over time. Set in a prime mid-key location, Islander Club offers a resort-style environment with a beachfront swimming pool, tennis courts, updated clubhouse, fitness center, library, billiards room, and secure gated entry. All just steps from the sand and a short drive to the shopping, dining, and cultural attractions of St. Armands Circle and downtown Sarasota.
Listing Agent: Bruce Myer (941-376-5311)
2039 GULF OF MEXICO DR #G3-203, LONGBOAT KEY, FL 34228
$539,00011 Days on yellowkey MLS ID: A4688685
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1214 Built: 1974Monthly Fee: $1,170 Tax: $5,576 (2025)Community: Seaplace ICondo
Taxes:$5,576
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: Experience the Best of Coastal Living at Seaplace on Longboat Key! Welcome to this beautifully maintained 2-bedroom, 2.5-bath residence offering a perfect blend of comfort, style, and relaxed island living. This spacious two-level layout features an inviting open-concept living and dining area with neutral coastal tones, tile flooring throughout the main level, and seamless access to a private lanai—ideal for enjoying tranquil views and Gulf breezes. The updated kitchen is designed for both functionality and style, showcasing granite countertops, white cabinetry, stainless steel appliances, and a convenient breakfast bar, perfect for casual dining or entertaining. Upstairs, you’ll find two generously sized bedrooms, each offering privacy and comfort. The primary suite serves as a relaxing retreat, while the guest bedroom is ideal for family or visitors. The additional half bath on the main level adds convenience for guests. This residence is offered in move-in ready condition and reflects pride of ownership throughout. 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 playground areas, grilling stations, on-site management, and a 24-hour staffed gatehouse for security. Whether you're searching for a primary residence, vacation getaway, or investment opportunity, this home offers the ultimate Longboat Key lifestyle in one of the island’s most sought-after communities. Schedule your private showing today!
Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
Listing Agent: Michael Renick Pllc (941-400-8735)
2450 HARBOURSIDE DR #244, LONGBOAT KEY, FL 34228
$2,450,00011 Days on yellowkey MLS ID: TB8491404
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 to Marina Bay – the premier condominium within the gated Bay Isles Community on Longboat Key. This exceptional corner residence spans 3,578 sq ft of sunlit, sophisticated living, and shares it fourth floor lobby with only one other unit. The large, updated kitchen/dining room features extra-large windows allowing for an unobstructed view of Sarasota Bay. Exquisite floor-to-ceiling windows, in the oversized living room, frame sweeping panoramic vistas of Sarasota Bay and downtown Sarasota, while the unusually large balcony provides the perfect setting for morning coffee, evening relaxation, and observing abundant bird and marine life. A second, west-facing balcony delivers spectacular Gulf sunsets, offering the rare pleasure of both sunrise and sunset living. Marina Bay is the epitome of resort-style living, with a heated pool and spa, newly renovated tennis and pickleball courts, and well-appointed fitness room. Head to the adjacent marina or around the manicured Longboat Key Club Harbourside Golf Course. Ideally situated, this residence is in close proximity to Publix, CVS, Chase Bank, and local shops. Whether as a refined full-time residence or an elevated part-time retreat, this rare offering delivers unmatched luxury, convenience, and island living. Key Features include: Corner-end unit with 3 bedrooms and 3 ½ newly renovated baths, A walk-in double shower in main suite, New floor tile on oversized screened balcony, bathrooms, and main suite floors, Equipped with storm shutters, and access to private beach for Bay Isles residents only.
Listing is courtesy of: REDFIN CORPORATION (617-458-2883)
Listing Agent: Steven Weiss (845-242-5473)
2020 HARBOURSIDE DR #417, LONGBOAT KEY, FL 34228
$899,00011 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.
4955 GULF OF MEXICO DR #101, LONGBOAT KEY, FL 34228
$5,650,00028 Days on yellowkey MLS ID: A4686511
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3122 Built: 2007Monthly Fee: $6,860 Tax: $23,380 (2025)Community: PositanoCondo
Taxes:$23,380
Remarks: Completely redone with the highest detail to finishes just finished in 2025! Spectacular walkout to the beautiful beach and azure Gulf of Mexico from this first floor beachfront condo that features a private pool and spa. Positano, a 10 acre oasis with only 29 residences, has a full time security and a gated entrance. This is Florida living at its very best! A fantastic wrapping terrace on the gulfside offers outdoor enjoyment from the main living area and master suite with steps leading down to the private pool. Two other terraces off the additional bedrooms with privacy and wonderful views. This true three bedroom all with private baths is 3343 square feet. A Gulf front gourmet kitchen with state-of-the art appliances has an adjacent family gathering area. The open plan flows from the living room area to the dining room and the floor to ceiling windows dramatically overlook the Gulf of Mexico and beach. This home has a private elevator which leads to a home with beautiful wood floors, 10 foot ceilings, crown molding and comes with a private enclosed over size garage. The Owners' Club amenities include a state-of-the-art fitness center, catering kitchen, lounge with a fireplace, Plasma TV and surround sound system. There is a 75 foot olympic pool and spa plus outdoor grilling and shaded cabanas. The grounds are lush with tropical foliage and meticulously maintained
Listing is courtesy of: DEVELOPERS REALTY LBK, INC (941-799-9096)
Listing Agent: Reid Murphy (941-232-3304)
515 FOREST WAY, LONGBOAT KEY, FL 34228
$1,420,00081 Days on yellowkey MLS ID: A4679679
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2880 Built: 1989Monthly Fee: $1,698 Tax: $4,802 (2025)Community: Cedars East Sec 2Condo
Taxes:$4,802
Remarks: NEW PRICE, AMAZING OPPORTUNITY!!! Experience the ultimate island lifestyle in this masterfully renovated 2,880 sqft, 4 Bed/3 Bath "lock-and-leave" condo at Cedars Tennis Resort and Club. Elevated sanctuary on the tranquil north end of Longboat Key. Offering the expansive feel of a single-family residence with the effortless "lock-and-leave" ease of being in the beautiful condo community of Cedars Tennis Resort and Club. This exquisite 4BR/3BA retreat defines coastal chic. A private elevator serves all three levels, opening into a sun-drenched great room with soaring ceilings, a fireplace, and a gourmet kitchen featuring dual islands and designer finishes. The refined dining room opens right off of this space with its custom built-in cabinetry and dry bar, ideal for any social gathering. Relax on your private, screened lanais overlooking lush tropical foliage and serene ponds, with peek-a-boo views of the Gulf. There is one on each living level. Rounding out the main living area is a versatile den/office (currently used as the 4th bedroom), a full third bathroom, beautiful hardwood floors throughout and a dedicated laundry room. The primary suite is a true oasis with a spa-inspired sunken bath, large walk-in shower, dual vanities and walk-in closets. Upstairs beyond the oasis of a primary there are two additional oversized guest bedrooms and a beautifully renovated guest bathroom with a walk-in shower. Recent updates beyond the full interior renovation include 2026 garage door replacements, and 2024 roof and AC replacement. Hardi- Board siding on exterior and Pella high-impact windows. The split 3-car garage provides total peace of mind and the rare abundance of space and storage. Nestled in the 66-acre village-like townhome community enveloped by nature, providing effortless access to both the beach and the bay on the beautiful north end of Longboat Key. The spacious and tropical community features lit boardwalks winding through mangroves, leading to an array of exceptional amenities including a heated Jr. Olympic Size Pool, nine Har-Tru Tennis Courts, three Pickleball courts, a Clubhouse with a Pro-Shop, a 24-hour Fitness Center, a Tiki bar, a restaurant, a fishing pier, and a kayak launch. Please note that some amenities require an additional club membership. The property is within walking distance to a variety of local attractions, such as Harry's Deli & Continental Kitchen, the true island gem that is Joan Durante Park, Euphemia Haye Restaurant & The Haye Loft, and, of course, Longboat Key's globally renowned sugary white sand beaches. Furthermore, it offers convenient proximity to other major attractions and cultural venues, including St. Armand's Circle, Mote Aquarium, the Asolo Repertory Theatre, Van Zel Performing Arts Center, Marie Selby Gardens, Anna Maria Island, the Ringling Museum complex, and numerous dining options on Longboat Key and in downtown Sarasota. Cedars East is the rare community on LBK that offers shorter-term rental allowance with its 2-week minimum, making it the perfect balance for offsetting costs when not in use, without living in a hotel community. Exceptional onsite management is in place if desired. Fantastic residence, rare opportunity, come take a look today!
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)
Listing Agent: Jesse Griffin (941-822-6165)
3010 GRAND BAY BLVD #482, LONGBOAT KEY, FL 34228
$1,845,000419 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
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.
3010 GRAND BAY BLVD #432, LONGBOAT KEY, FL 34228
$1,399,00050 Days on yellowkey MLS ID: A4683353
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2143 Built: 1999Monthly Fee: $175 Tax: $14,342 (2025)Community: Grand Bay 4Condo
Taxes:$14,342
Remarks: Step into the foyer from your private elevator and through chic double doors into this fully furnished Grand Bay masterpiece where drama meets elegance. Floor-to-ceiling glass sliders reveal a breathtaking panorama of the downtown city skyline, John Ringling Bridge, Harbourside golf course, and Sarasota Bay. The open floor plan seamlessly connects the living and dining areas to a versatile den—perfect as a media room or a third bedroom. Equipped with premium KitchenAid appliances, a Subzero and a central island, the kitchen includes an eating space for casual mornings. Wake up to panoramic bay views in the primary suite featuring private access to a massive wraparound terrace. The spa-like primary bath offers a garden soaking tub, dual vanities, a glass-enclosed shower and walk-in closet. The ensuite guest room ensures privacy and comfort, complete with its own stunning views of the water and greens and terrace access. Located behind the prestigious Longboat Key Club gates, residents enjoy double-gated security, Har-Tru tennis courts, a fitness center, a recently renovated Clubhouse and two heated pools. Grand Bay residents have private access to the Bay Isles Beach Club, all while being minutes away from the world-class shopping of St. Armands Circle and the cultural hub of downtown Sarasota.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Ian Addy, Pa (941-961-8850)
2295 GULF OF MEXICO DR #64S, LONGBOAT KEY, FL 34228
$625,000115 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)
775 LONGBOAT CLUB RD #808, LONGBOAT KEY, FL 34228
$2,195,00053 Days on yellowkey MLS ID: A4683021
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2122 Built: 1984 Tax: $17,930 (2025)Community: Beaches Of Longboat KeyCondo
Taxes:$17,930
Remarks: Behind the gates of the Longboat Key Club, this exceptional residence at The Beaches captures sweeping, unobstructed views of the Gulf of Mexico and its pristine shoreline, where vivid sunsets paint the horizon each evening. Perched on the eighth floor, this coveted Star floor plan is ideally positioned as a spacious end residence, offering 2,122 square feet of thoughtfully designed living space with 3 bedrooms and 3 full baths. Walls of glass frame panoramic water vistas and invite natural light to pour into the main living areas. Newly installed impact-rated sliders enhance both storm protection and seamless indoor-outdoor living, while oak engineered hardwood flooring flows beautifully through the living room, dining area, and kitchen, creating a warm yet sophisticated coastal aesthetic. The generous layout provides an effortless blend of comfort and refinement, with well-proportioned bedrooms and baths designed to accommodate both everyday living and gracious entertaining. The Beaches is recognized as one of the premier beachfront addresses within the Longboat Key Club, offering direct access to the sugar-white sands and turquoise waters of the Gulf. Residents enjoy an elevated level of service and amenities, including a 24-hour concierge, resort-style pool, fitness center, tennis courts, and impeccably maintained grounds. Ideally located on the southern end of Longboat Key, this gated community affords convenient access to the fine dining and boutiques of St. Armands Circle, the vibrant arts and culture of downtown Sarasota, and the exclusive offerings of the Longboat Key Club. This is a rare opportunity to secure a front-row seat to the Gulf and embrace the effortless elegance of Florida’s most sought-after coastal lifestyle.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Lenore Treiman (941-356-9642)
1145 GULF OF MEXICO DR #401, LONGBOAT KEY, FL 34228
$1,250,00088 Days on yellowkey MLS ID: A4678330
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1172 Built: 1980 Tax: $13,294 (2025)Community: Beachplace ICondo
Taxes:$13,294
Remarks: This highly desirable 4th floor corner residence at Beachplace boasts full direct views of the Gulf from almost every room. Renovated in a coastal contemporary style with long plank porcelain tile flooring throughout, the island lifestyle is readily apparent upon entering. The kitchen offers azure water views while meal prepping, stainless steel appliances, breakfast bar, granite counters and a closet pantry. The primary bedroom pampers owners with access to the covered terrace, spacious primary bathroom offering dual vanities and expansive water views. Highlights include impact windows, TWO Parking Spaces, new entry door, updated flooring in the bedrooms and new interior doors. With an excellent rental policy of 1 month minimum/12 times a year, there is healthy income potential - call for more details. Beachplace offers a 24-hour manned guard gate, heated swimming pool & spa, tennis courts, fitness center, clubhouse, on-site management and miles of pristine beach to relax, enjoy and explore. Conveniently located on the south end of Longboat Key just minutes from the fine dining and shopping on St. Armands Circle and a short drive over the bridge to the cultural hub of downtown Sarasota. Your Longboat Life awaits! RENTALS IN PLACE CONVEY WITH SALE.
1065 GULF OF MEXICO DR #402, LONGBOAT KEY, FL 34228
$845,000196 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.
605 SUTTON PL #102, LONGBOAT KEY, FL 34228
$485,00068 Days on yellowkey MLS ID: A4681310
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 992 Built: 1973Monthly Fee: $1,642 Tax: $6,934 (2024)Community: Sutton PlaceCondo
Taxes:$6,934
Remarks: Sutton Place is perfectly situated on the tropical grounds of the Longboat Harbour Community. The two-bedroom, two-bathroom unit features beautiful views of the Sarasota Bay, spacious living area, full-size kitchen with stainless steel appliances and granite countertops, dining area and 3 flat-screen TV’s. If the amenities on the interior of the condo aren’t enough – the community of Sutton Place boasts two heated swimming pools, fishing pier and game room, complete with billiards and ping-pong; along with a fitness center and clubhouse. Deeded beach access is located directly across the street.
Listing is courtesy of: SVN COMMERCIAL ADVISORY GROUP (941-387-1200)
Listing Agent: Larry Starr (941-914-6869)
1145 GULF OF MEXICO DR #603, LONGBOAT KEY, FL 34228
$1,779,00089 Days on yellowkey MLS ID: A4676554
0 Days Off yellowkey (back on 4/2/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1503 Built: 1980 Tax: $16,601 (2025)Community: Beachplace 1Condo
Taxes:$16,601
Remarks: Under contract-accepting backup offers. Penthouse level opportunity (floor 6) and fully renovated for its new owners convenience. Located in building one at Beachplace this 2 bedroom 2 bathroom condo is weeks away from completion of the scheduled building renovation. While the rest of the buildings in Beachplace begin their renovations, over the next several years, you will be able to enjoy (the 2nd largest floor plan B), for your personal use or rental income. The possibilities are unlimited and truly a very unique opportunity. The penthouse level gives you two balconies to enjoy the sparkling water and breathtaking views. The primary bedroom balcony and main living area balcony are separated by a 3/4 concrete wall to allow privacy to both guests and occupants of the spacious primary suite. Both balconies are accessed through impact-rated walls of glass that extend to each private terrace. These expansive beachfront balconies give you breathtaking sunsets and all the Gulf has to experience. Sit and relax while watching the wildlife and waves gently crash onto to the beach. This location on the southern end of Longboat Key gives your new beach home at Beachplace unmatched convenience, with opportunity for a rental return while waiting to fully retire and call this home. Beachplace offers residents 24-hour staffed security, on-site management, clubhouse, along with Har-Tru tennis courts, a modern fitness center, and heated swimming pool with spa. This location allows you quick access to St. Armands Circle, and the culture of Sarasota.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Bruce A Meyer, Pa (941-266-8152)
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