Location: Longboat Key
Keyword(s): Booker Middle
Keyword(s) Middle School: Booker Middle
Do Not Show Listings
571 RANGER LN, LONGBOAT KEY, FL 34228
$3,195,0007 Days on yellowkey MLS ID: A4699377
0 Days Off yellowkey (back on 7/10/2026)
Bed: 4 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2500 Built: 1969Monthly Fee: $21 Tax: $24,616 (2025)Community: Country Club ShoresSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$24,616
Elementary School: Southside Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Under contract-accepting backup offers. Welcome to an exceptional waterfront retreat in the highly sought-after Country Club Shores community on Longboat Key. Perfectly positioned on a deep-water canal with 100 feet of seawall, this beautifully remodeled 4-bedroom, 3-bath residence offers direct access to Sarasota Bay with no fixed bridges, making it an ideal home for boating enthusiasts. Designed for effortless coastal living, the open floor plan is filled with natural light and showcases elegant finishes throughout. The chef's kitchen features premium appliances, an oversized island, abundant custom cabinetry, and flows seamlessly into spacious living and dining areas overlooking the sparkling pool and tranquil waterfront. The private primary suite offers a peaceful retreat with a beautifully updated bath and generous closet space, while three additional bedrooms provide comfort and privacy for family and guests. Step outside to your tropical backyard oasis where boating, entertaining, and relaxation come together. The dock, boat lift, and Jet Ski lift are only two years old, providing immediate access to Sarasota Bay and the Gulf of Mexico. After a day on the water, enjoy the private heated pool or take a short stroll to the community's deeded Gulf beach access for spectacular sunsets and walks along Longboat Key's white sand beaches. This home has been meticulously maintained and thoughtfully updated with numerous recent improvements, including: New A/C (2 years) Pool equipment (2 years) Whole-house generator (approximately 1½ years) Upgraded electrical panel Washer & dryer (6 months) Updated irrigation system Enhanced exterior landscape lighting Boat lift and Jet Ski lift (2 years) Being sold furnished, this home offers an exceptional opportunity to begin enjoying the Longboat Key lifestyle immediately. Located just moments from the Longboat Key Club, championship golf, tennis, fine dining, St. Armands Circle, and downtown Sarasota, this is luxury waterfront living at its finest. Experience the perfect blend of boating, beach, and island living at 571 Ranger Lane. Waterfront • Canal Front • Deep Water • No Fixed Bridges • Boater's Paradise • Deeded Beach Access • Furnished • Country Club Shores • Longboat Key • Saltwater Canal • Dock • Boat Lift • Jet Ski Lift • Heated Pool • Luxury Waterfront Home • Gulf Access • Sarasota Bay • Coastal Living • Island Living • Move-In Ready
Listing is courtesy of: CORAL BAY REALTY LLC (941-465-6278)
Listing Agent: Dennis Perkins (941-465-6278)
1241 GULF OF MEXICO DR #408, LONGBOAT KEY, FL 34228
$3,200,00039 Days on yellowkey MLS ID: A4695733
2 Days Off yellowkey (back on 7/10/2026)
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2965 Built: 1996 Tax: $29,387 (2025)Community: Water Club 01 At Longboat KeySpa: YesCondo
Taxes:$29,387
High School: Sarasota High
Remarks: Under contract-accepting backup offers. Water Clubs most exquisitely renovated residence just became available for the first time! Meticulously reimagined from the studs up, this “Beach Beauty” immerses you in the essence of the Gulf below, every detail from the Azure toned palette to the warm honey finishes evoke a serene coastal escape with walls of windows frame the sweeping vistas from Bay to Beach while expansive terraces flow seamlessly between indoor and outdoor living - perfect for elegant entertaining or peaceful solitude. This modified “Dover” renovated floor plan Is located in the highly desirable end “8” stack which has amazing full gulf and bay views, the advantage of the private wrap around terraces elevate you above the lush tropical canopy to be soothed by remarkable natural light and uninterrupted vistas. Rich wide plank wood flooring sets a warm sophisticated tone throughout this impeccably designed residence. Only the finest finishes were selected, with designer fixtures, custom details and elegant appointments. Bespoke lighting creates a captivating ambience while custom remote shades and luxurious sheer drapery blend harmoniously with the curated furnishings. Offered beautifully “turnkey furnished” every detail is already in place allowing you to begin enjoying this extraordinary coastal retreat from the moment you arrive! Flowing seamlessly from the great room the stunning open concept kitchen is designed for both gourmet cooking and gracious entertaining. At its heart, a chef inspired island invites friends and family to join in creating culinary creations, Wine enthusiasts will appreciate the custom Euro wine cave perfectly positioned to keep your favorite vintages at hand for impromptu gatherings or elegant dinners. The exceptional kitchen is appointed with premium Thermador built-in appliances, induction cooktop, creamy quartz countertops, custom cabinetry with convenient pantry pullouts, and thoughtful storage throughout. Serving as a true sanctuary, the primary suite exudes the ambience of an exclusive spa retreat with a beautifully appointed vestibule separating the walk-in closet from the private luxurious bathroom. The primary bath with walk-in shower flows into the elegant sophisticated “boudoir” appointed with bespoke fixtures, and luxurious bedding and linens. Step out to the private terrace where the sounds of the Gulf will lull you to sleep. The 2nd Guest ensuite has an amazing Bay view terrace to enjoy the twinkling lights across the Bay at night. The generous walk-in closet is stocked with exquisite bedding, and towels to make your guests feel pampered. The full bath includes a walk-in shower, quartz vanity, and elevated lighting. The 3rd bed/den is a great escape for the kids or a private yoga studio - it segues smartly with the 3rd bathroom right down the hall for convenience, decorated with the same style and quality of décor and finishes. The Water Club is known for its full 24 hour concierge service, resort style living, offering children’s pool, 3 spas, 4 har-tru tennis courts, a Mediterranean spa clubhouse with fitness center, steam and sauna, library, many social spaces and Water Club is “pet-friendly”. Every corner of this amazing property has been reimagined with the finest materials and thoughtful design - It’s truly an artistic creation you must see to appreciate. Call now for a private showing.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Kathy Callahan (941-900-8088)
4127 GULF OF MEXICO DR #N102, LONGBOAT KEY, FL 34228
$4,700,000168 Days on yellowkey MLS ID: A4680618
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3521 Built: 2007 Tax: $30,723 (2025)Community: La FirenzaSpa: NoCondo
Taxes:$30,723
Remarks: Spectacular Gulf of Mexico views define this exceptional three-bedroom, three-and-a-half-bath residence that lives like a single-family home. A large wraparound terrace with a built-in grill offers seamless indoor-outdoor living, and private steps leading directly to the sandy beach – perfect for sunset entertaining or morning walks along the shore. Enter the home through a private elevator into a formal foyer with double door entry into the residence. The gracious living room is framed by expansive windows showcasing endless water views and exceptional sunsets flowing effortlessly to a built-in wet bar complete with wine refrigerator, ice maker, and a dedicated desk area—ideal for entertaining or casual work-from-home moments. A formal dining room with elegant ceiling detail makes hosting a dinner party a treat. Plantation shutters throughout the residence add a coastal and private touch. The gourmet kitchen is designed for both function and style, offering a large island for gathering, side-by-side Sub-Zero refrigerator and freezer, Wolf gas cooktop, Wolf oven with warming drawer, generous pantry, and a cozy desk area for browsing favorite recipes. A large center island and charming breakfast nook are the perfect spots for morning coffee or casual meals. Adjacent to the kitchen, the inviting keeping room opens to a private east-facing terrace with beautiful sunrise and views of Sarasota Bay. The expansive owner’s suite is a true retreat, featuring its own breakfast bar with sink and refrigerator for enjoying morning coffee while overlooking the Gulf. Two oversized, custom-built walk-in closets provide exceptional storage. The spa-inspired bath includes double vanities, a glass-enclosed shower, a private water closet with bidet, and refined finishes throughout. Two en-suite guest bedrooms with large custom-built closets open onto a private terrace with views of Sarasota Bay, ensuring comfort and privacy for family and guests alike. This rare beachfront residence combines luxury, privacy, and the ease of coastal living, all with breathtaking views and thoughtfully designed spaces for everyday enjoyment and elegant entertainment. Residents of La Firenza enjoy a boutique, gated setting with private beach access, a heated beachfront pool and spa, fitness facilities and secure garage parking.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Kim Ogilvie (941-951-6660)
521 BAYPORT WAY #521, LONGBOAT KEY, FL 34228
$619,90033 Days on yellowkey MLS ID: TB8518960
REDUCED by $29,100 (4.5%) on 06/24/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1980Monthly Fee: $1,978 Tax: $5,669 (2025)Community: Bayport Bch & Ten Ph ACondo
Taxes:$5,669
Remarks: We are offering an exceptional investment opportunity at Bayport Beach & Tennis Club. Unit 521 is PRICED BELOW a recent June 2026 independent appraisal and currently the lowest-priced residence in the Bayport Beach & Tennis Club complex, we feel this beautifully updated condominium represents one of the best values on Longboat Key for a primary residence, seasonal retreat, vacation home, or investment property. Features include impact-resistant windows and sliding glass doors, City-permitted interior remodeling, a newer air conditioning system, covered parking, private storage, and numerous thoughtful upgrades throughout. The recent June 2026 independent appraisal, City permit records, association budget, reserve information, and HOA documents are available electronically upon request. Discover the essence of coastal resort living within Bayport's beautifully landscaped 27-acre Gulf-to-Bay community featuring 1,200 feet of private deeded Gulf of Mexico beachfront, direct Sarasota Bay access with a fishing pier and kayak launch, mature tropical landscaping, scenic walking trails, and an outstanding collection of resort-style amenities. Residents enjoy a heated Junior Olympic lap pool, four Har-Tru tennis courts, fitness center, clubhouse, community room, kayak launch and storage, professional on-site management, and one of Longboat Key's most desirable waterfront lifestyles. Conveniently located just minutes from Publix, Ace Hardware, Pickle ball facilities, waterfront dining, boating, championship golf, St. Armands Circle, The Ringling Museum, dog parks, and the cultural attractions of downtown Sarasota, Bayport offers the perfect balance of island tranquility and everyday convenience. Whether you're searching for a full-time residence, seasonal getaway, vacation home, or long-term investment, this move-in-ready residence offers exceptional value in one of Florida's premier Gulf-to-Bay communities. Experience the relaxed elegance, natural beauty, and resort lifestyle that have made Bayport Beach & Tennis Club one of Longboat Key's most sought-after addresses. Come experience why so many residents say that living at Bayport isn't just owning a home—it's embracing a year-round island resort lifestyle that others only experience on vacation.
Listing is courtesy of: PERSONAL REALTY ADVISERS (727-317-7653)
Listing Agent: Rob Coscia (239-770-2683)
2600 HARBOURSIDE DR #I-09, LONGBOAT KEY, FL 34228
$300,000323 Days on yellowkey MLS ID: A4663346
Bed: Bath: 0.0 Built: 1985Monthly Fee: $402 Tax: $2,174 (2025)Community: Bay IslesDock-Rackominium
Taxes:$2,174
Remarks: The middle pier, right in front at Longboat Key Club! I-09, a 60 ft x 21 ft. slip in the marina. This is the only north-south pier in the marina; plenty of deep water and cool breezes. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and discreet, on-site maintenance and concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 55 LOA; beam depends on the vessel. Call to discuss!
Listing is courtesy of: LBRE LLC (941-383-8383)
Listing Agent: Jennifer Wilson (941-809-7592)
617 WESTON POINTE CT, LONGBOAT KEY, FL 34228
$3,100,00010 Days on yellowkey MLS ID: A4697745
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4395 Built: 1994Monthly Fee: $708 Tax: $27,075 (2025)Community: Weston PointeSpa: NoSingle Family
Taxes:$27,075
Remarks: Welcome to **617 Weston Pointe Court**, where timeless elegance meets the Florida waterfront lifestyle. Nestled within one of Longboat Key's most desirable gated golf communities, this exceptional **four-bedroom, five-bathroom** residence offers an extraordinary blend of luxury, privacy, and direct boating access to the Gulf. From the moment you step inside, you'll be captivated by the expansive open floor plan, soaring ceilings, and breathtaking views overlooking the tranquil canal. Designed for both everyday living and effortless entertaining, the spacious great room flows seamlessly into the gourmet kitchen and dining areas, creating a bright and inviting atmosphere throughout the home. The thoughtfully designed floor plan features a luxurious primary suite and two additional bedrooms on the main level, while the upstairs loft provides a versatile living space accompanied by an additional guest bedroom, offering comfort and privacy for family and visitors alike. At the heart of the home lies an incredible private courtyard oasis. The sparkling pool creates a resort-style setting between the main residence and a detached cabana complete with its own kitchenette and full bathroom—an ideal space for overnight guests, a private office, fitness studio, or poolside entertaining. For boating enthusiasts, this property truly stands apart. The **privately owned boat slip conveys with the home**, offering exceptional value and convenience. Positioned as the **last slip on the left**, it provides one of the easiest locations in the marina for entering and exiting with your boat, making every trip on the water effortless. The slip is equipped with a **boat lift**, and from your dock, it's approximately **15 minutes through the scenic canal to the open waters of the Gulf**, allowing you to spend less time navigating and more time enjoying life on the water. Whether you're hosting elegant gatherings around the courtyard pool, enjoying peaceful waterfront sunsets, or setting out for a day of boating, this remarkable Longboat Key residence offers the perfect combination of luxury, comfort, and coastal living. Don't miss this rare opportunity to own an exceptional waterfront home complete with a transferable private boat slip in one of Longboat Key's most sought-after communities. Schedule your private showing today and experience Florida waterfront living at its finest.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Jason Kranz, Pa (352-446-6001)
2120 HARBOURSIDE DR #623, LONGBOAT KEY, FL 34228
$975,000116 Days on yellowkey MLS ID: A4686721
REDUCED by $120,000 (11.0%) on 06/30/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2031 Built: 1988Monthly Fee: $137 Tax: $11,079 (2025)Community: Fairway Bay AtriumSpa: YesCondo
Taxes:$11,079
Remarks: Step into coastal elegance in this fully renovated three-bedroom, two-bathroom Fairway Bay residence, where every detail has been thoughtfully reimagined. A charming private lanai and seating area welcome you before entering the unit, setting the tone for relaxed waterfront living. Inside, an open-concept layout seamlessly blends the kitchen, dining, and living spaces, creating a bright, airy environment perfect for both entertaining and everyday comfort. The gourmet kitchen is outfitted with GE Profile appliances, custom soft-close cabinetry, and ample storage, offering both style and functionality. The primary suite is a serene retreat featuring a spacious walk-in closet, additional storage, and a beautifully updated en-suite bath with a large walk-in shower. From both the living room and the primary suite, step onto the expansive north-facing balcony to take in the tranquil Sarasota Bay views, where you can enjoy the morning sunrise and the soft glow of the evening sky. The second bedroom is generously proportioned and easily accommodates a king-size bed, creating a luxurious space for guests. The third bedroom is also spacious, complete with a custom built-in, ideal for a guest room, home office, or flexible living area. A thoughtfully designed guest bath ensures privacy and convenience for family or visitors. This unit also includes the ease and security of one covered parking space beneath the building. Fairway Bay residents enjoy an exceptional suite of amenities including two heated pools, a spa, a clubhouse, a fitness center, tennis and pickleball courts, and private beach access on Longboat Key. With the shops, dining, and vibrant lifestyle of St. Armands Circle just minutes away, this residence combines the best of convenience and refined waterfront living.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
3040 GRAND BAY BLVD #213, LONGBOAT KEY, FL 34228
$1,460,000178 Days on yellowkey MLS ID: A4678941
REDUCED by $90,000 (5.8%) on 07/09/2026
Bed: 2 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2550 Built: 1996 Tax: $8,474 (2025)Community: Grand Bay 2Spa: YesCondo
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. Extremely well managed building- all improvements have been completed!
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Dianne Anderson (941-350-3513)
3301 BAYOU RD, LONGBOAT KEY, FL 34228
$1,250,00071 Days on yellowkey MLS ID: A4692818
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2827 Built: 1993Monthly Fee: $104 Tax: $12,771 (2025)Community: Bay IslesSingle Family
Taxes:$12,771
Remarks: Located within the gated and highly desirable community of Bay Isles on Longboat Key, this 4 bedroom, 3 bathroom pool home encompasses 2827 square feet of living space. The residence features a functional and spacious floor plan, including a well-appointed bedroom layout, an open kitchen and family room combo, and a formal living and dining room combo. This property is priced competitively, offering an exceptional opportunity for a buyer or investor to come in and renovate the home with their own personal style and modern finishes. The outdoor living area features a private pool, providing a quiet retreat within a stunning waterfront community. Bay Isles residents enjoy a premier island lifestyle with access to a private beach area and cabana, while separate memberships are available for those interested in world-class golf or the local marina. The location is ideal for enjoying the best of the Florida Gulf Coast, situated in close proximity to local restaurants, boutique shopping, and the famous St. Armand's Circle. Whether you are looking for a primary residence or a seasonal getaway, this home serves as the perfect canvas to create a custom masterpiece in one of Longboat Key's most sought-after enclaves.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Michele Tanner (941-894-5603)
1005 BOGEY LN, LONGBOAT KEY, FL 34228
$2,999,000171 Days on yellowkey MLS ID: A4680006
REDUCED by $301,000 (9.1%) on 07/08/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3624 Built: 2017Monthly Fee: $21 Tax: $19,847 (2025)Community: Country Club ShoresSpa: YesSingle Family
Taxes:$19,847
Remarks: Nestled along a serene canal just a short ride to beautiful Sarasota Bay, this custom-built John Cannon home offers the perfect blend of luxury, comfort, and coastal living. This two-story, 4-bedroom residence features an open floor plan designed for both relaxation and entertaining. Each bedroom is ensuite, providing privacy and comfort for family and guests alike. Enjoy gathering in the spacious area or entertaining outdoors with a heated pool and spa, a fully equipped outdoor kitchen, and a private dock with a boat lift for effortless access to the water. The home also includes an elevator- ideal for transporting luggage and groceries- and a generous 3- garage with abundant storage. Conveniently located near St. Armands Circle and downtown Sarasota, this property offers easy access to fine dining, shopping , and white-sand beaches, making it a true coastal retreat with every modern amenity.
Listing Agent: Michael Nink, Pa (941-914-2805)
3010 GRAND BAY BLVD #493, LONGBOAT KEY, FL 34228
$1,475,000280 Days on yellowkey MLS ID: A4668143
REDUCED by $404,000 (21.5%) on 07/06/2026
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2550 Built: 1999 Tax: $16,976 (2025)Community: Grand Bay 4Spa: YesCondo
Taxes:$16,976
Remarks: One or more photo(s) has been virtually staged. Perched just one floor below the penthouse in the sought-after Grand Bay IV community on Longboat Key, this 2,550-sq.-ft. Cayman floor plan offers an exceptional opportunity to enjoy the Grand Bay lifestyle immediately. With ideal north–south exposure, this residence captures breathtaking sunrises over Sarasota Bay and stunning Gulf sunsets from two expansive terraces. Walls of glass and abundant natural light enhance the open-concept layout, which includes 2 bedrooms, 2.5 baths, and a den that can easily be reconfigured to include a walk-in closet for a 3rd bedroom. The primary suite opens directly to the Bayfront terrace, the second bedroom offers an en-suite bath and private Gulf-view balcony, and the den, kitchen, and third bedroom share access to a second terrace for effortless indoor-outdoor living. Two prime, side-by-side parking spaces on the upper main level sit conveniently next to the elevator, leading to a private elevator foyer. Residents of Grand Bay enjoy world-class amenities including 24-hour security, a clubhouse with library and game room, fitness center, tennis and pickleball courts, two heated pools and a spa, and deeded access to the exclusive Bay Isles Beach Club.
455 LONGBOAT CLUB RD #PH8, LONGBOAT KEY, FL 34228
$2,700,90021 Days on yellowkey MLS ID: A4697519
2 Days Off yellowkey (back on 7/8/2026)
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 2780 Built: 1990 Tax: $23,862 (2025)Community: PierreCondo
Taxes:$23,862
Remarks: Under contract-accepting backup offers. PENTHOUSE LIVING AT THE PIERRE – LUXURY GULF-FRONT RESIDENCE IN LONGBOAT KEY CLUB Welcome to The Pierre, an exclusive Gulf-front community featuring just 66 luxury residences nestled behind the private gates of the renowned Longboat Key Club. This beautifully renovated eighth-floor penthouse residence offers breathtaking panoramic views from every room, showcasing the tranquil bay waters, spectacular Gulf sunsets, and the sparkling city skyline. Designed to maximize natural light and capture the beauty of its surroundings, expansive windows frame unforgettable vistas throughout the home. Thoughtfully crafted for both everyday living and elegant entertaining, this exceptional residence features three spacious bedrooms, three-and-a-half baths, and a gourmet kitchen equipped with premium Thermador appliances, abundant cabinetry, and generous workspace for the discerning chef. The luxurious primary suite provides a peaceful retreat with stunning water views, while the additional guest suites allows for comfort and privacy for family and visitors. Residents of The Pierre enjoy an impressive collection of resort-style amenities, including: • Direct private beach access • Beachfront heated pool and spa • Fitness center • Tennis courts • Newly renovated lobby and common areas • Club gathering room and meeting facilities • 24-hour guarded security • On-site professional management Ownership also includes two private garage parking spaces, a secured storage area, and access to private guest suites available for visiting family and friends on a nominal rental basis. For those seeking an elevated lifestyle, membership opportunities at the renowned Longboat Key Club provide access to championship golf courses, world-class tennis facilities, spa and wellness services, exceptional dining venues, beach services, and a vibrant social calendar (membership subject to application and availability). Ideally located near St. Armands Circle and vibrant Sarasota, you'll enjoy convenient access to fine dining, boutique shopping, arts and cultural attractions, and some of Florida's most beautiful beaches. This is a rare opportunity to own an extraordinary Gulf-front penthouse in one of Longboat Key's most sought-after luxury communities. Schedule your private showing today and experience the unparalleled lifestyle that awaits at The Pierre.
Listing is courtesy of: REAL ESTATE BOUTIQUE LLC (941-726-8061)
Listing Agent: Maria Atkins (941-726-8061)
803 BAYPORT WAY #803, LONGBOAT KEY, FL 34228
$775,000122 Days on yellowkey MLS ID: A4686552
1 Days Off yellowkey (back on 5/14/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1456 Built: 1981 Tax: $6,376 (2025)Community: Bayport Bch & Ten Ph ECondo
Taxes:$6,376
Remarks: Under contract-accepting backup offers. Welcome to the true tropical oasis of Bayport Beach & Tennis Club, a Longboat Key Gulf to Bay community. Bayport was designed by Tim Siebert, one of the founding architects of the renowned Sarasota School of Architecture and is recognized for its award-winning, timeless design. Bayport offers 27 lushly landscaped acres with 1,200 feet of private beach. This tastefully renovated second-floor unit offers two expansive bedrooms and two beautiful bathrooms and comes fully turn-key. This unit was curated with attention to detail and functionality in mind. The kitchen offers plenty of storage, stainless steel appliances, quartz countertops and beautiful accent details. Enjoy three patios that allow for great indoor/outdoor living. Fully equipped with Hurricane impact doors and windows. One under building parking space included, along with a locked storage closet - perfect for bikes and beach gear. When not at the beach, enjoy the meticulously kept nature trails, landscaped grounds and wildlife. Just steps away from the well appointed clubhouse is equipped with a Junior-Olympic sized heated pool, four har-tru tennis courts, a fitness center and more. In addition, Bayport residents are proud of their active social and recreational calendar. Water enthusiasts can utilize the secluded fishing pier that stretches out onto Sarasota Bay; to fish, watch the sunrise, the Manatees swim or the Egrets wading among the mangrove trees. Residents also benefit from conveniently located on-site paddle board and kayak launch and storage areas. Bayport residents enjoy an array of restaurants locally, and the convenience of a nearby supermarket, pharmacy and boutique shops. Recreational enthusiasts also benefit from the nearby Bayfront Park which offers a popular pickle-ball program, dog park and other bayside activities. The nearby Longboat Key Club offers private access to championship waterfront golf, extensive leisure activities and boating facilities. Within minutes, one can access the famous St Armand's Circle with its exceptional shopping and dining amenities. From there, cross the iconic Ringling Bridge to downtown Sarasota, which is well known for world-class theater, culture and dining.
Listing Agent: Alexis Smith-Frady (352-225-1724)
3271 BAYOU RD, LONGBOAT KEY, FL 34228
$1,995,00042 Days on yellowkey MLS ID: TB8515918
0 Days Off yellowkey (back on 7/7/2026)
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3059 Built: 2014Monthly Fee: $104 Tax: $27,748 (2025)Community: Bay IslesSingle Family
Taxes:$27,748
Remarks: Under contract-accepting backup offers. Nestled behind the gates of prestigious Bay Isles on Longboat Key, this exceptional residence offers over 3,000 square feet of thoughtfully designed living space surrounded by lush tropical landscaping and just moments from the Gulf of Mexico. Combining timeless architecture, spacious interiors, and resort-style outdoor living, this home delivers the privacy and elegance that define the Longboat Key lifestyle. A grand entry welcomes you into an open and inviting floor plan featuring soaring ceilings, abundant natural light, and generous living and entertaining spaces. The expansive great room flows seamlessly into the dining area and well-appointed kitchen, complete with ample cabinetry, extensive counter space, and a convenient wet bar for effortless entertaining. The first-floor primary suite serves as a private retreat with a spacious bedroom, large walk-in closet, and luxurious en-suite bath. Additional guest bedrooms are thoughtfully positioned for privacy and comfort, while the second floor offers a private guest suite with balcony access—perfect for visitors seeking their own space and enjoying tropical views. Designed for year-round enjoyment, the screened outdoor living area is a true highlight. Relax poolside in the sparkling heated pool and spa, entertain under the covered lanai, or unwind amidst the lush tropical surroundings that create a secluded backyard oasis. Located within the highly sought-after Bay Isles community, residents enjoy 24-hour gated security, beautifully maintained grounds, and exclusive access to the private Bay Isles Beach Club on the Gulf of Mexico. Just minutes away are the Longboat Key Club's championship golf courses, tennis facilities, marina, waterfront dining, boutique shopping, and renowned St. Armands Circle. Offering the perfect blend of luxury, privacy, and coastal convenience, this exceptional Longboat Key residence presents a rare opportunity to enjoy one of Sarasota's most desirable island lifestyles.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Robert Johnson (813-364-2250)
600 PUTTER LN, LONGBOAT KEY, FL 34228
$9,400,000560 Days on yellowkey MLS ID: A4633484
REDUCED by $1,100,000 (10.5%) on 05/19/2026
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 5982 Built: 2017Monthly Fee: $17 Tax: $69,287 (2025)Community: Country Club Shores, Unit 5, Sec 3Spa: YesSingle Family
Taxes:$69,287
Remarks: Welcome to Paradise on Longboat Key. This coastal modern home is located on the direct bayfront with a total of 270 feet of waterfront on an oversized lot consisting of 18,290 square feet. As you enter the home, your first view is a serene and expansive view of Sarasota Bay all the way from the Ringling Museum to Downtown Sarasota and the Ringling Bridge. Enjoy different types of boating as the dock includes 2 jet ski lifts and a 13,000 pound boat lift. With plenty of interior space, there are 5 bedrooms and 5 baths plus a dedicated office/den, family room and game room. Every bedroom is filled with bay views. As an added advantage, guests have their own space upstairs that includes a kitchenette. Outfitted with an elevator that stops at every floor, including the three car garage, convenience is just a step away. To enjoy the views outside, there is an outdoor surround lanai with disappearing screens, fireplace and summer kitchen. Large covered terraces on both levels provide views of beautiful sunrises over Sarasota Bay and Downtown Sarasota.
Listing is courtesy of: FLORIDA CAPITAL REALTY (786-953-5870)
Listing Agent: Kathleen Callender (941-321-3115)
2301 GULF OF MEXICO DR #45N, LONGBOAT KEY, FL 34228
$625,00011 Days on yellowkey MLS ID: A4698596
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970 Tax: $4,789 (2025)Community: Islander Club Of LongboatCondo
Taxes:$4,789
Remarks: Experience exceptional Gulf-front living in this beautifully maintained two-bedroom, two-bath residence at the highly desirable Islander Club on Longboat Key. Enjoy peaceful views of the manicured grounds, entrance, and tennis courts from the expansive wraparound terrace offering more than 60 feet of private outdoor living space—perfect for relaxing or entertaining. Inside, the light-filled open floor plan features floor-to-ceiling sliding glass doors, a well-appointed kitchen with KitchenAid appliances, and spacious living and dining areas. The primary suite offers terrace access and an en-suite bath, while the guest bedroom provides comfortable accommodations for visitors or a home office. Recent updates include hurricane-impact windows and doors, a Bosch HVAC (2016), water heater (2020), in-unit humidistat, assigned parking, and extensive community improvements including new elevators, roof, porte cochère, fitness center, clubhouse, locker rooms with saunas, recreation room, and landscaping. End-window replacements have also been ordered. The Islander Club offers over 400 feet of private Gulf beach frontage, a heated beachfront pool, fitness center, Har-Tru tennis court, two pickleball courts, two fishing piers, on-site management, and 24/7 maintenance staff. Just minutes from St. Armands Circle and Downtown Sarasota, this is your opportunity to enjoy the very best of Longboat Key beachfront living.
Listing Agent: Paul Bachmann (813-786-6242)
1915 HARBOUR LINKS CIR #6, LONGBOAT KEY, FL 34228
$1,950,000106 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
Remarks: Gated Bay Isles Villa with Private Beach Access on Longboat Key! Discover effortless island living in sought-after Emerald Pointe South, where privacy, convenience, and the coastal lifestyle come together. This beautifully maintained villa offers an open, light-filled floor plan with spacious living and dining areas that flow to a private screened lanai surrounded by lush tropical landscaping. The first-floor primary suite features dual walk-in closets and a generous en-suite bath with dual vanities, soaking tub, and separate shower. The kitchen offers solid surface countertops, ample cabinetry, a breakfast nook, and newer appliances including the range, dishwasher, and microwave. Upstairs, two guest suites with private baths provide the perfect retreat for family and visitors. Residents enjoy the security of gated Bay Isles plus exclusive access to the private Bay Isles Beach Club on the Gulf of Mexico. Minutes from St. Armands Circle, downtown Sarasota, golf, marinas, shopping, and waterfront dining — this villa delivers the best of Longboat Key living. Maintenance-free, gated, beach-access living — your island retreat awaits!
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Cathy Palmer (678-524-1104)
3527 FAIR OAKS LN, LONGBOAT KEY, FL 34228
$2,550,00056 Days on yellowkey MLS ID: A4694532
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4154 Built: 1994Monthly Fee: $833 Tax: $22,710 (2025)Community: Queens HarbourSpa: YesSingle Family
Taxes:$22,710
Remarks: Experience refined coastal luxury in this impeccably renovated 4,154-square-foot golf course estate, ideally positioned within the exclusive Queens Harbour enclave of gated Bay Isles on Longboat Key. This extraordinary two-story residence offers 4 bedrooms, 4.5 bathrooms, and an elegant open floor plan thoughtfully curated with exquisite finishes and designer details throughout. Extensive recent enhancements include a newer roof (2021), new panoramic pool cage with picture-frame screening (2025), new hurricane Armor Screen shutters protecting every opening (2025), and a custom two-person Pneumatic Vacuum elevator, along with numerous additional upgrades and improvements. Dramatic two-story windows fill the expansive great room and chef’s kitchen with natural light while showcasing breathtaking views of the sparkling pool, serene lake, lush landscaping, majestic oak trees, and the manicured fairway. Designed for both everyday living and entertaining, the gourmet kitchen is a culinary masterpiece, complete with a large gas range, dual ovens, solid wood cabinetry, abundant counter space, and a charming breakfast nook framed by bay windows overlooking the pool and golf course. The luxurious first-floor owner’s retreat offers Brazilian cherry wood flooring, vaulted ceilings, French doors opening to the lanai, dual walk-in closets, and a spa-inspired bathroom. Two additional guest bedrooms on the main level are connected by a beautifully appointed Jack-and-Jill bathroom. Outdoor living is equally exceptional, with an oversized pool and spa set within a spacious private lanai designed for relaxation and entertaining while enjoying tranquil sunsets over the lake and golf course. Residents of Queens Harbour enjoy maintenance-free living, a private community pool, and exclusive access to the Bay Isles Beach Club with deeded Gulf beach access. Ideally located near the Longboat Key Club Harbourside golf course, tennis facilities, and the Moorings Yacht Club, this residence embodies the finest in Longboat Key luxury living.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Miriam Pearson (941-726-4687)
806 BAYPORT WAY #806, LONGBOAT KEY, FL 34228
$949,000110 Days on yellowkey MLS ID: TB8489326
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1392 Built: 1981 Tax: $5,917 (2025)Community: Bayport Bch & Ten Ph ECondo
Taxes:$5,917
Remarks: Welcome to this beautifully appointed ground floor residence that combines modern elegance with functional design. Newly remodeled in 2025, this residence features high-end finishes and modern amenities, making it an ideal retreat for those seeking luxury in a serene environment. Upon entering, you are greeted by a bright and spacious interior filled with natural light, thanks to strategically placed additional windows featured in corner/end units of this community. The subtle elegance of the interior is complemented by sleek flooring that enhances the flow from room to room. The kitchen is a true highlight, featuring quality cabinetry, elegant quartz counters, and modern stainless-steel appliances, which allow a harmonious flow, delivering both functionality and sophistication. The open-concept layout continues through the dining and living areas, combining a blend of textures and stylish finishes to cohesively create an environment of relaxed elegance. An abundance of natural light floods this space through large retractable sliding glass doors, which provide the option of extending the outdoors in. A private outdoor patio showcases a beautiful backdrop of lush tropical landscaping, adding to the property’s overall appeal. The bedrooms within the property are thoughtfully designed, each offering generous space and natural light. The primary suite offers a restful retreat, complete with an ensuite bathroom featuring modern fixtures and thoughtful design, ensuring comfort and privacy. This property will continue to amaze, as beauty extends beyond its walls into an amenity-rich community of 27 acres of picturesque tropical landscaping. This gulf-to-bay community offers an active island lifestyle with 4 Har-Tru tennis courts, a Jr. Olympic sized (heated) pool, private fishing pier, kayak facilities, Bocce court, and amazing nature trails. A distinct advantage and unique selling point of this property is its proximity to a private, deeded beach. This property offers future owners not just exclusive beach access, but a revitalizing retreat amidst the hustle and bustle of life—truly a valuable benefit that amplifies the charm of this residence. Close to local amenities yet precisely positioned to offer privacy and quietude, this property represents an excellent opportunity for discerning buyers. Experience the best of coastal living in this beautiful home, where modern comfort meets natural beauty. Welcome home!
Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA (813-684-9500)
Listing Agent: Antonietta Car (813-684-9500)
1445 GULF OF MEXICO DR #101, LONGBOAT KEY, FL 34228
$1,180,000140 Days on yellowkey MLS ID: A4684021
REDUCED by $15,000 (1.3%) on 06/25/2026
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2092 Built: 1982 Tax: $11,749 (2025)Community: Players Club IiiSpa: YesCondo
Taxes:$11,749
Remarks: Step into this highly desirable corner residence featuring three bedrooms, three full baths, and an expansive 36’ x 11’ sunroom at The Players Club. You’ll immediately be drawn to the impressive 31-foot balcony, offering sweeping views of the resort-style pool, lush, landscaped grounds, and breathtaking sunsets over the Gulf of Mexico. The outdoor space is perfect for alfresco dining, entertaining friends, or simply enjoying the tranquil Gulf breezes. Inside, the sun-filled kitchen is thoughtfully designed with custom cabinetry and a built-in breakfast table that expands both workspace and storage. It flows seamlessly into the main living and dining areas, creating a warm and open environment for entertaining or daily living. Just off the kitchen, elegant French doors open to a generous multipurpose sunroom that can serve as a home office, reading retreat, casual lounge, or even a fourth bedroom for guests. The owner’s suite provides a private sanctuary with a spa-inspired bathroom featuring a soaking tub, separate glass-enclosed shower, dual vanities, and a spacious walk-in closet. The second bedroom functions as a true secondary master, complete with dual sinks, a full vanity, and a fitted walk-in closet, offering comfort and privacy for family or visitors. A third bedroom adds flexibility for guests, workspace, or hobbies. A unique feature of this residence is the private garage, offering rare security and convenience for residents, plus an additional covered parking space underneath the building for extra guest or secondary vehicle use. Set on 11 acres of beachfront with 560 feet of Gulf frontage, The Players Club offers abundant green space, four Har-Tru tennis courts, a 70-foot heated saltwater pool, spa, fitness center, renovated clubhouse with catering kitchen, outdoor grilling areas, putting green, on-site management, and fully funded reserves. Just minutes from St. Armands Circle, downtown Longboat Key, and Longboat Key Club, with championship golf, premier tennis, and a deep-water marina, this corner residence blends privacy, convenience, and resort-style coastal living. Units with this versatile layout and resort-ready features are highly sought after. Offered partially furnished. Seller is willing to discuss a subsidy on the quarterly condominium fee for reserve increase over the next two years!
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