Location: Longboat Key
Keyword(s): Booker Middle
Keyword(s) Middle School: Booker Middle
Do Not Show Listings
370 GULF OF MEXICO DR #432, LONGBOAT KEY, FL 34228
$1,315,0001 Day on yellowkey MLS ID: A4696946
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2900 Built: 1994 Tax: $9,030 (2025)Community: Tangerine Bay ClubSpa: NoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,030
Elementary School: Southside Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: PENTHOUSE. Delight in scenic views of Sarasota Bay in this custom-designed, rare 4 bedroom, 4.5 bathroom in the gated resort-style Tangerine Bay community on the southernmost tip of Longboat Key. The residence is only minutes from St. Armand's Circle, across the street from the Longboat Key Club, and a short driving distance to the Bay Isles Beach Club and vibrant downtown Sarasota. Filled with abundant natural light, the spacious condominium features soaring ceilings, a great room with gas fireplace, marble foyer and gallery for displaying artwork, and private gated courtyard. All bedrooms are ensuite. New sliding glass doors in the primary suite and new glass window in the great room open to a tiled terrace where you can start your day with a cup of coffee while watching the sunrise over the lagoon and Bay. An additional west-facing terrace upstairs boats golf course and sunset views. The well-equipped kitchen includes stone counters, breakfast bar, large pantry and morning room. There is also a fully enclosed two-car garage with plenty of storage space as well as two AC units in the condominium. The Tangerine Bay Club community boasts beautifully manicured walking paths, amid newly planted tropical greenery as well as many amenities, including a pool with waterfalls, fitness center, a tennis/pickleball court, plus a day boat dock and fishing pier on the Bay. Residents have the option of joining the Beach Club (normally reserved for only Bay Isles residents) on the Gulf of America.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Steve Walter (941-809-0907)
626 BUTTONWOOD DR, LONGBOAT KEY, FL 34228
$4,495,0002 Days on yellowkey MLS ID: A4696767
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4106 Built: 2026Monthly Fee: $50 Tax: $4,789 (2025)Community: Longboat Shores RevSpa: YesSingle Family
Taxes:$4,789
Remarks: Experience the pinnacle of coastal living in this exceptional new construction waterfront residence, ideally situated in the heart of Longboat Key. Perfectly positioned across from the community marina with direct boating access to the Gulf of Mexico, this move-in-ready home offers an extraordinary blend of modern elegance, superior craftsmanship, and the relaxed sophistication of island life. Spanning 4,106 square feet, this thoughtfully designed residence features 4 spacious bedrooms, a private office/den, and 4 luxurious bathrooms, creating an ideal setting for both everyday living and entertaining. Finished floor elevation above base flood elevation, the home provides added peace of mind while maximizing its commanding presence. Designed to embrace Florida’s indoor-outdoor lifestyle, expansive sliding glass doors seamlessly connect the interior living spaces to two generous covered lanais, overlooking a resort-style heated pool and spa. Whether hosting sunset gatherings or enjoying a quiet morning overlooking the water, every space has been crafted to capture the beauty and serenity of waterfront living. Inside, sophisticated finishes and attention to detail abound. Wide-plank engineered hardwood flooring flows throughout the home, complemented by designer quartz countertops, custom cabinetry, and an open-concept floor plan filled with natural light. The chef-inspired kitchen serves as the centerpiece of the home, featuring an oversized island, premium finishes, and a spacious walk-in pantry. The convenience of dual laundry rooms further enhances the home's thoughtful design. For boating enthusiasts, the property features a concrete seawall and marina access, offering quick and convenient access to Sarasota Bay and the Gulf waters beyond—making it easy to enjoy world-class fishing, waterfront dining, and unforgettable days on the water. A boat slip is currently leased by the owner. Tucked away on a quiet street, yet just moments from Longboat Key’s pristine white-sand beaches, championship golf courses, marinas, boutique shopping, and renowned dining destinations, this residence delivers the perfect balance of privacy and accessibility. Offering the rare combination of new construction, waterfront location, elevated construction, luxury finishes, and Gulf boating access, 626 Buttonwood Drive represents an exceptional opportunity to own a premier Longboat Key waterfront retreat in one of Florida’s most coveted coastal communities. Luxury. Boating. Beach Life. Welcome Home.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Joshua Freed (941-577-5121)
1085 GULF OF MEXICO DR #205, LONGBOAT KEY, FL 34228
$939,000126 Days on yellowkey MLS ID: A4681713
REDUCED by $60,000 (6.0%) on 06/12/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1819 Built: 1981 Tax: $8,830 (2025)Community: Beachplace IiiSpa: YesCondo
Taxes:$8,830
Remarks: Spacious 3-Bedroom End-Unit Residence in Sought-After Beachplace Welcome to this beautifully maintained three-bedroom, two-bath end-unit condominium offering exceptional natural light, generous living spaces, and serene views in one of South Longboat Key’s most desirable beachfront communities. The open living and dining areas are thoughtfully designed for comfort and entertaining, featuring expansive sliders and windows that flood the space with sunlight and create seamless indoor-outdoor flow. A spacious living room opens to a south-facing screened lanai—perfect for enjoying morning light, golf course views, and gentle coastal breezes. The kitchen is bright and functional, offering ample cabinetry, full appliance package, and convenient in-unit laundry tucked neatly into a dedicated closet. Adjacent dining space provides flexibility for everyday living or hosting guests. The primary suite is generously sized and enjoys tranquil views, abundant natural light, and direct access to the lanai. Two additional bedrooms are versatility for guests, family, or a home office, all thoughtfully laid out to maximize privacy and comfort. Being an end unit, this residence benefits from additional windows and enhanced light throughout, creating an airy, welcoming atmosphere. Neutral finishes and tasteful furnishings allow for immediate enjoyment while offering an excellent canvas for personalization. Residents of Beachplace enjoy resort-style amenities, including a heated pool with lap lanes, spa, tennis courts, a fully equipped clubhouse with gathering spaces, on-site management, and private deeded beach access complete with lounge chairs and umbrellas. The community’s prime location places you moments from St. Armands Circle, Longboat Key Club, and downtown Sarasota’s dining, shopping, and cultural attractions. This well-cared-for residence presents an outstanding opportunity—whether as a primary home, vacation retreat, or income-producing investment in a premier Gulf-front community.
Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
Listing Agent: Michael Renick Pllc (941-400-8735)
2161 GULF OF MEXICO DR #3, LONGBOAT KEY, FL 34228
$4,395,000456 Days on yellowkey MLS ID: A4643048
0 Days Off yellowkey (back on 6/12/2026)
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3800 Built: 2001 Tax: $40,054 (2024)Community: En ProvenceSpa: YesCondo
Taxes:$40,054
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Experience beachfront luxury in this spacious 3,800-square-foot 3-bedroom, 3.5-bath + den/office residence in the prestigious En Provence community on Longboat Key. A private elevator opens to a grand foyer with marble floors and tray ceilings. Expansive glass sliders in the living room frame stunning Gulf views and lead to an oversized terrace, perfect for seamless indoor-outdoor living. The expansive terrace is ideal for entertaining, featuring a built-in gas grill and outdoor cooking space overlooking the beach and lush grounds. The kitchen is both stylish and functional, featuring a center island, white cabinetry, and pristine white stone countertops. High-end appliances, including a natural gas cooktop, enhance the space, while a bold blue tile backsplash adds a striking contrast. The adjacent eat-in area, with Gulf views and a built-in desk, enhances both charm and practicality. The primary suite offers terrace access and a spa-like bath with a soaking tub, dual vanities, a makeup area, and a glass-enclosed shower. Two guest suites each include en-suite baths and scenic views. A large office provides flexibility and could easily convert into a fourth bedroom. Additional features include an in-residence laundry room and 2 car garage. Set on nearly six acres of pristine beachfront, En Provence blends elegance and convenience with a clubhouse, resort-style pool and spa, fitness center, and 24-hour guard gate. For those seeking additional amenities, optional membership to the nearby Longboat Key Club provides access to world-class golf, tennis, dining, a marina, and a spa.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Bruce Myer (941-376-5311)
1241 GULF OF MEXICO DR #408, LONGBOAT KEY, FL 34228
$3,200,0005 Days on yellowkey MLS ID: A4695733
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: 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 Agent: Kathy Callahan (941-900-8088)
100 SANDS POINT RD #303, LONGBOAT KEY, FL 34228
$915,0001 Day on yellowkey MLS ID: A4696825
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1941 Built: 1966 Tax: $10,001 (2025)Community: Sands PointSpa: NoCondo
Taxes:$10,001
Remarks: Don’t miss this rare opportunity to call Sands Point home – an iconic beachfront community widely regarded as the crown jewel of Longboat Key. Nestled on the island’s coveted southernmost tip, this move-in-ready residence offers breathtaking sunsets and an unparalleled coastal lifestyle. Offered at an attractive value, this coastal escape presents a rare opportunity for the new owner to add their own finishing touches and create a truly personalized retreat. Welcome to your slice of paradise, where every day feels like a five-star coastal retreat, nestled inside the gates of the Longboat Key Club. Gracefully framed by towering palms, the curved waterfront drive creates a memorable sense of arrival, setting the tone for this one-of-a-kind mid-century modern residence where coastal elegance and timeless design converge. This spacious 1941 square feet, with its open floor plan feels more like a home than a condo. Step inside this bright third floor residence and discover a two bedroom, an office staged as a 3rd. bedroom and two baths, set in a split plan for privacy. Thoughtfully designed with warm custom cabinetry, elegant stone-inspired surfaces, and contemporary stainless appliances, this kitchen combines timeless craftsmanship with effortless coastal living. Floor to ceiling expanses of glass span the living area, offering a panoramic garden view and bathing the room in sunshine. The oversized layout provides endless possibilities for entertaining, gathering or simply enjoying the peaceful surroundings. Community amenities abound – enjoy the private beach with tiki’s, lounge chairs, pool, spa, library, community room w/ kitchen, marina access, bicycle storage, kayak launch, and additional owner’s storage space. Within walking distance to the well-renowned St Armands Circle for shopping and dining experiences. The pristine white sandy beach and gentle turquoise waters are calling your name. Schedule your private showing today and discover the lifestyle you deserve.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Diane Smith (941-313-4957)
828 BAYPORT WAY, LONGBOAT KEY, FL 34228
$900,00064 Days on yellowkey MLS ID: A4689635
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1456 Built: 1983 Tax: $5,880 (2025)Community: Bayport Bch & Ten Ph FCondo
Taxes:$5,880
Remarks: Bayport Beach & Tennis Club is a true Longboat Key Gulf-to-Bay community, set across 27 acres of beautifully maintained gardens with 1,200 feet of pristine private Gulf beach. Designed by Tim Siebert, one of the founding architects of the renowned Sarasota School of Architecture. Bayport is celebrated for its award-winning, timeless design. Residences like this rarely come to market. This first-floor, fully renovated unit showcases elevated designer finishes throughout. A picture-window screened patio opens to an expansive lanai, surrounded by lush, tropical landscaping; creating a seamless indoor-outdoor living experience. The modern kitchen features Caesarstone “concrete” quartz countertops, an induction cooktop, built-in oven, and custom cabinetry designed for both style and functionality. Each bathroom evokes a five-star resort experience, with thoughtfully curated custom details and designer lighting in both the baths and dining area. All windows and the patio slider have been upgraded to hurricane-impact glass for added peace of mind. The major components of the unit; the air conditioner and water heater have been upgraded. The home also features air purification paint for enhanced interior air quality. One under-building parking space is included, along with a private, locked storage closet which is perfect for bikes and beach gear. Beyond the beach, residents enjoy meticulously maintained nature trails, lushly landscaped grounds, and abundant wildlife. Just steps from the residence, the well-appointed clubhouse features a Junior Olympic-sized heated pool, four Har-Tru tennis courts, a fitness center, and more. Bayport is also known for its vibrant social and recreational lifestyle. Water enthusiasts will appreciate the secluded fishing pier extending into Sarasota Bay. An ideal setting to fish, take in the sunrise, watch manatees glide by, or egrets wading through the mangroves. Paddleboard and kayak launch and storage areas are conveniently located on-site. Residents enjoy easy access to local dining, a nearby supermarket, pharmacy, and charming boutique shops. Just moments away, Bayfront Park offers a popular pickleball program, dog park, and a variety of bayside activities. The Longboat Key Club is also nearby, offering private access to championship waterfront golf, boating, and an array of leisure amenities. Within minutes, you’ll find the renowned St. Armands Circle, known for its exceptional shopping and dining. From there, cross the iconic Ringling Bridge into downtown Sarasota, celebrated for its world-class theater, culture, and culinary scene. Offered by private appointment. Inquire to experience Bayport’s timeless coastal living firsthand.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Alexis Smith-Frady (352-225-1724)
100 SANDS POINT RD #225, LONGBOAT KEY, FL 34228
$899,00028 Days on yellowkey MLS ID: A4693834
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1492 Built: 1966 Tax: $3,929 (2025)Community: Sands PointCondo
Taxes:$3,929
Remarks: BACK ON THE MARKET with a New Price and Turn Key! Welcome to your slice of paradise, where coastal living reaches new heights of sophistication, and nestled inside the gates of the Longboat Key Club. This gorgeous 1492 sq. ft. water front residence underwent a total transformation in 2023, and the results are nothing short of spectacular. Step inside this bright second floor residence and discover a two bedroom and two baths, with a view that feels serene, luxurious, and unmistakably coastal. This condo comes with a view of the private marina tucked away in a quiet cove, where you can enjoy watching the dolphins at play. Towering palm trees frame the scene beautifully, with the curved waterfront drive adds a resort-style elegance to this one-of-a-kind property. This kitchen has a bright, modern, upscale feel with a clean coastal-inspired design. White shake-style cabinetry with sleek brushed nickel handles, extending all the way to the ceiling for extra storage. Exotic granite counters, matched with a sleek white Carrara marble back splash. Stainless steel appliances, and a deep undermount sink with a tall industrial-style spring faucet. The expansive great room steals the show, with a dramatic wall of windows, open concept and LVP flooring thru out. Both bathrooms feature quartz counter tops, tiled floors and walk in showers. HVAC 2020. Community amenities abound – enjoy the private beach with tiki’s, lounge chairs, pool, spa, library, community room with kitchen, marina access, bicycle storage, kayak launch, and additional owner’s storage space. With in walking distance to well renowned St Armands Circle for shopping and dining experiences. The pristine white sandy beach and gentle turquoise waters are calling your name. Schedule your private showing today and discover the lifestyle you deserve.
350 GULF OF MEXICO DR #234, LONGBOAT KEY, FL 34228
$749,000148 Days on yellowkey MLS ID: A4678529
1 Days Off yellowkey (back on 5/14/2026)
REDUCED by $150,000 (16.7%) on 04/24/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2513 Built: 1992 Tax: $10,107 (2025)Community: Tangerine Bay ClubSpa: YesCondo
Taxes:$10,107
Remarks: Virtually Staged. Set amid the lush, manicured grounds of Tangerine Bay, this exceptional two-story penthouse residence offers a rare blend of architectural volume, natural light, and water views. Mature tropical landscaping, tranquil lagoons, and resort-style amenities create a serene, park-like environment that feels both private and welcoming. Two terraces highlight scenic views and offer the option of installing a gas grill. Inside, soaring two-story ceilings define the main living area, creating an airy, light-filled atmosphere enhanced by expansive windows that frame picturesque views of the lagoon, resort-style pool w/ waterfall features, tropical plantings and the waters of Sarasota Bay and distant city skyline. The open living and dining spaces are ideal for both relaxed everyday living and entertaining, anchored by a fireplace and generous wall space for art. From the entry patio, unexpected Bay and city views provide a striking first impression and a unique urban-meets-coastal backdrop. The residence features three full bedrooms and three and a half baths. The upper-level retreat with its full bath has a terrace with elevated views across the natural preserve toward the city. This home presents a true blank canvas, thoughtfully priced to allow the new owner to reimagine and transform it into their own vision of refined coastal living. A deeded, private two-car garage adds exceptional convenience and value—an uncommon and highly desirable feature. Located on the coveted south end of Longboat Key, Tangerine Bay Club is a gated, pet-friendly community close to Lido Beach, dining and boutique shopping on St. Armands Circle, and the cultural, dining, and arts scene of downtown Sarasota. Optional Bay Isles Beach Club membership is available, providing exclusive access to a private, gated four-acre Gulf of Mexico beach facility, reserved for a select group of members—ideal for beach gatherings, sunset celebrations, and effortless days by the sea. An outstanding opportunity to embrace the Florida lifestyle in one of Longboat Key’s most desirable bayfront communities.
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
1915 HARBOUR LINKS CIR #6, LONGBOAT KEY, FL 34228
$1,950,00072 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: Private Beach Access + Gated Bay Isles Living on Longboat Key! Welcome to Emerald Pointe South, where maintenance-free coastal living meets one of the island’s most desirable gated communities. This beautifully maintained villa offers the relaxed Florida lifestyle buyers are searching for — ideal as a full-time residence, seasonal retreat, or investment opportunity. Inside, a bright and open floor plan features spacious living and dining areas filled with natural light from expansive sliding glass doors. The private screened lanai overlooks lush tropical landscaping, creating the perfect setting for morning coffee or evening relaxation. The kitchen offers solid surface countertops, abundant cabinetry, a breakfast nook, and newer appliances including a microwave, dishwasher, and stove. The spacious primary suite features dual walk-in closets and a large en-suite bath with dual vanities, soaking tub, and separate shower. Upstairs, two additional bedrooms each include private en-suite baths, providing comfort and privacy for guests and family. Residents enjoy the security of gated Bay Isles along with coveted private beach access to the Gulf of Mexico. Located just minutes from St. Armands Circle and downtown Sarasota, this home offers easy access to waterfront dining, shopping, golf, marinas, and world-renowned beaches. Low-maintenance island living, private beach access, and an unbeatable Longboat Key location — this is the coastal lifestyle buyers dream about.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Cathy Palmer (678-524-1104)
3606 FAIR OAKS PL, LONGBOAT KEY, FL 34228
$4,999,00018 Days on yellowkey MLS ID: A4694394
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3842 Built: 2000Monthly Fee: $833 Tax: $29,486 (2025)Community: Queens HarborSpa: YesSingle Family
Taxes:$29,486
Remarks: Nestled behind the gates of the highly celebrated Bay Isles community, this exceptional five-bedroom waterfront residence at 3606 Fair Oaks Lane offers the perfect blend of luxury, comfort, and peace of mind with an impressive list of recent upgrades and improvements. Designed for effortless coastal living, this beautifully updated home showcases refined interiors, expansive outdoor living spaces, and direct boating access, all within one of Longboat Key’s most sought-after neighborhoods. From the moment you arrive, the home’s meticulous maintenance and thoughtful renovations are immediately apparent. A roof just two years old, hurricane shutters on all windows and doors, and multiple updated mechanical systems provide exceptional value and confidence for years to come. Inside, the residence has been extensively renovated in 2026 with stunning new engineered wood flooring flowing throughout the home, creating a warm and welcoming coastal aesthetic. The spacious floor plan offers five generously sized bedrooms, ideal for accommodating family and guests while maintaining privacy and flexibility for today’s lifestyle needs. The heart of the home is the beautifully refreshed kitchen, complete with brand-new KitchenAid appliances installed in 2026, blending modern functionality with timeless design. Adjacent living and dining areas are filled with natural light and seamlessly connect to the outdoor entertaining spaces, creating an inviting atmosphere perfect for both everyday living and hosting gatherings. Every bathroom in the home was completely renovated in 2026 with stylish finishes and contemporary details that elevate the home’s overall elegance. Extensive system upgrades include three HVAC systems replaced in 2022, 2023, and 2026, along with a new hot water heater installed in 2026, ensuring maximum efficiency and comfort throughout the property. Outdoor living is equally impressive and designed to embrace the Florida waterfront lifestyle. The pool area underwent a significant transformation in 2025 with new pool decking, a resurfaced pool finish, updated waterline tile, and a new gas pool heater, creating a true private resort setting. In 2026, the addition of a fully equipped outdoor kitchen elevated the entertaining experience even further, offering the perfect backdrop for waterfront dining and sunset gatherings. Boating enthusiasts will appreciate the new 10,000-pound boat lift installed in 2025 along with a beautifully updated dock and deck, providing quick and convenient access to Sarasota Bay and the Gulf waters beyond. Combining luxury updates, exceptional outdoor amenities, and a premier location within the coveted Bay Isles community, with private beach club access, this extraordinary Longboat Key residence presents a rare opportunity to enjoy refined waterfront living with every major improvement already completed.
Listing is courtesy of: SARASOTA TRUST REALTY COMPANY (941-366-1619)
Listing Agent: Renee Preininger (941-400-4235)
3271 BAYOU RD, LONGBOAT KEY, FL 34228
$1,995,0008 Days on yellowkey MLS ID: TB8515918
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: 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)
2367 HARBOUR OAKS DR, LONGBOAT KEY, FL 34228
$949,500195 Days on yellowkey MLS ID: A4670055
REDUCED by $35,500 (3.6%) on 06/04/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2219 Built: 1986Monthly Fee: $1,617 Tax: $11,977 (2024)Community: Harbour Oaks 2Villa
Taxes:$11,977
Remarks: NEW PRICE: Lives like a single family home! This 3 bedroom, 2 1/2 bath villa with over 2,200 sq.ft and an attached 2-car garage offers all the privacy and convenience of a private home and all the convenience of a maintenance free community. Located on #2 hole of the White Egret course on the Harbourside Golf Course in the Longboat Key Country Club. This home is in a secure gated community with only 42 villas in Harbour Circle with a community pool and spa and membership access to the deeded private beach club. This home boasts vaulted ceilings, multiple hurricane skylights, hurricane windows, sliders and front door, private atrium and new roof with trusses in 2025, coming completely furnished. Enjoy your morning coffee and dozens of magnificent sunsets on your large two level lanai. Enjoy a walk to Publix, CVS and several Banks close to your community. Only a short drive to Saint Armand's Circle and downtown Sarasota where you will find numerous options for shopping, dinning, theatres, ballet, opera and galleries.
Listing Agent: Sandra Endres (941-735-2527)
1281 GULF OF MEXICO DR #708, LONGBOAT KEY, FL 34228
$3,275,000154 Days on yellowkey MLS ID: A4677632
1 Days Off yellowkey (back on 6/11/2026)
Bed: 3 Bath: 4.5 Gar: 1 Liv Area Sq Ft: 3273 Built: 1999 Tax: $26,304 (2024)Community: Water Club At Longboat KeySpa: NoCondo
Taxes:$26,304
Remarks: Under contract-accepting backup offers. Welcome to an extraordinary corner residence at The Water Club where timeless elegance meets effortless coastal living on Longboat Key. Offering 3,275 square feet of beautifully designed interior space, this 3-bedroom, 4.5-bath condominium captures sweeping unobstructed expansive views of the Gulf of Mexico, glowing sunsets, Sarasota Bay, and the city skyline from nearly every room. Floor-to-ceiling windows and expansive sightlines fill the home with natural light, creating a serene and sophisticated atmosphere throughout. Designed with refined craftsmanship, the residence showcases custom woodworking, hardwood floors, and soaring 10-foot ceilings that enhance the sense of scale and luxury. The thoughtfully designed layout provides generous living and entertaining spaces while maintaining privacy for guests. The home is in true move-in condition and has been thoughtfully updated with all-new appliances in 2025, blending modern convenience with classic finishes. Enjoy the exclusivity of private elevator access directly to the residence, along with full concierge services that elevate everyday living. The building offers an impressive collection of resort-style amenities, including a Gulf-front swimming pool overlooking pristine white sand beaches, a fully equipped fitness studio, an elegant library, a grand ballroom for entertaining, and a game room for relaxation and recreation, a premier parking space, and as well as climate controlled storage units. This exceptional property delivers the best of beachfront living with luxury, privacy, and breathtaking views all within one of Longboat Key’s most desirable addresses. A rare opportunity to own a refined coastal retreat where every detail has been carefully considered and every day feels like a getaway.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Kim Ogilvie (941-951-6660)
617 ROUNTREE DR, LONGBOAT KEY, FL 34228
$2,350,00032 Days on yellowkey MLS ID: A4692822
REDUCED by $145,000 (5.8%) on 06/10/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1972 Built: 1973Monthly Fee: $250 Tax: $7,892 (2025)Community: Longboat Key EstatesSpa: NoSingle Family
Taxes:$7,892
Remarks: Premier waterfront opportunity in Longboat Key Estates, offering direct canal frontage in one of the island’s most desirable residential enclaves. Positioned along a quiet interior street, this property offers the opportunity to own or build a custom coastal residence in an area undergoing continued redevelopment and investment potential. Surrounding properties reflect the neighborhood's transformation, with new-construction homes setting a high standard for modern, exclusive waterfront living. The canal setting provides protected waters for boating with access to Sarasota Bay, while deeded, private beach access offers the rare combination of boating and beachside lifestyle. This property offers views of Sarasota Bay and the Intracoastal Waterway directly from your Lanai and dock, featuring a 100 feet of seawall frontage (2022) and a 16,000-pound boat lift (2022). Generous lot dimensions and a tranquil waterfront setting create an exceptional opportunity for boating enthusiasts and the ideal canvas for a thoughtfully designed custom residence. As a resident of Longboat Key Estates, a deed-restricted single-family waterfront community, you have deeded access to the Gulf and a private resident-only Tiki within a five-minute walk. Enjoy close proximity to Bayfront Park offering pickleball and tennis, kayaking, along within close distance to fine dining, St. Armands Circle, downtown Sarasota, Sarasota International Airport, and Florida’s Gulf Coast, all at your doorstep!
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Judi Taulbee (941-544-6227)
2055 GULF OF MEXICO DR #G2-213, LONGBOAT KEY, FL 34228
$610,00093 Days on yellowkey MLS ID: TB8485915
REDUCED by $12,000 (1.9%) on 06/10/2026
Bed: 1 Bath: 1.5 Liv Area Sq Ft: 1094 Built: 1974 Tax: $5,426 (2025)Community: Seaplace ICondo
Taxes:$5,426
Remarks: NO expense spared and everything replaced! Gulf and greenbelt views await from your top floor Seaplace condo! Completely remodeled. This gorgeous gulf-facing oversized one bedroom, 1.5 bath end unit with vaulted ceilings features 1,094 square feet of living space and spacious lanai adding an additional 112 square feet with custom 95% UV blocking solar shades. The convenient second floor location provides quick access to the beach, which is only 178 yards from your front door. Enjoy beautiful sunsets with a glass of wine, while taking in the peaceful greenbelt and gulf views from your screened-in lanai complete with high quality Polywood outdoor furniture and Modern Forms WIFI enabled ceiling fan. The spectacular remodel includes new hurricane impact sliding glass doors and bedroom window, new front door and casement window, HVAC unit replaced in 2022, LG Thin Q stacked washer and dryer, ceiling fans in bedroom and living room, Nest programable WIFI thermostat, all new plumbing and plumbing fixtures, all electrical replaced including electrical outlets, new switches and LED recessed lighting throughout. The new porcelain plank "driftwood look" floor tiles throughout the condo and into the Lanai compliment the coastal, beachy vibe of the Cypress Pecky Wood and shiplap accent walls. The gourmet kitchen was completely redesigned with an open concept and includes Kraftmaid soft close wood cabinetry and drawers, GE Cafe appliances suite with convection oven, warming drawer and conduction cooktop, floating shelves and Cambria Quartz counters. The popcorn ceilings were removed and re-plastered with smooth texture throughout. Both bathrooms have new vanities with Cararra marble counters, tile accent walls, including Calcatta Gold Marble Penny tile in half bath and redesigned primary bath. The bedroom features custom open concept built-in closets with soft close drawers and doors. Custom woven wood shades in living room and black out shades in bedroom. Other features include all new solid core interior doors, expansive storage closet under the stairs, owner's locker in common area, dedicated bike storage room adjacent to condo and one assigned parking space. Situated on 42 acres of manicured resort grounds and amenities, Seaplace is one of Longboat Key's most desirable communities. Enjoy two Olympic sized swimming pools, spas, one mile of trails along the shore and throughout the complex, 3 tennis courts, remodeled club house, fitness center, barbecue islands and parklike grounds. Whether you are looking for a vacation get-away, second home, investment property or permanent residence, this is the one! Seaplace is a gated community with a 24-hour guarded gate. Situated only one complex North of the famed St. Regis Luxury Hotel and Residences. This lovely condo is sold completed outfitted, fully-furnished with high quality furnishings from Pottery Barn, Restoration Hardware and comes complete with two fairly new Schwinn bicycles. Must see to appreciate. Owner has a real estate license in CA.
Listing is courtesy of: CONTINENTAL REAL ESTATE GROUP (877-996-5728)
Listing Agent: Derek Eisenberg
510 HARBOR GATE WAY, LONGBOAT KEY, FL 34228
$4,395,000214 Days on yellowkey MLS ID: A4671696
Bed: 4 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 5080 Built: 1996Monthly Fee: $208 Tax: $42,201 (2024)Community: Bay IslesSpa: YesSingle Family
Taxes:$42,201
Remarks: A Waterfront Work of Art. Experience a one-of-a-kind waterfront residence on Longboat Key — now offered at an exceptional new value. Designed around three interconnected circular "pods," the residence flows like a choreographed dance. There are no awkward hallways, no wasted corners, no spaces that feel like afterthoughts. Curved walls carry throughout every room — even into the garage — creating a cohesive design statement that's genuinely rare in residential construction at any price point. This architectural masterpiece is a sculptural composition of flowing living spaces connected by custom corridors, delivering remarkable privacy, abundant natural light, and seamless indoor–outdoor living. The dramatic Great Room pod showcases soaring wood-paneled ceilings and expansive walls of glass that frame tranquil water views. The circular primary suite is a private retreat featuring a spa-inspired bath with dual showers, a lounge area, private office, and direct access to the pool and spa terrace. At the heart of the home, the striking circular kitchen is both artful and functional, centered around a curved island beneath a two-story ceiling and skylight, with a thoughtfully designed radial appliance layout. Two en-suite guest bedrooms open to private patios, while the fully self-contained Secondary Primary Suite above the impressive 32' x 23' three-car garage offers independent HVAC, a luxury bath with steam shower and sauna, and flexible living space ideal for extended guests or multigenerational living. Outdoors, the property embraces the waterfront lifestyle with protected deep sailboat water, a private dock with a 12,000-pound lift, and a resort-style pool and spa designed for entertaining and relaxation. Located behind the 24-hour guarded gates of Bay Isles, residents also enjoy exclusive access to the Bay Isles Beach Club on the Gulf of Mexico.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: John August (941-320-9795)
455 LONGBOAT CLUB RD #707, LONGBOAT KEY, FL 34228
$1,850,000134 Days on yellowkey MLS ID: A4680080
REDUCED by $149,950 (7.5%) on 06/10/2026
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2410 Built: 1990 Tax: $9,861 (2025)Community: PierreCondo
Taxes:$9,861
Remarks: Welcome to The Pierre, a distinguished Gulf-front address behind the private gates of the Longboat Key Club, offering a rare blend of refined coastal living, privacy, and world-class resort lifestyle appeal for discerning buyers from around the globe. Located on the seventh floor, Residence 707 showcases spectacular sunset skies over the Gulf of Mexico, complemented by peaceful bay and city vistas, creating a dynamic panorama from sunrise through evening. Expansive windows fill the interiors with natural light while framing the natural beauty of Longboat Key’s shoreline and Sarasota Bay. Thoughtfully designed for both relaxed living and gracious entertaining, the residence offers generous living spaces and a seamless indoor-outdoor connection. The floor plan includes two ensuite bedrooms and a flexible third bedroom with sliding retractable wall, three full baths, and spacious living and dining areas—each with direct access to the residence’s gracious balconies. Residents of The Pierre enjoy an exceptional array of amenities, including direct private beach access, a beachfront pool, spa, fitness center,, tennis courts, a newly renovated lobby, club gathering room, meeting room and 24-hour guard security. Private guest suites are also available for visiting family and guests on a nominal rental basis. Ownership is further enhanced by secure garage parking, a private secured storage area, and onsite professional management, providing ease and confidence for both year-round and seasonal owners. Beyond the residence, membership opportunities at the renowned Longboat Key Club provide access to a celebrated resort lifestyle, featuring championship golf courses, world-class tennis, spa and wellness facilities, multiple dining venues, beach services, and an active social calendar (membership subject to application and availability). Perfectly situated near St. Armands Circle and downtown Sarasota’s cultural attractions, Residence 707 represents a rare opportunity to own within one of Longboat Key’s most prestigious waterfront communities—where international sophistication, panoramic views, and a coveted club lifestyle converge in one extraordinary coastal setting.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Judy Wright, Pa (941-232-8041)
210 SANDS POINT RD #2402, LONGBOAT KEY, FL 34228
$999,9003 Days on yellowkey MLS ID: A4696591
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 642 Built: 1982 Tax: $10,500 (2026)Community: Inn On The Beach Ph ISpa: YesCondo
Taxes:$10,500
Tax Year: 2026
Remarks: The Resort at Longboat Key Club – Gulf Front Condo-Hotel Investment Opportunity Best Priced Beachview Condo. Rxperience the best of coastal luxury and income-producing ownership at The Resort at Longboat Key Club. This beautifully renovated, turnkey one-bedroom Club Suite offers breathtaking direct views of the Gulf of Mexico, overlooking both the pristine beach and resort-style pool. Designed for effortless ownership, this exceptional residence is currently enrolled in the resort's rental program and professionally managed in partnership with Opal Hospitality, allowing owners to enjoy personal use while generating rental income.Whether you're seeking a vacation retreat, an investment property, or both, this Gulf-front suite delivers an unparalleled resort lifestyle. Ideally located just minutes from St. Armands Circle, you'll enjoy easy access to boutique shopping, exceptional restaurants, arts, culture, and all that Sarasota's Gulf Coast has. Recent renovations provide a fresh, modern coastal aesthetic, making this residence truly move-in ready. Don't miss this rare opportunity to own a piece of paradise in one of Florida's most sought-after luxury resort destinations. Enjoy the benefits of resort ownership, professional management, and spectacular Gulf views—all in one extraordinary property. Guests and owners alike enjoy world-class amenities, including: 45 holes of championship golf Award-winning tennis facilities Full-service marina Luxury spa and wellness services Fine dining and resort lounges Beachfront pool and private beach access Concierge and maid service
Listing is courtesy of: MY FLORIDA BROKER (941-932-2707)
Listing Agent: Patti Bosco (941-932-2707)
1932 HARBOURSIDE DR #244, LONGBOAT KEY, FL 34228
$1,175,00066 Days on yellowkey MLS ID: A4689076
REDUCED by $25,000 (2.1%) on 06/09/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1192 Built: 1982 Tax: $9,436 (2024)Community: Fairway Bay 1Condo
Taxes:$9,436
Remarks: Welcome to this breathtaking, fully remodeled, turnkey furnished contemporary residence in Fairway Bay—nestled on picturesque Longboat Key. From the moment you enter, you're greeted by a thoughtfully redesigned open floor plan, elevated ceilings, solid core doors, and impeccable high-end finishes. IT IS TRULY ONE OF A KIND! This condominium is truly one-of-a-kind! Exceptional Kitchen features include: Bertazzoni induction range, refrigerator, and dishwasher, built-in Miele plumbed espresso machine, sleek, low-profile custom cabinetry with quartz countertops, glass tile backsplash and ambient lighting and an expansive quartz island perfect for formal dining or casual entertaining. The living room flows effortlessly from the kitchen, opening onto a covered, tiled lanai—blurring the line between indoor and outdoor living. Floor-to-ceiling impact windows frame panoramic views of Sarasota Bay, the Ringling Bridge, and the city skyline, offering million-dollar scenery from the comfort of your home. Enter the generously sized and luxurious Primary Suite with custom built-ins and ample closet space. The ensuite bath is a spa-inspired bath with dual vanities, Hansgrohe Axor faucets, Toto washlet, walk-in shower with multiple heads and elegant finishes. The guest suite features custom cabinetry and an ensuite bathroom with a Victoria & Albert volcanic limestone bathtub. Other recent upgrades include Hurricane-impact windows and doors, tankless water heater, additional upper cabinetry in kitchen and utility room, ceiling fans and more. For your convenience & comfort there is easy elevator access, coveted garage parking space and private onsite storage. Fairway Bay residents enjoy the resort-Style amenities including Deeded beach access & exclusive beach club, 24-hour gated security, pool, spa, tennis courts, and fitness center plus all the perks of Bay Isles living. Whether you're soaking in the sun, enjoying vibrant Sarasota culture and nightlife, or relaxing in your private retreat, this home is a perfect sanctuary.
Listing is courtesy of: BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE (941-556-9100)
Listing Agent: Jan Jordan (941-737-4169)
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