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Booker High - A4699685 - 525 SLOOP LN, LONGBOAT KEY, FL 34228 4 Days on yellowkey
$1,999,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Discover an exceptional chance to complete a vision of waterfront luxury in the highly sought-after community of Country Club Shores on Longboat Key. This canal-front home offers the rare opportunity to pick up where the current owner left off—finishing a sophisticated coastal residence with the majority of major structural work already completed. For discerning buyers seeking to capture immediate equity and create a bespoke waterfront retreat, this property represents outstanding value in prime Longboat Key real estate. Set on a spacious 110’ x 110’ canal-front lot, the home features a fully reconstructed seawall and a private dock equipped with a 13,000-pound Platinum Series boat lift, providing effortless access to Sarasota Bay and the sparkling Gulf of Mexico. The residence is framed for approximately 3,089 square feet under air, offering 5 bedrooms and 3 bathrooms in an elegant coastal ranch-style layout designed for seamless indoor-outdoor living. Substantial improvements have already been executed to the highest standards: a brand-new roof, complete framing, exterior walls, plumbing and electrical rough-ins, natural gas lines, insulation, HVAC ductwork, and impact-resistant windows and doors. Premium materials and finishes—including custom Italian cabinetry, Miele appliances, designer fixtures, and additional high-end components—convey with the property. Engineer-prepared plans provide a clear roadmap for completion, empowering the next owner to personalize the final touches while benefiting from the extensive work already invested. Located in one of the best positions within the desirable Country Club Shores community, this fixer-upper presents the perfect canvas to realize the seller’s vision of an amazing luxury waterfront home. Imagine waking to serene water views, launching your boat from your private dock, and enjoying the effortless Florida lifestyle that defines Longboat Key. Just moments away, enjoy world-class amenities and recreation: championship golf at the prestigious Longboat Key Club, pristine Gulf beaches for sun-soaked days, and the vibrant dining and shopping scene at St. Armands Circle. Explore Sarasota’s renowned fine and performing arts venues, upscale boutiques, and waterfront restaurants—all while residing in this sought-after enclave. Whether you crave boating adventures, cultural experiences, or relaxed coastal living, this location delivers unparalleled convenience and luxury. Don’t miss this unique opportunity to complete a standout waterfront property and unlock its full potential in one of Florida’s most desirable communities.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY
Booker High - A4699377 - 571 RANGER LN, LONGBOAT KEY, FL 34228 7 Days on yellowkey
$3,195,000 | Single Family Home | 4 beds | 3.0 baths | 1 gar
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
Pine View School - A4699348 - 657 HALYARD LN, LONGBOAT KEY, FL 34228 8 Days on yellowkey
$4,300,000 | Single Family Home | 4 beds | 5.0 baths | 2 gar
Experience timeless coastal luxury in this exceptional custom estate, perfectly positioned in the prestigious Country Club Shores on the sought-after south end of Longboat Key. Constructed by renowned John Cannon Homes, this classical waterfront residence showcases the exceptional craftsmanship, architectural detail, and quality for which the builder is celebrated. Soaring ceilings, elegant millwork, walls of glass, and exquisite finishes create a light-filled home that perfectly frames the surrounding water views while offering nearly 4,400 square feet of beautifully designed living space. Ideally situated just one home from Sarasota Bay, this rare waterfront property captures sweeping bay views while providing the privacy, protection, and peace of mind that come with its prime location and newer construction. Beautifully updated in 2025 by Brista Homes, the residence features four bedrooms, five full baths, a spacious game room, and a generous loft office with breathtaking bay views—an inspiring space for working remotely or simply relaxing while enjoying spectacular sunsets. Multiple indoor and outdoor living areas are thoughtfully designed for effortless entertaining and everyday coastal living. Light-filled interiors blend refined custom details with relaxed elegance. The gourmet kitchen, appointed with newer appliances (2022), opens seamlessly to the living and dining areas, creating an inviting setting for intimate family gatherings or grand-scale entertaining. The luxurious primary suite is a private sanctuary featuring direct pool access, an elegant tray ceiling, and dual custom walk-in closets. Upstairs, guest suites offer en-suite baths and generous closets, providing exceptional privacy and comfort for family and visitors alike. Extensive recent improvements include a new roof (2025), updated windows, new balusters, and thoughtfully selected designer finishes throughout, creating a residence that perfectly balances timeless elegance with today's modern conveniences. Outdoor living is equally extraordinary. Expansive terraces, a sparkling pool, and tranquil waterfront views create the perfect backdrop for the coveted Florida lifestyle. For boating enthusiasts, the deep-water canal frontage features a composite dock, a 12,000-pound boat lift, and a newer seawall, providing immediate access to Sarasota Bay and just minutes to the Gulf of Mexico. Country Club Shores is one of Longboat Key's most prestigious waterfront communities, encompassing 19 picturesque streets with distinctive nautical and golf-inspired names. The homeowners association maintains the beautifully landscaped common areas and hosts a variety of neighborhood social events, fostering an exceptional sense of community. Residents enjoy convenient beach access and an unbeatable location just minutes from the world-class shopping and dining of St. Armands Circle, as well as the acclaimed restaurants, theaters, galleries, and cultural attractions of downtown Sarasota. Offering panoramic water views, exceptional boating, beach access,and an outstanding south Longboat Key location, this is a rare opportunity to own an extraordinary waterfront residence where timeless architecture, modern luxury, and the very best of Florida coastal living come together.
Listing is courtesy of: COLDWELL BANKER REALTY
Pine View School - A4699335 - 2301 GULF OF MEXICO DR #44N, LONGBOAT KEY, FL 34228 8 Days on yellowkey
$625,000 | Condo | 2 beds | 2.0 baths | 1 car
Simply magnificent! This beautifully renovated residence offers the perfect blend of sophisticated design, comfort, and effortless coastal living. Thoughtfully updated with designer finishes throughout, this move-in-ready home features an open, light-filled floor plan highlighted by floor-to-ceiling windows and a spectacular 38-foot covered terrace overlooking lush tropical gardens. Accessible from the living room and both bedrooms, the expansive terrace is the perfect place to enjoy your morning coffee, entertain guests, or relax with refreshing Gulf breezes. The updated kitchen flows seamlessly into the dining and living areas, creating an inviting space for everyday living and entertaining. Beautiful wood flooring, custom architectural details, stainless steel appliances, and abundant natural light add warmth and elegance throughout the home. The spacious primary suite serves as a private retreat with terrace access and a beautifully renovated ensuite bath featuring light wood cabinetry and granite countertops. The generous guest bedroom also opens to the terrace and includes a built-in Murphy bed, offering exceptional flexibility for visiting family and friends or a home office. Life at The Islander Club is truly resort-inspired. Residents enjoy over 400 feet of private Gulf-front beach, a heated beachfront swimming pool, a newly renovated state-of-the-art fitness center, two new sauna rooms, a Har-Tru® tennis court, two pickleball courts, a beautifully updated social room, library, secure key-fob entry, on-site management, and exceptional lock-and-leave convenience. Adding even greater value, The Islander Club has recently completed an extensive program of capital improvements, including exterior restoration and stucco repairs, balcony waterproofing, new roofs on both residential towers, clubhouse, and carports, modernized pool facilities with new tile, resurfacing, and equipment, refreshed landscaping and lighting, hurricane-rated windows and doors, and a completely renovated fitness center. These significant investments provide both peace of mind and long-term value for future owners. Whether you are searching for a full-time waterfront residence, a seasonal escape, or an exceptional investment opportunity, this beautifully updated condominium offers the very best of Longboat Key's coveted beachfront lifestyle.
Bayshore High - A4699520 - 580 LINLEY ST, LONGBOAT KEY, FL 34228 8 Days on yellowkey
$999,000 | Single Family Home | 2 beds | 2.0 baths | 1 gar
Discover this stunning, completely renovated interiors two-bedroom, two-bath home nestled in the Historic Longbeach Village on the quiet north end of Longboat key. More than just a home, this is a true coastal lifestyle. Perfectly positioned just a five minute walk to the largest public beach on Longboat Key. you'll enjoy effortless access to sugar-white sand, breathtaking Gulf sunsets, and endless days of beachside relaxation. Thoughtfully redesigned with upscale designer finishes throughout, this charming residence blends timeless Old Florida character with modern luxury. Terrazzo floors flow throughout the home, while the fully remodeled kitchen features premium cabinetry, quality appliances, and a functional layout that's perfect for everyday living or entertaining. Both bathrooms have been beautifully renovated with high-end finishes, including a luxurious primary bath with a large soaking tub, custom walk-in shower, and designer tile. No detail was overlooked and no expense was spared in this exceptional renovation. Leave the car behind and stroll to local favorites including Whitney's The Shore, and Mar Vista, all just minutes away. Ride your bike through the peaceful village, walk to the beach, or simply relax and enjoy the tranquil surroundings that make this neighborhood so special. Just over the bridge, Coquina Beach offers pristine shoreline, stunning Gulf Views, convenient concessions, and a popular farmers market, while Anna Maria Island provides an abundance of boutique shopping, waterfront dining, and laid-back island atmosphere. St. Armands Circle is only a short drive away with upscale shopping, restaurants, theater, marinas, and boat launches. Opportunities to own a fully renovated home in Historic Longbeach Village with this combination of location, walkability, and coastal charm are rare. Don't miss your chance to experience the serenity, beauty, and unmatched lifestyle of Longboat Key.
Listing is courtesy of: RE/MAX ALLIANCE GROUP
Booker High - A4697745 - 617 WESTON POINTE CT, LONGBOAT KEY, FL 34228 10 Days on yellowkey
$3,100,000 | Single Family Home | 4 beds | 5.0 baths | 2 gar
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
Bayshore High - A4698065 - 578 SPANISH DR S, LONGBOAT KEY, FL 34228 11 Days on yellowkey
$499,000 | Villa | 2 beds | 2.0 baths | 1 car
Welcome to 578 Spanish Drive S, a completely renovated 2 bedroom, 2 bathroom villa in Spanish Main Yacht Club on Longboat Key. Renovated completely with thoughtful attention to detail, this move-in ready residence showcases high-quality modern finishes while providing access & amenities to one of Longboat Key's established waterfront communities with a deepwater marina and deeded beach access. The redesigned interior features an open kitchen centered around a quartz waterfall edge island, soft close cabinetry, with all new stainless-steel appliances, including a wine refrigerator and a refrigerator with a built-in craft ice maker. Luxury vinyl plank flooring extends throughout the home, complemented by a smart thermostat for everyday convenience. Every room reflects the comprehensive renovation, and the home is further enhanced by a 2012 tile roof, new PGT hurricane impact windows, and sliding glass doors that open to a private paver patio overlooking a wooded landscaped setting. Spanish Main Yacht Club offers private deeded beach access to the Gulf of Mexico, a heated community pool, clubhouse, shuffleboard courts, and a pet-friendly environment. The community’s deepwater marina offers approximately 40 boat slips available for lease, accommodating vessels up to 40 feet with water and electric service, while providing direct boating access from Sarasota Bay to the Gulf of Mexico. Residents also enjoy opportunities for fishing, kayaking, paddleboarding, and other waterfront recreation. Located near Publix, St. Armands Circle, downtown Sarasota, shopping, dining, cultural attractions, botanical gardens, Anna Maria Island, and Sarasota-Bradenton International Airport, this extensively renovated villa offers an exceptional combination of updated interior finishes, outdoor living, boating amenities, and convenient access to the best of Longboat Key and the surrounding Sarasota area. Please see attached document for the full list of renovations & upgrades and full walkthrough video and virtual walkthrough. Not required to be 55 to purchase.
Listing is courtesy of: LOYD ROBBINS & CO. LLC
Sarasota High - A4698596 - 2301 GULF OF MEXICO DR #45N, LONGBOAT KEY, FL 34228 11 Days on yellowkey
$625,000 | Condo | 2 beds | 2.0 baths
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 is courtesy of: PREFERRED SHORE LLC
Riverview High - A4698785 - 1211 GULF OF MEXICO DR #302, LONGBOAT KEY, FL 34228 15 Days on yellowkey
$13,500 | Condo | 2 beds | 3.0 baths
**Prime Location – Luxurious Waterfront Living at Promenade, Longboat Key** This absolutely gorgeous condo is located in the prestigious Promenade on Longboat Key, offering breathtaking water views from every room. The residence features 2 bedrooms plus a den and 2 bathrooms. The spacious master suite includes a king-size bed and an elegant en-suite bathroom with a separate bathtub, walk-in shower, and bidet for added convenience. The second bedroom is ideal for guests, offering two twin beds that can be converted into a king-size bed. The versatile den can be used as a home office or additional sleeping space, featuring a sofa that converts into a bed for unexpected guests. The well-appointed contemporary kitchen makes entertaining effortless, while electric motorized shades in the family room, master bedroom, and kitchen provide added comfort and convenience. Step outside to your private terrace and enjoy stunning sunrises and sunsets over the water—true Florida coastal living at its finest. Residents of The Promenade enjoy world-class amenities, including a private beach, 24-hour manned gated security, full concierge services, on-site management, two social rooms, fitness center, men’s and women’s health clubs, four Har-Tru tennis courts, a Gulf-side heated resort-style swimming pool and spa, and a beautifully landscaped gazebo area surrounded by lush tropical grounds. The unit includes one assigned parking space, with additional guest parking available. This is the perfect destination to experience luxury Florida vacation living at its finest. Available December 1, 2026. Tenant must pay a $75.00 Broker Fee.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE
Booker High - A4698791 - 2850 GULF OF MEXICO DR #4, LONGBOAT KEY, FL 34228 15 Days on yellowkey
$325,000 | Condo | 1 beds | 1.0 baths
Coastal Living on Longboat Key – Neptune Condominium Welcome to your island retreat at Neptune on Longboat Key, a charming boutique community just moments from the Gulf of Mexico. This beautifully updated 1-bedroom, 1-bath condominium offers the perfect blend of comfort, style, and an unbeatable Longboat Key lifestyle. Step inside to discover a bright, open floor plan featuring luxury vinyl flooring, coastal-inspired décor, crown molding, and a tastefully renovated kitchen with cabinetry, updated appliances, quartz-look countertops, and a deep stainless sink. The spacious living and dining area flows effortlessly onto a screened lanai where you can relax with a morning coffee. The generous bedroom provides a peaceful retreat with abundant natural light, while the updated bath and thoughtful finishes create a move-in-ready coastal escape. Located on the desirable south end of Longboat Key, Neptune is a small boutique community known for its quiet atmosphere and convenient location. You're just a short stroll to the beach and only minutes from St. Armands Circle, where you'll enjoy world-class dining, shopping, and entertainment. Downtown Sarasota, cultural attractions, golf, boating, and marinas are also just a short drive away. Neptune is a small, low-density community with minimal common amenities, helping keep ownership simple while offering a peaceful island setting. Whether you're looking for a full-time residence, seasonal getaway, or investment opportunity, this turnkey-furnished condo offers an exceptional opportunity to own a piece of paradise on Longboat Key.
Listing is courtesy of: MANGROVE REALTY ASSOCIATES
Bayshore High - A4698229 - 848 EVERGREEN WAY, LONGBOAT KEY, FL 34228 18 Days on yellowkey
$599,900 | Townhouse | 2 beds | 2.5 baths | 1 gar
Turn-Key Furnished Waterfront Townhome in Cedars East on Longboat Key! Beautifully updated and move-in ready, this desirable 2-bedroom, 2.5-bath residence offers one of the best locations within Cedars East, featuring tranquil water views from the spacious primary suite and an expanded, open-concept living area. The updated kitchen showcases shaker-style cabinetry, granite countertops, stainless steel appliances, and abundant workspace, flowing seamlessly into the spacious dining and living areas. Turn-key furnishings make this home truly move-in ready—ideal as a full-time residence, seasonal retreat, or investment property. Life at Cedars East offers the perfect blend of resort-style amenities and relaxed coastal living. Residents enjoy access to a heated junior Olympic-sized pool, Har-Tru tennis courts, pickleball, fitness center, clubhouse, pro shop, fishing pier, kayak launch, scenic mangrove boardwalks, and an on-site restaurant and tiki bar. (Pool membership is included with ownership. Some amenities require optional club membership.) Ideally located just minutes from the sandy beaches of Longboat Key, St. Armands Circle, Anna Maria Island, championship golf, waterfront dining, shopping, Joan M. Durante Park, and vibrant downtown Sarasota, this exceptional property offers the perfect combination of location, lifestyle, and value in one of Longboat Key's most sought-after communities.
Listing is courtesy of: DOUGLAS ELLIMAN
Booker High - A4697519 - 455 LONGBOAT CLUB RD #PH8, LONGBOAT KEY, FL 34228 21 Days on yellowkey
$2,700,900 | Condo | 3 beds | 3.5 baths
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
Booker High - A4697978 - 2600 HARBOURSIDE DRIVE #R-13, LONGBOAT KEY, FL 34228 22 Days on yellowkey
$400,000 | Dock-Rackominium
Stunning Sarasota Bay Views! An easy access slip with the views to go along with the superb amenity package, Slip R-13 at Longboat Key Club Moorings Marina provides one of the most desired locations as a Yacht Club Member slip in the Marina. With the slip measuring 80 x 23.5, and a usable beam of 19 feet and extra wide finger pier. This is a desired 'inside the T-head' slip location. The Longboat Key Club Moorings Marina is a World Class deep water marina providing direct access to Sarasota Bay and ICW. Yacht Club membership at the Longboat Key Club Moorings provides members access to the private clubhouse, which is well appointed with TV, conference room, private pool area, outside seating and tables, grill, and bathhouse all in a relaxing atmosphere. Additionally, the Longboat Key Club offers multiple restaurants, world class tennis, pickleball and golf facilities, fitness center, with spa and beach access. The Marina is also located within close proximity to Publix, CVS, and world class shopping at St. Armand's Circle. The longest vessel this slip will accommodate is 75 feet. Beam depends on the vessel type and measure. Membership in the Longboat Key Club is required.
Listing is courtesy of: LBRE LLC
Riverview High - A4697649 - 500 HARBOR COVE CIR, LONGBOAT KEY, FL 34228 25 Days on yellowkey
$12,250,000 | Single Family Home | 5 beds | 5.5 baths | 4 gar
Under Construction. Now nearing completion and expected to be delivered in approximately 60 days. Positioned within the exclusive Harbor Section of Bay Isles on Longboat Key, 500 Harbor Cove Circle is a newly constructed waterfront estate offering a rare combination of exceptional boating access, modern architecture, resort-inspired living, and one of the Gulf Coast’s most coveted addresses. Located behind the double gates of Bay Isles and directly across from The St. Regis Longboat Key Resort, residents enjoy immediate proximity to world-class hospitality, fine dining, marina services, championship golf, and tennis, while ownership includes access to the Bay Isles Beach Club. Encompassing 5,120 square feet under air and 8,564 square feet total, the residence features 5 bedrooms, 5 full baths, 1 half bath, a private office, elevator access to all levels, and a 4-car garage. A fully integrated smart home automation system provides seamless control of lighting, climate, security, audio, window treatments, pool and spa functions, and key home systems throughout the property. The arrival experience unfolds through a lagoon-inspired reflecting pool, floating stairway, and lush tropical landscaping, creating a dramatic resort-style arrival. Architectural lighting, natural stone, warm wood accents, and expansive walls of glass establish a sophisticated coastal aesthetic throughout the residence. Inside, expansive living spaces are enhanced by Venetian plaster, custom millwork, large-format stone surfaces, and carefully curated architectural details. One of the home’s defining architectural statements is a dramatic 20+ foot monolithic travertine feature wall wrapping an entire corner of the residence, creating a striking design element rarely found in residential construction. The chef’s kitchen is anchored by an oversized Calacatta marble waterfall island, premium custom cabinetry, integrated appliances, and generous entertaining space. Designed for seamless indoor-outdoor living, the residence opens to expansive covered terraces, a resort-style pool and spa, and a fully equipped outdoor kitchen featuring a grill, pizza oven, refrigeration, and multiple gathering spaces. Wellness-focused amenities include a private fitness area, sauna, cold plunge, and dedicated spaces for relaxation and recovery, creating a private wellness retreat. For boating enthusiasts, the property offers approximately 100 feet of protected waterfront frontage with direct access to Sarasota Bay and the Gulf of Mexico in less than two minutes. The dock is designed to accommodate a substantial yacht while still providing room for multiple additional lifts for a tender, fishing boat, personal watercraft, and other recreational vessels—an increasingly rare offering among Florida’s premier waterfront estates. One of the Gulf Coast’s rare opportunities to enjoy new construction, large-yacht capability, and resort-inspired living within the exclusive Harbor Section of Bay Isles.
Booker High - A4696535 - 549 HALYARD LN, LONGBOAT KEY, FL 34228 25 Days on yellowkey
$2,195,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
This is the one * PERFECTLY POSITIONED ON A QUIET CUL DE SAC STREET AT THE PREFERRED SOUTH END OF LONGBOAT KEY * Located on the QUIET END OF THE CANAL with OPEN WATER JUST BEYOND YOUR DOCK and the PRIVATE BEACH ACCESS ONLY MINUTES AWAY * A quick 3 minute cruise to Sarasota Bay & the ICW & The GULF * This coveted Country Club Shores IV home has been LOVINGLY RENOVATED with a NEW Kitchen & modern amenities while retaining its classic charm * NEW KITCHEN CABINETS * NATURAL GAS STOVE * GE CAFE APPLIANCES * NEW Solid Core Doors * FULL HURRICANE PROTECTION * NEW TILE Flooring throughout * 2 Car Garage has a NEW Mini Split A/C * Primary Suite with a Spa-style Bath featuring a LARGE Walk-in Shower * BEAUTIFUL VIEWS OF YOUR POOL & PRIVATE CANAL * This THOUGHTFULLY CURATED HOME is an open floor plan * The additional Bedrooms are well-appointed and located in a way that allows for guest privacy * Impact Sliding Glass Doors surround the Outdoor Area * ROOF IS 9 YEARS YOUNG * WATER HEATER IS 3 YEARS YOUNG * All of this wraps your Caged Pool with Paver Decking and a Paver Walkway to your 2021 NEW SEAWALL & COMPOSITE DOCK with a 10,000lb Boat Lift & 2 Additional NEW Jetski Lifts PLUS a 2-step down Kayak Dock Launch with Power & Water * THIS IS A BOATER'S DREAM * The PERFECT HOME & OUTDOOR OASIS to entertain family & friends or just simply relaxing in your slice of paradise * PRIDE OF OWNERSHIP SHOWS IN THIS IMMACULATE HOME * Furniture is available * Just bring your suitcase * Country Club Shores is a well established waterfront neighborhood offering DEEDED BEACH ACCESS with a convenient south end location close to ST ARMAND'S CIRCLE, The new ST REGIS, and even downtown Sarasota * Join the Longboat Key Club offering 45 holes of championship golf & world class tennis * Your family will love this home * One look & you'll fall in love! *
Bayshore High - A4697241 - 4350 CHATHAM DR #105, LONGBOAT KEY, FL 34228 29 Days on yellowkey
$310,000 | Condo | 1 beds | 1.0 baths | 1 car
Exceptional opportunity to own a beautifully furnished waterfront residence in a gated, amenity-rich boating community. This one-bedroom unit features hurricane-impact sliding glass doors and windows, allowing abundant natural light while providing peace of mind. Enjoy waterfront living with access to a private beach located at 4415 Gulf of Mexico Drive, complete with gated parking, indoor facilities, and beachside amenities. Residents have access to an impressive array of community features, including four heated swimming pools, a spacious fitness center, pickleball courts, tennis courts, kayak and bicycle storage, and a vibrant boating community with first-come, first-served boat slips. Additional amenities include a banquet hall and numerous social and recreational opportunities. Whether you're seeking a full-time residence, seasonal retreat, or investment property, this waterfront gem offers the perfect combination of coastal lifestyle, convenience, and value.
Bayshore High - A4697248 - 660 LINLEY ST, LONGBOAT KEY, FL 34228 31 Days on yellowkey
$799,000 | Single Family Home | 3 beds | 3.0 baths
Owner Financing Available! Nestled in the heart of Longboat Key's coveted historic Longbeach Village, this exceptional island retreat offers 3 bedrooms and 3 bathrooms across two charming Key West-style cottages just moments from both the most pristine Gulf beaches and beautiful Sarasota Bay. This rare property blends timeless coastal elegance with modern updates in a private, landscaped setting. The main residence features a bright, open floor plan and an updated kitchen with quartz countertops, hardwood cabinetry, newer appliances, and abundant natural light. The detached guest cottage offers a private 1-bedroom, 1-bath layout complete with its own kitchen and entrance, providing the perfect space for guests, extended family, or added flexibility. Outdoor living is equally inviting with a spacious entertaining deck, tiki bar, and mature tropical landscaping that creates a true sense of privacy and retreat, with room to add a pool. Recent improvements include a new roof on the main residence (2026), Hardie Board siding, updated cabinetry, quartz countertops, updated appliances throughout, fresh paint, and a newer A/C system, offering peace of mind and modern comfort. With proven rental income, this property serves as an exceptional investment opportunity while maintaining strong personal use potential. Situated in the highly desirable “Village“, one of the most charming, inviting, and community-driven neighborhoods on Longboat Key, residents enjoy a rare blend of coastal character and close-knit island living. Just moments from Whitney Beach, community fishing docks, a boat and kayak launch, and exclusive waterfront dining destinations such as Mar Vista and The Shore, this home captures the essence of luxury island living in one of the island’s most beloved enclaves. Schedule your private showing TODAY before it’s gone !!
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S
Sarasota High - A4697037 - 602 BUTTONWOOD DR, LONGBOAT KEY, FL 34228 31 Days on yellowkey
$1,399,000 | Single Family Home | 3 beds | 3.0 baths | 2 gar
Expect luxury living and a world of conveniences within the serene enclave of Buttonwood Harbour on Longboat Key, where care and impeccable style converge in this 3BR/3BA tropical oasis. As you approach, the vast circular paver drive, embraced by lush, professionally maintained landscape, sets the stage for what awaits beyond the architecturally pleasing covered front entryway. Step inside to discover the attention to detail that defines this updated home, as gorgeous new tile floors throughout grace and harmonize with neutral tones and exquisite touches, including stately plantation shutters adorning every window. The flowing floor plan effortlessly guides you to the expansive pool area, blending indoor elegance with outdoor convenience. The beautifully remodeled kitchen is both stylish and functional, seamlessly connected to the living room, and featuring a large breakfast Island, tile backsplash, a wine refrigerator, and Bosch appliances. Relax in the cozy Florida room, which offers a tranquil retreat with walls of sliders that blur the boundaries between indoor and outdoor living. Outside, the sparkling heated pool beckons, surrounded by ample space on the lanai for entertaining or simply basking in the tropical ambiance. The expansive primary suite is a sanctuary of comfort, with slider access to the pool area, new tile flooring, and a remodeled primary bath boasting dual vanities and a glass-enclosed walk-in shower adorned with stunning tilework. Equally inviting, the two guest accommodations offer spacious comfort, with elegantly remodeled bathrooms. Set in a prized mid-key location, Buttonwood Harbour offers residents a short walk to the beach and a community Harbor with boat slips available to lease.
Booker High - TB8518960 - 521 BAYPORT WAY #521, LONGBOAT KEY, FL 34228 33 Days on yellowkey
$619,900 Reduced | Condo | 2 beds | 2.0 baths | 1 car
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
Booker High - A4696547 - 350 GULF OF MEXICO DR #213, LONGBOAT KEY, FL 34228 35 Days on yellowkey
$899,500 | Condo | 3 beds | 2.5 baths | 2 gar
Welcome to one of Longboat Key's premier bayfront communities, Tangerine Bay Club, where your days are spent like you live at a luxury resort! This three bedroom, 2 and a half bath elevated residence offers spacious living with gorgeous views of the mote style lagoon, spectacular resort style pool and Sarasota Bay. A private 2 car garage only adds to the many benefits of living here. Did we mention the day dock and pier over Sarasota Bay? The community gym overlooking the gorgeous pool? The Tennis and pickleball courts? The ability to purchase a membership at the Bay Isles Beach club for only a nominal yearly fee? This is truly island living at its best! A welcoming front entrance courtyard allows for a wonderful arrival spot just steps from the elevator yet this unit, being a corner residence, feels very private. Once inside you'll be immediately impressed with the light filled spaces that allow for you to enjoy the incredible views from multiple large windows. A balcony accessed from the great room and the Primary bedroom is a spot you'll want to enjoy every morning with your coffee and every evening with your cold beverage. Just a short distance from multiple restaurants, the Longboat Key Club, The St.Regis resort and the bridge that takes you over to St.Armands Circle and then onto the cultural mecca of downtown Sarasota....at a price that makes it easy to imagine. Whether you choose to renovate and make it your own or enjoy it just as it is, this is one you will want to see!
Booker High - A4696825 - 100 SANDS POINT RD #303, LONGBOAT KEY, FL 34228 36 Days on yellowkey
$915,000 | Condo | 3 beds | 2.0 baths | 1 car
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.