Location: Longboat Key , 34228
Do Not Show Listings
605 SUTTON PL #201, LONGBOAT KEY, FL 34228
$619,000112 Days on yellowkey MLS ID: A4687586
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1148 Built: 1973 Tax: $6,756 (2025)Community: Sutton PlaceCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,756
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2025
Middle School: Martha B. King Middle
Remarks: This is the one you have been waiting for!! INCREDIBLE UNOBSTRUCTED BAY VIEWS & BREATHTAKING SUNRISES from this light-filled CORNER unit in the beach-to-bay community of Sutton Place. Enjoy stunning vistas from nearly every room through impact windows and doors! Meticulously maintained and beautifully renovated, this spacious two-bedroom, two-bath coastal retreat is truly exceptional. The thoughtfully designed open concept chef’s kitchen with premium cabinetry, plentiful storage, and Cambria quartz countertops seamlessly connects to the expansive living area through a custom dining island with wraparound seating. Plantation shutters throughout the kitchen and living area add to the coastal island feel. The enclosed lanai, featuring walls of glass that span along the rear of the unit, provides an ideal setting for morning coffee, evening relaxation, remote work, or accommodating additional guests. The spacious primary and secondary bedrooms provide exceptional views, each with direct access to the lanai through impact-rated sliding doors. The serene primary bedroom boasts a generous walk-in closet fitted with a custom organizer and an elegantly renovated bathroom with a walk-in shower, complete with a linen closet. The secondary bedroom offers ample storage with a double closet, also fitted with custom organizers. The adjacent guest bath has been tastefully renovated. Parking is easy with a covered, assigned space in a convenient location, plus plenty of overflow and guest parking. While the stairs are easily accessible; there is also an elevator for added convenience. The in-building storage unit provides extra space for any additional storage needs. Sutton Place offers a wide range of amenities, including two heated swimming pools, a community clubhouse, marina facilities with boat slips (current wait list but only $300 annually!!), kayak storage equipped with electric launch, a fish cleaning station, designated grilling areas, car wash stations, and deeded beach access with private beach pavilion featuring storage lockers, showers, and restrooms. The community successfully endured the recent storms, experiencing minimal overall damage and no impact to any individual units. With its exceptional location, unmatched views, and wonderful amenities, this property is an opportunity not to be missed! Schedule your private showing today!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Melissa Rodocker (703-969-2345)
392 FIREHOUSE LN, LONGBOAT KEY, FL 34228
$1,449,00019 Days on yellowkey MLS ID: A4698365
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1761 Built: 2004Monthly Fee: $467 Tax: $17,566 (2025)Community: Conrad BeachSingle Family
Taxes:$17,566
Elementary School: None
High School: None
Middle School: None
Remarks: Located on the coveted west side of Gulf of Mexico Drive, just steps from the beach, 392 Firehouse offers the relaxed coastal lifestyle Longboat Key is known for. Nestled on a quiet cul-de-sac surrounded exclusively by charming Key West-style homes, this beautifully updated residence blends timeless island architecture with thoughtful modern enhancements. Residents also enjoy the community pool located directly across the street, along with the convenience of walking to three of Longbeach Village's beloved restaurants, making it easy to embrace the island lifestyle. Designed for effortless indoor-outdoor living, the home features an enlarged rear deck, fully equipped outdoor kitchen, outdoor shower, and a gas fire pit—creating the perfect setting for entertaining or unwinding after a day at the beach. Hurricane-impact sliding glass doors provide a seamless connection to the outdoor living spaces while filling the home with natural light. The home's curb appeal has been thoughtfully elevated with an updated exterior stucco finish, classic Bahama shutters, an artistic shell stone paver driveway, new professional landscaping, and landscape lighting that enhances the property after sunset. Inside, refinished hardwood floors bring warmth and character throughout, while sleek glass railings in the loft add a contemporary architectural element. The primary suite is enhanced with custom California Closet built-ins, providing exceptional organization and storage. Additional improvements include a new air conditioning system (2023), Tesla electric vehicle charging station, and an irrigation system. Offering an exceptional location just steps from the Gulf beaches, within one of Longboat Key's most charming coastal enclaves, this meticulously updated home embodies the very best of island living.
Listing is courtesy of: BRISTA REALTY LLC (941-373-0500)
Listing Agent: Gina Ursini (941-812-4894)
4500 GULF OF MEXICO DR #3, LONGBOAT KEY, FL 34228
$739,000113 Days on yellowkey MLS ID: A4685838
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1325 Built: 1975 Tax: $2,843 (2025)Community: Windward Bay AmdCondo
Taxes:$2,843
Remarks: GORGEOUS BAYFRONT PENTHOUSE VIEWS--RARE TOP FLOOR OPPORTUNITY!! Nestled in the heart of a vibrant Longboat Key Community, this stunning two-bedroom, two-bathroom condo offers unparralled water views of Sarasota bay, creating a great backdrop for both sunrises and sunsets. Step inside and be captivated by the breathtaking scenery and spacious design that blends coastal living with sophistication. Beautifully renovated with new floor to ceiling hurricane windows, this condo seamlessly integrates the living and dining areas with an open kitchen featuring stone countertops, custom cabinets and new Stainless steel appliances. The light-filled primary bedroom boasts two closets, one being a walkin complete with built in ample storage. Both bathrooms have been tastefully renovated, offering a spa-like ambiance that invites relaxation. Take in manatee and dolphin viewing from the expansive Florida Room or relax in style looking out the huge picture window as the sun rises over the bay. This professionally managed, pet friendly community offers an array of amenities including 26 acres of landscaped ground, 2 marinas, 2 heated pools, tennis courts, pickle ball courts, state-of-the art Fitness Center, library and Community Clubhouse. Take advantage of the Deeded Beach Access just steps away. With its prime location, stunning views and extensive amenities, this property represents a rare opportunity to embrace the best of waterfront living.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Marcela Terrell (941-929-3010)
1445 GULF OF MEXICO DR #101, LONGBOAT KEY, FL 34228
$1,180,000140 Days on yellowkey MLS ID: A4684021
REDUCED by $15,000 (1.3%) on 06/25/2026
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2092 Built: 1982 Tax: $11,749 (2025)Community: Players Club IiiSpa: YesCondo
Taxes:$11,749
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: Step into this highly desirable corner residence featuring three bedrooms, three full baths, and an expansive 36’ x 11’ sunroom at The Players Club. You’ll immediately be drawn to the impressive 31-foot balcony, offering sweeping views of the resort-style pool, lush, landscaped grounds, and breathtaking sunsets over the Gulf of Mexico. The outdoor space is perfect for alfresco dining, entertaining friends, or simply enjoying the tranquil Gulf breezes. Inside, the sun-filled kitchen is thoughtfully designed with custom cabinetry and a built-in breakfast table that expands both workspace and storage. It flows seamlessly into the main living and dining areas, creating a warm and open environment for entertaining or daily living. Just off the kitchen, elegant French doors open to a generous multipurpose sunroom that can serve as a home office, reading retreat, casual lounge, or even a fourth bedroom for guests. The owner’s suite provides a private sanctuary with a spa-inspired bathroom featuring a soaking tub, separate glass-enclosed shower, dual vanities, and a spacious walk-in closet. The second bedroom functions as a true secondary master, complete with dual sinks, a full vanity, and a fitted walk-in closet, offering comfort and privacy for family or visitors. A third bedroom adds flexibility for guests, workspace, or hobbies. A unique feature of this residence is the private garage, offering rare security and convenience for residents, plus an additional covered parking space underneath the building for extra guest or secondary vehicle use. Set on 11 acres of beachfront with 560 feet of Gulf frontage, The Players Club offers abundant green space, four Har-Tru tennis courts, a 70-foot heated saltwater pool, spa, fitness center, renovated clubhouse with catering kitchen, outdoor grilling areas, putting green, on-site management, and fully funded reserves. Just minutes from St. Armands Circle, downtown Longboat Key, and Longboat Key Club, with championship golf, premier tennis, and a deep-water marina, this corner residence blends privacy, convenience, and resort-style coastal living. Units with this versatile layout and resort-ready features are highly sought after. Offered partially furnished. Seller is willing to discuss a subsidy on the quarterly condominium fee for reserve increase over the next two years!
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
677 LANDS END DR, LONGBOAT KEY, FL 34228
$2,695,000151 Days on yellowkey MLS ID: A4682565
REDUCED by $95,000 (3.4%) on 06/12/2026
Bed: 3 Bath: 3.0 Gar: 4 Liv Area Sq Ft: 4182 Built: 1989Monthly Fee: $967 Tax: $33,361 (2025)Community: Lands EndSpa: NoSingle Family
Taxes:$33,361
Middle School: W.D. Sugg Middle
Remarks: Experience the timeless appeal of a quintessential Florida island home, immersed in a lush tropical waterfront setting on Longboat Key. Elevated above a serene natural bayou off Sarasota Bay, this distinctive residence embodies the relaxed elegance of island living, with soaring ceilings, expansive wraparound decks, and pristine Gulf beaches just moments away. Launch a kayak from your private dock, enjoy exceptional fishing and bird-watching from your backyard, or keep your boat in one of the community's deepwater slips on the open bay. The association offers slips up to 43 feet in length, and either your private dock on the bayou or a bayfront slip may accommodate an optional boat lift. The spacious elevated residence is anchored by a dramatic great room featuring vaulted cedar ceilings and exposed beams. An expansive sunroom with a bar area and handcrafted display shelving, a dedicated library, an inviting family room, and a private office with extensive built-in cabinetry contribute to the home's distinctive character. The entire main living area is thoughtfully arranged on a single level. Extensive decking welcomes you at the front entry and wraps around a lush central atrium courtyard, creating exceptional spaces for outdoor dining, entertaining, and relaxation. A shaded cabana-inspired retreat offers comfort throughout the day, while the setting is equally suited for the addition of an elevated outdoor spa. The kitchen, centered around a generous island, is perfectly positioned for gathering with family and friends. The primary suite features a wall of windows overlooking the tranquil bayou, dual walk-in closets, and an additional wall of custom closet storage. A desirable split floor plan creates a private guest wing with two additional bedrooms and baths. Each guest room enjoys direct access to the surrounding decks and views of the tropical atrium. Two garages accommodate up to four vehicles and provide ample space for boats, golf carts, paddleboards, and additional storage. Most furnishings are included. Within Land's End, an intimate gated enclave of just 12 residences, owners enjoy maintenance-free landscaping, a heated swimming pool, tennis and pickleball courts, and beautifully landscaped grounds nestled among mature trees for exceptional privacy and convenient bay access. From here, a short walk or golf cart ride leads to the Gulf beach and popular island dining destinations, including Shore Longboat Key, Mar Vista Dockside Restaurant, and Whitney's. Nearby waterfront cafés, boutique shopping, fitness facilities, and a Pilates studio further enhance the island lifestyle. Enjoy breathtaking Gulf sunsets and tranquil bay sunrises from this exceptional waterfront community. Rarely does a property so perfectly capture the spirit of Old Florida, where tropical beauty, boating, nature, and beachside living come together in one of Longboat Key's most treasured island enclaves.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Cindy Fischer (941-465-1124)
1561 GULF OF MEXICO DR #403, LONGBOAT KEY, FL 34228
$13,000,000613 Days on yellowkey MLS ID: A4627926
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4187 Built: 2024 Tax: $81,320 (2025)Community: St. Regis Longboat KeyCondo
Taxes:$81,320
Remarks: Experience unparalleled luxury with breathtaking views of the Gulf of Mexico in the Armand Building. This exceptional residence features an open-concept floorplan designed for entertaining, complete with floor-to-ceiling glass doors that lead to an expansive terrace outfitted with a built-in gas grill, perfect for seamless indoor-outdoor living. Ideal for multi-generational gatherings, the clubroom serves as a fantastic bonus space, featuring a wet bar equipped with an ice maker, bar sink, and wine fridge. The gourmet kitchen is a chef’s dream, showcasing top-of-the-line Wolf and Sub-Zero appliances, including a 6-burner gas cooktop, double ovens, and an integrated cabinet front side-by-side refrigerator/freezer. A semi-private elevator with keyless entry transports you directly from your private two-car garage to your residence. The owner’s suite offers a spacious walk-in closet, a luxurious soaking tub, a frameless walk-in shower, and dual vanities with separate water closets. Designed with technology-ready infrastructure, this home allows for easy customization of your automation preferences. Located within the first branded residential community and ultra-luxe 5-star resort hotel on the Gulf, The Residences at The St. Regis Longboat Key blend legendary service with the allure of a serene seaside retreat. Spanning over 17 acres with 800 feet of direct beachfront, residents can indulge in unparalleled amenities, including signature St. Regis Butler and Concierge services, a world-renowned spa, in-residence dining, a resident-only pool and spa, a private clubhouse, a fitness center, and beachside cabanas. Discover a life of luxury and leisure at The Residences at The St. Regis Longboat Key—where every day feels like a getaway. The owner will consider a lease purchase with acceptable terms on this residence.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Michael Moulton (941-928-3559)
595 BOWSPRIT LN, LONGBOAT KEY, FL 34228
$3,099,000273 Days on yellowkey MLS ID: A4668868
REDUCED by $41,000 (1.3%) on 07/05/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2550 Built: 1966Monthly Fee: $21 Tax: $26,814 (2025)Community: Country Club ShoresSingle Family
Taxes:$26,814
Remarks: Longboat Key Waterfront Luxury. Experience the ultimate in waterfront living in this 4-bedroom, 2.5-bath Country Club Shores residence, tucked just off Sarasota Bay on a nice canal with quick access to the Gulf, sandbars, and every boating adventure Sarasota has to offer. A private dock, two boat lifts (20,000 lb and 7,000 lb), new seawall, and a custom fish cleaning station create a true boater’s paradise, while canal and bay views enhance the coastal setting. After a day of boating, sandbar hopping, fishing, or cruising the bay, come home to your heated pool, travertine-decked outdoor retreat. Retractable glass sliders, and pool bar blur the line between indoors and out, making this the perfect place to gather, unwind, and relive the day’s best moments on the water. Thoughtfully remodeled twice in recent years, the home blends refined coastal style with exceptional updates including a 2016 effective build year, roof, plumbing, electrical, PGT hurricane-impact windows and sliders, and two new A/C systems in 2024. The chef’s kitchen is a standout, featuring custom Devittori cabinetry, leathered granite, a dramatic 11’x5’ island, and premium Sub-Zero and Wolf appliances. Deeded private beach access, nearby Longboat Key Club amenities, and close proximity to St. Armands Circle and Downtown Sarasota complete this exceptional island offering.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Melissa Gissinger (941-404-2722)
552 JUAN ANASCO DRIVE, LONGBOAT KEY, FL 34228
$975,000162 Days on yellowkey MLS ID: A4680786
0 Days Off yellowkey (back on 7/3/2026)
REDUCED by $24,999 (2.5%) on 06/03/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 1846 Built: 1960 Tax: $17,419 (2024)Community: Sleepy Lagoon ParkSingle Family
Taxes:$17,419
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Imagine living the coastal lifestyle only dreams are made of! Wake each morning to the sunrise over your local beach—just a short stroll down the street—where you can sink your toes into sugary white sand, take an early walk, or collect seashells along the shore. Return home to enjoy coffee outdoors by your heated pool, relaxing on the deck as tranquil water views set the tone for the day. Take a refreshing dip, then unwind as nature’s canvas unfolds before you, with shifting light and brilliant shades of blue and azure. In the evening, hop on your boat from your backyard and cruise effortlessly to waterfront restaurants and sunset destinations. With a 20,000-lb boat lift, personal watercraft lift, and a 40-foot dock on a deep-water canal, you’ll enjoy immediate access to Sarasota Bay, the Intracoastal Waterway, and the Gulf—with no fixed bridges along the way. End your days with breathtaking sunsets as the sky ignites in color, dolphins play, and manatees glide by. Inside, the home offers an optimal floor plan ready for your personal touches. The spacious eat-in kitchen features an expansive island perfect for casual entertaining, complemented by new stainless-steel appliances. A wall of sliding glass doors seamlessly blends indoor and outdoor living, filling the home with natural light and water views. All main living areas open to the pool and outdoor spaces. Recent updates include a new AC system and a recently refinished pool. The home offers three bedrooms and four baths, with the flexibility to modify the layout or easily add a fourth bedroom. A wood-burning fireplace adds warmth and charm to the living room. Located on the barrier island of Longboat Key, this exceptional property is perfectly suited for the most discerning buyers. Enjoy nearby golf, pickleball, boutique shopping, and dining, with St. Armands Circle and downtown Sarasota just minutes away. Convenient access to SRQ Airport makes this an ideal full-time residence or luxury vacation retreat. Call today to schedule your private showing and experience coastal living at its finest.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER (941-729-7400)
Listing Agent: Kathy Cahill (941-807-3565)
5231 GULF OF MEXICO DR #104, LONGBOAT KEY, FL 34228
$499,000196 Days on yellowkey MLS ID: A4676730
REDUCED by $46,000 (8.4%) on 06/15/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 720 Built: 1973 Tax: $6,784 (2024)Community: Covert IiCondo
Taxes:$6,784
Remarks: Have you dreamed of the perfect island getaway situated right on a gorgeous stretch of beach on Longboat Key? This is by far the lowest priced direct beachfront condo on the entire island and it is already completely updated! Whether you decide to use it yourself or use it as an investment with outstanding monthly rental income availability, this is the one. With a fabulous ground floor location, you can have your toes in the sand in only a few steps! This condo offers Italian porcelain tile throughout and a completely new kitchen with beautiful counter tops, all new cabinets and new appliances. The bathroom has been beautifully updated as well and features custom tile work in a seaside theme. The view is fabulous in either direction with the sparkling pool out front and the gorgeous Gulf of Mexico out back. The open living and dining area allows plenty of space to entertain or to quietly contemplate whether it’s a beach day, a day for a soak in the pool or a walk to the Covert bayside fishing pier. The bedroom offers the same stunning beach view and features storm rated sliders to the screened in lanai. The midkey location allows for easy access to multiple restaurants and shopping. The tree filled mangrove trails of Joan Durante Park are a birders’ paradise and the 12 mile long bike path give you many options to soak in the sun while getting in your daily exercise. This is island living at its best at a price you may never thought you could find!
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
2850 GULF OF MEXICO DR #4, LONGBOAT KEY, FL 34228
$325,00015 Days on yellowkey MLS ID: A4698791
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 532 Built: 1967 Tax: $3,248 (2025)Community: Neptune On Longboat KeyCondo
Taxes:$3,248
Remarks: 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 (941-957-0080)
Listing Agent: Michael Renick Pllc (941-400-8735)
1135 GULF OF MEXICO DR #505, LONGBOAT KEY, FL 34228
$1,175,00056 Days on yellowkey MLS ID: A4694362
5 Days Off yellowkey (back on 7/2/2026)
REDUCED by $125,000 (9.6%) on 06/03/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1503 Built: 1980 Tax: $13,396 (2025)Community: Beachplace ICondo
Taxes:$13,396
Remarks: Under contract-accepting backup offers. DIRECT BEACH FRONT VIEWS AND FIFTH FLOOR EXTRORDINARY PANORAMA! Come visit this property soon, as it boasts Two Parking spots, one in garage, near the elevator and one outside near the front door. Reimagined kitchen with lots of cupboard space, all KITCHEN AID appliances, 2019 Air Handler, never rented and barely occupied. Furnished with exquisite taste and comfortable living space! Beachplace is unique from other communities due to its high rental appeal for returning families! Enjoy the great Olympic size pool located in the center of the complex, plus the oversized hot tub, workout facilities, tennis courts, pickle ball and more! Not to forget the covered baby pool for ages 3 and under! The highest and most sought after units are always BEACHFRONT, holding the best value!
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: James Weingart (440-623-9068)
791 BROADWAY ST, LONGBOAT KEY, FL 34228
$1,625,00058 Days on yellowkey MLS ID: A4694059
Bed: 2 Bath: 2.0 Gar: 4 Liv Area Sq Ft: 2236 Built: 1995 Tax: $9,600 (2025)Community: Longbeach VillageSingle Family
Taxes:$9,600
Remarks: Welcome home to 791 Broadway, nestled in the heart of historic Longbeach Village on the North end of prestigious Longboat Key. This elevated island-style residence offers the perfect blend of coastal charm, comfort, and relaxed island living. Thoughtfully designed across multiple levels including a large 11x30 third floor FLEX SPACE that could easily be converted into a 3RD BEDROOM. This home captures beautiful morning sunrises, colorful sunsets, and stunning views of Sarasota Bay and the intracoastal waterway. From the moment you step inside, you are greeted by an abundance of natural light, soaring ceilings, plantation shutters, and inviting open spaces that are ideal for both everyday living and entertaining. The property offers wonderful flexibility, including an oversized garage with plenty of room for golf carts, kayaks, bicycles, beach gear, and more. The outdoor living areas are equally inviting, with several unique spaces to relax and enjoy the surroundings — from the covered front porch to the rear deck overlooking the water, along with the peaceful sound of multiple water features throughout the property. Recent updates add comfort and peace of mind, including new impact-resistant and energy-efficient windows, two AC units, updated flooring, and many additional improvements that make this home feel warm, welcoming, and move-in ready. Enjoy the charm and convenience of the Village, just a short stroll from community fishing piers, a boat launch, exceptional dining, and the white sandy beaches and turquoise waters of the Gulf of Mexico. This is a wonderful opportunity to experience the laid-back Longboat Key lifestyle in one of the island’s most beloved neighborhoods.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Matthew Voss (941-402-8799)
5270 GULF OF MEXICO DR #508, LONGBOAT KEY, FL 34228
$754,900228 Days on yellowkey MLS ID: A4673695
REDUCED by $20,000 (2.6%) on 07/02/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1460 Built: 1974 Tax: $4,861 (2025)Community: The Banyan Bay ClubCondo
Taxes:$4,861
Remarks: Rarely available and beautifully positioned, this 3-bedroom, 3-bath fully furnished residence with UNOBSTRUCTED FULL BAY VIEWS invites you to experience true beach-to-bay living in the coveted community of Banyan Bay on the north end of Longboat Key. From sunrise coffees on your private terrace to evenings spent watching dolphins glide across the bay, this home offers an effortless blend of comfort, coastal elegance, and unforgettable daily moments. Set within an intimate community of just 26 Bayside and 18 Gulf side residences, Banyan Bay provides a peaceful retreat with exceptional amenities. Start your mornings with a stroll along your private Gulf beach access, join neighbors for a friendly match on the tennis/pickleball court, launch a kayak directly onto the bay, or unwind by the heated pool after a day on the water. A day dock/fishing pier, fitness center, clubhouse, and convenient bicycle storage further enhance the lifestyle of this warm, social community. Inside, more than 1,400 square feet of thoughtfully designed living space showcases a spacious kitchen with granite countertops, SS appliances, and a breakfast bar and nook ideal for casual dining or gathering with friends. The open great-room layout features soaring ceilings that fill the home with natural light and frame the captivating bayfront scenery. The primary suite offers its own private terrace overlooking the shimmering water—perfect for quiet mornings or evening breezes. A guest suite on the main level ensures comfort and privacy, while a charming spiral staircase leads to a versatile loft and a spacious third bedroom suite—ideal for hosting visitors, working remotely, or enjoying a dedicated creative space. Terra cotta tile flooring throughout the first level brings warmth and coastal character, while Tommy Bahama inspired finishes make this turnkey furnished residence truly move-in-ready. Beyond the community, you’ll find yourself within walking-distance to restaurants and the Centre Shops. Durante Park and the Longboat Key Center for the Arts are just moments away, adding convenience and charm to the neighborhood. Discover the rare combination of lifestyle, location, and waterfront living that only Banyan Bay can offer—where every day feels like a coastal escape.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Beth Ann Boyer (941-780-6606)
548 HORNBLOWER LN, LONGBOAT KEY, FL 34228
$4,950,000276 Days on yellowkey MLS ID: A4668463
1 Days Off yellowkey (back on 6/5/2026)
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3976 Built: 2015Monthly Fee: $8 Tax: $47,046 (2024)Community: Country Club Shores Sec 02Spa: YesSingle Family
Taxes:$47,046
Remarks: Under contract-accepting backup offers. This exquisite home is sure to exceed expectations! This exceptional 4 bed/5 bath canal-front estate is located in coveted Country Club Shores, where chic architecture, thoughtful craftsmanship, and effortless coastal luxury converge. Designed by DSDG architects to maximize the contemporary sightlines and southern exposure, this Voight built custom residence offers a spectacular open floor plan and is positioned just three lots from the open waters of Sarasota Bay. This extraordinary residence is better-than-new with a recently installed metal roof, AC systems, and whole home generator and has been impeccably maintained. The home has been built to effortlessly withstand the Florida coastal environment while maintaining its magnificent beauty and clean lines. Boaters will appreciate the Trex dock equipped with a 20,000-lb boat lift, kayak and paddleboard racks, and convenient launch deck - providing quick, easy access to bay and Gulf waters. Inside, the home is both stunning and impressive with exquisite finishings and custom millwork. The first-floor owner’s suite is a luxurious retreat highlighted by soaring triple-coffered tray ceilings, tranquil views, and private pool access for a midnight swim. The spa-like bathroom is pure luxury. The chef’s kitchen is a true showpiece, featuring Viking appliances, a Sub-Zero Pro refrigerator, a walk-in pantry, expansive countertops, and a dramatic 14-foot quartz island perfect for large gatherings. The integrated dining area is framed by an aquarium window which emphasizes the tranquil water views. The family room is a natural extension of the kitchen and provides a generous area with direct access to the lanai, grille and dining areas and is perfect for enjoying movies, or just gathering with friends and family. The great room is spacious with large archways, gas fireplace, custom built-in shelving, and coffered shiplap ceilings which add to the drama of this cozy but elegant space. A wall of windows provides access to the covered lanai area and expands the feeling of openness highlighting the pool, sparkling spa, and water views. The second floor has been completely reimagined to elevate both style and function, offering three private guest suites, a versatile and spacious Florida room, wet bar, and a 300+ bottle state-of-the-art walk-in wine cellar. The enclosed upper lanai enhances ambiance and panoramic views. The Florida room provides a flexible space for enjoying sporting events or wine tastings, and includes a full bath for convenience. The 3 bedrooms on the second level are generous in size and 2 of the 3 include ensuite baths. Outdoor living is equally exceptional. The lanai with a Cypress-clad ceiling includes a new grill and dining area and pool bath, which steps down to the saltwater pool, spa, and sun deck - an ideal setting for entertaining or enjoying sunshine year-round. Additional features include a two-car garage with generous overhead storage, a rear enclosed storage compartment, and an electric vehicle charger. There is ample vertical height in the garage to add a car lift as an option. Residents of Country Club Shores enjoy private deeded beach access to the Gulf of Mexico, with optional golf and tennis memberships available at the nearby Resort at the Longboat Key Club. This is waterfront living at its finest - refined, relaxed, and designed to be enjoyed. A must-see property to fully appreciate the exceptional lifestyle, upgrades, and craftsmanship throughout.
Listing Agent: Kathy Callahan (941-900-8088)
721 BINNACLE POINT DR, LONGBOAT KEY, FL 34228
$1,499,000534 Days on yellowkey MLS ID: NS1083611
1 Days Off yellowkey (back on 7/2/2026)
REDUCED by $96,000 (6.0%) on 06/16/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3229 Built: 1973Monthly Fee: $50 Tax: $6,896 (2024)Community: Emerald HarborSpa: NoSingle Family
Taxes:$6,896
High School: Manatee High
Middle School: Electa Arcotte Lee Magnet
Remarks: Under contract-accepting backup offers. PREMIER LOCATION in Emerald Harbor -- HOUSE TO BE DEMOLISHED -- LOT IS GRADED AND READY TO BUILD -- Located on the apex of the WIDEST CANAL on Longboat Key, 721 Binnacle Point Drive is ready for a new owner with a new vision! The property has 96' of canal frontage with BRAND NEW Sea Wall (2024), 120' of street frontage, with just over 18,800 SF upon which to build your dream home. Build new and enjoy long views east and west down the canal and the beautiful light exposure. Emerald Harbor is one of Longboat Key's best neighborhoods - don't miss this opportunity to create your vision! There is a working, permitted sprinkler well on property. Private, deeded beach access for Emerald Harbor residents is just over 1100 feet away! *The 3/3 home on the property that was damaged by Hurricane has been removed.
Listing is courtesy of: KINCAID REALTY (386-428-7800)
Listing Agent: James Frost (386-299-9245)
4995 GULF OF MEXICO DR #500, LONGBOAT KEY, FL 34228
$5,695,000185 Days on yellowkey MLS ID: A4677613
0 Days Off yellowkey (back on 7/1/2026)
REDUCED by $200,000 (3.4%) on 05/11/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3344 Built: 2007 Tax: $47,519 (2024)Community: PositanoSpa: NoCondo
Taxes:$47,519
Remarks: Step right into the epitome of Florida beachfront luxury with this stunning first-floor Capri unit on Longboat Key. Nestled within the exclusive Positano community—an intimate 10-acre oasis of just 29 residences—this condo offers a seamless walkout straight to the pristine beach and the azure waters of the Gulf of Mexico. This is Florida living at its finest. The condo features a fantastic wrap-around terrace on the Gulf side, perfect for soaking in the outdoor splendor from morning coffee to sunset cocktails. The primary suite offers direct steps down to the private community pool, while additional terraces off the secondary bedrooms ensure both privacy and gorgeous views. Spanning a generous 3,343 square feet, this true three-bedroom, all en-suite residence boasts a Gulf-front gourmet kitchen with state-of-the-art appliances, an adjacent family gathering area, and an open-plan flow from the living room to the dining space. Floor-to-ceiling windows frame dramatic views of the Gulf and the beach, while beautiful porcelain tile floors, 10-foot ceilings, and crown molding add to the sense of refined elegance. You'll enjoy the convenience of a private, enclosed two-car garage and the exceptional amenities of the owner's club, including a state-of-the-art fitness center, catering kitchen, and a lounge with a fireplace, plasma TV, and surround sound. Outdoors, there's a 75-foot Olympic pool, spa, grilling area, and shaded cabanas, all set amidst lush tropical landscaping. Truly, this condo is as close to the beach as it gets on Longboat Key.
Listing is courtesy of: DEVELOPERS REALTY LBK, INC (941-799-9096)
Listing Agent: Reid Murphy (941-232-3304)
448 GULF OF MEXICO DR #A205, LONGBOAT KEY, FL 34228
$599,00086 Days on yellowkey MLS ID: A4690875
REDUCED by $30,000 (4.8%) on 05/11/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1306 Built: 1970 Tax: $5,089 (2025)Community: Bay HarbourCondo
Taxes:$5,089
Remarks: Enjoy the benefits of a well-managed waterfront community with just 39 residences and attractively low condominium association fees. Set within an intimate waterfront enclave, this Bay Harbour retreat captures the essence of refined island living. Framed by swaying palms and 720 feet of shimmering Sarasota Bay frontage, the community feels like a private tropical sanctuary, where beautiful sunrises paint the sky and waterfowl dive gracefully for fish along the shoreline. Boaters will appreciate the ideal marina location, offering a quick, scenic ride to the Gulf of Mexico. The marina is fully equipped with electrical service, fresh water and a fish-cleaning station, while the seawall provides front-row views of dolphins and playful manatees. A kayak launch adds even more ways to enjoy life on the water. Inside, this spacious two-bedroom, two-bath residence spans 1,300-plus square feet of light-filled living with captivating views of Bay Harbour Marina and Sarasota Bay. Both bedrooms feature walk-in closets, and the kitchen blends style and function with wood cabinetry with glass fronts, stainless-steel appliances, solid-surface countertops and tile flooring throughout. The generous primary suite offers an en-suite bath and a peaceful vantage point overlooking the turquoise bay waters. Offered furnished, the home includes an in-unit washer and dryer, covered assigned parking, ample guest parking and elevator access. Bay Harbour’s amenities elevate the experience with a heated pool, grilling area and first-come boat slips accommodating vessels up to 42 feet. Owners may have one pet. Positioned in south Longboat Key, you’re just 15 minutes from downtown Sarasota, home to upscale shopping, acclaimed dining, galleries, theater, opera, ballet and vibrant arts scene. And for everyday indulgence, you can visit or bike to St. Armands Circle, a beloved destination of boutiques, cafés and coastal charm.
Listing Agent: Kathleen Wingate (813-731-3332)
500 HALYARD LN, LONGBOAT KEY, FL 34228
$1,995,000129 Days on yellowkey MLS ID: A4683571
0 Days Off yellowkey (back on 6/13/2026)
REDUCED by $154,000 (7.2%) on 05/31/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2311 Built: 1967Monthly Fee: $21 Tax: $23,973 (2025)Community: Country Club ShoresSpa: YesSingle Family
Taxes:$23,973
Remarks: Huge Price Reduction. Flexible Terms. Best-Priced Waterfront in Country Club Shores. Gorgeous Views and Updated. New Roof, New Seawall, New Impact Windows & Doors - 1/2 Acre Elevated Waterfront Lot - Enjoy the Longboat Key Island Lifestyle. In a prime South Longboat Key location, this beautifully updated waterfront home offers a blend of privacy, comfort and exceptional boating access. Set on a large, elevated, tropically landscaped lot, the property captures wide water canal views stretching toward Sarasota Bay, with stunning water vistas visible from nearly every room. Designed with an inviting open floor plan, the residence features three bedrooms and two baths, thoughtfully arranged for everyday living and effortless entertaining. The private primary suite is a retreat, complete with stunning water views, generous walk-in closet, an en-suite bath and a unique outdoor shower for enjoying the coastal lifestyle. A separate guest suite provides privacy for visitors, while the cozy third bedroom offers flexibility for additional guests, an office or hobby space. In addition, the open floor plan seamlessly blends dining and living areas to capture stunning water views throughout. Recent upgrades bring beauty and peace of mind, including a new metal roof, new hurricane-impact windows and doors, a new hurricane-rated screened pool cage, new air conditioner, and new seawall and composite dock. The outdoor living spaces are equally impressive, highlighted by a screened-in pool area with spa and an additional screened room off the pool, ideal for relaxing or entertaining while enjoying tranquil water views. Boating enthusiasts will appreciate the new seawall and private composite dock, with easy access to Sarasota Bay and the Gulf of Mexico and no fixed bridges along the way. The large paver driveway adds curb appeal, while the dedicated laundry room includes front-load washer and dryer for convenience. Completing the coastal lifestyle, the property includes deeded beach access, allowing you to enjoy sunrise views over the bay and sunset walks along the Gulf. Seller willing to work with a qualified buyer on terms. This exceptional home offers the best of Longboat Key living, privacy, upgrades, water views, deeded beach and outstanding boating access. Schedule Your Private Showing.
Listing Agent: Michael Seamon (941-586-1802)
848 EVERGREEN WAY, LONGBOAT KEY, FL 34228
$599,90018 Days on yellowkey MLS ID: A4698229
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1440 Built: 1991 Tax: $3,533 (2025)Community: Cedars East Sec 3Townhouse
Taxes:$3,533
Remarks: 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 (941-867-6199)
Listing Agent: Rex Glasson (941-587-6135)
4420 EXETER DR #303, LONGBOAT KEY, FL 34228
$575,000172 Days on yellowkey MLS ID: TB8455704
REDUCED by $24,000 (4.0%) on 07/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1970Monthly Fee: $1,412 Tax: $3,678 (2025)Community: Longboat HarbourSpa: NoCondo
Taxes:$3,678
Remarks: Enjoy tranquil, unobstructed Sarasota Bay views from this top-floor, two-bedroom, two-bath partially furnished residence in the desirable Longboat Harbour community. Fresh paint and updated lighting in some areas of the home enhance the bright, inviting interior, while comfortable living spaces offer peaceful water views from most rooms. The kitchen features stainless steel appliances, the hall bath has been refreshed with timeless finishes, and impact windows plus in-unit washer and dryer hookup add everyday convenience. Longboat Harbour offers resort-style amenities including multiple heated pools, fitness center with sauna, tennis, pickleball, shuffleboard, fishing pier, boating docks up to 34 feet, bike and kayak storage, on-site management, and deeded beach access just across the street with gated parking and facilities. Perfectly located mid-key for relaxed island living.
Listing is courtesy of: SMITH & ASSOCIATES REAL ESTATE (727-342-3800)
Listing Agent: Jerry Gemmecke (317-445-2434)
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