Location: Longboat Key , 34228
Do Not Show Listings
5005 GULF OF MEXICO DR #5, LONGBOAT KEY, FL 34228
$3,995,000249 Days on yellowkey MLS ID: A4661988
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4044 Built: 2018Monthly Fee: $766 Tax: $49,274 (2024)Community: BonaireSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$49,274
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: The Quintessence of Coastal Living: A British West Indies Masterpiece on Longboat Key - Where Architecture Meets Paradise. Offered turn-key, this exquisite 4,000+ sq. ft., 4-bedroom, 4.5-bath residence in Longboat Key’s prestigious Bonaire subdivision is a rare union of refined British West Indies architecture and the serene beauty of Florida’s Gulf Coast. Every inch of this home has been thoughtfully crafted to evoke a sense of effortless luxury—where sun-kissed days and gentle Gulf breezes blur the line between indoors and out. From the moment you step through the grand entrance, you’re embraced by light, texture, and tranquility. Creamy finishes, warm woods, and bespoke millwork elevate every space, while expansive windows and French doors invite in the turquoise glow of the Gulf and the soothing rhythm of coastal life. Main Level Elegance - The heart of the home features an open-concept chef’s kitchen with top-of-the-line appliances: a Wolf 6-burner gas range with custom vent hood, dual Asko dishwashers, Sub-Zero refrigerator/freezer, Wolf convection/microwave, and a 50-bottle wine captain. Quartz countertops, artisan pendant lighting, and a massive island with farmhouse sink make this space as beautiful as it is functional. The adjoining dining and great room flow effortlessly to an expansive balcony - perfect for indoor-outdoor entertaining. The main-floor Primary Suite offers tray ceilings, shiplap accents, dual walk-in closets, and a spa-inspired bath with soaking tub, double-entry stone shower, and sparkling stone vanities. Two additional ensuite guest rooms on this level echo the home’s airy, coastal elegance, and exceptional quality. Upper-Level Retreat - Ascend to a private owner’s sanctuary with dual custom closets and a lavish bath adorned with blue calcite counters, glass mosaic tile, and a freestanding tub. This level includes a substantial private balcony with access to the upper-level viewing balcony. The Observation Deck - Crowning the home is the ultimate vantage point—a “Sunset Terrace ” with panoramic Gulf and Sarasota Bay views. It’s here you’ll end each day watching sunsets paint the horizon in unforgettable color. Resort-Style Outdoor Living - The pool retreat is an absolute showstopper - pocketing sliding doors reveal coral stone terraces, a resort-style pool with sun shelf and tiled cocktail table, a 10-person spa, and a fully equipped outdoor kitchen with seating for eight. The entire area is lined with an automatic insect elimination system to ensure you can enjoy the outdoors all year long. Optical lighting enhances the overflowing water features which seem to dance in the glow of firelight, creating the perfect setting for stargazing or nightcaps. The community provides private beach access and is close to world-class golf, tennis, fine dining, and the largest deep-water marina on the Gulf coast. This is more than a home - it’s a sanctuary, a work of art, and a lifestyle. Delivered exactly as you see it, fully furnished and ready to enjoy, this British West Indies masterpiece awaits the one discerning buyer ready to claim the very best of Longboat Key coastal living.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Kathy Callahan (941-900-8088)
7030 POINSETTIA AVE, LONGBOAT KEY, FL 34228
$1,099,00032 Days on yellowkey MLS ID: A4686787
REDUCED by $100,000 (8.3%) on 04/15/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1402 Built: 1934 Tax: $6,672 (2025)Community: Longbeach On Longboat KeySpa: YesSingle Family
Taxes:$6,672
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2025
Middle School: Martha B. King Middle
Remarks: MOTIVATED SELLERS! Enjoy as an investment opportunity or your own private retreat in the highly desirable Village neighborhood on the north end of Longboat Key, with no HOA fees and convenient Gulf Beach and Sarasota Bay access. Set on an oversized lot, the property includes a main residence and a separate guest cottage connected by an inviting breezeway, creating excellent flexibility for seasonal use or extended stays. Each space offers privacy and comfort, enhancing overall livability and guest experience. This turnkey furnished property has been thoughtfully restored to preserve its historic charm. Key updates include a metal roof, impact windows, new cabinetry, and updated appliances, providing both character and peace of mind. The main home welcomes you with an enclosed front porch and a warm, inviting living area complete with a wood-burning fireplace, pine wood flooring, and shiplap accents. The updated kitchen features striking countertops and extended workspace perfect for entertaining, with direct access to a private courtyard deck shaded by a majestic tree. The primary bedroom offers vaulted ceilings and a large walk-in closet. The primary bathroom is also tastefully updated. The guest cottage includes its own entrance, ensuite bathroom, private patio, and full kitchenette, making it well suited for guest accommodations or extended stays. Outdoor amenities further enhance the property’s appeal. A covered entertaining area overlooks the pool and spa within a screened lanai, complemented by a well-appointed covered outdoor kitchen. The spacious paver patio and lush tropical landscaping create a private resort-style setting that appeals to long-term or seasonal residents and guests alike. The oversized lot provides ample parking, including space for a boat or golf cart, an added benefit in this beach to bay community. With convenient access to a boat ramp, nearby beaches, waterfront dining and local shops, this charming neighborhood enjoys strong demand. Turnkey and ready to enjoy or generate annual or seasonal rental income, the seller is open to offers.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Cindy Fischer (941-465-1124)
677 LANDS END DR, LONGBOAT KEY, FL 34228
$2,790,00064 Days on yellowkey MLS ID: A4682565
REDUCED by $60,000 (2.1%) on 04/18/2026
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: In a rich tropical waterfront setting on Longboat Key, this unique retreat lives like a modern treehouse while evoking a sense of peace, family and comfortable, easy island living. Tucked within the island’s native landscape along a natural bayou off Sarasota Bay, the property offers a rare opportunity to experience serene waterfront living surrounded by nature, with the Gulf’s azure waters and pristine beach access just moments away. Enjoy your private backyard dock and kayak launch or secure your boat on one of the deepwater slips on the open bay. Excellent fishing and bird watching await right outside your door in this remarkable natural habitat. The spacious home is anchored by a stunning great room with vaulted cedar ceilings and exposed beams. The home features a 40-by-9-foot sunroom with bar area and handcrafted art shelves, a dedicated library, an inviting family room and a separate private office with extensive built-in cabinetry, providing warmth and functionality. Extensive decking spans the front entry and wraps around an inner atrium courtyard for alfresco dining. An elevated cabana-style shaded area invites relaxation in sun and shade. The kitchen with center island is positioned for hosting memorable gatherings. The primary suite offers a full wall of windows overlooking the tranquil bayou, two walk-in closets and an additional wall of custom storage. The split floor plan provides a separate wing for guests, featuring two additional bedrooms and baths for convenient hosting. Each guest room offers private access to the outdoor decks and views of the tropical center atrium. Two garages accommodate up to four vehicles, boats, golf carts or paddleboards. Many of the furnishings are included. In Land’s End, an intimate gated community of just 12 residences, owners enjoy maintenance-free landscaping, a heated pool, tennis and pickleball courts, and convenient deepwater boat slips, all artfully tucked among the trees for privacy. From here, it is a short visit or golf cart ride to the captivating sandy Gulf beach or local favorites, including Shore Longboat Key, Mar Vista Dockside Restaurant and Whitney’s. The adjacent plaza also offers multiple popular waterfront cafes, boutique shops, Ventura’s restaurant, and 24/7 gym or Pilates studio. Enjoy mesmerizing sunsets on the Gulf or sunrises on the bay from this waterside community. This is a rare offering in today’s marketplace, capturing the allure of Old Florida living in one of the island’s treasured enclaves.
5655 GULF OF MEXICO DR #A107, LONGBOAT KEY, FL 34228
$799,00011 Days on yellowkey MLS ID: A4687549
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1274 Built: 1975Monthly Fee: $1,164 Tax: $3,185 (2025)Community: Cedars West Of Longboat IncCondo
Taxes:$3,185
Remarks: Experience the best of Gulf-front living and gorgeous views in this move-in-ready, two-bedroom, two-bath waterfront condominium, perfectly positioned in an elevated community just steps from the beach. This home is in impeccable condition and is designed for relaxation, with a seamless blend of comfort, style and convenience. It's being sold turnkey with lovely furnishings. The kitchen features new Samsung stainless steel appliances, plenty of counter space, and a comfortable sitting area. An open floor plan with a large living room, remote-controlled sunshades and three-panel impact sliding glass doors opens to an inviting screened lanai with a tropical ceiling fan, blurring the lines between indoor and outdoor living. There are ceiling fans in every room. The primary suite offers a large bath with a separate water closet and a huge walk-in closet. There are also impact sliders leading out to the lanai with a view of the Gulf. The guest suite is spacious with lots of closet space. The laundry is neatly tucked away and features Bosch machines. If you love the beach and enjoy stunning sunsets, Cedars West is really the perfect place to live. This location is walking distance to our local restaurants (Lo-Key, Harry's and Hugos), convenience shopping and all the amenities you’ll need to enjoy life here on Longboat Key. This community has tennis, a heated pool, BBQ area, bike racks, and kayak storage. Cedars East, just across the street, offers tennis membership with a world-class facility. This financially sound community offers peace of mind with a new roof and no assessments planned. With a liberal rental policy allowing up to 26 rentals/year, this property presents an exceptional investment opportunity while still offering the flexibility to enjoy your own beach getaway. There is a locking owner's closet in the unit. You have to see this home to really appreciate how special it is.
Listing Agent: Judy Mitchell (941-275-6838)
3610 BAYOU CIR, LONGBOAT KEY, FL 34228
$2,400,00021 Days on yellowkey MLS ID: A4688141
Bed: 3 Bath: 3.5 Gar: 4 Liv Area Sq Ft: 3192 Built: 1993Monthly Fee: $104 Tax: $18,202 (2025)Community: Bay IslesSpa: YesSingle Family
Taxes:$18,202
Remarks: Welcome to The Bayou section of beautiful Bay Isles. Tucked away from the hustle and bustle of daily life, this double-gated community, a collection of 126 homes, is the perfect place to be on Longboat Key. The pavered front circular drive delivers you to the elevated double-door entrance. Step inside and prepare to be delighted by the neutral palate throughout and an abundance of natural light. Living is easy in this updated three-bedroom home which includes high ceilings and many tasteful architectural details. Three full baths and one-half bath, a dedicated office adjacent to the primary bedroom, a large formal dining room, separate breakfast room, classy cabinet-filled kitchen with new granite counters and a 9 ft island (seats 6). The kitchen is open to a spacious great room featuring vaulted ceilings, recessed lighting, built-in surround sound and a natural gas fireplace. This step-saving layout includes a main level laundry room as well. The primary bedroom has a new primary bath with a dual control sizeable shower, a walk-in custom closet, and direct access to the heated pool and spa just outside. Every bedroom has an en-suite full bath including the one that has direct pool deck access. Three sets of sliding glass doors open to the outdoor kitchen, pool and spa, all raised to be on the same living level. This main feature, having all living space elevated well above sea level is a bonus. An extremely large non-conforming space on ground level is ideal for multiple cars and/or boat storage, plus an air-conditioned space for a workshop or weight room if desired. There is a brand- new Trane A/C system (2026) as well as a new gas pool heater (2025) With too many fine features to list, this home is a must see. Ownership includes membership into the Bay Isles Beach Club, your private spot on the white sands of the Gulf of Mexico. Also, Longboat Key Golf and Tennis Club membership is available separately. Take a short drive to shopping and dining at the famous St Armands Circle and Downtown Sarasota. Magnificent!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Mike Prisco (941-812-1291)
510 BOWSPRIT LN, LONGBOAT KEY, FL 34228
$4,400,00025 Days on yellowkey MLS ID: A4687207
REDUCED by $200,000 (4.3%) on 04/13/2026
Bed: 5 Bath: 6.5 Gar: 2 Liv Area Sq Ft: 4389 Built: 2013Monthly Fee: $21 Tax: $35,060 (2025)Community: Country Club ShoresSpa: YesSingle Family
Taxes:$35,060
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: One or more photo(s) has been virtually staged. Welcome to this renovated waterfront luxury retreat in the highly sought-after Country Club Shores on Longboat Key. From the moment you arrive to this 5 bedroom 6.5 bathroom almost 4,400 sqft home sitting on nearly ¼ acre, the home’s striking curb appeal, tropical landscaping, and circular paver driveway set the tone for what awaits inside. Perfectly positioned on a deepwater canal with quick access to Sarasota Bay and the Gulf, this exceptional residence offers the ultimate Florida lifestyle with a private dock, 28,000-pound boat lift, and room for a large vessel currently docking a 38 ft boat. Stepping through the front entry, you’re welcomed into a stunning open-concept interior where designer finishes and natural light come together beautifully. The expansive main living area offers soaring coffered ceilings and an impressive floor-to-ceiling marble feature wall complete with an electric fireplace and custom wine display. Large sliding glass doors open wide to seamlessly blend indoor/outdoor living, allowing the waterfront views to become part of everyday living. The gourmet kitchen features top-of-the-line Thermador appliances, custom cabinetry, a wine refrigerator, quartz countertops, and an oversized island with generous seating. The kitchen flows effortlessly into the family room, while the adjacent dining area and breakfast nook offer additional space to gather, all framed by peaceful water views. Privately tucked away on the main floor, the owner’s suite serves as a true retreat. This serene space with plantation shutters offers a luxurious spa-like bathroom complete with dual vanities, quartz countertops, a soaking tub, a walk-in glass shower with a waterfall showerhead, elegant tile finishes, and a Toto Neorest toilet. Upstairs, you’ll find four generously sized bedrooms, each with its own ensuite bathroom and spacious closet, offering comfort and privacy for family or guests alike. One upstairs suite functions beautifully as a secondary primary suite with tray ceilings, dual vanities, and a large walk-in shower with dual showerheads. An upstairs media room adds flexibility and is the perfect place for movie nights, game days, or relaxed entertaining, while the upper-level terrace provides another place to unwind and take in the surrounding waterfront views. An elevator services the garage, first floor, and second floor, adding everyday ease and convenience. Outside, the backyard was designed to feel like your own private resort. The heated saltwater pool and spa are surrounded by travertine tile, tropical landscaping and spacious lounging areas, all overlooking the water for a tranquil setting. A full pool bath adds functionality for seamless indoor-outdoor living. Whether you're spending the afternoon poolside, entertaining under the sun, or heading out for a sunset cruise from your private dock, this home delivers the kind of waterfront lifestyle buyers dream about. Located in the coveted Country Club Shores community, this exceptional property also offers deeded beach access to the powder-soft Gulf beaches just moments away. Enjoy being only minutes from the world-class golf, tennis, dining, and marina amenities of Longboat Key Club, along with the upscale shopping and restaurants of St. Armands Circle, the arts and culture of downtown Sarasota, and the convenience of SRQ International Airport. This is more than just a home, it’s a luxury coastal lifestyle in one of the area’s most desirable waterfront communities.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Kaisen Mitchell (941-726-7657)
6750 GULF OF MEXICO DR #163, LONGBOAT KEY, FL 34228
$500,00050 Days on yellowkey MLS ID: A4683547
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1449 Built: 1970 Tax: $4,337 (2024)Community: Whitney BeachCondo
Taxes:$4,337
Remarks: In the sought-after Whitney Beach community on Longboat Key’s peaceful north end, this beautifully renovated two-bedroom, two-bath end unit residence offers 1,449 square feet of coastal contemporary living with tranquil water views over protected Bishop’s Bayou. Enjoy serenity of a coastal inlet sheltered from constant boat traffic of the Intracoastal Waterway, where dolphins and manatees glide past your rear Florida room, a front-row seat to nature. The versatile floor plan includes spacious bedrooms with en-suite baths (showers only), a bright 9-by-14-foot flex space with abundant windows where the washer and dryer connection is located, plus an additional 8-by-3-foot storage area. The kitchen features quartz countertops, stainless steel GE appliances and a water view that enhances everyday living. Tasteful coastal selections, a light palette and additional end unit windows create an airy, open feel throughout, complemented by storm-resistant windows for added peace of mind. Whitney Beach offers resort-style amenities including two pools, tennis court, barbecue stations, kayak storage and launch, lush recreational paths and deeded private beach access directly across the street to the turquoise Gulf waters. Boat slips are available when offered, with annual dock fees of $600 for slips up to 33 feet and $480 for slips up to 24 feet. Sublets are available. Two pets are welcome with no weight restrictions. Rentals are permitted with a one-month minimum. An exceptional opportunity to enjoy bay-to-beach living in one of Longboat Key’s charming waterfront communities.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Karen Whitaker (941-724-6969)
550 DE NARVAEZ DR, LONGBOAT KEY, FL 34228
$1,295,00056 Days on yellowkey MLS ID: A4683082
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1758 Built: 1977 Tax: $6,151 (2025)Community: Sleepy Lagoon ParkSingle Family
Taxes:$6,151
Remarks: One or more photo(s) has been virtually staged. Welcome to 550 De Narvaez Drive, a meticulously maintained WATERFRONT residence set on an ELEVATED 10,000 sq. ft. lot in the highly desirable Sleepy Lagoon neighborhood on the NORTH END of Longboat Key. This solid concrete block home has experienced NO FLOODING & NO STORM DAMAGE, offering exceptional peace of mind. Spanning 1,758 sq. ft., the light-filled interior features 3 SPACIOUS BEDROOMS and 2 beautifully RENOVATED BATHS. Generous room sizes, abundant natural light, and an inviting floor plan create a true sense of warmth throughout the home. The UPDATED KITCHEN and baths showcase contemporary finishes while maintaining comfort and functionality. Enjoy peaceful CANAL VIEWS with direct access to Sarasota Bay—perfect for boating enthusiasts and embracing the ultimate Florida waterfront lifestyle. NEW DOUBLE PANE IMPACT-RESISTANT WINDOWS and sliding glass doors provide enhanced protection and energy efficiency. Additional upgrades include NEWLY LINED PLUMBING PIPES and UPGRADED ATTIC INSULATION for lasting durability and comfort. Offered FULLY FURNISHED, all furnishings convey with the sale—making this a true TURNKEY opportunity. Simply bring your suitcase and start enjoying coastal living immediately. The expansive elevated lot offers ample space for outdoor entertaining, gardening, or FUTURE EXPANSION POTENTIAL. Ideally located near world-renown Gulf beaches with DEEDED BEACH ACCESS, exclusive dining, boutique shopping, and recreational amenities, this exceptional property is well-suited as a primary residence, seasonal retreat, or investment opportunity. Schedule your private showing today and experience refined, worry-free waterfront living at its finest.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Dean Hinterstoisser (941-726-0314)
552 JUAN ANASCO DRIVE, LONGBOAT KEY, FL 34228
$999,99975 Days on yellowkey MLS ID: A4680786
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
Remarks: 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)
2039 GULF OF MEXICO DR #G3-203, LONGBOAT KEY, FL 34228
$499,99918 Days on yellowkey MLS ID: A4688685
REDUCED by $39,001 (7.2%) on 04/15/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1214 Built: 1974Monthly Fee: $1,170 Tax: $5,576 (2025)Community: Seaplace ISpa: YesCondo
Taxes:$5,576
Remarks: Experience the Best of Coastal Living at Seaplace on Longboat Key! Welcome to this beautifully maintained 2-bedroom, 2.5-bath residence offering a perfect blend of comfort, style, and relaxed island living. This spacious two-level layout features an inviting open-concept living and dining area with neutral coastal tones, tile flooring throughout the main level, and seamless access to a private lanai—ideal for enjoying tranquil views and Gulf breezes. The updated kitchen is designed for both functionality and style, showcasing granite countertops, white cabinetry, stainless steel appliances, and a convenient breakfast bar, perfect for casual dining or entertaining. Upstairs, you’ll find two generously sized bedrooms, each offering privacy and comfort. The primary suite serves as a relaxing retreat, while the guest bedroom is ideal for family or visitors. The additional half bath on the main level adds convenience for guests. This residence is offered in move-in ready condition and reflects pride of ownership throughout. Residents of Seaplace enjoy approximately ½ mile of pristine Gulf beach frontage and an exceptional array of amenities across 42 beautifully landscaped acres. Highlights include two heated swimming pools and spas, Har-Tru tennis courts, scenic walking trails, a fitness center, and a clubhouse with kitchen, library, and sauna. Additional features include playground areas, grilling stations, on-site management, and a 24-hour staffed gatehouse for security. Whether you're searching for a primary residence, vacation getaway, or investment opportunity, this home offers the ultimate Longboat Key lifestyle in one of the island’s most sought-after communities. Schedule your private showing today!
Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
Listing Agent: Michael Renick Pllc (941-400-8735)
1571 HARBOR CAY LN, LONGBOAT KEY, FL 34228
$4,750,000204 Days on yellowkey MLS ID: A4666688
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4209 Built: 1987 Tax: $16,980 (2024)Community: Bay IslesSingle Family
Taxes:$16,980
Remarks: Experience the ultimate in luxury coastal living in this 4,209-square-foot stunning waterfront home, perfectly situated in the highly sought-after, gated Bay Isles Harbor Section—an exclusive boating community with only 67 custom residences on south Longboat Key. Designed for elegance and comfort, this timeless 4-bedroom, 3.5-bath estate welcomes you with a dramatic open main living area featuring soaring 23-foot ceilings filled with natural light, rich oak flooring, custom lighting and a gas/wood-burning fireplace. Expansive walls provide the perfect showcase for fine artwork, while the spacious living and dining areas flow seamlessly into a warm family room and a chef’s dream kitchen. The gourmet kitchen is equipped with custom mahogany cabinetry, premium stainless-steel appliances including an induction cooktop, a large island topped with quartzite countertops, and a bright breakfast area overlooking the pool and waterway. Sliding glass doors lead to your private outdoor oasis—a massive 28-foot saltwater pool with solar heating and a partially covered patio with heat-resistant coral stone tile. The luxurious master suite offers two walk-in closets, a sitting area or office, and a spa-inspired bathroom with translucent onyx walls and flooring, a soaking tub, and an oversized shower. Additional features include a large laundry and craft room, an oversized two-car garage with workbench, hurricane-impact windows and doors, reinforced garage doors, and a brand-new concrete tile roof. A beautifully landscaped circular drive welcomes guests, while the deep-water bayou behind the home provides direct access to Sarasota Bay—ideal for boating enthusiasts. Residents of Bay Isles enjoy 24-hour gated security, membership to the Bay Isles Beach Club, and close proximity to the Longboat Key Club, St. Armands Circle, world-class dining, shopping, and the brand-new five -star St. Regis Longboat Key Resort. This exceptional property offers the best of luxury, privacy, and the coveted waterfront lifestyle on Florida’s Gulf Coast.
Listing Agent: Julie Klick (941-780-6001)
578 - 580 COMPANION WAY, LONGBOAT KEY, FL 34228
$999,00069 Days on yellowkey MLS ID: A4682264
REDUCED by $1,000 (0.1%) on 04/19/2026
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 1792 Built: 1963 Tax: $11,672 (2025)Community: Longboat KeySpa: NoApartment
Taxes:$11,672
Remarks: Stunning curb appeal duplex located in the highly desirable Longboat Key featuring two separate addresses, 578 Companion Way and 580 Companion Way. This bright and welcoming coastal retreat offers an elegant and comfortable living environment where refreshing sea air and natural sunlight fill the interior through expansive windows. The property features two separate units including one 2 bedroom 2 bathroom unit and one 2 bedroom 1 bathroom unit. Offered fully furnished and showcasing high quality updates throughout, the property includes a new roof, new AC systems, new water heaters, and all new appliances completed in 2025, delivering modern luxury and peace of mind. Residents may enjoy access to Cedars East resort style amenities including pool, fitness center, and tennis courts with a small optional membership fee. Ideally positioned just steps from the pristine, wide, and uncrowded Gulf beaches, this property provides the ultimate Longboat Key lifestyle. Conveniently located near world class dining and shopping at St Armands Circle, vibrant downtown Sarasota, championship golf courses, marinas, cultural attractions, and everything Sarasota has to offer. Vacation rentals are permitted, creating an outstanding opportunity for investors, seasonal residents, or families seeking to live in one unit while generating additional rental income from the second unit.
Listing is courtesy of: NEXTHOME EXCELLENCE (941-893-4505)
Listing Agent: Linh Pham (941-900-6789)
578 COMPANION WAY, LONGBOAT KEY, FL 34228
$999,00069 Days on yellowkey MLS ID: A4682186
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1792 Built: 1963 Tax: $11,672 (2025)Community: Longboat KeySpa: NoSingle Family
2425 GULF OF MEXICO DR #14B, LONGBOAT KEY, FL 34228
$1,690,000323 Days on yellowkey MLS ID: A4654664
REDUCED by $60,000 (3.4%) on 04/18/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1470 Built: 1973 Tax: $18,495 (2024)Community: Sea Gate ClubSpa: YesCondo
Taxes:$18,495
Remarks: BREATHTAKING WATER VIEWS FROM EVERY ROOM! Enjoy nightly sunsets from your private balcony in this beautifully updated 14th-floor condominium. This highly sought-after two-bedroom, two-bath split floorplan offers the perfect blend of privacy and open living. Each bedroom is positioned on opposite sides of the unit, creating an ideal layout for guests or remote work. Recent upgrades include Hurricane Impact Windows (2021), new flooring in both bedrooms (2021), updated bathrooms, fresh paint (2021), and an A/C system replaced in 2015. The convenience of an in-unit washer and dryer, a dedicated parking space, and ample guest parking add to the comfort of this coastal retreat. The beach and heated pool are just steps from your building, creating a true resort-style experience. Enjoy premium amenities such as a tennis court, air-conditioned bike room, kayak/paddleboard storage, clubhouse with kitchen, library/meeting space, and a fully equipped fitness center. Located within walking distance to Publix, CVS, places of worship, banks, the public library, and Town Hall. Just minutes to St. Armands Circle, where you'll find world-class dining and shopping. Immerse yourself in Sarasota’s rich cultural scene with easy access to the Sarasota Opera, Ballet, Ringling Museum, Selby Gardens, and numerous art galleries and theaters. This is your chance to live the Gulf Coast lifestyle—don’t miss it!
Listing is courtesy of: ANMARK REALTY LLC (941-363-1043)
Listing Agent: Andrey Markov (941-363-1043)
612 JUAN ANASCO DR, LONGBOAT KEY, FL 34228
$22,500,000412 Days on yellowkey MLS ID: A4643123
Bed: 6 Bath: 8.0 Gar: 9 Liv Area Sq Ft: 9243 Built: 2024 Tax: $32,107 (2024)Community: Sleepy Lagoon ParkSpa: YesSingle Family
Taxes:$32,107
Remarks: Welcome to your private, gated estate on Longboat Key, where coastal luxury meets effortless sophistication. Boasting over 730 feet of water frontage, this stunning property offers panoramic views of Whitney Bayou and Harris Canal and provides the ultimate waterfront lifestyle. With 9,243 square feet of air-conditioned living space and a total of 21,562 square feet on over an acre of pristine land, this estate is a masterpiece of design and craftsmanship. Designed in the timeless British West Indies style, this home showcases vaulted ceilings, extensive trim detailing, white oak floors throughout, and two fireplaces, creating an ambiance of elegance and warmth. The expansive covered patios and porches invite you to embrace the serenity of waterfront living, while the heated pool and an impressive 13' x 13' hot tub serve as the ultimate retreats. A custom outdoor fire pit, two outdoor kitchens, and indoor and outdoor pool tables elevate the entertainment experience. For boating enthusiasts, this estate is unrivaled, featuring four low-profile boat lifts—the largest accommodating vessels up to 30,000 pounds, the second suitable for a vessel up to 20,000 pounds, and the third and fourth lifts each with a 5,000-pound capacity, ideal for jet skis, kayaks, and paddle boards. Located just 10 minutes from the Gulf of Mexico by boat and 5 minutes to Shore and Mar Vista restaurants, this is the perfect haven for life on the water. Inside, the Wolf Sub-Zero appliances provide top-tier performance in a gourmet kitchen built for culinary excellence. A Control4 smart home system offers seamless automation throughout, while HVAC-equipped garages ensure comfort year-round. The multiple garages can accommodate up to 9 cars, and the massive driveway can host 20+ vehicles. The residence boasts six spacious bedrooms, each with an en-suite bathroom, plus an additional full bath and two half baths. Designed for both productivity and leisure, the home features his and hers offices, a media/theater room, a fully equipped gym, sauna, golf simulator, tackle garage, and a workshop. A private guest suite with a separate entrance includes a kitchenette, dining room, living room, bedroom, and bathroom, offering a luxurious retreat for visitors. With two state-of-the-art elevators, expansive landscaping, and a maintenance-free turf yard, this estate blends modern convenience with natural beauty. Ideally located near pristine beaches, world-class shopping, and gourmet dining, this estate is the epitome of waterfront elegance and exclusivity. Experience the pinnacle of coastal living—this is truly paradise found.
Listing Agent: Charles Buky (941-228-6086)
3598 FAIR OAKS LN, LONGBOAT KEY, FL 34228
$2,795,00099 Days on yellowkey MLS ID: A4677923
1 Days Off yellowkey (back on 4/18/2026)
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3417 Built: 1996Monthly Fee: $833 Tax: $15,229 (2025)Community: Queens HarbourSpa: NoSingle Family
Taxes:$15,229
Remarks: Under contract-accepting backup offers. Situated within the gated Queens Harbour enclave of Bay Isles, this thoughtfully updated four-bedroom courtyard residence offers a refined blend of privacy, comfort, and waterfront living on Longboat Key. Designed around a lush central courtyard, the home creates an effortless indoor-outdoor flow anchored by a resurfaced swimming pool and new paver deck—an inviting retreat for everyday living or entertaining. A private cabana suite with its own entrance provides flexibility for guests or extended stays, enhancing the home’s functionality while maintaining separation from the main living areas. Entry begins through custom mahogany and glass double doors, opening to a reimagined open-concept interior with soaring 14-foot ceilings, wide-plank wood flooring, and carefully curated architectural detail throughout. The great room is centered around a travertine-encased electric fireplace and framed by walls of windows and glass sliders that capture tranquil lake views and abundant natural light. This space flows seamlessly into the formal dining area, highlighted by a statement chandelier and tongue-and-groove tray ceiling, and continues into the chef’s kitchen—designed as the heart of the home. The kitchen features a dramatic 14-foot quartz-topped island, custom designer cabinetry by Sarasota Architectural Woodworking, and newer Thermador appliances, including a five-burner gas cooktop, dual built-in ovens, pull-out pantry cabinetry, and a 48-inch stainless sink. Adjacent informal dining and family spaces include aquarium-style glass windows and an oversized wet bar with a full-size wine cooler capable of storing over 100 bottles. The primary suite, located on the main level, offers a peaceful lakefront setting with French-door access to the patio, custom built-in storage, and a walk-in closet. The spa-inspired bath was recently updated with dual quartz-topped walnut vanities, soaking tub, glass-and-stone shower, and private water closet. Also on the first floor are a versatile study overlooking the courtyard and a bonus room with an attached full bath that can serve as an additional bedroom or media space. The second level is dedicated to a private en-suite guest bedroom. Queens Harbour residents enjoy access to a heated Olympic-size pool and spa, along with deeded entry to the private Bay Isles Beach Club. Beyond the gates, Longboat Key’s lifestyle amenities are just minutes away, including the Longboat Key Club’s golf and tennis facilities, marinas, dining, and everyday conveniences. St. Armands Circle and downtown Sarasota’s cultural attractions—shopping, galleries, theaters, and waterfront dining—are easily accessible, completing the appeal of this well-positioned coastal residence.
Listing Agent: Roger Pettingell (941-387-1840)
4485 GULF OF MEXICO DR #402, LONGBOAT KEY, FL 34228
$760,000124 Days on yellowkey MLS ID: A4675789
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1022 Built: 1973Monthly Fee: $1,050 Tax: $4,183 (2024)Community: Arbomar AptsCondo
Taxes:$4,183
Remarks: Experience exceptional beachfront living in this beautiful Gulf-front residence at Arbomar on Longboat Key. Unit 402 is a 2-bedroom, 2-bath condominium offering direct, unobstructed Gulf of Mexico views and immediate beach access, making it the most affordable 2-bedroom, 2-bath opportunity on Longboat Key with true Gulf frontage. The residence features a bright, open layout designed to capture stunning water views and coastal breezes. Significant recent improvements provide exceptional value and peace of mind, including a new roof, new balconies and walkways, updated carports, and new doors and impact-rated windows throughout the community. Inside, the home is move-in ready with a newer AC system and newer appliances, ideal for full-time living, a seasonal retreat, or an income-producing beach getaway. Arbomar offers elevator access, a heated beachfront pool, fitness center, and a welcoming, well-maintained community. All special assessments will be paid in full by the seller at closing, eliminating future capital expense concerns for the buyer. Perfectly positioned on Longboat Key, Arbomar is just minutes from St. Armands Circle, Sarasota’s dining and cultural attractions, and world-class golf—while delivering the rare luxury of direct Gulf views and private beach access at an exceptional value.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Richard Tyson (941-999-1179)
4350 CHATHAM DR #Unit E-208, LONGBOAT KEY, FL 34228
$675,000144 Days on yellowkey MLS ID: A4672221
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1316 Built: 1969 Tax: $6,535 (2025)Community: Longboat HarbourCondo
Taxes:$6,535
Remarks: One or more photo(s) has been virtually staged. NEW PRICE IMPROVEMENT! REDUCED $20,000! NEWLY REMODELED • COASTAL LUXURY RESIDENCE Longboat Harbour • Building E #208 | Corner End Unit • Bay & Harbour Views. CLOSEST BUILDING TO A SHORT WALK ACCROSS THE STREET WITH A PRIVATE DEEDED GULF BEACH ACCESS WITH PAVILION, RESTROOMS AND SHOWERS TOTALLY REMODELED FROM FLOOR TO CEILING second-floor corner residence in the highly sought-after Longboat Harbour Community. This light-filled home captures sweeping views of Sarasota Bay and Longboat Harbour. This spacious two-bedroom, two-bath retreat has been transformed with exceptional attention to detail. Elevated finishes, a soothing coastal palette, and an airy open layout blend modern luxury with effortless livability. Corner units of this caliber are rarely available. From the two bedrooms, you step out to the exceptionally Large Lanai with floor to ceiling sliding glass doors. A SHOWCASE KITCHEN WITH TWO SUNLIT WINDOWS AND WATER VIEWS Elegant, functional, and beautifully appointed: • Frigidaire Professional stainless steel appliances • Gleaming quartz countertops • 9-inch deep sink • Pull-out cabinet shelving • Pantry closet • Designer tile backsplash • Large Eat-In Kitchen with water views & sunsets • Instant hot-water. LUXURIOUS PRIMARY SUITE An elevated retreat professionally designed for comfort and relaxation • Private ensuite bath • Custom California Closet walk-in wardrobe • Built-in desk feature • Remote-controlled luxury solar shades. RESORT-INSPIRED AMENITIES Longboat Harbour offers a lifestyle unmatched on the Gulf Coast: • Designated covered parking spot conveniently located • Personal storage space on the third floor • Private deeded Gulf beach access with pavilion, restrooms & shower • Four sparkling pools • Fitness center & sauna • Tennis & pickleball courts • Billiards room, library & meeting rooms • Picnic areas with grills • Putting green • Fishing pier • Affordable resident-only boat dockage • KAYAK LAUNCH and KAYAK WHICH SELLER WILL BE GIFTING TO THE BUYER. Enjoy effortless waterfront living and endless ways to explore the natural beauty of Longboat Key. PROPERTY ENHANCEMENTS & UPDATES: Thoughtfully improved for comfort, reliability, and peace of mind: • NO HURRICANE DAMAGE OR FLOODING • Bosch Washer & Dryer • Newer AC: 12/5/221 • Newer Hot Water Heater: 3/3/17 • New roofs throughout the community • Electrical and plumbing systems updated. A BEAUTIFULLY RENOVATED INTERIOR THAT CREATES THE ULTIMATE COASTAL LIFESTYLE/ THE MONTHLY HOA FEE INCLUDES HAZARD, HURRICANE AND FLOOD INSURANCE/ RESERVES HAVE BEEN FULLY FUNDED
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Billie Chipain (941-587-8556)
4420 EXETER DR #303, LONGBOAT KEY, FL 34228
$625,00085 Days on yellowkey MLS ID: TB8455704
REDUCED by $24,900 (3.8%) on 04/18/2026
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)
563 SPANISH DR S, LONGBOAT KEY, FL 34228
$615,00063 Days on yellowkey MLS ID: A4682513
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1516 Built: 1971Monthly Fee: $1,340 Tax: $7,899 (2024)Community: Spanish Main Yacht Club CondoVilla
Taxes:$7,899
Remarks: GORGEOUS COMPLETELY REMODELED Villa with Lake Views in Spanish Main Yacht Club!! Welcome to effortless coastal living in this beautifully remodeled 3-bedroom, 2-bath villa located in the highly sought-after Spanish Main Yacht Club. Rarely available, this 1,516 sq ft STANDALONE villa offers a larger footprint than most in the community and includes a true third bedroom with serene LAKE VIEWS. The recent remodel brings a fresh, modern feel, complemented by an open-concept floor plan, elegant tile flooring throughout, and abundant natural light. Enjoy peace of mind with NEW IMPACT WINDOWS AND DOORS, NEW WATER HEATER, a NEWER ROOF (2023)AND NEWER A/C system (March 2024). Spanish Main Yacht Club offers a maintenance-free, pet-friendly community with resort-style amenities, including a large waterfront pool overlooking the marina, a 40-slip deep-water marina with no bridges to Sarasota Bay and the Gulf, and deeded beach access just steps away. Shopping, dining, and the charm of St. Armands Circle are all minutes from your door. While this is an active 55+ community, ownership is open to all ages, with full-time residency beginning at 50. "Florida remains the envy of the country, with many of our markets winning awards for being among the best places to live or retire. Sarasota SRQ Airport's soaring success added 30 flights in 2024 and 2025, significant passenger growth, a new $72M runway and terminal, and ranks No. 1 best resort airport in the country, where passengers can get off a plane and feel like their vacation has begun. It's all about investment. This home in the master-planned community of the Spanish Main Yacht Club could be your destination of choice. Features include a spectacular pool and spa, kayak launch, marina, outdoor grills, and lush tropical landscaping. There is a shell path for walking along to a deeded beach access to enjoy the sand and world-class sunsets. There is also on-site management and maintenance staff making where home and away share the same address. Longboat Key is the only barrier island on the West Coast of Florida to have relocated all overhead utilities underground for improved reliability and aesthetics, and LBK landed on the Forbes Travel Guide's list of Top 12 Destinations for 2025." Furniture Package Available. Schedule your private showing today.
Listing is courtesy of: LPT REALTY LLC (813-359-8990)
Listing Agent: Victoria Campbell (352-446-4758)
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