Location: Longboat Key
Do Not Show Listings
4995 GULF OF MEXICO DR #500, LONGBOAT KEY, FL 34228
$5,895,00098 Days on yellowkey MLS ID: A4677613
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3344 Built: 2007 Tax: $47,519 (2024)Community: PositanoSpa: NoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$47,519
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
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)
5422 SANDHAMN PL, LONGBOAT KEY, FL 34228
$3,499,00036 Days on yellowkey MLS ID: A4686120
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2802 Built: 1993Monthly Fee: $400 Tax: $38,212 (2025)Community: SandhamnSingle Family
Taxes:$38,212
Tax Year: 2025
Remarks: Tranquility abounds as you enter the gates of Sandhamn Place, developed by Peder Wallenberg and named after a quaint fishing village just outside of Stockholm Sweden. A private canopied road winds through this sanctuary of nine custom designed waterfront homes, all enjoying expansive views of Sarasota Bay. Be among the privileged few that can call Sandhamn Place their home on Longboat Key, with no tear downs to pass and no barnacle encrusted seawalls staring back at you and no through traffic to tolerate; just 50 square miles of the beautiful bay with only leisurely kayakers & paddleboarders, frolicking dolphins and meandering manatees passing by. Sandhamn Place has its own tennis court and marina with deeded boat slips and is ideally located near the center of Longboat Key, just a short distance from some the island's finest restaurants, shops and conveniences as well as Durante Park, a 32 acre nature preserve with overhanging mangrove walking trails. The home was designed with Key West in mind and offers a relaxed lifestyle at the end of the cul de sac with its own private observation dock extended out into the bay that can be accessed from the screened lanai and heated pool or from the upstairs deck adjoining the primary ensuite bedroom overlooking Sarasota Bay.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Richard Perlman (941-228-8580)
3040 GRAND BAY BLVD #283, LONGBOAT KEY, FL 34228
$1,799,000176 Days on yellowkey MLS ID: A4669347
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2550 Built: 1996 Tax: $18,262 (2025)Community: Grand Bay 2Spa: NoCondo
Taxes:$18,262
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: Welcome to Grand Bay. Experience the essence of refined coastal living, where breathtaking panoramic water and city views take center stage. Awaken to the sunrise over Sarasota Bay’s skyline with limitless views of the bay and golf course, and unwind with stunning sunsets over the Gulf, an ever-changing display of beauty from every room. Perfectly situated on the 8th floor, this elegant home welcomes you through a private-access, controlled elevator leading to a stunning foyer framed by contemporary glass double doors. The Cayman open floor plan immediately reveals sweeping vistas, while large porcelain tile flooring flows seamlessly through the living areas and onto two outdoor terraces ideal for quiet relaxation. The stunning updated kitchen features two-toned cabinetry, Wolf and Sub-Zero appliances, under-cabinet lighting, quartz countertops, and an inviting breakfast bar. An adjacent eat-in area with floor-to-ceiling sliders opens to a private covered terrace, a perfect setting for entertaining guests and boundless vistas. The primary suite is a lavish retreat, complete with white oak floors, two walk-in closets and a spa-inspired bath showcasing, a soaking tub, glass shower, and dual vanities. The guest suite offers private terrace access for stunning sunset views, complemented by white oak floors and an en-suite bath. Discover versatility with a den/office that doubles as an occasional guest room, providing privacy with elegant pocket doors that separate it from the formal dining room, and a 3rd full bath just steps away. A well thought out conversion has added a built-in office area adding functionality to round out the interior. Residents enjoy various first-rate amenities, including 24-hour guard gates, a clubhouse, two community pools and spas, a large fitness center with saunas, and tennis courts. Stroll the neighborhood’s scenic walking paths or enjoy deeded access to the exclusive gated Bay Isles Beach Club offering locker rooms, barbecues, volleyball nets, covered picnic areas and a sandy white beach. Located behind the Bay Isles secure gates, this secluded neighborhood rests on the rolling greens of the Longboat Key Club’s golf course. Grand Bay residents find it hard to leave this special community. This residence truly captures the best refined Bay and beach lifestyle – sophisticated, exclusive, and ready to be enjoyed.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Stacy Hanan (941-266-0529)
2367 HARBOUR OAKS DR, LONGBOAT KEY, FL 34228
$985,000142 Days on yellowkey MLS ID: A4670055
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2219 Built: 1986Monthly Fee: $1,617 Tax: $11,977 (2024)Community: Harbour Oaks 2Villa
Taxes:$11,977
Remarks: NEW PRICE: Lives like a single family home! This 3 bedroom, 2 1/2 bath villa with over 2,200 sq.ft and an attached 2-car garage offers all the privacy and convenience of a private home and all the convenience of a maintenance free community. Located on #2 hole of the White Egret course on the Harbourside Golf Course in the Longboat Key Country Club. This home is in a secure gated community with only 42 villas in Harbour Circle with a community pool and spa and membership access to the deeded private beach club. This home boasts vaulted ceilings, multiple hurricane skylights, hurricane windows, sliders and front door, private atrium and new roof with trusses in 2025, coming completely furnished. Enjoy your morning coffee and dozens of magnificent sunsets on your large two level lanai. Enjoy a walk to Publix, CVS and several Banks close to your community. Only a short drive to Saint Armand's Circle and downtown Sarasota where you will find numerous options for shopping, dinning, theatres, ballet, opera and galleries.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Sandra Endres (941-735-2527)
1914 HARBOUR LINKS CIR #10, LONGBOAT KEY, FL 34228
$1,495,00020 Days on yellowkey MLS ID: A4686139
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2180 Built: 2001 Tax: $12,540 (2025)Community: Emerald Pointe SouthSpa: NoCondo
Taxes:$12,540
Remarks: Tucked behind the gates of Bay Isles in the Emerald Pointe community, this 3BR/3.5BA residence offers 2,180+/- sq. ft. of thoughtfully designed living space with a layout that blends privacy, flexibility and inviting outdoor living. From the moment you arrive, a paver drive framed by lush landscaping and a striking 2-story façade with barrel tile roof set a warm and welcoming tone. A paver walkway leads to the courtyard entrance that defines the home’s character. This open yet private space is bathed in natural light and features a covered and screened sitting area with an all-season kitchen, creating a unique setting for entertaining or quiet relaxation. Just off the courtyard, a separate casita with its own full bath offers ideal space for a home office, guest suite or creative retreat. Inside, the home feels open and spacious, with large tile flooring, high ceilings and a thoughtful mix of clerestory and transom windows that bring light into every corner. Neutral tones and layered textures add depth without distraction. The living room is both functional and inviting, featuring a fireplace, built-in wine refrigerator, and ice maker that enhance the space for everyday living or hosting. The kitchen has been beautifully updated and connects naturally to the main living areas. It features stone countertops, all-white cabinetry, stainless steel appliances, a tile backsplash and a breakfast bar, along with a dining area highlighted by a striking aquarium window that looks back into the courtyard. The primary suite is located on the main living level in a private wing, offering direct access to the pool and a generous walk-in closet. The bath is well appointed with dual vanities, a freestanding tub, a walk-in shower and refined tilework. Upstairs, a guest bedroom provides comfort and privacy, complete with wood flooring, a walk-in closet, desk space and an en suite bath. At the back of the home, a screened lanai and pool overlook a peaceful lake with fountain, where large-panel screening keeps the view open and unobstructed. Additional features include an in-residence laundry room and a two-car garage with abundant storage. Residents of Emerald Pointe enjoy a maintenance-free lifestyle along with access to the private Bay Isles Beach Club, offering white sand beaches just minutes away. Optional membership to the Longboat Key Club further enhances the lifestyle with championship golf, tennis and pickleball, a private beach club, marina, spa and wellness amenities, multiple dining venues, and an active social calendar.
Listing Agent: Bruce Myer (941-376-5311)
806 BAYPORT WAY #806, LONGBOAT KEY, FL 34228
$949,00023 Days on yellowkey MLS ID: TB8489326
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1392 Built: 1981 Tax: $5,917 (2025)Community: Bayport Bch & Ten Ph ECondo
Taxes:$5,917
Remarks: Welcome to this beautifully appointed ground floor residence that combines modern elegance with functional design. Newly remodeled in 2025, this residence features high-end finishes and modern amenities, making it an ideal retreat for those seeking luxury in a serene environment. Upon entering, you are greeted by a bright and spacious interior filled with natural light, thanks to strategically placed additional windows featured in corner/end units of this community. The subtle elegance of the interior is complemented by sleek flooring that enhances the flow from room to room. The kitchen is a true highlight, featuring quality cabinetry, elegant quartz counters, and modern stainless-steel appliances, which allow a harmonious flow, delivering both functionality and sophistication. The open-concept layout continues through the dining and living areas, combining a blend of textures and stylish finishes to cohesively create an environment of relaxed elegance. An abundance of natural light floods this space through large retractable sliding glass doors, which provide the option of extending the outdoors in. A private outdoor patio showcases a beautiful backdrop of lush tropical landscaping, adding to the property’s overall appeal. The bedrooms within the property are thoughtfully designed, each offering generous space and natural light. The primary suite offers a restful retreat, complete with an ensuite bathroom featuring modern fixtures and thoughtful design, ensuring comfort and privacy. This property will continue to amaze, as beauty extends beyond its walls into an amenity-rich community of 27 acres of picturesque tropical landscaping. This gulf-to-bay community offers an active island lifestyle with 4 Har-Tru tennis courts, a Jr. Olympic sized (heated) pool, private fishing pier, kayak facilities, Bocce court, and amazing nature trails. A distinct advantage and unique selling point of this property is its proximity to a private, deeded beach. This property offers future owners not just exclusive beach access, but a revitalizing retreat amidst the hustle and bustle of life—truly a valuable benefit that amplifies the charm of this residence. Close to local amenities yet precisely positioned to offer privacy and quietude, this property represents an excellent opportunity for discerning buyers. Experience the best of coastal living in this beautiful home, where modern comfort meets natural beauty. Welcome home!
Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA (813-684-9500)
Listing Agent: Antonietta Car (813-684-9500)
3636 FAIR OAKS PL, LONGBOAT KEY, FL 34228
$3,600,00032 Days on yellowkey MLS ID: A4686948
REDUCED by $200,000 (5.3%) on 04/08/2026
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3732 Built: 1990Monthly Fee: $833 Tax: $33,616 (2025)Community: Queens HarbourSpa: YesSingle Family
Taxes:$33,616
Remarks: PCATTO! PAY CLOSE ATTENTION TO THIS ONE! There is so much to take in, so let’s start with some bullet points: DIRECT BAY BIG,BIG,BIG WATER VIEW. PRIVACY. 5BED/4.5BATH HOME. ELEVATOR. ALL NEW- DOCK WITH 16,000 LB. LIFT, ROOF, SKYLIGHTS, GUTTERS, OPERATIONAL WINDOWS, DOORS, SHUTTERS (FOR BAYFRONT FIXED WINDOWS), TRAVERTINE POOL DECK, GUNITE POOL SURFACE, FENCE, LANDSCAPING, EXTERIOR PAINT. The work is done for you! Landscaped with privacy in mind and positioned in the cul-de-sac as the last home on the direct Bay in lovely Queens Harbour. The outward attraction of this home will immediately drive your desire to explore further. And, once you enter thru the double glass entry, the exhilaration will overtake you. Bay views abound thru the wide-spread wall of glass that encompasses the common living areas of dinette, kitchen, living room, primary bedroom and bonus rooms. Sky-high ceilings and coastal flooring add to the wonder of this show-place and the fixtures that have been added define the finest of taste. Primary, 2nd and 3rd bedrooms, three full baths, as well as all common space (kitchen, dining, dinette, living room, family room), complete the first level of this home and upstairs you will find two more bedrooms, a bath, and flex space- ELEVATOR OR STAIRCASE ACCESSIBLE. The inside will amaze, but let’s be real- outside living is what Longboat Key is all about. Savor the sunrise from your private dock and ease into the day, poolside. Hop in the boat to head out for a sunset ride to your favorite waterfront dining spot and wrap up with a cocktail in the spa as you admire the stars and Sarasota lights across the Bay. Feel like the beach? Great!! You can do that too because with this home you are a part of Bay Isles which includes the private Beach Club and also provides an added sense of security with guarded and double-gated entry to your community.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Cindy Schatzle (941-587-7556)
500 HALYARD LN, LONGBOAT KEY, FL 34228
$2,199,00042 Days on yellowkey MLS ID: A4683571
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: Gorgeous Views - Impact Windows & Doors - 1/2 Acre Elevated 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. This exceptional home offers the best of Longboat Key living, privacy, upgrades, water views, deeded beach and outstanding boating access.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Michael Seamon (941-586-1802)
4835 GULF OF MEXICO DR #105, LONGBOAT KEY, FL 34228
$675,00054 Days on yellowkey MLS ID: A4684056
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1393 Built: 1970 Tax: $10,445 (2024)Community: Westchester AptsCondo
Taxes:$10,445
Remarks: Experience direct Gulf-front living in this furnished, first-floor walkout residence at The Westchester on Longboat Key. Enjoy sweeping turquoise water views from nearly every room, with miles of pristine shoreline just beyond your door. This well-appointed, inviting two-bedroom, two-bath condominium features a spacious split floor plan designed for comfort and privacy, along with seamless indoor-outdoor living and immediate access to the pool and beach. The kitchen is equipped with stainless steel appliances, solid surface countertops, and abundant cabinetry and prep space. Both bedrooms offer en suite baths and generous walk-in closets, complemented by additional storage. The primary suite features a private screened lanai overlooking the Gulf, creating a tranquil retreat. A second expansive screened lanai off the great room captures panoramic water views and opens directly to the community pool and beach. An in-unit washer and dryer add everyday convenience. This thoughtfully designed, fully furnished residence is ideal for effortless coastal living, whether as a primary home, vacation getaway, or investment opportunity. The unit includes assigned covered parking and private storage conveniently just outside the entry. Community amenities include lighted tennis and pickleball courts, a basketball court, two heated pools, shuffleboard, outdoor grilling areas with cabanas, kayak and bicycle storage, and private beach gear lockers. A newly renovated clubhouse is coming soon and will feature a full kitchen, lending library and fitness area. Rentals are permitted, offering flexibility for seasonal or year-round use. The Westchester’s mid-key location provides convenient access to Bayfront Park with its dog parks and waterfront views, as well as nearby shopping and daily conveniences, including Publix. Residents are minutes from the Centre Shops and Whitney Plaza, along with more than a dozen popular north-end restaurants, including waterfront favorites such as Shore Restaurant and Mar Vista Dockside Restaurant. Longboat Key also offers a private golf course, a full-service marina, and multiple waterfront parks. Nearby destinations include St. Armands Circle and downtown Sarasota, renowned for its vibrant arts and cultural scene.
Listing Agent: Cindy Fischer (941-465-1124)
1445 GULF OF MEXICO DR #103, LONGBOAT KEY, FL 34228
$924,90057 Days on yellowkey MLS ID: A4683660
REDUCED by $65,000 (6.6%) on 04/12/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1933 Built: 1982 Tax: $10,149 (2025)Community: Players Club IiiCondo
Taxes:$10,149
Remarks: Welcome to Residence #103 at 1445 Gulf of Mexico Drive, located within the prestigious Players Club on Longboat Key. This exceptional 550-foot Gulf-front community offers an unparalleled coastal lifestyle, and this residence presents a rare opportunity—available for the first time in 37 years. Originally the building’s model home, this thoughtfully designed condominium combines timeless elegance with spacious comfort. This beautifully maintained residence features three bedrooms, two and a half baths. The third bedroom/den is complete with twin Murphy beds and built-in storage. The spacious living and dining area opens to a wall of sliding glass doors leading to an expansive 30-foot open-air balcony, where you will enjoy sweeping views of the Gulf of Mexico, overlooking the 70-foot heated saltwater swimming pool, spa, lush tropical landscaping, and breathtaking sunsets. Just steps from the pristine beach, this outdoor retreat invites you to relax, read, listen to the waves, and savor spectacular evening skies. Inside, the home offers a seamless blend of style and functionality. The spacious primary suite features sliding glass doors to the balcony, a generous walk-in closet, and a split en-suite bath with dual vanities, a spa-like soaking tub and shower, and a large window that fills the space with natural light. The second en-suite bedroom, privately positioned off the front hallway, is generously sized, offers abundant natural light, and includes a large walk-in closet—perfect for guests. Additional conveniences include a powder room, in-unit laundry, interior storage, and a private storage closet just outside the front door. The residence also includes assigned under-building parking and access to bike storage. Residents of Players Club enjoy resort-style amenities, including a newly renovated clubhouse with a state-of-the-art fitness center, library, catering kitchen, and inviting indoor and outdoor social spaces. Four Har-Tru tennis courts, pickleball, a putting green, beautifully maintained grounds, a security gate, and on-site management provide both luxury and peace of mind. Ideally situated on the desirable south end of Longboat Key, this community is just minutes from Publix, the renowned St. Regis Longboat Key Resort, the upscale boutiques and fine dining of St. Armands Circle, and the vibrant cultural attractions of downtown Sarasota. This is a rare opportunity to own a distinguished Gulf-front residence in one of Florida’s most sought-after coastal communities—where luxury, location, and lifestyle come together beautifully.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Steve Nursey (941-356-7010)
1918 HARBOURSIDE DR #902, LONGBOAT KEY, FL 34228
$1,299,00068 Days on yellowkey MLS ID: A4680710
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1748 Built: 1982Monthly Fee: $146 Tax: $11,598 (2025)Community: Fairway Bay 1Spa: YesTownhouse
Taxes:$11,598
Remarks: Welcome to a masterfully reimagined two-bedroom, 2.5-bath FURNISHED town home offering breathtaking, full open views of Sarasota Bay and the vibrant city skyline with its OWN PRIVATE BOAT SLIP. Arguably the most exquisite residence in the esteemed Fairway Bay community at Bay Isles on Longboat Key. The property underwent a meticulous down-to-the-studs renovation in 2020 that included filling in the 100 square foot atrium on the second floor, blending high-end craftsmanship with its unparalleled waterfront setting. The interior is a showcase of custom artistry, featuring warm wood ceilings, solid White Oak stairway treads, an elegant custom iron stairway railing, inset cabinets, Sonos sound system and a Lutron smart lighting system for effortless ambiance control. The gourmet kitchen is a chef’s dream, anchored by a custom White Oak island with quartz tops, Fisher Paykel built-in appliances, and charming built-in banquet seating breakfast niche. Sophisticated touches continue throughout, including a custom iron wine rack, grass wallpaper, designer light fixtures and sleek tile flooring in every room. Retreat to the primary suite, where soaring wood ceilings and a custom walk-in closet provide a sanctuary of comfort. The bath is light, bright and features a furniture-quality inset vanity and an enclosed wet room complete with a standalone soaking tub. The other bedroom on the second floor also has an en-suite bath that features furniture-quality vanity and beautiful walk-in shower. The second-floor laundry with full size LG front-loaded machines makes doing laundry a breeze. For ultimate peace of mind, the home features an impact-rated bayfront living room window and rear exterior door, complemented by a Garrison Hammerhead Aluminum Flood Barrier System installed in 2025. This system includes reinforced cement pilings just inside the garage door with easy-to-use slide-in aluminum slats designed to prevent water intrusion. As part of the Bay Isles community, residents enjoy world-class amenities including 24-hour gated security, swimming pools, tennis and pickleball courts, and exclusive access to the private Bay Isles Beach Club. Just minutes from the cultural heart of downtown Sarasota and upscale shopping of St. Armands Circle, this home offers a lifestyle of effortless elegance.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Liz Nason (941-350-2243)
1005 BOGEY LN, LONGBOAT KEY, FL 34228
$3,300,00084 Days on yellowkey MLS ID: A4680006
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3624 Built: 2017Monthly Fee: $21 Tax: $19,847 (2025)Community: Country Club ShoresSpa: YesSingle Family
Taxes:$19,847
Remarks: Nestled along a serene canal just a short ride to beautiful Sarasota Bay, this custom-built John Cannon home offers the perfect blend of luxury, comfort, and coastal living. This two-story, 4-bedroom residence features an open floor plan designed for both relaxation and entertaining. Each bedroom is ensuite, providing privacy and comfort for family and guests alike. Enjoy gathering in the spacious area or entertaining outdoors with a heated pool and spa, a fully equipped outdoor kitchen, and a private dock with a boat lift for effortless access to the water. The home also includes an elevator- ideal for transporting luggage and groceries- and a generous 3- garage with abundant storage. Conveniently located near St. Armands Circle and downtown Sarasota, this property offers easy access to fine dining, shopping , and white-sand beaches, making it a true coastal retreat with every modern amenity.
Listing Agent: Michael Nink, Pa (941-914-2805)
3617 FAIR OAKS PL, LONGBOAT KEY, FL 34228
$2,050,000226 Days on yellowkey MLS ID: A4663935
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2950 Built: 1995Monthly Fee: $746 Tax: $16,463 (2025)Community: Queens HarbourSpa: YesSingle Family
Taxes:$16,463
Remarks: One or more photo(s) has been virtually staged. Situated in the highly sought-after maintenance-free community of Queens Harbour, behind the gates of Bay Isles, this updated lakefront home perfectly captures the ease of Florida living. A 2023 tile roof adds peace of mind, while a smart split floor plan includes three en-suite bedrooms, a half bath, and a versatile den/office that can serve as a fourth bedroom. The interiors feel bright and welcoming with 12–15’ ceilings, neutral tones, and elegant architectural details. New wood-look porcelain tile flooring enhances the living room, dining room, den/office, and first-floor bedrooms, combining durability with style. The kitchen features stainless steel appliances, a center island with second sink, updated hardware, and a breakfast nook with bay window views of the pool and lake. The primary suite enjoys direct lanai access, tranquil water views, and a spa-like bath with dual vanities, soaking tub, and walk-in shower. Outdoors, the screened lanai offers a heated pool and spa with a peaceful lake backdrop, plus a refreshed covered sitting area with a new tongue-and-groove ceiling and accent wall—perfect for relaxing or entertaining year-round. Residents enjoy exclusive access to the Bay Isles Beach Club, with its private beachfront, cabanas, and members-only amenities, along with optional memberships for golf, tennis, and the Harbourside Marina with deepwater slips. This home sustained no hurricane damage or water intrusion. This is Longboat Key living made simple—beautiful, low-maintenance, and ready to enjoy.
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
3710 GULF OF MEXICO DR #F2, LONGBOAT KEY, FL 34228
$475,00046 Days on yellowkey MLS ID: A4681154
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 740 Built: 2026Monthly Fee: $290 Tax: $2,070 (2025)Community: Gulfshore Of Longboat KeyManufactured Home
Taxes:$2,070
Remarks: Island Living at Its Finest – Brand New Home on Longboat Key. Welcome to Gulfshore of Longboat, a highly desirable waterfront co-op community offering private beach access, boat docks, and sweeping views of the Gulf of Mexico and Sarasota Bay. This beautifully built 2-bedroom home combines modern efficiency with relaxed coastal living. An outdoor bathroom with a shower is a wonderful convenience for those enjoying the pool or boating. Step inside to an open, sun-filled floor plan featuring soaring ceilings with tray accents in both the living room and the primary bedroom, creating a bright, spacious atmosphere throughout. The kitchen is designed for everyday comfort and entertaining, complete with a center island, hardwood shaker cabinetry with soft-close doors and drawers, and a full stainless appliance package including refrigerator with ice and water, range, dishwasher, microwave, and garbage disposal. Built to current HUD hurricane standards and Energy Star certified, the home offers peace of mind with 2x6 construction, upgraded insulation, and low-E vinyl windows for year-round comfort and efficiency. Enjoy mornings at the private beach, afternoons at the heated pool, and evenings watching sunsets over the water. The community clubhouse hosts regular activities, making it easy to relax and connect with neighbors in a friendly coastal setting. Whether you’re looking for a winter retreat or full-time residence, this move-in-ready island home delivers comfort, security, and the lifestyle Longboat Key is known for. No pets (except for service animals or emotional support animals with appropriate paperwork) or Rentals permitted. Schedule your private showing today and start living the Gulf Coast dream.
Listing is courtesy of: WAGNER REALTY (941-751-0670)
Listing Agent: Marsha Winegarden (248-563-2820)
4340 FALMOUTH DR #D104, LONGBOAT KEY, FL 34228
$530,000106 Days on yellowkey MLS ID: A4676925
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1072 Built: 1969 Tax: $6,041 (2024)Community: Longboat HarbourCondo
Taxes:$6,041
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
Remarks: Located in the gated waterfront community of Longboat Harbour, this updated first floor residence offers direct walkout access to manicured green space and peaceful water views. Positioned near deeded beach access, the home provides a seamless blend of coastal living and everyday convenience. Interior features include tile flooring throughout, Frigidaire appliances, plantation shutters and automated blinds. The residence is offered turnkey furnished, including a West Elm leather sofa, coordinated coastal accent tables, coffee table, breakfast set and dining table with six chairs. The air conditioning system was replaced approximately two and a half years ago. All appliances and the hot water heater are under warranty, including parts and labor, through February 2027. Covered assigned parking and ample guest parking are included. Longboat Harbour is home to the Longboat Yacht Club, offering an active social calendar and waterfront gatherings for residents, whether or not they maintain a slip. Dock slips are available on a first-come basis for $460 per year. Community amenities include kayak storage and launch, seasonal dock rentals, a fitness center with instructor-led classes, tennis and pickleball courts, sauna, craft room, woodshop, library, and game rooms. No pets permitted. Rentals allowed twice annually with a 30 day minimum.
Listing Agent: Sharon Meier (407-927-5669)
4370 CHATHAM DR #104, LONGBOAT KEY, FL 34228
$470,000137 Days on yellowkey MLS ID: A4674307
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1072 Built: 1969 Tax: $5,334 (2024)Community: Longboat HarbourSpa: NoCondo
Taxes:$5,334
Remarks: Turnkey two-bedroom, two-bath residence in a first-floor, walkout location. Freshly painted with updated baths and 1,172 square feet of living space. Enjoy direct access to the harbor-front walking path and deeded beach access with baths, outdoor shower and chair storage. Includes a covered, assigned parking space. Resort-style amenities include a renovated clubhouse with kitchen and presentation space, fitness center, sauna, pickleball and tennis courts, outdoor grilling and entertainment area, kayak and paddleboard launch with storage, billiards, poker room, woodworking shop, library and bike storage. This self-managed community has strong reserves, no special assessments and no water intrusion from the 2024 storm season. Ideally located near Bayfront Park and just minutes from Publix, Longboat Key Town Center and St. Armands Circle.
4540 GULF OF MEXICO DR #204, LONGBOAT KEY, FL 34228
$595,000193 Days on yellowkey MLS ID: A4667631
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1312 Built: 1975 Tax: $9,451 (2024)Community: Windward BayCondo
Taxes:$9,451
Remarks: MOTIVATED SELLER! FULLY FUNDED RESERVES FOR 2026! PET FRIENDLY! NO UPCOMING SPECIAL ASSESSMENTS! 3 BEACH ACCESS POINTS! MILESTONE INSPECTION PASSED! Welcome to your island retreat, an impeccably renovated 2-bedroom, 2-bath residence offering luxury Longboat Key living at its finest with preserved mangrove and Sarasota Bay views. Every detail has been thoughtfully updated ,this home has been renovated from top to bottom, featuring new flooring, new plumbing, new electrical, new lighting, hurricane-impact windows with shutters for peace of mind and MORE! The brand-new kitchen showcases quartz countertops, custom cabinetry, and all-new stainless-steel appliances, creating a beautiful space that opens to the bright and airy living area. Both bathrooms have been updated with modern finishes and quarts countertops as well. A Murphy bed in the office area adds versatility, perfect for guests or additional workspace. Enjoy deeded beach access directly across the street for endless days on the sand, or take advantage of boat slips available for residents, ideal for boaters looking to explore Sarasota Bay and the Gulf. Windward Bay is a pet-friendly, amenity-rich community offering multiple pools, tennis and pickleball courts, a fitness center with sauna, kayak storage, and walking paths along the bayfront. Perfectly situated near world-renowned restaurants on Longboat Key, St. Armands Circle, and Anna Maria Island, this home combines effortless luxury with the ultimate coastal convenience. Move-in ready and maintenance-free, your Longboat Key lifestyle awaits!
Listing is courtesy of: VRI HOMES (800-531-2885)
Listing Agent: Paulina Vasiliev, Pllc (941-225-5383)
2045 GULF OF MEXICO DR #M1-511, LONGBOAT KEY, FL 34228
$749,00011 Days on yellowkey MLS ID: A4689590
0 Days Off yellowkey (back on 4/12/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1076 Built: 1974Monthly Fee: $1,278 Tax: $9,430 (2025)Community: Seaplace IiCondo
Taxes:$9,430
Remarks: Experience breathtaking, full Gulf views from this beautifully maintained 5th-floor residence at Seaplace on Longboat Key. This furnished 2-bedroom, 2-bath condominium offers the perfect blend of comfort, space, and coastal charm, with expansive living and dining areas designed to capture stunning water views and natural light throughout. Step out to your private lanai and enjoy panoramic sunsets, gentle sea breezes, and the soothing sounds of the Gulf—your own peaceful retreat just steps from the beach. The spacious primary suite provides a relaxing escape, while the guest bedroom offers comfort and privacy for visitors. Seaplace residents enjoy resort-style amenities across 42 acres of lush, meticulously maintained grounds, including a half-mile of private beachfront, two heated swimming pools with spas, a fitness center, Har-Tru tennis courts, walking paths, outdoor grilling areas, and an active, well-managed association. Whether you’re seeking a full-time residence, vacation getaway, or investment opportunity, this unit is priced to sell and ready for you to start enjoying the Longboat Key lifestyle. Schedule your private showing today!
Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
Listing Agent: Michael Renick Pllc (941-400-8735)
100 SANDS POINT RD #225, LONGBOAT KEY, FL 34228
$950,000107 Days on yellowkey MLS ID: A4676681
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1492 Built: 1966 Tax: $3,929 (2025)Community: Sands PointCondo
Taxes:$3,929
Remarks: SELLER IS MOTIVATED AND WILL ENTERTAIN ALL REASONABLE OFFERS! GREAT PRICE REDUCTION !!!! MUST SEE ARCHITECTURAL GEM on Longboat Key! Be in your new home to enjoy summer activities and gorgeous sunsets.Sands Point Condominium is a best kept secret along the beautiful crystal white sands of Longboat Key. This community blends gorgeous mid-century architecture with the stunning location tucked away next to Longboat Key Club. Sands Point offers everything you need to relax and unwind under the Florida sun and all the amenities you could ask for including a private marina. Whether you are a vacationer or full- time resident, you will find this New Pass location one of the best on the island encompassing stunning sunset views. This two bedroom unit is filled with sunlight and has had extensive renovations/remodel (2023) throughout. The beautiful luxury flooring and tall baseboards extend throughout the entire unit. The expansive combination living/dining spaces offer room for large groups or to allow for separate seating areas; all without giving up glorious sunny views. The gorgeous kitchen offers stainless steel Samsung appliances including a French door refrigerator with 2 freezer drawers range and microwave. The double stainless steel sink is a plus for those who love to cook. Beautiful stone countertops top fresh white cabinetry with soft-close doors and drawers. A generous pantry holds all the supplies you need for cooking and entertaining. Dual sides cabinetry forms the breakfast bar offering even more storage. The interior laundry room has GE Insignia washer and dryer and add cabinetry and shelving for storage. Both bathrooms are updated with new cabinetry and countertops. The Primary bedroom is a huge space with a wall of windows; a bright, airy space with ample room for a desk and has both a built-in and a walk-in closet. Both the Primary Suite and the large great room space have stunning views of the Marina. Mid-century charm exudes from the social room gathering space; terrazzo floors and complementing furnishings make this a fun space to gather and entertain. The space includes a kitchen and library area. There is onsite management housed in this building as well. A short walk takes you to the stunning beach-exactly what you come here for! Expansive white sand beach area wraps around the complex. Palapas, beach chairs and a newly renovated pool area overlooks New Pass. Watch the dolphin and enjoy spectacular sunsets. The marina complex offers boat slips on a first come/first serve basis and offers a kayak launch, fishing pier, storage and bicycle storage areas. HVAC new in 2020,. The condo offers an assigned covered parking spot right and a separate assigned storage unit. St Armands Circle, with a variety of restaurants and shops is a short drive away. Easy access to downtown Sarasota and its cultural and entertainment venues. You must see this home to fully appreciate the charm, history and expansive coveted location on the beach of Sands Point. Don't fight the crowds and traffic to enjoy the beach; you are here!!! AMAZING LOCATION near St Armand's Circle, downtown Sarasota and all of the white sand gulf beaches. Own a piece of paradise today!
Listing Agent: Donna Turnbaugh (410-382-4692)
3131 BAYOU SOUND, LONGBOAT KEY, FL 34228
$1,650,00056 Days on yellowkey MLS ID: A4683048
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3023 Built: 1978Monthly Fee: $104 Tax: $15,562 (2025)Community: Bay IslesSingle Family
Taxes:$15,562
Remarks: Wrapped in lush, mature landscaping and set along a tranquil mangrove-lined canal, this waterfront 3BR/2.5BA residence on Longboat Key offers space, privacy and an inviting canvas for future vision. A circular paver driveway and stepped front entry create a gracious arrival, framed by tropical greenery and a classic barrel tile roof. Inside, cathedral ceilings with exposed beams, clerestory windows and a wall of glass sliders fill the great room with natural light. A corner fireplace adds warmth and character, while the open layout feels airy and welcoming. Sliders extend the living space outdoors to a wood deck shaded by a pergola, where peaceful canal views set a calming backdrop for everyday living. The kitchen brings a distinctive mid-century influence, featuring low-profile black-and-white cabinetry, a center island with sink, black stone countertops, white appliances, a breakfast bar, an eat-in area and an adjacent dining space that flows easily into the great room. It is functional and full of personality, with room to reimagine if desired. The primary suite is spacious, offering slider access to the deck and a large bath with dual vanities, spa tub and walk-in shower, presenting an opportunity to update and personalize. Guest bedrooms are comfortably sized, and the guest bath is generous with dual vanities. An in-residence laundry room adds convenience. Outdoors, a caged pool with spa sits privately to the side of the home, while the rear of the property opens to excellent boating water. A private dock and boat lift are positioned along a protected canal, bordered by mangroves and just moments from Sarasota Bay. Located in The Bayou, an intimate gated enclave within Bay Isles, residents enjoy access to the private Bay Isles Beach Club, along with optional membership to the Longboat Key Golf & Tennis Country Club and Harbourside Moorings deepwater slips. This is a rare opportunity to enjoy waterfront living today, with the freedom to shape what comes next in one of Longboat Key’s most desirable communities.
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