Location: Longboat Key
Do Not Show Listings
1581 GULF OF MEXICO DR #507, LONGBOAT KEY, FL 34228
$3,500,000219 Days on yellowkey MLS ID: A4665165
1 Days Off yellowkey (back on 3/20/2026)
Bed: 1 Bath: 1.5 Liv Area Sq Ft: 1721 Built: 2024Community: St. Regis Longboat KeyCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: Under contract-accepting backup offers. St. Regis Longboat Key offers an exceptional opportunity to experience refined living on the pristine sands of Longboat Key. This distinguished five-star resort hotel and private residence enclave commands panoramic views of the Gulf and provides direct beach access, setting the stage for an unparalleled coastal lifestyle. Upon entering this remarkable residence, one is immediately welcomed by voluminous ceiling heights and expansive views that infuse the interiors with abundant natural light. The thoughtful architectural design ensures breathtaking water vistas from the kitchen, oversized balcony, great room, and dining area, creating an ambiance of openness and serenity. The kitchen, equipped with premium Wolf and Sub-Zero appliances, is a testament to both performance and sophistication, perfectly suited for culinary enthusiasts. The primary bedroom suite seamlessly extends into a generous walk-in closet and a luxurious bathroom, complete with a frameless walk-in shower, mechanized commode, and his and her sinks. For ultimate convenience and security, residents may enjoy direct elevator access to their home via keyless entry, setting a new standard in modern elegance. Beyond the residence itself, St. Regis Longboat Key presents a distinguished array of amenities meticulously curated for its residents. The Private Resident’s Clubhouse offers an environment of exclusivity, complemented by a state-of-the-art fitness center, as well as a pool and spa area reserved solely for residential use. Residents are granted privileged access to the legendary St. Regis Butler and Concierge services, which exemplify world-class hospitality and attention to detail. An extraordinary oceanfront spa awaits, alongside diverse dining experiences that showcase the highest standards of culinary excellence. Personal cabanas along the shore create private retreats for relaxation, while the family-friendly amenities include a meandering lazy river and a unique saltwater lagoon. This lagoon is home to a vibrant array of tropical fish species, graceful stingrays, and the resort’s resident tortoises, offering a captivating wildlife experience within the lush grounds. Spanning seventeen acres of beachfront on the coveted Longboat Key barrier island, this private oasis is conveniently located only 3.5 miles from St. Armand’s Circle, the region’s premier destination for shopping and dining. Whether seeking tranquil solitude or an active social environment, every aspect of life at St. Regis Longboat Key has been thoughtfully designed to anticipate and fulfill the desires of its residents. This offering represents more than just a residence; it is an invitation to embrace the legendary St. Regis lifestyle, defined by elegance, comfort, and outstanding service. Begin your journey to extraordinary Gulfside living.
Listing is courtesy of: JAMES BUCHANAN REALTY (941-343-8548)
Listing Agent: James Buchanan (941-376-0064)
775 LONGBOAT CLUB RD #203, LONGBOAT KEY, FL 34228
$1,750,000198 Days on yellowkey MLS ID: A4667025
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2122 Built: 1984Community: Beaches Of Longboat Key Ph-1Condo
Remarks: Welcome to your dream beachfront retreat, nestled behind the exclusive gates of the prestigious Longboat Key Club. This exquisite 3-bedroom, 3-bathroom Gulf-front residence captures breathtaking, unobstructed views of the sparkling turquoise waters of the Gulf from every room—an ever-changing canvas of sunlight, sea, and sky. From the moment you enter, you're greeted by expansive walls of glass that bathe the interiors in natural light and frame the stunning panoramic seascape. Every corner of this residence is infused with the tranquil energy of the ocean, from the shimmering waves to the soft sea breezes that drift through the impact-rated sliding glass doors and windows. The spacious open-concept living and dining area is designed for effortless entertaining, offering a front-row seat to the water. Whether hosting friends or enjoying a quiet evening at home, you'll savor the endless horizon stretching beyond your wraparound balcony—a perfect place to sip morning coffee at sunrise or unwind at sunset. The Kitchen has abundant counter space, generous storage, a built-in desk, and a charming breakfast nook overlooking the beach. Each of the three expansive bedroom suites offers privacy and comfort, with en-suite bathrooms, ample closet space—including dual closets in the primary suite. Freshly painted interiors, electronic shades in every room and new carpeting in the primary suite add a fresh, move-in-ready feel. Unlike many condominiums, this residence offers the space and storage of a single-family residence, including in-unit laundry and generous closets throughout. And with no neighboring buildings in sight, you'll enjoy uninterrupted views and a sense of peaceful seclusion rarely found in beachfront living. Step outside and indulge in resort-style amenities at The Beaches, including 24-hour concierge services, two Har-Tru tennis courts, a heated beachfront pool and spa, fitness center, and a club room with catering kitchen. Mere steps from your door lie the powdery white sands and warm waters of the Gulf—perfect for sunbathing, shelling, or a sunset stroll. For the ultimate in luxury, residents may also join the renowned Longboat Key Club, offering access to two championship golf courses, a world-class spa & wellness center, tennis courts, fine dining restaurants, and a deep-water marina. Located on the coveted south end of Longboat Key, you're just minutes from the chic boutiques and dining of St. Armands Circle and the vibrant arts and culture of downtown Sarasota. This is more than a home—it’s a lifestyle. A rare opportunity to own a slice of paradise where the Gulf meets the sky. Welcome to beachfront living at its most luxurious.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Courtney Tarantino (941-893-7203)
651 BROADWAY ST, LONGBOAT KEY, FL 34228
$2,795,000151 Days on yellowkey MLS ID: A4672952
2 Days Off yellowkey (back on 3/19/2026)
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 3320 Built: 2003Community: Longbeach On Longboat KeySingle Family
Remarks: Under contract-accepting backup offers. Experience island living at its finest in this exquisite coastal retreat in the historic Village on Longboat Key. This home offers a refined blend of relaxed coastal charm and timeless sophistication throughout more than 3,300 heated square feet. The meticulously designed interior includes elegant crown molding, coffered ceilings, custom doors, impact windows and an elevator from the garage to each level. The great room features dramatic ceiling height and opens to a large covered terrace overlooking an exceptionally private backyard, creating an ideal setting for quiet evenings and effortless entertaining. The gourmet kitchen is a chef’s dream with rich wood cabinetry, granite countertops, natural gas cooktop, a pot filler, center island with sink and second cooktop, and a bright breakfast nook that opens to a covered terrace, ideal for morning coffee. Adjacent dining and living areas flow seamlessly and are enhanced by a coffered ceiling and French doors to the charming terrace. The second-level primary suite serves as a serene retreat with polished wood floors, an intricate coffered ceiling, a comfortable seating area, and a private covered balcony for enjoying peaceful moments under the morning or evening sky. Elevated views and sound of ospreys add to the sense of tranquility. The suite also features a spacious en-suite bath with soaking tub and two walk-in closets. Three additional bedrooms provide comfort and flexibility for guests or work needs. Outdoors, a resort-style saltwater pool and spa with integrated features are surrounded by lush landscaping and generous lounging space. The expansive ground-floor lanai and outdoor kitchen further enrich the indoor-outdoor living experience. A circular brick drive accommodates more than 10 vehicles, and the oversized two-and-a-half-car garage and first-level area offer abundant storage, ideal for bicycles, golf carts, kayaks and more. The home and pool are centered on a 12,000-square-foot lot, and an adjacent 6,000-square-foot parcel is also available from the same owner for those interested in expanding or creating a larger compound. This unique golf cart friendly community is surrounded by waterfront restaurants, quaint shops, cafés, fitness centers, fishing piers, a boat ramp on Sarasota Bay, kayak launch areas and a pristine Gulf beach just moments away with no mandatory HOA. We invite you to experience this remarkable home in person to fully appreciate its beauty and lifestyle.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Cindy Fischer (941-465-1124)
100 SANDS POINT RD #324, LONGBOAT KEY, FL 34228
$1,100,000712 Days on yellowkey MLS ID: A4609759
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1941 Built: 1966Community: Sands PointCondo
Remarks: BACK on the market after beautiful renovations!! Unit is impeccably maintained. It has a new air conditioner, roof and upgraded insulation. It is being offered below appraised value! Sands Point is the most remarkable and unique complex on Longboat Key. Built in 1966, the building is a magnificent example of mid-century modern architecture. The complex faces directly onto New Pass, and the outdoor pool and patio have both privacy and spectacular views. The center of the unit is a large great room that features a wall of windows and a view of lush Florida greenery, the boat dock and the navigable inlet which leads to the Gulf of Mexico. Kitchen and bathrooms are renovated. Furniture and furnishings are included in the sale. Windows have been upgraded to the highest level available. Each unit comes with a small storage locker near the boat docks and covered parking. There are boat docks on the premises, approximately 30 ft., that can be rented depending on availability. Management has updated status and detailed information. Sands Point is located adjacent to The Resort at Longboat Key Club with its amenities of golf, health spa, lodging and a restaurant. Nearby is the famous St. Armand's Circle that offers elegant or casual dining and entertainment. Seasonal rental is a huge draw for this property. It may be rented once a year for a minimum of one month.
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Carolyn Clark, Pa (941-685-6131)
1000 LONGBOAT CLUB RD #402, LONGBOAT KEY, FL 34228
$1,045,000175 Days on yellowkey MLS ID: A4670053
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1290 Built: 1972Community: Privateer SouthCondo
Remarks: Coastal Elegance at Privateer South, Longboat Key! Set directly along the Gulf of Mexico, this beautifully renovated two-bedroom residence at Privateer South offers effortless beachfront living within the gates of the prestigious Longboat Key Club. Move-in ready, every detail of this turnkey fourth-floor getaway speaks to comfort, style, and sophistication, framed by sweeping Gulf views and warm coastal light. Porcelain tile floors extend throughout, creating a seamless flow from room to room, while all-impact glass sliders and windows frame tranquil vistas and ensure peace of mind. The open-concept great room is spacious yet inviting, with defined living and dining areas that connect effortlessly to one of two private terraces—perfect for morning coffee or evening sunsets over the water. The modern kitchen features solid wood, shaker style cabinetry (unified throughout the home), sleek granite countertops, stainless-steel appliances, wine refrigerator, and breakfast bar seating, offering the perfect blend of beauty and function. Built-in shelving adds both storage and architectural character, while subtle lighting and window treatments complete the refined aesthetic. The primary suite serves as a private retreat with direct terrace access, a generous wall-to-wall custom-built closet, and a revamped en-suite bathroom featuring dual vanities, granite counters, and a spacious shower with multiple heads. The second bedroom is thoughtfully designed to function as a stylish office or guest suite, complete with a walk-in closet and custom Murphy bed concealed behind clean cabinetry—ideal for flexible use of space. A second full bath with tub/shower combination is equally well-appointed. Two terraces—overlooking the shimmering Gulf and eastern sunrise views—extend the living experience outdoors. The residence also includes an assigned covered parking space, the convenience of interior laundry, and abundant storage throughout. Privateer South is one of Longboat Key’s premier beachfront communities, offering resort-style amenities in a serene and secure setting. Residents enjoy a Gulf-front heated pool and spa, tennis and pickleball courts, fitness center, and clubhouse, all surrounded by lush tropical landscaping with direct access to one of Florida’s most pristine stretches of sand. Association fees include cable, water, waste collection, grounds care, and 24-hour gated security for a truly maintenance-free lifestyle. Perfectly positioned within the Longboat Key Club gates, the location allows members to enjoy world-class golf, a full-service marina, and exceptional dining just moments away (membership options available separately). A short drive brings you to St. Armands Circle for boutique shopping and fine restaurants, or over the bridge to downtown Sarasota, where theater, art, and culture thrive. Offering a rare combination of coastal tranquility, thoughtful design, and resort-style living, Privateer South #402 captures the best of Gulf-front Sarasota living—an inspired residence where every day feels like a retreat.
Listing Agent: Roger Pettingell (941-387-1840)
1241 GULF OF MEXICO DR #111, LONGBOAT KEY, FL 34228
$950,00054 Days on yellowkey MLS ID: A4684166
Bed: 1 Bath: 2.0 Liv Area Sq Ft: 940 Built: 1996Community: Water Club 01 At Longboat KeyCondo
Remarks: This unique plaza level Water Club residence offers you the convenience of stepping out to the exceptional Water Club amenities and lush grounds that lead to the sandy beach and azure waters of the Gulf of Mexico without the use of an elevator. This spacious 1 bedroom special residence features high 10 foot ceilings and the openness is enhanced by the floor to ceiling windows that captivate the tropical Florida landscaping. This home feels and lives like a beach house and sliding glass doors opening to the terrace complement this feeling by extending the living space to the outdoors and the serene setting. The indoor space is open and flows seamlessly from the living room area to kitchen space which also has a separate eating area open to the balcony and outdoors. The kitchen has granite countertops and high end cabinets and is designed to accommodate the joys of cooking. The floor plan offers privacy for the spacious master suite with a private terrace, elegant master bath and walk-in closet with a dressing area. There is also generous storage area in the condo. The Water Club is a premier Gulf front condominium with exceptional amenities and services. The designer decorated Club House features a professionally equipped gym and his and her spa areas, wine storage, billiard room, library, sunset bar plus a grand ballroom for special and formal occasions and gourmet catering kitchen. When not enjoying the beach, there is a heated elevated beautiful pool and hot tub with plenty of seating plus 4 Har-tru tennis courts. This condo location can also be used as a guest suite to be enjoyed by family and guests. The Water Club is conveniently located just minutes from award winning restaurants, Publix and CVS, St. Armands Circle, downtown Sarasota plus the Longboat Key Club for golf, tennis and restaurants is also nearby.
Listing is courtesy of: DEVELOPERS REALTY LBK, INC (941-799-9096)
Listing Agent: Reid Murphy (941-232-3304)
415 L AMBIANCE DR #A701, LONGBOAT KEY, FL 34228
$6,750,00037 Days on yellowkey MLS ID: A4685660
Bed: 3 Bath: 4.0 Liv Area Sq Ft: 3380 Built: 1992Community: L Ambiance 1Condo
Remarks: This highly desirable southwest corner Royal floor plan, expertly renovated throughout by the high end construction firm Voigt Brothers, offers 180 degree panoramic views from the azure Gulf waters to Sarasota Bay and the downtown city skyline. Exiting the private elevator into the grand foyer leads to an expansive great room with new floor-to-ceiling impact sliders framing breathtaking azure water views. The chef’s kitchen was opened to enhance the Gulf and City views and equipped with top-of-the-line the SubZero, Wolf, and Cove appliances. Adjacent to the kitchen, the breakfast nook boasts big City views and also provides a breakfast/coffee station with refrigerated drawers and access to the southeast facing terrace. The great room combines the spacious dining room area with a 22’X 35’ living space, a built-in wet bar with ice maker and wine refrigeration, and access to the wraparound terrace. Owners are fully pampered in the luxurious primary suite offering two walk-in closets, dual water closets, multiple vanity stations, Hydrosystems soaking tub, separate shower with multiple shower heads and decorator features that must be seen in person. The primary bedroom showcases Gulf water views, access to the wraparound terrace and chic cove lighting. Both guest rooms are ensuite with walk-in closets - one offering southeast views of the Bay and City, the other with direct Gulf views. A versatile 9X16 bonus room can serve as an office, storage or extra bedroom. This unit comes with TWO side by side premium garage parking spaces, a wine locker and additional storage locker. The residences at L’Ambiance are free floating with no common walls between units for ultimate privacy. L’ Ambiance amenities include 24 hour concierge service, gated security, resort-style heated pool & spa, 2 private Har-Tru tennis courts, state-of-the-art fitness and club rooms, several guest suites for extended family use and an onsite resident manager. Located just minutes from St. Armands Circle with its shopping and dining attractions as well as the cultural hub of downtown Sarasota.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Ian Addy, Pa (941-961-8850)
1465 GULF OF MEXICO DR #106, LONGBOAT KEY, FL 34228
$1,295,000161 Days on yellowkey MLS ID: A4670993
1 Days Off yellowkey (back on 3/11/2026)
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1815 Built: 1981Community: Players ClubCondo
Remarks: Welcome to luxury Gulf-front living at The Players Club. This sophisticated furnished residence is a three-bedroom, three-bathroom, end-unit condominium. The great room and two primary suites each provide beautiful Gulf views and private access to the two spacious covered terraces. Its thoughtfully designed floor plan maximizes vistas and natural light across an expansive interior. The residence has undergone a comprehensive renovation, featuring a modern kitchen outfitted with custom cabinetry, quartz countertops, a center island adorned with stainless steel and espresso wood base cabinets, as well as a contemporary tile backsplash and high-end appliances. Additional upgrades include new porcelain plank flooring, freshly interior painting updated all interior doors and hardware, moldings, baseboards designer window treatments, enhanced lighting throughout, and all windows and sliding doors have been replace with impact glass. All bathrooms have been beautifully updated with new cabinetry, countertops, tile, and premium fixtures. The great room layout with two master suites, each providing water views and private access to the extended terrace. Impact-resistant windows and sliding doors have been installed to comply with the latest building codes. For convenience, this residence includes two assigned under-building parking spaces with one being an enclosed garage, accompanied by an external storage room. The Players Club demonstrates a commitment to excellence with recent engineering and reserve studies, ensuring ongoing community stability and maintenance. Elevator systems have been modernized and certified. The association maintains fully funded reserves for long-term reliability. Spanning 11 pristine Gulf-front acres on Longboat Key, this private community offers unparalleled amenities. Life at The Players Club is defined by luxury and leisure. Residents enjoy a newly renovated clubhouse equipped with a state-of-the-art fitness center, library and meeting room, catering kitchen, various gathering spaces, four Har-Tru tennis courts with pickleball capabilities, a 70-foot heated saltwater pool and spa, putting green, fire pits, outdoor grills, lushly landscaped grounds, deeded beach access, and the assurance of 24/7 gated security and on-site management. Players Club is ideally situated near the new St. Regis Resort, with optional membership available at The Longboat Key Club & Resort, granting privileged access to golf, dining, tennis, and the only deep-water marina on the island. Beyond the community, residents benefit from proximity to local conveniences, including Publix, CVS. and boutiques within two minutes, and the upscale shops and restaurants of renowned St. Armand's Circle just five minutes away. The famed cultural amenities, many fine dining options, and shopping in downtown Sarasota is just 15 minutes from The Players Club.
Listing Agent: Michael Moulton (941-928-3559)
340 GULF OF MEXICO DR #124, LONGBOAT KEY, FL 34228
$1,725,000370 Days on yellowkey MLS ID: A4648088
2 Days Off yellowkey (back on 3/18/2026)
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2365 Built: 1991Community: Tangerine Bay ClubCondo
Remarks: One or more photo(s) has been virtually staged. One or more photos have been virtually staged. Only patio photo is virtually staged, no patio furniture is included. Welcome to Tangerine Bay Club, the southernmost condominium on Longboat Key, where refined sophistication meets resort-style livingThis exceptional direct Bayfront end residence offers panoramic views of Sarasota Bay and the feel of a single-family home. Move-in ready with a new roof, the home has been extensively updated by the previous owner, featuring elegant granite countertops in the kitchen and baths. The spacious chef’s kitchen is a standout, complete with a center island, abundant custom cabinetry with built-in spice racks, a striking range hood, and top-tier Thermador appliances, including a 6-burner natural gas cooktop. A large breakfast room just off the kitchen adds casual dining flexibility. The open living and dining areas are ideal for entertaining and include impact-rated windows and sliders, gas fireplace, and gas hookups for both a grill and water heater. Three generously sized bedrooms each feature full ensuite baths. The primary suite impresses with Bay views, private lanai access, and a 7’x10’ custom walk-in closet. The ensuite bath includes a Jacuzzi tub and large multi-head shower. The third bedroom doubles as a den, also with a walk-in closet. Design highlights include 8-ft. mahogany doors, arched doorways, high ceilings, Hunter Douglas blinds, plantation shutters, and a well-appointed laundry room, New Water heater. An oversized 2-car garage provides ample storage. Community amenities at Tangerine Bay Club are unmatched: a 25-meter heated pool, kayak storage, fitness center, tennis and pickleball courts, and on-site management. Residents have the option to purchase a membership to the Bay Isles Beach Club by applying through the property manager. Located in the heart of South Longboat Key, this gated community is just minutes from the upscale shops and restaurants of St. Armands Circle, as well as downtown Sarasota’s vibrant arts scene and white sand beaches. Tangerine Bay Club is renowned for its Mediterranean-inspired architecture, lush 10-acre tropical setting, and active social atmosphere. A truly unique coastal lifestyle.
Listing Agent: Debra Pitell-Hauge (941-356-0437)
528 FOREST WAY, LONGBOAT KEY, FL 34228
$595,000245 Days on yellowkey MLS ID: A4662713
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1440 Built: 1989Community: Cedars East Sec 2Townhouse
Remarks: New Price! Seize the opportunity to acquire a prime, elevated townhome in Cedars East on beautiful Longboat Key. This location is arguably the closest Cedars East property to the pristine, sugar-white sands of the Gulf. This Large Pet-friendly townhome is an Elevated structure, positioned well above the flood plain, ensuring peace of mind. Offer turn-Key Furnished excluded a few personal items. The interior exudes sophistication, featuring stunning crown molding and newer tile flooring throughout the main living areas. The kitchen has undergone beautiful updates, including shaker cabinets, granite countertops, stainless steel appliances, and a beautiful stone backsplash. These premium materials are consistently applied across all three bathrooms, enhancing the home's cohesive design. Ideally open floor plan, The kitchen, complete with a convenient snack bar, seamlessly transitions into the dining ,family room & lanai. The primary bedroom is generously proportioned, featuring a wall of windows for abundant natural light and picturesque views. Its en-suite bathroom is equally spacious, boasting dual vanities. The guest bedroom is ample & includes a walk-in closet. A full-sized laundry room is conveniently located adjacent to the bedroom space. This meticulously maintained residence presents an ideal proposition for both personal enjoyment & lucrative rental income, boasting a flexible two-week minimum rental allowance. With an approximate gross annual income of $50,000, even with several months of owner occupancy or vacancy, this property offers substantial returns. A rare asset on Longboat Key, the oversized garage includes a substantial storage closet, perfect for accommodating hobbies and recreational gear. The exterior received a comprehensive upgrade in 2018 with the installation of low-maintenance Hardi Board Siding and all new High-Impact Windows. In 2023, a brand-new hurricane-rated garage door was installed, further enhancing the home's resilience. Both air conditioning units were replaced in 2021, ensuring optimal comfort and efficiency. Finally, 2024 brought a brand new roof. Cedars East offers the convenience of on-site rental management, if desired. This 66-acre village-like townhome community is enveloped by nature, providing effortless access to both the beach and the bay on the beautiful north end of Longboat Key. The spacious and tropical community features lit boardwalks winding through mangroves, leading to an array of exceptional amenities including a heated Jr. Olympic Size Pool, nine Har-Tru Tennis Courts, three Pickleball courts, a Clubhouse with a Pro-Shop, a 24-hour Fitness Center, a Tiki bar, a restaurant, a fishing pier, and a kayak launch. Please note that some amenities require an additional club membership. The property is within walking distance to a variety of local attractions, such as Harry's Deli & Continental Kitchen, the true island gem that is Joan Durante Park, Euphemia Haye Restaurant & The Haye Loft, and, of course, Longboat Key's globally renowned sugary white sand beaches. Furthermore, it offers convenient proximity to other major attractions and cultural venues, including St. Armand's Circle, Mote Aquarium, the Asolo Repertory Theatre, Van Zel Performing Arts Center, Marie Selby Gardens, Anna Maria Island, the Ringling Museum complex, and numerous dining options on Longboat Key and in downtown Sarasota. Lots to love here, come see it today.
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (941-387-8888)
Listing Agent: Jesse Griffin (941-822-6165)
2550 HARBOURSIDE DR #333, LONGBOAT KEY, FL 34228
$1,495,000 MLS ID: A4678404
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 3067 Built: 1990Community: Marina BayCondo
Remarks: Set within a living canopy of mangroves and coastal trees, this BAYFRONT residence invites a more immersive relationship with Sarasota Bay—where filtered light, birdsong, and gentle water movement define everyday living. Behind the gates of Bay Isles on Longboat Key, this approximately 3,000-square-foot waterfront residence offers the ease and scale of a single-family home with the security and convenience of condominium living. With three bedrooms and two-and-a-half baths, the layout lives expansively, enhanced by abundant storage and thoughtful separation of living spaces. Floor-to-ceiling glass sliders in the main living areas and primary suite face east, capturing peaceful sunrise light over Sarasota Bay in a setting best described as park-like waterfront—where mature coastal trees frame the water, creating a serene, private “treehouse” ambiance. Boats glide through the mangrove preserve and lagoon toward open bay waters, accompanied by birdsong and rustling leaves. Two balconies extend the living space outdoors, including a nearly 400 sq ft screened lanai ideal for relaxed coastal living. The primary suite features bay views from bed, terrace access, dual walk-in closets, and a spa-like bath with a freestanding soaking tub, dual vanities, and a glass-enclosed shower. The second and third bedrooms share access to a west-facing balcony, offering sunset light and cross-breezes. The kitchen is both functional and social, featuring quartz countertops, a Sub-Zero refrigerator, generous prep space, a built-in desk nook, mini-fridge and wet bar—well suited for entertaining or casual mornings. A dedicated walk-in laundry room adds practicality with a butcher-block workspace, hutch, and tool cubby. Comfort and peace of mind are prioritized with two A/C zones, new condensers (2025), and two hot water tanks (2021) equipped with a flood-stop device. Brand new carpet and paint. Additional highlights include air-conditioned storage, one assigned garage parking space, and exceptional closet capacity—five linen closets, three pantry closets, and three walk-in closets. Residents enjoy on-site management, a fitness center, tennis and pickleball courts, a heated resort-style pool, car washing area, and EV charging stations. The building features a brand-new roof completed in 2025. Pet-friendly. The location is as compelling as the home itself: secure, serene, and walkable. Adjacent to the Longboat Key Club Marina, and just blocks from Publix, CVS, the post office, and banking, this location allows for a genuinely walkable daily rhythm—rare on Longboat Key. As part of Bay Isles, residents also enjoy access to the Bay Isles Beach Club, a private Gulf-front retreat with gated parking, pavilions, grilling areas, restrooms, and seating for sunset views. Deeded beach access ensures a premier spot on the sand. Membership to the nearby Longboat Key Club is available, offering championship golf, world-class tennis, a full-service spa and wellness center, waterfront dining.
Listing is courtesy of: INVESTMENTS IN SARASOTA (941-894-6059)
Listing Agent: Lee Mirman (941-587-0740)
635 JUNGLE QUEEN WAY, LONGBOAT KEY, FL 34228
$2,895,000 MLS ID: A4679064
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 3047 Built: 2025Community: Mary Regina ReeseSingle Family
Remarks: This gorgeous modern, elevated new 2025 masterpiece on fabulous Longboat Key has just made a significant price reduction! Built to the utmost of standards by the owners vision for his own family, (he is a also builder), this home has it all. Let’s start with the heavy custom front door surrounded by gorgeous large scale tiles in colors of the sea, that opens to the expansive great room, dining area and huge chefs kitchen. The kitchen is an entertainers dream, with a 5 burner gas range, pot filler, double ovens, built-in microwave and full size side by side refrigerator/freezer. A large center island provides ample storage and incredible work space, and of course there is a walk-in pantry and a separate area for a coffee and a wine fridge. Off of the kitchen and living/dining area is a screened in porch with a full outdoor kitchen for outdoor dining as well as an open porch with steps to the lush green grass. The primary suite is on this level, and a half bath and a gorgeous ensuite. The ensuite features an abundance of light with double sinks, a large double shower and a soaking tub. When you head up the staircase to the 2nd level, you will certainly notice the continuance of the incredible finishes and modern original light fixtures! Here you find a large landing with sliders to the enticing outdoor deck, perfect for your morning workout overlooking the beautiful neighborhood or just a spot for some sunset sky watching or midnight stars. 3 bedrooms, two with a jack and jill and one with a full ensuite make easy use of the space for all of your family and friends. Room for a pool on the side yard, plus deeded beach access across Gulf of Mexico Drive, make this a contemporary beach house to remember! This special, walkable mid-key location puts multiple dining, shopping and wildlife exploring destinations right at your doorstep, but you also have the opportunity for the world-renowned St.Regis Resort, St. Armands Circle and the cultural epicenter of Downtown Sarasota within a short drive. This is truly a lifestyle worth exploring. Make your private appointment today!
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
3710 GULF OF MEXICO DR #E3, LONGBOAT KEY, FL 34228
$175,000 MLS ID: A4592507
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 680 Built: 1983Community: Gulfshore Of Longboat KeyManufactured Home
Remarks: JUST ELEVATED! Gulfshore of Longboat Key, Inc. offers it all. It extends from the Gulf of Mexico to Sarasota Bay. It has approximately 450- 500 feet of frontage on the Gulf, a marina on Sarasota Bay, a large heated community pool, fabulous club house with a commercial kitchen and much more. It is one of the best kept secrets on Longboat. Truly, Gulfshore is a remnant of Old Florida that is just six miles from the world-famous St. Armands Circle with fabulous shopping and gourmet restaurants. This unit was manufactured in 1983 and has sustained damage from the two recent hurricanes. All water damage has been addressed. (Please note, parts of this listing describe the interior layout as it was before flooding). The interior is now a blank canvass allowing the buyer to design their own layout. This home previously featured a large living room, kitchen, dining room, two bedrooms, and a full bathroom. It also has a separate bath house/bathroom (requires remodeling) with a shower that is perfect for when you return from the beach. The driveway can accommodate two cars. Most importantly, the unit has been elevated to four feet and a new electric feed has been installed. In addition, new steps have been built for the front entrance. Gulfshore is a 55+ community and does not permit rentals or pets. This home, combined with the amenities offered by Gulfshore and the surrounding area, will make it easy for you to own a piece of paradise on Longboat Key.
Listing is courtesy of: EDGEWATER REAL ESTATE, INC (941-778-8104)
Listing Agent: Bill Shuttleworth (941-779-8877)
5055 GULF OF MEXICO DR #421, LONGBOAT KEY, FL 34228
$575,000 MLS ID: A4684543
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1484 Built: 1973Community: Club Longboat Beach & TennisCondo
Remarks: Set within the highly regarded Club Longboat Beach & Tennis on Longboat Key, this 2BR/2BA residence offers an excellent opportunity to create something truly special in one of the island’s most amenity-rich communities. Just under 1,500 sq. ft. and located on the second level, the residence enjoys a comfortable layout where the primary suite opens to a private terrace, bringing in light and breezes throughout the day. The dining area features a tray ceiling and flows easily into the living room, where a full wall of sliders leads to an open terrace and invites indoor and outdoor living to blend naturally. The space is ready for your personal design vision, offering a solid canvas in a location where lifestyle often takes center stage. Life at Club Longboat Beach & Tennis is known for its mix of recreation, flexibility and beachfront access. Residents enjoy 750 feet of pristine shoreline, eight Har-Tru tennis courts, pickleball courts, two heated pools, a fitness center and a relaxed, social atmosphere. Pet-friendly with 2 pets, no weight restrictions and a rental policy allowing one-month minimum stays up to twelve times per year, this residence is ideal for a full-time escape, seasonal retreat or investment opportunity.
Listing Agent: Bruce Myer (941-376-5311)
2600 HARBOURSIDE DR #R9, LONGBOAT KEY, FL 34228
$335,000 MLS ID: A4661661
Bed: Bath: 0.0 Community: Longboat Key MooringsDock-Rackominium
Remarks: Embrace Unparalleled Elegance: Exquisite 75’ Boat Slip on Longboat Key’s premier R dock, Your Gateway to a Refined Gulf Coast Yachting Experience. Discover the pinnacle of luxury boating with this stunning 75’ x 21’ deep water boat slip, perfectly situated on the spectacular R dock at Longboat Key Club Moorings Marina, nestled along Florida’s breathtaking Gulf Coast. Slip R-9 offers unrivaled views and the closest proximity to the inlet for effortless navigation, with serene waters and vibrant sunsets and the spectacular Sarasota sky line across the bay, as your backdrop—a gateway to an extraordinary yachting lifestyle. Located on Longboat Key, Slip R-9 provides direct access to the Intracoastal Waterway, ideal for deep-sea fishing or leisurely cruises. Enjoy upscale conveniences like Publix, CVS, Chase Bank, a post office, and public tennis courts just moments away. A complimentary shuttle connects you to the chic boutiques and gourmet dining of St. Armands Circle, while you can easily boat to iconic North Longboat Key restaurants like The Shore and Mar Vista, or nearby favorites like Chart House and Dry Dock Waterfront Grill, where fresh seafood and stunning views await. Longboat Key Club Moorings Marina is renowned for its elegance, offering high-speed Wi-Fi, water, laundry facilities, and pump-out services for a seamless experience, with pristine facilities and attentive staff catering to your every need. Visit by boat the nearby sandbars for leisurely afternoons in turquoise Gulf waters, or opt for membership to the Bay Isles Beach Club or Longboat Key Club for access to pristine, sandy beaches and world-class amenities. Unlike other slips, R-9 is not covenanted, meaning Longboat Key Club membership is optional, giving you the freedom to tailor your lifestyle with access to championship golf courses or the exclusive beach club at your discretion. Slip R-9 is more than a boat slip, it’s an invitation to a coastal lifestyle, with quick access to open waters, dining destinations like The Shore and Mar Vista, magical sandbars, and elite recreational opportunities. Own a piece of paradise in this A+ location, where every detail is designed for elegance and ease. Pursuant to condo rule this slip will accommodate a yacht with LOA of 70ft and 17ft beam and will be subject to association approval.
Listing is courtesy of: COLDWELL BANKER REALTY (941-907-1033)
Listing Agent: Mark J Baron (941-241-7633)
1065 GULF OF MEXICO DR #305, LONGBOAT KEY, FL 34228
$1,299,000 MLS ID: A4681609
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1819 Built: 1981Community: Beachplace IiiCondo
Remarks: One or more photo(s) has been virtually staged. A vivid palette of white perfected with the backdrop of crystal sand meets azure Gulf blue….. finished off with brilliant hues over the spanning skies as the sun sets on yet another perfect day. Yours to be experienced daily, from the inside or out on the patios, at this corner condo home spread over more than 1,800 square feet. Well-positioned at the southwest corner of Building 10 to take full advantage of what it means to be the fortunate owner of a beachfront Longboat Key retreat. Clean, crisp and white, this home is move-in ready, OR it is fresh and primed for you to begin the design of your dreams. Finding 3 bedrooms, 2 baths, and 2 owned parking spaces (one under-building and one outside steps to the building entry) on the beach at this reasonable price point is a FIND in this zip code, so closely consider the opportunity at hand. Beachplace is a sprawling community of 31 acres and full of amenities including, but not limited to, deeded beach access, junior Olympic size pool, kiddie pool, spa, clubhouse, fitness, tennis, pickleball, guarded/ gated entry, community grilling, fun gaming area with ping pong, cornhole, seasonal community activity calendar, etc. Truly a special place to call home or an absolute escape to refresh, restore, relax, release and renew the wellbeing of mind, body and spirit.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Cindy Schatzle (941-587-7556)
2110 HARBOURSIDE DR #547, LONGBOAT KEY, FL 34228
$929,000 MLS ID: A4681901
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2105 Built: 1988Community: Fairway Bay 3Condo
Remarks: Experience refined coastal living behind the gates of the prestigious Bay Isles. This beautifully appointed 3-bedroom, 2-bath residence in The Atrium offers an exceptional blend of elegance, comfort, and convenience just minutes from St. Armands Circle and vibrant downtown Sarasota. Designed for effortless living and entertaining, the open floor plan showcases high ceilings, a sophisticated blend of tile and wood flooring, and expansive walls of glass sliders that bathe the interior in natural light. The spacious terrace captures panoramic views of Sarasota Bay and the sparkling city skyline, an idyllic backdrop for breathtaking sunrises and tranquil evening reflections. The primary suite is a serene retreat with direct terrace access, dual walk-in closets, and a spa-inspired en-suite bath featuring dual vanities, a soaking garden tub, and a glass-enclosed walk-in shower. Two additional guest bedrooms provide comfort and privacy, each with private balcony access, ideal for hosting family and friends. Additional highlights include secure garage parking and a private storage unit. The home offers a newer high-end HVAC system with UV germicidal light and integrated dehumidifier, plus a newer hot water heater for added reliability. Hurricane shutters and smart home features allow remote controls of shades, lighting, ceiling fans, and thermostat for efficiency and peace of mind. Residents enjoy 24/7 security through Bay Isles, adding comfort and exclusivity. Residents enjoy exclusive access to the Bay Isles Beach Club, located just across from the community, offering a private Gulf-front beach, restrooms, covered picnic areas, barbecue grills, and a volleyball court. The Atrium enhances the lifestyle further with a heated swimming pool, tennis and pickleball courts, clubhouse, fitness center, and on-site management. This is a rare opportunity to own a bay-view residence in one of Longboat Key’s most sought-after gated communities, where luxury meets relaxed coastal sophistication.
Listing Agent: Mimi Kruk (941-587-5188)
1920 HARBOURSIDE DR #1003, LONGBOAT KEY, FL 34228
$684,500 MLS ID: TB8462750
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1590 Built: 1982Community: Fairway Bay 1Townhouse
Remarks: Start your day with glowing sunrise views across Sarasota Bay from the living room, primary suite, and screened lanai, where the waterfront setting makes every moment feel like a retreat. Located within the gated waterfront enclave of Bay Isles, this spacious 2-bedroom, 2.5-bath townhome offers effortless island living with serene bay views and a flexible layout. The main living level is thoughtfully designed for everyday living and entertaining, featuring an open living and dining area complemented by a wood-burning fireplace. The kitchen offers ample space for casual meals and future customization. Large sliders extend the living space to a screened lanai overlooking the bay—an ideal spot to unwind or host guests. Hurricane shutters are already installed, offering added security and peace of mind. Upstairs, two well-proportioned bedroom suites each include private baths and walk-in closets, providing comfort and privacy for owners and guests alike. The primary suite is highlighted by a light-filled bath with an oversized soaking tub with jets and skylights above, creating a relaxing, spa-inspired atmosphere. A versatile loft area with additional skylights offers flexibility for a home office or gym, den, or reading space. On the ground level, an oversized two-car tandem garage delivers exceptional storage and functionality, with room for hobbies or a workshop. Residents of Fairway Bay enjoy a pet-friendly environment, professional on-site management, lushly landscaped walking and biking paths, and a private heated pool. Ownership also includes access to the exclusive Bay Isles Beach Club, a private Gulf-front amenity offering pavilion seating, tropical cabanas, grilling and picnic areas, beach storage, kitchen prep, and private restroom facilities. Ideally situated near the beaches, golf, dining, and shopping of Longboat Key, this townhome presents a rare opportunity to own in one of the island’s most established and desirable communities.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Connor Meckley (941-279-0013)
530 CHIPPING LN, LONGBOAT KEY, FL 34228
$5,799,000 MLS ID: A4685275
Bed: 5 Bath: 6.0 Liv Area Sq Ft: 4216 Built: 2026Community: Country Club Shores Sec 02Single Family
Remarks: Introducing the newest custom residence by Brista Homes, where exceptional craftsmanship and thoughtful design come together in a limited and highly refined offering. Nestled along a quiet canal in the sought-after waterfront community of Country Club Shores, this 4216 square-foot residence captures the essence of the Longboat Key boating lifestyle. With desirable south-facing rear exposure, tranquil canal views create a peaceful backdrop to daily living, while upper balconies frame beautiful views of Sarasota Bay. The home’s architecture, floor plan, and interior selections were curated by Brista’s in-house design team, drawing on years of experience building on Longboat Key and a deep understanding of what today’s waterfront buyers value most—timeless architecture, premium materials, and seamless indoor-outdoor living. A handcrafted iron pivot entry door framed by natural stone detailing creates a striking first impression. Inside, pocketing glass doors open the main living spaces to a resort-style outdoor setting where a custom salt water pool and elevated heated spa are surrounded by porcelain pavers and lush coastal landscaping. A fully equipped outdoor kitchen creates the ideal setting for entertaining along the water. At the heart of the home, the kitchen blends refined design with exceptional functionality. Custom Italian cabinetry is complemented by a dramatic Quartzite waterfall island and matching hood feature. A premium appliance suite by Miele — including a built-in refrigerator, integrated dishwashers, speed oven, and built in coffee maker — is complemented with a striking 48-inch dual-fuel range. A hidden butler’s pantry and custom wine display add both style and practicality for effortless entertaining. The great room centers around a sleek linear fireplace, creating a sophisticated gathering space. Upstairs, a spacious club room with a media wall and wet bar offers a relaxed setting for evenings with family and guests. Architectural details throughout the home include white oak plank flooring, a dramatic floating staircase, recessed baseboards, and clean modern lines that reflect a refined coastal aesthetic. Modern conveniences include whole-home audio, a whole house generator, multi-zone climate control, and integrated security. Located within one of Longboat Key’s most desirable boating communities, where deepwater canals provide quick access to Sarasota Bay and the Gulf of Mexico, this newly completed custom residence represents a rare opportunity to experience waterfront living defined by thoughtful design, exceptional craftsmanship, and enduring quality.
Listing is courtesy of: BRISTA REALTY LLC (941-373-0500)
Listing Agent: Gina Ursini (941-812-4894)
5840 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$4,950,000 MLS ID: A4670094
Bed: 4 Bath: 5.0 Liv Area Sq Ft: 4145 Built: 2022Community: Longboat KeySingle Family
Remarks: Longboat Key Waterfront Estate with Rare Beach and Boating Access. Designed by Stofft Cooney Architects and built in 2022 by Perrone Construction, one of the Gulf Coast’s premier luxury builders, this stunning coastal residence is a rare offering that blends modern design, structural integrity, and an exceptional location. Positioned on the desirable northern end of Longboat Key, the home offers a lifestyle few can match, with both deeded beach access directly across the street and canal frontage in the backyard. Where most homes require a choice between Gulf or Bay, this property offers the best of both. Step inside to discover a layout designed for both comfort and sophistication. The main level features a serene primary suite with a spa-inspired bathroom, a seated vanity, and a custom walk-in closet. A thoughtfully planned home office includes a custom built-in desk with dual workstations, offering dedicated space for both homeowners. The open-concept living area flows effortlessly into the designer kitchen, outfitted with quartz counters, Thermador appliances, a paneled refrigerator and freezer, wine fridge, and ice maker. A hidden walk-in pantry provides additional prep space and ample storage. Upstairs, a central family lounge connects three en-suite bedrooms, two with tranquil canal views where manatees are often spotted lingering at the water’s surface. The upper level is easily accessed by both a residential elevator and a beautifully crafted staircase with integrated storage. Every room has been carefully curated to reflect the home’s effortless luxury. For buyers seeking a fully realized, move-in-ready experience, furnishings can be negotiated separately. Outdoor living is elevated with a heated saltwater pool and spa, expansive lounging and dining terraces, and a fully equipped summer kitchen featuring stone counters, a Lynx grill, and built-in refrigeration, all protected by push-button retractable hurricane shutters. A dedicated pool bath adds convenience and keeps wet feet out of the house. The private dock includes a 16,000-pound boat lift, a 4,500-pound kayak or jet ski lift, plus additional space to dock a larger vessel in the water. The dock is fully outfitted with shore power, running water, integrated lighting, and a fish-cleaning station, ready for both adventure and convenience. Built high and dry, the home remained fully protected during recent storms, a true reflection of the enduring quality behind its construction. Combining beauty, function, and peace of mind, this is a rare opportunity to enjoy the very best of Longboat Key living, free from compromise.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Toni Zarghami (941-248-2147)
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