Location: Longboat Key
Do Not Show Listings
1581 GULF OF MEXICO DR #406, LONGBOAT KEY, FL 34228
$6,750,00043 Days on yellowkey MLS ID: A4685503
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2347 Built: 2024 Tax: $50,055 (2025)Community: St. RegisSpa: NoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$50,055
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Perched above the shimmering shoreline, this exquisite two-bedroom, two-and-a-half-bath residence at The St. Regis Longboat Key Resort offers breathtaking panoramic views of the turquoise waters of the Gulf of Mexico and the resort’s serene saltwater lagoon. Designed for both refined comfort and effortless coastal living, the residence showcases exceptional craftsmanship and sophisticated design throughout. A defining feature of this residence is the expansive private terrace, where all principal rooms open seamlessly to the outdoors. Complete with a gas grill, this exceptional outdoor living space provides sweeping views of the Gulf of Mexico and the tranquil lagoon—creating the perfect setting for al fresco dining, entertaining, or simply enjoying spectacular sunsets over the water. The gourmet kitchen is a true showpiece, appointed with sleek Poggenpohl cabinetry and premium appliances including Wolf double ovens, a gas cooktop, microwave, icemaker, and wine refrigerator. A generously sized island provides abundant built-in storage, making the space as functional as it is beautiful. This thoughtfully designed floor plan features two luxurious owner’s suites. The primary suite enjoys stunning views of the Gulf of Mexico and opens directly onto the large terrace. The spa-inspired bathroom features a large double vanity with elegant lighted mirrors plus a separate makeup vanity, two private water closets, a seamless glass shower, and a freestanding soaking tub. Electronic sheers and blackout shades provide effortless ambiance and privacy, while a custom-built closet offers exceptional storage. The second owner’s suite also captures captivating Gulf views and opens onto the terrace. Its spacious bath includes dual vanities with lighted mirrors, a water closet, and custom-built closets. Electronic sheers and blackout shades add both convenience and luxury. Additional highlights include a large laundry room with sink, cabinetry, and hanging rack, as well as an elegantly designed powder room for guests. Offered completely turnkey, the residence is beautifully furnished and enhanced with custom light fixtures throughout, creating a sophisticated yet inviting coastal retreat. Nestled within the first branded residential community and ultra-luxe 5 star resort on the Gulf of Mexico. The Residences at The St. Regis Longboat Key blend legendary service with the allure of a seaside getaway. Spanning over 17 acres with 800 feet of direct beachfront, this community offers unparalleled amenities, including the signature St. Regis Butler and Concierge services, a world-renowned St. Regis Spa, in residence dining. Resident only amenities include a clubhouse, fitness center, pool/spa and beach area. Enjoy your private resident only amenities, while having access to all the resort has to offer. Live like you are on vacation all year round!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Lynn Morris, Pllc (941-400-4526)
1561 GULF OF MEXICO DR #304, LONGBOAT KEY, FL 34228
$13,000,00042 Days on yellowkey MLS ID: A4685495
Bed: 3 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4891 Built: 2024 Tax: $94,589 (2025)Community: St. Regis Longboat KeySpa: NoCondo
Taxes:$94,589
Remarks: Experience the pinnacle of coastal luxury in the highly sought-after Armand building at The St. Regis Longboat Key, where breathtaking Gulf of Mexico views set the stage for an extraordinary living experience. This residence is absolutely breathtaking and is a must see. Designed for both grand entertaining and effortless everyday living, the expansive great room showcases a sophisticated wet bar and wine refrigerator, all enhanced by striking designer light fixtures and elegant sheers that create a soft, ethereal ambiance. Accordion glass doors seamlessly extend the space onto a sprawling wraparound terrace—complete with a private gas grill and unforgettable sunset vistas. Thoughtfully designed, this gracious room transitions beautifully between formal gatherings and relaxed coastal living. The chef’s kitchen is a true centerpiece, featuring premium Poggenpohl cabinetry, a Sub-Zero refrigerator, Wolf double ovens and gas cooktop, dual dishwashers, and a separate breakfast area with bar and microwave. A large island offers additional seating, making it as functional as it is elegant. Or just order room service! The owner’s suite is a private sanctuary, offering stunning Gulf views and a wet bar perfect for morning coffee or evening unwinding. Dual spa-inspired bathrooms provide two luxurious and private retreats—one with custom closets, an oversized vanity, seamless glass shower, and private water closet; the other with a large vanity, dedicated makeup area, custom closets, seamless shower, and private water closet. A spacious and comfortable club room creates an additional venue for entertaining, complete with a wet bar and beverage refrigerator. Two additional guest bedrooms are equally well-appointed, each opening onto a private terrace. One offers Gulf views, custom closets, and a luxurious bath with a large vanity, makeup area, seamless glass shower, and private water closet. The third bedroom is thoughtfully designed for comfort and privacy, featuring accordion doors to the terrace and a beautifully finished bathroom with a large vanity and makeup area, freestanding soaking tub, seamless glass shower, and private water closet. An elegant powder room adds convenience for guests. Additional highlights include a large laundry room with sink, built-in cabinetry, and hanging rack. The residence is offered fully turnkey, with exquisite furnishings curated by the renowned Marc-Michaels Interior Design—featuring designer-selected finishes, statement lighting, refined furniture pieces, and custom window treatments that create a cohesive, sophisticated aesthetic throughout. Modern living is elevated by fully integrated smart home technology, including iPad-controlled systems, electronic sheers, and blackout shades—delivering both convenience and ambiance at the touch of a button. Nestled within the first branded residential community and ultra-luxe 5 star resort on the Gulf of Mexico. The Residences at The St. Regis Longboat Key blend legendary service with the allure of a seaside getaway. Spanning over 17 acres with 800 feet of direct beachfront, this community offers unparalleled amenities, including the signature St. Regis Butler and Concierge services, a world-renowned St. Regis Spa, in residence dining. Resident only amenities include a clubhouse, fitness center, pool/spa and beach area. Enjoy your private resident only amenities, while having access to all the resort has to offer. Live like you are on vacation all year round!
1591 GULF OF MEXICO DR #412, LONGBOAT KEY, FL 34228
$3,950,00092 Days on yellowkey MLS ID: A4679040
3 Days Off yellowkey (back on 3/24/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2154 Built: 2024 Tax: $34,330 (2025)Community: St. Regis Longboat KeySpa: NoCondo
Taxes:$34,330
Remarks: Spectacular Sarasota Bay and city skyline views set the stage for this exquisite and private two-bedroom, two-bath residence at the prestigious St. Regis Longboat Key. Offered fully furnished and thoughtfully designed by Studio G Interiors, the home showcases an elegant coastal aesthetic throughout. A large wraparound terrace with a private gas grill provides the perfect setting for indoor-outdoor living and entertaining. The spacious owner’s suite enjoys breathtaking Sarasota Bay views and features a spa-like bathroom appointed with Poggenpohl cabinetry and quartz countertops. The en suite guest bedroom offers privacy and comfort with custom-designed closets, making it ideal for visitors or extended stays. Additional highlights include electronic blinds throughout, a built-in office area, and a sophisticated wet bar with designer tile, custom shelving, a wine refrigerator, and an ice maker—perfect for entertaining. The gourmet kitchen is beautifully appointed with Poggenpohl cabinetry, a Sub-Zero refrigerator, Wolf double ovens and six-burner cooktop, and a Cove dishwasher. A dedicated laundry room with sink is equipped with an Electrolux washer and dryer. Completing this exceptional residence is a private two-car garage, offering rare convenience and security. Beyond the residence, The St. Regis Longboat Key Resort offers a curated collection of world-class amenities designed exclusively for residents. The private clubhouse includes a state-of-the-art fitness center, a resident-only pool and spa, and access to the signature St. Regis Butler and Concierge services that redefine luxury living. Indulge in the oceanfront spa, diverse dining venues, and beachfront cabanas, or enjoy family-friendly experiences such as a lazy river and saltwater lagoon teeming with tropical fish, stingrays, and resident tortoises. Set on 17 acres of pristine beachfront, and just 3.5 miles from St. Armands Circle’s renowned shopping and dining, this residence represents more than a home—it’s an invitation to embrace the legendary St. Regis lifestyle, where elegance, comfort, and unparalleled service define every moment. Begin your journey to Live Exquisite at The St. Regis Longboat Key.
1591 GULF OF MEXICO DR #216, LONGBOAT KEY, FL 34228
$2,750,000216 Days on yellowkey MLS ID: A4665247
Bed: 1 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1556 Built: 2025 Tax: $25,560 (2025)Community: St. Regis Longboat KeySpa: NoCondo
Taxes:$25,560
Remarks: Step inside this spacious residence to discover a clean, modern interior with a sophisticated Palm Beach vibe. Designed for both style and comfort, this home features a gracious great room featuring floor-to-ceiling windows that flood the interiors with natural light and open to the large, 765 square foot private terrace with a built-in gas grill—perfect for gardening, entertaining friends and family, or relaxing outdoors. The chef’s kitchen is outfitted with Poggenpohl cabinetry, Wolf appliances, a Sub-Zero refrigerator, and Sub-Zero wine and beverage refrigerator, blending elegance with functionality. The owner’s suite also boasts floor-to-ceiling windows, a custom designed closet, and a luxurious bathroom with a frameless walk-in shower, Toto mechanized commode, and double vanities. With generous square footage and a thoughtful layout, this residence easily accommodates overnight guests while maintaining a sense of privacy. Additional features include electronic blinds throughout, adding both convenience and sophistication. Designer light fixtures add an elegant touch throughout the home. St. Regis Longboat Key offers 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 Gulf side living.
455 LONGBOAT CLUB RD #402, LONGBOAT KEY, FL 34228
$2,195,00021 Days on yellowkey MLS ID: A4686984
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2410 Built: 1990 Tax: $18,228 (2025)Community: PierreSpa: YesCondo
Taxes:$18,228
Elementary School: None
High School: None
Middle School: None
Remarks: Gulf-front living takes on a refined sense of scale in this beautifully renovated residence at The Pierre, an intimate waterfront community of just 66 residences set behind the gates of the Longboat Key Club. With 2,400+ sq. ft. of thoughtfully updated living space, the residence offers a seamless blend of comfort, style and presence in one of the island’s most desirable locations. From the moment you enter the foyer, the tone is set with diagonal tile flooring, high ceilings, crown molding and tray accents that create a sense of openness and quiet sophistication. The great room unfolds with ease, connecting living, dining and kitchen spaces in a way that supports both everyday living and entertaining. A full wall of glass in the living area draws in natural light and frames views of the Gulf and manicured grounds, while a custom built-in adds both function and visual interest. The dining area sits adjacent, wrapped in glass and oriented toward the view, creating a natural setting for gatherings. The kitchen has been remarkably reimagined with black stone countertops, off-white cabinetry with glass panel accents, high-end appliances and generous counter space with a breakfast bar. A slider opens to the terrace, allowing for easy indoor-outdoor flow. A private office with double glass doors and a tray ceiling with custom lighting provides a quiet and versatile workspace. The primary suite is spacious and serene, featuring a breath taking view, terrace access and a large bath designed with both comfort and flexibility in mind. Dual water closet areas and a distinctive glass-enclosed circular shower with detailed tilework add a unique architectural element. Guest accommodations are well-sized and welcoming, and an in-residence laundry room adds everyday convenience. Residents of The Pierre enjoy a full complement of amenities, including concierge service, under-building parking, 24-hour security, a fitness center, 2 guests suites, heated pool, spa, children’s pool, Har-Tru tennis courts, shuffleboard courts and private beach access. Membership opportunities at the Longboat Key Club offer access to championship golf and fine dining, all within proximity to St. Armands Circle and Sarasota’s vibrant downtown.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Bruce Myer (941-376-5311)
4401 GULF OF MEXICO DR #601, LONGBOAT KEY, FL 34228
$995,00081 Days on yellowkey MLS ID: A4679728
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1524 Built: 1972 Tax: $14,214 (2024)Community: Longboat Harbour TowersCondo
Taxes:$14,214
Tax Year: 2024
Remarks: Two-bedroom, two-bath residence offering sweeping sixth-floor views of the Gulf of Mexico from Longboat Harbor Towers. This rare southwest corner condominium has completely unobstructed views west and south providing one of the most interesting and protected waterfront visages available anywhere on the key. In largely original condition, this spacious property presents an exceptional opportunity for renovation and customization in one of Longboat Key’s most coveted waterfront locations. Few properties combine this level of potential with such a remarkable setting. Positioned directly on the Gulf with more than 400 feet of pristine beach frontage, this fully amenitized community also enjoys eastern views of Sarasota Bay and the downtown Sarasota skyline—delivering breathtaking sunrises and sunsets from the same home. The southwest exposure also provides much more to view and enjoy with site lines extending down the entire length of the key. Common areas have been recently renovated and include a beachfront, heated, saltwater pool, a complete exercise room and spacious lounge with pool baths. Longboat Key is a sought-after barrier island community known for its relaxed coastal lifestyle, pristine beaches, and upscale residential atmosphere. Ideally located just minutes from the cultural and social energy of Sarasota, residents enjoy convenient access to world-class arts, dining, and entertainment while maintaining a sense of privacy and tranquility. A short drive south leads to iconic St. Armands Circle, renowned for its eclectic mix of boutiques, fine dining, cafés, and year-round events. Beyond St. Armands, downtown Sarasota offers theaters, galleries, live music, waterfront parks, and a thriving culinary scene, making Longboat Key an exceptional blend of island serenity and vibrant city living. This seller also has a BOAT SLIP for sale at The Boathouse, adjacent to the Dry Dock Restaurant just minutes away. Buy the condo and the slip for a complete Florida lifestyle!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: David Jennings (941-650-7354)
415 L AMBIANCE DR #A301, LONGBOAT KEY, FL 34228
$6,100,00019 Days on yellowkey MLS ID: A4688759
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3380 Built: 1992 Tax: $46,418 (2025)Community: L Ambiance 1Spa: YesCondo
Taxes:$46,418
Remarks: Rare corner Gulf-front residence with expansive wraparound terrace and views. An exceptional residence in L’Ambiance, where sweeping water views and refined coastal design converge. This light-filled corner home is defined by an expansive wraparound terrace, offering multiple seating areas and uninterrupted vistas of the Gulf - creating a seamless connection between indoor and outdoor living. Walls of glass frame the horizon from the main living spaces, enhanced by high-impact glass throughout, where generous scale and an open layout provide an effortless setting for both intimate living and entertaining. The kitchen is thoughtfully designed with extensive custom cabinetry, stone surfaces, and a functional layout complemented by a dedicated dining area. A private split-bedroom plan enhances comfort and separation, while a flexible den or media room offers additional space for guests or a home office. Throughout the residence, polished flooring and plantation shutters add a layer of understated sophistication. This residence includes two garage parking spaces, a private wine locker, and additional storage, offering both convenience and security. L’Ambiance offers a boutique beachfront setting with concierge service, a well-appointed fitness center, three guest suites for visiting family and friends, two Har-Tru tennis courts, and an expansive resort-style pool and spa set within beautifully maintained tropical grounds, all with direct beach access. Ideally positioned on the south end of Longboat Key and adjacent to the Longboat Key Club, with optional membership offering access to championship golf, tennis, marina, dining, and a full-service spa, this is a rare opportunity to experience elevated beachfront living.
3466 WINDING OAKS DR #35, LONGBOAT KEY, FL 34228
$795,00015 Days on yellowkey MLS ID: A4686581
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2039 Built: 1988 Tax: $4,919 (2025)Community: Winding OaksCondo
Taxes:$4,919
Remarks: Located in one of the most sought-after villa communities on Longboat Key, this well-kept 2-bedroom, 2-bath home in Winding Oaks lives more like a single-family residence—without all the upkeep. Behind the gates of Bay Isles, it offers a great opportunity to enjoy a quiet, established neighborhood known for its natural beauty and relaxed feel. A paver driveway and walkway, surrounded by mature landscaping, lead you to the front door. Inside, high ceilings and warm wood floors immediately make the space feel open and inviting. The finishes are neutral and timeless, and the natural light really does the rest. Impact glass throughout adds both comfort and peace of mind. The main living area flows easily, with a striking corner of sliding glass doors that brings the outdoors in and opens to a spacious, screened, deck. It’s the kind of space you’ll actually use—whether that’s for entertaining, relaxing, or just enjoying the greenery around you. The kitchen is nicely laid out with stone countertops, stainless appliances, a tray ceiling, and a large window that keeps things bright. Both bedrooms are generously sized. The primary suite feels like a true retreat, with vaulted ceilings, a walk-in closet, and sliding doors that open to the deck with peaceful nature views. The bathroom is spacious, featuring dual vanities, a Jacuzzi tub, walk-in shower, and well-done tile details. Additional highlights include a two-car garage and a floor plan that offers a nice balance of openness and privacy. Winding Oaks is part of the Bay Isles Harbourside golf course community and offers a gated entrance, community pool, and access to Bay Isles amenities—including deeded beach access through the private Bay Isles Beach Club. It’s an easy, comfortable lifestyle in one of Longboat Key’s most desirable communities.
3030 GRAND BAY BLVD #384, LONGBOAT KEY, FL 34228
$1,699,00027 Days on yellowkey MLS ID: A4687630
4 Days Off yellowkey (back on 4/7/2026)
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2550 Built: 1998 Tax: $17,280 (2025)Community: Grand Bay 3Spa: YesCondo
Taxes:$17,280
Remarks: Perched on the eighth floor of Grand Bay’s Building 3, this updated Cayman residence captures sweeping Gulf-to-bay views that stretch across the Harbourside Golf Course, Sarasota Bay, downtown skyline, and the Gulf of Mexico. With more than 2,500 square feet of interior living space and multiple terraces, the residence offers a refined blend of comfort, flexibility, and panoramic scenery in one of Longboat Key’s premier gated communities. The open floor plan has been thoughtfully reimagined to enhance everyday living and entertaining. The current configuration features a spacious great room, a casual family room in place of the traditional dining area, and a dining room reallocated to the den/third bedroom—offering versatility that can easily be adapted to suit a buyer’s preferred layout. Walls of glass sliders frame expansive water, city, and golf course views while filling the interior with natural light. The kitchen has been refreshed in 2025 with new countertops, backsplash, sink, faucet, and disposal, complementing solid wood cabinetry, quartz surfaces, and a breakfast bar that connects seamlessly to the surrounding living spaces. This central hub is designed for both functionality and gathering, with clear sightlines to the terraces and beyond. Recent improvements throughout the residence provide both comfort and peace of mind, including two new HVAC systems (2023 and 2024), a renovated primary bath with updated shower (2022), a new powder room (2020), and oversized tile flooring extending throughout the interior and both terraces (2019). Additional enhancements include a stunning built-in living room wall unit with inset lighting, whole-house Sonos sound system, updated guest bath, and electric storm shutters protecting the waterfront openings. The primary suite is privately positioned and offers direct terrace access, a spacious walk-in closet, and a well-appointed en-suite marble bath with dual vanities, soaking tub, and separate shower. Guest accommodations are arranged in a split layout for privacy, including a generously sized second bedroom suite and a flexible third bedroom or office (currently being used as the dining room). Grand Bay residents enjoy a resort-style lifestyle within the gated Bay Isles community, featuring two heated swimming pools, Har-Tru tennis courts, a fitness center, clubhouse, and 24-hour guard-gated security. Ongoing community enhancements include newly updated elevators, refreshed clubhouse and pool furnishings, exterior painting (2025), and a new roof on Building 3, scheduled for completion in 2026—further elevating the long-term value of the community. Ownership also includes deeded access to the private Bay Isles Beach Club, offering Gulf-front parking, pavilions, and direct access to Longboat Key’s white-sand beaches. Ideally located on the south end of the island, Grand Bay is moments from Harbourside Golf Course, the Longboat Key Club marina, and waterfront dining. St. Armands Circle and downtown Sarasota are just minutes away, where boutique shopping, fine dining, theaters, galleries, and cultural venues define the region’s renowned coastal lifestyle. This residence presents a compelling opportunity to enjoy updated interiors, flexible living spaces, and expansive Gulf-to-bay views within one of Longboat Key’s most established and amenity-rich communities.
Listing Agent: Roger Pettingell (941-387-1840)
5231 GULF OF MEXICO DR #104, LONGBOAT KEY, FL 34228
$545,000110 Days on yellowkey MLS ID: A4676730
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 720 Built: 1973 Tax: $6,784 (2024)Community: Covert IiCondo
Taxes:$6,784
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
Remarks: Have you dreamed of the perfect island getaway situated right on a gorgeous stretch of beach on Longboat Key? And could you even imagine you could have it for $615,000?! With one owner for the last 29 years, this is your unique opportunity to purchase this fully renovated beachfront walkout 1 bedroom, 1 bath condo in the beach to bay island community of Covert II - and hang onto it like these owners have! With this fabulous ground floor location, you can have your toes in the sand in only a few steps! This condo offers Italian porcelain tile throughout and a completely new kitchen with beautiful counter tops, all new cabinets and new appliances. The bathroom has been beautifully updated as well and features custom tile work in a seaside theme. The view is fabulous in either direction with the sparkling pool out front and the gorgeous Gulf of Mexico out back. The open living and dining area allows plenty of space to entertain or to quietly contemplate whether it’s a beach day, a day for a soak in the pool or a walk to the Covert bayside fishing pier. The bedroom offers the same stunning beach view and features sliders to the screened in lanai. The midkey location allows for easy access to multiple restaurants and shopping. The tree filled mangrove trails of Joan Durante Park are a birders’ paradise and the 12 mile long bike path give you many options to soak in the sun while getting in your daily exercise. This is island living at its best at a price you may never thought you could find!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
2425 GULF OF MEXICO DR #1A, LONGBOAT KEY, FL 34228
$1,595,00016 Days on yellowkey MLS ID: A4688987
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1470 Built: 1973 Tax: $9,602 (2025)Community: Sea Gate ClubSpa: NoCondo
Taxes:$9,602
High School: Booker High
Remarks: This is the gorgeous ground floor, walk-out unit next to the beach you've been looking for. Do you prefer to live like a single family home, no elevator, and walk straight out to the beach? Then this is the One! Welcome to Sea Gate Club on beautiful Longboat Key, perfectly positioned near mid-island, and close to shopping at Publix or CVS. As you enter this very private End Unit #1A, you're greeted by Direct and Unobstructed Gulf and beach views as far as the eye can see. Unit #1A has been extensively updated over the last few years, featuring an open kitchen with a huge island, updated cabinets and countertops, and gorgeous porcelain tile flooring. 350' of direct and private beach frontage! This unit is offered Turnkey-Fully Furnished with very tasteful furniture that you'll actually want to keep. Sea Gate Club condos are comprised of 89 units, spread across 15 floors. The building has been extensively updated over the past few years. Recent updates include a new pool and hot tub, new roof, newer hurricane rated windows, newer exterior stucco and paint, new elevator doors, climate-controlled bike storage, and paddleboard/kayak storage. Now is the perfect time to buy in this beautiful building, as there are NO current or pending assessments! Hurry before it's gone, this one is beautiful.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Robert Delaney (941-315-3185)
4621 GULF OF MEXICO DR #14F, LONGBOAT KEY, FL 34228
$710,000205 Days on yellowkey MLS ID: A4664627
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 900 Built: 1973 Tax: $11,151 (2025)Community: Casa Del MarCondo
Taxes:$11,151
Remarks: Investment Opportunity with low HOA fees! Beautifully updated and decorated two-bedroom, two-bath unit with vaulted ceilings can sleep up to 6 at Casa Del Mar on Longboat Key. Casa Del Mar is a popular beach resort with short-term rentals located directly on the Gulf. Use the condo for your own vacation and enjoy all Longboat Key has to offer while collecting income the rest of the year. This turnkey furnished condo is tiled throughout and offers views of the tropically landscaped courtyard and partial Gulf views from the extended living area. The primary ensuite bedroom is furnished with a king size bed and built-in cabinetry. The guest bedroom is furnished with 2 twin beds, built-in cabinetry with a full bath in the hallway. The kitchen has stone counters, solid wood cabinets and stainless appliances. Community amenities include a huge 30’ x 60’ gulf front heated pool, grill area, tennis, pickleball and basketball. Complimentary beach lounges are provided for guests and umbrella rentals are available. Casa Del Mar’s on-site management handles year-round bookings along with all the details so you can enjoy your investment stress-free. Annual gross income for #14F: 2023 $45,131, 2024 $59,833, and 2025 $56,388. Great location convenient to St Armand’s Circle with shops, fine and casual dining, and entertainment and a short drive over the bridge to the southwest cultural hub of downtown Sarasota.
Listing Agent: Ian Addy, Pa (941-961-8850)
1211 GULF OF MEXICO DR #709, LONGBOAT KEY, FL 34228
$1,749,00016 Days on yellowkey MLS ID: A4686985
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1827 Built: 1985 Tax: $14,725 (2025)Community: PromenadeSpa: YesCondo
Taxes:$14,725
Remarks: Set on the 7th floor of the Promenade on Longboat Key, this 2BR/2BA residence offers more than 1,800 square feet of living space with sweeping sunset views across the Gulf, stretching to Sarasota Bay and beyond. From the moment you step into the private entry foyer, the home opens to a light-filled interior where water and sky are always in view. Neutral tones and tile flooring create a clean, comfortable backdrop throughout, while the split floor plan provides privacy for both the primary and guest suites. The combined living and dining areas are oriented toward the Gulf, with a striking corner of windows and sliding glass doors that frame the shoreline, the community pool below, and the bay in the distance. The terrace naturally extends the living space—an ideal spot to unwind and take in the changing colors of the evening sky. The kitchen is spacious and thoughtfully designed, with stone countertops, detailed tilework, stainless steel appliances, and a casual eat-in area positioned to enjoy the view. A separate dining area, complete with a wine refrigerator, offers flexibility for both everyday meals and entertaining. The primary suite is generously sized, featuring a full wall of glass with direct terrace access. Two large walk-in closets provide ample storage, and the bath includes a soaking tub, glass-enclosed shower, and dual vanities. The guest bedroom enjoys its own views of both the Gulf and the bay, along with an en suite bath for added comfort. Additional highlights include an in-residence laundry room, secure building access, and one under-building parking space. Residents of the Promenade enjoy a full-service lifestyle with concierge, 24-hour security, a newly renovated lobby and common areas, two fitness centers, club rooms, four Har-Tru tennis courts, a heated lap pool, spa, and nearly 400 feet of beachfront. The location offers easy access to the shops and dining of St. Armands Circle, blending convenience with a relaxed coastal setting. Membership to the Longboat Key Club is optional and available to residents, offering access to an array of resort-style amenities. These include 45 holes of championship golf, award-winning tennis facilities, a full-service spa and fitness center, multiple waterfront dining venues, a private beach club, marina, and a calendar of social events and activities.
2045 GULF OF MEXICO DR #M1-502, LONGBOAT KEY, FL 34228
$469,500124 Days on yellowkey MLS ID: A4675820
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 928 Built: 1974 Tax: $6,201 (2025)Community: Seaplace IiCondo
Taxes:$6,201
Remarks: A perfect coastal retreat located in Seaplace, and now at an unbeleivable price! This is one of Longboat Keys most desirable beachfront communities. A light and bright 2 bedroom, 1 plus bath, 5th floor condo with a beautiful Bay view. (the photos of the view just do not do it justice!) An exceptional location in the highly sought-after Gulf-front M1 building means you can have your toes in the sand in mere moments. It is beautifully turn-key furnished and meticulously maintained and is ready for its next appreciating owner. The large primary bedroom has its own private ensuite portion of the bath with a sink that can be shut off from a full bath, making it what one would call a 1 bath PLUS. The 2nd bedroom offers a perfect spot for visitors to help you enjoy this amazing way of life to the fullest. Seaplace offers resort style living with unmatched amenities that include 2 large pools and hot tubs; a kiddie pool; 3 har-tru tennis courts; a recently renovated Gulf-front clubhouse; a fitness center; library; gas grills; a one-mile paved walking path surrounding the lush 42-acre property, and a gatehouse with 24-hour security. Located near the newly opened St.Regis Resort, St.Armands Circle and the cultural epicenter of downtown Sarasota, you’ll be close to world-class restaurants, hotels, entertainment, arts, culture, and shopping. Come see this fabulous condo soon and make your island living dream a reality in 2026!
554 SPANISH DR S, LONGBOAT KEY, FL 34228
$435,00020 Days on yellowkey MLS ID: A4688632
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1326 Built: 1971 Tax: $2,179 (2025)Community: Spanish Main Yacht Club CondoCondo
Taxes:$2,179
Remarks: Welcome to Spanish Main Yacht Club waterfront community and your new home! Light and bright, this stand-alone villa is all new and beautifully updated in 2026. White marble-like large porcelain tile floors that span the entire living area, providing a continuous flow throughout the villa. The new kitchen boasts stainless steel appliances, white quartz countertops, new cabinetry, lighting and more. Attractive updates in the primary en suite bedroom and guest bath as well. A nice added feature is the spacious interior laundry room. Beautiful, lush backyard view with privacy and an extra brick paver side yard and outdoor space. A short stroll to the privately deeded beach entrance to gorgeous Gulf beaches. Two minutes to have your toes in the soft, pearly sand. This is a boater’s paradise with slips available for an extremely inexpensive lease and direct access to Sarasota Bay, the Intracoastal waterway and azure waters of the Gulf. Only a short drive to the fantastic shops, restaurants and cultural events Sarasota and St. Armands Circle have to offer. This is a great investment opportunity and chance to enjoy Longboat Key living. The community is in the build-back stage due to damage from hurricanes in 2024 and is almost complete. All 212 units in Spanish Main are under FEMA requirements, guidelines, and stringent adherence to rebuild specifications and inspections from Town of Longboat Key. This is an opportunity to continue to make this villa your custom home.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Kimberly Freiwald (941-256-6775)
100 SANDS POINT RD #114, LONGBOAT KEY, FL 34228
$2,100,00047 Days on yellowkey MLS ID: A4685212
3 Days Off yellowkey (back on 4/6/2026)
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2094 Built: 1966 Tax: $14,826 (2025)Community: Sands PointSpa: YesCondo
Taxes:$14,826
Remarks: Completely updated and offered furnished, this spectacular direct Gulf-front residence at Sands Point delivers the rare combination of expansive living space, modern design, and immediate beach access. True three-bedroom, three-bath Gulf-front residences are seldom available in this sought-after Longboat Key community, making this nearly 2,100-square-foot getaway a standout opportunity. This residence has undergone an extensive renovation that reimagines the interior with a bright, open layout designed to showcase panoramic Gulf views. Floor-to-ceiling glass sliders and expansive windows frame the turquoise waters and sugar-white shoreline beyond, while opening directly to the beachfront patio—placing the sand and surf just steps from your door. Major improvements throughout the residence include impact windows and sliders, new drywall, updated electrical and plumbing systems, newer ductwork, and a new HVAC system—creating a move-in ready coastal retreat where every detail has already been thoughtfully addressed. Inside, the thoughtfully redesigned interior blends coastal comfort with modern finishes. Wide-plank porcelain tile flooring with a warm wood finish flows throughout the residence, connecting each space with a clean contemporary aesthetic. The open great-room layout seamlessly links the chef’s kitchen, dining area, and living room, creating a welcoming environment for entertaining or relaxed beachfront living. The gourmet kitchen serves as the centerpiece of the home, featuring an oversized waterfall-edge island with dine-in seating, custom cabinetry, quartzite countertops, striking Sea Glass tile backsplash, and high-end stainless steel appliances. With the kitchen positioned to overlook the living area and Gulf beyond, every gathering benefits from a dramatic waterfront backdrop. The primary suite occupies the south side of the residence, offering privacy, tranquil water views, and a spacious walk-in closet. Its spa-inspired quartzite bathroom includes dual sinks and a large walk-in shower designed with modern finishes. Two guest bedrooms are arranged on the north side of the residence, each with access to beautifully updated quartzite bathrooms, providing comfort and privacy for visitors. The residence also includes a covered parking space conveniently located just outside the front door. Sands Point is a private Gulf-front enclave located behind the gates of the prestigious Longboat Key Club. Residents enjoy a relaxed resort setting with a beachfront geothermal-heated pool and spa, private clubhouse, shaded tiki huts along the shoreline, and beautifully maintained grounds. A short stroll leads to the community marina, where boat slips are available on a waitlist basis. Positioned on the southern end of Longboat Key, this location places you minutes from championship golf and tennis at the Longboat Key Club, the boutiques and restaurants of St. Armands Circle, and the vibrant arts and dining scene of downtown Sarasota. From boating and beach walks to waterfront dining and cultural events, this exceptional residence offers effortless access to the best of the Gulf Coast lifestyle.
3500 GULF OF MEXICO DR #104, LONGBOAT KEY, FL 34228
$649,00099 Days on yellowkey MLS ID: A4675727
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1486 Built: 1980 Tax: $5,798 (2025)Community: Buttonwood CoveCondo
Taxes:$5,798
Remarks: Major Price Reduction – Seller Says It’s Time to Sell! Rarely available 3-bedroom, 2.5-bath condo in Buttonwood Cove on Longboat Key, just steps across the street from deeded beach access to the beautiful Gulf of Mexico. This light-filled unit is right across the road from the Gulf with peekaboo views from the front guest bedrooms and full peaceful bay views from all living areas and owners bedroom, creating the perfect island setting from sunrise to sunset. The spacious layout includes an open living and dining area, a private Gulf-facing lanai, and three generously sized bedrooms, providing plenty of room for family and guests. Buttonwood Cove is a boutique waterfront community of only 56 residences offering resort-style amenities including a heated pool, tennis and pickleball courts, fishing pier, kayak launch, and boat docks. Recent community improvements include newer roof, elevators, driveways, exterior paint, and Trex docks, and the association is up to date on milestone inspections. Under-building parking, private storage, and deeded beach access with chairs provided make island living easy. Located just minutes from St. Armands Circle, Longboat Key Club, downtown Sarasota, and SRQ Airport, this is a fantastic opportunity to own a spacious 3-bedroom beachside condo on Longboat Key at a newly reduced price. Seller is motivated — schedule your showing today.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Samantha Kotlik (941-447-2175)
4234 GULF OF MEXICO DR #J1, LONGBOAT KEY, FL 34228
$599,00041 Days on yellowkey MLS ID: A4685764
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1150 Built: 1973 Tax: $2,273 (2025)Community: Pelican Harbour & Beach ClubCondo
Taxes:$2,273
Remarks: Go and Show! Renovated - Waterfront - Pet-Friendly - Discover relaxed coastal living in this beautifully renovated two-bedroom, two-bath bayfront condominium positioned to capture stunning sunrise views over the water. With an open floor plan and expansive bay views from the great room, this residence blends comfort, style and the best of waterfront living. The updated interior features porcelain tile flooring throughout, a bright and airy living space, and a bayfront lanai where you can start your mornings watching the sun rise over the water. The kitchen is equipped with new appliances, and the home also includes in-unit laundry for everyday convenience. Recent improvements provide peace of mind, including a new air-conditioning system, new water heater and hurricane-rated doors. The spacious primary suite offers a private en-suite bath, while the guest suite enjoys direct access to the second bath, creating an ideal layout for family and friends. The condominium is nicely furnished, making it move-in ready. Residents enjoy a full range of resort-style amenities, including private beach access, community pool, tennis courts, pickleball courts, boat docks accommodating vessels up to 28 feet, a clubhouse, organized social activities, bike storage, kayak storage and launch, and on-site maintenance. The well-maintained association has completed numerous recent upgrades, such as new roof, hurricane-rated carports, new docks, freshly painted buildings, and newly re-surfaced tennis and pickleball courts, ensuring long-term value and appeal. You'll also appreciate the association's pet-friendly policy. Association fees include building and flood insurance, cable, water, sewer, trash, escrow reserves, and comprehensive grounds and building maintenance, offering low-maintenance ownership. In a desirable mid-key location, this property is ideal for enjoying the best of island life with exceptional boating, kayaking, and easy access to the bay and Gulf. Whether you’re looking for a full-time residence, seasonal retreat or investment opportunity, this bayfront condominium delivers the ultimate Florida waterfront lifestyle.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Michael Seamon (941-586-1802)
4350 CHATHAM DR #205, LONGBOAT KEY, FL 34228
$259,90075 Days on yellowkey MLS ID: A4681134
0 Days Off yellowkey (back on 4/4/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 667 Built: 1969 Tax: $4,627 (2024)Community: Longboat HarbourCondo
Taxes:$4,627
Remarks: Under contract-accepting backup offers. Resort-style living at Longboat Harbour! This move in ready one bedroom, one bath condo is one of the best get-aways in the area. From your lanai, the serene view down the canal makes for a great place to have your morning coffee or enjoy a sunset cocktail. Steps away, you have private gated access to the Gulf beaches including a pavilion with washrooms, lockers and parking. If you like, this condo can be an incredible investment opportunity, earning rental income from day one. In 2025 the A/C unit was replaced, water heater 2023. In 2025, all the roofs were replaced, along with the elevators in Building E. There is private storage, assigned covered parking, and plenty of guest parking. The pool nearest you has been resurfaced and new pavers added throughout the complex. Longboat Harbour is a friendly community with numerous amenities and an on-site management team. It boasts four heated pools, tennis and pickleball courts, putting green, and kayak storage with launch. For boating enthusiasts, slips are available for powerboats and sailboats up to 34 feet on a first-come, first-served basis. At the clubhouse there is a fully equipped gym (with sauna and lockers) and the renovated community room overlooking the bay hosts many social occasions and private parties. Whether for a warm winter getaway, year-round residence or investment opportunity, Longboat Harbour is resort-style living at its best!
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Tracey Fiedler (303-809-2582)
2450 HARBOURSIDE DR #244, LONGBOAT KEY, FL 34228
$2,450,00019 Days on yellowkey MLS ID: TB8491404
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 3083 Built: 1990 Tax: $20,065 (2025)Community: Marina BayCondo
Taxes:$20,065
Remarks: Welcome to Marina Bay – the premier condominium within the gated Bay Isles Community on Longboat Key. This exceptional corner residence spans 3,578 sq ft of sunlit, sophisticated living, and shares it fourth floor lobby with only one other unit. The large, updated kitchen/dining room features extra-large windows allowing for an unobstructed view of Sarasota Bay. Exquisite floor-to-ceiling windows, in the oversized living room, frame sweeping panoramic vistas of Sarasota Bay and downtown Sarasota, while the unusually large balcony provides the perfect setting for morning coffee, evening relaxation, and observing abundant bird and marine life. A second, west-facing balcony delivers spectacular Gulf sunsets, offering the rare pleasure of both sunrise and sunset living. Marina Bay is the epitome of resort-style living, with a heated pool and spa, newly renovated tennis and pickleball courts, and well-appointed fitness room. Head to the adjacent marina or around the manicured Longboat Key Club Harbourside Golf Course. Ideally situated, this residence is in close proximity to Publix, CVS, Chase Bank, and local shops. Whether as a refined full-time residence or an elevated part-time retreat, this rare offering delivers unmatched luxury, convenience, and island living. Key Features include: Corner-end unit with 3 bedrooms and 3 ½ newly renovated baths, A walk-in double shower in main suite, New floor tile on oversized screened balcony, bathrooms, and main suite floors, Equipped with storm shutters, and access to private beach for Bay Isles residents only.
Listing is courtesy of: REDFIN CORPORATION (617-458-2883)
Listing Agent: Steven Weiss (845-242-5473)
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