Location: Longboat Key , 34228
Do Not Show Listings
651 BROADWAY ST, LONGBOAT KEY, FL 34228
$2,795,000156 Days on yellowkey MLS ID: A4672952
2 Days Off yellowkey (back on 3/19/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3320 Built: 2003 Tax: $26,362 (2025)Community: Longbeach On Longboat KeySpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$26,362
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2025
Middle School: Martha B. King Middle
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)
509 SPANISH DR N, LONGBOAT KEY, FL 34228
$369,00014 Days on yellowkey MLS ID: N6143864
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1357 Built: 1967 Tax: $6,955 (2024)Community: Spanish Main Yacht Club CondoVilla
Taxes:$6,955
Tax Year: 2024
Remarks: STEPS FROM THE BEACH.....WATERFRONT COMMUNITY......DEEDED BEACH ACCESS......FULLY RENOVATED..........IMPACT WINDOWS..........COMMUNITY POOL...........Just **432 steps from the beach**, this is where coastal living stops being a dream and becomes your daily rhythm. Morning walks on soft sand, sunset returns under glowing skies, and the constant sense that the water is always just around the corner. **Fully renovated and never lived in**, this Longboat Key retreat feels brand new in every way — a clean, beach-inspired design with effortless flow and natural light throughout. Featuring **quartz countertops, impact windows, and a brand new water heater**, every detail has already been perfected so you can arrive and immediately exhale. Set within a **quiet waterfront community with deeded beach access**, life here feels unhurried and private, yet connected to everything that defines coastal luxury. From **boating access and a nearby pool** to the walkable, relaxed atmosphere residents cherish, it’s a setting designed for ease, not effort. With your own **covered parking and driveway**, and just minutes to **St. Armands Circle, Sarasota, and Anna Maria Island**, you’re positioned in one of the most desirable corridors on the Gulf. This is the rare combination buyers wait for — **newly finished, never occupied, and this close to the shoreline** — where every day feels like a quiet escape, and every return home reminds you why you chose it.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Garrett Sedlacek (913-461-6882)
3240 GULF OF MEXICO DR #B104, LONGBOAT KEY, FL 34228
$475,00017 Days on yellowkey MLS ID: A4688243
REDUCED by $20,000 (4.0%) on 04/22/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1975 Tax: $4,538 (2025)Community: PortobelloCondo
Taxes:$4,538
Elementary School: None
High School: None
Middle School: None
Remarks: Experience tranquil island living in this beautifully maintained first-floor residence at Portobello, offering private, serene views of expansive grounds, lush mangroves, and the bay. With your beach, shimmering Gulf waters, and breathtaking sunsets just across the street, this is the perfect coastal retreat. Designed with a desirable split floor plan, the home is filled with natural light from sliding glass doors that span the width of the residence. The large screened-in lanai is accessible from the living area and both bedrooms—seamlessly blending indoor and outdoor living while overlooking a generous grassy yard space and peaceful bayou, perfect for canoeing and kayaking right from your backyard. The kitchen features granite countertops and stainless steel appliances. Offered turn-key and fully furnished, this residence is move-in ready and ideal for seasonal or full-time living. Portobello is a sought-after Beach-to-Bay community ideally located mid-Key, offering an exceptional array of amenities including 600 feet of private beach frontage and 260 feet along the bay. Residents enjoy a heated community pool, tennis courts, clubhouse, BBQ and picnic areas, fishing pier, and kayak launch. Just minutes from the world-class shopping and dining of St. Armands Circle and everything Sarasota has to offer, this exceptional residence invites you to experience the pinnacle of Longboat Key living—where every day feels like a vacation.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Laura Rode (941-724-9957)
7030 POINSETTIA AVE, LONGBOAT KEY, FL 34228
$995,00038 Days on yellowkey MLS ID: A4686787
REDUCED by $104,000 (9.5%) on 04/23/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1402 Built: 1934 Tax: $6,672 (2025)Community: Longbeach On Longboat KeySpa: YesSingle Family
Taxes:$6,672
Remarks: Enjoy as an investment opportunity or your own private retreat in the highly desirable Village neighborhood on the north end of Longboat Key, with no HOA fees and convenient Gulf Beach and Sarasota Bay access. Set on an oversized lot, the property includes a main residence and a separate guest cottage connected by an inviting breezeway, creating excellent flexibility for seasonal use or extended stays. Each space offers privacy and comfort, enhancing overall livability and guest experience. This turnkey furnished property has been thoughtfully restored to preserve its historic charm. Key updates include a metal roof, impact windows, new cabinetry, and updated appliances, providing both character and peace of mind. The main home welcomes you with an enclosed front porch and a warm, inviting living area complete with a wood-burning fireplace, pine wood flooring, and shiplap accents. The updated kitchen features striking countertops and extended workspace perfect for entertaining, with direct access to a private courtyard deck shaded by a majestic tree. The primary bedroom offers vaulted ceilings and a large walk-in closet. The primary bathroom is also tastefully updated. The guest cottage includes its own entrance, ensuite bathroom, private patio, and full kitchenette, making it well suited for guest accommodations or extended stays. Outdoor amenities further enhance the property’s appeal. A covered entertaining area overlooks the pool and spa within a screened lanai, complemented by a well-appointed covered outdoor kitchen. The spacious paver patio and lush tropical landscaping create a private resort-style setting that appeals to long-term or seasonal residents and guests alike. The oversized lot provides ample parking, including space for a boat or golf cart, an added benefit in this beach to bay community. With convenient access to a boat ramp, nearby beaches, waterfront dining and local shops, this charming neighborhood enjoys strong demand. Turnkey and ready to enjoy or generate annual or seasonal rental income, the seller is open to offers.
677 LANDS END DR, LONGBOAT KEY, FL 34228
$2,790,00070 Days on yellowkey MLS ID: A4682565
REDUCED by $60,000 (2.1%) on 04/18/2026
Bed: 3 Bath: 3.0 Gar: 4 Liv Area Sq Ft: 4182 Built: 1989Monthly Fee: $967 Tax: $33,361 (2025)Community: Lands EndSpa: NoSingle Family
Taxes:$33,361
Middle School: W.D. Sugg Middle
Remarks: In a rich tropical waterfront setting on Longboat Key, this unique retreat lives like a modern treehouse while evoking a sense of peace, family and comfortable, easy island living. Tucked within the island’s native landscape along a natural bayou off Sarasota Bay, the property offers a rare opportunity to experience serene waterfront living surrounded by nature, with the Gulf’s azure waters and pristine beach access just moments away. Enjoy your private backyard dock and kayak launch or secure your boat on one of the deepwater slips on the open bay. Excellent fishing and bird watching await right outside your door in this remarkable natural habitat. The spacious home is anchored by a stunning great room with vaulted cedar ceilings and exposed beams. The home features a 40-by-9-foot sunroom with bar area and handcrafted art shelves, a dedicated library, an inviting family room and a separate private office with extensive built-in cabinetry, providing warmth and functionality. Extensive decking spans the front entry and wraps around an inner atrium courtyard for alfresco dining. An elevated cabana-style shaded area invites relaxation in sun and shade. The kitchen with center island is positioned for hosting memorable gatherings. The primary suite offers a full wall of windows overlooking the tranquil bayou, two walk-in closets and an additional wall of custom storage. The split floor plan provides a separate wing for guests, featuring two additional bedrooms and baths for convenient hosting. Each guest room offers private access to the outdoor decks and views of the tropical center atrium. Two garages accommodate up to four vehicles, boats, golf carts or paddleboards. Many of the furnishings are included. In Land’s End, an intimate gated community of just 12 residences, owners enjoy maintenance-free landscaping, a heated pool, tennis and pickleball courts, and convenient deepwater boat slips, all artfully tucked among the trees for privacy. From here, it is a short visit or golf cart ride to the captivating sandy Gulf beach or local favorites, including Shore Longboat Key, Mar Vista Dockside Restaurant and Whitney’s. The adjacent plaza also offers multiple popular waterfront cafes, boutique shops, Ventura’s restaurant, and 24/7 gym or Pilates studio. Enjoy mesmerizing sunsets on the Gulf or sunrises on the bay from this waterside community. This is a rare offering in today’s marketplace, capturing the allure of Old Florida living in one of the island’s treasured enclaves.
5311 GULF OF MEXICO DR #5, LONGBOAT KEY, FL 34228
$799,0003 Days on yellowkey MLS ID: A4691314
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1110 Built: 1973 Tax: $3,363 (2025)Community: Mccalls Beach CastleSpa: YesCondo
Taxes:$3,363
Remarks: Turnkey furnished and positioned just steps from the Gulf’s sandy shoreline, this first-floor residence at Beach Castle on Longboat Key offers a compelling combination of coastal living and proven rental potential. With flexible daily or weekly rental allowances, this two-bedroom retreat presents an exceptional opportunity for personal use, income generation, or both. The light-filled interior features an open layout designed for ease and comfort, where the kitchen, dining, and living areas flow together naturally. Oversized tile flooring, updated impact glass, and sliding doors enhance both durability and livability, while the kitchen is well-appointed with granite countertops, solid wood cabinetry, stainless steel appliances, and built-in shelving—creating a functional space for everyday living or hosting. Floor-to-ceiling sliders lead to a private patio and screened lanai, offering a seamless transition to the outdoors and placing you just moments from the beach. The split-bedroom plan provides added privacy, with the primary suite enjoying direct access to the outdoor space, while the guest bedroom is comfortably sized with its own en-suite bath. Set within the boutique Beach Castle community, residents enjoy a unique beach-to-bay lifestyle with deeded Gulf access, a heated swimming pool and spa, grilling areas, and a fishing pier with day dock on Sarasota Bay. Lush landscaping and well-maintained grounds create a relaxed, resort-style setting that enhances both owner enjoyment and guest appeal. Located on the desirable north end of Longboat Key, this property is just minutes from Bayfront Park, Cedars Tennis Resort, and the island’s scenic biking and walking paths. A short drive south brings you to the Longboat Key Club, St. Armands Circle’s dining and boutiques, and downtown Sarasota’s renowned cultural venues, waterfront parks, and year-round events. With strong rental history, immediate beach access, and a turnkey presentation, this Beach Castle residence offers a rare opportunity to enjoy the best of Longboat Key—whether as an investment, a private getaway, or a combination of both.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Roger Pettingell (941-387-1840)
531 WEDGE LN, LONGBOAT KEY, FL 34228
$2,599,99925 Days on yellowkey MLS ID: A4687694
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2751 Built: 1966Monthly Fee: $21 Tax: $10,602 (2025)Community: Country Club Shores Sec 02Spa: NoSingle Family
Taxes:$10,602
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: A seamless blend of refined design and waterfront living defines this beautifully updated canal-front residence in Country Club Shores. Expanded from its original ranch design, the home offers approximately 2,700+ square feet of thoughtfully curated space, featuring four bedrooms, including dual primary suites on both the first and second levels—an ideal layout for guests or multi-generational living. Each bathroom is finished with timeless, elegant details that elevate the home’s overall sense of sophistication. A comprehensive 2018 renovation introduced elevated style and modern functionality, anchored by a stunning chef’s kitchen appointed with Thermador appliances, built-in refrigeration, and a generous island. Just beyond, an expansive butler’s pantry and secondary prep kitchen enhance both convenience and flow, creating an effortless environment for everyday living and entertaining. Natural light fills the interiors, drawing attention to tranquil canal views and soft glimpses of the bay from the den. The upstairs primary suite serves as a private retreat, complete with its own balcony overlooking the water—an inviting setting for quiet mornings and sunset evenings. Outdoors, a private, low-maintenance setting unfolds with a sparkling pool and beautifully updated waterfront features, including a newer dock, seawall, and 24,000 lb boat lift. Additional highlights include hurricane-impact windows and doors, classic plantation shutters, and 2022 air conditioning systems—completing this exceptional offering in one of Longboat Key’s most desirable waterfront communities. Ideally located just moments from St. Armands Circle, with its renowned dining and boutique shopping, this residence offers a lifestyle of effortless coastal sophistication.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Kerry Mccarthy (720-233-7147)
448 GULF OF MEXICO DR #A205, LONGBOAT KEY, FL 34228
$629,0005 Days on yellowkey MLS ID: A4690875
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1306 Built: 1970 Tax: $5,089 (2025)Community: Bay HarbourCondo
Taxes:$5,089
Remarks: Set within an intimate 39-residence waterfront enclave, this Bay Harbour retreat captures the essence of refined island living. Framed by swaying palms and 720 feet of shimmering Sarasota Bay frontage, the community feels like a private tropical sanctuary, where beautiful sunrises paint the sky and waterfowl dive gracefully for fish along the shoreline. Boaters will appreciate the ideal marina location, offering a quick, scenic ride to the Gulf of Mexico. The marina is fully equipped with electrical service, fresh water and a fish-cleaning station, while the seawall provides front-row views of dolphins and playful manatees. A kayak launch adds even more ways to enjoy life on the water. Inside, this spacious two-bedroom, two-bath residence spans 1,300-plus square feet of light-filled living with captivating views of Bay Harbour Marina and Sarasota Bay. Both bedrooms feature walk-in closets, and the kitchen blends style and function with wood cabinetry with glass fronts, stainless-steel appliances, solid-surface countertops and tile flooring throughout. The generous primary suite offers an en-suite bath and a peaceful vantage point overlooking the turquoise bay waters. Offered furnished, the home includes an in-unit washer and dryer, covered assigned parking, ample guest parking and elevator access. Bay Harbour’s amenities elevate the experience with a heated pool, grilling area and first-come boat slips accommodating vessels up to 42 feet. Owners may have one pet. Positioned in south Longboat Key, you’re just 15 minutes from downtown Sarasota, home to upscale shopping, acclaimed dining, galleries, theater, opera, ballet and vibrant arts scene. And for everyday indulgence, you can visit or bike to St. Armands Circle, a beloved destination of boutiques, cafés and coastal charm.
Listing Agent: Kathleen Wingate (813-731-3332)
3806 GULF OF MEXICO DR #C312, LONGBOAT KEY, FL 34228
$320,0008 Days on yellowkey MLS ID: A4690206
0 Days Off yellowkey (back on 4/25/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1062 Built: 1970 Tax: $3,659 (2025)Community: Beach Harbor ClubCondo
Taxes:$3,659
Remarks: LONGBOAT KEY 2-bedroom, 2-bathroom end-unit condo offering a coastal lifestyle with convenient access to both the Gulf of Mexico and Sarasota Bay. This third-floor corner unit is filled with natural light, turnkey furnished and offers added privacy with no unit above. Interior features include a welcoming foyer entry and a flexible second bedroom with a retractable partition and Murphy bed, ideal for guests or a multipurpose space. Tile flooring runs throughout for easy maintenance. The HVAC system was replaced in 2024. The building provides secure entry and an assigned covered carport. Beach Harbor Club is a waterfront community spanning approximately 5.3 acres on Longboat Key, consisting of 133 units and uniquely positioned between the Gulf of Mexico and Sarasota Bay. Residents enjoy deeded beach access with showers, umbrellas, and beach chairs, along with bayfront amenities including a seawall, fishing areas, and newly constructed boat slips. Community features include an oversized heated swimming pool, clubhouse, fitness center, shuffleboard courts, outdoor cooking and grilling areas, kayak launch and storage, guest parking, additional storage, and on-site management. This community supports an active coastal lifestyle with opportunities for boating, kayaking, fishing, and beachgoing. The property is located near Bayfront Park with tennis facilities and is convenient to nearby shopping and everyday essentials.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Greg Hudson (941-302-1485)
510 WEDGE LN, LONGBOAT KEY, FL 34228
$1,990,000199 Days on yellowkey MLS ID: A4668133
5 Days Off yellowkey (back on 4/25/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1840 Built: 1967Monthly Fee: $17 Tax: $14,551 (2024)Community: Country Club Shores Sec 02Single Family
Taxes:$14,551
Remarks: Under contract-accepting backup offers. Welcome to your own piece of paradise in the prestigious Country Club Shores community on Longboat Key. This completely renovated 4-bedroom, 3-bath coastal retreat was taken down to the studs in 2012 and rebuilt with exceptional attention to detail—offering the rare combination of timeless style, modern infrastructure, and effortless move-in readiness on a tranquil canal. From the ground up, every major system has been upgraded for peace of mind: new water and sewer lines, updated electrical throughout, impact-rated doors and windows, a resurfaced saltwater pool and with new pool heater. Newer seawall and dock, gas that was run to the house with no propane tank to worry about. No component was overlooked. The result is a home that lives like new yet radiates refined coastal charm, with most of the beautifully curated furnishings remaining with the property. Inside, you’ll be welcomed by a bright, open-concept design featuring beautiful, engineered wood floors, custom beadboard ceilings, with beams, elevated ceiling heigh in the main living room and a soothing palette of sea-glass blues and clean whites. The heart of the home is a gourmet kitchen outfitted with stainless steel appliances, designer pendant lighting, and stylish lattice-front cabinetry. A large island anchors the space, perfect for entertaining, while the adjacent living area boasts custom-built-ins, a sleek gas fireplace, and expansive views that flow effortlessly outdoors. Each bedroom is designed for comfort and privacy, with spa-inspired bathrooms that feature elegant tile work, modern fixtures, and soft lighting. The primary suite is a retreat of its own, with custom shelving, cozy window seats, and lush garden views through plantation shutters. Step outside to experience Florida living at its finest. The spacious screened lanai surrounds a sparkling heated saltwater pool and paved deck, creating a private oasis perfect for lounging, swimming, or dining alfresco in total comfort. Just beyond, a large, newer dock awaits, offering deep-water canal access—an ideal setup for avid boaters and water lovers. The deck overlooking the canal is a peaceful setting for morning coffee or an evening cocktail This home also offers exclusive deeded beach access, just a short walk or bike ride away, where you can soak in the soft white sands and turquoise waters of the Gulf. When it’s time to explore, the renowned boutiques and fine dining of St. Armands Circle are just down the street, offering vibrant nightlife, unique shopping, and gourmet experiences in a picturesque coastal setting. A short drive over the scenic Ringling Bridge takes you to downtown Sarasota, a cultural haven known for its art galleries, theaters, opera house, and waterfront dining. Whether you're strolling through the Saturday farmers market, taking in a performance at the Sarasota Opera, or enjoying waterfront cocktails at Marina Jack, the city provides an enriching blend of sophistication and coastal charm. With its ideal location, timeless design, and luxurious updates, this home offers the very best of Longboat Key living—a rare opportunity to enjoy both boating and beachside leisure in one of Florida’s most coveted communities.
Listing Agent: Courtney Tarantino (941-893-7203)
925 SPANISH DR N, LONGBOAT KEY, FL 34228
$750,0003 Days on yellowkey MLS ID: A4691251
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1449 Built: 1968 Tax: $491 (2025)Community: Spanish Main Yacht Club CondoSpa: NoVilla
Taxes:$491
Remarks: Wow! Panoramic water views from almost every window, plus rare direct access to Bay waters just steps from the back paver patio. This completely renovated 2 bed/2 bath, 1449 sq. ft home is a must see! Fully remodeled in 2025/2026 in full compliance with FEMA requirements. It is all about the details as this gorgeous Spanish Main turn-key furnished villa is ready to welcome you home! The centerpiece of the kitchen is the very large strategically custom designed Quartz island that doubles as a dining table, in a soft color palette that can seat 10. The kitchen features beautiful all wood 42” cabinetry, stainless steel appliances, large undermount sink with a push button garbage disposal, lovely backsplash and lots of storage with an abundant of additional counter space, perfectly designed for entertaining. The villa flows seamlessly with an expansive open floor plan, plank tile flooring in every room plus crown molding that frames each room. The large primary bath has an oversized classically designed walk-in shower created for handicap access with double sinks. The tastefully appointed guest bath has an all-glass enclosed walk-in shower. From guest bath, enter the 9X6 in villa laundry room with new stacked Electrolux washer and dryer. All hurricane grade windows and doors to secure the home from the Florida storms. Custom window shades provide sun mitigation and ultimate privacy. The fully enclosed glass Florida room is a treasure in and of itself with extensive views of Sarasota Bay with a lush backdrop providing total privacy. There is also a built-in office space, large walk-in closet, additional flex space for dining and/or lounging plus a dry bar and wine center which makes this a very useful space. Step outside onto the brick paver patio and lounge, grill and relax with the sound and views of the Bay waters and abundant bird and wildlife. Grab your kayak or paddleboard and launch right from the backyard with direct water access to the open Bay waters. This villa is packed with so many upgraded features with new tile roof in 2019, A/C 2020, and tankless hot water in 2018. The villa is part of the Spanish Main Yacht Club community which has some of the best waters to explore in Sarasota for fishing, sandbar enjoyment, kayaking and swimming right in your own backyard. You have direct access to the Intra-coastal waterway and a quick boat ride to the Gulf of Mexico with restaurants you can get to by boat. The Spanish Main maintenance free- community has a wonderful neighborhood feel with a heated pool overlooking the 40-slip Marina, deeded beach access, with social events galore making every day feel like a vacation as you lounge in the sun and enjoy the sea breeze. Slips are available for very affordable leasing. The deeded beach access is perfect for those numerous beach days and magnificent sunsets. This pet-friendly very active 55+ community are added benefits for your enjoyment. Located only a short drive to the fantastic shops and restaurants including Anna Maria Island plus cultural events that Sarasota and St. Armand’s Circle have to offer.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Kimberly Freiwald (941-256-6775)
350 GULF OF MEXICO DR #234, LONGBOAT KEY, FL 34228
$749,000101 Days on yellowkey MLS ID: A4678529
REDUCED by $150,000 (16.7%) on 04/24/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2513 Built: 1992 Tax: $10,107 (2025)Community: Tangerine Bay ClubSpa: YesCondo
Taxes:$10,107
Remarks: One or more photo(s) has been virtually staged. Set amid the lush, manicured grounds of Tangerine Bay, this exceptional two-story penthouse residence offers a rare blend of architectural volume, natural light, and water views. Mature tropical landscaping, tranquil lagoons, and resort-style amenities create a serene, park-like environment that feels both private and welcoming. Two terraces highlight scenic views and offer the option of installing a gas grill. Inside, soaring two-story ceilings define the main living area, creating an airy, light-filled atmosphere enhanced by expansive windows that frame picturesque views of the lagoon, resort-style pool w/ waterfall features, tropical plantings and the waters of Sarasota Bay and distant city skyline. The open living and dining spaces are ideal for both relaxed everyday living and entertaining, anchored by a fireplace and generous wall space for art. From the entry patio, unexpected Bay and city views provide a striking first impression and a unique urban-meets-coastal backdrop. The residence features three full bedrooms and three and a half baths. The upper-level retreat with its full bath has a terrace with elevated views across the natural preserve toward the city. This home presents a true blank canvas, thoughtfully priced to allow the new owner to reimagine and transform it into their own vision of refined coastal living. A deeded, private two-car garage adds exceptional convenience and value—an uncommon and highly desirable feature. Located on the coveted south end of Longboat Key, Tangerine Bay Club is a gated, pet-friendly community close to Lido Beach, dining and boutique shopping on St. Armands Circle, and the cultural, dining, and arts scene of downtown Sarasota. Optional Bay Isles Beach Club membership is available, providing exclusive access to a private, gated four-acre Gulf of Mexico beach facility, reserved for a select group of members—ideal for beach gatherings, sunset celebrations, and effortless days by the sea. An outstanding opportunity to embrace the Florida lifestyle in one of Longboat Key’s most desirable bayfront communities.
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
5125 GULF OF MEXICO DR #7, LONGBOAT KEY, FL 34228
$975,000178 Days on yellowkey MLS ID: N6141238
0 Days Off yellowkey (back on 4/24/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 961 Built: 1983 Tax: $11,168 (2024)Community: Seagrape InnCondo
Taxes:$11,168
Remarks: Under contract-accepting backup offers. Nestled in the heart of Longboat Key, this exceptional two-bedroom, two-bathroom beachfront condo offers a rare blend of luxury, comfort, and high rental potential. Situated within the meticulously maintained Seagrape Inn, this turnkey furnished unit is an investor’s dream, boasting a potential gross annual revenue of $108,000 and a net operating income of $66,000. The Seagrape Inn's lush landscaping and upscale tropical ambiance create an idyllic setting along the stunning Gulf of Mexico, perfect for both personal enjoyment and income generation. Amenities at Seagrape Inn include a private entrance to each condo, a private heated pool, a private beach area with lounge chairs and umbrellas, on-site laundry and ice machine, upgraded Wi-Fi throughout the resort, cable TV, a gazebo with a gas BBQ grill, and beach towels and linens. Unit 7, perched on the second floor, provides breathtaking views of the ocean and the inviting pool below. Upon entry, the condo exudes sophistication, with a thoughtfully designed living space that seamlessly connects the living room, dining area, and upgraded kitchen. The kitchen, recently renovated to perfection, features new cabinets, countertops, recessed lighting, plumbing fixtures, and state-of-the-art appliances. The entire unit has been enhanced with new waterproof LVP flooring, fresh interior paint, and modern light fixtures, ensuring a contemporary and elegant aesthetic throughout. Both bedrooms are tastefully furnished, offering serene retreats after a day at the beach. The bathrooms have been completely remodeled, showcasing new vanities, tile work, shower doors, and plumbing fixtures. Step onto the screened balcony to savor unparalleled views of the ocean, pool, and lush greenery a perfect spot to relax and soak in the tranquil surroundings. Beyond the condo's exquisite interior, significant exterior improvements have been made, including the installation of hurricane windows and doors, new deck waterproofing, and exterior painting. The convenience of a designated parking spot adds to the property’s appeal. Located in a prime area of Longboat Key, this condo provides easy access to the beach, Gulf, and nearby restaurants and shops. Whether you're seeking a lucrative investment or a luxurious personal retreat, this beachfront condo offers an extraordinary opportunity to experience the best of coastal living in an unparalleled location.
Listing Agent: Patrick Brogley (941-361-9031)
1975 GULF OF MEXICO DR #G4-206, LONGBOAT KEY, FL 34228
$449,000235 Days on yellowkey MLS ID: A4663933
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1068 Built: 1977Monthly Fee: $1,438 Tax: $3,420 (2024)Community: Seaplace IiiSpa: YesCondo
Taxes:$3,420
Remarks: Gated Gulf-front community • Two heated pools & tennis courts • Beach access within minutes Experience coastal living at Seaplace, a gated Gulf-front community on the southern end of Longboat Key. This two-bedroom, two-bath residence (Unit G4-206) features an open-concept layout and a screened lanai overlooking lush tropical landscaping and community green space. Recent improvements include hurricane-rated impact windows and lanai enclosure, providing peace of mind and energy efficiency while enhancing natural light and sound protection. Inside, durable flooring and a neutral color palette create a bright, relaxed atmosphere. The kitchen offers ample cabinetry, and a breakfast bar that opens to the main living area. The primary suite includes a walk-in closet and private bath, while the guest bedroom and full hall bath provide comfortable separation for visitors. A full-size washer and dryer inside the unit adds convenience and functionality. Residents of Seaplace enjoy approximately ½ mile of Gulf beach frontage and an array of resort-style amenities across 42 acres of manicured grounds. Highlights include two heated swimming pools and spas, Har-Tru tennis courts, walking paths, a clubhouse with fitness center, sauna, and library, a playground, and community grilling areas. The on-site management and 24-hour staffed gatehouse provide security and peace of mind in this established coastal community. The quarterly association fee of $4,315 covers exterior maintenance, building insurance, water, sewer, cable, and amenities. Service animals permitted per association rules; no pets otherwise. Seasonal and annual rentals are allowed with a two-month minimum. Seaplace’s location combines tranquility with access to shopping, dining, and cultural attractions. Publix (0.8 mi) and Bayfront Park (1.6 mi) are nearby for groceries, recreation, and pickleball. Enjoy dining at Harry’s Continental Kitchens (1.3 mi), Euphemia Haye (1.1 mi), or The Shore Restaurant (1.9 mi), and explore boutique shopping at St. Armands Circle (3.8 mi). Longboat Key Club Golf & Tennis (2.7 mi) and Downtown Sarasota (6.5 mi) offer golf, marinas, and cultural venues including the Ringling Museum and Selby Gardens. Seaplace residents enjoy direct beach access for sunset walks along the Gulf, tropical courtyards, and a private coastal setting minutes from everything. Whether a seasonal retreat or year-round home, Unit G4-206 blends location, comfort, and quality within a secure, Gulf-front environment on Longboat Key. Includes hurricane-rated windows and lanai enclosure, in-unit laundry, screened lanai, and access to pools, tennis, clubhouse, and Gulf-front amenities. A 3D virtual tour and floor plan viewer are available within the listing for additional detail.
Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
Listing Agent: Michael Renick Pllc (941-400-8735)
2039 GULF OF MEXICO DR #G3-203, LONGBOAT KEY, FL 34228
$499,99924 Days on yellowkey MLS ID: A4688685
REDUCED by $39,001 (7.2%) on 04/15/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1214 Built: 1974Monthly Fee: $1,170 Tax: $5,576 (2025)Community: Seaplace ISpa: YesCondo
Taxes:$5,576
Remarks: Experience the Best of Coastal Living at Seaplace on Longboat Key! Welcome to this beautifully maintained 2-bedroom, 2.5-bath residence offering a perfect blend of comfort, style, and relaxed island living. This spacious two-level layout features an inviting open-concept living and dining area with neutral coastal tones, tile flooring throughout the main level, and seamless access to a private lanai—ideal for enjoying tranquil views and Gulf breezes. The updated kitchen is designed for both functionality and style, showcasing granite countertops, white cabinetry, stainless steel appliances, and a convenient breakfast bar, perfect for casual dining or entertaining. Upstairs, you’ll find two generously sized bedrooms, each offering privacy and comfort. The primary suite serves as a relaxing retreat, while the guest bedroom is ideal for family or visitors. The additional half bath on the main level adds convenience for guests. This residence is offered in move-in ready condition and reflects pride of ownership throughout. Residents of Seaplace enjoy approximately ½ mile of pristine Gulf beach frontage and an exceptional array of amenities across 42 beautifully landscaped acres. Highlights include two heated swimming pools and spas, Har-Tru tennis courts, scenic walking trails, a fitness center, and a clubhouse with kitchen, library, and sauna. Additional features include playground areas, grilling stations, on-site management, and a 24-hour staffed gatehouse for security. Whether you're searching for a primary residence, vacation getaway, or investment opportunity, this home offers the ultimate Longboat Key lifestyle in one of the island’s most sought-after communities. Schedule your private showing today!
2000 HARBOURSIDE DR #1501, LONGBOAT KEY, FL 34228
$790,00050 Days on yellowkey MLS ID: A4684680
REDUCED by $30,000 (3.7%) on 04/24/2026
Bed: 2 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 1370 Built: 1985Monthly Fee: $1,862 Tax: $9,011 (2025)Community: Fairway Bay 2 Ph 2 & 3Spa: YesTownhouse
Taxes:$9,011
Remarks: Behind the gates of Bay Isles, a private country club community, lies an immaculate 2-bedroom, 2-bath end-unit townhouse with a side-by-side 2-car garage plus extra space for hobbies or storage. Upgrades abound: LVP flooring throughout, upgraded ceiling fans, a new dining chandelier, under-cabinet lighting, fresh paint, custom wood trim, new shaker cabinets, countertops, and premium appliances. Beyond the home, you’re steps from Longboat Key Club’s golf, tennis, and marina, and near St. Regis Resort. Sarasota’s best awaits: walk to the beach, St. Armands, and Anna Maria. Plus, enjoy fishing, boating, and all the water adventures Sarasota offers!
Listing is courtesy of: DEVELOPERS REALTY LBK, INC (941-799-9096)
Listing Agent: Reid Murphy (941-232-3304)
1591 GULF OF MEXICO DR #216, LONGBOAT KEY, FL 34228
$2,750,000221 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
High School: Sarasota High
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.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Lynn Morris, Pllc (941-400-4526)
65 LIGHTHOUSE POINT DR, LONGBOAT KEY, FL 34228
$7,445,000133 Days on yellowkey MLS ID: A4674851
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4921 Built: 2001Monthly Fee: $617 Tax: $45,712 (2024)Community: Lighthouse PointSpa: YesSingle Family
Taxes:$45,712
Remarks: Longboat Key Waterfront Estate Lifestyle Unrivaled in privacy, craftsmanship, and waterfront lifestyle, this gated Lighthouse Point residence lives like a grand coastal estate, with 4 Bedrooms, 4-1/2 Baths, and nearly 5,000 square feet of refined interiors opening to sweeping terraces on two levels and serene views over a secluded, bridgeless-access lagoon leading directly to the Gulf of Mexico. Extensively renovated in 2021, the two-story Mediterranean-inspired home blends timeless architecture with a sophisticated contemporary aesthetic, framed by manicured tropical grounds on over one-third of an acre in one of Longboat Key’s most exclusive enclaves. Dramatic Arrival & Entertaining Spaces A soaring central foyer with coffered tongue-and-groove ceiling, arched French casement doors, and an elegant wraparound catwalk establishes a dramatic sense of arrival while capturing water, sky, and lush landscaping in every direction. The main living area is designed for effortless entertaining, with a sleek wood-and-stone feature wall, modern fireplace, and sculptural Tom Dixon lighting flowing through expansive glass sliders to the waterfront terrace and saltwater pool and spa. Gourmet Kitchen & Waterfront Lounge The fully reimagined Cucina Ricci kitchen serves as a chef’s workspace and social hub, with minimalist custom cabinetry, a generous island with seating, and an ultra-premium Miele VitroLine suite including double ovens, induction cooktop, and integrated coffee station. Just beyond, a waterfront lounge or media den opens directly to the covered loggia, creating a seamless indoor-outdoor living experience enhanced by an integrated Yamaha sound system for both interior and exterior zones. Owner’s Retreat & Guest Level Perfectly positioned for privacy, the main-level owner’s retreat is a secluded sanctuary with its own hallway entrance, multiple terrace access points, tray ceiling, recessed lighting, and windows on three sides framing tranquil water views. The suite is completed by dual renovated walk-in closets and a spa-inspired bath with oversized vanities, private water closet, and expansive walk-in shower with rain head, while upstairs three en suite guest suites and a mezzanine den provide luxurious accommodations and flexible space. Resort-Caliber Grounds & Boating Outside, meticulously lit landscaping, a travertine-framed saltwater pool and spa, and a private dock with 14,000 lb lift, new motors, and enhanced WiFi create a turnkey boating haven with immediate access to Sarasota Bay and the Gulf. Practical amenities include whole-house Kohler generator, hurricane protection, impact glass, large utility room with dual Sub-Zero wine refrigerators, and an oversized three-car garage with EV charger wiring. Premier Longboat Key Location Set behind the gates of Lighthouse Point, residents enjoy private tennis, a serene low-density streetscape, and a short walk to the beach. The address is just minutes from the Longboat Key Club’s golf and tennis, the boutiques and restaurants of St. Armands Circle, and the cultural attractions of downtown Sarasota. Call to Experience This Estate Schedule your private showing of this Lighthouse Point waterfront estate today to experience the scale, privacy, and curated luxury that define one of Longboat Key’s most coveted addresses. For additional details and a private tour, contact the listing agent to arrange an exclusive, by-appointment-only viewing.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Steve Walter (941-809-0907)
2185 GULF OF MEXICO DR #223, LONGBOAT KEY, FL 34228
$2,300,00047 Days on yellowkey MLS ID: A4685872
2 Days Off yellowkey (back on 4/24/2026)
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2445 Built: 1996 Tax: $12,693 (2025)Community: Villa Di LanciaSpa: NoCondo
Taxes:$12,693
Remarks: Experience refined coastal living at Villa Di Lancia, one of Longboat Key’s favorite Gulf-front communities. This expansive three-bedroom, three-bath residence offers 2,445 Square Feet of living space paired with breathtaking Gulf and pool views and exclusive private beach access. Designed for both comfort and sophistication, the residence showcases an open floor plan enhanced by elegant crown molding throughout, rich wood doors with gold hardware, and seamless indoor-outdoor living. Sliding glass doors invite natural light while opening to a spacious private balcony—perfect for enjoying sunsets over the Gulf of Mexico and tranquil coastal breezes. The well-appointed kitchen blends functionality with timeless style, featuring granite countertops, solid white cabinetry, built-in appliances, center island with storage, pantry, and a charming breakfast/dinette area. A separate dining space flows effortlessly into the living area, creating an ideal setting for entertaining. The luxurious primary suite serves as a private retreat with balcony access, sweeping Gulf views, a spacious walk-in closet, and a spa-inspired bath complete with Jacuzzi tub, glass-enclosed shower, dual vanities, and additional storage. A guest suite with en-suite bath ensures privacy for visitors, while the third bedroom-perfect as a den or office-features French door entry and built-in workspace. Residents of Villa Di Lancia enjoy an exceptional resort-style lifestyle with guarded security, heated Gulf-side pool and spa, private deeded beach access, Har-Tru tennis courts, fitness center, and community gathering spaces. A strong, well-managed condo association with healthy reserves is a benchmark of the community. Additional conveniences include garage parking, a deeded storage unit, and beautifully maintained grounds within a gated beachfront enclave.
Listing Agent: Kim Ogilvie (941-951-6660)
775 LONGBOAT CLUB RD #408, LONGBOAT KEY, FL 34228
$1,995,0004 Days on yellowkey MLS ID: A4691148
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2122 Built: 1984 Tax: $12,347 (2025)Community: Beaches Of Longboat Key Ph-1Spa: YesCondo
Taxes:$12,347
Remarks: Panoramic Gulf views and unforgettable sunsets take center stage in this beautifully updated fourth-floor residence at The Beaches of Longboat Key, offered fully furnished and ready for immediate enjoyment. Walls of glass and a wraparound terrace create a seamless connection to the water, bringing natural light deep into the open living spaces while framing panoramic coastal vistas. Spanning more than 2,100 square feet of interior living space, the three-bedroom, three-bath floor plan offers a thoughtful layout with both privacy and functionality. The great room combines living and dining areas, positioned to take full advantage of the Gulf backdrop, while the adjacent terrace provides an ideal setting for outdoor dining or quiet relaxation. Recent updates provide peace of mind, including a 2024 A/C replacement, updated impact windows and doors throughout, a newer water heater, and full kitchen and bath renovations completed in 2018. The chef’s kitchen is designed for both everyday use and entertaining, featuring stone countertops, shaker-style cabinetry, newer stainless steel appliances, an extended breakfast bar, and an informal dining area with a dry bar, wine refrigerator, and built-in shelving. The kitchen opens directly to the main living areas, maintaining a natural flow throughout the residence. The primary suite is privately situated and dual closets (one closet is a walk-in), and an en-suite bath, while two guest bedrooms each feature their own bathroom, creating a comfortable arrangement for visitors. The split-bedroom design enhances privacy and livability. Additional conveniences include under-building parking (community also offers lower level of the garage, entirely for unassigned parking) and a private storage unit. The Beaches of Longboat Key offers a full-service lifestyle with on-site management, 24-hour concierge and security, updated common areas, a social room with catering kitchen, fitness center, tennis courts, and a resort-style heated pool and spa. A private boardwalk leads directly to the Gulf’s sandy shoreline, while abundant guest parking enhances ease of access for visitors. Located behind the gates of the Longboat Key Club, this community places you moments from championship golf, tennis, and nearby marinas. St. Armands Circle is just minutes away for dining and shopping, while downtown Sarasota offers cultural destinations including The Ringling Museum, Van Wezel Performing Arts Hall, Selby Gardens, and waterfront parks—creating an exceptional opportunity to enjoy Gulf-front living with both privacy and convenience.
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