Location: Longboat Key
Keyword(s): Booker High
Keyword(s) High School: Booker High
Do Not Show Listings
2039 GULF OF MEXICO DR #G3-203, LONGBOAT KEY, FL 34228
$499,99919 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,576
Elementary School: Southside Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Experience the Best of Coastal Living at Seaplace on Longboat Key! Welcome to this beautifully maintained 2-bedroom, 2.5-bath residence offering a perfect blend of comfort, style, and relaxed island living. This spacious two-level layout features an inviting open-concept living and dining area with neutral coastal tones, tile flooring throughout the main level, and seamless access to a private lanai—ideal for enjoying tranquil views and Gulf breezes. The updated kitchen is designed for both functionality and style, showcasing granite countertops, white cabinetry, stainless steel appliances, and a convenient breakfast bar, perfect for casual dining or entertaining. Upstairs, you’ll find two generously sized bedrooms, each offering privacy and comfort. The primary suite serves as a relaxing retreat, while the guest bedroom is ideal for family or visitors. The additional half bath on the main level adds convenience for guests. This residence is offered in move-in ready condition and reflects pride of ownership throughout. Residents of Seaplace enjoy approximately ½ mile of pristine Gulf beach frontage and an exceptional array of amenities across 42 beautifully landscaped acres. Highlights include two heated swimming pools and spas, Har-Tru tennis courts, scenic walking trails, a fitness center, and a clubhouse with kitchen, library, and sauna. Additional features include playground areas, grilling stations, on-site management, and a 24-hour staffed gatehouse for security. Whether you're searching for a primary residence, vacation getaway, or investment opportunity, this home offers the ultimate Longboat Key lifestyle in one of the island’s most sought-after communities. Schedule your private showing today!
Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
Listing Agent: Michael Renick Pllc (941-400-8735)
1571 HARBOR CAY LN, LONGBOAT KEY, FL 34228
$4,750,000205 Days on yellowkey MLS ID: A4666688
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4209 Built: 1987 Tax: $16,980 (2024)Community: Bay IslesSingle Family
Taxes:$16,980
Tax Year: 2024
Remarks: Experience the ultimate in luxury coastal living in this 4,209-square-foot stunning waterfront home, perfectly situated in the highly sought-after, gated Bay Isles Harbor Section—an exclusive boating community with only 67 custom residences on south Longboat Key. Designed for elegance and comfort, this timeless 4-bedroom, 3.5-bath estate welcomes you with a dramatic open main living area featuring soaring 23-foot ceilings filled with natural light, rich oak flooring, custom lighting and a gas/wood-burning fireplace. Expansive walls provide the perfect showcase for fine artwork, while the spacious living and dining areas flow seamlessly into a warm family room and a chef’s dream kitchen. The gourmet kitchen is equipped with custom mahogany cabinetry, premium stainless-steel appliances including an induction cooktop, a large island topped with quartzite countertops, and a bright breakfast area overlooking the pool and waterway. Sliding glass doors lead to your private outdoor oasis—a massive 28-foot saltwater pool with solar heating and a partially covered patio with heat-resistant coral stone tile. The luxurious master suite offers two walk-in closets, a sitting area or office, and a spa-inspired bathroom with translucent onyx walls and flooring, a soaking tub, and an oversized shower. Additional features include a large laundry and craft room, an oversized two-car garage with workbench, hurricane-impact windows and doors, reinforced garage doors, and a brand-new concrete tile roof. A beautifully landscaped circular drive welcomes guests, while the deep-water bayou behind the home provides direct access to Sarasota Bay—ideal for boating enthusiasts. Residents of Bay Isles enjoy 24-hour gated security, membership to the Bay Isles Beach Club, and close proximity to the Longboat Key Club, St. Armands Circle, world-class dining, shopping, and the brand-new five -star St. Regis Longboat Key Resort. This exceptional property offers the best of luxury, privacy, and the coveted waterfront lifestyle on Florida’s Gulf Coast.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Julie Klick (941-780-6001)
415 L AMBIANCE DR #B202, LONGBOAT KEY, FL 34228
$2,150,000167 Days on yellowkey MLS ID: A4670048
0 Days Off yellowkey (back on 4/17/2026)
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2385 Built: 1992 Tax: $23,948 (2025)Community: L Ambiance 1Spa: YesCondo
Taxes:$23,948
Remarks: Gulf-front enclave offers a rare blend of luxury, location, and lifestyle that transforms every day into a retreat. From the moment you step inside, you’re greeted by an atmosphere of refined elegance and architectural clarity—crafted for those who appreciate design as a way of life. This residence exudes sophistication with interiors envisioned by an internationally acclaimed designer, delivering clean lines, thoughtful textures, and a timeless palette that compliments the natural beauty outside your doors. Here the edges between indoor living meet the outdoors. An open light-filled living area opens to a wraparound terrace, Gulf views, and tranquil gardens, where the turquoise Gulf and the green of the fairways meet the Florida sunshine. The culinary chef’s kitchen features premium appliances, contemporary cabinetry, and a layout that invites effortless entertaining—whether you’re hosting a sunset cocktail hour or a quiet dinner with close friends. This is a three-bedroom, three-bath home designed for comfort and privacy. Each bedroom is an en-suite retreat, offering serene views. Positioned along the Gulf shoreline, you’ll enjoy the sunrises, moonrises, golf course vistas, and the aroma of fresh-cut greens as a constant backdrop. Yet you’re just moments from the heart of the action: steps to the beach, golf course (Longboat Key Club). Minutes to St. Armands Circle, with access to dining, shopping, and cultural scenes that define Longboat Key living. Key Features at a Glance: - Location: South end of Longboat Key, beachfront setting with golf course and garden views - Residence: 3 bedrooms, 3 en-suite baths - View: Beach, and golf course views; tranquil garden vistas - Proximity: Steps to the beach and Longboat Key Club; Very close to the West Coast’s second-largest marina - Lifestyle: Luxury coastal living with resort-style amenities and ample entertaining spaces. Residents enjoy a 24-hour manned gated community, concierge service, security, an on-site manager, a resort-style heated Olympic-size pool and spa, a state-of-the-art fitness center, outdoor BBQ areas, three social rooms, and three overflow guest suites available on a first-come basis. This pet-friendly community is dedicated to making every detail perfect, delivering a lifestyle that is as effortless as it is extraordinary. Furniture is available to purchase separately from the real estate. WHERE LONGBOAT KEY COASTAL LIVING MEETS THE GULF!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Judy Kepecz-Hays (941-587-1700)
536 KETCH LN, LONGBOAT KEY, FL 34228
$2,695,00035 Days on yellowkey MLS ID: A4686553
REDUCED by $200,000 (6.9%) on 04/12/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2960 Built: 2016Monthly Fee: $10 Tax: $13,360 (2025)Community: Country Club ShoresSpa: NoSingle Family
Taxes:$13,360
Remarks: Welcome to an extraordinary south Longboat Key canal front estate in Country Club Shores, located 2 in from Sarasota Bay on a lushly landscaped 1/3 acre lot, where luxury and tranquility come together in perfect harmony. This residence is the ultimate sanctuary, blending refined modern design and extraordinary finishings with the serenity of its picturesque surroundings. Untouched by recent hurricanes, this home features impact windows and high-quality craftsmanship and is built to withstand the demands of south Florida’s climate. The completely renovated ~3,000 sq ft, 3-bedroom, 3-bathroom property is outfitted with premium finishings and an open plan that sets new standards for convenience and today’s modern lifestyle. From the cozy media room with wet bar and separate office, to the pro-outfitted chef’s kitchen and owner’s suite that is a truly an inspiring spa-like retreat, every inch of this home exudes luxury and comfort. The home has been thoughtfully renovated, featuring large plank porcelain floors and 10’ ceilings adorned with custom millwork details throughout. Plan to be impressed by the formal foyer that delivers your guests to the spectacular “Art Salon” and spacious gathering area. The gourmet kitchen is a chef's dream, featuring a stunning 9’ Dolomite Island with a vegetable sink and a 30” Fisher-Paykel dishwasher drawer adjacent to custom dual pantries. The custom built-in Thermador refrigerator/freezer columns, warming drawer, and microwave provide everything needed to prepare any culinary creation with ease. The Carrera marble backsplash complements the quartz countertops that house the commercial grade Thermador 6-burner gas range and griddle with 2 convection ovens. The kitchen area features 12-foot bifold impact door panels and 8-foot bifold impact windows, which can be fully opened to seamlessly connect the kitchen with the patio area and stunning Bay views. The owner's retreat offers a relaxing Zen atmosphere with soft tones that complement the water views. Escape to the spa inspired bathroom to indulge in a two-person freestanding hydrojet bath or relax in the spacious aroma steam shower featuring dual rain showerheads and hand showers. The blue calcite custom vanities illuminate the ethereal experience, complemented by a Toto Neorest water closet and a custom walk-in closet. The media room is perfect for movie night, featuring surround sound and wet bar with a wine captain. The two spacious guest suites feature spacious bathrooms with floor to ceiling large format porcelain tile, Hansgrohe/Gessi fixtures, marble and Cambria quartz countertops, and mosaic marble backsplashes. The baths also feature Restoration Hardware towel curios with matching pulls, oversized rain showerheads with custom finishes. Outside is a 110-foot seawall and versatile dock system, that includes an entertaining area, mooring station with shore power pedestal/water, and a floating dock perfect for launching kayaks or boarding a boat. The spacious greenhouse offers a sanctuary for relaxing and all your planting needs delivering that boujee-chic retreat embellished with orchids and herbs to further elevate the experience. Located on the highly desired south end of Longboat Key, adjacent to the Resort at Longboat Key Club and nearby St Armands Circle, this property includes deeded beach access and unrivaled convenience to Sarasota. Call now for a private tour of this bespoke property.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Kathy Callahan (941-900-8088)
3806 GULF OF MEXICO DR #C310, LONGBOAT KEY, FL 34228
$389,00014 Days on yellowkey MLS ID: R4911020
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1046 Built: 1970Monthly Fee: $1,457 Tax: $2,813 (2025)Community: Beach Harbor ClubCondo
Taxes:$2,813
Elementary School: None
Remarks: Longboat’s Beach Harbor club is situated on 5 Acres along the most beautiful stretch of Longboat Key Shoreline. Sugary sand and flowing seaoats beside the azure blue Gulf of Mexico. The beach Harbor club offers 133 condo units, deeded beach access with showers, umbrellas and beach chairs. Amenities also include newly constructed boat slips, rooftop decks, outdoor cook areas, heated oversized swimming pool, community area for kayaks, clubhouse, and shuffle board. Longboat Beach Harbor is a friendly community with group events and many fun times to build relationships and enjoy sense of community living. Close to Bayfront Park with Tennis, Publix/CVS shopping. This renovated condo is situated on the 3rd floor not requiring flood insurance. Air conditioned indoor hall-way with security entrance. Newly appointed appliances, bathrooms, HVAC, luxury flooring and trim. Up-scale appointed fixtures and details throughout.
Listing is courtesy of: LEN SCAVRON (908-304-5454)
Listing Agent: Len Scavron (908-304-5454)
2819 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$3,799,999180 Days on yellowkey MLS ID: A4669533
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1173 Built: 1955 Tax: $36,688 (2024)Community: Coquina BeachSpa: NoSingle Family
Taxes:$36,688
Remarks: BEACH FRONT OPPORTUNITY on Longboat Key! Rare chance to own DIRECT GULF FRONT property on the coveted south end of Longboat Key in Sarasota county. This charming, 1955 beach cottage sustained significant hurricane damage and is now being sold AS-IS for land value only. No HOA fees! Build your dream coastal retreat on this prime GULF-front lot and enjoy breathtaking sunsets, white-sand beaches- just steps to Publix grocery, 1.5 miles to the stunning St. Regis resort, and easy access to nearby St Armand’s dining/shopping, downtown Sarasota, golf, and marinas. You do not want to miss this opportunity to create your own piece of paradise on BEAUTIFUL Longboat Key!
Listing is courtesy of: SERHANT (646-480-7665)
Listing Agent: Jenn Flanders (941-232-0788)
2301 GULF OF MEXICO DR #43N, LONGBOAT KEY, FL 34228
$1,000,00040 Days on yellowkey MLS ID: A4686190
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970 Tax: $10,915 (2025)Community: Islander Club Of LongboatCondo
Taxes:$10,915
Remarks: One or more photo(s) has been virtually staged. Perfectly positioned in the sought-after Islander Club Condominium, this 2-bedroom, 2-bath residence offers commanding Gulf and beach views from the living room, dining room, and both bedrooms. Expansive windows frame the sparkling waters of the Gulf of Mexico, creating a breathtaking backdrop for everyday living while showcasing spectacular sunset skies each evening. Situated front and center on the 4th floor, the residence enjoys one of the most desirable vantage points in the building, elevated enough for panoramic shoreline views yet close enough to feel immersed in the beauty and rhythm of the beach below. Competitively priced, the condominium presents a rare opportunity for the next owner to create their own vision of coastal living. Whether designing a sophisticated modern retreat or a relaxed island escape, the residence offers a blank canvas ready to be transformed to your personal taste and style—truly a chance to make it your own. Residents of the Islander Club enjoy a collection of resort-style amenities including direct access to the pristine Gulf Beach, a beachfront Olympic size swimming pool, tennis courts, fitness center, clubhouse, library, and beautifully landscaped tropical grounds. Located on the coveted south end of Longboat Key, the community offers convenient access to Publix, the world-class shopping and dining of St. Armands Circle as well as the vibrant arts, cultural venues, and waterfront restaurants of downtown Sarasota. Go ahead – Make it your own and have it your way!
Listing Agent: Steve Nursey (941-356-7010)
775 LONGBOAT CLUB RD #808, LONGBOAT KEY, FL 34228
$2,195,00061 Days on yellowkey MLS ID: A4683021
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2122 Built: 1984 Tax: $17,930 (2025)Community: Beaches Of Longboat KeyCondo
Taxes:$17,930
Remarks: Behind the gates of the Longboat Key Club, this exceptional residence at The Beaches captures sweeping, unobstructed views of the Gulf of Mexico and its pristine shoreline, where vivid sunsets paint the horizon each evening. Perched on the eighth floor, this coveted Star floor plan is ideally positioned as a spacious end residence, offering 2,122 square feet of thoughtfully designed living space with 3 bedrooms and 3 full baths. Walls of glass frame panoramic water vistas and invite natural light to pour into the main living areas. Newly installed impact-rated sliders enhance both storm protection and seamless indoor-outdoor living, while oak engineered hardwood flooring flows beautifully through the living room, dining area, and kitchen, creating a warm yet sophisticated coastal aesthetic. The generous layout provides an effortless blend of comfort and refinement, with well-proportioned bedrooms and baths designed to accommodate both everyday living and gracious entertaining. The Beaches is recognized as one of the premier beachfront addresses within the Longboat Key Club, offering direct access to the sugar-white sands and turquoise waters of the Gulf. Residents enjoy an elevated level of service and amenities, including a 24-hour concierge, resort-style pool, fitness center, tennis courts, and impeccably maintained grounds. Ideally located on the southern end of Longboat Key, this gated community affords convenient access to the fine dining and boutiques of St. Armands Circle, the vibrant arts and culture of downtown Sarasota, and the exclusive offerings of the Longboat Key Club. This is a rare opportunity to secure a front-row seat to the Gulf and embrace the effortless elegance of Florida’s most sought-after coastal lifestyle.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Lenore Treiman (941-356-9642)
1000 LONGBOAT CLUB RD #304, LONGBOAT KEY, FL 34228
$874,5007 Days on yellowkey MLS ID: A4689434
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1409 Built: 1972 Tax: $3,950 (2025)Community: Privateer SouthCondo
Taxes:$3,950
Middle School: Brookside Middle
Remarks: Experience elevated coastal living in this beautifully renovated two-bedroom, two-bath golf-front condominium, ideally situated behind the gates of the prestigious Longboat Key Club in the sought-after community of Privateer South on Longboat Key. Thoughtfully redesigned with a refined coastal aesthetic, this residence showcases a seamless blend of modern elegance and relaxed waterfront living. From the moment you enter, you are welcomed by an open-concept layout filled with natural light, enhanced by expansive windows and tranquil golf course views. The fully updated kitchen features sleek cabinetry, premium finishes, and a clean, contemporary design that flows effortlessly into the spacious living and dining areas—ideal for entertaining guests or enjoying quiet evenings at home. Every detail has been carefully curated to provide both style and functionality. The primary suite offers a serene retreat, complete with a beautifully appointed en-suite bath and generous closet space, while the guest bedroom and bath provide comfort and privacy for visitors. Both bathrooms have been tastefully renovated with modern fixtures and finishes, creating a spa-like atmosphere throughout the home. Residents of Privateer South enjoy a true resort-style lifestyle with an impressive array of amenities. Relax by the sparkling beachfront pool overlooking the Gulf of Mexico, maintain your wellness routine in the fully equipped fitness center, or gather with neighbors in the inviting social room. On-site management ensures ease of ownership and peace of mind. Perfectly positioned between the Gulf and Sarasota Bay, this exceptional property offers convenient access to world-class dining, shopping, and cultural attractions, all while being tucked away in a secure, gated enclave. Whether you are seeking a full-time residence or a luxurious seasonal retreat, this golf-front condominium delivers the very best of Longboat Key living.
2425 GULF OF MEXICO DR #8C, LONGBOAT KEY, FL 34228
$1,550,0007 Days on yellowkey MLS ID: A4688797
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1470 Built: 1973 Tax: $17,374 (2025)Community: Sea Gate ClubCondo
Taxes:$17,374
Remarks: Welcome to the prestigious Sea Gate community on world renowned Longboat Key! With direct views of the Gulf of Mexico from every room and situated perfectly on the 8th floor, this stunning 2-bedroom, 2-bathroom residence offers just under 1500 square feet of refined coastal living on pristine white shores, endless turquoise waters and vibrant sunsets that create a truly extraordinary backdrop that is postcard worthy! This beautifully appointed residence has been meticulously maintained by the owners and showcases expansive glass sliders that flood the home with natural light, seamlessly connecting the indoor living spaces to a private balcony and your front-row seat to one of Florida’s most coveted coastlines.Thoughtfully enhanced for both comfort and style, the residence features fresh interior paint, a new HVAC system and Hot Water Tank and some new kitchen appliances, delivering a modern and move-in-ready experience. The addition of an in-unit washer and dryer provides a rare and highly desirable level of convenience within the building. The spacious layout offers an effortless flow between the living, dining and kitchen areas for both everyday living and entertaining.The primary suite serves as a peaceful retreat, complete with generous proportions, ample storage and a calming ambiance inspired by the surrounding Gulf views, walk- in closet and ensuite. A well-appointed guest bedroom boasts a private balcony and large closet, while the guest bath provides comfort and privacy for visitors. Residents of Sea Gate enjoy an intimate, resort-style lifestyle with direct beach access, a beachfront pool, tennis courts, a fitness center, and beautifully maintained grounds, all within a private, boutique community setting. Additionally, Sea Gate offers covered parking, ample guest parking and a large storage unit! The building has undergone major capital improvements in recent years, including impact-rated windows (2021), a full exterior restucco and repaint (2022), a new roof (2023) and upgrades to the pool, spa, sundeck and elevator doors. Residents enjoy resort-style amenities including a Gulf front pool and hot tub, fitness center, clay tennis court, library, and a social room with catering kitchen. Shaded tiki huts, outdoor showers, and climate-controlled storage for bikes, kayaks, and paddleboards complete the experience of true beachfront living. All fully paid for by current owners, totaling over $100K/unit. Ideally located near daily shopping, Longboat Key offers a lifestyle defined by elegance and ease, with world-class golf, waterfront dining, boating, and the upscale shops and restaurants of St. Armands Circle just moments away, along with the cultural attractions of Sarasota. With monthly rentals allowed, a unit of this stature could rent for 10k a month in season offering potential income. Option to be sold turnkey furnished as well. Don't hesitate, this unit is a beaut and easy to show!
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Melissa Killion (941-248-6840)
510 PUTTER LN, LONGBOAT KEY, FL 34228
$2,999,000107 Days on yellowkey MLS ID: A4676878
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2253 Built: 1968 Tax: $17,343 (2024)Community: Country Club ShoresSpa: NoSingle Family
Taxes:$17,343
Remarks: Welcome to 510 Putter Lane, a stunning canal-front retreat nestled in the coveted Country Club Shores community on the south end of Longboat Key. Completely renovated with meticulous attention to detail, this turnkey furnished 3-bedroom, 2-bathroom residence offers coastal luxury and modern convenience just moments from Sarasota Bay and the Gulf of Mexico and walking distance to the beach. From the moment you arrive, the home's crisp curb appeal hints at the exceptional updates within. A brand-new 24-gauge standing seam metal roof (2025) crowns the home, complemented by all-new impact-rated windows, sliding glass doors (2024), and an elegant new front door (2024), ensuring peace of mind and energy efficiency. Step inside to find an open-concept layout bathed in natural light, where engineered hardwood flooring flows seamlessly throughout. The expansive great room features an electric fireplace set in a stacked stone lighted niche, creating a cozy yet elegant focal point. Plantation shutters, new lighting fixtures, ceiling fans, and recessed lighting add both style and comfort. The gourmet kitchen is a chef’s dream, anchored by a six-burner gas range with a pot filler, custom range hood, quartz countertops, and a suite of brand-new appliances including a refrigerator/freezer, dishwasher, microwave, and ice maker. Soft-close cabinetry offers generous storage, while the floor-to-ceiling built-in wine rack provides a striking and functional design element perfect for entertaining. Both bathrooms have been completely transformed with new tile, cabinetry, lighted mirrors, and high-end fixtures, delivering a spa-like experience. Every inch of this home has been curated for relaxed coastal living with no detail overlooked. Step outside to your private backyard oasis where a newly resurfaced pool and shell stone deck (2024) invite hours of sun-soaked enjoyment. The lush new landscaping and custom landscape lighting enhance the ambiance, while new rain gutters and a new Seawall Cao (2024) will help protect your investment year-round. Boaters will appreciate the direct, no-bridge access to Sarasota Bay. There is also the convenience of a Deed Beach Access! Whether you're spending the day on the water or relaxing poolside at home, this property delivers the quintessential Florida lifestyle. Additional updates include a recently replaced A/C system (2023), ensuring year-round comfort. Offered fully furnished and turnkey, 510 Putter Lane is move-in ready and designed for immediate enjoyment. Country Club Shores is one of Longboat Key’s most sought-after neighborhoods, known for its deepwater canals, beach access, and proximity to the Longboat Key Club, St. Armands Circle, and downtown Sarasota. Rest easy knowing this coastal dream home had no hurricane damage from 2024's storms! Whether you're seeking a primary residence, vacation getaway, or investment property, this exceptional home checks every box. Don’t miss this rare opportunity to own a completely renovated waterfront gem in one of Longboat Key’s most desired communities. 510 Putter Lane offers everything you need—style, substance, and the ultimate coastal lifestyle.
Listing is courtesy of: SARASOTA TRUST REALTY COMPANY (941-366-1619)
Listing Agent: Renee Preininger (941-400-4235)
531 WEDGE LN, LONGBOAT KEY, FL 34228
$2,599,99920 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
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)
1085 GULF OF MEXICO DR #205, LONGBOAT KEY, FL 34228
$999,00074 Days on yellowkey MLS ID: A4681713
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1819 Built: 1981 Tax: $8,830 (2025)Community: Beachplace IiiSpa: YesCondo
Taxes:$8,830
Remarks: Spacious 3-Bedroom End-Unit Residence in Sought-After Beachplace Welcome to this beautifully maintained three-bedroom, two-bath end-unit condominium offering exceptional natural light, generous living spaces, and serene views in one of South Longboat Key’s most desirable beachfront communities. The open living and dining areas are thoughtfully designed for comfort and entertaining, featuring expansive sliders and windows that flood the space with sunlight and create seamless indoor-outdoor flow. A spacious living room opens to a south-facing screened lanai—perfect for enjoying morning light, golf course views, and gentle coastal breezes. The kitchen is bright and functional, offering ample cabinetry, full appliance package, and convenient in-unit laundry tucked neatly into a dedicated closet. Adjacent dining space provides flexibility for everyday living or hosting guests. The primary suite is generously sized and enjoys tranquil views, abundant natural light, and direct access to the lanai. Two additional bedrooms are versatility for guests, family, or a home office, all thoughtfully laid out to maximize privacy and comfort. Being an end unit, this residence benefits from additional windows and enhanced light throughout, creating an airy, welcoming atmosphere. Neutral finishes and tasteful furnishings allow for immediate enjoyment while offering an excellent canvas for personalization. Residents of Beachplace enjoy resort-style amenities, including a heated pool with lap lanes, spa, tennis courts, a fully equipped clubhouse with gathering spaces, on-site management, and private deeded beach access complete with lounge chairs and umbrellas. The community’s prime location places you moments from St. Armands Circle, Longboat Key Club, and downtown Sarasota’s dining, shopping, and cultural attractions. This well-cared-for residence presents an outstanding opportunity—whether as a primary home, vacation retreat, or income-producing investment in a premier Gulf-front community.
2295 GULF OF MEXICO DR #115S, LONGBOAT KEY, FL 34228
$895,000175 Days on yellowkey MLS ID: A4670081
2 Days Off yellowkey (back on 4/15/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970 Tax: $10,253 (2024)Community: Islander Club Of LongboatCondo
Taxes:$10,253
Remarks: Under contract-accepting backup offers. Wonderful "Manhattan Style" beachfront Condo with sweeping views of Sarasota Bay and views of the Gulf now available at the popular Islander Club on LBK. This gorgeous beachfront renovation was completed 4 years ago and truly shows all the craftmanship that went into the process under the owner's direction. Open kitchen beings the morning light into the room for enjoying your coffee or tea as you gaze across the sparking blue waters of the bay. Large 38ft balcony also has views of bay and a bit of the Gulf of Mexico. The Primary suite is a comfortable 13X20 which accesses the balcony and has a large walk-in closet. It is light and bright and a restful haven away from the main living area. The Islander club has recently renovated their clubhouse. The gym overlooks the gulf and the pool. There is a conference room, library, and an Olympic size heated pool, not to mention their Har-Tru tennis courts. The Location is very convenient. The shops of Bay Isles with the Publix and CVS are just a couple of minutes away. It's only 10 minutes to World renown St Armand Circle. Make this your permanent home or your week-end getaway. Secured Building . At The Islander Club "Everyday is a Holiday and Life is an endless vacation.
Listing Agent: Michael Nink, Pa (941-914-2805)
569 ROUNTREE DR, LONGBOAT KEY, FL 34228
$2,890,000167 Days on yellowkey MLS ID: A4670192
Bed: 3 Bath: 3.5 Gar: 4 Liv Area Sq Ft: 3428 Built: 2024Monthly Fee: $167 Tax: $15,281 (2024)Community: Longboat Key EstatesSpa: NoSingle Family
Taxes:$15,281
Elementary School: Pine View School
Remarks: STUNNING New Construction WATERFRONT Home in LONGBOAT KEY ESTATES!!! Experience the pinnacle of coastal luxury in this new modern waterfront residence, perfectly positioned in one of Longboat Key’s most prestigious neighborhoods. Completed at the end of 2024, this architectural masterpiece offers direct Sarasota Bay access and a DEEDED BEACH ACCESS just steps away—the rare opportunity to enjoy both boating and beachside living in one extraordinary setting. Built to today’s highest standards, this all-block concrete home is designed for peace of mind with hurricane impact windows and doors, and engineered to withstand the toughest conditions while exuding timeless sophistication. Clean architectural lines, expansive glass, and a balanced façade define its striking contemporary profile, with an impressive entry that introduces the home’s elegant yet minimalist aesthetic. Inside, a spacious open concept living area seamlessly blends modern design with coastal comfort. The great room centers around a sleek gas fireplace framed by custom built-ins, while floor-to-ceiling sliding doors flood the space with natural light and open to the waterfront terrace. The gourmet kitchen is a showpiece in itself, featuring a massive quartz island with seating for five, custom dark cabinetry, glass subway tile backsplash, and top-tier Italian stainless-steel appliances, including double wall ovens and a gas cooktop. Designer lighting adds a bold splash of color, balancing style and warmth for effortless entertaining. Step outside to a covered deck that extends the main living area, complete with a full summer kitchen, wood-paneled ceiling, and multiple fans for year-round comfort. The third floor rooftop terrace delivers panoramic 360 degree views of the bay and beach—perfect for enjoying unforgettable Florida sunsets. The home offers three luxurious ensuite bedrooms, each with spa like bathrooms and designer finishes. The primary suite is a private sanctuary overlooking the water, featuring a large walk-in closet and a lavish bath with soaking tub, dual vanities, and an oversized walk-in shower. A private mother-in-law suite includes its own bedroom, bath, and full kitchen, providing ideal accommodations for guests or extended family. The backyard oasis is anchored by a sparkling lap pool surrounded by modern pavers and lush tropical landscaping. A brand-new seawall and dock provide deep water access to Sarasota Bay with no fixed bridges to the Gulf, making it a boater’s dream. The four car garage and in-home elevator add both convenience and functionality to this exceptional property. Located in the heart of Longboat Key, just steps from Bayfront Park and minutes from Saint Armands Circle and downtown Sarasota, this home delivers an unparalleled lifestyle. Enjoy world class dining, boutique shopping, championship golf, and some of the most beautiful beaches on Florida’s Gulf Coast—all at your doorstep. DO NOT WAIT ON THIS AMAZING OPPORTUNITY!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-758-7777)
Listing Agent: Jay Travis, Pa (941-812-7277)
2089 GULF OF MEXICO DR #G1-105, LONGBOAT KEY, FL 34228
$855,000147 Days on yellowkey MLS ID: A4673060
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1257 Built: 1974 Tax: $7,928 (2025)Community: Seaplace ISpa: YesCondo
Taxes:$7,928
Remarks: Wake up in This Resort-Style Living Condo located on a Barrier Island Paradise! Positioned just steps from the Gulf of Mexico on exclusive Longboat Key—where sugar-white sand beaches stretch endlessly and dolphins play in turquoise waters—this professionally redesigned ground-floor residence in Seaplace's coveted G1 building offers the rare combination of coastal luxury, modern sophistication, and effortless living. Minutes to the boutiques and dining of St. Armands Circle and Sarasota's world-class cultural scene, this is the Florida lifestyle you've been dreaming of. Step into an open-concept culinary kitchen masterpiece featuring custom cabinetry with integrated lighting, pantry, and generous extra cabinet space for all your storage needs. Premium Thermador and Bosch appliances—including an induction range and new vent hood—paired with expansive quartz countertops make this kitchen as functional as it is beautiful. Adjacent dining flows seamlessly, perfect for entertaining or intimate dinners at home. Overlooking serene garden views, the primary bedroom is a haven of calm. Custom-built closets provide abundant storage, while blackout window treatments ensure restorative sleep. The spa-inspired en-suite bath elevates everyday rituals with a double vanity, an expanded premium shower system, and stylish tile flooring with an elegant glass partition that enhances the open, airy design. This gated, 24-hour guarded community features custom wood ceiling, luxury vinyl flooring, new electrical panel and wiring, brand-new HVAC system and tankless water heater, reverse osmosis water system for pure filtered water, High-speed internet, all-new plumbing fixtures, interior doors, hardware, recessed lighting, and ceiling fans, hurricane-grade sliding doors, windows, and premium front door with keypad entry. The lanai—upgraded with beautiful new exterior tile—frames lush garden views and offers the perfect setting for morning coffee with the Gulf breeze, al fresco dining, or sunset cocktails. It's your own slice of tranquility in a tropical setting. Living at Seaplace means waking up to the sound of waves and ending each day with spectacular Gulf sunsets. This community features a newly renovated clubhouse and state-of-the-art fitness center, two sparking pools plus kiddie pool, two relaxing hot tups, three tennis courts, scenic walking trails through lush tropical landscape, covered parking beneath the building, and steps to pristine Gulf beaches. Beyond your front door lies 12 miles of unspoiled barrier island beauty—powdery beaches where sea turtles nest, championship golf courses, waterfront dining, and kayaking through peaceful mangrove tunnels. Stroll St. Armands Circle for upscale shopping, savor fresh grouper at a waterfront restaurant, or simply watch the sunset paint the sky in shades of pink and gold. This is coastal living at its finest. This home is completely renovated and ready for immediate occupancy. For ultimate convenience, beautifully curated furnishings may be available for purchase outside of the sale—allowing you to simply unlock the door and start living your dream lifestyle from day one. Whether you're seeking a sophisticated year-round retreat, a luxurious seasonal escape, or the ultimate coastal haven, this residence delivers on every front. Schedule your private showing today—and start living the life you've always imagined!
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Beverly Perez (941-323-4600)
455 LONGBOAT CLUB RD #707, LONGBOAT KEY, FL 34228
$1,999,95082 Days on yellowkey MLS ID: A4680080
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2410 Built: 1990 Tax: $9,861 (2025)Community: PierreCondo
Taxes:$9,861
Remarks: Welcome to The Pierre, a distinguished Gulf-front address behind the private gates of the Longboat Key Club, offering a rare blend of refined coastal living, privacy, and world-class resort lifestyle appeal for discerning buyers from around the globe. Located on the seventh floor, Residence 707 showcases spectacular sunset skies over the Gulf of Mexico, complemented by peaceful bay and city vistas, creating a dynamic panorama from sunrise through evening. Expansive windows fill the interiors with natural light while framing the natural beauty of Longboat Key’s shoreline and Sarasota Bay. Thoughtfully designed for both relaxed living and gracious entertaining, the residence offers generous living spaces and a seamless indoor-outdoor connection. The floor plan includes two ensuite bedrooms and a flexible third bedroom with sliding retractable wall, three full baths, and spacious living and dining areas—each with direct access to the residence’s gracious balconies. Residents of The Pierre enjoy an exceptional array of amenities, including direct private beach access, a beachfront pool, spa, fitness center,, tennis courts, a newly renovated lobby, club gathering room, meeting room and 24-hour guard security. Private guest suites are also available for visiting family and guests on a nominal rental basis. Ownership is further enhanced by secure garage parking, a private secured storage area, and onsite professional management, providing ease and confidence for both year-round and seasonal owners. Beyond the residence, membership opportunities at the renowned Longboat Key Club provide access to a celebrated resort lifestyle, featuring championship golf courses, world-class tennis, spa and wellness facilities, multiple dining venues, beach services, and an active social calendar (membership subject to application and availability). Perfectly situated near St. Armands Circle and downtown Sarasota’s cultural attractions, Residence 707 represents a rare opportunity to own within one of Longboat Key’s most prestigious waterfront communities—where international sophistication, panoramic views, and a coveted club lifestyle converge in one extraordinary coastal setting.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Judy Wright, Pa (941-232-8041)
1932 HARBOURSIDE DR #242, LONGBOAT KEY, FL 34228
$599,0009 Days on yellowkey MLS ID: A4688978
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1192 Built: 1982Monthly Fee: $81 Tax: $7,099 (2025)Community: Fairway Bay 1Spa: YesCondo
Taxes:$7,099
Middle School: Pine View School
Remarks: Value opportunity behind the gates of Bay Isles in the highly sought after Fairway Bay community. This turnkey furnished move-in ready two-bedroom, two-bathroom residence presents an exceptional chance to enjoy the Longboat Key lifestyle along with the rare advantage of one under building garage parking space. Enjoy peaceful views of Sarasota Bay, surrounding mangroves, and native wildlife from an open floor plan designed to maximize natural light and comfortable indoor and outdoor living. White tile flooring runs throughout the main living areas, while a wall of sliding glass doors opens to the terrace, ideal for relaxing outdoor eating. The kitchen features light cabinetry, custom lighting and captures water views. The primary suite offers direct terrace access and an ensuite bath with dual vanities, upgraded shower, and a fitted walk-in closet. A welcoming guest bedroom has an ensuite bath with upgraded spa tub. Ready for immediate enjoyment as a primary home, seasonal retreat, or investment opportunity. Ownership includes membership to the private Bay Isles Beach Club with deeded beach access and facilities for social activities. Residents of Fairway Bay enjoy walking trails, heated pools, a fitness center, tennis and pickleball courts, clubhouse amenities, and kayak launches. Optional membership to the Longboat Key Club provides access to championship golf, Har Tru tennis, spa services, waterfront dining, and a deep-water marina. Ideally located just minutes from St. Armands Circle and downtown Sarasota’s renowned arts and dining scene, this residence offers comfort, convenience, and an outstanding opportunity to enjoy the Longboat Key waterfront lifestyle within one of the island’s most desirable gated communities.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
1000 LONGBOAT CLUB ROAD #1105, LONGBOAT KEY, FL 34228
$1,050,000295 Days on yellowkey MLS ID: A4657701
1 Days Off yellowkey (back on 4/14/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1290 Built: 1972Monthly Fee: $209 Tax: $7,027 (2024)Community: Privateer SouthCondo
Taxes:$7,027
Remarks: Under contract-accepting backup offers. Seller wants offers! Rarely available and beautifully renovated 11th floor Penthouse with breathtaking Gulf, Sunset and Bay views and ideally situated within a short beach walk between the popular Resort at Longboat Key Club and the luxurious St. Regis Resort. This island gem has brought many years of joy to the Seller based on its perfect South LBK beachside location and all it's resort style amenities. The sleek European style interior boasts carefree luxury vinyl plank flooring, along with new carpeting in both bedrooms, LED lighting, dazzling designer tile in both bathrooms, and the color scheme throughout mirrors its direct seaside setting. The open-concept kitchen makes entertaining a breeze and offers gorgeous quartz counter tops, custom backsplash, stylish GE appliances, sparkling hardware, and a customized breakfast bar. Both the primary and guest bedroom each lead to a separate balcony where you can soak up the sun while enjoying the peaceful surroundings and endless water and beach views. Residents enjoy the convenience of on-site management, an updated guest suite & additional guest quarters for your overflow visitors, a secure lobby, tennis and pickle ball, heated pool and spa, a great gym, and a refurbished lobby, hallways, social room, community bathrooms, and the landscaping create an even more exceptional experience in this world-class beach location. A membership to Longboat Key Club’s exceptional offerings will provide many hours of outdoor fun and golf & tennis enthusiasts will appreciate the two championship courses & tennis gardens. These facilities, along with professional instruction and well-appointed pro shops, cater to athletes of all levels. Outside the gates, Longboat Key offers fine & casual dining, deep water boating & fishing, 10 miles of sugar sand beaches, and a great variety of local treasures to explore. The Sarasota Opera & Ballet, Van Wezel Performing Arts, and all of Sarasota's cultural offerings including boutique shopping and popular restaurants are just minutes away, creating the perfect balance of relaxation and activity in this sought-after island paradise.
Listing is courtesy of: ROSEBAY INTERNATIONAL REALTY, INC (941-366-7673)
Listing Agent: Tina Rudek Stark, Pa (941-920-0303)
510 WEDGE LN, LONGBOAT KEY, FL 34228
$1,990,000194 Days on yellowkey MLS ID: A4668133
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: 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)
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