Location: Longboat Key
Do Not Show Listings
2301 GULF OF MEXICO DR #43N, LONGBOAT KEY, FL 34228
$1,000,00038 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$10,915
Elementary School: Southside Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
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 is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Steve Nursey (941-356-7010)
4380 EXETER DR #H202, LONGBOAT KEY, FL 34228
$499,000161 Days on yellowkey MLS ID: A4671530
REDUCED by $21,000 (4.0%) on 04/16/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1970 Tax: $6,314 (2025)Community: Longboat HarbourSpa: NoCondo
Taxes:$6,314
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
Remarks: Experience the ultimate Bay-to-Beach lifestyle in this turnkey 2-bedroom, 2-bath condo at Longboat Harbour, where nearly every room offers sparkling water views and a sense of calm that only waterfront living can bring. Perfect for investors or seasonal residents, this home combines desirable updates with a lifestyle that’s hard to beat. Fully updated in 2025, this home blends modern luxury with coastal charm. LVP flooring, textured ceilings, and fresh paint flow throughout, while the brand-new kitchen boasts with all-white cabinetry, coffee bar, coastal glass backsplash, and quartz countertops. The master suite features custom closet doors, a new porcelain shower with frameless glass, porcelain flooring, and a quartz-top vanity with Bosch washer/dryer in the bath. The hall bath includes a new porcelain shower/tub combo, stylish vanity with quartz countertops, and contemporary Euroflush toilets. Every detail is designed to make the interior as inviting as the stunning views outside. Every update you could hope for in a ready-to-enjoy condo! Step outside and enjoy the resort-style amenities of a vibrant waterfront community. Longboat Harbour offers four heated pools, tennis and pickleball courts, a recreation hall, billiards, game rooms, docks with sailboat access (no bridges to the bay), and a fitness center. Social committee events, on-site grills, and beautiful landscaping surround you at every turn. For beach lovers, the private deeded beach access at 4415 Gulf of Mexico includes a beach house with restrooms, showers, and reserved parking. A short drive from Longboat Key, St. Armands Circle, and downtown Sarasota, you’ll find boutique shops, delightful dining, arts, festivals, and the wonder of Selby Botanical Gardens. Watch Gulf sunsets paint the sky while manatees, ospreys, and egrets play in the waters below… this condo is all about a life of fun, relaxation, and unforgettable moments.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Skrzypkowski (941-328-8307)
5125 GULF OF MEXICO DR #4, LONGBOAT KEY, FL 34228
$725,000392 Days on yellowkey MLS ID: A4645905
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 961 Built: 1983 Tax: $3,448 (2025)Community: Seagrape InnCondo
Taxes:$3,448
Remarks: An exceptional opportunity to own a private family retreat on the pristine shores of Longboat Key—while generating rental income when you’re away. Located within the intimate beachfront enclave of Sea Grape Inn, this unique resort community offers just eight residences, creating a peaceful, uncrowded atmosphere rarely found on the island. Approved for daily, weekly, or monthly rentals, the property provides excellent flexibility for both personal enjoyment and investment potential. From the moment you arrive, the difference is clear. Each residence is thoughtfully appointed and lives more like a private coastal home than a typical vacation rental. This beautifully maintained condo features stone countertops, updated cabinetry, abundant appliances, and tile flooring throughout. The screened porch serves as a tranquil retreat—perfect for enjoying gentle Gulf breezes, spectacular sunsets, and lush tropical landscaping. Step outside to enjoy the heated beachfront pool overlooking the Gulf—an ideal setting for relaxing swims while taking in sweeping water views. The uncrowded beach is just beyond, with chairs provided for effortless seaside enjoyment. Additional amenities include on-site laundry, a BBQ gazebo area, beach towels, and internet service—everything needed for a seamless coastal getaway. Professional on-site management handles all rentals, marketing, cleaning, bookkeeping, and administrative details, offering truly turnkey ownership with no hidden charges. The residence is being offered turnkey furnished, ready for immediate enjoyment or continued rental success. Ideally situated near local restaurants, nature trails, parks with tennis and pickleball, and convenient shopping, this property combines privacy with accessibility. Financials are available upon request. The condo enjoys strong rental demand; showings will be accommodated with 24-hour notice and guest approval. Please contact the listing agent for availability. Life truly is better on Longboat Key!
775 LONGBOAT CLUB RD #808, LONGBOAT KEY, FL 34228
$2,195,00059 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)
240 SANDS POINT RD #4206, LONGBOAT KEY, FL 34228
$1,115,000199 Days on yellowkey MLS ID: A4667039
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 640 Built: 1982Monthly Fee: $1,418 Tax: $9,141 (2024)Community: Inn On The Beach Ph IiCondo
Taxes:$9,141
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: This junior suite, located in Building 4, offers spectacular northwest-facing views of the Gulf, providing owners with breathtaking sunsets and expansive water vistas. For those seeking accommodation for larger groups or families, units 4205 and 4206 are conveniently offered for sale next to each other, allowing parties to stay in close proximity. The suite has undergone a complete renovation, ensuring a modern and refreshed living space for its occupants. Currently, the unit is integrated into the hotel program, providing potential owners with a streamlined rental management option. Building 4 itself boasts an advantageous position on the northernmost stretch of the beach, promising a sense of quietude and enhanced privacy away from the main pool areas. Ownership of this suite grants exclusive access to the prestigious member-only Longboat Key Club. This membership unlocks a wealth of amenities designed to elevate the lifestyle experience, even during owner-occupied periods. Culinary delights await at five exclusive restaurants, offering a diverse array of fine dining options. Golf enthusiasts can indulge in 45 holes of championship golf, while tennis players can hone their skills at the award-winning Tennis Gardens. For relaxation and rejuvenation, a state-of-the-art spa and wellness center is available. The pristine white sandy beach is complemented by umbrella service and attentive waitstaff, ensuring a luxurious beach day. Furthermore, a full-service marina caters to boating enthusiasts.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Jackie Kleppinger (941-320-0049)
240 SANDS POINT RD #4205, LONGBOAT KEY, FL 34228
$1,115,000199 Days on yellowkey MLS ID: A4667038
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 640 Built: 1982Monthly Fee: $1,418 Tax: $9,961 (2024)Community: Inn On The Beach Ph IiCondo
Taxes:$9,961
1935 GULF OF MEXICO DR #G7-304, LONGBOAT KEY, FL 34228
$465,00010 Days on yellowkey MLS ID: TB8496217
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 933 Built: 1979Monthly Fee: $1,367 Tax: $4,940 (2025)Community: Seaplace ViCondo
Taxes:$4,940
Remarks: Experience the best of coastal living in this beautifully maintained 2-bedroom, 1-bathroom condominium, perfectly situated on the third floor of the desirable Seaside community on Longboat Key. Set within a secure, 24-hour guard-gated enclave, this charming residence offers both privacy and peace of mind. Step inside to discover a light and airy interior that was tastefully repainted in April 2021, along with stylish updates to the kitchen and bathroom completed at the same time. The functional layout includes a spacious living area that opens to a generously sized screened-in patio—an ideal space for enjoying morning coffee, evening breezes, or simply soaking in the serene surroundings. A brand-new air conditioning system was installed in October 2024, ensuring year-round comfort and energy efficiency. The building’s exterior also received a fresh coat of paint in April 2021, enhancing its curb appeal and overall charm. This coastal retreat offers direct access to the soft sands and crystal-clear waters of the Gulf, making beach days effortless and spontaneous. Residents also enjoy an array of resort-style amenities, including two heated swimming pools with relaxing spas, a well-equipped fitness center, a playground, three tennis courts, a welcoming clubhouse, and tranquil walking trails that wind through the community. Located just a short drive from the boutique shops, fine dining, and vibrant atmosphere of St. Armands Circle, this property is ideal for full-time residents, seasonal getaways, or investment opportunities. Leasing is allowed with a twomonth minimum lease period, up to six times per year, offering flexibility for owners. Don’t miss your chance to own a piece of paradise on Longboat Key!
Listing is courtesy of: EATON REALTY (813-672-8022)
Listing Agent: Alie Espinoza (813-382-6465)
1000 LONGBOAT CLUB RD #304, LONGBOAT KEY, FL 34228
$874,5005 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.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Judy Kepecz-Hays (941-587-1700)
2425 GULF OF MEXICO DR #8C, LONGBOAT KEY, FL 34228
$1,550,0005 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)
100 SANDS POINT RD #108, LONGBOAT KEY, FL 34228
$925,00018 Days on yellowkey MLS ID: A4688092
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1492 Built: 1966 Tax: $6,063 (2025)Community: Sands PointCondo
Taxes:$6,063
High School: Sarasota High
Middle School: Pine View School
Remarks: Welcome to Sands Point on fabulous Longboat Key: A unique mid-century modern gem situated behind the gates of Longboat Key Club on a tranquil stretch of beach along the sparkling Gulf of Mexico and the inlet of New Pass. This 2 bdrm/2 bath walk-out looks out to the sparkling turquoise waters and you can stroll right out from your back patio in the sugary sand to the one of a kind beachside pool. The gorgeous, wide beach just beyond is complete with tiki huts and loungers for your absolute enjoyment. A perfect spot to sit back and enjoy this incredible coastal paradise. The community lives like a resort and offers it's own little marina, there is a waitlist for slips but it provides a great spot to fish from the seawall, or launch your kayaks and paddleboards. When you're ready for more, just over the bridge is world famous St.Armands Circle filled with restaurants and shopping and the cultural mecca of downtown Sarasota is just moments from there. Schedule your private showing and come imagine what true island living on Longboat Key is all about.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
1085 GULF OF MEXICO DR #205, LONGBOAT KEY, FL 34228
$999,00072 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.
Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
Listing Agent: Michael Renick Pllc (941-400-8735)
2295 GULF OF MEXICO DR #54S, LONGBOAT KEY, FL 34228
$899,00052 Days on yellowkey MLS ID: A4683112
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970 Tax: $7,576 (2025)Community: Islander Club Of LongboatCondo
Taxes:$7,576
High School: Riverview High
Remarks: Welcome to The Islander Club — your turnkey getaway awaits! Step into coastal living with this beautifully updated residence offering effortless style and year-round relaxation. The open, sun-filled layout features tasteful luxury finishes and seamless access to a 38-foot terrace, perfect for unwinding after a day at the beach. Unit 54S has been thoughtfully upgraded throughout, showcasing wood flooring, an updated kitchen with stainless steel appliances, refreshed bathrooms, and unique architectural details that add character and charm. The sunlit primary bedroom includes an ensuite bathroom, a large walk-in closet, and a cozy seating area ideal for reading or enjoying your morning coffee. The spacious second bedroom welcomes guests with terrace access and a generous closet for added storage. The Islander Club’s resort-style amenities include a private 400' beachfront, heated pool, brand-new fitness center, two new sauna rooms, a Har-Tru™ tennis court, two pickleball courts and on-site management for true lock-and-leave convenience. The Islander Club has recently completed an extensive series of capital improvements that elevate both the structural integrity and the everyday experience of the community. Enhancements include exterior stucco repairs and balcony waterproofing, new roofs on the carports, clubhouse, and both residential towers, and modernized pool facilities with new resurfacing, tile, and equipment. Additional upgrades such as refreshed landscaping and lighting, hurricane-rated windows and doors, and a fully renovated fitness center further enhance the appeal and long-term value of the property. Whether you’re seeking a seasonal retreat or a full-time coastal home, this move-in-ready gem delivers the best of island living and peace of mind.
Listing Agent: Julie Lojacono Mackie (773-704-1438)
2295 GULF OF MEXICO DR #115S, LONGBOAT KEY, FL 34228
$895,000173 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)
1445 GULF OF MEXICO DR #501, LONGBOAT KEY, FL 34228
$1,499,00021 Days on yellowkey MLS ID: A4687339
0 Days Off yellowkey (back on 4/10/2026)
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2642 Built: 1982 Tax: $19,801 (2025)Community: Players Club IiiCondo
Taxes:$19,801
Remarks: This stunning corner penthouse spans over 2,800 sq. ft. and boasts breathtaking views of the Gulf, Bay, and city skyline. Key features include elegant stone floors, storm-resistant windows, custom cabinetry, skylights, raised ceilings, and indirect lighting. The kitchen offers a breakfast bar and an adjacent Solarium, perfect for enjoying your morning coffee while taking in both Gulf and city vistas. The spacious sitting room/office adjacent to the primary bedroom features built-in desk and shelving, with expansive glass walls overlooking the pool and Gulf. For entertaining, the impressive 800 sq. ft. private courtyard includes a large fountain and a summer kitchen. This residence also includes a private garage and an additional assigned under building parking space. Residents of The Players Club enjoy a guarded entrance, on-site management, a resort-style saltwater pool and cabanas, spa, Har-Tru tennis courts, pickleball, putting green, a fitness center, renovated clubhouse with catering kitchen, outdoor entertainment area with fire pits, barbecue grills, and direct access to a white sand beach. All of this is just minutes away from the vibrant shops, restaurants, theaters, and art galleries of St. Armands Circle and Downtown Sarasota.
Listing Agent: Ian Addy, Pa (941-961-8850)
6951 GULF OF MEXICO DR #14, LONGBOAT KEY, FL 34228
$899,000371 Days on yellowkey MLS ID: A4648003
4 Days Off yellowkey (back on 4/15/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1170 Built: 1973 Tax: $11,138 (2024)Community: Sea PinesSpa: NoCondo
Taxes:$11,138
Remarks: WOW! The minute you open the front door of this first floor Coastal Retreat Seaside condo, you will be captivated by the shimmering, turquoise Gulf of Mexico Water View and the Panoramic Sandy White Beach in front of you. You'll be eager to get a closer look from the glassed in Florida Room, so you may overlook the beauty of this updated, attractively furnished & decorated first floor residence at Sea Pines, a small 28 unit beach front condo complex on the north end of Longboat Key, Florida. Since purchasing five years ago, these owners have lovingly transformed this almost 1400 square foot, corner unit with extra windows, open concept, two bedroom with En Suite baths & walk in closets to today's coastal contemporary style tastes. Improvements include light oak color Luxury Vinyl wide plank flooring throughout, Samsung stainless steel appliances including washer & dryer, new HVAC installed, updated the primary bedroom with a quartz counter vanity, tiled & glass door shower, and fitted out closet. The condo's interior was painted as well & new, high quality neutral colored living room, dining & bedroom furniture, rugs, lighting & drapery, artwork and a large entertainment center installed. A new tiled roof was installed on this building in 2024. Additional features include impact resistant windows in both bedrooms & the office adjacent to the kitchen. Plantation shutters cover all these windows. This office area is fitted out with oak cabinetry, desk & drawers, perfect for working at home. The spacious 26-foot-long lanai (Florida Room) can be entered from either the primary bedroom or the living room via sliders. This may be your favorite room with mesmerizing Gulf & beach views over the sea grass pathways to the water. And of course, the magnificent Longboat Key Gulf of Mexico sunsets will thrill you whether watching from your lanai or enjoying on the beach while toasting your good fortune! This turnkey handsomely appointed & attractively furnished seaside retreat offers great rental income if you so wish. Currently these owners are using RVA Rentals, but a new owner can choose how or if to lease out this unit. Rental friendly Sea Pines can be leased out six times a year with a one month minimum time period. Two additional benefits to this first floor Unit 14 are that these owners have paid $5357 assessment for new landscaping for the complex plus new interior glass sliders will be installed in the living room & primary bedroom and sellers have paid for that as well. Sea Pines has an electronic gated entry for security & privacy. Amenities include a large, heated pool, is large pet friendly & offers excellent rental income possibilities. Charming Longboat Village is nearby with fabulous restaurants like The Shore, Mar Vista, Whitney's, Ventura's & the thriving Whitney Shopping Center. Anna Maria Island is just across the Longboat north end bridge for additional night life entertainment.
Listing Agent: Maruta Miluns (941-374-9702)
3060 GRAND BAY BLVD #195, LONGBOAT KEY, FL 34228
$1,695,00097 Days on yellowkey MLS ID: A4677880
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2250 Built: 1994 Tax: $10,399 (2025)Community: Grand Bay 1Spa: YesCondo
Taxes:$10,399
Remarks: One or more photo(s) has been virtually staged. Positioned high on the south side and 9th floor of Building One, this turnkey-furnished residence at Grand Bay offers expansive Sarasota Bay, golf course and downtown views, refined interiors, and effortless resort living on Longboat Key. Spanning nearly 2,300 square feet, the open layout is framed by walls of glass and a wraparound terrace with access from nearly every room—creating a seamless connection between indoor spaces and the ever-changing water views below. Recently refreshed with new contemporary furnishings included, the residence is truly move-in ready. The spacious great room flows naturally into the dining area and kitchen, creating an inviting setting for entertaining or relaxed daily living. Floor-to-ceiling glass sliders bring in abundant natural light while showcasing views of the bay, marina, and downtown Sarasota. The primary suite is a private retreat with terrace access, generous closet space, and a well-appointed en-suite bath. Two additional bedrooms provide flexibility for guests, office use, or extended stays, each positioned to enjoy natural light and views. Electric storm shutters throughout offer convenience and peace of mind. This residence includes two deeded parking spaces and an additional storage unit, a valuable combination rarely available at this elevation. Grand Bay is one of Longboat Key’s most sought-after gated communities, offering residents a full suite of resort-style amenities including two heated swimming pools with sundecks, Har-Tru tennis courts, a modern fitness center, clubhouse, and an active social calendar. On-site management and 24-hour security ensure a well-maintained, secure environment. As an exclusive benefit, owners enjoy deeded access to the private Bay Isles Beach Club, where Gulf-front pavilions, grilling areas, and pristine shoreline create the perfect setting for beach days and sunset gatherings. Located behind the gates of Bay Isles, Grand Bay balances privacy with proximity. Just minutes away are the boutiques and restaurants of St. Armands Circle, the cultural offerings of downtown Sarasota, championship golf and marina access at Harbourside, and the beaches of Lido and Siesta Key. From boating and tennis to theater, dining, and art, this residence places the best of Sarasota living within easy reach. A rare opportunity to enjoy turnkey bayfront living in one of Longboat Key’s premier communities.
Listing Agent: Roger Pettingell (941-387-1840)
615 DREAM ISLAND PL #105, LONGBOAT KEY, FL 34228
$995,0006 Days on yellowkey MLS ID: A4689957
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1293 Built: 1985Monthly Fee: $2,208 Tax: $4,735 (2025)Community: Harbour Villa Club At The BuccaneerSpa: YesCondo
Taxes:$4,735
Remarks: Welcome to Paradise Found at Harbour Villa Club, a waterfront luxury condo that is truly a slice of heaven on earth. This stunning property offers breathtaking views of the glistening water and is situated in a prime location that is peaceful, serene, and truly one-of-a-kind. A true Longboat Key gem. As you step inside this luxurious, fully renovated (2025) condo, you'll be greeted by a spacious and open floor plan that is perfect for entertaining guests or simply relaxing in style. The living area is bathed in natural light, thanks to the open plan, high ceilings, and large sliders that offer stunning views of the Bay, the Intercostal Waterway, and protected Sister Keys. The gourmet kitchen is a chef's dream. Built completely custom, featuring top-of-the-line appliances, ample counter space, and plenty of creative storage. The primary bedroom is designed with your comfort in mind, offering tremendous space, ample dual closets, and unparalleled views of the water. The primary bathroom is equally luxurious, featuring high-end fixtures, beautiful tile work, and a spacious shower. Entertain with ease and impress your guests with a sleek and stylish wet bar, perfect for any occasion. The secondary bedroom with a large space is ideal for a great flex space, depending on your needs. But perhaps the most impressive feature of this luxury condo is the covered and screened lanai. This space is perfect for hosting guests, sipping your morning coffee, or evening cocktail, or simply taking in the beauty of your surroundings. For the boating enthusiasts, this condo conveys a deeded boat slip #14, which includes electric, water, and new composite decking. This slip is 40ft in length and can dock up to a 55'+/- vessel and is positioned directly outside the unit, which is rare. This community is flush with mature tropical landscaping and grounds. Other amenities include a heated pool, hot tub, outdoor grill, kayak storage/launch, boat ramp, climate-controlled bicycle/locker storage, Brand New tennis courts, two Brand New pickleball courts, and one covered parking space. Harbour Villa Club is one of the few Longboat Key communities that has the ability to rent on a weekly basis. This gives you options and flexibility to carve out your formula of ownership and use. Located within a short distance to nearby popular beaches, restaurants, clubs, and parks, and just a short drive to St. Armands Circle and Downtown Sarasota. This property is more than just a luxury condo - it's a lifestyle. So why wait? Come see for yourself what makes this property so special and start living your Longboat Key dream today.
Listing is courtesy of: CENTURY 21 BEGGINS ENTERPRISES (813-658-2121)
Listing Agent: Jesse Griffin (941-822-6165)
2089 GULF OF MEXICO DR #G1-105, LONGBOAT KEY, FL 34228
$855,000145 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)
842 BAYPORT WAY #842, LONGBOAT KEY, FL 34228
$675,00020 Days on yellowkey MLS ID: A4687058
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1983 Tax: $5,662 (2025)Community: Bayport Bch & Ten Ph FSpa: NoCondo
Taxes:$5,662
Remarks: Poised within the Gulf to Bay community of Bayport Beach and Tennis Club, 842 Bayport Way offers 1570 square feet of effortless indoor-outdoor living. This first floor corner residence brings added natural light and extra privacy, giving the feeling of a private home with the ease of low maintenance living. The open layout includes a spacious kitchen, a primary bedroom with office space, walk-in closet and ensuite bath with dual vanities, as well as convenient in-unit laundry, covered parking and private storage closet. A combined dining and living area opens to a screened lanai and extended brick patio. This is a favorite spot for morning coffee, afternoon siestas and al fresco dining watching sunset skies. A garden gate leads to a direct side path to deeded beach access across the road. For pet owners, Bayport is small-pet friendly, and this walk-out location makes dog-walking especially easy. Spanning 27 acres of exquisitely landscaped tropical grounds, Bayport is celebrated for its timeless Tim Seibert architecture, exceptional amenities, and easy resort lifestyle. Residents enjoy a heated Jr. Olympic pool, clubhouse, fitness center, tennis, bocce ball, and shelled walking paths. Along the bay shoreline, a fishing pier, kayak launch and storage is perfect for morning paddles or simply enjoying nature . On the Gulf side, 1,200 feet of deeded beach access, complete with loungers and umbrellas, makes enjoying Longboat Key’s famously uncrowded beaches effortless. The condo’s split floor plan works well for year round living or a seaside escape. A favorable rental policy offers excellent income opportunity. Located mid-key, Bayport keeps you close to shopping, daily conveniences, great island dining, and the vibrance of Sarasota, all while feeling tucked away and serene. Settle in and enjoy a slice of true paradise on Longboat Key.
Listing Agent: Rosemarie Mckee (941-504-9396)
5055 GULF OF MEXICO DR #412, LONGBOAT KEY, FL 34228
$565,00053 Days on yellowkey MLS ID: A4683419
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1484 Built: 1973 Tax: $8,183 (2024)Community: Club Longboat Beach & TennisSpa: YesCondo
Taxes:$8,183
Remarks: Discover an exceptional value opportunity in Club Longboat on Longboat Key, one of the island’s most desirable beachside communities known for its active lifestyle and resort style amenities. This three bedroom, two bathroom ground floor walkout residence is currently the least expensive unit in the community and presents a rare chance to create a fully customized coastal retreat. With a solid existing layout and desirable ground level access that enhances indoor / outdoor living, the residence offers tremendous flexibility. Buyers have the opportunity to redesign and expand the third bedroom to add additional square footage, whether to create a more spacious primary suite, an inviting guest retreat, or a dedicated office or flex space. The potential to transform this residence into a personalized showpiece is exceptional. Club Longboat is ideal for tennis, pickleball, and beach enthusiasts, offering eight Har Tru tennis courts with three lined for pickleball, two heated swimming pools, and 750 feet of private Gulf front beachfront complete with lounge chairs and umbrellas. The serene waterfront setting enhances the peaceful atmosphere and scenic surroundings. The residence includes a covered parking space directly in front of the unit along with abundant guest parking. On site management serves the 85 residences, providing convenience and peace of mind within a welcoming, all ages community. Owners enjoy a pet friendly environment with no weight restrictions and a flexible rental policy allowing one month minimum rentals up to twelve times per year, creating excellent income potential. Conveniently located near shopping and fine dining, this is a rare opportunity to secure a value driven property in an amenity rich Longboat Key beachfront community and make it entirely your own.
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
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