Location: Longboat Key , 34228
Do Not Show Listings
100 SANDS POINT RD #108, LONGBOAT KEY, FL 34228
$925,00019 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,063
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2025
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)
2341 HARBOUR OAKS DR, LONGBOAT KEY, FL 34228
$1,399,99014 Days on yellowkey MLS ID: A4688219
0 Days Off yellowkey (back on 4/15/2026)
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2282 Built: 1986Monthly Fee: $1,617 Tax: $11,814 (2025)Community: Harbour Oaks 2Spa: NoVilla
Taxes:$11,814
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to your elevated and relaxed Longboat Key lifestyle—where everything has already been beautifully updated - all that’s left to do is move in and enjoy. Tucked behind the gates of Bay Isles in the charming Harbour Oaks enclave, this bright and open end-unit villa offers gorgeous golf course views, peaceful water features and those unforgettable sunset skies that make every evening feel like a getaway. Inside, the home has a Serena & Lilly feel - its fresh, comfortable and thoughtfully designed. With 2,282 square feet, three en-suite bedrooms and a light-filled open layout - it’s ideal for both relaxed everyday living and hosting friends and family. New luxury vinyl plank flooring runs throughout, while vaulted ceilings, skylights and a garden atrium brings in beautiful natural light. The kitchen has been fully updated with quartz countertops, a marble backsplash, stainless appliances and a casual breakfast bar—perfect for morning coffee before heading to the beach. There’s also a separate dining space for more intimate dinners. Outdoor living is where this home really shines. Sliding doors open to a spacious, two-level screened lanai with a newly pavered deck, electric awning for shade and a newly resurfaced and retiled PebbleTec saltwater pool. It’s your own private retreat—perfect for lounging, entertaining or simply soaking in the peaceful golf course views. The bathrooms have been beautifully reimagined with marble showers, Kohler fixtures and clean, modern finishes. Additional updates include a new roof (2025), newer AC and water heater (2021) and a two-car garage for convenience. Upgrades are plentiful - including Hunter Douglas window treatments and plantation shutters - which add a polished but easygoing feel. Living in Bay Isles means enjoying a true resort lifestyle, with access to a private beach club, marina and scenic walking paths—all in a gated, maintenance-free community. You’re just minutes from the Longboat Key Club and Tennis Center, Publix, everyday conveniences - and a short drive to the shops and restaurants of St. Armands Circle and downtown Sarasota.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Monica Verinder (941-704-4040)
408 GULF OF MEXICO DR #1214, LONGBOAT KEY, FL 34228
$99,0008 Days on yellowkey MLS ID: A4689763
Bed: Bath: 0.0 Built: 2006 Tax: $563 (2025)Community: Boathouse On LongboatDock-Rackominium
Taxes:$563
Remarks: Welcome to Slip #1214 at The Boathouse on Longboat, a rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protected slip in one of Sarasota's most desirable waterfront communities PLUS the price includes a 2018 Robalo R18 with a Yamaha 150 motor, recently detailed tuned up for one-stop shopping! This premium slip accommodates boats up to 31.5 feet in length, with a maximum height of 8' 4" and an 8' 6" beam (No T-tops unless collapsible). Enjoy first-class service at an affordable monthly rate with unbeatable amenities. Located just minutes from both Sarasota Bay and the Gulf, this facility offers on-site fuel, restrooms, a ship store, maintenance services, leasing assistance, and even the popular Dry Dock Waterfront Grill restaurant on site. Simply call ahead and your boat will be launched, fueled, and waiting for you. At the end of the day, return to dock and watch as the team expertly rinses and stores your boat in its covered slip. This is more than boat storage, it's effortless boating in paradise. Don't miss your chance to own high and dry covered storage on Longboat Key!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Daniel Treiman (917-657-7495)
510 PUTTER LN, LONGBOAT KEY, FL 34228
$2,999,000106 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
High School: Booker High
Tax Year: 2024
Middle School: Booker Middle
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
$2,599,99919 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
$999,00073 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
$899,00053 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
$895,000174 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
$1,499,00022 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
$899,000372 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)
5965 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$38,450,00046 Days on yellowkey MLS ID: A4681869
Bed: 11 Bath: 15.0 Gar: 7 Liv Area Sq Ft: 17199 Built: 2026 Tax: $82,342 (2025)Community: Longboat KeySpa: YesSingle Family
Taxes:$82,342
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
Remarks: Under Construction. Set on nearly two private Gulf-front acres, this visionary estate is emerging as one of the most architecturally significant residences ever conceived on Longboat Key. Designed by the internationally acclaimed firm Sweet Sparkman Architecture & Interiors, the home represents a rare convergence of sculptural design, coastal sensitivity, and modern livability. Bold in concept yet timeless in execution, the main residence unfolds with intention. A dramatic foyer introduces expansive living spaces designed to capture light, scale, and uninterrupted Gulf views. The primary suite is conceived as a private sanctuary, complete with dual spa-inspired baths and bespoke dressing rooms. A stately office, refined lounge, formal dining room, and temperature-controlled wine cellar complement the open-concept great room, which transitions seamlessly to a sweeping Gulf-front terrace. Dual kitchens, a showpiece entertaining kitchen and a separate chef’s kitchen, elevate both daily living and grand-scale hosting. The estate continues upward to a rooftop deck with panoramic coastal vistas, while other levels offer a private cinema, multiple guest suites, and a dedicated guest-level kitchenette. A thoughtfully designed guest house and separate pool house provide additional privacy and flexibility for extended stays or staff accommodations. Outdoors, the setting transforms into a private coastal resort. Lush, layered landscaping surrounds a dramatic resort-style pool and spa, expansive entertaining terraces, tranquil water features, and potential for a private tennis and pickleball court — all oriented toward the Gulf’s endless horizon. Positioned along one of the most coveted stretches of Longboat Key, the property offers both seclusion and proximity to the best of the region, including The Resort at Longboat Key Club, The St. Regis Longboat Key Resort, St. Armand's Circle, and the cultural vibrancy of downtown Sarasota. With construction advancing and pricing evolving accordingly, this is a rare opportunity to secure a generational Gulf-front legacy estate at a pivotal stage. Longboat Key’s global recognition, including its inclusion among Forbes Travel Guide’s Top 12 Destinations, further underscores the enduring value of this extraordinary offering.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
660 CEDARS CT, LONGBOAT KEY, FL 34228
$589,00032 Days on yellowkey MLS ID: A4686661
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1440 Built: 1988 Tax: $3,518 (2025)Community: Cedars East Sec 1Garage Condo
Taxes:$3,518
Remarks: Rare Turn-Key Gem in Cedars East | Proven $55k+ Annual Income! Experience the ultimate in coastal luxury and investment savvy in this stunning, fully furnished 3-level retreat. Nestled within the lush, sought-after Cedars East community, this 2-bedroom, 2-bathroom home is a proven performer, having generated over $55,000 in short-term rental income in 2025 alone. Whether you are looking for a lucrative addition to your portfolio or a seamless move into your dream primary residence, this property is truly "turn-key"—every piece of stylish furniture and essential household item is included. Simply bring your suitcase and start living the Longboat Key lifestyle from day one. The thoughtful layout begins with an oversized attached garage on the first floor, providing ample space for vehicles and beach gear. Ascend to the second level to find an entertainer's dream: an expansive open-concept kitchen featuring sleek bamboo cabinetry, convenient pull-out drawers, and a central cooking island with bar seating. The living and dining areas flow effortlessly from the kitchen, anchored by a unique illuminated feature wall that adds a touch of modern sophistication. On the third floor, privacy and views take center stage. The primary suite serves as a serene sanctuary overlooking tranquil wooded vistas, while the front guest bedroom offers picturesque views of the sparkling community pool. Beyond your front door, Cedars East offers a resort experience without the extra membership fees. Spend your days lounging by the Junior Olympic-sized pool, strolling the scenic boardwalks through the mangroves, or casting a line off the bayside fishing pier. For the active resident, the world-class Cedars East Tennis Club is just steps away, featuring 10 Har-Tru courts and professional instruction. You are perfectly positioned just minutes from the pristine sands of Longboat Key, the upscale shopping of St. Armand’s Circle, and the cultural heartbeat of Sarasota, including the Ringling Museum and Mote Marine.
Listing is courtesy of: REDFIN CORPORATION (617-458-2883)
Listing Agent: Marcia Van Ginhoven (704-497-0664)
569 ROUNTREE DR, LONGBOAT KEY, FL 34228
$2,890,000166 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)
3060 GRAND BAY BLVD #195, LONGBOAT KEY, FL 34228
$1,695,00098 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
$995,0007 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
$855,000146 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)
5055 GULF OF MEXICO DR #412, LONGBOAT KEY, FL 34228
$565,00054 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)
455 LONGBOAT CLUB RD #707, LONGBOAT KEY, FL 34228
$1,999,95081 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
$599,0008 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
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.
1000 LONGBOAT CLUB ROAD #1105, LONGBOAT KEY, FL 34228
$1,050,000294 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)
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