Location: Longboat Key
Do Not Show Listings
1241 GULF OF MEXICO DR #109, LONGBOAT KEY, FL 34228
$1,099,000232 Days on yellowkey MLS ID: A4667851
REDUCED by $40,000 (3.5%) on 05/27/2026
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2000 Built: 1996 Tax: $14,616 (2025)Community: Water Club At Longboat KeySpa: YesCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$14,616
Elementary School: Southside Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Live the lavish lifestyle only found at the Water Club on Longboat Key, an idyllic waterfront location with direct access to the white sand beaches only found along the aquamarine waters of the Gulf Coast. This exceptional, beautifully Thomas Moser furnished, 2-bedroom, 2.5-bathroom split plan features spacious en-suite bedrooms with privacy, 10-foot ceilings, floor-to-ceiling hotel-quality hurricane impact windows & sliders, Brazilian Cherry Wood floors, a lovely and convenient powder bath and an incredible master suite with generous walk-in closet and direct access to the private balcony. The masterfully remodeled kitchen showcases custom cabinetry, glass mosaic backsplash, a reverse osmosis faucet, stainless-steel appliances including a Viking stove, Sub-Zero refrigerator and separate dry bar with Sub-Zero wine and beverage refrigerators. Step out onto the extra-large terrace and enjoy the beautiful privacy of the surrounding tropical foliage. Located on the plaza level, you will have quick and easy access to world-class community amenities like 24-hour guard-gated security, full concierge service, a resort-style pool and spa, Har-Tru tennis courts, fitness center, clubhouse with catering kitchen, and over 16 acres of pristine beachfront grounds. Experience the Water Club...timeless elegance, modern design, and a lifestyle beyond compare. Located a short distance from St. Armands Circle and Downtown Sarasota’s culture, shopping and fine dining.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
4960 GULF OF MEXICO DR #206, LONGBOAT KEY, FL 34228
$649,900127 Days on yellowkey MLS ID: A4679160
REDUCED by $10,000 (1.5%) on 04/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1523 Built: 1975 Tax: $7,738 (2025)Community: Windward Bay AmdCondo
Taxes:$7,738
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
Remarks: Public showings are now available for the first time on 5/2/2026. After months of restricted access due to a tenant, this residence is finally available for public showings. Restricted access resulted in only a handful of private showings, giving today’s buyers a rare chance to discover a home that’s been under the radar. SELLER SAYS “SELL!” Unbeatable opportunity at $649,900 for a full Bayfront Waterview, corner end-unit on Longboat Key. Exceptionally priced below market value—this residence represents the lowest-priced Bayfront end unit in the highly desirable community of Windward Bay, in over 5 years. A compelling price point, providing rare access for those seeking to own a premium waterfront residence at an extraordinary price. Encompassing 1,523 square feet, this stylishly furnished, two-bedroom, two-bath residence is thoughtfully designed to showcase uninterrupted panoramic Bay views from every room. Natural light fills the open living and dining areas, where expansive windows frame ever-changing Bay views from sunrise through the evening’s sunset. The remodeled 2024 kitchen opens seamlessly to the main living area and features recently completed upper cabinetry and a sophisticated yet functional layout ideal for both relaxed daily living and entertaining. Recently acquired “chic” French doors in both bedrooms open to the Florida Room, a signature feature for Longboat Key residences, offering additional living space to enjoy morning light and serene Bay vistas. The spacious primary suite includes a private en-suite bath and a generous walk-in closet, providing comfort, supporting everyday living, and abundant storage. “Pet Friendly” Windward Bay is a well-established waterfront community known for its mature landscaping, waterfront setting, resort-style amenities, a strong proactive association with solid reserves, and an enduring reputation as one of Longboat Key’s most welcoming communities. (Attributes that continue to attract owners who value lifestyle as much as long-term stability.) The Milestone Inspection and Capital Reserve Study are complete. Windward Bay’s Monthly Condo Fees for 2025 were actually reduced and for 2026 only increased slightly by $13 a month, demonstrating a financially healthy Condo Association. Offered furnished and move-in ready, this corner end-unit provides flexibility as a full-time residence, seasonal retreat, or investment opportunity. From dolphins at dawn to sunsets on the Gulf—every day is paradise. Community Highlights: Enjoy three beach access points (including one private), 26 acres of lush tropical surroundings including ½ mile of nature trails, two heated pools for year-round enjoyment, fitness center and sauna, clubhouse for social gatherings, tennis and pickleball courts, boat docks (waitlist) and kayak launches for water enthusiasts, covered parking and storage. With convenient access to Downtown Sarasota, St. Armands Circle, Bridge Street, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. An uncommon offering distinguished by exceptional value, location, and the timeless appeal of gulf to bay living. Private showings are available for those seeking a rare chance to own a premium waterfront residence at an extraordinary price.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Debby Mccaig (941-544-1713)
828 BAYPORT WAY, LONGBOAT KEY, FL 34228
$900,00049 Days on yellowkey MLS ID: A4689635
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1456 Built: 1983 Tax: $5,880 (2025)Community: Bayport Bch & Ten Ph FCondo
Taxes:$5,880
Remarks: Bayport Beach & Tennis Club is a true Longboat Key Gulf-to-Bay community, set across 27 acres of beautifully maintained gardens with 1,200 feet of pristine private Gulf beach. Designed by Tim Siebert, one of the founding architects of the renowned Sarasota School of Architecture. Bayport is celebrated for its award-winning, timeless design. Residences like this rarely come to market. This first-floor, fully renovated unit showcases elevated designer finishes throughout. A picture-window screened patio opens to an expansive lanai, surrounded by lush, tropical landscaping; creating a seamless indoor-outdoor living experience. The modern kitchen features Caesarstone “concrete” quartz countertops, an induction cooktop, built-in oven, and custom cabinetry designed for both style and functionality. Each bathroom evokes a five-star resort experience, with thoughtfully curated custom details and designer lighting in both the baths and dining area. All windows and the patio slider have been upgraded to hurricane-impact glass for added peace of mind. The major components of the unit; the air conditioner and water heater have been upgraded. The home also features air purification paint for enhanced interior air quality. One under-building parking space is included, along with a private, locked storage closet which is perfect for bikes and beach gear. Beyond the beach, residents enjoy meticulously maintained nature trails, lushly landscaped grounds, and abundant wildlife. Just steps from the residence, the well-appointed clubhouse features a Junior Olympic-sized heated pool, four Har-Tru tennis courts, a fitness center, and more. Bayport is also known for its vibrant social and recreational lifestyle. Water enthusiasts will appreciate the secluded fishing pier extending into Sarasota Bay. An ideal setting to fish, take in the sunrise, watch manatees glide by, or egrets wading through the mangroves. Paddleboard and kayak launch and storage areas are conveniently located on-site. Residents enjoy easy access to local dining, a nearby supermarket, pharmacy, and charming boutique shops. Just moments away, Bayfront Park offers a popular pickleball program, dog park, and a variety of bayside activities. The Longboat Key Club is also nearby, offering private access to championship waterfront golf, boating, and an array of leisure amenities. Within minutes, you’ll find the renowned St. Armands Circle, known for its exceptional shopping and dining. From there, cross the iconic Ringling Bridge into downtown Sarasota, celebrated for its world-class theater, culture, and culinary scene. Offered by private appointment. Inquire to experience Bayport’s timeless coastal living firsthand.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Alexis Smith-Frady (352-225-1724)
4310 FALMOUTH DR #304, LONGBOAT KEY, FL 34228
$360,000133 Days on yellowkey MLS ID: A4678473
REDUCED by $39,000 (9.8%) on 05/06/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 747 Built: 1969Monthly Fee: $1,196 Tax: $4,937 (2025)Community: Longboat HarbourCondo
Taxes:$4,937
Remarks: Unlock the Door to Your Dream Beach and Boating Lifestyle! Step into a world of unparalleled charm with this move-in ready, fully furnished gem on Longboat Key. This isn’t just a home; it’s a transformative lifestyle choice for those craving adventure, relaxation, and vibrant social connections. Picture yourself waking up to breathtaking bay views every morning from your stylish condo, featuring elegant granite countertops, state-of-the-art appliances, and a spa-like shower that redefines luxury. Your perfect beach days await with exclusive private beach access, complete with a dedicated beach house that offers showers and restrooms for your convenience. For boating enthusiasts, the Longboat Key Yacht Club provides convenient boat slips and kayaks, giving you immediate access to the pristine waters of the bay. Stay energized and engaged with an array of top-tier amenities, including tennis courts, shuffleboard, a rejuvenating sauna, and a fully equipped gym. Join a dynamic social scene filled with workshops, a cozy library, an inspiring art studio, and clay classes, plus the warm camaraderie of the Book Buddies club that fosters connections. With four inviting swimming pools, a grand banquet hall for gatherings, a fun game room for entertainment, and convenient private beach parking, every day feels like a luxurious getaway. This is more than just a condo; it’s a lifestyle experience you truly deserve. Don’t let this extraordinary Longboat Key oasis pass you by! Schedule your showing today and discover if it’s your perfect match!
Listing is courtesy of: HOUSE MATCH (941-213-7028)
Listing Agent: Rachel Rademacher (612-965-6188)
4500 GULF OF MEXICO DR #206, LONGBOAT KEY, FL 34228
$769,000195 Days on yellowkey MLS ID: A4671822
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1523 Built: 1975 Tax: $7,913 (2025)Community: Windward Bay AmdCondo
Taxes:$7,913
Remarks: "One Chance! One Corner-End Condo! One Dream! Don’t Let It Slip Away!” The only coveted South Marina corner/end unit currently on the market at Windward Bay—these special residences are truly prized. End units are usually the first to sell, and for good reason: they offer approximately 250 additional square feet of living space, flooding your home with light and delivering a bright, inviting atmosphere you’ll love. This second-floor location is equally exceptional—it’s the only level where you can enjoy continuous flooring throughout, creating a sleek and modern look. No one below means more freedom, more fun, and more style. Truly extraordinary, this special end unit offers a front-row seat to nature’s most enchanting show. Picture dolphins leaping in the sparkling waters and gentle manatees gliding just below your window—the very reason the current owners fell in love with this home. From breathtaking sunrises to moonlit reflections shimmering across Sarasota Bay, every moment feels like a postcard come to life. Step inside and feel the difference! Where luxury meets comfort with a complete remodel featuring a stunning Thomasville kitchen, sleek new floors, and beautifully updated bathrooms (2022). Enjoy modern conveniences like a Midea refrigerator, remote-control blinds (2025), and most importantly peace of mind with automatic hurricane shutters in the Living and Florida Rooms. This two-bedroom, two-bath property is more than a condo—it’s a lifestyle defined by serenity, security, spectacular views, and maintenance free living. Located in pet-friendly Windward Bay, where two pets are welcome, this community offers the best of Longboat Key Coastal Dream Living. Community Highlights: Enjoy three beach access points (including one private), 26 acres of lush tropical surroundings including ½ mile of nature trails, two heated pools for year-round enjoyment, fitness center and sauna, clubhouse for social gatherings, tennis and pickleball courts, boat docks (waitlist) and kayak launches for water enthusiasts, covered parking and storage. With convenient access to Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez fishing village, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. Windward Bay is a financially healthy Condo Association with a proactive Board. The Milestone Inspection and Capital Reserve Study are complete, Monthly Condo Fees for 2025 were actually reduced, and the new 2026 Monthly Condo fees only increased by $13. Own the best of Longboat Key Bayfront living and make it yours before it’s just a memory! Paradise has an address..and it's 4500 Gulf of Mexico Drive #G206 on Longboat Key, in the rare gem of a community known as Windward Bay! Contact us today to schedule your private showing. Live the Magic & Don't Miss Out! Your Waterfront Dream Awaits!”
2675 GULF OF MEXICO DR #303, LONGBOAT KEY, FL 34228
$1,295,0006 Days on yellowkey MLS ID: A4693865
2 Days Off yellowkey (back on 5/27/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1896 Built: 1979 Tax: $18,625 (2025)Community: VeinteCondo
Taxes:$18,625
High School: Pine View School
Middle School: Pine View School
Remarks: Under contract-accepting backup offers. Experience the ultimate in coastal luxury in this strikingly beautiful 1,900 sq. ft., furnished, direct Gulf-front residence, where breathtaking turquoise water panoramas and beach views surround you from every room. New A/C April 2026. Fridge & Hot water 2024. Thoughtfully designed with an open-concept kitchen, elegant plank wood-style porcelain flooring throughout, and an ideal split floor plan, this exceptional condominium offers two spacious en-suite bedrooms plus a versatile den or home office that easily functions as a third bedroom or study, comfortably accommodating up to 10 guests. Including 3 new sets of hurricane rated sliding doors at a cost of over $40,000. Secure key fab entry at the front Lobby or garage. Enjoy the convenience of an in-unit laundry room, generous walk-in closets, private under-building garage parking, bicycle storage, abundant guest parking, and resort-style amenities including a beachside pool, tennis and pickleball courts, and BBQ area. Perfectly positioned on Longboat Key, you can stroll next door to Maison Blanche for renowned Zagat and Golden Spoon award-winning dining, while Publix, CVS, Longboat Key Fitness personal trainers, and J.McLaughlin are all conveniently located just across the street.
Listing is courtesy of: SARASOTA BEACH TO BAY INC (941-350-7104)
Listing Agent: Debra Lichter (941-350-7104)
5260 GULF OF MEXICO DR #403, LONGBOAT KEY, FL 34228
$649,999143 Days on yellowkey MLS ID: A4677090
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1128 Built: 1974 Tax: $5,922 (2024)Community: The Banyan Bay ClubSpa: NoCondo
Taxes:$5,922
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: This beautifully maintained, ground-floor 2-bedroom, 2-bathroom condo in the desirable Banyan Bay Club offers an exceptional opportunity to own a spacious, modern / updated, move-in-ready home perfectly positioned in a charming, pet-friendly gulf-to-bay community. This unit combines convenience, amenities, and a relaxed coastal lifestyle—all at an outstanding location. This Banyan Bay condominium has an open floor plan with plank style ceramic tile throughout, recently updated featuring new cabinets, vanities, quartzite/quartz countertops and new stainless steel appliances; new Central Air system, and new hot water heater, in-unit full-size washer & dryer, modern tile design in bath, extra sleeping nook for added flexibility, tastefully furnished (can be sold furnished), private patio nestled under a majestic banyan tree-ideal for morning coffee or evening cocktails, large glass hurricane sliders & windows offering a garden view, fiber optic internet included for each unit. SQUARE FOOTAGE IN SLEEPING NOOK IS ADDED TO MAKE THE INTERIOR SQ FTG 1163. The resort-Style Community Amenities (steps from your door): heated community swimming pool, newly resurfaced tennis and pickleball court, fully equipped fitness center, clubhouse with social hall and full kitchen, new day dock, fishing pier, kayak/paddleboard launch, & storage, private gulf beach access with complimentary lounge chairs on the sand, assigned covered carport parking plus ample guest parking, exterior storage for beach gear, on-site manager and carefree exterior maintenance handled by the association, bicycle storage and mature tropical landscaping with giant banyan trees. Unbeatable Location-why Mid-Key is Best! Everything you need is within walking distance; numerous restaurants & cafes, boutiques, beautiful Durante Park with shaded trails and playground, 3 minute walk to your private Gulf beach, 1-minute walk to the community pool, gym, clubhouse, and courts,. This 44-unit condominium offers a social atmosphere, plenty of activities, up to 2 pets allowed (no weight or size limit). Whether you are seeking a full-time residence, vacation getaway, second home or investment property (valued returning renter’s incomes can offset HOA fees), this immaculate condo is ready for you to move in and start enjoying the island lifestyle today. Don't miss this combination of location, amenities and value on Longboat Key!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Kaitlin Kuhn (941-400-7861)
1915 HARBOUR LINKS CIR #6, LONGBOAT KEY, FL 34228
$1,950,00057 Days on yellowkey MLS ID: A4688148
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2476 Built: 2002 Tax: $19,319 (2025)Community: Bay IslesSpa: YesCondo
Taxes:$19,319
High School: Sarasota High
Remarks: Private Beach Access + Gated Bay Isles Living on Longboat Key! Welcome to Emerald Pointe South, where maintenance-free coastal living meets one of the island’s most desirable gated communities. This beautifully maintained villa offers the relaxed Florida lifestyle buyers are searching for — ideal as a full-time residence, seasonal retreat, or investment opportunity. Inside, a bright and open floor plan features spacious living and dining areas filled with natural light from expansive sliding glass doors. The private screened lanai overlooks lush tropical landscaping, creating the perfect setting for morning coffee or evening relaxation. The kitchen offers solid surface countertops, abundant cabinetry, a breakfast nook, and newer appliances including a microwave, dishwasher, and stove. The spacious primary suite features dual walk-in closets and a large en-suite bath with dual vanities, soaking tub, and separate shower. Upstairs, two additional bedrooms each include private en-suite baths, providing comfort and privacy for guests and family. Residents enjoy the security of gated Bay Isles along with coveted private beach access to the Gulf of Mexico. Located just minutes from St. Armands Circle and downtown Sarasota, this home offers easy access to waterfront dining, shopping, golf, marinas, and world-renowned beaches. Low-maintenance island living, private beach access, and an unbeatable Longboat Key location — this is the coastal lifestyle buyers dream about.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Cathy Palmer (678-524-1104)
1211 GULF OF MEXICO DR #105, LONGBOAT KEY, FL 34228
$1,648,0003 Days on yellowkey MLS ID: A4694733
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1598 Built: 1985 Tax: $9,234 (2025)Community: PromenadeCondo
Taxes:$9,234
Remarks: Exceptional opportunity to own this beautifully reimagined first-floor residence at The Promenade on Longboat Key, where luxury coastal living meets sophisticated modern design. Completely gutted and renovated from top to bottom, this stunning condominium offers nearly 400 feet of private beach frontage and partial Gulf of Mexico views from almost every room. This spacious two-bedroom, two-bath split floor plan showcases a bright, open-concept design ideal for both entertaining and relaxed everyday living. The designer kitchen flows seamlessly into the expansive living and dining areas and features custom cabinetry, premium countertops with full-height backsplash, and top-tier appliances. A custom dry bar with built-in wine cooler and under-shelf lighting adds an elegant touch for effortless entertaining. Enjoy breathtaking northwest sunset views from the great room or unwind on the private balcony overlooking the Gulf. The luxurious primary suite offers direct balcony access, a large custom walk-in closet, and a spa-inspired en-suite bath complete with a soaking tub, rain shower system, and large-format designer tile creating a true retreat-like atmosphere. The generously sized guest bedroom provides comfort and flexibility for visitors. Every inch of this residence has been thoughtfully curated with exceptional craftsmanship and attention to detail, balancing modern sophistication with everyday comfort. The Promenade offers a true resort-style lifestyle with a 24-hour staffed gatehouse, concierge services, secure under-building assigned parking, heated Gulf-front pool and spa, expansive sundeck with gazebo and grilling area, four Har-Tru tennis courts, fitness center, craft room, and inviting social spaces. Private beach access lined with charming tiki huts completes this extraordinary Longboat Key experience. Rarely does a completely renovated residence of this caliber become available in one of Longboat Key’s most desirable Gulf-front communities. Experience the ultimate in beachfront living, where every day feels like a vacation.
Listing Agent: Leah George (941-780-0597)
4835 GULF OF MEXICO DR #302B, LONGBOAT KEY, FL 34228
$849,900452 Days on yellowkey MLS ID: A4642701
4 Days Off yellowkey (back on 5/26/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1393 Built: 1970Monthly Fee: $1,736 Tax: $11,313 (2024)Community: Westchester AptsSpa: NoCondo
Taxes:$11,313
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Experience the ultimate beachfront lifestyle in this stunning 1,393 sq. ft. 2-bedroom, 2-bathroom retreat on Longboat Key. Perfectly positioned on the third floor, this home offers amazing views of the beautiful beaches and the endless Gulf horizon—visible from nearly every room! Wake up to the sound of waves in the master suite, where sliding doors open to a private balcony with breathtaking ocean views. Both bedrooms feature spacious walk-in closets, ceiling fans, while both bathrooms have been fully remodeled with modern, high-end finishes and Toto washlet toilets. The newly updated kitchen boasts a sleek induction stove with a vented range hood, perfect for cooking with a view. New AC, LED lighting, and brand-new impact sliding doors enhance comfort and efficiency. Beyond your private oasis, take advantage of resort-style amenities, including two Gulf-front heated pools unique to the Westchester, Elevators, tennis courts, and direct beach access. Plus, you’re conveniently located just minutes from Publix, top-rated restaurants, and boutique shopping. Enjoy short rides to the vibrant St. Armands Circle and downtown Sarasota, where world-class dining, entertainment, and cultural attractions await. This is coastal luxury at its finest—don’t miss your chance to own a piece of paradise!
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-907-2000)
Listing Agent: Donna Wrobel (941-518-7950)
1050 LONGBOAT CLUB RD #901, LONGBOAT KEY, FL 34228
$1,400,0006 Days on yellowkey MLS ID: A4694717
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1409 Built: 1974 Tax: $12,907 (2025)Community: Privateer NorthSpa: YesCondo
Taxes:$12,907
Remarks: Welcome to your beachfront retreat in the sky. Perched on the 9th floor of the highly desirable Privateer North community on Longboat Key, this beautifully furnished 2-bedroom, 2-bath residence offers 1,409 square feet of coastal elegance and breathtaking panoramic Gulf views from every room. Wake each morning to the sound of waves and endless turquoise water, and end each day with spectacular sunsets from the comfort of your living room, primary suite, or private balcony. The light-filled open floor plan is designed to showcase the stunning waterfront setting, featuring spacious living and dining areas that flow seamlessly to the balcony overlooking the Gulf of Mexico. The well-appointed kitchen offers quartz countertops, modern appliances, ample cabinetry, and everything needed for effortless entertaining. The spacious primary suite features direct balcony access, a king-sized sleeping area, and an updated en-suite bath, while the guest bedroom provides generous accommodations for family and friends. Both bathrooms have been tastefully updated with elegant finishes and walk-in showers. Just steps from the building, residents enjoy a secluded stretch of pristine private beach complete with beach chairs and umbrellas, as well as a large heated beachfront pool and spa with unobstructed Gulf views. Privateer North offers an exceptional resort-style lifestyle with a newly renovated fitness center, pickleball courts, shuffleboard, outdoor grilling and picnic areas, covered parking, secure entry, on-site management, and beautifully maintained grounds. Ideally located on the southern end of Longboat Key, this residence is only minutes from the upscale shopping, dining, and entertainment of St. Armands Circle and a short drive to downtown Sarasota, renowned for its arts, culture, waterfront parks, and world-class restaurants. Offering unmatched views, exceptional amenities, and one of the area’s most sought-after beachfront locations, this is coastal living at its finest. ** Seller is a licensed Florida Real Estate Agent
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Jamie Tillman (417-224-1917)
2425 GULF OF MEXICO DR #1A, LONGBOAT KEY, FL 34228
$1,595,00053 Days on yellowkey MLS ID: A4688987
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1513 Built: 1973 Tax: $9,602 (2025)Community: Sea Gate ClubSpa: NoCondo
Taxes:$9,602
Remarks: This is the gorgeous ground floor, walk-out unit next to the beach you've been looking for. Do you prefer to live like a single family home, no elevator, and walk straight out to the beach? Then this is the One! Welcome to Sea Gate Club on beautiful Longboat Key, perfectly positioned near mid-island, and close to shopping at Publix or CVS. As you enter this very private End Unit #1A, you're greeted by Direct and Unobstructed Gulf and beach views as far as the eye can see. Unit #1A has been extensively updated over the last few years, featuring an open kitchen with a huge island, updated cabinets and countertops, and gorgeous porcelain tile flooring. 350' of direct and private beach frontage! This unit is offered Turnkey-Fully Furnished with very tasteful furniture that you'll actually want to keep. Sea Gate Club condos are comprised of 89 units, spread across 15 floors. The building has been extensively updated over the past few years. Recent updates include a new pool and hot tub, new roof, newer hurricane rated windows, newer exterior stucco and paint, new elevator doors, climate-controlled bike storage, and paddleboard/kayak storage. Now is the perfect time to buy in this beautiful building, as there are NO current or pending assessments! Hurry before it's gone, this one is beautiful.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Robert Delaney (941-315-3185)
1965 GULF OF MEXICO DR #G5-103, LONGBOAT KEY, FL 34228
$649,0006 Days on yellowkey MLS ID: A4694695
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 933 Built: 1977Monthly Fee: $1,416 Tax: $3,123 (2025)Community: Seaplace IiiSpa: YesCondo
Taxes:$3,123
Remarks: Experience coastal living at its finest in this beautifully updated ground-floor residence at Seaplace on Longboat Key. This 2-bedroom, 2.5-bath condominium in the desirable G5 building offers northwest Gulf views and stunning sunset skies from the screened lanai, just steps from the beach. The bright, open-concept floor plan features a sleek modern kitchen with glossy cabinetry, quartz countertops, stainless steel appliances, and a spacious breakfast bar perfect for entertaining. Floor-to-ceiling mirrors enhance the natural light and create a spacious, contemporary feel throughout the living and dining areas. The primary suite offers a peaceful retreat with an updated en-suite bath, while the guest bedroom provides comfort and privacy for family and visitors. Hurricane-impact sliding glass doors and windows provide peace of mind and energy efficiency. Whether you are seeking a vacation getaway, seasonal retreat, investment property, or full-time residence, this move-in-ready condo checks every box. Seaplace is a gated Gulf-front community situated on 42 beautifully landscaped acres spanning from the Gulf to the Bay. Residents enjoy resort-style amenities including 24-hour guard-gated security, a newly remodeled clubhouse, two heated swimming pools, kiddie pool, two hot tubs, three Har-Tru tennis courts, walking trails, fitness center, and private beach access with beach chairs and umbrellas provided. Conveniently located near the Longboat Key Club, St. Armands Circle, and Sarasota’s dining and cultural attractions. Schedule your private showing today and start enjoying the Longboat Key lifestyle!
Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
Listing Agent: Michael Renick Pllc (941-400-8735)
1591 GULF OF MEXICO DR #216, LONGBOAT KEY, FL 34228
$2,750,000253 Days on yellowkey MLS ID: A4665247
Bed: 1 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 1556 Built: 2025 Tax: $25,560 (2025)Community: St. Regis Longboat KeySpa: NoCondo
Taxes:$25,560
Remarks: Incredible value at St. Regis Longboat Key. The last two one bedroom residences sold for $2,970,000 and $2,975,000. Step inside this spacious residence to discover a clean, modern interior with a sophisticated Palm Beach vibe. Designed for both style and comfort, this home features a gracious great room featuring floor-to-ceiling windows that flood the interiors with natural light and open to the large, 765 square foot private terrace with a built-in gas grill—perfect for gardening, entertaining friends and family, or relaxing outdoors. The chef’s kitchen is outfitted with Poggenpohl cabinetry, Wolf appliances, a Sub-Zero refrigerator, and Sub-Zero wine and beverage refrigerator, blending elegance with functionality. The owner’s suite also boasts floor-to-ceiling windows, a custom designed closet, and a luxurious bathroom with a frameless walk-in shower, Toto mechanized commode, and double vanities. With generous square footage and a thoughtful layout, this residence easily accommodates overnight guests while maintaining a sense of privacy. Additional features include electronic blinds throughout, adding both convenience and sophistication. Designer light fixtures add an elegant touch throughout the home. St. Regis Longboat Key offers a distinguished array of amenities meticulously curated for its residents. The Private Resident’s Clubhouse offers an environment of exclusivity, complemented by a state-of-the-art fitness center, as well as a pool and spa area reserved solely for residential use. Residents are granted privileged access to the legendary St. Regis Butler and Concierge services, which exemplify world-class hospitality and attention to detail. An extraordinary oceanfront spa awaits, alongside diverse dining experiences that showcase the highest standards of culinary excellence. Personal cabanas along the shore create private retreats for relaxation, while the family-friendly amenities include a meandering lazy river and a unique saltwater lagoon. This lagoon is home to a vibrant array of tropical fish species, graceful stingrays, and the resort’s resident tortoises, offering a captivating wildlife experience within the lush grounds. Spanning seventeen acres of beachfront on the coveted Longboat Key barrier island, this private oasis is conveniently located only 3.5 miles from St. Armand’s Circle, the region’s premier destination for shopping and dining. Whether seeking tranquil solitude or an active social environment, every aspect of life at St. Regis Longboat Key has been thoughtfully designed to anticipate and fulfill the desires of its residents. This offering represents more than just a residence; it is an invitation to embrace the legendary St. Regis lifestyle, defined by elegance, comfort, and outstanding service. Begin your journey to extraordinary Gulf side living.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Lynn Morris, Pllc (941-400-4526)
3060 GRAND BAY BLVD #195, LONGBOAT KEY, FL 34228
$1,595,000136 Days on yellowkey MLS ID: A4677880
5 Days Off yellowkey (back on 5/26/2026)
REDUCED by $100,000 (5.9%) on 05/11/2026
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)
4320 FALMOUTH DR #103, LONGBOAT KEY, FL 34228
$499,000112 Days on yellowkey MLS ID: A4681530
REDUCED by $26,000 (5.0%) on 05/26/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1072 Built: 1969 Tax: $6,901 (2024)Community: Longboat HarbourSpa: NoCondo
Taxes:$6,901
Remarks: “ Significant Reduction for a quick sale , A true Opportunity waterfront Move In Ready" Luxury Waterfront Living | Proven Income Potential Experience refined coastal living in this pristine, pleasantly updated 2-bedroom, 2-bath residence, offered fully furnished and move-in ready. Enjoy spectacular harbor and Intracoastal water views from both the living room and bedroom, extending to the enclosed lanai—an ideal setting for relaxing mornings and elegant evenings. This residence features an excellent rental history, making it a rare opportunity for investors seeking immediate income, while also serving as a perfect full-time or seasonal retreat. Located in an amenity-rich waterfront community, residents enjoy exclusive access to a private beach club pavilion at 4415 Gulf of Mexico Drive, featuring men’s and women’s restrooms, indoor showers, and optional beach and chair storage. Additional private storage is included on the second floor. Resort-style amenities include four heated swimming pools, a fully equipped fitness center, banquet hall with catering kitchen and dance floor, art studio, billiard and card rooms, and professional on-site management. Boat docks available on a first-come basis with water and electric, accommodating sail or power boats up to 34 feet. Additional highlights include mini golf and a scenic waterfront promenade along the harbor and canal. An exceptional opportunity to enjoy luxurious waterfront living or secure a high-performing investment at an incredibly affordable price point. Schedule your private showing today—this opportunity won’t last.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Malihe Karimi (941-376-5099)
1050 LONGBOAT CLUB RD #903, LONGBOAT KEY, FL 34228
$995,00015 Days on yellowkey MLS ID: A4693486
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1409 Built: 1974 Tax: $12,178 (2025)Community: Privateer NorthSpa: YesCondo
Taxes:$12,178
Remarks: Set on the 9th floor at Privateer North, behind the gates of the Longboat Key Club, this beautifully renovated corner residence blends sweeping views, refined finishes and effortless coastal living. Offered TURNKEY FURNISHED, the 2-bedroom, 2-bath home looks out across the golf course, Sarasota Bay, the Intracoastal Waterway and the downtown Sarasota skyline, creating a view that shifts beautifully from morning light to evening sparkle. Inside, the renovation is immediately apparent. Clean neutral finishes, recessed lighting, crisp white trim and an open, comfortable floor plan keep the focus on the scenery beyond the glass. All glass is high-impact, hurricane-rated, and the residence also includes hurricane shutters for added peace of mind. The kitchen is designed for both everyday living and easy entertaining, with quartz countertops, custom cabinetry, high-end appliances, a wine refrigerator and detailed tilework. An inviting eat-in area frames bay views, bringing the water into daily life. The living and dining areas open to a terrace overlooking manicured grounds, the golf course and the bay beyond. Both bedroom suites are generously sized with walk-in closets, and the primary suite enjoys its own private terrace. The updated baths feature tasteful finishes, including a beautifully tiled walk-in shower in the primary bath. Privateer North offers a true beachfront lifestyle with a secure lobby, on-site management, heated pool and spa, fitness center, tennis and pickleball courts, social spaces and private beach access. For those seeking an even broader resort experience, optional membership at the Longboat Key Club offers access to 45 holes of golf, the Tennis Gardens with 20 Har-Tru courts, private dining, beach and pool facilities, spa, fitness, wellness programming, social events and marina amenities. Located on the sought-after south end of Longboat Key, the residence is just minutes from St. Armands Circle, downtown Sarasota, fine dining, shopping, arts venues and the area’s best coastal amenities.
Listing Agent: Bruce Myer (941-376-5311)
6701 GULF OF MEXICO DR #332, LONGBOAT KEY, FL 34228
$795,00051 Days on yellowkey MLS ID: A4689175
Bed: 1 Bath: 2.0 Liv Area Sq Ft: 990 Built: 1971 Tax: $3,403 (2025)Community: Whitney Beach IiiCondo
Taxes:$3,403
Remarks: Finally, you have the opportunity to own your own "Walk-Out", Gulf Front, Beach Condo. Tucked just behind a beach grass sand dune and situated on a grassy knoll, this unit is perfectly positioned to benefit from refreshing sea breezes while offering spectacular sunset views. This rare one-bedroom condo has been completely remodeled and now features a unique two-bathroom floorplan. Remodeled Interior and Modern Upgrades: The spacious living area boasts premium appliances and upgraded stone countertops on new cabinetry within a newly designed open kitchen. Updates abound throughout the unit: new hurricane impact resistant sliding doors and a front window, along with modern bathrooms. The property is being sold turn-key—everything stays, making it a seamless move-in experience. Step inside and discover a bright, inviting interior with an open, light-filled layout designed to maximize both space and natural beauty. Large glass sliders connect the interior to the outdoors, bathing the kitchen and living area in sunlight and blending innovative functionality with coastal charm. The thoughtfully designed bedroom and bathrooms provide serene retreats, perfectly balancing comfort and style. Private Outdoor Oasis: The unique ground floor “Whitney Beach Gulfside” floorplan offers both a front privacy-fenced enclosed patio—ideal for alfresco dining or beachfront gardening—and a rear open patio for relaxation. Whether enjoying a quiet morning coffee or an evening cocktail, the gentle sea breeze creates the perfect setting for unwinding. Resort-Style Community Amenities: Enhance your lifestyle with a range of well-maintained community amenities, including a sparkling pool, tennis courts, shuffleboard, beach chairs, boat slips available for lease, and a tranquil pavilion by the bayou for water enthusiasts. Unmatched Location and Lifestyle: Experience the best of coastal living on Longboat Key. Whitney Beach is located on the quiet, northern end of Longboat Key, close to fantastic restaurants, shops, and shopping—just steps away, an easy bike ride, or a short drive to visit St Armands Circle. This condo combines a highly desirable location with the privacy and comfort of a casual beachfront lifestyle—perfect for year-round living, a seasonal retreat, or a smart investment. With one-month minimum rentals allowed up to 12 times per year, the property offers excellent investment potential. BONUS: the community features two-story buildings and is exempt from Florida’s Milestone inspection and reporting requirements, ensuring a NO SURPRISE experience. Discover Longboat Key: Enjoy the finest Longboat Key has to offer, where luxury meets laid-back coastal charm. Schedule your private tour today!
Listing Agent: Faye Doyle (941-504-7496)
4234 GULF OF MEXICO DR #Q2, LONGBOAT KEY, FL 34228
$648,800444 Days on yellowkey MLS ID: A4643486
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1150 Built: 1973 Tax: $6,219 (2025)Community: Pelican Harbour & Beach ClubCondo
Taxes:$6,219
Remarks: Beautiful, custom 2024 renovated second floor two bedroom, two bathroom Pelican Harbour & Beach Club condo with panoramic Sarasota Bay views plus Deeded Beach access right across the street. Stunning water views across Sarasota Bay are yours from the Great Room, the Primary Bedroom & from your waterfront, covered & screened in Balcony. Entertain your guests here or enjoy your own private dining outdoor lanai. Almost everything is new & improved in this open concept, sunny & bright home from updated electrical to new impact resistant hurricane proof sliders & windows throughout. You’ll really enjoy the large new window in the kitchen with great views of the pool so you can keep an eye on family & grandchildren. The totally redesigned kitchen features all new custom raised panel cabinetry with soft close drawers, light gray with graining Quartz center island & kitchen counters, Frigidaire Gallery induction cooktop, white subway tile back splash & built in Whirlpool microwave & oven. Newly installed Luxury Vinyl Plank flooring is 9” wide plank in a light oak color. Other improvements include a wine refrigerator, a n HVAC system installed in 2023 plus a new roof on this building in 2024 & exterior painted in 2024. The Sellers have invested close to $100,000 to accomplish this stunning remodel. The open floor plan features a large Great Room which includes the dining area & the living room with several couches plus a double bed size Murphy bed attractively hidden between two built in bookshelves & cabinetry for extra sleeping accommodation. The generous sized Primary Bedroom with En Suite bath has serene waterfront Bay views with sliders opening to the screened in balcony. The En Suite features dual sinks, a custom walk-in tub/shower combo & a Toto toilet. The second guest bedroom is bright & comfortable with an adjoining bath with a shower. Bonus feature of the in unit laundry room is a full size LG high efficiency washer & dryer. There is abundant storage room in this unit especially in the number of new kitchen cupboards, storage areas & closets. Assigned storage lockers are also available in the mail room. Pelican Harbour & Beach Club condominium complex offers one of the best Amenity packages on Longboat Key including 200 feet of private deeded beach with new lounge chairs and beach side bathroom, resort style heated pool, adjoining clubhouse, marina with newly built boat docks and fishing docks for boats up to 28 feet with Sarasota Bay frontage of 800 feet, kayak storage & launch area and is large dog/pet friendly complex plus has tennis & pickleball courts which have recently been renovated & painted. On site maintenance staff plus a professional management company, funded reserves and has successfully passed its milestone inspection for the beach side midrise condo building plus has installed brand new roofs & hurricane rated carports. None of the units in this building sustained any damage from hurricanes Helene or Milton or had any water intrusion. Pelican Harbour’s perfect location at Mid Key Longboat is close to all the best restaurants & shops on Longboat Key and Bay Front Park which offers walk in pickleball games, tennis courts, dog park areas plus an exercise/fitness classes building.
Listing Agent: Maruta Miluns (941-374-9702)
1135 GULF OF MEXICO DR #505, LONGBOAT KEY, FL 34228
$1,300,0007 Days on yellowkey MLS ID: A4694362
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1503 Built: 1980 Tax: $13,396 (2025)Community: Beachplace ICondo
Taxes:$13,396
Remarks: DIRECT BEACH FRONT VIEWS AND FIFTH FLOOR EXTRORDINARY PANORAMA! Come visit this property soon, as it boasts Two Parking spots, one in garage, near the elevator and one outside near the front door. Reimagined kitchen with lots of cupboard space, all KITCHEN AID appliances, 2019 Air Handler, never rented and barely occupied. Furnished with exquisite taste and comfortable living space! Beachplace is unique from other communities due to its high rental appeal for returning families! Enjoy the great Olympic size pool located in the center of the complex, plus the oversized hot tub, workout facilities, tennis courts, pickle ball and more! Not to forget the covered baby pool for ages 3 and under! The highest and most sought after units are always BEACHFRONT, holding the best value!
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: James Weingart (440-623-9068)
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