Location: Longboat Key
Do Not Show Listings
545 SANCTUARY DR #B506, LONGBOAT KEY, FL 34228
$1,828,000189 Days on yellowkey MLS ID: A4675800
0 Days Off yellowkey (back on 5/28/2026)
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2375 Built: 1991 Tax: $19,482 (2025)Community: Sanctuary IiiCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$19,482
Elementary School: Southside Elementary
High School: Riverview High
Tax Year: 2025
Middle School: Booker Middle
Remarks: Under contract-accepting backup offers. Bright, spacious and beautifully maintained, this 3BR/2.5BA fifth-floor residence at The Sanctuary offers refined coastal living in one of Longboat Key’s most sought-after gated communities, ideally positioned on the island’s desirable southern end. Upon entry, walls of floor-to-ceiling glass sliders immediately draw your eye to sweeping panoramic views of the Sarasota city skyline, shimmering Sarasota Bay and the emerald fairways of the Links golf course. By night, downtown’s twinkling lights create a dramatic and ever-changing backdrop. The popular Brittany floor plan features recessed lighting, crown molding, 18-inch tile flooring throughout the main living areas and a tiled open terrace perfectly suited for sunrise coffee or evening cocktails. The kitchen has been opened to enhance flow and functionality, offering solid-surface countertops, a center island, tile backsplash and an eat-in area framed by a wall of glass. Double doors lead to the oversized primary suite, filled with natural light and offering terrace access, a walk-in closet and a spa-inspired bath with soaking tub, walk-in shower and dual vanities. Wraparound terraces further enhance the indoor-outdoor lifestyle, making this residence ideal for both everyday living and entertaining. The Sanctuary delivers an unparalleled resort-style experience with 1,200 feet of pristine white-sand beachfront, private boardwalk beach access, a heated Gulf-side pool with 25-meter lap lane, outdoor whirlpool spa and beachfront gazebo. Additional amenities include two lighted Har-Tru tennis courts, a state-of-the-art fitness center, saunas, an entertainment room, on-site management, 24-hour guard-gated security and coveted under-building parking. Pet-friendly with restrictions. Nestled behind the gates of the exclusive Longboat Key Club, this exceptional residence offers the perfect blend of luxury, privacy and breathtaking views—truly one of Longboat Key’s premier addresses.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Judy Kepecz-Hays (941-587-1700)
1055 GULF OF MEXICO DR #504, LONGBOAT KEY, FL 34228
$1,299,000290 Days on yellowkey MLS ID: A4663883
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1503 Built: 1981 Tax: $14,051 (2024)Community: Beachplace IiiSpa: YesCondo
Taxes:$14,051
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: This direct Gulf-front residence at Beachplace offers an extraordinary opportunity to enjoy the very best of Longboat Key’s beachfront lifestyle. Perfectly positioned to capture unobstructed views of the Gulf of Mexico, this furnished two-bedroom home combines a serene coastal retreat with strong rental potential—producing an average of $70,000 annually in gross rentals. Whether you envision it as your move-in-ready getaway, a property to personalize, or an income-producing property, the possibilities here are unmatched. From the moment you step inside, natural light fills the open floor plan. The welcoming foyer flows into a spacious living and dining area, framed by newer impact-rated walls of glass that extend to the private terrace. This expansive beachfront balcony is a highlight of the home, offering front-row seats to breathtaking sunsets, the sound of gentle waves, and refreshing Gulf breezes. The split-bedroom layout is designed for comfort and privacy. The primary suite enjoys direct terrace access, a large closet, and an en-suite bath with dual vanities. The guest bedroom is equally inviting and privately situated, ideal for hosting family or visitors. Additional features include tile flooring throughout, a well-appointed granite kitchen, and deeded parking—adding everyday ease for seasonal or year-round living. Life at Beachplace feels like a private resort. This sought-after community offers residents 24-hour staffed security, on-site management, a clubhouse perfect for a lively escape, along with Har-Tru tennis courts, a modern fitness center, and heated swimming pool with spa. Pristine beachfront access and lushly landscaped grounds create the ultimate Florida lifestyle. Located on the southern end of Longboat Key, Beachplace provides unmatched convenience. You’re just minutes from the Longboat Key Club’s golf and tennis facilities, the boutique shops and dining of St. Armands Circle, and the vibrant cultural venues of downtown Sarasota—including theaters, galleries, and waterfront parks. From beachside relaxation to world-class dining and entertainment, everything that defines Sarasota living is within easy reach.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Roger Pettingell (941-387-1840)
5655 GULF OF MEXICO DR #A107, LONGBOAT KEY, FL 34228
$799,00077 Days on yellowkey MLS ID: A4687549
1 Days Off yellowkey (back on 5/28/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1274 Built: 1975Monthly Fee: $1,164 Tax: $3,185 (2025)Community: Cedars West Of Longboat IncCondo
Taxes:$3,185
Remarks: Under contract-accepting backup offers. Experience the best of Gulf-front living and gorgeous views in this move-in-ready, two-bedroom, two-bath waterfront condominium, perfectly positioned in an elevated community just steps from the beach. This home is in impeccable condition and is designed for relaxation, with a seamless blend of comfort, style and convenience. It's being sold turnkey with lovely furnishings. The kitchen features new Samsung stainless steel appliances, plenty of counter space, and a comfortable sitting area. An open floor plan with a large living room, remote-controlled sunshades and three-panel impact sliding glass doors opens to an inviting screened lanai with a tropical ceiling fan, blurring the lines between indoor and outdoor living. There are ceiling fans in every room. The primary suite offers a large bath with a separate water closet and a huge walk-in closet. There are also impact sliders leading out to the lanai with a view of the Gulf. The guest suite is spacious with lots of closet space. The laundry is neatly tucked away and features Bosch machines. If you love the beach and enjoy stunning sunsets, Cedars West is really the perfect place to live. This location is walking distance to our local restaurants (Lo-Key, Harry's and Hugos), convenience shopping and all the amenities you’ll need to enjoy life here on Longboat Key. This community has tennis, a heated pool, BBQ area, bike racks, and kayak storage. Cedars East, just across the street, offers tennis membership with a world-class facility. This financially sound community offers peace of mind with a new roof and no assessments planned. With a liberal rental policy allowing up to 26 rentals/year, this property presents an exceptional investment opportunity while still offering the flexibility to enjoy your own beach getaway. There is a locking owner's closet in the unit. You have to see this home to really appreciate how special it is.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Judy Mitchell (941-275-6838)
6330 LAGUNA DR, LONGBOAT KEY, FL 34228
$1,999,979220 Days on yellowkey MLS ID: A4672554
REDUCED by $10 (0.0%) on 05/28/2026
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2856 Built: 2002Monthly Fee: $542 Tax: $18,656 (2023)Community: Laguna Yacht VillageSingle Family
Taxes:$18,656
Tax Year: 2023
Remarks: Modern Beach Home priced aggressively to sell as the owners are relocating. Ocean Views! Private Dock With Boat Lift On The Bay! Exclusive Beach Community, The Ultimate Beach lifestyle! This raised (16ft.), three bedroom (possible 4th), three bath, three plus car garage home is situated perfectly between the gulf and bay. The exclusive, gated community of Laguna Yacht Village is Longboat Key's best kept secret, consisting of only 8 homes on 9 lots. This quiet, private beach and boating development is unmatched! Relax on your deck, on your boat, at the beach or by the private heated and chilled pool in the knowledge that all the grounds, pool and dock infrastructure are maintained by the HOA. The home has been thoroughly modernized and expanded in 2019/2020 by the current owners. New 25 year aluminum roof, pre-painted hardiplank exterior, enclosed upper deck expanded Master Suite, complete bathroom and kitchen renovations, new water heater (2025), 5 ton HVAC, washer, dryer and kitchen appliances (Sub Zero and Bosch) as well as refinished hardwood floors on the main level and newly laid matching hardwood floors throughout the entire upstairs make this effectively a totally new home. Whilst not required by the current owners, the upstairs loft area could easily be converted into a 4th bedroom. The majority of the work was accomplished by Greyhawk of Bradenton. Other lavish touches include new solid panel doors, new 16 feet wide opening glass slider doors, integrated 180 bottle wine fridge, an oversized 3 plus car garage including new door and the installation of a 10,000 lb boat lift at the deeded private dock. Call today to schedule your private Viewing.
Listing is courtesy of: RE/MAX PALM (941-929-9090)
Listing Agent: Zachary Kaplan (941-321-6796)
1241 GULF OF MEXICO DR #109, LONGBOAT KEY, FL 34228
$1,099,000260 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
Taxes:$14,616
High School: Booker High
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 Agent: Ryan Ackerman, Pa (305-205-7700)
1926 HARBOURSIDE DR #1302, LONGBOAT KEY, FL 34228
$769,000297 Days on yellowkey MLS ID: TB8422578
REDUCED by $20,000 (2.5%) on 05/27/2026
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2606 Built: 1982Monthly Fee: $1,832 Tax: $8,181 (2024)Community: Fairway Bay 1Spa: NoTownhouse
Taxes:$8,181
Remarks: GATED, DEEDED PRIVATE BEACH ACCESS! This is a rare thing to be found on the keys! The main level with plantation shutters and hardwood floors includes the kitchen, dining and living areas. The kitchen has Subzero and Jenn-Air built in stainless steel appliances and granite countertops. A large second story skylight shines natural light through open ceilings onto the main floor dining area. The living area includes a fireplace and provides access to the back screened in lanai. Split bedrooms can be found on the 3rd level of the home. Both bedrooms have ensuite bathrooms and walk in closets. The owners ensuite bathroom includes dual sinks and a shower skylight. A heated pool is only steps away. Take advantage of the gym in the main clubhouse as well as the many amenities offered, including tennis. Membership to the Longboat Key Club is available for the ultimate Longboat Key lifestyle.
Listing is courtesy of: FLAT FEE MLS REALTY (813-642-6030)
Listing Agent: Stephen Hachey (813-642-6030)
1211 GULF OF MEXICO DR #105, LONGBOAT KEY, FL 34228
$1,648,00031 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
$849,900480 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)
2425 GULF OF MEXICO DR #1A, LONGBOAT KEY, FL 34228
$1,595,00081 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)
2819 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$3,699,999245 Days on yellowkey MLS ID: A4669533
REDUCED by $100,000 (2.6%) on 05/26/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1173 Built: 1955 Tax: $36,688 (2024)Community: Coquina BeachSpa: NoSingle Family
Taxes:$36,688
Remarks: BEACH FRONT OPPORTUNITY on Longboat Key! Rare chance to own DIRECT GULF FRONT property on the coveted south end of Longboat Key in Sarasota county. This charming, 1955 beach cottage sustained significant hurricane damage and is now being sold AS-IS for land value only. No HOA fees! Build your dream coastal retreat on this prime GULF-front lot and enjoy breathtaking sunsets, white-sand beaches- just steps to Publix grocery, 1.5 miles to the stunning St. Regis resort, and easy access to nearby St Armand’s dining/shopping, downtown Sarasota, golf, and marinas. You do not want to miss this opportunity to create your own piece of paradise on BEAUTIFUL Longboat Key!
Listing is courtesy of: SERHANT (646-480-7665)
Listing Agent: Jenn Flanders (941-232-0788)
1591 GULF OF MEXICO DR #216, LONGBOAT KEY, FL 34228
$2,750,000281 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
High School: Sarasota High
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
$1,595,000164 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.
4320 FALMOUTH DR #103, LONGBOAT KEY, FL 34228
$499,000140 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
$995,00043 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)
2450 HARBOURSIDE DR #234, LONGBOAT KEY, FL 34228
$1,800,000133 Days on yellowkey MLS ID: A4682324
REDUCED by $200,000 (10.0%) on 05/26/2026
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 3383 Built: 1990Monthly Fee: $153 Tax: $11,852 (2025)Community: Marina BayCondo
Taxes:$11,852
Remarks: Welcome to Marina Bay, one of the most coveted condominium residences within the guard-gated Bay Isles community on Longboat Key. This expansive three-bedroom, three-bath residence offers 3,383 square feet of light-filled living space and exceptional privacy, sharing the floor with only one other residence. Enjoy sweeping panoramic views of Sarasota Bay and downtown Sarasota from the oversized screened balcony—an ideal setting for morning coffee, evening relaxation, and watching the abundant birdlife and marine activity. A second west-facing balcony captures spectacular Gulf sunsets, offering the best of both sunrise and sunset living. Marina Bay delivers a true resort-style lifestyle, featuring a large heated pool, tennis courts, pickleball courts, and a fitness center. Take leisurely strolls along the neighboring marina or around the picturesque Longboat Key Club Harbourside Golf Course. Ideally located, this residence is just a half-mile walk to Publix, CVS, and local shops, and only one mile from the new St. Regis Longboat Key Resort. Membership to the Longboat Key Club is available separately, providing access to world-class golf, dining, tennis, pickleball, and beach amenities. Whether as a full-time residence or an exceptional vacation retreat, this is a rare opportunity to enjoy luxury, convenience, and resort living on Longboat Key—truly, the best of island life.
Listing Agent: Beverly St Hilaire (818-416-2505)
560 HARBOR POINT RD, LONGBOAT KEY, FL 34228
$9,700,000232 Days on yellowkey MLS ID: A4671218
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 5245 Built: 2011Monthly Fee: $802 Tax: $46,237 (2025)Community: Bay IslesSpa: NoSingle Family
Taxes:$46,237
Remarks: Exquisite Palladian-Style Waterfront Estate Located on the serene shores of Sarasota Bay, this home epitomizes elegance and sophistication. Designed by Cliff Scholz and meticulously crafted by Murray Homes, this, 5,300-square-foot masterpiece is situated in a double-gated community offering unparalleled privacy and exclusivity. Perched at the end of a quiet cul-de-sac, the property boasts almost 200 feet of pristine waterfront, with breathtaking views of the downtown Sarasota skyline and a protected deep-water yacht slip. Deeded access to a private Gulf of Mexico beach club enhances the ultimate coastal lifestyle. Inside, the home features an exceptional floor plan with four luxurious bedroom suites and numerous entertainment spaces, including a formal living room, dining room, family room, and a gourmet kitchen equipped for the finest culinary creations. Expansive waterfront terraces, a redesigned viewing porch, and his-and-her offices add to the home's functional elegance. Every detail has been executed to perfection, from the impeccable millwork to the finest finishes throughout. With magical views from every room, this estate embodies class, comfort, and privacy in one of Sarasota's most coveted locations. Experience refined waterfront living at its finest.
Listing Agent: Jonathan Fox, Pa (941-544-6649)
6851 LONGBOAT DR S, LONGBOAT KEY, FL 34228
$1,775,000147 Days on yellowkey MLS ID: A4675356
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2643 Built: 1986 Tax: $9,196 (2024)Community: Longbeach On Longboat KeySingle Family
Taxes:$9,196
Remarks: Welcome to 6851 Longboat Drive South, a completely renovated waterfront retreat offering the best of Longboat Key living. This exceptional residence features four bedrooms and four baths, including a private guest suite above the garage, and office/gym space, making it ideal for hosting family and friends in comfort and style. Designed with coastal elegance in mind, the home showcases light-filled living spaces, a modern open layout and high-quality finishes throughout. The seamless indoor-outdoor flow leads to tranquil waterfront views, ideal for entertaining or unwinding after a day on the water. Boaters will appreciate the private dock, providing direct access to the bay and making it easy to enjoy fishing, cruising or sunset rides right from your backyard. Every detail has been thoughtfully updated, offering peace of mind and turnkey convenience. Just minutes from the Gulf beaches, St. Armands Circle and Longboat Key Club, this property delivers a rare opportunity to own a move-in-ready waterfront home in one of Florida’s sought-after island communities.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Barbara Szumski (941-232-8776)
2600 HARBOURSIDE DR #H-05, LONGBOAT KEY, FL 34228
$300,00032 Days on yellowkey MLS ID: A4694769
Bed: Bath: 0.0 Built: 1983Monthly Fee: $372 Tax: $2,856 (2025)Community: Bay IslesDock-Rackominium
Taxes:$2,856
Remarks: The most convenient dock in the Marina! This 55 x 20 foot slip at Longboat Key Club Moorings is located at the Marina Village along the seawall! Nicely manicured lawn fronts the area at the slip. Club membership is not required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much as a resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean style marina village that includes restaurants, shopping (close to Publix, CVS, and other specialty shops), recreational and social activities, and discreet, on-site maintenance and concierge services. Electric, water and wireless internet access. Longboat Key Moorings is truly a World Class facility. Membership in the Longboat Key Club is available with the option to join anytime. Each vessel must be approved by the Association's Board of Directors prior to entering the Marina. The longest vessel permitted in the slip is 50 LOA; beam depends on the vessel. Call to discuss!
Listing is courtesy of: LBRE LLC (941-383-8383)
Listing Agent: Jennifer Wilson (941-809-7592)
2550 HARBOURSIDE DR #333, LONGBOAT KEY, FL 34228
$1,495,000162 Days on yellowkey MLS ID: A4678404
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 3067 Built: 1990 Tax: $9,185 (2025)Community: Marina BayCondo
Taxes:$9,185
Remarks: Set within a living canopy of mangroves and coastal trees, this BAYFRONT residence invites a more immersive relationship with Sarasota Bay—where filtered light, birdsong, and gentle water movement define everyday living. Behind the gates of Bay Isles on Longboat Key, this approximately 3,000-square-foot waterfront residence offers the ease and scale of a single-family home with the security and convenience of condominium living. With three bedrooms and two-and-a-half baths, the layout lives expansively, enhanced by abundant storage and thoughtful separation of living spaces. Floor-to-ceiling glass sliders in the main living areas and primary suite face east, capturing peaceful sunrise light over Sarasota Bay in a setting best described as park-like waterfront—where mature coastal trees frame the water, creating a serene, private “treehouse” ambiance. Boats glide through the mangrove preserve and lagoon toward open bay waters, accompanied by birdsong and rustling leaves. Two balconies extend the living space outdoors, including a nearly 400 sq ft screened lanai ideal for relaxed coastal living. The primary suite features bay views from bed, terrace access, dual walk-in closets, and a spa-like bath with a freestanding soaking tub, dual vanities, and a glass-enclosed shower. The second and third bedrooms share access to a west-facing balcony, offering sunset light and cross-breezes. The kitchen is both functional and social, featuring quartz countertops, a Sub-Zero refrigerator, generous prep space, a built-in desk nook, mini-fridge and wet bar—well suited for entertaining or casual mornings. A dedicated walk-in laundry room adds practicality with a butcher-block workspace, hutch, and tool cubby. Comfort and peace of mind are prioritized with two A/C zones, new condensers (2025), and two hot water tanks (2021) equipped with a flood-stop device. Brand new carpet and paint. Additional highlights include air-conditioned storage, one assigned garage parking space, and exceptional closet capacity—five linen closets, three pantry closets, and three walk-in closets. Residents enjoy on-site management, a fitness center, tennis and pickleball courts, a heated resort-style pool, car washing area, and EV charging stations. The building features a brand-new roof completed in 2025. Pet-friendly. The location is as compelling as the home itself: secure, serene, and walkable. Adjacent to the Longboat Key Club Marina, and just blocks from Publix, CVS, the post office, and banking, this location allows for a genuinely walkable daily rhythm—rare on Longboat Key. As part of Bay Isles, residents also enjoy access to the Bay Isles Beach Club, a private Gulf-front retreat with gated parking, pavilions, grilling areas, restrooms, and seating for sunset views. Deeded beach access ensures a premier spot on the sand. Membership to the nearby Longboat Key Club is available, offering championship golf, world-class tennis, a full-service spa and wellness center, waterfront dining.
Listing is courtesy of: INVESTMENTS IN SARASOTA (941-894-6059)
Listing Agent: Lee Mirman (941-587-0740)
1105 GULF OF MEXICO DR #401, LONGBOAT KEY, FL 34228
$899,000141 Days on yellowkey MLS ID: A4680369
REDUCED by $100,999 (10.1%) on 05/23/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1172 Built: 1981Monthly Fee: $1,600 Tax: $8,733 (2025)Community: Beachplace IiSpa: YesCondo
Taxes:$8,733
Remarks: Direct Ocean view from this Bright Airy corner unit in desirable building five. Catch the view of the Gulf of Mexico and Sunsets from your balcony. To see this property is to fall in love with easy living! You need to visit this unit to get a sense of the remarkable views , especially the amount of light that permeates the entire interior. Beachplace is a perfect get away on the south end of Longboat Key, and comprise many amenities. Pickle Ball, Tennis, two exercise facilities, Olympic pool, with designated lap lanes, over size hot tub , covered baby pool . Electric car chargers, gas grill, two types of workout facilities on almost 31 acres of lush landscaped grounds. Please visit to see why this building and unit are the best of BEACHPLACE!
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: James Weingart (440-623-9068)
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