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Long Boat Key

One of the most popular communities provided by Michael Graf

Long Boat Key

About Long Boat Key

Longboat Key, Florida, is a tranquil paradise that offers the perfect blend of luxurious living and natural beauty. Nestled between the sparkling waters of the Gulf of Mexico and Sarasota Bay, residents enjoy stunning beaches, picturesque sunsets, and a laid-back, island lifestyle. The community is renowned for its upscale amenities, including gourmet dining, boutique shopping, and world-class golf courses, all while maintaining a quaint, small-town charm. With year-round warm weather, ample outdoor recreational activities, and a strong sense of community, Longboat Key is an ideal place for both relaxation and adventure, making it a highly desirable destination for those seeking a serene coastal retreat.
One of the most popular communities provided by Michael Graf
490
# of Listings
2
Avg # of Bedrooms
$954
Avg. $ / Sq.Ft.
$1,709,482
Med. List Price

Browse Long Boat Key Real Estate Listings

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Under $250,000

$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

116 Properties Found. Page 2 of 8.

Nestled in the heart of Longboat Key, this exceptional two-bedroom, two-bathroom beachfront condo offers a rare blend of luxury, comfort, and high rental potential. Situated within the meticulously maintained Seagrape Inn, this turnkey furnished unit is an investor’s dream, boasting a potential gross annual revenue of $108,000 and a net operating income of $66,000. The Seagrape Inn's lush landscaping and upscale tropical ambiance create an idyllic setting along the stunning Gulf of Mexico, perfect for both personal enjoyment and income generation. Amenities at Seagrape Inn include a private entrance to each condo, a private heated pool, a private beach area with lounge chairs and umbrellas, on-site laundry and ice machine, upgraded Wi-Fi throughout the resort, cable TV, a gazebo with a gas BBQ grill, and beach towels and linens. Unit 7, perched on the second floor, provides breathtaking views of the ocean and the inviting pool below. Upon entry, the condo exudes sophistication, with a thoughtfully designed living space that seamlessly connects the living room, dining area, and upgraded kitchen. The kitchen, recently renovated to perfection, features new cabinets, countertops, recessed lighting, plumbing fixtures, and state-of-the-art appliances. The entire unit has been enhanced with new waterproof LVP flooring, fresh interior paint, and modern light fixtures, ensuring a contemporary and elegant aesthetic throughout. Both bedrooms are tastefully furnished, offering serene retreats after a day at the beach. The bathrooms have been completely remodeled, showcasing new vanities, tile work, shower doors, and plumbing fixtures. Step onto the screened balcony to savor unparalleled views of the ocean, pool, and lush greenery—a perfect spot to relax and soak in the tranquil surroundings. Beyond the condo's exquisite interior, significant exterior improvements have been made, including the installation of hurricane windows and doors, new deck waterproofing, and exterior painting. The convenience of a designated parking spot adds to the property’s appeal. Located in a prime area of Longboat Key, this condo provides easy access to the beach, Gulf, and nearby restaurants and shops. Whether you're seeking a lucrative investment or a luxurious personal retreat, this beachfront condo offers an extraordinary opportunity to experience the best of coastal living in an unparalleled location.
#N6136477

LONGBOAT KEY

5125 GULF OF MEXICO DRIVE 7

2 Beds

2 Baths

961 Sq.Ft.

$975,000

MLS#: N6136477

Waterfront Beauty~ Coastal Condo with Panoramic Bay Views! Experience the pinnacle of island living in this turnkey furnished, recently refreshed 3-bedroom, 2-bath condo in the highly desirable Pelican Harbour & Beach Club on Longboat Key. Located on the second floor, this light-filled end unit offers sweeping Sarasota Bay views from the living room, primary suite, and your private screened-in balcony—ideal for morning coffee or sunset cocktails. With over 1,600 sq ft of coastal-inspired living space, this residence features a spacious living room, tranquil dining area, and a serene owner’s suite with lanai access and a beautifully renovated ensuite bath. Recent updates include new carpet, furniture, recessed lighting, professionally painted interiors, mounted TVs, and a new AC and water heater (2024). Additional conveniences include in-unit laundry and covered parking. Pelican Harbour offers resort-style amenities: 200 feet of private deeded beach with new lounge chairs, Heated pool & clubhouse, Marina with boat slips (up to 28 ft) & kayak launch, Tennis & pickleball courts, Pet-friendly. Professionally managed, the community features new roofs, hurricane-rated carports. Ideally located mid-key, you're just minutes from St. Armands Circle, Bayfront Park, and the new St. Regis Resort. Whether you're seeking a full-time residence, seasonal escape, or investment opportunity, this bayside retreat offers the perfect blend of luxury, comfort, and convenience.
#A4653045

LONGBOAT KEY

4234 GULF OF MEXICO DRIVE G2

3 Beds

2 Baths

1,636 Sq.Ft.

$975,000

MLS#: A4653045

Seasonal Income Awaits - Turnkey Duplex in the Heart of Longboat Key 'Tis the season for a lucrative investment! This fully renovated duplex in the heart of Longboat Key offers the perfect blend of income potential and coastal charm. Featuring two separate units, each with 2 bedrooms and 2 bathrooms, this property is sold fully turnkey, so you can start generating rental income immediately. Step outside to a spacious backyard and inviting outdoor living space, perfect for relaxation or entertaining. Best of all, you're just seconds away from the pristine beaches of Longboat Key, where soft sands and breathtaking sunsets await. Whether you're looking for a high-performing rental property or a personal retreat with built-in income, this is an opportunity you don't want to miss! Prime Location | Turnkey Investment | Minutes to the Beach
#A4650543

LONGBOAT KEY

578-580 COMPANION WAY

4 Beds

3 Baths

1,792 Sq.Ft.

$950,000

MLS#: A4650543

Seasonal Income Awaits – Turnkey Duplex in the Heart of Longboat Key ’Tis the season for a lucrative investment! This fully renovated duplex in the heart of Longboat Key offers the perfect blend of income potential and coastal charm. Featuring two separate units, each with 2 bedrooms and 2 bathrooms, this property is sold fully turnkey, so you can start generating rental income immediately. Step outside to a spacious backyard and inviting outdoor living space, perfect for relaxation or entertaining. Best of all, you’re just seconds away from the pristine beaches of Longboat Key, where soft sands and breathtaking sunsets await. Whether you're looking for a high-performing rental property or a personal retreat with built-in income, this is an opportunity you don’t want to miss! Prime Location | Turnkey Investment | Minutes to the Beach
#A4625887

LONGBOAT KEY

578-580 COMPANION WAY

None Beds

None Baths

0.19 acres

$950,000

MLS#: A4625887

* * DO NOT MISS OUT ON THIS LONGBOAT SPECIAL * * MULTIPLE USES ARE AVAILABLE TO YOU * * Presently set up as a 3 bedroom / 2 bathroom / 2 car garage home with a formal living room. Completely updated kitchen that provides access to a family room and attached reading room. Oversized 2 car garage with a FULL INLAW SUITE above the garage. INLAW SUITE has a huge living room. Kitchen that opens to dinette. One bedroom and a one bathroom. It has two separate entrances (one from inside home and one with direct access to outside). Large balcony off the living room. FOR THE DEVELOPER - Large quarter acre lot that is 123' wide. Lots of space to build that dream home. Previous marketing indicates private deeded beach access (this statement is not warranted, and buyer needs to verify). EVERYONE WANTS TO LIVE ON LONGBOAT KEY. This is paradise at its best! Multiple golf courses on the island and easy access to more on the mainland. Go north and enjoy Bradenton Beach and Anna Maria and all that they have to offer. Go south and enjoy St. Armands Circle or Downtown Sarasota. All of the shopping and restaurants you could want! If you are a boater, multiple marinas locally to handle all of your boating needs. * * PLEASE NOTE * * It is buyer’s responsibility to verify all information. Information posted in MLS or any marketing information is not guaranteed.
#U8252397

LONGBOAT KEY

651 JUNGLE QUEEN WAY

4 Beds

3 Baths

2,242 Sq.Ft.

$950,000

MLS#: U8252397

Seasonal Income Awaits – Turnkey Duplex in the Heart of Longboat Key ’Tis the season for a lucrative investment! This fully renovated duplex in the heart of Longboat Key offers the perfect blend of income potential and coastal charm. Featuring two separate units, each with 2 bedrooms and 2 bathrooms, this property is sold fully turnkey, so you can start generating rental income immediately. Step outside to a spacious backyard and inviting outdoor living space, perfect for relaxation or entertaining. Best of all, you’re just seconds away from the pristine beaches of Longboat Key, where soft sands and breathtaking sunsets await. Whether you're looking for a high-performing rental property or a personal retreat with built-in income, this is an opportunity you don’t want to miss! Prime Location | Turnkey Investment | Minutes to the Beach
#A4623518

LONGBOAT KEY

578-580 COMPANION WAY

4 Beds

None Baths

1,792 Sq.Ft.

$950,000

MLS#: A4623518

One or more photo(s) has been virtually staged. Front-row Gulf views and beachfront living set this 2BR/2BA residence apart at the Islander Club of Longboat Key. With over 1,235 sq. ft. of light-filled space set just above the sand, savor sweeping vistas of the shoreline and SPECTACULAR SUNSETS over the Gulf. White tile floors and neutral tones throughout create a sense of openness that draws focus to the stunning natural surroundings. A wall of glass sliders in the living room opens to the expansive terrace, where salty breezes and soft waves make every day feel like a vacation. The terrace spans the full width of the residence and can be accessed from both bedrooms, blending indoor and outdoor living in perfect balance. It’s a space with strong potential to match the lifestyle it serves. The primary suite is bathed in natural light, with floor-to-ceiling windows, a walk-in closet and a private bath with a separate water closet. The guest bedroom is equally inviting, with generous space and direct Gulf views. Islander Club is a highly desirable Gulf-front community offering resort-style amenities, including a beachfront pool, tennis courts, a fitness center, library, and billiards room, along with a secure, gated entrance. Conveniently located in the heart of Longboat Key, you're just minutes from St. Armands Circle, downtown Sarasota, and everything the area has to offer. Additionally, while membership to the Longboat Key Club is not required, it is available for residents seeking enhanced amenities. The club offers Restaurants, lounges, beach & poolside facilities, spa, fitness center, tennis courts, and access to 45 holes of championship golf.
#A4649187

LONGBOAT KEY

2301 GULF OF MEXICO DRIVE 36N

2 Beds

2 Baths

1,235 Sq.Ft.

$949,000

MLS#: A4649187

Experience the ultimate in island living in the highly sought-after and prestigious Harbor Oaks community on Longboat Key. This one-story, 3-bedroom, 2.5-bath residence spans 2,219 sq. ft. and offers a host of desirable features—including a private pool, 2-car garage, and deeded beach access through the exclusive Bay Isles Beach Club. A new roof (2025) and fresh interior paint ensure peace of mind and a move-in-ready experience. High ceilings fill the home with natural light, enhancing the spacious feel throughout. The expansive living room, anchored by a wood-burning fireplace, seamlessly connects to the outdoor living area via pocket sliding glass doors, opening to two large screened lanais—ideal for both relaxing and entertaining. The chef’s kitchen is outfitted with granite countertops, stainless steel appliances, rich wood cabinetry, a breakfast bar, and a skylight for added brightness. The primary suite is a private retreat featuring a walk-in closet, two additional closets, updated master bath, and sliding doors leading to the terrace. A guest suite with en suite bath provides comfort and privacy for visitors. Additional highlights include an interior laundry room with sink, a newer AC unit (2018), and natural gas line for adding a pool heater. All furnishings are included. Residents of Harbour Oaks enjoy a resort-style lifestyle with access to a community pool, spa, and lushly landscaped surroundings—just minutes from Longboat Key’s vibrant Town Center. As part of Bay Isles, you’ll have exclusive access to the Bay Isles Beach Club, a private, gated Gulf-front oasis with a pavilion, picnic areas, BBQ grills, beach chairs, restrooms, and ample parking—perfect for sunset viewing or relaxing on Longboat Key’s pristine white sands. Optional membership opportunities at the Longboat Key Golf & Tennis Country Club and Harbourside Moorings deep-water slips offer even more ways to elevate your coastal lifestyle.
#A4656539

LONGBOAT KEY

2181 HARBOURSIDE DRIVE 1403

3 Beds

2 Baths

2,219 Sq.Ft.

$949,000

MLS#: A4656539

Sought after mid-key cottage home with DEEDED BEACH ACCESS on the barrier island of Longboat Key.  Entering the home, you are greeted by terrazzo floors, wood beam ceilings and a tile accented gas fireplace in the large living room.  An additional room overlooking screened in pool can be used as an office, exercise room or extra space for guests. Newly renovated kitchen with wood cabinets, quartz countertops, new sink and fixtures.  Bathrooms have been completely renovated with beautiful walk-in tiled showers. A built-in bookcase in the living room adds charm with plantation shutters, accent lighting and ceiling fans throughout. Completely restored home by licensed general contractor and professionally mitigated after hurricane Helene flood damage. The house shares a driveway and deeded beach access with 5920 Gulf of Mexico Drive making it a perfect guest house or family compound when purchased together. Another possibility is to use one as as a rental for an ongoing revenue stream. The property is being sold As-Is (use FAR-BAR-ASIS-7.
#A4651805

LONGBOAT KEY

5924 GULF OF MEXICO DRIVE

2 Beds

2 Baths

1,359 Sq.Ft.

$949,000

MLS#: A4651805

Enjoy comfortable, coastal living in this well-appointed 2BR/2BA residence on the sought-after south end of Longboat Key. With over 1,500 sq. ft., this home features a neutral color palette and thoughtful design that enhances the natural beauty just outside. The kitchen offers classic white cabinetry with glass accents, granite countertops, stainless-steel appliances, and recessed lighting. A breakfast bar opens to the dining area, which flows into the spacious living room. Large sliding glass doors lead to the terrace, offering views of Sarasota Bay, the peaceful community lake and fountain, and the Gulf of Mexico - perfect for watching sunsets. The primary suite is light and airy, with terrace access and a full wall of glass. The en suite bath includes dual vanities, a walk-in shower, and a separate water closet. The guest suite also features generous space, plenty of storage, and its own full bath. Beachplace is a 31-acre gated community known for its mid-century modern design by Tim Seibert and its outstanding amenities: private beach access, a Jr. Olympic-sized pool, spa, kiddie pool, clubhouse with social activities, two fitness centers, sauna, tennis and pickleball courts, EV charging, and grilling stations. Rentals are allowed 12 times per year with a 30-day minimum. Residents also enjoy proximity to the prestigious Longboat Key Club, offering an exceptional lifestyle with 45 holes of championship golf, a world-class tennis center, a full-service marina, spa and wellness center, fine dining, and a private beach club - making it easy to enjoy the best of resort-style living just moments from home.
#A4648009

LONGBOAT KEY

1095 GULF OF MEXICO DRIVE 503

2 Beds

2 Baths

1,503 Sq.Ft.

$939,000

MLS#: A4648009

Experience the charm of historic Longboat Key living in this delightful 3-bedroom, 3-bathroom single-family home – Coastal Haven Cottage! Nestled in the heart of the village, you're just a short stroll away from pristine Gulf beaches and the area's renowned waterfront restaurants. Enjoy the convenience of golf cart access throughout the village and a quick ride over the bridge to explore the vibrant shops and beaches of Anna Maria Island. Back at home, unwind in the cozy outdoor area, complete with comfortable seating, a dining table for al fresco meals, and ample storage for all your beach and fishing gear. ROOM FOR A POOL - SEE PHOTO OF POOL! Offering a blend of classic charm and modern updates, including a 2020 roof, 2022 AC, new stainless-steel appliances, impact doors and windows, this home invites you to embrace the island life in this charming Longboat Key retreat. Additional offerings include covered carport and ample parking, fenced in yard, designer furnishings and finishes, and future rentals in place. Sold turnkey furnished, it's the perfect opportunity to immediately enjoy the coveted Longboat Key lifestyle!
#A4636248

LONGBOAT KEY

600 FOX STREET

3 Beds

3 Baths

1,427 Sq.Ft.

$899,999

MLS#: A4636248

Build Your dream waterfront home on North Longboat Key! Discover an exceptional opportunity to create your custom coastal retreat on this build-to-suit lot with 120 feet of waterfront frontage. The property is primed for development, with a permit filed and approved. Architectural plans by Sweet Sparkman Architecture and Interiors, renowned for their innovative designs that harmonize modern luxury with the beauty of Florida's coastal landscapes. The thoughtfully designed floor plan ensures a seamless flow for everyday living and entertaining, capturing breathtaking water views from key living areas. Whether you’re relaxing indoors or stepping out to enjoy the vibrant outdoor spaces, this home has been envisioned to maximize its unparalleled waterfront location. Key features include a new seawall in 2023 that provides a solid foundation for waterfront living. Deeded beach access, just a short distance away, offers private enjoyment of pristine sandy shores on Longboat Key. Boating enthusiasts will appreciate the ample frontage for a dock and boat, providing easy access to Sarasota Bay and beyond. On sought-after North Longboat Key, the property offers proximity to acclaimed restaurants like Shore, Whitney’s and Mar Vista, ensuring dining and entertainment are always nearby. This is your chance to bring a remarkable vision to life in one of Florida’s desired locations. Schedule your private showing today and imagine the possibilities.
#A4633465

LONGBOAT KEY

720 TARAWITT DRIVE

None Beds

None Baths

0.25 acres

$899,000

MLS#: A4633465

Experience the epitome of Island living in this meticulously kept and beautifully renovated retreat located in the beachfront community of The Westchester on Longboat Key. This ground floor walk-out, 2 bedroom, 2 bath residence is a true coastal oasis all done up in seaside hues. The gorgeous kitchen opens to the large living/dining area and the spectacular views can be seen through impact resistant sliding doors that open wide for easy indoor/outdoor living. Step out to one of two private screened in lanais and you'll find the perfect spot to enjoy a morning coffee or an evening beverage while watching the sunset. This home is being offered with all the designer furnishings, so all you’ll need to do is bring your flip flops. Here you will find a remarkable quality of laid back island life with the gorgeous beach that stretches for miles, 2 sparkling pools, a tennis and pickleball court, a shuffleboard court, and a lovely clubhouse. An on site manager is available Monday through Friday. If you're ready for more, fine dining and nightlife in the world famous St. Armands Circle and the cultural mecca of downtown Sarasota are just a short drive away. Important to note: The Westchester has completed its Milestone Inspection and all assessments have been paid in full.
#A4620656

LONGBOAT KEY

4825 GULF OF MEXICO DRIVE 105

2 Beds

2 Baths

1,393 Sq.Ft.

$899,000

MLS#: A4620656

Exceptional opportunity to own this beautiful first-floor condominium at The Promenade, offering the perfect balance of comfort, and coastal charm with nearly 400 feet of private beach frontage and partial views of the Gulf of Mexico from almost every room. This spacious two-bedroom, two-bathroom split floor plan features a bright, open layout ideal for entertaining or relaxed living. The kitchen flows seamlessly into the expansive living and dining areas, creating a connected and inviting space. Enjoy stunning northwest sunset views from the comfort of the great room or step outside to the private balcony for a peaceful retreat overlooking the Gulf. The elegant primary suite offers balcony access, a large walk-in closet, and a spa-like en-suite bath with a soaking tub and walk-in shower. The generously sized guest bedroom is perfect for visitors or can be easily adapted as a home office or hobby room. The Promenade offers a true resort-style experience with a 24-hour staffed gatehouse, full concierge services, and secure under-building assigned parking. Residents enjoy a heated Gulf-front pool and spa, a spacious sundeck with shaded gazebo and grilling area, four Har-Tru tennis courts, a well-equipped fitness center, a craft room, and inviting social spaces. Private beach access lined with charming tiki huts completes the picture of effortless coastal living. Don’t miss this rare opportunity to embrace the ultimate Longboat Key lifestyle, where every day feels like a vacation
#A4658394

LONGBOAT KEY

1211 GULF OF MEXICO DRIVE 105

2 Beds

2 Baths

1,598 Sq.Ft.

$899,000

MLS#: A4658394

One or more photo(s) has been virtually staged. PRICE IMPROVEMENT!! WATERFRONT GEM ON LONGBOAT KEY – Priced UNDER $1M & Renovation Loan Eligible! This is your chance to own a waterfront home on Longboat Key for under $1 million! Opportunities like this are rare, and this property is priced to sell fast. Featuring 2 bedrooms, 2 bathrooms, and a 1-car garage, this home also includes a separate 1-bedroom, 1-bathroom GARAGE APARTMENT with its own entrance—perfect for SHORT TERM RENTALS or guest accommodations. Sitting directly on a CANAL with room to dock a boat, this home is a dream for boaters and beach lovers alike. The 120 feet of reinforced seawall ensures lasting waterfront stability. Enjoy DEEDED BEACH ACCESS, just a short stroll away, where you can witness the magic of turtle nesting season. Walk to dog-friendly Durante Park, the scenic shores of Sarasota Bay, and some of Longboat Key’s most popular restaurants, including Lo’Key and Harry’s Continental Kitchen. Cannon’s Marina is nearby for all your boating needs, and the trolley provides easy access to Anna Maria Island. The home boasts a 2024 AC and a 5-year-old tile roof, giving you peace of mind on major updates. The private outdoor space is perfect for soaking up Florida’s year-round sunshine. Renovation Loan Eligible – Plus an Incredible Build Opportunity! This property qualifies for a renovation loan, allowing you to finance both the purchase and renovations—an incredible opportunity to customize your dream home while keeping costs manageable. Looking for even more space? The vacant lot next door is also for sale, making this a rare chance to tear down and build a custom waterfront compound. Waterfront. Deeded beach access. Room for a boat. Rental potential. And all for UNDER $1 MILLION! This is an **unbeatable opportunity** in one of the most desirable locations on the Gulf Coast. Don’t miss out—schedule your showing today!
#TB8368182

LONGBOAT KEY

636 TARAWITT DRIVE

2 Beds

2 Baths

1,248 Sq.Ft.

$895,000

MLS#: TB8368182

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