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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
$949
Avg. $ / Sq.Ft.
$1,700,558
Med. List Price

Browse Long Boat Key Real Estate Listings

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$3M - $5M

Over $5M

490 Properties Found. Page 15 of 33.

Experience the best of Longboat Key living in this updated 2-bedroom, 2.5-bath townhouse in the exclusive Fairway Bay community, behind the gates of Bay Isles. Offering 1,590 square feet of well-designed living space, this home includes a deeded deep-draft boat slip handling boats up to 40 ft. with no bridges to the bay. The bright interior features light wood floors, recessed lighting, and soaring ceilings with skylights, flooding the space with natural light. The kitchen is equipped with stainless steel appliances, stone counters, a tile backsplash, and a cozy dining nook. Upstairs, both bedrooms offer vaulted ceilings and en-suite bathrooms. The primary suite includes a walk-in shower, dual vanities, and a skylight for added light. The home also has a tandem 2-car garage and an 18' x 11' bonus room for extra storage or a workshop. Enjoy peaceful water views from the screened lanai or take advantage of the private dock for a day on the water. Fairway Bay residents enjoy access to the Bay Isles Beach Club with pristine sand and private lounge areas and it offers deeded beach access, 24-hour security, walking trails, a pool, tennis courts, and a fitness center. For golf and tennis lovers, the Longboat Key Club is nearby, offering world-class courses, tennis facilities, and a full range of resort-style amenities – including the Longboat Key Club Moorings, a full-service deep-water marina with 291 storm-protected slips that can accommodate vessels up to 150-foot. The vibrant shops and dining at St. Armands Circle and Sarasota's cultural attractions are just minutes away.
#A4643392

LONGBOAT KEY

1900 HARBOURSIDE DRIVE 102

2 Beds

2 Baths

2,606 Sq.Ft.

$995,000

MLS#: A4643392

Discover this exquisitely renovated condo with high-impact windows and sliders that lives like a single-family home! This fully furnished 3-bedroom, 2-bath home in the friendly “Harbour Oaks” section of the prestigious Bay Isles community on Longboat Key comes with a private 2 car garage. With just under 2,000 square feet of living space, this residence perfectly combines luxury, comfort, and convenience. This home has been meticulously designed with high-end finishes by an interior designer, offering a sophisticated aesthetic throughout, featuring custom wood paneling, recessed lighting, engineered wood floors, Stark wool carpet in the primary bedroom, and custom window treatments. The 2020 upgraded kitchen features premium stainless-steel appliances and an induction range. Additional thoughtful design elements include cove lighting in the dining room and a wood-burning fireplace with custom Carrera Marble surround. The lanai with a motorized no-see-um bug screen overlooks the Longboat Key Club Harbourside Golf Course, providing breathtaking and comfortable sunset views framed by beautiful trees and lush greenery. For safety, durability and financial peace of mind, this gorgeous second floor residence features recently upgraded high-impact sliders and windows, plus community-wide new roofing and siding. Located in the gated Bay Isles community with 24/7 security, this home is within walking or biking distance to the private and newly renovated Bay Isles Beach Club, the Longboat Key Club Moorings Marina and Portofino restaurant, the Longboat Key Club Pickleball and Tennis Courts, Publix, CVS, as well as to the new Longboat Key St. Regis, which offers exceptional dining options and the vibrant St. Regis Monkey Bar, now open to the public. This remarkable turn-key property with a beautiful community pool and spa offers a rare opportunity to embrace the unparalleled Longboat Key lifestyle. Don’t miss the chance to make it your own.
#A4635715

LONGBOAT KEY

2195 HARBOURSIDE DRIVE 404

3 Beds

2 Baths

2,600 Sq.Ft.

$995,000

MLS#: A4635715

A TRUE FLORIDA DREAM HOME! WALKING DISTANCE TO ONE OF FLORIDA'S MOST BEAUTIFUL BEACH! This 4 bedroom, 3 bath and 2 car garage home is newly renovated thoughout. Step through the door into the spacious open kitchen and living area that expands into a back additional living area large enough for lounging and a pool table. 4 bedrooms and 3 bathrooms offers ample space for family and friends. The open backyard is great to relax and enjoy the Florida weather. The home is located close to wonderful dining and entertainment. The detached 2 car garage offers plenty of space for paddle boards, kayakes or a small boat storage.
#D6142646

LONGBOAT KEY

608 SAINT JUDES DRIVE

4 Beds

3 Baths

2,106 Sq.Ft.

$989,000

MLS#: D6142646

A one of a kind boat slip available for sale with fortified pilings that are plastic coated and an extended finger pier, deep water, protected, yet easy access to Sarasota Bay and the Gulf at Longboat Key Moorings Marina. This is a 154 ft. T-dock/face dock ready to accommodate a yacht; T of D-dock has 2 50s/100 service outlets. D-19 is 74.5 feet, and D-20 is 79.5 feet, because this slip is deeded as two slips, two boats are permitted. Direct access to Sarasota Bay and the ICW with exceptional views of Sarasota Bay. This only deep water marina on the West Coast of Florida is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, Marina village that includes bath house, laundry facilities, restaurant, shopping - close to Publix, CVS, and other specialty shops - recreational and social activities, on-site maintenance and concierge services. Electric, water and wireless internet access at each slip. Free shuttle to St. Armand's Circle. The Marina has everything a boater could need. Membership at the Longboat Key Club is available for an additional fee. This slip will accommodate one or two vessels total 149 feet. Usable beam is 25 feet.
#A4646560

LONGBOAT KEY

2800 HARBOURSIDE DRIVE DRIVE D-19 D-20

None Beds

None Baths

N/A

$985,000

MLS#: A4646560

Welcome to Water Song, your slice of paradise at Harbour Villa Club in prestigious Longboat Key! Water Song is a beautifully maintained top-floor condo with breathtaking water views from nearly every room. Wake up to shimmering water views from your master bedroom and enjoy your morning coffee on the enclosed lanai (216 Sq Ft lanai). Located on the top floor, this two bedroom/ two bath beauty has cathedral ceilings making this quiet residence feel bright, airy, and peacefully tucked away. The 40’ DEEDED BOAT SLIP is just outside your condo so bring your boat or rent the slip for income. Enjoy exclusive access to an array of resort-style amenities: covered private parking space, heated pool and spa, tennis & pickleball courts, kayak storage and launch, and a waterside outside grilling area. Every inch of this home has been lovingly cared for, offering a seamless blend of comfort, elegance, coastal living, and access to culture and the arts. Stroll the sandy white beaches of Longboat Key, watch the sunset, relax by the pool, enjoy a day on the boat, or head out for a paddle. Water Song’s unique proximity to Sarasota, St Armands Circle and Anna Maria Island provides access to world class restaurants, theaters, shopping and the arts. Located in one of the few communities on Longboat Key that allows WEEKLY rentals, this property is a rare investment opportunity or the perfect full-time escape. Don’t miss this exceptional opportunity — where every day feels like vacation! Call now for your private showing!
#A4648854

LONGBOAT KEY

615 DREAM ISLAND PLACE 303

2 Beds

2 Baths

1,509 Sq.Ft.

$975,000

MLS#: A4648854

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

1,024 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

1,794 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

2,432 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

2,432 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

1,485 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

2,889 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

2,286 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

1,603 Sq.Ft.

$939,000

MLS#: A4648009

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