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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
511
# of Listings
2
Avg # of Bedrooms
$856
Avg. $ / Sq.Ft.
$1,506,912
Med. List Price

Browse Long Boat Key Real Estate Listings

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$500,000 - $1M

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$3M - $5M

Over $5M

511 Properties Found. Page 29 of 35.

BAYPORT BEACH and TENNIS CLUB, a Gulf to Bay, FULLY FURNISHED 2/2 residence. Bayport is an award winning community situated in the heart of Longboat Key. A friendly, popular, residential enclave of 136 quality-constructed homes on 27 picturesque acres of impeccably maintained grounds. Tastefully decorated and well maintained with over 1600 square feet of living area; perfect for entertaining friends, relaxing with a morning coffee or your favorite beverage on a lushly landscaped private garden patio. Bordered by the Gulf of Mexico to the west with 1200 feet of private Gulf beach and Sarasota Bay to the east. Enjoy an active island lifestyle with 4 HarTru tennis courts, an enormous heated pool, a fishing pier, kayak facilities, Bocce court and nature trails. The spacious clubhouse, with fitness room and full kitchen, hosts a number of social activities. A short walk to the Gulf of Mexico for morning beachcombing or memorable sunsets. Minutes to grocery and other shops as well as the area's finest restaurants. Bayport Beach and Tennis Club is a special island property with remarkable beauty and fabulous amenities.
#TB8335223

LONGBOAT KEY

832 BAYPORT WAY 832

2 Beds

2 Baths

1,601 Sq.Ft.

$10,000

MLS#: TB8335223

***NEW VACATION RENTAL LISTING** * Booked Dec1st-March 31st 2026. Welcome to your amazing beachfront Longboat Key at Sunset Beach vacation. Sunset Beach is a 3 building complex located directly on Gulf of Mexico and it's powdery sandy beach and perfect sunset views. Guests will find a large gulf front pool, spa, community room for social gatherings, fire pit and BBQ grill. You are welcome to beach chairs along the private beach. Under-building assigned parking directly across from security coded entry lobby with elevator and mailboxes. Plenty of guest parking inside the welcome security gates. Full time maintenance crew keeps the grounds immaculate. Wake up to beach and water views from Living room, both bedrooms and terrace. The apartment has an fully appointed updated kitchen with plenty of storage and counter space. Renovations include freshly painted in 2023, new high impact windows and sliders, plantation shutters, tiled flooring, closet organizers, new living and dining room furniture, decor and linens. Utility room with Maytag washer and dryer. Sunset Beach is currently replacing all lobby and hallway flooring. Just minutes to St Armand’s Circle or Lido Beach for shopping, fine dining or laying at the public beach with all your favorite people. Longboat is known for their waterfront golf, fine dining and luxury resorts. In fact, its 12 miles of white sand beaches have helped to make this a luxury Gulf Coast resort community. There are numerous Activities and Attractions in the Sarasota/Bradenton/Siesta area. -Just a few of the many treasures and cultural events are Benderson Park, Mote Marine Aquarium, Ringling Museum of Art, fishing charters out of Marina Jack's, Florida's Largest Wildlife Rescue / Rehabilitation Center with the Pelican Man, Selby Botanical Gardens, and the Van Wezel.
#A4584050

LONGBOAT KEY

2109 GULF OF MEXICO DRIVE 1203

2 Beds

2 Baths

1,463 Sq.Ft.

$10,000

MLS#: A4584050

GORGEOUS SHORT TERM RENTAL!!!! Bayport Beach & Tennis Club is an amenity-rich community at sea's edge and is situated in the middle of Longboat Key. This 2 bedroom, 2 bathroom fully FURNISHED rental is tastefully and brilliantly decorated. This residence offers a wonderful retreat as a Seasonal rental or a shorter Monthly respite. Bayporters' enjoy an active island lifestyle with 4 Har Tru tennis courts, a Jr. Olympic sized (heated) pool, private fishing pier, kayak facilities, Bocce court and amazing nature trails. The spacious clubhouse, with fitness and full kitchen, hosts a number of social activities. Simply walk across the street to private beach on the Gulf of Mexico for morning beachcombing, surf casting or memorable sunsets.
#T3527649

LONGBOAT KEY

838 BAYPORT WAY 838

2 Beds

2 Baths

1,601 Sq.Ft.

$10,000

MLS#: T3527649

Luxury Living meets Modern Coastal at Gulf Front Haven, a beautifully updated, modern, ocean view floorplan that sits right on the beach at Longboat Key, one of the Gulf Coasts Premier Living Areas!  This home is located right in the heart of the Players Club, one of Longboat Keys most luxurious communities with all the amenities to make your stay great!! The condo is located on the 3rd Floor with breathtaking views of the Gulf Coast Ocean!  Experience a 2 Bedroom, 3 Bath Combo home with all the open floor plan that you and your family could need.  The beautifully designed, modern kitchen, is equipped with all the appliances you will need to make your trip a success, including barstool seating for four, all new stainless steel appliance's, and induction burner top oven. The Master Bedroom is equipped with a luxurious King Sized Bed, Flat Screen TV, and sliding glass doors that open directly to a private lanai overlooking the ocean.  The Master Bathroom is also equipped with a His/Her Sink, giving you the space you need to get ready to enjoy your day.   The second bedroom is equipped with two, very comfortable, full sized beds, giving everyone a comfortable space to have plenty of room for rest and relaxation.  Your guests enjoy their own bathroom as well, fully equipped with all the amenities and their own private shower. There is an all enclosed, private sitting room and office space that overlooks the beautiful courtyard of the Players Club.  The sofa pulls out into a full sized mattress, giving you room for everyone! The Players Club Complex is a luxury living community in Longboat Key.  They give you as a renter access to all the amenities of the community, up to and including:  Private Beach Access included with Beach Chairs and Umbrellas, private pool and spa area, putting greens, tennis courts. fitness center, clubhouse, library, and others!   Application must be filled out prior to arrival to register with the community itself.  If interested in long term, please inquire directly with the property management company for pricing.   No Smoking, No Pets All Amenities included at No Extra Charge!
#A4671205

LONGBOAT KEY

1445 GULF OF MEXICO DRIVE 305

2 Beds

2 Baths

1,957 Sq.Ft.

$10,000

MLS#: A4671205

Available beginning June 1st, 2026. Welcome to beachfront paradise on Longboat Key! This outstanding location offers a rare opportunity to enjoy coastal living with breathtaking views of the shoreline. Nestled along the pristine shores of Longboat Key, this three-bedroom, three-bathroom home invites you to experience the ultimate beachfront lifestyle. Relax under the sun, unwind to the sound of waves just steps from your door, sip your morning coffee with panoramic ocean views, and take in unforgettable sunsets — all from your own slice of paradise. Located directly on the beach, this property offers a true coastal tropical oasis. You're just minutes from Publix for all your grocery needs, and only 1.5 miles from the Longboat Key Bayfront Park, where you can enjoy pickleball, tennis, shuffleboard, basketball, a playground, swings, and scenic walking paths. Looking for shopping and dining? St. Armands Circle is just a 5-mile drive away, offering a celebrated selection of restaurants and boutiques. The 2026 summer and fall are available! Rates are: $10,000 for June, $10,000 for July, $10,000 for August, $8,000 for September, $8,000 for October, $10,000 for November, and $10,000 for December. Taxes apply. Call today to reserve!
#A4667245

LONGBOAT KEY

2823 GULF OF MEXICO DRIVE

3 Beds

3 Baths

1,744 Sq.Ft.

$10,000

MLS#: A4667245

Pleasantly perfect! This spacious well appointed 2 bedroom, 2 bathroom condo is fully furnished, so just bring your beach gear and move right in. Bayport Beach and Tennis Club offers a wonderful pristine private beach exclusive for your enjoyment, with Intracoastal Bay Access. Tim Seibert, designer of Bayport, sought to create private villas surrounded by lush landscaped tropical gardens, and he did this on 27 beautiful acres. Bayport amenities include a junior Olympic size swimming pool, 4Har-Tru tennis courts, a private fishing pier, kayak launch and storage, bocce court, golf practice net, club house, library, piano, and a wonderful fitness center. On site management and full time landscape maintenance is also provided. . If you are looking for a resort lifestyle, with every imaginable amenity, and a fantastic location. AVAILABLE - DECEMBER 1ST, 2024
#T3492091

LONGBOAT KEY

805 BAYPORT WAY 805

2 Beds

2 Baths

1,456 Sq.Ft.

$10,000

MLS#: T3492091

LONGBOAT KEY'S SEAPLACE Enjoy the tropical sea breezes and the magical Water Views from this custom designed THREE BEDROOM spacious corner unit. Beautiful wrap around Lanai terraces with panoramic scenery of the GULF OF MEXICO. Primary Suite-King Bed, Bedroom #2 Suite-King Bed, Bedroom #3- two twin beds. Seaplace is located close to shopping and restaurants and just minutes to ST Armand's Circle and Downtown Sarasota. The SEAPLACE community features include half mile of beach front, two large swimming pools,two spas, three Har-Tru Tennis courts, clubhouse, fitness center, barbecue grills, and a one mile walking trail.
#A4565848

LONGBOAT KEY

1925 GULF OF MEXICO DRIVE 309

3 Beds

3 Baths

2,698 Sq.Ft.

$10,000

MLS#: A4565848

Welcome to your new Beach House Sanctuary!! Completely renovated Island home located 4 houses off Tarawitt point on a large 90x125ft lot! Coveted lifestyle and location on a deep water canal in the heart of Longboat Key! This waterfront home has 125ft of seawall docking for a boat up to 30 ft. plus a jet ski lift and room for other water toys. Catch bait and start fishing in less than 30 minutes! Intracoastal waterway 50 yards from the point of the canal. Direct access to Sarasota Bay with no bridges! This meticulously maintained home has three bedrooms, two full baths and one half bath plus a one car garage. Open floor plan with spectacular views of Sarasota Bay. Large master bedroom includes a seating area, tv, a large walk-in-closet and a bath with a double vanity and a large walk-in shower. The kitchen and living room open onto a porch with Bay views. The residence was renovated in 2022 and has a new roof and new windows and doors. Other upgrades include granite countertops and new appliances, updated bathrooms, new flooring, freshly painted interior and exterior plus a hot tub. Deeded beach access is directly across Tarawitt Dr for enjoying the beautiful beach and warm Gulf waters on the shores of Longboat Key. The location is walking distance to Harry's Restaurant, Euphemia Haye, The Lazy Lobster, and biking distance to The Shore or Mar Vista. Plus it's an easy drive to Anna Maria, St. Armands Circle and Sarasota.
#A4663797

LONGBOAT KEY

825 TARAWITT DRIVE

3 Beds

2 Baths

1,882 Sq.Ft.

$10,000

MLS#: A4663797

Bright and Spacious! This lovely 2 bedroom, 2 bathroom furnished condominium is nestled comfortably in a lush tropical setting with a spacious eat-in kitchen that is open to the living area. Elegantly furnished in a natural color pallet. The master suite is tastefully decorated, with a built in vanity, double sinks and his and her closets. It also features a small alcove with a desk with access to a private screened in patio with gulf view. Additionally there is a large private deck for sunbathing, relaxing or enjoying an outdoor BBQ! Bayport Beach and Tennis Club is directly across from the sandy beach of the Gulf of Mexico with 1200 feet of private beach. Amenities include (4) Har-tru tennis courts, one of the largest swimming pools on the island and a clubhouse with kitchen facilities for private parties and social functions, fitness center, a fishing pier on the bay, a kayak launch and nature paths all on 27 lushly landscaped acres. NOW AVAILABLE JULY - DECEMBER 2024
#T3464450

LONGBOAT KEY

720 BAYPORT WAY 720

2 Beds

2 Baths

1,260 Sq.Ft.

$10,000

MLS#: T3464450

LOCATION, LOCATION, LOCATION!!!!! Gorgeous beach front condo in the sought after Longboat Key community of the Players Club. This light and bright turnkey furnished condo has two bedrooms, two bathrooms, living room/dining room combination, sitting area off the living room, separate sitting room at the front entrance, three lanais with ocean views and a laundry closet with full sized washer and dryer. The primary bedroom has a king sized bed, on suite bathroom with double sinks and a stall shower, and walk in closet and a ocean view lanai with lounge chairs and table for enjoying the view. The guest bedroom has two twin beds and ocean views from two large windows. Guest bathroom has a stall shower. Front entry is set up as a sitting area with a queen sized murphy bed. The Player Club is abound with amenities. The amenities include a gated entry, beach access, putting green, heated community pool with spa, BBQ grills, tennis, clubhouse, fitness center and large meeting room. No pets allowed. Three month minimum rentals only due to the Association. CALL TODAY. This is not one to miss!!
#A4548403

LONGBOAT KEY

1485 GULF OF MEXICO DRIVE 109

2 Beds

2 Baths

1,839 Sq.Ft.

$10,000

MLS#: A4548403

GORGEOUS LONG TERM RENTAL!! Bayport Beach & Tennis CLub is an amenity-rich community at sea's edge and is situated in the middle of Longboat Key. This 2 bedroom, 2 bathroom fully furnished rental is beautifully appointed. This residence offers a wonderful retreat as a annual. Bayporters' enjoy an active island lifestyle with 4 Har Tru tennis courts, a Jr. Olympic sized (heated) pool, private fishing pier, kayak facilities, Bocce court and amazing nature trails. The spacious clubhouse, with fitness and full kitchen, hosts a number of social activities. Simply walk across the street to the private beach on the Gulf of Mexico for a morning of beachcombing, surf casting or memorable sunsets. Please contact Agent for availability. NOW AVAILABLE STARTING 8/1/2024
#T3488628

LONGBOAT KEY

522 BAYPORT WAY 522

2 Beds

2 Baths

1,260 Sq.Ft.

$10,000

MLS#: T3488628

Escape to your own private garden oasis on beautiful Longboat Key. This home features lush tropical landscaping, a sparkling heated pool, and a spacious screened lanai perfect for outdoor dining and relaxation. Inside, enjoy a chef’s kitchen with premium appliances, including a Wolf range, and newly updated bedrooms and baths — the primary suite offers a brand-new king bed, while the kid’s room includes bunk beds for family fun. Accommodating up to 9 guests, the property is just a short stroll to pristine Whitney Beach and nearby fishing docks, with top local restaurants and cafes — like Mar Vista, Shore, Whitney’s, and more — only minutes away. A local owner ensures attentive service to make your stay unforgettable. $10,000 off season/$14,000 season. Leased July 2025, August 2025, March 2026, April 2026
#A4660175

LONGBOAT KEY

6979 LONGBOAT DRIVE S

3 Beds

2 Baths

1,454 Sq.Ft.

$10,000

MLS#: A4660175

Step into living history in the heart of Historic Longbeach Village. This exceptional property occupies land that was part of Civil War veteran Thomas Mann’s 144-acre homestead, where in 1891 he built the island’s first permanent residence just steps away. This serene corner lot is where Longboat Key truly began! Fully rebuilt and elevated in 2025 to the highest modern standards after the 2024 storms, this turnkey coastal residence offers unmatched peace of mind and contemporary luxury. The light-filled, open-concept interior features vaulted ceilings, a gourmet kitchen with new stainless-steel appliances and quartz countertops, and two beautifully appointed spa bathrooms with premium fixtures and rainfall showers. The primary suite indulges with a king bed, wet bar, mini-fridge, and a windowed en-suite bath, while the second bedroom provides a comfortable queen bed. A dedicated home office is your third bedroom, with its full-size Murphy bed/desk. The private tropical backyard serves as a tranquil oasis, complete with a serene lily-pad pond, fire pit, and mature landscaping. Delivered fully furnished with beautiful coastal décor and equipped with high-speed fiber internet, the home is ideal for immediate personal enjoyment, remote work, or proven vacation-rental income. Grandfathered Village zoning permits short-term rentals. Enjoy an unparalleled lifestyle just a short walk from Whitney Beach, historic fishing docks, bay kayak launches, and waterfront dining. Longboat Key Club, St. Armands Circle, and downtown Sarasota’s world-class amenities are only minutes away. Rarely available: authentic historic significance, a total top-to-bottom 2025 rebuild, and the quintessential Village address. Move-in ready
#A4673491

LONGBOAT KEY

640 BROADWAY STREET

3 Beds

2 Baths

1,500 Sq.Ft.

$9,800

MLS#: A4673491

THIS WONDERFUL PROPERTY IS FOR RENT...NOT FOR SALE...short stories inc...be careful of 3rd party web sites. Stunning direct Gulf front 3 bedroom condo on the quaint island of Longboat Key on Florida's tranquil Gulf Coast. Sunny days and uncompromising beauty awaits you. Experience the island lifestyle of relaxation and escape. Warm ocean breezes flow through the unit and the peaceful sound of the ocean is calming and soothing. Pristine turquoise water and beautiful beach. Take a refreshing dip in the pool. Enjoy magnificent color filled sunsets every evening. Take a leisurely stroll on the beach. Sun filled rooms, amazing views. Dine alfresco on the balcony and enjoy breathtaking views of the Gulf of Mexico. Located close to stylish downtown Sarasota and St. Armand Circle you will enjoy a vast array of culture, entertainment and distinctive boutique shopping. It is a remarkable destination for your getaway paradise vacation.
#A4537061

LONGBOAT KEY

4325 GULF OF MEXICO DRIVE 507

3 Beds

2 Baths

1,336 Sq.Ft.

$9,587

MLS#: A4537061

Delightfully appealing seasonal/short term rental at Bayport Beach and Tennis Club on Longboat Key. This spacious 2/2 residence comes fully furnished and equipped with flat screen TV's, cable and WiFi. This residence features a spacious screened lanai with garden views in addition to an outdoor sun deck with loungers for basking in the sun. Bayport sits on 27 lushly landscaped acres and has 1200 feet of pristine private beach for your exclusive use. Complimentary beach chairs and umbrellas are provided for guests. Enjoy an active lifestyle at Bayport as the Community includes a junior sized heated Olympic swimming pool, 4 har-tru tennis courts for the Tennis enthusiasts, a fitness center, fishing pier, kayak storage, nature trails and a clubhouse perfect for gathering. Just minutes to St. Armand's Circle which is well known for its world class shopping and dining. Cross over the Ringling Bridge to Downtown Sarasota where you will find additional dining, theater, opera, ballet, symphony, art galleries, the Van Wezel Performing Arts Hall, Selby Gardens and of course the Ringling Museum. NOW AVAILABLE: September - December 2023. Please contact Agent for availability.
#T3415401

LONGBOAT KEY

744 BAYPORT WAY 744

2 Beds

2 Baths

1,456 Sq.Ft.

$9,500

MLS#: T3415401

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