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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

414

# of Listings

2

Avg # of Bedrooms

$789

Avg. $ / Sq.Ft.

$1,324,240

Med. List Price

Browse Long Boat Key Real Estate Listings

All listings

$250,000 - $500,000

414 Properties Found. Page 16 of 28.

Here’s your chance to own a little slice of paradise on Longboat Key! This updated 2-bedroom, 2-bath condo is tucked into the sought-after Seaplace community—right on the sugar-white sands of the Gulf. Bright, open, and beachy, this coastal retreat has everything you need: an open layout, a spacious kitchen with stainless steel appliances, a comfy primary suite with a walk-in closet and en-suite bath, plus a private guest suite with its own bath. New LVP flooring in the main living areas and plush carpet in the bedrooms.

Step out to your screened lanai and soak in the tropical views of lush landscaping and the tennis courts—or take a few steps and you're on the beach! End your days with breathtaking sunsets and your toes in the sand.

Seaplace offers 42 acres of beautifully landscaped grounds, a half-mile of private beach, two heated pools and spas, and even a playground. The updated clubhouse has a gym, sauna, library, large kitchen, and a Gulf-front patio with grills. You’ll also love the Har-Tru tennis courts, walking trail, 24-hour gated entry, and on-site maintenance.

Plus, you're just minutes from local shops, Publix, and the amazing restaurants and boutiques at St. Armands Circle. Don’t miss your chance to live the laid-back coastal life—schedule your private tour today!

LONGBOAT KEY

1975 GULF OF MEXICO DRIVE G4-308

2 Beds

2 Baths

1,178 Sq.Ft.

$600,000

MLS#: TB8404915

THIS IS THE LARGEST 2 BEDROOM 2 BATH FLOOR PLAN IN SEAPLACE! Located on the second floor of the G3 building, this home is move in ready! The previous den has been enclosed for a proper bedroom and updated! The primary bedroom and bathroom have both been updated. Updated lighting, updated baseboards, no carpet, new hurricane rated sliders and windows! Plantation shutters are added for easy care and the coastal vibe! This building is located directly adjacent to the Har-Tru tennis courts, perfect for the avid player! Seaplace is a Gulf front community situated on lushly maintained grounds and offers not only tennis courts, a secure guarded gated entry, clubhouse, two heated pools/spas, fitness, Gulfside BBQ, organized social functions, onsite management and the icing on the cake is direct beach access! Residence comes completely furnished, assigned parking space #115, and assigned storage space. Perfect for your second home and income protection, with a 2-month minimum rental period. Seaplace is located on beautiful Longboat Key convenient to grocery shopping, banking, and the best shopping on St. Armand's Circle! Or make a reservation at any number of first-class restaurants on the Key, and dine waterside, or find a nice cozy quiet booth inside and take in one of nature's most beautiful gifts of a sunset, and if you are lucky, you just may see the dolphins diving and playing! Come off the beach at the south end and you are immediately in downtown Sarasota, where you can catch any number of plays, or a live band for evening entertainment. The weekend offers a sidewalk Farmer's Market, with an assortment of vendors! Whatever time you have planned to be here, may just not be enough!!!

LONGBOAT KEY

2039 GULF OF MEXICO DRIVE G3-207

2 Beds

2 Baths

1,369 Sq.Ft.

$599,000

MLS#: A4657767

Make your dreams come true with this beautiful waterfront condominium located at the popular Longboat Harbour resort! Enjoy gorgeous views of the water the moment you step in. This newly renovated 2BD/2BA second floor unit offers a roomy open floor plan with plenty of natural light, is being sold turnkey furnished. New Luxury Vinyl flooring and hurricane windows has been installed throughout. The updated kitchen has Granite countertops and new appliances. Benefit from your own private washer and dryer located in the guest bathroom. The inclusive patio with new sliders oversees the canal as well as a partial view of the gulf. One assigned covered parking space is included. Sorry, no pets are allowed. Conveniently located on mid Longboat Key between the quaint towns of Anna Maria Island and Lido. Saint Armand's Circle and Downtown Sarasota is only minutes away with fine dining, specialized shopping, art galleries, Sarasota Orchestra, Van Wezel theater and more... Great investment property, second home or weekend getaway. Longboat Harbour resort is a gated community with on site management. Amenities include: four heated swimming pools, tennis courts, sauna room, art studio room, bike storage, BBQ grills, clubhouse, billiard room, woodshop facility, fitness center, pickleball courts, putting green, shuffleboard, kayaking storage, boat docks and a fishing station. Deeded beach access is located across the Street with a pavilion which has restrooms, showers, chair storage, car/boat washing.

LONGBOAT KEY

4380 EXETER DRIVE 204

2 Beds

2 Baths

1,152 Sq.Ft.

$579,000

MLS#: A4656600

Spellbinding Sunrises, Sunsets, and magical water views from this nicely updated Bayfront Beauty in an ideal Mid-Key Bay to Beach setting can be yours now. Delight in the panoramic Bay to Gulf views from the moment you wake up until you turn in after a fun-filled day at the private beach, or after taking your boat, kayaks or paddleboards out to explore paradise. The spacious patio is the perfect spot to relax and take in the gorgeous water and nature views. The updated kitchen and 2nd bedroom offer great views of the Gulf and the primary bedroom and living/dining offer glorious direct Bay views. A private under building storage unit, and an assigned under building parking space allows plenty of room for all your toys and keeps your car tucked away. Buttonwood Cove is a charming community with only 56 residences and offers countless amenities including 5 acres of beautifully manicured grounds, a sparkling bayside heated pool, renovated clubhouse with a full kitchen, tennis/pickleball courts, a fishing dock, and a kayak launch/dock. The deeded access to the expansive private beach includes a shelter with picnic tables, a grill and beach chairs and of course gentle balmy breezes & breathtaking sunsets. Recent community improvements include new roofs & elevators, driveways, drainpipe replacement, Trex composite docks and exterior paint. When you’re ready to explore, St. Armand’s Circle with stylish boutiques, restaurants, and plentiful cultural attractions of Sarasota are only a short drive away. Make your island dreams come true today!

LONGBOAT KEY

3540 GULF OF MEXICO DRIVE 202

2 Beds

2 Baths

1,479 Sq.Ft.

$575,000

MLS#: A4648922

It's all about the spectacular FULL BAY VIEWS in this tranquil and beautifully renovated island retreat located in the beach to bay community of Sutton Place. This 2 bedroom, 2 bath residence is a true coastal oasis all done up in seaside hues. The gorgeous, remodeled kitchen is open to the living/dining area across an expanse of granite that includes a custom made dining table with lots of storage underneath and seating all around! Porcelain tile flooring makes the journey from one room to another a seamless and beautiful transition. These smart owners have converted the lanai into finished square footage and it is the perfect spot to enjoy a morning coffee or an evening beverage while watching the fish jump or the birds fly by. They also upgraded to IMPACT RESISTANT SLIDING DOORS AND WINDOWS throughout. The Primary bedroom has this same gorgeous view and a renovated ensuite bath. The once walk-in closet was converted to a small office space, (which could easily be changed back) but it’s current use is rather genius. When guests are not in town, the 2nd bedroom is another tranquil space to enjoy. Did I mention this is a 2 pets friendly community?! Sutton Place also offers its own PRIVATE BEACH CLUB and includes an abundance of amenities including 2 pools, a clubhouse, and an onsite marina with slips for a nominal fee of only $300 per year. The community recently completed a number of updates including repainting, reroofing and passing the milestone inspection and securing a 10 year certification. This owner has paid for all of those upgrades in full. The unit is being offered furnished with exceptions. Here you will find a remarkable quality of laid-back island life but if you're ready for more, enjoy the multitude of restaurants, shopping and the cultural mecca of downtown Sarasota, all within a short drive away.

LONGBOAT KEY

600 SUTTON PLACE 104B

2 Beds

2 Baths

1,144 Sq.Ft.

$575,000

MLS#: A4644920

Bathed in natural light, this 2BR, 2.5BA townhome in Fairway Bay at Bay Isles offers an inviting blend of warmth, character, and coastal sophistication. Inside, soaring ceilings and neutral finishes highlight the home’s open design and timeless appeal. The galley kitchen, complete with a charming breakfast nook framed by plantation-shuttered windows, is the perfect place to enjoy morning sunshine. Skylights crown the adjacent dining area, infusing it with light and drama, while the spacious living room - with its fireplace and sliders to the enclosed patio - creates a natural gathering space. From here, a private walk-down provides direct access to Fairway Bay’s resort-style amenities. A guest half-bath adds convenience on the main level. Upstairs, a dramatic catwalk overlooking the dining space and skylights leads to two en-suite bedrooms. Each offers cathedral ceilings, while the primary suite impresses with dual vanities and a spa-like bath featuring a soaking tub beneath an arched skylight. This residence also includes a 2-car garage with a large bonus room—an ideal setting for a workshop, studio, or extra storage. As a resident of Fairway Bay, you will enjoy Deeded Beach Access at the Bay Isles Beach Club, 24-hour gated security, a heated pool, tennis & pickleball courts, fitness center, and all the privileges of Bay Isles living. Optional membership at the Longboat Key Golf & Tennis Country Club and deepwater slips are also available, elevating the lifestyle even further.

LONGBOAT KEY

1904 HARBOURSIDE DRIVE 202

2 Beds

2 Baths

2,606 Sq.Ft.

$549,000

MLS#: A4662403

WOW! Full, unobstructed and private views of the Intracoastal Waterway, Sarasota Bay and the dramatic city skyline and Ringling Bridge from the protected balcony + 1 under-building deeded parking spot. This immaculately maintained, never-rented condominium is a blank canvas, ready for your personal touches, however, recently both bedroom closets were professionally redone, it was freshly painted and new luxury vinyl floors installed. The living space is filled with natural light, showcasing the stunning bay/city views. The primary suite offers direct water views, while the second bedroom provides a comfortable retreat for guests. The mid-rise buildings feature their pool, while the larger Fairway Bay community offers a vibrant lifestyle with access to The Bay Isles Beach Club, scenic walking trails, heated pools, a fitness center, tennis and pickleball courts, a clubhouse, and kayak launches. For even more amenities, an optional Longboat Key Club membership provides access to championship golf, Har-Tru tennis courts, a spa, fine dining and a 291-slip deep-water marina. It’s 1.3 miles to Publix, CVS. four miles to St. Armands Circle. Six miles to downtown Sarasota and 10 miles to SRQ Airport. A rare opportunity to own a prime bayfront condominium with deeded and private beach access and knockout views in one of Longboat Key’s desirable communities.

LONGBOAT KEY

1930 HARBOURSIDE DRIVE 142

2 Beds

2 Baths

1,312 Sq.Ft.

$549,000

MLS#: A4645253

#A4639404

LONGBOAT KEY

4400 EXETER DRIVE J-201

2 Beds

2 Baths

1,376 Sq.Ft.

$525,000

MLS#: A4639404

LOCATION! LOCATION! LOCATION! Looking for a Beach/Bay Getaway Villa? This cozy End Unit Beach/Bay 2-bedroom/2-bath Sunny Villa boasts 1084 square feet of Longboat Key Florida Fun! Single story living with a convenient covered carport only a few steps away from your front door. Villa 15 is located directly across the street from the tranquil Gulf with its crystal-clear turquoise blue waters and uncrowded soft sandy beaches that attract visitors from all over the world. (Take joy with 3 beach access points, one private deeded) Enjoy walks along the shore, kayaking on the bay or read a book, unwind and soak up the sun on your own private patio while taking in the beauty of this incredible location. The patio is an ideal spot for morning coffee, watching a game of shuffleboard, hosting friends for sunset libations, evening grilling, or simply relaxing in solitude. Your beach/bay lifestyle possibilities are endless. Worry free living with recent Hurricane Impact Windows/Sliding Doors, Roof, & Carport (2020). As an added bonus with the sale of this Villa, the longtime owner since 1976, former Canadian Navy-Man, and a wonderful Nonagenarian, will be leaving most of his nautical treasures gathered from lands around the world for you to enjoy. Set like a jewel on the barrier island of Longboat Key, the community of Windward Bay is a magical wildlife haven nestled mid-island, flourishing on 26 acres and graced with 1/2 a mile of waterfront trails to relish. A low-density residence and a nature lover’s delight to gaze both frolicking dolphins and manatees as they play. Bird enthusiasts jubilate with their front-row seat of the magnificent Florida birds that call Windward Bay their home. Witness the vibrant plumage and graceful flights of these majestic creatures as they effortlessly navigate the glorious skies above. Windward Bay offers numerous amenities that make it an exceptional value including: 2 tennis/pickleball courts, 2 marinas with 28 boat & jet ski slips for a low monthly fee, barbecue grills throughout, fishing piers, 2 fish cleaning stations, kayak racks, 2 heated pools, shuffleboard, bike racks, a clubhouse with kitchen, library, fitness room, meeting room, 2 saunas, and community fire pits throughout the property. Conveniently accessible to Downtown Sarasota, St. Armands Circle, Anna Maria Island, Historic Cortez Fishing Village, Championship Golf Courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. Welcome home to “Pet Friendly” Windward Bay, where TWO pets are allowed. Windward Bay is a financially healthy Condo Association with a proactive Board. The Milestone Inspection and Capital Reserve Study are complete and Monthly Condo Fees for 2025 were actually reduced. This wonderful villa exemplifies “Florida Gulf to Bay Living” at its finest. Perfect for couples or individuals seeking paradise! Schedule your private tour today and make these experiences a reality.

LONGBOAT KEY

4840 GULF OF MEXICO DRIVE Villa 15

2 Beds

2 Baths

1,084 Sq.Ft.

$524,900

MLS#: A4652683

NEW PRICE:This is a great opportunity to own a piece of paradise on beautiful Longboat Key in the community of Seaplace which is located on 42 acres of land right on the azure waters of the Gulf of Mexico. This beautifully updated 2bedroom/1bath condominium is coming furnished for your convenience. Newly installed hurricane impact slider in the living room and impact window in the primary bedroom and all kitchen appliances are stainless steel. This residence would make a wonderful vacation getaway or investment. Seaplace has many amenities which include two swimming pools with spas, kiddie pool, three Har-Tru tennis courts, a lovely remodeled clubhouse with sauna and fitness room all looking over the magnificent Gulf. Locally only a short distance to Saint Armand's Circle and downtown Sarasota where you will enjoy a fabulous variety of restaurants, shopping, Art Galleries, theaters, Ballet, Sarasota Orchestra and the Opera.

LONGBOAT KEY

2055 GULF OF MEXICO DRIVE G2-108

2 Beds

1 Baths

1,033 Sq.Ft.

$519,000

MLS#: A4654096

#TB8378560

LONGBOAT KEY

1935 GULF OF MEXICO DRIVE G7-304

2 Beds

1 Baths

1,129 Sq.Ft.

$510,000

MLS#: TB8378560

#A4631785

LONGBOAT KEY

2045 GULF OF MEXICO DRIVE M1-502

2 Beds

1 Baths

1,019 Sq.Ft.

$509,000

MLS#: A4631785

This well-appointed, fully furnished, two-bedroom, two-bath Portobello residence is so close with deeded access to Longboat Key's 10-mile beach. This impeccably maintained convenient ground-level home is in pristine condition, and a spaciously designed, coastal-inspired interior creates feelings of tranquility and hospitality. The primary living space enjoys abundant natural light from sliding glass doors opening onto a screened and covered lanai for your relaxation and added dining alfresco. The kitchen has all appliances and granite countertops with passageway to the dining area. The primary bedroom has sliding glass doors to the lanai with en-suite bath and generous walk-in closet, and a guest wing offers every comfort with its sliding glass door to the lanai too. Portobello gives support and comfort to owners with a full-time on-site maintenance crew. You and your family and friends will love the outdoor activities that are near such as LBK Town Center, the beach, miles of pedestrian walkways and more miles of designated bikeways, golf, fishing, Bayfront Park with pickleball, treed dog park and amenities for all ages, staffed USTA award-winning public 10 Har-Tru clay tennis courts and the renowned one-of-a-kind mecca for shopping and dining at St. Armands Circle. L-I-V-I-N the dream on Longboat Key. News Flash! Starbucks to open on LBK late Summer 2025 at midkey 3174 Gulf of Mexico Drive. We are walking distance away, and a $100 gift certificate will be given to Buyer.

LONGBOAT KEY

3240 GULF OF MEXICO DRIVE B104

2 Beds

2 Baths

1,432 Sq.Ft.

$499,900

MLS#: A4637105

Gulf Views | Move-In Ready | Gated Community
Welcome to Seaplace, one of Longboat Key’s most desirable Gulf-front communities! This charming 2-bedroom, 1-bath residence is located on the 3rd floor of Building G5 (Unit 304) and offers sweeping southwest-facing views of the Gulf of Mexico from your private, screened-in lanai.
Enjoy morning coffee or evening sunsets while soaking in the turquoise waters just beyond your doorstep. Inside, the open-concept layout connects the living and dining areas with a bright, functional kitchen—perfect for relaxing or entertaining.
Whether you’re searching for a vacation getaway, income-producing investment, or full-time coastal retreat, this condo checks every box.
Seaplace is more than a community—it’s a resort-style experience, offering:
• Gated entry with 24-hour guard service
• Two sparkling swimming pools and two hot tubs
• A shallow kiddie pool for the little ones
• Three tennis courts
• A beautifully updated clubhouse for social gatherings
• Walking trails through lush tropical grounds
• Beach chairs & umbrellas provided for residents
Best of all—you’re just steps away from the sand. With unbeatable Gulf views, modern comforts, and a strong community feel, this property offers the best of Longboat Key living.
Don’t just dream about the beach—live it. Schedule your private showing today and discover why Seaplace is one of Longboat Key’s most beloved communities.

LONGBOAT KEY

1965 GULF OF MEXICO DRIVE G5-304

2 Beds

1 Baths

1,023 Sq.Ft.

$499,900

MLS#: A4660599

Nestled in the highly sought-after Seaplace community on the pristine shores of Longboat Key, this bright and inviting two-bedroom, two-bath residence offers the perfect coastal retreat.

Step inside to find a spacious living and dining area with abundant natural light, comfortable furnishings, and a seamless flow to the screened lanai—where you can relax and enjoy the fresh sea breezes while overlooking the lush tropical landscaping. The kitchen opens easily to the dining space, making entertaining a breeze.

The primary suite features a walk-in closet and private en-suite bath, while the guest suite offers its own full bath—ideal for hosting family and friends. Offered turnkey furnished, this home is ready for you to move right in—just bring your swimsuit and flip-flops.

Life at Seaplace is all about resort-style living. This 42-acre, Gulf-front community boasts:

A half-mile of private beachfront along the turquoise waters of the Gulf of Mexico

Two heated pools & spas, plus a kid’s pool and playground

A remodeled clubhouse with fitness center, sauna, library, and catering kitchen

Three Har-Tru tennis courts and a one-mile walking trail

24-hour guarded entry and on-site management for peace of mind

In the evenings, take a short stroll to the beach to watch breathtaking Gulf sunsets, or head just minutes away to Publix, St. Armands Circle, and downtown Sarasota’s vibrant dining and cultural scene.

This Seaplace condo offers the ideal combination of comfort, convenience, and coastal charm—schedule your private showing today and start living the Longboat Key lifestyle you’ve always imagined.

LONGBOAT KEY

1975 GULF OF MEXICO DRIVE G4-206

2 Beds

2 Baths

1,178 Sq.Ft.

$499,000

MLS#: A4663933

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