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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

$858

Avg. $ / Sq.Ft.

$1,508,088

Med. List Price

Browse Long Boat Key Real Estate Listings

$250,000 - $500,000

54 Properties Found. Page 1 of 4.

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

1,260 Sq.Ft.

$499,900

MLS#: A4637105

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.

$499,000

MLS#: A4652683

#A4674675

LONGBOAT KEY

6700 GULF OF MEXICO DRIVE 139

2 Beds

2 Baths

1,305 Sq.Ft.

$499,000

MLS#: A4674675

Embrace an extraordinary coastal lifestyle where fun water adventures fill your days and peaceful evening walks along the shore mark every sunset. Step outside your back door and onto the sand—the beach is quite literally your backyard! This Seaplace residence offers a rare opportunity to live just steps from the beach, right on the sparkling waters of the Gulf of Mexico.

Located on the ground floor, this 2-bedroom, 2-bath condominium offers the rare convenience of private patio access, so you can come and go without passing through the main entrance of the building.

Enjoy the best of Sarasota every day in a simple yet thoughtful layout designed for connection. The open-concept floor plan seamlessly links the kitchen, dining, and living areas to a screened lanai with southern exposure, filling the space with natural light and views of lush tropical landscaping. Both bedrooms are generously sized, with the primary suite featuring an en-suite bath.

During recent hurricane events, the property remained completely safe and dry—providing valuable peace of mind for its owners.

You’re only a few steps from Seaplace’s pristine sandy beaches and one of two heated swimming pools. Community amenities include a clubhouse with a Gulf-front patio, several grilling areas, library, fitness room, sauna, kiddie pool, playground, and three Har-Tru tennis courts.

The quarterly association fee of $4,200 covers exterior maintenance, building insurance, water, sewer, cable, and access to all community amenities. Rentals are permitted with a two-month minimum, offering flexibility for seasonal ownership or investment potential. The association has announced a $500 reduction per quarter for the upcoming season so now's an even better time to move in!

Ideally located just minutes from St. Armands Circle and downtown Sarasota, you’ll enjoy world-class dining, boutique shopping, theatre, ballet, opera, and art galleries... all within easy reach.

This Seaplace home isn’t just beautiful. It’s a rare opportunity for those seeking comfort, security, and lasting value by the Gulf.

LONGBOAT KEY

1965 GULF OF MEXICO DRIVE G5-104

2 Beds

2 Baths

933 Sq.Ft.

$495,000

MLS#: A4670323

#A4674741

LONGBOAT KEY

4370 CHATHAM DRIVE 204

2 Beds

2 Baths

928 Sq.Ft.

$495,000

MLS#: A4674741

#A4666657

LONGBOAT KEY

4440 EXETER DRIVE 204

2 Beds

2 Baths

1,152 Sq.Ft.

$485,000

MLS#: A4666657

PRICE ADJUSTMENT: 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 America. This beautifully updated 2bedroom/1bath condominium with separate dressing area and sink. It's coming furnished for your convenience with stainless steel appliances in the kitchen. Newly installed hurricane impact slider in the living room and impact window in the primary bedroom, plus newly installed hurricane front door and side window. 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. 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

933 Sq.Ft.

$485,000

MLS#: A4654096

0.5 mi to Gulf beach access • Two heated pools & tennis courts • Gated Gulf-front community

Welcome to Seaplace, a premier Gulf-front condominium community along Longboat Key’s scenic Gulf of Mexico Drive. This two-bedroom, two-bath residence (Unit G4-308) combines coastal living and community amenities in one of Sarasota County’s most desirable barrier-island locations. The open-concept layout flows seamlessly from the kitchen through the main living area to a screened lanai overlooking lush tropical landscaping and the Har-Tru tennis courts. Durable LVP flooring enhances the main living spaces, while neutral finishes allow a bright, airy feel throughout. The kitchen features stainless-steel appliances, ample cabinetry, and generous counter space for meal prep. The primary suite includes a walk-in closet and private bath; the secondary bedroom and full guest bath offer ideal separation for visiting friends and family. Convenient in-unit washer and dryer add everyday functionality.

Residents of Seaplace enjoy approximately ½ mile of Gulf beachfront, two heated swimming pools and spas, a Gulf-side sundeck, Har-Tru tennis courts, walking paths throughout 42 acres of manicured grounds, a well-equipped fitness center, clubhouse with full kitchen and library, sauna, children’s playground, barbecue grills, and 24-hour staffed security gate. The quarterly association fee of $4,315 covers exterior maintenance, building insurance, water, sewer, cable, and amenities. Service animals are permitted per association rules; no pets otherwise. Seasonal and annual rentals are allowed with a two-month minimum.

Situated along the island’s southern corridor, Seaplace offers proximity to both natural beauty and daily convenience. Publix (0.8 mi) and Bayfront Park Recreation Center (1.6 mi) provide easy access to groceries, pickleball courts, and a kayak launch. Fine dining options such as Harry’s Continental Kitchens (1.3 mi) and Euphemia Haye (1.1 mi) are nearby, along with The Shore Restaurant (1.9 mi) and the boutiques of St. Armands Circle (3.8 mi). Longboat Key Club Golf & Tennis (2.7 mi) and Downtown Sarasota (6.5 mi) offer world-class recreation and cultural attractions including the Van Wezel Performing Arts Hall, Ringling Museum, and Marie Selby Botanical Gardens.

Seaplace’s Gulf-front setting provides direct beach access for sunrise or sunset walks, while community walking trails and tropical courtyards create a resort-style atmosphere year-round. This move-in-ready residence represents an exceptional opportunity to enjoy coastal living on Longboat Key, combining location, amenities, and Gulf access within a secure, well-maintained community.

Includes interior laundry, screened lanai, and access to multiple pools, tennis, clubhouse, and beachfront amenities. Floor plan are available within the listing for additional detail.

LONGBOAT KEY

1975 GULF OF MEXICO DRIVE G4-308

2 Beds

2 Baths

1,068 Sq.Ft.

$480,000

MLS#: A4666939

Turnkey two-bedroom, two-bath residence in a first-floor, walkout location. Freshly painted with updated baths and 1,172 square feet of living space. Enjoy direct access to the harbor-front walking path and deeded beach access with baths, outdoor shower and chair storage. Includes a covered, assigned parking space. Resort-style amenities include a renovated clubhouse with kitchen and presentation space, fitness center, sauna, pickleball and tennis courts, outdoor grilling and entertainment area, kayak and paddleboard launch with storage, billiards, poker room, woodworking shop, library and bike storage. This self-managed community has strong reserves, no special assessments and no water intrusion from the 2024 storm season. Ideally located near Bayfront Park and just minutes from Publix, Longboat Key Town Center and St. Armands Circle.

LONGBOAT KEY

4370 CHATHAM DRIVE 104

2 Beds

2 Baths

1,072 Sq.Ft.

$480,000

MLS#: A4674307

Gated Gulf-front community • Two heated pools & tennis courts • Beach access within minutes

Experience coastal living at Seaplace, a gated Gulf-front community on the southern end of Longboat Key. This two-bedroom, two-bath residence (Unit G4-206) features an open-concept layout and a screened lanai overlooking lush tropical landscaping and community green space. Recent improvements include hurricane-rated impact windows and lanai enclosure, providing peace of mind and energy efficiency while enhancing natural light and sound protection. Inside, durable flooring and a neutral color palette create a bright, relaxed atmosphere. The kitchen offers stainless-steel appliances, ample cabinetry, and a breakfast bar that opens to the main living area. The primary suite includes a walk-in closet and private bath, while the guest bedroom and full hall bath provide comfortable separation for visitors. A full-size washer and dryer inside the unit adds convenience and functionality.

Residents of Seaplace enjoy approximately ½ mile of Gulf beach frontage and an array of resort-style amenities across 42 acres of manicured grounds. Highlights include two heated swimming pools and spas, Har-Tru tennis courts, walking paths, a clubhouse with fitness center, sauna, and library, a playground, and community grilling areas. The on-site management and 24-hour staffed gatehouse provide security and peace of mind in this established coastal community.

The quarterly association fee of $4,315 covers exterior maintenance, building insurance, water, sewer, cable, and amenities. Service animals permitted per association rules; no pets otherwise. Seasonal and annual rentals are allowed with a two-month minimum.

Seaplace’s location combines tranquility with access to shopping, dining, and cultural attractions. Publix (0.8 mi) and Bayfront Park (1.6 mi) are nearby for groceries, recreation, and pickleball. Enjoy dining at Harry’s Continental Kitchens (1.3 mi), Euphemia Haye (1.1 mi), or The Shore Restaurant (1.9 mi), and explore boutique shopping at St. Armands Circle (3.8 mi). Longboat Key Club Golf & Tennis (2.7 mi) and Downtown Sarasota (6.5 mi) offer golf, marinas, and cultural venues including the Ringling Museum and Selby Gardens.

Seaplace residents enjoy direct beach access for sunset walks along the Gulf, tropical courtyards, and a private coastal setting minutes from everything. Whether a seasonal retreat or year-round home, Unit G4-206 blends location, comfort, and quality within a secure, Gulf-front environment on Longboat Key.

Includes hurricane-rated windows and lanai enclosure, in-unit laundry, screened lanai, and access to pools, tennis, clubhouse, and Gulf-front amenities. A 3D virtual tour and floor plan viewer are available within the listing for additional detail.

LONGBOAT KEY

1975 GULF OF MEXICO DRIVE G4-206

2 Beds

2 Baths

1,068 Sq.Ft.

$479,000

MLS#: A4663933

Offers 1% lender credit at closing. Seller is offering $10,000 toward closing costs or prepaids, plus a $1,000 bonus to the buyer’s agent with a full-price offer—an exceptional opportunity you don’t want to miss!

Discover coastal living at its finest in this beautifully furnished 2-bedroom, 2-bath condo featuring a recently remodeled kitchen, new carpet, and modern electric shades. This bright and welcoming unit offers comfort and convenience just seconds from your own deeded beach access—perfect for daily walks or sunset strolls.

Enjoy a resort-style lifestyle with incredible amenities including 4 swimming pools, tennis and pickleball courts, a clubhouse, fitness center, library, art studios, billiards, shuffleboard, kayak launch, and a woodshop. The community harbor offers boat slips for rent at just $350–$425 per year—an unbeatable value!

No hurricane water intrusion, and all current assessments have been paid. Some online platforms may display inflated tax estimates—actual taxes will depend on exemptions and ownership details. A rare opportunity for turnkey coastal living in a vibrant, amenity-rich community!

LONGBOAT KEY

4350 CHATHAM DRIVE E106

2 Beds

2 Baths

1,072 Sq.Ft.

$469,000

MLS#: A4657888

72 ft x 26 ft Boat Slip on L-dock at Longboat Key Moorings Marina for sale. Exceptional views of Sarasota Bay and the city skyline from atop your flybridge. LBK Club membership is required. Direct access to Sarasota Bay and the ICW. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, Marina village that includes 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. All vessels must be approved prior to closing by the Association. Max length of vessel allowed is 67 LOA. Usable beam depends on vessel. Call to discuss the possibilities. A current photo of the vessel must be provided, and the vessel approved by the Association before entering the marina.

LONGBOAT KEY

2600 HARBOURSIDE DRIVE L-04

None Beds

None Baths

N/A

$450,000

MLS#: A4645494

Welcome to your cozy island townhome at the north end of Longboat Key. Perfect as a fulltime residence, seasonal retreat, or investment property, this one-bedroom, two-bath unit fits your needs. This two-story property weathered three hurricanes in 2024, sustaining only minor flooding in the garage during Hurricane Helene and a cracked top-floor window during Hurricane Milton. The HOA will cover and replace the window. On the ground floor, enjoy your private parking garage and storage space. The main living area on the first floor features an open-concept living room and kitchen, ideal for relaxing or entertaining. Step out onto the screened balcony to enjoy the natural beauty of Florida or unwind with your morning coffee. This floor also has a full bathroom and a pull-out sofa for
hosting guests.
The second floor boasts a spacious master bedroom with a king-sized bed and two walk-in closets, filled with natural light from large windows. This level includes a second bathroom and a sun deck with an outdoor shower, offering peaceful views of a natural reserve. It’s the perfect spot to soak up the sun or enjoy a good book in a hammock. Short-term rentals with a 14-day minimum stay are allowed, adding investment potential. From July 2024 - July 2025, the home already has booked rental income booked totaling $45,0000.
With some cosmetic upgrades, this could be even more! The unit is part of a top-notch tennis club that now includes two pickleball courts. You'll be close to the pool and the island’s beaches. Pet-friendly and welcoming, the community features a Junior Olympic-sized pool, a Tiki Bar, and a restaurant for a resort-like feel. Nature trails wind through the property, leading to a dock with stunning views of Sarasota Bay—
perfect for launching your kayak to explore mangrove tunnels or paddle alongside manatees and dolphins.
Whether you're into kayaking, tennis, pickleball, cycling, or jogging in nearby John Durante Community Park, this condo offers the perfect balance of luxury and leisure. Your island paradise is waiting—make it yours today!

LONGBOAT KEY

619 CEDARS COURT

1 Beds

2 Baths

1,244 Sq.Ft.

$450,000

MLS#: A4629084

Welcome to Neptune on Longboat Key — a charming community where coastal comfort meets relaxed island living. This bright 2-bedroom, 1-bath residence features tile flooring throughout, a full kitchen with quality appliances, and a beautifully tiled bath. The open living and dining area leads to a screened lanai surrounded by lush tropical landscaping — the perfect spot to enjoy morning coffee and Gulf breezes. Neptune is a boutique, 12-unit complex offering direct beach access and tropical grounds. Owners enjoy excellent rental flexibility with a 1-month minimum lease, up to 12 times per year. Ideally located near Publix, St. Armands Circle, and the dining and cultural attractions of Sarasota — perfect as a vacation retreat, income property, or year-round island getaway.

LONGBOAT KEY

2850 GULF OF MEXICO DRIVE 2

2 Beds

1 Baths

695 Sq.Ft.

$449,000

MLS#: A4670111

Imagine living with these breathtaking water views from the early morning magnificent sunrises to the afternoons with Manatees and Dolphins swimming by your own slice of paradise. Untouched by the recent storms, this one bedroom one bath unit is one the most affordable options on Longboat Key. Tastefully decorated and fully furnished with Luxury Vinyl Laminate floors, Impact Sliders and Windows, Granite Countertops, beautiful premium cabinets and newer appliances in the kitchen. All you need to bring is your clothes and toothbrush.
Located in the amenity rich Longboat Harbour Gated Condominium complex which offers private gated beach access including a pavilion with bathrooms, 4 heated swimming pools, grills, extra storage, shuffle board, putting green, tennis and pickle ball courts, a club house with a billiard and card room, dining hall, wood shop and even an art and craft room. Deep Water Marina to accommodate power or sailboats up to 34 feet, available on a first come first serve basis for under $400 per year. Great rental opportunity. Located mid key with easy access to St Armand’s and Sarasota. Truly a resort lifestyle with an affordable price.

LONGBOAT KEY

4310 FALMOUTH DRIVE 105

1 Beds

1 Baths

747 Sq.Ft.

$429,900

MLS#: A4652643

1 2 3 4

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