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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

507

# of Listings

2

Avg # of Bedrooms

$867

Avg. $ / Sq.Ft.

$1,539,132

Med. List Price

Browse Long Boat Key Real Estate Listings

All listings

$250,000 - $500,000

507 Properties Found. Page 21 of 34.

#A4671530

LONGBOAT KEY

4380 EXETER DRIVE H202

2 Beds

2 Baths

1,152 Sq.Ft.

$549,000

MLS#: A4671530

New on site 3 days ago

Secure your piece of paradise and a proven income stream with this fully furnished, turnkey 2-bedroom, 2-bath second-floor condominium featuring several select owner updates. Located on highly desirable Longboat Key, this property is an exceptional opportunity for investors seeking a profitable rental business or as a second home that generates income when not being enjoyed by the owners.
This bright, modern, and welcoming condo has been thoughtfully updated with premium
finishes and all the comforts, including a king-size bed in the primary bedroom. The
open-concept design is ready for immediate enjoyment or continued rental success.
Sold completely furnished and ready to generate income on day one. The current owner
can provide verifiable rental income data and expenses. Contact the listing agent for
detailed financial performance reports. Benefits from a 30-day minimum rental policy,
ideal for attracting premium seasonal renters. Bayport Beach & Tennis Club offers an
unbeatable amenity package that keeps guests returning: Stroll across the street to
your private, white-sand beach with stunning Gulf Coast views. Chairs and umbrellas
are provided. Enjoy the Junior Olympic-sized pool, well-maintained Har-Tru tennis
courts, a bocce ball court, kayak launching area, fitness room and community room with
library. A private pier on Sarasota Bay is perfect for fishing, watching dolphins and/or
manatees or enjoying breathtaking sunrise views. The condo features a semi-private
entrance, offering a peaceful and exclusive experience. Located mid-island, this is a
true hidden gem that perfectly blends relaxation and recreation. Don't miss this
opportunity to own a piece of luxury Gulf Coast real estate that pays for itself!

LONGBOAT KEY

618 BAYPORT WAY BAYPORT WAY 618

2 Beds

2 Baths

1,570 Sq.Ft.

$549,000

MLS#: A4673455

Experience the best of Longboat Key living at Sutton Place, ideally positioned mid-island with convenient access to both Sarasota Bay and the Gulf of Mexico. Enjoy deeded beach access just moments away—perfect for daily beach outings, sunset walks, and the pristine Gulf shoreline.
Active living comes naturally here. Bike to Bayfront Park for pickleball or tennis, or visit the nearby dog parks where neighbors and pets gather. When it’s time to relax, choose from two community pools, including one overlooking the marina and peaceful Bay waters. The community also offers multiple BBQ areas, creating ideal spaces for gatherings with friends and family in a beautifully maintained coastal setting.
This two-story townhome offers 2 bedrooms and a full bathroom upstairs, with a second bathroom conveniently located on the main level. The eat-in kitchen features a charming dining nook, and the adjoining screened porch provides a tranquil outdoor retreat. A private one-car garage adds convenience and storage for a vehicle, golf cart, or beach essentials.
Additional highlights include first-come, first-served dock slips available for a nominal fee and a setting that offers comfort and peace of mind. Seller reports the property had no flooding during Hurricane Helene.
Live the Longboat Key lifestyle—sun, sand, coastal breezes, and effortless island living.

LONGBOAT KEY

597 SUTTON PLACE

2 Beds

1 Baths

1,008 Sq.Ft.

$530,000

MLS#: A4669989

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.

$517,000

MLS#: A4662403

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

Price reduced

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

#A4631785

LONGBOAT KEY

2045 GULF OF MEXICO DRIVE M1-502

2 Beds

1 Baths

1,019 Sq.Ft.

$499,000

MLS#: A4631785

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

1,023 Sq.Ft.

$495,000

MLS#: A4670323

#TB8378560

LONGBOAT KEY

1935 GULF OF MEXICO DRIVE G7-304

2 Beds

1 Baths

1,129 Sq.Ft.

$495,000

MLS#: TB8378560

#A4666657

LONGBOAT KEY

4440 EXETER DRIVE 204

2 Beds

2 Baths

1,152 Sq.Ft.

$485,000

MLS#: A4666657

Price reduced

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

1,033 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

1,178 Sq.Ft.

$480,000

MLS#: A4666939

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

1,178 Sq.Ft.

$479,000

MLS#: A4663933

Discover the perfect blend of beachside escape and investment opportunity at this second-floor studio with direct Gulf views. Wake up to the sound of the waves and end each day with shimmering sunsets—this light-filled retreat places you just steps from the shoreline on beautiful Longboat Key. Inside, the open layout offers flexible living with an updated bath and a comfortable space ready to enjoy now, while leaving room for future updates to elevate value and style. With an on-site rental office and the rare ability to do short-term rentals, this condo is ideal for personal getaways, a consistent income stream, or both. Take advantage of the community pool, stroll the beach, or explore the island’s dining and boutique shops just moments away. Whether you’re seeking a turnkey coastal hideaway or an income-producing asset, this Gulf-front studio delivers endless potential in one of Longboat Key’s most desirable, easy-to-rent locations.

LONGBOAT KEY

3155 GULF OF MEXICO DRIVE 257

1 Beds

1 Baths

416 Sq.Ft.

$470,000

MLS#: A4672986

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

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