One of the most popular communities provided by {{page_data.agentName}}

Long Boat Key

One of the most popular communities provided by The Graf Group of Coldwell Banker

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 The Graf Group of Coldwell Banker

371

# of Listings

2

Avg # of Bedrooms

$1,220

Avg. $ / Sq.Ft.

$2,103,717

Med. List Price

Browse Long Boat Key Real Estate Listings

All listings

$250,000 - $500,000

371 Properties Found. Page 14 of 25.

Own your own slice of tropical paradise on Longboat Key with this beautiful two bedroom two and on half bath Villa in the exclusive Winding Oaks Community located behind the gates of Bay Isles Association. Sweeping views of the Longboat Key Club Harbourside Golf Course and a sparkling inland waterway from your primary bedroom and expansive living/dining room combo that both exit through sliders to a fully enclosed wrap around deck to further enhance your tropical lifestyle. Open floor plan with soaring ceilings and enclosed atrium help to maximize the natural light and make the 2,555 sq feet feel even larger.

Beautifully updated eat in kitchen with striking tray ceiling, ample pantry storage, bright white cabinets, quartz countertops and stainless steel appliances.

Primary owners suite includes an designer walk in closet, updated bath with ceramic tile, walk in shower, double sinks and quartz counter tops.
Split layout offers a private guest suite, with walk in closet, updated ensuite bathroom with ceramic tile, walk in shower and quartz counter tops. Large office with desk nook could easily be converted to another bedroom. Laundry room with storage and sink adjacent to large 2 car garage with epoxy floors and storage cabinets.

Meticulously maintained, Impact Windows and sliders throughout, low maintenance mature plantings in private enclosed front courtyard.

Dog friendly community. Beautiful updated community pool with bathrooms. Beach access via Bay Isles Beach Club which offers a private pavilion with bathrooms, volleyball, picnic tables, grills and ample parking. Low maintenance community where all exteriors and court yards are maintained by the association.

Conveniently located mid key, one mile from Publix and CVS and a short drive to the restaurants and shops of St Armand’s and Downtown Sarasota.

LONGBOAT KEY

3435 WINDING OAKS DRIVE 18

3 Beds

2 Baths

2,555 Sq.Ft.

$949,000

MLS#: A4680403

Welcome to this beautifully appointed ground floor residence that combines modern elegance with functional design. Newly remodeled in 2025, this residence features high-end finishes and modern amenities, making it an ideal retreat for those seeking luxury in a serene
environment.
Upon entering, you are greeted by a bright and spacious interior filled with natural light, thanks to strategically placed additional windows featured in corner/end units of this community. The subtle elegance of the interior is complemented by sleek flooring that enhances the flow from room to room. The kitchen is a true highlight, featuring quality cabinetry, elegant quartz counters, and modern stainless-steel appliances, which allow a harmonious flow, delivering both functionality and sophistication.

The open-concept layout continues through the dining and living areas, combining a blend of textures and stylish finishes to cohesively create an environment of relaxed elegance. An abundance of natural light floods this space through large retractable sliding glass doors, which provide the option of extending the outdoors in. A private outdoor patio showcases a beautiful backdrop of lush tropical landscaping, adding to the property’s overall appeal.

The bedrooms within the property are thoughtfully designed, each offering generous space and natural light. The primary suite offers a restful retreat, complete with an ensuite bathroom featuring modern fixtures and thoughtful design, ensuring comfort and privacy.

This property will continue to amaze, as beauty extends beyond its walls into an amenity-rich community of 27 acres of picturesque tropical landscaping. This gulf-to-bay community offers 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. A distinct advantage and unique selling point of this property is its proximity to a private, deeded beach. This property offers future owners not just exclusive beach access, but a revitalizing retreat amidst the hustle and bustle of life—truly a valuable benefit that amplifies the charm of this residence. Close to local amenities yet precisely
positioned to offer privacy and quietude, this property represents an excellent opportunity for discerning buyers. Experience the best of coastal living in this beautiful home, where modern comfort meets natural beauty. Welcome home!

LONGBOAT KEY

806 BAYPORT WAY 806

2 Beds

2 Baths

1,392 Sq.Ft.

$949,000

MLS#: TB8489326

Price reduced

Experience the coastal gulf front living lifestyle to its fullest, in this 3-bedroom 2 bath condo with views of the Gulf from inside as well as the 2 balconies. Make this your new oasis and enjoy the sunsets off one of your two separate balconies (one off the main living area and another private balcony for the primary bedroom). Start experiencing this 3-bedroom condo at Seaplace which is located on a pristine beach area of Longboat Key. There is an array of amenities across the 42 beautifully landscaped acres, including two heated swimming pools and spas, Har-Tru tennis courts, scenic walking trails, a fitness center and a new gulf front firepit area. The clubhouse offers a kitchen, library, fitness area and sauna. Additional features include playground, grilling areas, on-site management, and a 24-hour staffed gatehouse.

LONGBOAT KEY

1955 GULF OF MEXICO DR G6-311

3 Beds

2 Baths

1,492 Sq.Ft.

$949,000

MLS#: A4687954

Experience resort-style living at Tangerine Bay Club, a gated sanctuary on the desirable south end of Longboat Key. This impeccably maintained end-unit residence offers 2,400 square feet of refined living space with lush Sarasota Bay views and unmatched proximity to the area’s top attractions. Minutes to St. Armands Circle, downtown Sarasota, and steps to Dry Dock Marina and Restaurant. No current assessments and meticulously maintained grounds. Thoughtful floor plan with multiple terrace access points to enjoy morning and afternoon sun. This three-bedroom, two-and-a-half-bath, plus den, includes an oversized private two-car garage. There is also a natural gas barbecue on the front terrace. Resort-style amenities at Tangerine Bay Club include a heated pool, lap lane, heated spa, tennis, and regulation pickleball courts, a clubhouse with a fitness center, and a vibrant social room and calendar (happy hours, pickleball, cultural excursions). Freshly renovated boat dock, two kayak launches, a fishing pier, and prime fishing directly on Sarasota Bay. Enjoy just “sittin’ on the dock of the bay” watching the dolphins roll in. Take a scenic nature walk between Sarasota Bay and Quick Point Nature Preserve. Ownership includes (optional) membership to the Bay Isles Beach Club facilities for just $600.00 per year (application required).Longboat Key is renowned for golf, tennis, fine dining, boating, and world-class fishing. Be sure to explore the newly opened St. Regis resort, just a short stroll to the north on the beach side. Ongoing management ensures a carefree ownership experience with no special assessments anticipated. Recent capital projects (painting, waterproofing, elevator rebuilds, 2024 roof replacements, exterior tile walkway updates) have been completed and funded, with milestone inspections cleared. Pet-friendly, gated entry, and a day dock for fishing.
This residence offers the perfect blend of luxury, convenience, and peace of mind—an ideal retreat for those seeking sophistication and coastal living at its finest. DON’T JUST THINK ABOUT IT, COME EXPERIENCE IT FOR YOURSELF AND MAKE IT YOUR REALITY.

LONGBOAT KEY

350 GULF OF MEXICO DRIVE 211

2 Beds

2 Baths

2,394 Sq.Ft.

$938,500

MLS#: A4667037

Don’t miss this rare opportunity to call Sands Point home – an iconic beachfront community widely regarded as the crown jewel of Longboat Key. Nestled on the island’s coveted southernmost tip, this move-in-ready residence offers breathtaking sunsets and an unparalleled coastal lifestyle. Offered at an attractive value, this coastal escape presents a rare opportunity for the new owner to add their own finishing touches and create a truly personalized retreat. Welcome to your slice of paradise, where every day feels like a five-star coastal retreat, nestled inside the gates of the Longboat Key Club. Gracefully framed by towering palms, the curved waterfront drive creates a memorable sense of arrival, setting the tone for this one-of-a-kind mid-century modern residence where coastal elegance and timeless design converge. This spacious 1941 square feet, with its open floor plan feels more like a home than a condo. Step inside this bright third floor residence and discover a two bedroom, an office staged as a 3rd. bedroom and two baths, set in a split plan for privacy. Thoughtfully designed with warm custom cabinetry, elegant stone-inspired surfaces, and contemporary stainless appliances, this kitchen combines timeless craftsmanship with effortless coastal living. Floor to ceiling expanses of glass span the living area, offering a panoramic garden view and bathing the room in sunshine. The oversized layout provides endless possibilities for entertaining, gathering or simply enjoying the peaceful surroundings. Community amenities abound – enjoy the private beach with tiki’s, lounge chairs, pool, spa, library, community room w/ kitchen, marina access, bicycle storage, kayak launch, and additional owner’s storage space. Within walking distance to the well-renowned St Armands Circle for shopping and dining experiences. The pristine white sandy beach and gentle turquoise waters are calling your name. Schedule your private showing today and discover the lifestyle you deserve.

LONGBOAT KEY

100 SANDS POINT ROAD 303

3 Beds

2 Baths

1,941 Sq.Ft.

$915,000

MLS#: A4696825

Massive Price Reduction - Rare Opportunity to Own Your Slice of Beach Paradise! Live the ultimate coastal lifestyle with sun, sand, and breathtaking surroundings at an exceptional value. Stunning curb appeal duplex located in the highly desirable Longboat Key featuring two separate addresses, 578 Companion Way and 580 Companion Way. This bright and welcoming coastal retreat offers an elegant and comfortable living environment where refreshing sea air and natural sunlight fill the interior through expansive windows. The property features two separate units including one 2 bedroom 2 bathroom unit and one 2 bedroom 1 bathroom unit. Offered fully furnished and showcasing high quality updates throughout, the property includes a new roof, new AC systems, new water heaters, and all new appliances completed in 2025, delivering modern luxury and peace of mind. Residents may enjoy access to Cedars East resort style amenities including pool, fitness center, and tennis courts with a small optional membership fee. Ideally positioned just steps from the pristine, wide, and uncrowded Gulf beaches, this property provides the ultimate Longboat Key lifestyle. Conveniently located near world class dining and shopping at St Armands Circle, vibrant downtown Sarasota, championship golf courses, marinas, cultural attractions, and everything Sarasota has to offer. Vacation rentals are permitted, creating an outstanding opportunity for investors, seasonal residents, or families seeking to live in one unit while generating additional rental income from the second unit.

LONGBOAT KEY

578 COMPANION WAY

4 Beds

3 Baths

1,792 Sq.Ft.

$900,000

MLS#: A4682186

Massive Price Reduction - Rare Opportunity to Own Your Slice of Beach Paradise! Live the ultimate coastal lifestyle with sun, sand, and breathtaking surroundings at an exceptional value.. Stunning curb appeal duplex located in the highly desirable Longboat Key featuring two separate addresses, 578 Companion Way and 580 Companion Way. This bright and welcoming coastal retreat offers an elegant and comfortable living environment where refreshing sea air and natural sunlight fill the interior through expansive windows. The property features two separate units including one 2 bedroom 2 bathroom unit and one 2 bedroom 1 bathroom unit. Offered fully furnished and showcasing high quality updates throughout, the property includes a new roof, new AC systems, new water heaters, and all new appliances completed in 2025, delivering modern luxury and peace of mind. Residents may enjoy access to Cedars East resort style amenities including pool, fitness center, and tennis courts with a small optional membership fee. Ideally positioned just steps from the pristine, wide, and uncrowded Gulf beaches, this property provides the ultimate Longboat Key lifestyle. Conveniently located near world class dining and shopping at St Armands Circle, vibrant downtown Sarasota, championship golf courses, marinas, cultural attractions, and everything Sarasota has to offer. Vacation rentals are permitted, creating an outstanding opportunity for investors, seasonal residents, or families seeking to live in one unit while generating additional rental income from the second unit.

LONGBOAT KEY

578 - 580 COMPANION WAY

4 Beds

None Baths

1,792 Sq.Ft.

$900,000

MLS#: A4682264

Bayport Beach & Tennis Club is a true Longboat Key Gulf-to-Bay community, set across 27 acres of beautifully maintained gardens with 1,200 feet of pristine private Gulf beach. Designed by Tim Siebert, one of the founding architects of the renowned Sarasota School of Architecture. Bayport is celebrated for its award-winning, timeless design. Residences like this rarely come to market. This first-floor, fully renovated unit showcases elevated designer finishes throughout. A picture-window screened patio opens to an expansive lanai, surrounded by lush, tropical landscaping; creating a seamless indoor-outdoor living experience. The modern kitchen features Caesarstone “concrete” quartz countertops, an induction cooktop, built-in oven, and custom cabinetry designed for both style and functionality. Each bathroom evokes a five-star resort experience, with thoughtfully curated custom details and designer lighting in both the baths and dining area. All windows and the patio slider have been upgraded to hurricane-impact glass for added peace of mind. The major components of the unit; the air conditioner and water heater have been upgraded. The home also features air purification paint for enhanced interior air quality. One under-building parking space is included, along with a private, locked storage closet which is perfect for bikes and beach gear. Beyond the beach, residents enjoy meticulously maintained nature trails, lushly landscaped grounds, and abundant wildlife. Just steps from the residence, the well-appointed clubhouse features a Junior Olympic-sized heated pool, four Har-Tru tennis courts, a fitness center, and more. Bayport is also known for its vibrant social and recreational lifestyle. Water enthusiasts will appreciate the secluded fishing pier extending into Sarasota Bay. An ideal setting to fish, take in the sunrise, watch manatees glide by, or egrets wading through the mangroves. Paddleboard and kayak launch and storage areas are conveniently located on-site. Residents enjoy easy access to local dining, a nearby supermarket, pharmacy, and charming boutique shops. Just moments away, Bayfront Park offers a popular pickleball program, dog park, and a variety of bayside activities. The Longboat Key Club is also nearby, offering private access to championship waterfront golf, boating, and an array of leisure amenities. Within minutes, you’ll find the renowned St. Armands Circle, known for its exceptional shopping and dining. From there, cross the iconic Ringling Bridge into downtown Sarasota, celebrated for its world-class theater, culture, and culinary scene. Offered by private appointment. Inquire to experience Bayport’s timeless coastal living firsthand.

LONGBOAT KEY

828 BAYPORT WAY

2 Beds

2 Baths

1,456 Sq.Ft.

$900,000

MLS#: A4689635

Four Diamond Resort with five restaurants, 45 holes of Golf, Spa, Marina, 21 Tennis courts on Longboat Key!!!. This income producing property on the beachside with a golf course view is calling you!!!. It's a one-bedroom studio at the Resort on Longboat Key, a gated community. Presently the unit is in the Resort rental program and the owner may use the unit 28 days per year.

LONGBOAT KEY

250 SANDS POINT ROAD 5203

1 Beds

1 Baths

640 Sq.Ft.

$899,900

MLS#: A4680085

Welcome to one of Longboat Key's premier bayfront communities, Tangerine Bay Club, where your days are spent like you live at a luxury resort! This three bedroom, 2 and a half bath elevated residence offers spacious living with gorgeous views of the mote style lagoon, spectacular resort style pool and Sarasota Bay. A private 2 car garage only adds to the many benefits of living here. Did we mention the day dock and pier over Sarasota Bay? The community gym overlooking the gorgeous pool? The Tennis and pickleball courts? The ability to purchase a membership at the Bay Isles Beach club for only a nominal yearly fee? This is truly island living at its best! A welcoming front entrance courtyard allows for a wonderful arrival spot just steps from the elevator yet this unit, being a corner residence, feels very private. Once inside you'll be immediately impressed with the light filled spaces that allow for you to enjoy the incredible views from multiple large windows. A balcony accessed from the great room and the Primary bedroom is a spot you'll want to enjoy every morning with your coffee and every evening with your cold beverage. Just a short distance from multiple restaurants, the Longboat Key Club, The St.Regis resort and the bridge that takes you over to St.Armands Circle and then onto the cultural mecca of downtown Sarasota....at a price that makes it easy to imagine. Whether you choose to renovate and make it your own or enjoy it just as it is, this is one you will want to see!

LONGBOAT KEY

350 GULF OF MEXICO DRIVE 213

3 Beds

2 Baths

2,378 Sq.Ft.

$899,500

MLS#: A4696547

Direct Ocean view from this Bright Airy corner unit in desirable building five. Catch the view of the Gulf of Mexico and Sunsets from your balcony. To see this property is to fall in love with easy living! You need to visit this unit to get a sense of the remarkable views , especially the amount of light that permeates the entire interior. Beachplace is a perfect get away on the south end of Longboat Key, and comprise many amenities. Pickle Ball, Tennis, two exercise facilities, Olympic pool, with designated lap lanes, over size hot tub , covered baby pool . Electric car chargers, gas grill, two types of workout facilities on almost 31 acres of lush landscaped grounds. Please visit to see why this building and unit are the best of BEACHPLACE!

LONGBOAT KEY

1105 GULF OF MEXICO DRIVE 401

2 Beds

2 Baths

1,172 Sq.Ft.

$899,000

MLS#: A4680369

The perfect beach getaway or investment property, look no further. With stunning water views from all new windows and doors, beach access, and appealing lease policy, this 1,172 square-foot 2 bedroom, 2 bath residence in Beachplace is ready to enjoy! Watch stunning sunset views from your southwestern facing, L shaped balcony overlooking beautiful well-manicured lawn, pond, and enchanting Gulf of Mexico waters. This views can also be enjoyed while in the master bedroom. The condo residence is a corner unit, located on the 4th floor with ideal proximity to the building elevator and has wood-look tile throughout. Beachplace is perfectly located on the south end of Longboat Key, minutes from St. Armands, downtown Sarasota, SRQ Airport and much, much more. Community offers on-site management, 24-hour security, a Jr. Olympic-sized swimming pool, and newly designed hot tub area. There are lighted tennis courts, a fitness center and gas grills for the community use.

LONGBOAT KEY

1115 GULF OF MEXICO DRIVE 401

2 Beds

2 Baths

1,172 Sq.Ft.

$899,000

MLS#: A4671664

#A4683112

LONGBOAT KEY

2295 GULF OF MEXICO DRIVE 54S

2 Beds

2 Baths

1,235 Sq.Ft.

$899,000

MLS#: A4683112

TURNKEY Furnished Portobello condo with Deeded Beach Access! TWO Balconies with Sunsets AND Sunrises included! Enjoy Beach and Bayou water access! Rarely available end unit with two balconies and lots of privacy and natural lighting. The front open balcony has unobstructed Gulf views whilst the rear balcony is glassed in with sliders/screens and faces the Bayou. This 4th Floor condo has elevator access, 1 owners storage locker, ample in unit storage and 1 assigned parking space. Condo fee includes Water, Sewer, Trash, Cable/Internet, Pest Control, on site Maintenance and Exterior Insurance. Well established social community with Community Pool, Clubhouse, Tennis Courts, Kayak storage/launch, Fishing Pier, BBQ area and ELEVATED mature landscaping. This spacious floorplan is one of the larger floorpans in the community providing you with list and bright spaces, tons of closet space and even a bonus study/den area to use as you please! Stacked Washer/Dryer located near the hallway 2nd Bathroom which has been renovated. Beautifully upgraded Kitchen with high quality cabinetry and 4 storage closets for all your pantry, cleaning and large cooking items. The Primary Bedroom has the most wonderful private bayou water views! Attached en suite full bathroom with lots of counter space. Secondary bedroom has its own separate balcony entrance. This community is located a short drive away from Publix, CVS, banks, Post office, nail salons and Golfing! New development nearby is bringing more shopping and dining! Don't miss this opportunity to own in the sough after Portobello community!

LONGBOAT KEY

3240 GULF OF MEXICO DRIVE B402

2 Beds

2 Baths

1,505 Sq.Ft.

$895,000

MLS#: A4686024

#A4674248

LONGBOAT KEY

4825 GULF OF MEXICO DRIVE 202

2 Beds

2 Baths

1,393 Sq.Ft.

$890,000

MLS#: A4674248

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