Longboat Key, FL Homes

/50
$849,999
- 2 Beds
- 2 Baths
- 1,559 Sq Ft
4600 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

Exquisite Bayfront Living with Unparalleled Panoramic ViewsImmerse yourself in breathtaking day-to-night bay views from every room in this impeccably maintained 2-bedroom, 2-bathroom corner end-unit condo (1,523 SF). Boasting the largest floor plan in the community, this elevated 2nd-floor retreat, effortlessly combines elegance, comfort, and the beauty of its natural surroundings —accessible

Oday Marogi

KELLER WILLIAMS ON THE WATER S

(941) 394-8427

4600 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
/60
$9,500 per month
- 2 Beds
- 2 Baths
- 1,456 Sq Ft
- Condo for Rent
744 Bayport Way Unit 744, Longboat Key, FL 34228

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

Antonietta Car

KELLER WILLIAMS SUBURBAN TAMPA

(941) 294-6846

744 Bayport Way Unit 744, Longboat Key, FL 34228
/2
$727,500 Sold May 02, 2025
- 1,068 Sq Ft
- $681/SF
- 44 Days On Market
- 2 Beds
- 2 Baths
- Built 1977
1965 Gulf of Mexico Dr Unit G5405, Longboat Key, FL 34228

Welcome to your dream coastal retreat! This beautifully renovated 2-bedroom, 2-bathroom condo on the top floor of G-5 Building in Seaplace offers breathtaking Gulf and beach views from the lanai, complete with new tile floor and a ceiling fan to enjoy the sea breeze in comfort. With its beachfront location and top-floor setting featuring elevated ceilings, this residence embodies the essence of

Kevin Tai PREFERRED SHORE LLC

1965 Gulf of Mexico Dr Unit G5405, Longboat Key, FL 34228

/51
Est $318,344 Not Listed For Sale
- 2 Beds
- 2 Baths
- 741 Sq Ft
104 Twin Shores Blvd, Longboat Key, FL 34228

104 Twin Shores Blvd, Longboat Key, FL 34228

/33
$550,000
- 2 Beds
- 1 Bath
- 933 Sq Ft
1935 Gulf of Mexico Dr Unit G7304, Longboat Key, FL 34228

Experience the best of coastal living in this beautifully maintained 2-bedroom, 1-bathroom condominium, perfectly situated on the third floor of the desirable Seaside community on Longboat Key. Set within a secure, 24-hour guard-gated enclave, this charming residence offers both privacy and peace of mind. Step inside to discover a light and airy interior that was tastefully repainted in April

Alie Espinoza

EATON REALTY

(941) 531-9855

1935 Gulf of Mexico Dr Unit G7304, Longboat Key, FL 34228
/24
$8,000 per month
- 2 Beds
- 2 Baths
- 1,336 Sq Ft
- Condo for Rent
4325 Gulf of Mexico Dr Unit 406, Longboat Key, FL 34228

Don't miss this one! Now available for the Feb 2025 then April forward. February @ $10,000 and April @ $8000/month, May through Nov $6000. Direct Gulf Front Rental. Gorgeously renovated condo, new luxury vinyl flooring and couches including a pull out for extra guests (new pictures coming soon) 2 bedrooms, 2 baths. The renovated kitchen is complete with marble countertops. This beach retreat has

Greg Martin

STERLING REALTY

(941) 239-1635

4325 Gulf of Mexico Dr Unit 406, Longboat Key, FL 34228
/2
$650,000 Sold May 02, 2025
- 1,172 Sq Ft
- $555/SF
- 112 Days On Market
- 2 Beds
- 2 Baths
- Built 1981
1085 Gulf of Mexico Dr Unit 301, Longboat Key, FL 34228

Overlooking the Longboat Key Club golf course and only steps to the beach, this updated, modern END UNIT is offered TURNKEY FURNISHED. Situated on 31 pristine acres and 1450 feet of private beach in AWARD-WINNING Beachplace, you’ll enjoy long peaceful walks on the beach and outstanding sunsets. The unit’s southwest orientation with peek-a-boo views of the Gulf of Mexico affords privacy and full

Phillip Wasson BRIGHT REALTY

1085 Gulf of Mexico Dr Unit 301, Longboat Key, FL 34228

/53
Est $801,710 Not Listed For Sale
- 1 Bed
- 1 Bath
- 642 Sq Ft
225 Sands Point Rd Unit 6106, Longboat Key, FL 34228

225 Sands Point Rd Unit 6106, Longboat Key, FL 34228

/88
$3,795,500 Pending
- 4 Beds
- 3.5 Baths
- 3,436 Sq Ft
531 Ranger Ln, Longboat Key, FL 34228

Nestled in the sought-after Country Club Shores on Longboat Key, this exquisite waterfront residence is your gateway to luxury living. This home provides direct BOAT ACCESS with a private DOCK and features DEEDED BEACH ACCESS for endless coastal adventures. This elegant Florida-friendly floor plan features a FIRST FLOOR MASTER suite and office, TWO spacious bedrooms on the second level, plus an

Paulina Vasiliev

KELLER WILLIAMS ON THE WATER S

(941) 239-1070

531 Ranger Ln, Longboat Key, FL 34228
/54
$9,500 per month
- 2 Beds
- 2 Baths
- 1,260 Sq Ft
- Condo for Rent
517 Bayport Way Unit 517, Longboat Key, FL 34228

Gorgeous Inside! Furnished Rental at the exceptional Bayport Beach and Tennis Club. Single story end unit with private entrance. Very Private screened lanai and patio area. Amenities abound at this beautifully landscaped Beach and Tennis Club. Four professional quality Hart-Tru Clay Courts with ball machine, Junior Olympic (heated) swimming pool, ping pong table, bocce ball court, fitness

Antonietta Car

KELLER WILLIAMS SUBURBAN TAMPA

(941) 325-0092

517 Bayport Way Unit 517, Longboat Key, FL 34228
/2
$3,450,000 Sold May 01, 2025
- 3,199 Sq Ft
- $1078/SF
- 24 Days On Market
- 3 Beds
- 4 Baths
- Built 2023
608 Bayview Dr, Longboat Key, FL 34228

Along the tranquil shores of Gull Bayou, 608 Bayview Drive on Longboat Key offers an unparalleled blend of waterfront luxury and island living. With approximately 100 feet of direct water frontage, this exquisite home boasts breathtaking views of the bayou, where herons, ospreys and pelicans create a serene natural backdrop. A boater’s dream, the property provides easy access to the Intracoastal

Joel Schemmel PREMIER SOTHEBYS INTL REALTY

608 Bayview Dr, Longboat Key, FL 34228

/21
Est $2,613,148 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,420 Sq Ft
601 Longboat Club Rd Unit 1101S, Longboat Key, FL 34228

601 Longboat Club Rd Unit 1101S, Longboat Key, FL 34228

/38
$1,370,000
- Land
- 0.41 Acre
- $3,341,463 per Acre
560 Gulf Bay Rd, Longboat Key, FL 34228

RARE DOUBLE-SIZED ESTATE LOT ON LONGBOAT KEY – 18,000 SQ FT OF ISLAND LUXURY READY FOR YOUR VISION. Opportunities like this are few and far between. Nestled in one of the most coveted areas of Longboat Key, this expansive 18,000-square-foot estate lot at 560 Gulf Bay Road offers a blank canvas for your dream coastal retreat—just steps from the sugar-white sands of the Gulf of Mexico. Perfectly

Gregory Claxton

PREFERRED SHORE LLC

(941) 352-8416

560 Gulf Bay Rd, Longboat Key, FL 34228
/66
$10,000 per month
- 2 Beds
- 2 Baths
- 1,601 Sq Ft
- Condo for Rent
832 Bayport Way Unit 832, Longboat Key, FL 34228

BAYPORT BEACH and TENNIS CLUB, a Gulf to Bay, FULLY FURNISHED 2/2 residence. Bayport is an award winning community situated in theheart of Longboat Key. A friendly, popular, residential enclave of 136 quality-constructed homes on 27 picturesque acres of impeccablymaintained grounds. Tastefully decorated and well maintained with over 1600 square feet of living area; perfect for

Antonietta Car

KELLER WILLIAMS SUBURBAN TAMPA

(941) 207-3341

832 Bayport Way Unit 832, Longboat Key, FL 34228
/2
$900,000 Sold Apr 30, 2025
- 2,608 Sq Ft
- $345/SF
- 0 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1988
3460 Winding Oaks Dr Unit 38, Longboat Key, FL 34228

Winding Oaks at Bay Isles is a gated community on Longboat Key, FL. Residents have access to the Bay Isles Beach Club, and there is also an optional membership to the Longboat Key Club. The community provides amenities such as a pool and tennis courts, with convenient access to the Gulf of Mexico, local dining, and shopping.

Bruce Myer COLDWELL BANKER REALTY

3460 Winding Oaks Dr Unit 38, Longboat Key, FL 34228

/73
Est $617,629 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,257 Sq Ft
2089 Gulf of Mexico Dr Unit G1303, Longboat Key, FL 34228

2089 Gulf of Mexico Dr Unit G1303, Longboat Key, FL 34228

/6
$649,000
- Land
- 0.14 Acre
- $4,635,714 per Acre
6981 Lois Ave, Longboat Key, FL 34228

LOCATION ALERT!!! Build your dream home on this 6,000 sq ft vacant residential lot. This spacious lot offers a creative, vast playground of architectural possibilities and also those famous and coveted gorgeous, Gulf sunsets and sunrises. You are located in the heart of The Village in Longboat Key, convenient walking distance to fabulous restaurants like The Shore, Mar Vista and Whitney's. The

Jason Sato

SATO REAL ESTATE INC.

(941) 763-6831

6981 Lois Ave, Longboat Key, FL 34228
/72
$10,500 per month
- 2 Beds
- 2 Baths
- 1,601 Sq Ft
- Condo for Rent
739 Bayport Way Unit 739, Longboat Key, FL 34228

This beautifully remodeled end unit condo, boasts two bedrooms, two bathrooms and has an open concept floor plan which features anexpansive Living/Dining/Kitchen combo. In addition, it has a generous sized master bedroom with en suite bathroom, an alcove thataccommodates a small desk and a private lanai leading off the bedroom. Begin each day by enjoying nature's' most beautiful the

Antonietta Car

KELLER WILLIAMS SUBURBAN TAMPA

(941) 393-0590

739 Bayport Way Unit 739, Longboat Key, FL 34228
/2
$1,010,000 Sold Apr 30, 2025
- 2,219 Sq Ft
- $455/SF
- 52 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1984
2129 Harbourside Dr Unit 901, Longboat Key, FL 34228

Nestled in the prestigious Harbour Oaks community on Longboat Key, this 3BR/2.5BA, 2,219 sq. ft. residence blends elegance, comfort, and stunning golf course views. A private, 2 car garage and gracious entryway lead to rich wood floors, soaring ceilings, and recessed lighting. Walls of glass invite natural light while framing breathtaking views of the Harbourside Golf Course. The spacious living

Bruce Myer COLDWELL BANKER REALTY

2129 Harbourside Dr Unit 901, Longboat Key, FL 34228

/84
Est $3,233,145 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,430 Sq Ft
552 Ranger Ln, Longboat Key, FL 34228

552 Ranger Ln, Longboat Key, FL 34228

/10
$899,000
- Land
- 0.28 Acre
- $3,210,714 per Acre
771 Broadway St, Longboat Key, FL 34228

LOCATION ALERT!!! Build your dream home on this 12,000 sq ft vacant residential lot. This spacious lot offers a creative, vast playground of architectural possibilities and also those famous and coveted gorgeous, Gulf sunsets and sunrises. You are located in the heart of The Village in Longboat Key, convenient walking distance to fabulous restaurants like The Shore, Mar Vista and Whitney's. The

Jason Sato

SATO REAL ESTATE INC.

(941) 368-4323

771 Broadway St, Longboat Key, FL 34228
/71
$10,000 per month
- 2 Beds
- 2 Baths
- 1,601 Sq Ft
- Condo for Rent
838 Bayport Way Unit 838, Longboat Key, FL 34228

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

Antonietta Car

KELLER WILLIAMS SUBURBAN TAMPA

(941) 352-9696

838 Bayport Way Unit 838, Longboat Key, FL 34228
/2
$2,650,000 Sold Apr 30, 2025
- 3,054 Sq Ft
- $868/SF
- 45 Days On Market
- 2 Beds
- 4 Baths
- Built 1999
1281 Gulf of Mexico Dr Unit 703, Longboat Key, FL 34228

Looking for that unique beachfront retreat? Why not design it yourself! With breathtaking views spanning from the Gulf of Mexico to Sarasota Bay, this three-bedroom, four-bath retreat spans over 3,000 square feet and offers the ideal canvas to create a one-of-a-kind coastal masterpiece tailored to your vision. With the shimmering Gulf of Mexico to the west, Water Club's world-class amenities

Jo Rutstein PREMIER SOTHEBYS INTL REALTY

1281 Gulf of Mexico Dr Unit 703, Longboat Key, FL 34228

/13
Est $1,036,232 Not Listed For Sale
- 1 Bed
- 1 Bath
- 642 Sq Ft
210 Sands Point Rd Unit 2502, Longboat Key, FL 34228

210 Sands Point Rd Unit 2502, Longboat Key, FL 34228

/69
$865,000
- 2 Beds
- 2 Baths
- 1,685 Sq Ft
523 Bayport Way Unit 523, Longboat Key, FL 34228

Introducing an impeccably remodeled FULLY FURNSHED residence located in the beautiful community of Bayport Beach and Tennis Club. This property can be described as extraordinary, as it showcases an exquisite blend of contemporary updates and timeless appeal. The remodeling process, which took place in 2024, has intelligently infused the home with stylish and sustainability-minded attributes. You

Antonietta Car

KELLER WILLIAMS SUBURBAN TAMPA

(941) 231-7042

523 Bayport Way Unit 523, Longboat Key, FL 34228
/87
$6,000 per month
- 2 Beds
- 2 Baths
- 1,601 Sq Ft
- Condo for Rent
817 Bayport Way Unit 817, Longboat Key, FL 34228

STUNNING BAY VIEWS! Enjoy picturesque sunrises from your private deck in this tastefully decorated 2 bedroom, 2 bathroom furnished condominium. This home has an open concept floor plan which features an expansive Living/Dining/Kitchen area. The generous size master bedroom with adjoining bathroom includes a double vanity, separate shower, a walk-in closet and a small alcove that accommodates a

Antonietta Car

KELLER WILLIAMS SUBURBAN TAMPA

(941) 732-8949

817 Bayport Way Unit 817, Longboat Key, FL 34228
/2
$515,000 Sold Apr 30, 2025
- 933 Sq Ft
- $552/SF
- 61 Days On Market
- 2 Beds
- 2 Baths
- Built 1977
1975 Gulf of Mexico Dr Unit G4306, Longboat Key, FL 34228

Price Reduction offers a great opportunity to own on the beach in a fully furnished and renovated two bedroom condominium on Longboat Key. Nestled in the highly sought-after Seaplace community - located on the pristine beaches of Longboat. This bright and beautifully updated two-bedroom, two-bath condominium offers a coastal retreat - just steps to the beach. Be greeted with a generous open

Ellen Kirkegaard PREMIER SOTHEBYS INTL REALTY

1975 Gulf of Mexico Dr Unit G4306, Longboat Key, FL 34228

/25
Est $1,030,838 Not Listed For Sale
- 1 Bed
- 1 Bath
- 634 Sq Ft
230 Sands Point Rd Unit 3503, Longboat Key, FL 34228

230 Sands Point Rd Unit 3503, Longboat Key, FL 34228

/2
$6,900,000
- Land
- 0.98 Acre
- $7,040,816 per Acre
5451 Gulf of Mexico Dr, Longboat Key, FL 34228

Rare almost one acre direct Gulf front lot on the beach on the beautiful island of Longboat Key. New Gulf front homes on this key typically start at $16 million plus. There is currently an existing single level motel on the property which would need to be removed. Expected use of property is for a luxury single family home. Property also allows 1 or 2 additional family structures. Nice if you

Daniel Robinson

HOUWZER INC

(941) 368-4123

5451 Gulf of Mexico Dr, Longboat Key, FL 34228
/11
$3,200 per month
- 1 Bed
- 1 Bath
- 836 Sq Ft
- Condo for Rent
600 Sutton Place Unit 201, Longboat Key, FL 34228

Sarasota Bay view. 1 Bedroom x 1 1/2 Bathroom Condo. Living Room looks out over the pool that sits on Sarasota Bay. Fully furnished. 90 day minimum rental period. Prefer 6 mo.- 1 year rental. Sutton Place has many amenities including two heated pools, bicycle storage, outdoor grills, Gulf beach access with beach house, 1 assigned parking spot and several shared guest spaces. Boat docks

Tracy Srodes

FINE PROPERTIES

(941) 335-6064

600 Sutton Place Unit 201, Longboat Key, FL 34228
/2
$1,100,000 Sold Apr 30, 2025
- 1,827 Sq Ft
- $602/SF
- 87 Days On Market
- 2 Beds
- 2 Baths
- Built 1985
1211 Gulf of Mexico Dr Unit 108, Longboat Key, FL 34228

Sunny southern views and serene courtyard vistas welcome you to this nearly 2,000-square-foot, two-bedroom beach retreat. Meticulously updated, this elegant residence has been thoughtfully designed to enhance coastal living. Nearly every detail has been refreshed, including newer kitchen and bathrooms, freshly painted interior, and luxury vinyl plank flooring throughout. The open floor plan is

Roger Pettingell COLDWELL BANKER REALTY

1211 Gulf of Mexico Dr Unit 108, Longboat Key, FL 34228

/56
Est $1,046,594 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,239 Sq Ft
4311 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228

4311 Gulf of Mexico Dr Unit 304, Longboat Key, FL 34228

/99
$19,500,000 New Construction
- 5 Beds
- 6.5 Baths
- 10,400 Sq Ft
5861 Gulf of Mexico Dr, Longboat Key, FL 34228

Welcome to 5861 Gulf of Mexico Drive, a contemporary home that exudes Zen-like calm in a tropical jungle garden located on over an acre beachfront estate on Longboat Key. This masterpiece of tropical modernism spans a stunning 1.1 acres with 100 feet of direct Gulf frontage, offering privacy, breathtaking views, and a sophisticated lifestyle experience. Seclusion and privacy begin with an eight

Jason Sato

SATO REAL ESTATE INC.

(941) 326-4954

5861 Gulf of Mexico Dr, Longboat Key, FL 34228
/48
$9,000 per month
- 2 Beds
- 2 Baths
- 1,456 Sq Ft
- Condo for Rent
830 Bayport Way Unit 830, Longboat Key, FL 34228

Beautifully appointed seasonal/short term rental at Bayport Beach and Tennis Club on Longboat Key. This spacious 2/2 residence comes turnkey furnished and equipped with flat screen TV's, cable and WiFi. This residence features a large outdoor patio with garden views and plenty of seating. Bayport sits on 27 lushly landscaped acres and has 1200 feet of private beach. Complimentary beach chairs and

Antonietta Car

KELLER WILLIAMS SUBURBAN TAMPA

(941) 207-4978

830 Bayport Way Unit 830, Longboat Key, FL 34228
/2
$719,000 Sold Apr 30, 2025
- 1,022 Sq Ft
- $704/SF
- 155 Days On Market
- 2 Beds
- 2 Baths
- Built 1973
4485 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228

STUNNING 2-BEDROOM, 2-BATH BEACHFRONT CONDO WITH UNPARALLELED FULL GULF VIEWS! This beautifully furnished, 4th-floor condo offers sweeping, direct views of the Gulf of Mexico from every room. Located in the sought-after Arbomar community, this residence features an open floor plan with tasteful updates throughout, including newer vinyl plank flooring, crown molding, and a charming shiplap accent

Jay Travis RE/MAX ALLIANCE GROUP

4485 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228

/68
Est $714,019 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,312 Sq Ft
4960 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228

4960 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228

/72
$1,769,000
- 3 Beds
- 2 Baths
- 1,896 Sq Ft
2675 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228

Veinte (20 in Spanish) is a luxury condominium community with only twenty residents located on the beautiful and unique Longboat Key.Magnificent direct gulf views from all main rooms; electric hurricane shutters on lanai and bedrooms, electric lanai screen, and custom shades on all windows. Coming furnished with under building parking. This is a magnificent residence that you will love once you

Sandra Endres COLDWELL BANKER REALTY

2675 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228
/62
$10,000 per month
- 2 Beds
- 2 Baths
- 1,426 Sq Ft
- Condo for Rent
741 Bayport Way Unit 741, Longboat Key, FL 34228

ABSOLUTELY GORGEOUS INSIDE! 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

Antonietta Car

KELLER WILLIAMS SUBURBAN TAMPA

(941) 207-8515

741 Bayport Way Unit 741, Longboat Key, FL 34228
/2
$2,300,000 Sold Apr 30, 2025
- 1,619 Sq Ft
- $1421/SF
- 275 Days On Market
- 2 Beds
- 2 Baths
- Built 1982
240 Sands Point Rd Unit 4507, Longboat Key, FL 34228

Welcome to your dream condo at the Longboat Key Club! This recently remodeled unit offers unobstructed views of the Gulf of Mexico, providing a daily spectacle of stunning sunsets and tranquil ocean waves. The living room is a paradise with floor-to-ceiling windows that frame the breathtaking seascape, making every moment at home feel like a vacation. Step outside and indulge in the club's

Leticia Diaz KELLER WILLIAMS ON THE WATER

240 Sands Point Rd Unit 4507, Longboat Key, FL 34228

/25
Est $719,465 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,523 Sq Ft
4960 Gulf of Mexico Dr Unit A206, Longboat Key, FL 34228

4960 Gulf of Mexico Dr Unit A206, Longboat Key, FL 34228

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