Main Content

Longboat Key

Longboat Key is one of the most sought-after Sarasota real estate destinations. Stretching 11 miles over powdery white sand, this barrier island is home to many full-time residents and even more seasonal visitors. Longboat Key is packed with its own amenities, including the finest homes and condos, fine dining restaurants, shopping, and pristine beaches. For those who want to explore away from the island, Lido Key, St. Armand’s Circle, Bird Key and Downtown are just minutes away. Longboat Key also has a great social and golf facility located within the Longboat Key Club.

The style of homes on Longboat Key varies- one will find Modern, Contemporary, Mediterranean, and Classic Florida architecture. Whether you are looking for an estate, beach house, luxury condominium, or a place to retire, all can be found on Longboat Key. Have a look at the listings below to find inspiration for what might be next for you on Longboat Key.

Min. Price
Max. Price
Beds
Baths
5965 GULF OF MEXICO DRIVE LONGBOAT KEY, FL 34228
$25,000,000
11 Beds 13 | 4 Baths 17,199 Sqft Listing No. A4632544 Property Type: House camera Virtual Tour camera (63)
Details
612 JUAN ANASCO DRIVE LONGBOAT KEY, FL 34228
$24,950,000
6 Beds 7 | 2 Baths 9,243 Sqft Listing No. A4643123 Property Type: House camera Virtual Tour camera (94)
Details
5861 GULF OF MEXICO DRIVE LONGBOAT KEY, FL 34228
$20,995,000
5 Beds 6 | 1 Baths 10,400 Sqft Listing No. A4627895 Property Type: House camera Virtual Tour camera (74)
Details
6489 GULFSIDE ROAD LONGBOAT KEY, FL 34228
$16,995,000
4 Beds 4 | 1 Baths 6,616 Sqft Listing No. A4629211 Property Type: House camera Virtual Tour camera (40)
Details
5581 GULF OF MEXICO DRIVE LONGBOAT KEY, FL 34228
$15,500,000
11 Beds 9 | 2 Baths 8,529 Sqft Listing No. A4641831 Property Type: House camera (17)
Details
6603 GULFSIDE ROAD LONGBOAT KEY, FL 34228
$15,000,000
5 Beds 5 | 1 Baths 4,925 Sqft Listing No. A4648957 Property Type: House camera Virtual Tour camera (16)
Details
6680 GULF OF MEXICO DRIVE LONGBOAT KEY, FL 34228
$14,800,000
6 Beds 6 | 1 Baths 6,408 Sqft Listing No. A4583940 Property Type: House camera Virtual Tour camera (77)
Details
1561 GULF OF MEXICO DRIVE #403 LONGBOAT KEY, FL 34228
$13,250,000
3 Beds 3 | 1 Baths 4,187 Sqft Listing No. A4627926 Property Type: Condo camera (90)
Details
5919 GULF OF MEXICO DRIVE LONGBOAT KEY, FL 34228
$12,500,000
5 Beds 6 Baths 5,596 Sqft Listing No. A4628022 Property Type: House camera Virtual Tour camera (61)
Details
50 LIGHTHOUSE POINT DRIVE LONGBOAT KEY, FL 34228
$12,500,000
6 Beds 6 | 1 Baths 7,450 Sqft Listing No. A4632738 Property Type: House camera Virtual Tour camera (64)
Details
560 HARBOR POINT ROAD LONGBOAT KEY, FL 34228
$11,000,000
4 Beds 5 Baths 5,245 Sqft Listing No. A4636226 Property Type: House camera Virtual Tour camera (54)
Details
6161 GULF OF MEXICO DRIVE LONGBOAT KEY, FL 34228
$10,995,000
4 Beds 4 | 1 Baths 4,224 Sqft Listing No. A4634003 Property Type: House camera Virtual Tour camera (74)
Details
1581 GULF OF MEXICO DRIVE #508 LONGBOAT KEY, FL 34228
$10,500,000
4 Beds 4 | 1 Baths 4,017 Sqft Listing No. A4630440 Property Type: Condo camera Virtual Tour camera (98)
Details
1581 GULF OF MEXICO DRIVE #308 LONGBOAT KEY, FL 34228
$10,475,000
4 Beds 4 | 1 Baths 4,017 Sqft Listing No. A4645968 Property Type: Condo camera Virtual Tour camera (38)
Details
501 HARBOR POINT ROAD LONGBOAT KEY, FL 34228
$9,900,000
5 Beds 5 | 1 Baths 6,125 Sqft Listing No. A4625287 Property Type: House camera Virtual Tour camera (79)
Details
3341 GULF OF MEXICO DRIVE LONGBOAT KEY, FL 34228
$9,750,000
3 Beds 3 Baths 1,718 Sqft Listing No. TB8352591 Property Type: House camera Virtual Tour camera (35)
Details
3351 GULF OF MEXICO DRIVE LONGBOAT KEY, FL 34228
$9,750,000
2 Beds 1 Baths 1,276 Sqft Listing No. TB8353273 Property Type: House camera Virtual Tour camera (34)
Details
1580 HARBOR CAY LANE LONGBOAT KEY, FL 34228
$9,495,000
5 Beds 4 | 2 Baths 6,349 Sqft Listing No. A4643044 Property Type: House camera Virtual Tour camera (95)
Details
6061 GULF OF MEXICO DRIVE LONGBOAT KEY, FL 34228
$8,900,000
5 Beds 5 | 1 Baths 3,203 Sqft Listing No. A4633427 Property Type: House camera Virtual Tour camera (61)
Details
5941 GULF OF MEXICO DRIVE LONGBOAT KEY, FL 34228
$8,800,000
3 Beds 3 | 1 Baths 2,417 Sqft Listing No. A4626774 Property Type: House camera Virtual Tour camera (35)
Details
757 HIDEAWAY BAY DRIVE LONGBOAT KEY, FL 34228
$8,500,000
4 Beds 5 Baths 4,507 Sqft Listing No. A4604144 Property Type: House camera Virtual Tour camera (91)
Details
2251 GULF OF MEXICO DRIVE #203 LONGBOAT KEY, FL 34228
$7,995,000
4 Beds 4 | 1 Baths 3,961 Sqft Listing No. O6247566 Property Type: Condo camera Virtual Tour camera (39)
Details
65 LIGHTHOUSE POINT DRIVE LONGBOAT KEY, FL 34228
$7,765,000
4 Beds 4 | 1 Baths 4,941 Sqft Listing No. A4630535 Property Type: House camera Virtual Tour camera (60)
Details
500 HARBOR POINT ROAD LONGBOAT KEY, FL 34228
$7,690,000
5 Beds 6 | 1 Baths 6,556 Sqft Listing No. A4639203 Property Type: House camera Virtual Tour camera (72)
Details
 5965 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228
camera VIRTUAL TOUR camera (63)
price

$25,000,000

beds

11 11 Beds

baths

13 | 4 13 | 4 Baths

lot size

17,199 Sqft 17,199 Sqft

listing no.

A4632544 Listing No. A4632544

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (63)

 612 JUAN ANASCO DRIVE, LONGBOAT KEY, FL 34228
camera VIRTUAL TOUR camera (94)
price

$24,950,000

beds

6 6 Beds

baths

7 | 2 7 | 2 Baths

lot size

9,243 Sqft 9,243 Sqft

listing no.

A4643123 Listing No. A4643123

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (94)

 5861 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228
camera VIRTUAL TOUR camera (74)
price

$20,995,000

beds

5 5 Beds

baths

6 | 1 6 | 1 Baths

lot size

10,400 Sqft 10,400 Sqft

listing no.

A4627895 Listing No. A4627895

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (74)

 6489 GULFSIDE ROAD, LONGBOAT KEY, FL 34228
camera VIRTUAL TOUR camera (40)
price

$16,995,000

beds

4 4 Beds

baths

4 | 1 4 | 1 Baths

lot size

6,616 Sqft 6,616 Sqft

listing no.

A4629211 Listing No. A4629211

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (40)

 5581 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228
camera (17)
price

$15,500,000

beds

11 11 Beds

baths

9 | 2 9 | 2 Baths

lot size

8,529 Sqft 8,529 Sqft

listing no.

A4641831 Listing No. A4641831

property type

House Property Type: House

gallery photos

camera (17)

 6603 GULFSIDE ROAD, LONGBOAT KEY, FL 34228
camera VIRTUAL TOUR camera (16)
price

$15,000,000

beds

5 5 Beds

baths

5 | 1 5 | 1 Baths

lot size

4,925 Sqft 4,925 Sqft

listing no.

A4648957 Listing No. A4648957

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (16)

 6680 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228
camera VIRTUAL TOUR camera (77)
price

$14,800,000

beds

6 6 Beds

baths

6 | 1 6 | 1 Baths

lot size

6,408 Sqft 6,408 Sqft

listing no.

A4583940 Listing No. A4583940

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (77)

 1561 GULF OF MEXICO DRIVE #403, LONGBOAT KEY, FL 34228
camera (90)
price

$13,250,000

beds

3 3 Beds

baths

3 | 1 3 | 1 Baths

lot size

4,187 Sqft 4,187 Sqft

listing no.

A4627926 Listing No. A4627926

property type

Condo Property Type: Condo

gallery photos

camera (90)

 5919 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228
camera VIRTUAL TOUR camera (61)
price

$12,500,000

beds

5 5 Beds

baths

6 6 Baths

lot size

5,596 Sqft 5,596 Sqft

listing no.

A4628022 Listing No. A4628022

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (61)

 50 LIGHTHOUSE POINT DRIVE, LONGBOAT KEY, FL 34228
camera VIRTUAL TOUR camera (64)
price

$12,500,000

beds

6 6 Beds

baths

6 | 1 6 | 1 Baths

lot size

7,450 Sqft 7,450 Sqft

listing no.

A4632738 Listing No. A4632738

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (64)

 560 HARBOR POINT ROAD, LONGBOAT KEY, FL 34228
camera VIRTUAL TOUR camera (54)
price

$11,000,000

beds

4 4 Beds

baths

5 5 Baths

lot size

5,245 Sqft 5,245 Sqft

listing no.

A4636226 Listing No. A4636226

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (54)

 6161 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228
camera VIRTUAL TOUR camera (74)
price

$10,995,000

beds

4 4 Beds

baths

4 | 1 4 | 1 Baths

lot size

4,224 Sqft 4,224 Sqft

listing no.

A4634003 Listing No. A4634003

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (74)

 1581 GULF OF MEXICO DRIVE #508, LONGBOAT KEY, FL 34228
camera VIRTUAL TOUR camera (98)
price

$10,500,000

beds

4 4 Beds

baths

4 | 1 4 | 1 Baths

lot size

4,017 Sqft 4,017 Sqft

listing no.

A4630440 Listing No. A4630440

property type

Condo Property Type: Condo

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (98)

 1581 GULF OF MEXICO DRIVE #308, LONGBOAT KEY, FL 34228
camera VIRTUAL TOUR camera (38)
price

$10,475,000

beds

4 4 Beds

baths

4 | 1 4 | 1 Baths

lot size

4,017 Sqft 4,017 Sqft

listing no.

A4645968 Listing No. A4645968

property type

Condo Property Type: Condo

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (38)

 501 HARBOR POINT ROAD, LONGBOAT KEY, FL 34228
camera VIRTUAL TOUR camera (79)
price

$9,900,000

beds

5 5 Beds

baths

5 | 1 5 | 1 Baths

lot size

6,125 Sqft 6,125 Sqft

listing no.

A4625287 Listing No. A4625287

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (79)

 3341 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228
camera VIRTUAL TOUR camera (35)
price

$9,750,000

beds

3 3 Beds

baths

3 3 Baths

lot size

1,718 Sqft 1,718 Sqft

listing no.

TB8352591 Listing No. TB8352591

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (35)

 3351 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228
camera VIRTUAL TOUR camera (34)
price

$9,750,000

beds

2 2 Beds

baths

1 1 Baths

lot size

1,276 Sqft 1,276 Sqft

listing no.

TB8353273 Listing No. TB8353273

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (34)

 1580 HARBOR CAY LANE, LONGBOAT KEY, FL 34228
camera VIRTUAL TOUR camera (95)
price

$9,495,000

beds

5 5 Beds

baths

4 | 2 4 | 2 Baths

lot size

6,349 Sqft 6,349 Sqft

listing no.

A4643044 Listing No. A4643044

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (95)

 6061 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228
camera VIRTUAL TOUR camera (61)
price

$8,900,000

beds

5 5 Beds

baths

5 | 1 5 | 1 Baths

lot size

3,203 Sqft 3,203 Sqft

listing no.

A4633427 Listing No. A4633427

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (61)

 5941 GULF OF MEXICO DRIVE, LONGBOAT KEY, FL 34228
camera VIRTUAL TOUR camera (35)
price

$8,800,000

beds

3 3 Beds

baths

3 | 1 3 | 1 Baths

lot size

2,417 Sqft 2,417 Sqft

listing no.

A4626774 Listing No. A4626774

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (35)

 757 HIDEAWAY BAY DRIVE, LONGBOAT KEY, FL 34228
camera VIRTUAL TOUR camera (91)
price

$8,500,000

beds

4 4 Beds

baths

5 5 Baths

lot size

4,507 Sqft 4,507 Sqft

listing no.

A4604144 Listing No. A4604144

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (91)

 2251 GULF OF MEXICO DRIVE #203, LONGBOAT KEY, FL 34228
camera VIRTUAL TOUR camera (39)
price

$7,995,000

beds

4 4 Beds

baths

4 | 1 4 | 1 Baths

lot size

3,961 Sqft 3,961 Sqft

listing no.

O6247566 Listing No. O6247566

property type

Condo Property Type: Condo

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (39)

 65 LIGHTHOUSE POINT DRIVE, LONGBOAT KEY, FL 34228
camera VIRTUAL TOUR camera (60)
price

$7,765,000

beds

4 4 Beds

baths

4 | 1 4 | 1 Baths

lot size

4,941 Sqft 4,941 Sqft

listing no.

A4630535 Listing No. A4630535

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (60)

 500 HARBOR POINT ROAD, LONGBOAT KEY, FL 34228
camera VIRTUAL TOUR camera (72)
price

$7,690,000

beds

5 5 Beds

baths

6 | 1 6 | 1 Baths

lot size

6,556 Sqft 6,556 Sqft

listing no.

A4639203 Listing No. A4639203

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (72)

© 2025 Stellar MLS. All rights reserved.
The data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; the availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.
Stellar (MFR) data last updated at April 18, 2025, 10:40 PM ET
Real Estate IDX Powered by iHomefinder