As much an international destination as it is a beloved favorite among visitors and residents from all over the U.S., Longboat Key's span crosses through both Sarasota and Manatee Counties. This magnificent length of shoreline got its first road courtesy of circus magnate John Ringling in 1925. Originally, it extended only from New Pass at the southernmost tip to the Manatee County line, but Ringling envisioned a beautifully landscaped boulevard that would run the full length of the barrier island. ... more.Today's Gulf of Mexico Drive is the magnificently landscaped thoroughfare that Ringling had imagined. It winds past splendid homes and condominiums, lush greenways and parks, hidden driveways and side streets, yacht basins and captivating stretches of the Gulf of Mexico. Along both sides are discreet shopping plazas—filled with upscale shopping and fine dining—and the emerald-shaded fairways that comprise the two championship courses of the Longboat Key Club.

Nearby

4380 Exeter Dr #h-306, Longboat Key, FL 34228

4380 Exeter Dr #h-306

$320,000
Condo
2 bedrooms, 2 baths
1,168 Sq.Ft.
Built in 1970
-82.6455
27.3962
SLD
230 Sands Point Rd #3603, Longboat Key, FL 34228

230 Sands Point Rd #3603

$465,000
Condo
1 bedroom, 1 bath
634 Sq.Ft.
Built in 1982
-82.5908
27.3303
SLD
200 Sands Point Rd #1203, Longboat Key, FL 34228

200 Sands Point Rd #1203

$525,000
Condo
1 bedroom, 1 bath
638 Sq.Ft.
Built in 1982
-82.5908
27.3303
SLD
4410 Exeter Dr #306, Longboat Key, FL 34228

4410 Exeter Dr #306

$373,000
Condo
2 bedrooms, 2 baths
1,376 Sq.Ft.
Built in 1970
-82.6455
27.3962
SLD
701 Emerald Harbor Dr, Longboat Key, FL 34228

701 Emerald Harbor Dr

$739,000
Single Family Home
3 bedrooms, 2 baths
2,376 Sq.Ft.
15,000 Sq.Ft. lot
Built in 1972
-82.6646
27.422
SLD
3040 Grand Bay Blvd #246, Longboat Key, FL 34228

3040 Grand Bay Blvd #246

$1,650,000
Condo
3 bedrooms, 3 baths
2,925 Sq.Ft.
Built in 1996
-82.617
27.3766
SLD
4330 Falmouth Dr #c101, Longboat Key, FL 34228

4330 Falmouth Dr #c101

$333,500
Condo
2 bedrooms, 2 baths
1,092 Sq.Ft.
Built in 1969
-82.6455
27.3962
SLD
521 Ranger Ln, Longboat Key, FL 34228

521 Ranger Ln

$1,325,000
Single Family Home
3 bedrooms, 3 baths
3,550 Sq.Ft.
10,013 Sq.Ft. lot
Built in 2016
-82.601
27.3455
SLD
4234 Gulf Of Mexico Dr #l2, Longboat Key, FL 34228

4234 Gulf Of Mexico Dr #l2

$430,000
Condo
2 bedrooms, 2 baths
1,150 Sq.Ft.
Built in 1973
-82.6413
27.3916
SLD
210 Sands Point Rd #2601, Longboat Key, FL 34228

210 Sands Point Rd #2601

$1,225,000
Condo
2 bedrooms, 2 baths
1,380 Sq.Ft.
Built in 1982
-82.5908
27.3303
SLD
Get alerts when listings matching your search become available.