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

601 Longboat Club Rd #803s, Longboat Key, FL 34228

601 Longboat Club Rd #803s

$900,000
Condo
2 bedrooms, 2 baths
1,458 Sq.Ft.
Built in 1970
-82.5981
27.3378
SLD
3040 Grand Bay Blvd #252, Longboat Key, FL 34228

3040 Grand Bay Blvd #252

$925,000
Condo
3 bedrooms, 3 baths
2,250 Sq.Ft.
Built in 1996
-82.6169
27.3764
SLD
2020 Harbourside Dr #417, Longboat Key, FL 34228

2020 Harbourside Dr #417

$580,000
Condo
2 bedrooms, 2 baths
1,442 Sq.Ft.
Built in 1984
-82.6125
27.3597
SLD
3529 Fair Oaks Ln, Longboat Key, FL 34228

3529 Fair Oaks Ln

$1,260,000
Single Family Home
5 bedrooms, 5 baths
4,373 Sq.Ft.
10,205 Sq.Ft. lot
Built in 1997
-82.6255
27.3811
SLD
1445 Gulf Of Mexico Dr #203, Longboat Key, FL 34228

1445 Gulf Of Mexico Dr #203

$540,000
Condo
2 bedrooms, 2 baths
1,642 Sq.Ft.
Built in 1982
-82.6094
27.3504
SLD
448 Gulf Of Mexico Dr #a304, Longboat Key, FL 34228

448 Gulf Of Mexico Dr #a304

$340,000
Condo
2 bedrooms, 2 baths
1,194 Sq.Ft.
Built in 1970
-82.5915
27.3393
SLD
2341 Harbour Oaks Dr, Longboat Key, FL 34228

2341 Harbour Oaks Dr

$810,000
Villa
3 bedrooms, 3 baths
2,282 Sq.Ft.
6,982 Sq.Ft. lot
Built in 1986
-82.6189
27.3653
SLD
4 Winslow Pl, Longboat Key, FL 34228

4 Winslow Pl

$1,075,000
Single Family Home
3 bedrooms, 2 baths
1,975 Sq.Ft.
13,302 Sq.Ft. lot
Built in 1963
-82.6296
27.373
SLD
5610 & 5620 Gulf Of Mexico Dr #1, Longboat Key, FL 34228

5610 & 5620 Gulf Of Mexico Dr #1

$1,125,000
Vacant Land
 
116,489 Sq.Ft. lot
-82.6406
27.3881
SLD
3660 Gulf Of Mexico Dr #205a, Longboat Key, FL 34228

3660 Gulf Of Mexico Dr #205a

$550,000
Condo
3 bedrooms, 2 baths
1,486 Sq.Ft.
Built in 1980
-82.635
27.38
SLD
Get alerts when listings matching your search become available.