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

5 Winslow Pl, Longboat Key, FL 34228

5 Winslow Pl

$1,025,000
Single Family Home
3 bedrooms, 3 baths
1,711 Sq.Ft.
13,501 Sq.Ft. lot
Built in 1962
-82.63
27.3733
SLD
4350 Chatham Dr #e308, Longboat Key, FL 34228

4350 Chatham Dr #e308

$339,000
Condo
2 bedrooms, 2 baths
1,316 Sq.Ft.
Built in 1969
-82.6455
27.3962
SLD
4621 Gulf Of Mexico Dr #18f, Longboat Key, FL 34228

4621 Gulf Of Mexico Dr #18f

$350,000
Condo
2 bedrooms, 2 baths
900 Sq.Ft.
Built in 1973
-82.6474
27.3976
SLD
635 Marbury Ln, Longboat Key, FL 34228

635 Marbury Ln

$700,000
Single Family Home
3 bedrooms, 3 baths
2,446 Sq.Ft.
9,840 Sq.Ft. lot
Built in 1958
-82.6725
27.4278
SLD
4330 Falmouth Dr #205, Longboat Key, FL 34228

4330 Falmouth Dr #205

$178,000
Condo
1 bedroom, 1 bath
747 Sq.Ft.
Built in 1969
-82.6455
27.3962
SLD
408 Gulf Of Mexico Dr #2316, Longboat Key, FL 34228

408 Gulf Of Mexico Dr #2316

$31,900
Single Family Home
 
26,052 Sq.Ft. lot
-82.5899
27.3388
SLD
585 Cutter Ln, Longboat Key, FL 34228

585 Cutter Ln

$1,065,000
Single Family Home
3 bedrooms, 2 baths
2,681 Sq.Ft.
12,051 Sq.Ft. lot
Built in 1973
-82.5957
27.3425
SLD
5211 Gulf Of Mexico Dr #101, Longboat Key, FL 34228

5211 Gulf Of Mexico Dr #101

$640,000
Condo
3 bedrooms, 2 baths
1,363 Sq.Ft.
Built in 1976
-82.6554
27.4073
SLD
200 Sands Point Rd #1102, Longboat Key, FL 34228

200 Sands Point Rd #1102

$1,025,000
Single Family Home
2 bedrooms, 2 baths
1,311 Sq.Ft.
Built in 1982
-82.5908
27.3303
SLD
4401 Gulf Of Mexico Dr #802, Longboat Key, FL 34228

4401 Gulf Of Mexico Dr #802

$685,000
Condo
2 bedrooms, 2 baths
1,034 Sq.Ft.
Built in 1972
-82.6443
27.3936
SLD
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