This 11-mile stretch of beach-to-bay resort living boasts a variety of great homes: sprawling beach front mansions, chic million-dollar condominiums, wooden bungalows, cozy canal homes, vacation rentals, and casual low-rise condos. Gulf of Mexico Drive, which runs the length of the island, is lined with colorful flowers and banyan trees and bordered by a popular bike and jogging trail. Many people call Longboat Key home year-round, while others visit seasonally.

While some beaches on the island are private, there are many public access points.  Many take advantage of the clear blue waters for boating, swimming, fishing, parasailing, and jet skiing or some enjoy land activities like golfing and tennis.

Longboat Key

Click the links below to sort results by price range.

• All Listings
• $200,000 - $300,000
• $300,000 - $400,000
• $400,000 - $500,000
• $500,000 - $600,000
• Over $1,000,000

Bedrooms

Bathrooms

Price Range

Save Search

Sort by:

Price, high to low

$18,500,000

5861 Gulf Of Mexico Drive, LONGBOAT KEY

5 Beds 7 Baths 6,950 SqFt Residential MLS® # O6080850

$12,995,000

1620 Gulf Of Mexico Drive 502, LONGBOAT KEY

3 Beds 4 Baths 4,992 SqFt Residential MLS® # A4570079

$11,500,000

2251 Gulf Of Mexico Drive 203, LONGBOAT KEY

4 Beds 5 Baths 3,961 SqFt Residential MLS® # O6104449

$10,500,000

2251 Gulf Of Mexico Drive 204, LONGBOAT KEY

3 Beds 4 Baths 4,032 SqFt Residential MLS® # A4569602

$6,800,000

4765 Gulf Of Mexico Drive A103, LONGBOAT KEY

4 Beds 5 Baths 3,640 SqFt Residential MLS® # A4570192

$6,750,000

↓ $250,000

876 Tarawitt Drive, LONGBOAT KEY

4 Beds 3 Baths 3,040 SqFt Residential MLS® # A4564430

$6,125,000

4765 Gulf Of Mexico Drive C301, LONGBOAT KEY

4 Beds 5 Baths 3,640 SqFt Residential MLS® # A4570624

$5,750,000

↓ $200,000

2399 Gulf Of Mexico Drive 3c1, LONGBOAT KEY

4 Beds 5 Baths 4,018 SqFt Residential MLS® # A4563368

$4,200,000

435 L Ambiance Drive K905, LONGBOAT KEY

2 Beds 4 Baths 2,820 SqFt Residential MLS® # A4566290

$4,200,000

↓ $300,000

435 L Ambiance Drive H802, LONGBOAT KEY

3 Beds 4 Baths 2,525 SqFt Residential MLS® # A4563757

$3,950,000

435 L Ambiance Drive J603, LONGBOAT KEY

2 Beds 4 Baths 2,820 SqFt Residential MLS® # A4571082

$3,545,000

↓ $205,000

1241 Gulf Of Mexico Drive 607, LONGBOAT KEY

3 Beds 4 Baths 2,965 SqFt Residential MLS® # A4568584

1 2 3

Next