The Meadows

Welcome to The Meadows

Just east of Old Town lies The Meadows, a peaceful residential neighborhood defined by its wide streets, lush gardens, and beautifully restored conch homes. Once a low-lying meadowland in the late 1800s, the area was gradually filled in and developed into one of Key West’s most desirable residential pockets.

Homes here often feature expansive porches, picket fences, and lush tropical landscaping—a tranquil reflection of classic island architecture. The Meadows’ convenient location near Bayview Park, White Street, and Truman Avenue makes it easy to enjoy all that Old Town offers while returning to a serene escape.

For those seeking a quiet, picturesque setting within biking distance of downtown, The Meadows embodies refined island living with historic flair.

Our Top Listings

Featured Properties

Handpicked homes and properties that represent the best of Key West living — luxury, location, and lifestyle.

For Sale
$9,950,000

1117 Duval Street, Key West, FL 33040
- 7 Beds
- 8 Baths
For Sale
$7,500,000

3750 Sunrise Lane, Key West, FL 33040
- 5 Beds
- 5 Baths
- 5,378 Sq.Ft.
For Sale
$7,495,000

616 Eaton Street, Key West, FL 33040
- 5 Beds
- 7 Baths
- 4,000 Sq.Ft.
For Sale
$4,450,000

1113 Stump Lane, Key West, FL 33040
- 4 Beds
- 5 Baths
- 2,985 Sq.Ft.
For Sale
$3,599,000

1501 Georgia Street, Key West, FL 33040
- 4 Beds
- 5 Baths
- 2,810 Sq.Ft.
For Sale
$3,025,000

17210 Angelfish Lane + 17220, Sugarloaf Key, FL 33042
- 3 Beds
- 3 Baths
- 2,288 Sq.Ft.
For Sale
$2,525,000

1427 Washington Street, Key West, FL 33040
- 4 Beds
- 3 Baths
- 2,051 Sq.Ft.
For Sale
$2,299,999

17210 Angelfish Lane, Sugarloaf Key, FL 33042
- 3 Beds
- 3 Baths
- 2,288 Sq.Ft.
For Sale
$2,299,500

1109 Stump Lane, Key West, FL 33040
- 3 Beds
- 4 Baths
- 1,724 Sq.Ft.
For Sale
$2,089,000

1706 Seminary Street, Key West, FL 33040
- 3 Beds
- 3 Baths
- 1,938 Sq.Ft.
For Sale
$1,949,000

3841 N Roosevelt Boulevard 315, Key West, FL 33040
- 2 Beds
- 3 Baths
- 1,357 Sq.Ft.
For Sale
$1,949,000

3841 N Roosevelt Boulevard 332, Key West, FL 33040
- 2 Beds
- 3 Baths
- 1,357 Sq.Ft.
For Sale
$1,899,000

1115 South Street, Key West, FL 33040
- 2 Beds
- 2 Baths
- 2,186 Sq.Ft.
For Sale
$1,899,000

1220 Georgia Street, Key West, FL 33040
- 4 Beds
- 3 Baths
- 1,602 Sq.Ft.
For Sale
$1,899,000

1229 5Th Street, Key West, FL 33040
- 6 Beds
- 3 Baths
- 3,197 Sq.Ft.
For Sale
$1,799,000

2101 Harris Avenue, Key West, FL 33040
- 3 Beds
- 3 Baths
- 1,456 Sq.Ft.
For Sale
$1,599,000

1200-1206 White Street, Key West, FL 33040
- 3 Baths
- 3,380 Sq.Ft.
For Sale
$1,395,000

34 Key Haven Road, Key Haven, FL 33040
- 4 Beds
- 2 Baths
- 1,743 Sq.Ft.
Active Under Contract
$1,199,000

1626 Von Phister Street, Key West, FL 33040
- 4 Beds
- 2 Baths
- 1,599 Sq.Ft.
For Sale
$1,175,000

1317 Newton Street, Key West, FL 33040
- 2 Beds
- 3 Baths
- 1,386 Sq.Ft.
For Sale
$1,050,000

1200+1202 White Street, Key West, FL 33040
- 1 Bath
- 2,061 Sq.Ft.
For Sale
$999,000

3841 N Roosevelt Boulevard 222, Key West, FL 33040
- 3 Beds
- 3 Baths
- 1,586 Sq.Ft.
For Sale
$899,000

209 Shore Avenue, Big Coppitt, FL 33040
- 3 Beds
- 2 Baths
- 1,548 Sq.Ft.
For Sale
$899,000

3841 N Roosevelt Boulevard 213, Key West, FL 33040
- 2 Beds
- 3 Baths
- 1,357 Sq.Ft.
For Sale

$825,000

3705 Eagle Avenue, Key West, FL 33040
For Sale
$825,000

3711 Eagle Avenue, Key West, FL 33040
- 2 Beds
- 2 Baths
- 1,464 Sq.Ft.
For Sale
$780,000

25 Kingfisher Lane, Key West, FL 33040
- 2 Beds
- 3 Baths
- 900 Sq.Ft.
For Sale

$725,000

17220 Angelfish Lane, Sugarloaf Key, FL 33042
For Sale
$599,000

816 South Street 4, Key West, FL 33040
- 1 Bed
- 1 Bath
- 640 Sq.Ft.
For Sale
$499,000

1202 White Street, Key West, FL 33040
- 1 Bath
- 892.36 Sq.Ft.
For Sale
$344,000

3312 Northside Drive 205, Key West, FL 33040
- 1 Bed
- 1 Bath
- 528 Sq.Ft.
For Lease
$5,000/mo

101 Front Street 4, Key West, FL 33040
- 2 Beds
- 3 Baths
- 1,216 Sq.Ft.