The Spottswood Team
Address
1205 TRUMAN AVE
KEY WEST FL 33040
The heart and soul of the island, Old Town is where Key West began. Stretching from White Street to the Gulf, this historic district showcases the island’s architectural heritage—Victorian mansions, cigar-makers’ cottages, and Bahamian-style conch houses dating back to the mid-1800s. Once a bustling port for wreckers, fishermen, and traders, Old Town flourished as a maritime hub and cultural crossroads. Today, it’s a lively blend of history and modern-day excitement. Duval Street serves as the island’s main thoroughfare, home to art galleries, award-winning restaurants, and world-famous watering holes once frequented by Ernest Hemingway and Tennessee Williams.
Residents enjoy being steps away from the Historic Seaport, Mallory Square’s sunset celebrations, and an array of shops and cultural landmarks. Old Town captures the essence of classic Key West living—vibrant, walkable, and endlessly charming.
Our Top Listings
Handpicked homes and properties that represent the best of Key West living — luxury, location, and lifestyle.
For Sale
$11,500,000
412 Frances Street, Key West, FL 33040
For Sale
$7,495,000
616 Eaton Street, Key West, FL 33040
For Sale
$5,595,000
1006-1008 Fleming Street, Key West, FL 33040
For Sale
$4,650,000
1523 Patricia Street, Key West, FL 33040
For Sale
$4,595,000
1113 Stump Lane, Key West, FL 33040
Active Under Contract
$3,599,000
1020 Southard Street, Key West, FL 33040
For Sale
$3,595,000
33 Cypress Avenue, Key Haven, FL 33040
For Sale
$2,400,000
1109 Stump Lane, Key West, FL 33040
$2,299,999
17210 Angelfish Lane, Sugarloaf Key, FL 33042
For Sale
$2,299,999
17210 Angelfish Lane, Sugarloaf Key, FL 33042
For Sale
$2,249,000
1706 Seminary Street, Key West, FL 33040
For Sale
$1,995,000
1229 5Th Street, Key West, FL 33040
For Sale
$1,949,000
3841 N Roosevelt Boulevard Unit: 315, Key West, FL 33040
For Sale
$1,949,000
3841 N Roosevelt Boulevard Unit: 332, Key West, FL 33040
For Sale
$1,800,000
408 William Street, Key West, FL 33040
$1,799,000
17213 Starfish Lane, Sugarloaf Key, FL 33042
For Sale
$1,799,000
17213 Starfish Lane, Sugarloaf Key, FL 33042
For Sale
$1,399,900
1317 Newton Street, Key West, FL 33040
For Sale
$1,325,000
247 Golf Club Drive, Key West, FL 33040
For Sale
$999,000
3841 N Roosevelt Boulevard Unit: 222, Key West, FL 33040
For Sale
$995,000
701 Spanish Main Drive Unit: 221, Cudjoe Key, FL 33042
For Sale
$899,000
3841 N Roosevelt Boulevard Unit: 213, Key West, FL 33040
For Sale
$859,500
3705 Eagle Avenue, Key West, FL 33040
For Sale
$859,500
3711 Eagle Avenue, Key West, FL 33040
For Sale
$825,000
1206 White Street, Key West, FL 33040
For Sale
$799,999
1200 White Street, Key West, FL 33040
For Sale
$735,000
1202 White Street, Key West, FL 33040
For Sale
$725,000
17220 Angelfish Lane, Sugarloaf Key, FL 33042
$725,000
17220 Angelfish Lane, Sugarloaf Key, FL 33042
$725,000
17230 Angelfish Lane, Sugarloaf Key, FL 33042
For Sale
$725,000
17230 Angelfish Lane, Sugarloaf Key, FL 33042
For Sale
$665,000
1124 Catherine Street Unit: 202, Key West, FL 33040
For Sale
$600,000
701 Spanish Main Drive Unit: 384, Cudjoe Key, FL 33042
For Sale
$584,000
3930 S 3930 Roosevelt Boulevard Unit: N302, Key West, FL 33040
For Sale
$550,000
3930 S Roosevelt Boulevard Unit: E104, Key West, FL 33040
For Sale
$465,000
1124 Catherine Street Unit: 201, Key West, FL 33040
For Sale
$455,000
31129 Avenue G, Big Pine Key, FL 33043
For Sale
$300,000
5555 College Road Unit: 9 (Sailfish), Key West, FL 33040
The Spottswood Team is one of the most accomplished real estate groups in the Florida Keys, guiding buyers and sellers through 1,000+ successful transactions across Key West and beyond. With over $1 billion in closed sales volume, TST continues to set the standard for excellence in island real estate.
ADDRESS 1205 TRUMAN AVE KEY WEST FL 33040
ADDRESS 1205 TRUMAN AVE KEY WEST FL 33040