Historic Old Town Conch homes, waterfront properties, and quiet Lower Keys neighborhoods.
At the southern terminus of US Highway 1 in Monroe County sits Key West, the southernmost city in the continental United States, preceded by the peaceful island chain of the Lower Keys (including Big Pine Key, Little Torch Key, Ramrod Key, Summerland Key, Cudjoe Key, and Sugarloaf Key).
Key West real estate is treasured for its architectural preservation in Historic Old Town, where 19th-century Bahamian-influenced Conch homes, eyebrow cottages, and Victorian estates sit behind white picket fences with lush tropical gardens, heated plunge pools, and wraparound verandas. Neighborhoods such as the Meadows, Bahama Village, Truman Annex, and the Casa Marina district offer walkable island living, while Sunset Key provides private island luxury accessible by ferry.
Just north of Key West in the Lower Keys, buyers seeking boating privacy, wider lots, and immediate access to the Great White Heron National Wildlife Refuge and Looe Key Reef find canal-front and open-water homes across Cudjoe Gardens, Venture Out, Summerland Key Cove (which also features a private community airstrip), and Big Pine Key.
Active South Florida Matrix IDX properties currently available in Key West & Lower Keys (Monroe County). All prices in USD.
MLS# K109130043 Beds • 3.5 Baths • 2,480 Sq Ft
Restored historic Conch residence in Key West & Lower Keys with heated pool, wraparound verandas, and off-street parking near Mallory Square.
Beyond its residential architecture and property values, Key West & Lower Keys offers residents year-round outdoor recreation, waterfront parks, shopping, and dining in Monroe County.
Explore over 3,000 historic wooden and coral-rock structures in Old Town, including Ernest Hemingway’s 1851 Spanish Colonial residence and President Harry S. Truman’s winter White House.
Swim and snorkel at Fort Zachary Taylor Historic State Park where the Gulf of Mexico meets the Atlantic Ocean, stroll the boardwalks at the Historic Seaport (Key West Bight Marina), and watch the daily Sunset Celebration at Mallory Square.
In the Lower Keys, dive the spectacular spur-and-groove coral formations of Looe Key Reef off Ramrod and Big Pine Keys, and explore the pine rocklands of the National Key Deer Refuge on Big Pine Key.
Take a seaplane or high-speed ferry 70 miles west of Key West to 19th-century Fort Jefferson in Dry Tortugas National Park, and enjoy year-round theater at the Red Barn Theatre, Waterfront Playhouse, and Studios of Key West.
The northernmost island of the Florida Keys, an hour south of Miami, with Ocean Reef, deep-water marinas, and reef access.
Known for offshore and backcountry fishing, Islamorada features oceanfront and bayfront homes across a chain of islands.
In the heart of the Middle Keys, offering deep-water canals, a local airport, marinas, and waterfront homes.
Whether you are searching for a primary residence, waterfront estate, or investment property in Key West & Lower Keys (Monroe County), our licensed South Florida associates are ready to assist you.