The Neighborhoods of Key West
Though the island of Key West is a tiny five square miles, each of its primary neighborhoods displays its own individual charm. From the classic Conch cottages and soaring Victorians of Old Town to the mid-century modern homes and Mediterranean mansions in the Casa Marina District, Key West real estate offers exceptional choices for home buyers. And because growth and new development are limited in Key West, homes of all styles are in demand.
Key West’s oldest and most historic neighborhoods include Old Town, The Meadows, Bahama Village and the Casa Marina District. Truman Annex, once the home of military personnel, is just blocks from Old Town. Old Town itself — at least for locals — includes Old Town South-of-Truman and Old Town North-of-Truman.
There’s also Midtown — East and West — and New Town, where you’ll find larger lots and what many would describe as luxurious “traditional Florida” construction.
Just across the harbor from Mallory Square is Sunset Key, a much newer, exclusive enclave of homes accessible only by a quick shuttle boat ride from the dock. With their eclectic pe
rsonalities, each neighborhood offers easy access to the best of Key West — from dining and theater to water sports and amazing sunsets.
And, if you can’t find that perfect home in Key West, Brenda Donnelly and her team will take you “up the Keys,” where you’ll find new builds and classic Florida, canal-side homes with direct access to the Atlantic and the Gulf of Mexico.
The heart, and some would say the soul, of Key West is Old Town. Originally the city’s center, Old Town is today the central location for Key West’s historic district and tourist destinations. Old Town’s Duval Street, which stretches from the Gulf of Mexico to the Atlantic Ocean is the main artery in Key West. Intersected by Truman Avenue, Duval Street provides the backbone for Key West’s historic homes, seaport and cultural centers.
Read more about Old Town.
In the 1990s, a private developer transformed 100 acres of Truman Annex into a secluded enclave of single family homes, condominiums and town houses. The beautifully designed neighborhood combines new construction and renovated officers’ housing.
Read more about Truman Annex.
Bahama Village is a small, culturally significant neighborhood within the boundaries of Old Town. Bahama Village has retained its identity and independence from its neighbors in Truman Annex and Old Town.
Read more about Bahama Village.
Perhaps the best residential area in Old Town, The Meadows is the first choice for Key West residents who want the amenities and historic architecture of Old Town, but with slightly larger lots, wider streets and quieter residential living.
Read more about The Meadows.
The Casa Marina District is a showcase for Mid-Century modern architecture, ranging from clean-lined bungalows to private enclaves and statuesque mansions. Its wide, tree-lined boulevards offer perfect space to showcase royal palms and poincianas.
Read more about the Casa Marina District.
The Midtown neighborhoods, built in the middle 20th century, combine Mid-Century modern styles with Old Town’s Conch cottages. These are the neighborhoods Key West locals call home.
Read more about Midtown.
New Town feels more like classic Florida than any other Key West neighborhood. Developed in the mid-20th century as a residential subdivision, New Town boasts large lots, wide streets and rambling ranches and bungalows — and optimal room for outdoor living.
Read more about New Town.