Neighborhoods

Living in Key West: Old Town is the island’s soul

Key West. No other city in the United States combines in just 5.5 square miles the cosmopolitan sophistication of Manhattan with the laid-back, live-and-let-live lifestyle of the historic Caribbean islands. Whether you’re considering a permanent Key West move or a second home to escape the mainland winters, you’ll soon find yourself wondering how you lived anywhere else.

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New Town

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.

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Midtown

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.

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Truman Annex

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.

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Casa Marina

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.

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The Meadows

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.

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Bahama Village

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.

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Old Town

Old Town is the neighborhood most people think of when they think “Key West.” Its homes are modest bungalows and magnificent mansions that live side-by-side along Fleming, Eaton, Margaret and Southard. Old Town is the neighborhood that defines paradise.

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