Which Key West Neighborhood Is Right for You?

Choosing the Right Block of a Small Island

Key West is a small island, but it contains a surprising range of neighborhoods, each with its own character, architecture, price profile, and ideal buyer. Choosing the right one is as important as choosing the right house. The same property in two different neighborhoods can offer entirely different lifestyles and investment outcomes.

What follows is a grounded comparison of the neighborhoods that make up the Key West market, based on decades of selling in each of them.

Old Town

Old Town is the heart of Key West — the historic district, the Conch houses, the walkable streets, the galleries and restaurants. It is what most people picture when they think of Key West, and it is the neighborhood that drives the premium market.

The architecture is predominantly historic Conch, with some Victorian and Bahamian cottage forms. Properties here are protected by HARC, which preserves the character that makes the area desirable. Price points are the highest on the island, reflecting the scarcity and the architectural significance.

Old Town is right for buyers who want walkability, historic character, and the cultural energy of the island's core. The trade-off is density and visitor traffic — Old Town is a destination neighborhood.

Casa Marina

Casa Marina is the area to the east of Old Town, named for the historic Casa Marina resort. It features larger lots, wider streets, and a mix of historic and newer homes. The architecture ranges from grand estate properties to more modest Conch houses, and the neighborhood has a quieter, more residential feel while remaining walkable.

Casa Marina is right for buyers who want historic character and walkability with more space and privacy than Old Town typically offers. It is popular with full-time residents and affluent second-home owners.

The Meadows

The Meadows is a residential neighborhood just east of the historic core, known for its tree-canopied streets and a mix of restored Conch houses and newer construction. It is quieter than Old Town but close to it — a short walk or bike ride to Duval and the harbor.

The Meadows has become increasingly desirable as buyers seek the Old Town feel with less tourist traffic. Prices have risen accordingly, though the neighborhood can still offer relative value compared to the heart of Old Town.

Truman Annex

Truman Annex is a planned community on the western end of the island, adjacent to Fort Zachary Taylor. It features newer construction — townhomes and single-family homes — in a gated, landscaped setting with pools and common areas. The architecture is Conch Revival, designed to echo the historic forms.

Truman Annex is right for buyers who want new construction, security, and resort-style amenities in a walkable location near Old Town. It is popular with second-home owners who want a lock-and-leave property. The trade-off is that the homes are not historic, and the community has a more managed feel.

Midtown

Midtown is the area between Old Town and New Town. It offers a mix of Conch houses, mid-century homes, and newer construction, at price points generally below Old Town and Casa Marina. The neighborhood is residential and practical, with good proximity to the historic core.

Midtown is right for buyers who want to be close to Old Town at a more accessible price point. Some of the best value plays on the island are in Midtown, where renovation projects can create significant equity.

New Town

New Town is the eastern portion of the island, developed primarily from the 1960s onward. It features newer construction, wider streets, larger lots in some areas, and a more suburban character. Price points are generally lower than the historic neighborhoods.

New Town is right for buyers who prioritize space, modern construction, and value over historic character and walkability. It is popular with full-time residents and families.

Sunset Key

Sunset Key is a private island community accessible by a short ferry ride from the Key West Bight. It features luxury homes on large lots with ocean and sunset views, a private beach, and resort-level services. The community is small and exclusive.

Sunset Key is right for buyers who want maximum privacy, luxury, and waterfront living with managed services. It is among the most expensive communities on the island. The trade-off is the ferry dependency — for the right buyer, that isolation is the point.

Key West Golf Club

The Key West Golf Club community surrounds the island's only golf course, in the eastern part of the island. It features newer homes and townhomes, many with golf course or water views, in a suburban, resort-style setting.

The Golf Club is right for buyers who want golf access, newer construction, and a community setting. It is popular with retirees and second-home owners who want recreational amenities.

Key Haven

Key Haven is a community just off Key West, connected by a short bridge, featuring waterfront homes with docks on deep-water canals. It is a boating-oriented community with a more residential, less touristy character.

Key Haven is right for buyers who want waterfront living with dock access and a quieter community, while remaining minutes from Key West. It is popular with boaters.

The Lower Keys

The Lower Keys — from Stock Island west through Big Coppitt, Sugarloaf, and Cudjoe — offer waterfront and near-waterfront properties at generally lower price points than Key West. The character is more rural, more boating-focused, and less developed.

The Lower Keys are right for buyers who want space, water access, and value, and who are willing to be 15 to 45 minutes from Key West.

How to Choose

The right neighborhood depends on how you plan to use the property, what you value, and your budget. Will this be a primary residence or a second home? Do I want to walk to dinner, or do I want privacy? Do I need a dock? Do I want historic character or modern construction? Is this an investment, a lifestyle purchase, or both?

There is no wrong answer. There is only the answer that fits your life.

Frequently Asked Questions

What is the most expensive neighborhood in Key West?

Old Town and Casa Marina command the highest prices, followed by Sunset Key and waterfront communities like Key Haven. The premium reflects historic character, scarcity, and location.

Which Key West neighborhood is best for second-home owners?

Truman Annex and Sunset Key are popular with second-home owners for their managed environments and lock-and-leave convenience. Old Town and Casa Marina appeal to owners who want the full historic Key West experience.

Where can I find the best value in Key West?

Midtown and New Town offer the most accessible price points while remaining on the island. Renovation projects in Midtown can create significant equity for buyers willing to do the work.

Which neighborhood is best for boaters?

Key Haven and the Lower Keys offer the best dock and water access for boaters. Some Old Town and Casa Marina properties have dock access, but it is scarce and expensive.

Is Truman Annex a good investment?

Truman Annex has shown strong value retention due to its managed environment, amenities, and location. It appeals to second-home buyers, which supports demand.

Can I walk everywhere from Old Town?

Yes. Old Town is the most walkable neighborhood on the island. This walkability is a primary driver of its premium.

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Damian Vantriglia is a born-and-raised Key West REALTOR® with Berkshire Hathaway HomeServices Keys Real Estate. Schedule a consultation to find the neighborhood that fits your life.