Best Neighborhoods to Buy a Home in Key West

How to read these neighborhood numbers

Zillow's neighborhood index covers all home types together, so an area full of condos looks cheaper than one full of detached houses even if the streets are similar. Zillow also divides the historic part of the island more finely than locals do. Several of the names below, such as Truman Annex, Bahama Village and Upper Duvall, are areas many people simply call Old Town. Zillow spells one of them Duvall Street; the street itself is Duval.

Key West is small, about 25,720 residents, with a median year built of 1968 for its housing. The age of a specific house and its elevation often matter more than the neighborhood name.

Under the city typical: New Town and Bahama Village

• New Town, about $807,528 (1 year -1.7%, 5 years 25.7%). The eastern half of the island, with mid-century concrete block houses, condo complexes, shopping centers and the airport. More parking and larger lots than the historic core.
• Bahama Village, about $819,399 (1 year 0.6%, 5 years 20.0%). A small historic neighborhood on the west side of Old Town, with older frame houses and narrow streets, close to the waterfront.

These two are the entry points for buyers who want a house rather than a condo. Bahama Village had the smallest five-year gain on the list apart from Duvall Street, while New Town's long-run gain beat the city's 24.8%. The housing could hardly be more different, so most buyers rule one out quickly once they see both.

The middle band: $1.1 to $1.4 million

• Midtown, about $1,114,734 (1 year 2.8%, 5 years 28.7%). Between New Town and Old Town in the center of the island. Its 2.8% one-year gain is the second best on the list.
• Upper Duvall, about $1,214,765 (1 year 1.8%, 5 years 23.3%). The southern end of Duval toward the Atlantic, generally calmer than the bar blocks.
• Old Town, about $1,259,886 (1 year -2.2%, 5 years 23.6%). The historic core in Zillow's narrower boundary, and the weakest one-year number on the list.
• White Street Gallery District, about $1,334,157 (1 year 0.4%, 5 years 29.3%). Along White Street, with galleries and residential blocks.
• The Meadows, about $1,354,802 (1 year 0.1%, 5 years 31.5%). A mostly residential area east of the historic core.

This band is where most single-family buying happens. The typical Key West house is about $1,149,359, right in the middle of it.

The top band: $1.5 million and up

• Duvall Street, about $1,539,373 (1 year 1.6%, 5 years 1.4%). Properties on and around the main commercial street. The five-year figure is almost flat, far below every other area, which suggests a small and unusual mix of sales.
• Truman Annex, about $1,607,191 (1 year 1.6%, 5 years 26.1%). Former Navy land on the west side, home to the Little White House, with newer homes and condos built after the Navy left.
• Historic Seaport, about $1,717,231 (1 year 3.6%, 5 years 41.7%). The Key West Bight harbor area with marinas and restaurants. Strongest gains on both time frames.
• Casa Marina, about $2,014,505 (1 year 1.1%, 5 years 35.7%). Larger houses and lots on the Atlantic side.

In this band, two homes in the same neighborhood can differ by a million dollars depending on lot, pool, parking and elevation.

What to check by type of neighborhood

• Historic areas (Old Town, Bahama Village, Upper Duvall, White Street): exterior changes go through historic review, and frame houses need termite, rot and pier inspections.
• Mid-century areas (New Town, Midtown, The Meadows): slab elevation, original plumbing, roof age and opening protection.
• Waterfront and harbor areas (Historic Seaport, Truman Annex, Casa Marina): coastal flood zones, elevation certificates and condo association insurance and reserves.

Everywhere on the island, get insurance quotes during the inspection period. A permanent resident who files homestead gets up to $51,411 off assessed value in 2026 and the 3% cap, which changes the yearly cost a lot at these prices.

Condo or house changes which neighborhoods are in reach

The citywide split is wide. Zillow's typical Key West condo is about $705,769 and the typical single-family house about $1,149,359, a gap of roughly $443,600. That means a condo buyer with $800,000 can shop in most of the neighborhoods above, while a house buyer with the same budget is mostly limited to New Town and Bahama Village, and often to smaller or older homes there.

Bedroom count moves the line again. A typical 2-bedroom is about $838,599, a 3-bedroom about $1,238,154 and a 4-bedroom about $1,818,997. Families who need three bedrooms are usually shopping in the middle band or in New Town, and four bedrooms pushes most buyers toward Casa Marina, The Meadows or the larger lots in New Town. Decide on home type and bedrooms before you fall for a neighborhood.

When none of them fits the budget

Buyers priced out of the island usually look up the chain. Zillow's typical value is about $667,304 on Stock Island, about $752,866 on Big Pine Key and about $779,161 on Big Coppitt Key. Marathon is about $832,447. Key Largo, Summerland Key and Islamorada cost more than Key West's typical home. Pick your price band first, then two or three neighborhoods inside it, and a shortlist of homes from those areas is the natural next step.