Living in Old Town, Key West

Where Old Town is, and how Zillow draws it

Old Town covers the western end of the island, the part settled first, around Duval Street, Mallory Square and the old harbor. Most of the Key West Historic District is here. Streets are narrow, lots are small, and houses sit close to the sidewalk.

Zillow splits this area into several pieces. Its list for Key West has Old Town as one neighborhood, and separately Truman Annex, Bahama Village, the Historic Seaport, Duvall Street, Upper Duvall and the White Street Gallery District. Many locals would call most of those Old Town too. When you read the Zillow figure here, it describes Zillow's narrower Old Town boundary, so a listing a block away may be counted under a different name.

The houses: frame, piers, tin roofs and porches

Old Town is mostly wood-frame houses, many from the late 1800s and early 1900s, set on piers above the ground with metal roofs, shutters and front porches. Some have been divided into condos or small multi-unit buildings. You also find newer infill and renovated cottages with pools tucked into small back yards.

Key West's housing overall has a median year built of 1968 in Census data, and Old Town is older than that median. A house here can be beautifully restored or quietly tired, and the difference is often under the floor and behind the walls.

• Termites and rot in sills, joists and porch framing
• Piers and foundation settling or shifting
• Wiring and plumbing from different decades in one house
• Roof attachment and the wind mitigation features insurers credit

Historic review changes what you can do

Exterior work inside the historic district goes through the Historic Architectural Review Commission. Windows, doors, siding, roofing material, fences and additions can all need approval, and the rules favor keeping original character. Interior work is less restricted, though it still needs regular building permits.

For buyers, this has two sides. The rules protect the look of the street, which supports values. They also add time and cost to a renovation, and some changes simply will not be approved. Before you write an offer on a house you plan to change, ask what approvals exist, look at the permit history and price the project with someone who has worked through the review before.

The Keys also limit how many new residential units can be added each year. That makes a second unit or a lot split hard to count on, so value the property as it stands.

Old Town prices next to the rest of Key West

Old Town's index fell 2.2% over the past year, the weakest one-year number in Zillow's Key West list. Over five years it is up 23.6%, close to the city's 24.8%. In plain terms, the area has been flat-to-soft lately after a strong run, which can give a buyer some room on price and repairs.

For comparison, among the other Zillow neighborhoods:

• Cheaper: New Town about $807,528, Bahama Village about $819,399, Midtown about $1,114,734, Upper Duvall about $1,214,765
• Similar or a bit higher: White Street Gallery District about $1,334,157, The Meadows about $1,354,802
• Higher: Duvall Street about $1,539,373, Truman Annex about $1,607,191, Historic Seaport about $1,717,231, Casa Marina about $2,014,505

Zillow's figure here covers all home types together. Old Town mixes small cottages, large restored houses and condos, so the typical value hides a very wide range.

Day-to-day life in the old part of the island

The main draw is walking. From much of Old Town you can reach the harbor, restaurants, galleries, groceries and the waterfront without a car. Many residents own a bike and use it more than anything else.

The costs are noise and parking. Blocks near Duval Street and the bars stay loud late, and cruise ship days bring crowds. A few streets away it can be quiet and residential. Walk the block at night and on a weekend before you buy. Off-street parking is scarce, so a house with a driveway or a parking space has a real advantage when you sell.

Insurance is the other big line item. Old frame houses in a low-lying area mean higher wind and flood quotes. Get quotes during the inspection period, ask for the elevation certificate, and check the FEMA flood zone for the exact address.

Is Old Town a good place to live for you

Old Town fits buyers who want the walkable historic core, like older houses and are ready for maintenance and historic rules. It fits less well for anyone who wants a garage, a large lot, new construction or a quiet street guaranteed. For a bit less money and more space, buyers often look at Midtown or New Town; for larger homes and lots, Casa Marina.

If you are a permanent resident, file for homestead after you close. The exemption is up to $51,411 off assessed value in 2026, with a 3% cap on future increases. A shortlist of Old Town homes with their flood zone and permit history is the most useful way to start.