Is Key West a Good Place to Retire?

How many retirees already live here

Census data shows 21.6% of Key West residents are 65 or older, and the median age is 46.1. That is older than the United States overall, but younger than many Florida retirement towns. Key West keeps a working-age population because tourism, the Navy and local government employ a lot of people.

Seasonal homes account for 14.8% of units. Many retirees here are part-time, spending winter on the island and summer somewhere cooler. If you plan to live here twelve months a year, expect some neighbors to be gone for half of it, and expect August and September to be hot, humid and quiet.

For retirees, that mix has an upside. You are not living in a town built only around retirement, and there are things to do that do not involve a clubhouse.

What the homes retirees buy actually cost

Most retirees I talk with want two bedrooms, low maintenance and no stairs. On Zillow's numbers, the typical Key West condo is worth about $705,769 and was flat over the past year. A typical single-family house is about $1,149,359. The whole-market index rose 24.8% over five years and 0.3% over the last year.

• 1 bedroom: about $605,940
• 2 bedrooms: about $838,599
• 3 bedrooms: about $1,238,154

A common downsizing plan does not work here. Selling a $500,000 house somewhere else and buying smaller in Key West usually means adding money, since the lower third of the market tops out near $638,656. Nearby Stock Island ($667,304) and Big Pine Key ($752,866) cost somewhat less. Marathon, in the Middle Keys, sits near $832,447 and has its own services.

Healthcare when you live on an island

Lower Keys Medical Center on Stock Island, right next to Key West, is the area's hospital. Its governing board has been searching for a new operator because the current lease runs out in 2029, so follow that process if hospital access is central to your plans.

Routine care, primary doctors and pharmacies are local. More complex procedures and many specialists mean a trip to the Miami area, which is a long drive up US 1. Before you buy, check three things: that your Medicare plan or supplement works with providers in Monroe County, how far your specialists would be, and what you would do in an emergency during an evacuation.

Retirees with stable health tend to do well here. Retirees managing several conditions often find the travel tiring after a few years.

55+ living without many 55+ communities

Key West is a small, built-out island, so most retirees buy in ordinary condo complexes and neighborhoods rather than age-restricted developments. If you see a property marketed as 55+, the federal Housing for Older Persons Act requires at least 80% of occupied units to have one resident 55 or older, and the association must have published age rules.

Across Florida, 55+ housing comes as manufactured-home communities (some on leased land, some on owned lots), condo associations and single-family active-adult neighborhoods. In the Keys, the condo route is the most common for retirees who want lock-and-leave living. Ask for the association's rules on age, pets and guests in writing.

Many condo buildings here are low-rise and older. Because the median year built in Key West is 1968, ask about the roof, reserves and any planned special assessments before you fall for the view.

Homestead, the 3% cap and fixed-income budgeting

If Key West is your permanent home, the homestead exemption cuts up to $51,411 from assessed value in 2026, and the Save Our Homes cap holds assessment growth to 3% or CPI each year. That cap is the best protection a retiree has against rising tax bills. A part-time resident who keeps a permanent home elsewhere does not get it.

Property tax is only one of the fixed costs. On a fixed income, add up the full monthly picture before you choose a home: association fees, homeowners and flood insurance, utilities and a reserve for repairs. In older associations, a special assessment can land with little warning. Insurance premiums can also move year to year, and they are a large line item on a low-lying island.

This isn't legal or tax advice. For any retiree splitting time between two states, residency rules deserve a conversation with a tax professional.

Hurricane prep for retirees

The Keys evacuate early and widely. Retirees should plan where they will go, who drives, how medications and records travel, and how long they can stay away. A ground-floor condo in a flood zone adds risk; an elevated unit or house reduces it.

When you compare homes, ask for the wind mitigation report, the roof age, impact windows or shutters, and the flood zone. Your hurricane deductible will be a percentage of dwelling coverage and applies once each calendar year, so on a fixed income keep cash set aside equal to that deductible.

Key West fits retirees who want a small walkable town, can absorb high prices and premiums, and are comfortable leaving when told. It fits less well for anyone who needs frequent specialist care or a very predictable budget. If it sounds right, a shortlist of 2-bedroom options with insurance estimates is the useful next step.