Key West homes for sale include historic Conch cottages in Old Town, homes in Casa Marina and Truman Annex, and more modest houses and condos in New Town. It's one of the most expensive markets in Florida, short-term vacation rentals are tightly limited, and the island sits right in the path of Atlantic hurricanes, so insurance is a major cost. Rui Cunha's office is in Deerfield Beach, and he works with buyers across Florida, including the Keys.
What it's like to live in Key West
Key West is a small island city at the end of the Florida Keys, in Monroe County. Florida's Office of Economic and Demographic Research estimated its population at 26,524 as of April 2025, out of 84,705 in all of Monroe County (Florida EDR). Land is limited, and so is new construction: the city's Building Permit Allocation System regulates new homes so that the 24-hour hurricane evacuation time for permanent residents can be maintained (City of Key West).
Neighborhoods
A local guide describes the island's main areas (Old Town Trolley Tours):
- Old Town. The historic heart of the island, with turn-of-the-century architecture and landmarks.
- Bahama Village. A neighborhood with Bahamian roots and colorful "shotgun" houses.
- Truman Annex. A historic area where President Truman spent his winters.
- Casa Marina. A residential area with tree-lined streets, named after Henry Flagler's 1920 hotel.
- New Town. The mid-20th-century part of the island, where much of local daily life, shopping and recreation happens.
Historic district rules. Exterior work on homes in the historic district goes through the city's Historic Architectural Review Commission (HARC) process (City of Key West). If you plan to renovate, budget time for that review.
Key West market snapshot: high prices
According to Momentum Research, using Florida Keys MLS records, 309 homes closed in Key West's 33040 ZIP code in the 12 months ending September 20, 2026, at a median of about $908,000, down about 4.3% from the prior year (Momentum). For context, Florida's statewide single-family median was $415,000 in August 2026 (Florida Realtors).
The 33040 ZIP code also covers some nearby keys outside the city, and the figure mixes condos with single-family homes. Old Town houses can cost much more. Ask Rui for a current comparison of recent sales for what you're actually considering.
Vacation rentals: read this before you buy
Many buyers picture renting the house to tourists when they aren't using it. In Key West, that's restricted:
- A license is required for rentals of less than 30 days. The city treats any unit rented for less than 30 days or one calendar month as transient lodging (City of Key West).
- New transient licenses have been capped since 2002 (The Blue Paper, 2019). Existing licenses are tied to specific properties and can only move to another property through a city review; for example, the Planning Board heard a request in October 2025 to transfer one license between two addresses (City of Key West Planning Board).
In practice, unless a property already holds a transient license, plan on monthly or longer rentals. Confirm the license status and zoning of any property before you count on rental income, and be wary of listings that promise nightly rentals without proof.
Practical notes: hurricanes, flood and insurance
Storm history. According to the National Hurricane Center, Hurricane Irma made landfall near Cudjoe Key in the Lower Keys in September 2017 as a Category 4 hurricane. Inundation reached 2 to 4 feet above ground from Cudjoe Key west to Key West, and in the Middle and Lower Keys most homes were badly damaged or destroyed (NHC, Irma report). Even storms that hit the Gulf Coast affect the Keys: in 2024, Helene and Milton each brought 1 to 2 feet of storm surge to the Florida Keys (NHC, Helene; NHC, Milton).
Flood insurance. When FEMA's newer flood pricing (Risk Rating 2.0) arrived in 2022, a local advocacy group estimated eventual increases averaging $3,200 a year for Monroe County policies, while FEMA's own projections showed much smaller yearly increases for most properties (Key West Citizen via InsuranceNewsNet, April 2022). Either way, an elevation certificate and a real quote are essential.
Before you make an offer:
- Check the flood zone and the home's elevation, and ask about damage from past storms and what was repaired.
- Get real homeowners, windstorm and flood quotes. Florida's Office of Insurance Regulation puts the statewide average homeowners premium at about $3,736 a year (Florida Realtors, September 2026); an older house on a small island can cost more.
- If you'll insure through Citizens, flood coverage is becoming mandatory as that rule phases in through 2027 (News4JAX).
Condos. Buildings of three or more stories need milestone inspections and a Structural Integrity Reserve Study with funded reserves (SB 154, 2023; Rimkus). Ask for the reserve study, budget, rental rules and assessment history.
Homestead. If the home will be your primary residence, ask a CPA about Florida's homestead exemption. Second homes and non-residents don't qualify.
Schools and getting around
Key West is served by the Monroe County School District; confirm the assigned schools for any address and check grades with the Florida Department of Education. The island is compact. The only road to the mainland is the Overseas Highway (US 1), which matters when evacuation orders come.
Working with Rui in Key West
Rui's office is in Deerfield Beach, and he helps clients across Florida. He has worked in Florida real estate since 2003, as a mortgage broker, a broker and a licensed General Contractor, which helps when you're judging an older Conch house, a storm repair or renovation plans that need historic review. He can help you buy a home, look into an ITIN mortgage or buy as an international buyer. Use the mortgage calculator with insurance included, and compare with Naples.
FAQ
Can I rent my Key West home on Airbnb?
Only if the property holds a transient rental license. Key West requires one for rentals of less than 30 days, and new licenses have been capped since 2002, so most homes can only be rented monthly or longer. Check the license status before you buy.
How expensive is Key West?
Momentum Research, using Florida Keys MLS records, put the median at about $908,000 for the 33040 ZIP code in the 12 months ending September 2026 (all home types, so not directly comparable with the $415,000 statewide single-family median, but far above it).
Is flood insurance expensive in Key West?
It can be. Premiums depend on the home's elevation and flood zone. Get an elevation certificate and real quotes before you sign.
Can I buy in Key West without a Social Security number?
Many buyers use an ITIN mortgage, subject to lender approval. See our ITIN mortgage guide or contact Rui.
Talk to Rui
Dreaming of Key West? Ask Rui to check rental rules, flood zone and recent sales before you fall for a house.