Key West Real Estate & Home Prices

Life in Key West 

The beautiful island of Key West is the southernmost point in the contiguous United States and is located a scant 95 miles north of Havana, Cuba. These days its subtropical climate lures tourists and sun seekers year round, but its storied history of pirates and playwrights adds to the glamour of this little slice of Caribbean paradise.

Key West is small in size (only 4 miles long and 1 mile wide), but it packs a lot into a tiny space. Known for its fresh seafood — conch fritters are a local specialty — beautiful beaches, and raucous nightlife, it’s every beach bum’s dream. The entire town is walkable. Duval Street, its main road, is the central business district and a popular tourist destination. It is also the only street where you can walk from the Gulf of Mexico to the Atlantic Ocean in just 14 blocks. There is only one golf course on Key West, but it was designed as a “Caribbean style” course by legendary golf architect Rees Jones, with the infamous “Mangrove Hole,” played entirely over a field of intertwined tropical mangrove roots.

Naval Air Station Key West is located just outside town and it’s a year-round training ground for naval aviators. Training here focuses on air combat and aircraft carrier landing skills.

Key West history

As with all of Florida, Key West has changed hands many times throughout recorded history. The Calusa tribe were the last natives known to inhabit the area and they were forcibly transferred to Havana in 1763 when Great Britain wrested the island from the Spanish. From that time until the US gained control in 1821, there were no known permanent inhabitants in all of the Florida Keys. Cubans and Bahamians were regular visitors, fishing, cutting hardwood timber, and salvaging shipwrecks. Pirates, privateers, and smugglers frequented the Keys as the deep channels, coral reefs, and protected bays offered places to hide or seek shelter from storms at sea.

Throughout the Civil War the island remained in Union hands because of the naval base, even though Florida had seceded and joined the Confederacy. Fort Zachary Taylor was constructed during the war, and today it is a National Historical Landmark that contains the largest collection of Civil War cannons discovered at a single location.

A number of hurricanes have damaged Key West, and despite stringent building codes, the island remains vulnerable to the whims of Mother Nature. The last hurricane to cause significant damage was Hurricane Irma in 2017. Realm’s data analysis shows that 77% of homes are within a designated flood zone. Potential homeowners should take note — if your home does sit in a flood zone, it’s critical that you get the proper insurance to protect your home. 

Key West home styles and architecture

The Old Town Historic District is Key West’s main tourist attraction, with structures dating from 1862–1912. Classic bungalows and guest mansions can be found here and in the adjacent Bahama Village neighborhood. This area also contains the Hemingway House, residence of Ernest Hemingway from 1931-1939, and Harry S. Truman’s Little White House, a summer residence during his presidency. Playwright Tennessee Williams was also a resident of Key West. He was purported to have written A Streetcar Named Desire at his bungalow in the unfashionable New Town neighborhood.

Homes on the island bear distinctive hallmarks uniquely suited to the climate. Light pastel, seaside, and neutral colors adorn the exteriors, warding off the summer heat. Vintage cottages with ornate latticework, wrap-around verandas, and decorative shutters are the most common home style. Conch houses, influenced by Bahamian immigrants, are also prevalent. These rectangular structures are usually one or two floors and feature full-length porches on both floors. In contrast to the cottage style, Conch homes are simpler, without excess ornamentation.

As you might expect in such a warm climate, swimming pools are the most popular amenity in the Key West housing market. According to Realm’s data analysis, they were mentioned in 442 recent listings. Other popular features include decks (mentioned in 186 listings), landscaping (173 mentions) and fencing (mentioned in 145 listings). Also popular in the Key West housing market: HVAC work, which was mentioned in 144 recent real estate listings. 

Data analysis done by Realm shows that most Key West homes were built in 1958. That means that these homes are sturdy and have withstood many hurricane seasons. If you are thinking about purchasing a home here, it is wise to have an experienced inspector perform a thorough investigation. Finding evidence of flooding, substantial foundation damage or displacement, and pest intrusion before you buy could save thousands of dollars down the road.

Frequently asked questions about Key West real estate 

Is it expensive to live in Key West?

Key West is the second most expensive place to live in Florida. Keep in mind that it’s an island and there are extra costs inherent with island-living. Groceries, gasoline, household goods – everything costs a little more than you would pay on the mainland. On top of that, Key West has a small footprint with no room to expand, so competition for housing can be intense. And when competition is high, you can also expect to see higher home prices. A nearby alternative is Stock Island, which is becoming a sort-of suburb of Key West.

Is Key West a good place to retire?

If you appreciate an active outdoor lifestyle, Key West is a great place to live. Golf, tennis, swimming, paddle boarding, kayaking, hiking, beach walking – everything is accessible within minutes from home. Buying a home, especially one with an attached rental unit, is a sound investment as there is high demand for long-term rentals. Key West offers residents a delightful mix of urban/suburban living with plenty of social interaction but quiet residential neighborhoods.

What is the average cost of a home in Key West?

As of October 2021, the median home price in Key West was $834,034. Home values in Key West have risen 15.8% during the past year.