Key West and the Florida Keys Housing Market Report, August 2026

By Ryan and Megan Winslow, broker owners of Winslow Homes. Updated October 4, 2026.

The median sale price in Key West was $1,049,306 in the three months ending August 2026, up 13.7% from a year earlier, according to Redfin. Homes took a median of 141 days to sell, 10 days longer than last year. Across Monroe County, which covers the whole Florida Keys, the median sale price was $971,748, up 1.5%. The Keys are a slow, high-priced market where patience pays on both sides.

Redfin gives Key West a Compete Score of 5 out of 100, which signals low competition. With 99 sales in the Redfin window, a few high-end closings move the median a lot. The Zillow index, which covers all homes, slipped 0.7%, so read the 13.7% gain as a shift in what sold more than a jump in every home's value.

What this means for buyers

A sale-to-list ratio of 95.6% means the typical Key West home closed about 4.4% under its final list price. On a $1,050,000 home, that gap is roughly $46,000 of negotiating room. Across Monroe County the ratio was 94.6%. Only 5.2% of Key West homes sold above list.

Zillow shows 272 homes for sale in Key West and a median of 104 days to pending. Homes that sit give you leverage. Ask for repair credits, closing cost help or a rate buydown along with price, and get insurance quotes early, because insurance often decides whether a Keys home fits your budget.

Ryan and Megan are Mortgage Bankers with The Federal Savings Bank. They build payment estimates that include taxes, wind coverage and flood coverage, so the number you see matches the number you pay. Second-home and investment loans carry different terms than a primary residence loan, so tell them how you plan to use the home.

What this means for sellers

Price per square foot rose 4.1% to $866 in Key West and 3.0% to $750 across Monroe County. Well kept homes are holding value. A median of 141 days on market means you need a plan for a long listing period, including insurance, storm preparation and carrying costs.

Price to recent closed sales, not to list prices. Redfin shows a home on 16th Terrace that sold for $1,550,000 at list price after 1 day, while a home on Flagler Avenue sold for $640,000, 5% under list after 172 days. Condition, elevation, parking and a valid rental license move buyers more than anything else here. Have your elevation certificate, wind mitigation report and permits ready before you list.

Ryan and Megan run a home value review that compares your home to what closed nearby this summer.

Neighborhoods and price ranges

Key West and the rest of the Keys are not one market. The Key West median of $1,049,306 sits above the Monroe County median of $971,748, and both blend condos, conch cottages and waterfront homes.

• Old Town: Historic homes and cottages near Duval Street and the harbor. Historic district rules apply to exterior changes. Redfin shows a home on Catherine Street that sold for $2,335,000, 2% under list after 78 days.
• Casa Marina and the Meadows: Residential streets between Old Town and the south shore, with a mix of renovated homes and older houses.
• New Town: The east side of the island, with more ground-level homes, condos and newer construction. Redfin shows a home on Harriet Avenue that sold for $615,000 at list price after 46 days.
• Key Haven and Stock Island: Neighboring keys with canal homes, marinas and some of the lower price points near Key West.
• Middle and Upper Keys: Marathon, Islamorada and Key Largo offer more waterfront lots and boating access, with a longer drive to Key West and a shorter drive to the mainland.

Check the last three closed sales near the address you want, not the island average. Text Ryan and Megan for recent sales in any part of the Keys.

Taxes, insurance, flood zones and the homestead exemption

Florida has no state income tax on wages. Property tax works differently than most northern states. When you buy, the assessed value resets to market value, so the seller's tax bill is not your tax bill. Ask for a tax estimate based on your purchase price before you commit.

If the home is your permanent residence, file for the homestead exemption with the Monroe County Property Appraiser by March 1 of the tax year. The Florida Department of Revenue explains that the exemption reduces taxable value by up to $50,000. The first $25,000 applies to all property taxes, including school taxes. The second $25,000 applies to assessed value over $50,000 and only to non-school taxes. After the first year, the Save Our Homes rule limits annual assessment increases on a homestead to 3%. If you already hold a Florida homestead, portability lets you move up to $500,000 of that benefit to a new homestead, as long as you establish it within three years, according to the Lee County Property Appraiser.

Redfin reports that 97% of Key West properties face severe flood risk over 30 years, compared with 59% across Monroe County. Check the federal flood zone for any address before you make an offer. Zones that begin with A or V are Special Flood Hazard Areas, and a federally backed mortgage requires flood insurance there. Ask for an elevation certificate. In the Keys, the height of the lowest floor drives the flood premium more than almost anything else, and ground-level homes cost more to insure than elevated ones.

For wind coverage, insurers look hard at roof age, roof shape and window protection. Order a wind mitigation inspection, which documents features such as roof-to-wall connections and impact glass, because those features reduce premiums. Older homes often need a four-point inspection of the roof, electrical, plumbing and heating and cooling systems before an insurer will write a policy. Get insurance quotes during your inspection period, not after.

Condo buyers should read the association documents. Florida law now requires milestone inspections and structural integrity reserve studies for many older buildings of three stories or more, and associations must fund reserves for items such as roofs and structure. Ask for the latest reserve study, the budget, any pending special assessment and the rental rules, including minimum lease terms. Lenders also review the association, and a building with unresolved structural or financial issues is harder to finance. Condo owners need their own unit owner policy.

Short-term rental rules matter in Key West. The City of Key West classifies rentals of 28 days or less as transient, and every residential rental needs a City of Key West Business Tax Receipt. Do not assume a home earns nightly rental income. Confirm its license status in writing before you buy.

The Florida Keys are a state Area of Critical State Concern, and Monroe County limits how many new building permits it issues each year. That limit keeps supply tight and makes vacant lots with a permit allocation worth more. One road, the Overseas Highway, connects the Keys to the mainland, so hurricane evacuation plans and storm shutters are part of owning here.

Selling up north and buying in Florida

Many Keys buyers sell a home in New England or the Northeast first, then buy a primary or second home here. Ryan and Megan Winslow are brokers in Florida and Massachusetts, so one team coordinates both sides of the move.

Decide early whether the Keys home is your primary residence. That choice affects your homestead exemption, your loan terms and your insurance. Sell first and you buy with clear numbers. Buy first and you need a bridge plan for two payments and a long Keys closing timeline.

Talk with your tax advisor about the federal home sale exclusion on the home you sell and any gain above it. Ask Ryan and Megan how to line up both closings so you move once.

Outlook for the next 3 months

No one is able to promise where prices go. Key West sale prices rose 13.7% on a small number of sales, the Zillow index slipped 0.7% and the Monroe County median rose 1.5%. Read that as a stable market with a strong high end.

Days on market are long and competition is low, so buyers keep their leverage through the fall. Hurricane season runs through November, and activity usually picks up once it ends and seasonal residents return. That lifts showings, though it does not guarantee higher prices. Watch days on market and the Monroe County median in the next report.

Frequently asked questions

What is the median home price in Key West?

Redfin reports a median sale price of $1,049,306 for the three months ending August 2026, up 13.7% from a year earlier. Zillow puts the typical Key West home value at $1,007,374, down 0.7% over the past year.

What is the median home price in the Florida Keys?

Redfin reports a Monroe County median sale price of $971,748 for the three months ending August 2026, up 1.5% from a year earlier. Prices vary widely from Key Largo to Key West.

How long does it take to sell a home in Key West?

The median home spent 141 days on the market, 10 days longer than a year earlier, per Redfin. Zillow shows a median of 104 days to pending. Plan for a long sale even at a fair price.

Do I need flood insurance in Key West?

Plan on it. Redfin reports 97% of Key West properties face severe flood risk over 30 years, and 59% across Monroe County. A federally backed mortgage requires flood insurance in a Special Flood Hazard Area. Check the zone for each address.

Is short-term renting allowed in Key West?

Not without the right license. The City of Key West classifies rentals of 28 days or less as transient, and every residential rental needs a City of Key West Business Tax Receipt. Confirm a property's rental status before you buy for income.

Want to know what your home would sell for, or what you should offer on one? Text or call Ryan and Megan at 386-690-5858, or request a home value. Ryan and Megan are Mortgage Bankers with The Federal Savings Bank and Florida real estate brokers, so you get the buying, selling and financing picture in one conversation.

Sources: Redfin Key West housing market (three months ending August 2026), Redfin Monroe County housing market (three months ending August 2026), Zillow Key West home values (index and listings through August 31, 2026, sale price through July 31, 2026), City of Key West rental license guidance, Florida Department of Revenue homestead exemption guide and Lee County Property Appraiser portability guide. Figures cover August 2026 unless a row states another month. Numbers are rounded as published and are not a forecast.