Florida Keys Real Estate This Week: October 27, 2026

There is a lot happening in Florida Keys real estate right now, and the most useful numbers are the ones that come straight from the MLS.

I pulled the latest figures directly from FlexMLS on October 27, and September was a stronger month for residential sales than the same month last year. At the same time, housing policy is front and center in both Key West and Marathon, and a significant Citizens flood-insurance deadline is getting closer.

Here are the things I think buyers, sellers and property owners should actually pay attention to this week, plus what's going on in town this weekend.

According to the FlexMLS report I pulled on October 27, the entire MLS residential market had a stronger September than a year ago. 155 residential sales closed in September 2026, up 14.0% from 136 in September 2025. Closed-sale dollar volume rose 26.2%, to $230,822,540 from $182,937,925, and the median sale price rose 15.1%, to $1,010,000 from $877,500.

These figures cover all residential property types in the MLS, not just single-family homes.

2026 ran ahead of 2025 through much of the spring and summer. August dipped below last year's pace, while September moved back ahead with 155 residential closings compared with 136 a year earlier.

What the median does and doesn't tell you: September's median residential sale price was 15.1% higher than in September 2025. But a median is influenced by which properties happened to sell that month. That does not mean every home in the Keys is worth 15% more than it was a year ago.

The Keys contain very different submarkets, price points and property types, from Key West condos and historic homes to canal homes in the Lower Keys and waterfront estates. Individual home values still need to be evaluated locally.

To see how that plays out island by island, I also pulled year-to-date residential activity from January 1 through October 27, 2026. Marathon, in the Middle Keys, is included for comparison.

A few things stand out to me. Across all six areas, homes that sold this year closed at roughly 93% to 95.5% of their list price, after an average of about four to five months on the market. And the average sale price ranges from about $915,000 on Big Pine Key to about $2.15 million on Summerland Key.

Average prices reflect the mix of properties sold in each market and should not be interpreted as individual property appreciation. But that spread is a good reminder that "the Keys market" is really a collection of very different island markets.

Key West Mayor Sam Kaufman is holding an Affordable Housing Town Hall on Wednesday, October 28, from 5:30 to 8 p.m. in the City Commission Chambers at 1300 White Street.

According to the City of Key West, the discussion is expected to include:

• Existing affordable and workforce housing programs
• Rental and homeownership assistance
• Housing availability and eligibility
• Preserving existing affordable housing
• Creating new housing opportunities
• The City's Affordable Housing Trust Fund
• Partnerships between the City, Housing Authority, nonprofits and private property owners
• Key West's Housing Needs Assessment and Housing Action Plan

This matters far beyond people actively looking for affordable housing.

Why housing supply affects the entire Key West market: Housing influences whether teachers, restaurant workers, first responders, hospitality employees, tradespeople and other members of the local workforce can remain in the community. It also affects employers, rental demand, development decisions and the long-term character of Key West.

For property owners, it is worth paying attention whenever the City discusses how housing may be preserved, funded or created.

Affordable housing in Key West is not a side issue. It is connected to almost everything that makes this community function.

There is no single policy that solves it, which is why I think these conversations are important to follow, especially when they move from general discussion into actual programs, funding and development decisions.

The Marathon City Council voted on October 13 to pursue the transfer of 100 early-evacuation workforce housing building rights from Key Colony Beach and Layton.

These are part of the housing allocations originally awarded to the Keys after Hurricane Irma.

The proposed rights have significant restrictions. They are intended for multifamily housing, and occupants would be required to evacuate when a tourist evacuation is ordered during a storm.

The larger debate now is over how Marathon should allow those rights to be used. Council members have expressed concerns about speculative development and large clustered projects that might technically qualify as workforce housing without solving the housing problems the city is trying to address.

Marathon's City Council is scheduled to meet in a workshop at 5:30 p.m. on October 27. Keys Weekly reported that staff planned to bring an early draft of restrictions for the proposed workforce-housing rights to that session. Because this article was prepared before the workshop, we'll be watching for what comes next rather than assuming an outcome.

What Marathon's market looks like right now: My FlexMLS market summary for Marathon residential shows 26 sales in September 2026, up from 12 in September 2025, and 190 active listings, down from 218. With so few sales in a single month, percentage changes can look dramatic, so I would not read too much into any one month. It is useful context, though, as the city debates how much new housing to allow.

A second Marathon housing project is already moving ahead: At the October 13 meeting, the council also approved the use of 12 building rights for six affordable duplexes associated with Keys Health + Housing's Hope Project. That project is designed to provide affordable rentals and supportive housing for women and women with children.

Why this matters to property owners: Building rights are one of the reasons vacant land in the Florida Keys is unlike vacant land in most of the country. Owning a parcel does not necessarily mean you can immediately build a house on it. Allocation systems, zoning, environmental restrictions, flood requirements and other development rules can all affect what is possible.

One of the most important insurance dates for Florida Keys homeowners is now only a few months away.

Citizens Property Insurance Corporation says that beginning January 1, 2027, most new and renewing personal residential policies that include wind coverage will also require flood insurance regardless of the dwelling value, subject to the program's exemptions.

This is the final stage of a requirement that has been phased in over several years.

Citizens notes that condominium unit-owner policies, tenant content policies and policies excluding windstorm or hail coverage are among the policies exempt from this particular requirement.

Properties inside designated Special Flood Hazard Areas with applicable Citizens wind coverage have already been subject to flood-insurance requirements.

Why this matters in the Keys: When someone asks, “What will it cost me each month to own this house?” the mortgage is only part of the answer. Taxes, wind insurance, homeowners coverage, flood insurance, maintenance and, in some properties, association costs all need to be considered.

That is particularly important when comparing two homes that may have very different insurance profiles.

Monroe County continues to caution property owners that the FEMA preliminary coastal flood maps currently available are not final or adopted. Based on correspondence with FEMA in 2026, the county says another set of preliminary maps is expected before the new maps are finalized, and neither FEMA's current preliminary maps nor the county's appeal maps is expected to become the final map exactly as currently shown.

If you own in unincorporated Monroe County, the county's comparison tool shows the current effective map, FEMA's preliminary map and the county appeal map side by side. (It covers unincorporated areas only, not cities such as Key West.) I'm watching this for anyone planning a major renovation, redevelopment or new construction, because future flood maps can affect elevation and construction requirements.

If a friend asked me what's happening in town this weekend, the answer is easy: the boats are coming. Race World Offshore's 2026 Key West World Championship runs Sunday, November 1 through Sunday, November 8, based at Truman Waterfront Park.

One thing to get right before you make plans: Race Week begins this Sunday. The actual racing begins Wednesday. There is no championship race on Sunday, November 1. The race days are Wednesday, November 4, Friday, November 6 and Sunday, November 8.

Sunday is the kickoff. The World's Fastest Boat Parade is scheduled to roll down Duval Street at about 4 p.m. It's the one time all week you can see these boats up close on Duval.

Race schedules can change because of weather, water conditions or operational requirements, so check raceworldoffshore.com before you head out.

The local numbers matter more than the headlines. September brought more residential closings and more dollar volume than a year ago. But each island is moving at its own pace, local governments are wrestling with the reality of housing supply, and insurance changes are approaching that can directly affect the cost of owning property here.

None of that means buyers should stop buying or sellers should stop selling. It means the strategy should be based on the specific property, the specific island and the numbers that actually apply to it. That has always been true in the Florida Keys. It just matters even more right now.

FAQ

Were Florida Keys home sales up in September 2026?
Yes. According to FlexMLS, 155 residential sales closed across the entire MLS in September 2026, up 14.0% from 136 in September 2025. Closed-sale dollar volume rose 26.2%, to $230,822,540.

Did Florida Keys home values go up 15%?
The median residential sale price in September was $1,010,000, up 15.1% from $877,500 a year earlier. A median reflects which properties sold that month, so it does not mean every home gained 15%. Individual values should be judged against local comparable sales.

What are building rights in the Florida Keys?
Because development is tightly regulated throughout the Keys, ownership of a parcel does not always provide an immediate right to construct a home. Depending on the jurisdiction and property, allocation systems, zoning, environmental rules and other restrictions may affect development.

Will Citizens require flood insurance in 2027?
Citizens says that beginning January 1, 2027, most new and renewing personal residential policies with wind coverage will require flood coverage regardless of dwelling value, subject to applicable exemptions.

When are the 2026 Key West powerboat races?
Race World Offshore's Key West World Championship runs November 1 to 8, 2026, based at Truman Waterfront Park. Race Week opens Sunday, November 1 with the World's Fastest Boat Parade on Duval Street, but the racing itself begins Wednesday. Race days are Wednesday, November 4, Friday, November 6 and Sunday, November 8, subject to change.

Are Monroe County's new FEMA flood maps final?
No. Monroe County states that the currently displayed preliminary and appeal flood maps are not final or adopted, and another set of preliminary FEMA maps is expected before finalization. Neither is expected to become the final map exactly as shown.

Sources

• FlexMLS Yearly Market Comparison: entire MLS, residential, closed, September 2026 vs. September 2025
• FlexMLS Property Type Year to Date Activity Report: residential, January 1 – October 27, 2026
• FlexMLS Market Summary: Marathon residential, September 2026
• City of Key West: Mayor's Affordable Housing Town Hall Public Meeting
• Keys Weekly: Marathon City Council pursues extra building rights from KCB & Layton, with strings attached (October 15, 2026)
• Citizens Property Insurance Corporation: Flood Insurance Requirements
• Monroe County, Florida: Preliminary Coastal Flood Maps
• Race World Offshore: 2026 Key West World Championship
• Race World Offshore: Key West Schedule (subject to change)

Source: FlexMLS / MLS data. Reports prepared by Kate Baldwin on October 27, 2026. Information is deemed reliable but not guaranteed.

Thinking about buying or selling in the Keys?

If you're considering a move in Key West or the Lower Florida Keys, or you're trying to understand what your property is worth in today's market, I'm always happy to have a conversation. Call or text 305.240.7828, or ask me anything.

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General information only, not legal, tax, insurance or financial advice. Market data is from the sources listed and covers the periods stated.