The Key West Market: A 90-Day Perspective

Key West is a market where the details matter. A house on one block can attract a very different buyer than a similar house a few streets away. Condition, parking, flood exposure, renovation quality, and the rights attached to a property can all change the value equation.

Over the past few months, the most important distinction for buyers and sellers has been between properties that are positioned realistically for today's market and those still priced around yesterday's expectations.

I would be careful about treating Key West as one market. Old Town, Midtown West, Casa Marina, and Truman Annex each have different buyer profiles and different factors driving value.

What are the broader numbers telling us?

The latest publicly available figures point to a market that is active, but not one where sellers can assume buyers will meet any asking price.

• Key West: Redfin reports a median sale price of approximately $999,500 for the three months ending September 2026, down 17.7% year over year. It reports 92 homes sold in September, up 5% from September 2025, and a median 143 days on market. Its reported sale-to-list ratio was 94.3%. (Source: Redfin)
• Florida Keys / Monroe County: Momentum Research reports an October 2026 median closed price of $1,055,000, up 17.2% year over year, with 135 closed sales, 111 median days on market, and 91.4% of original asking price received. It also reports 17.4% of listings had price cuts. This is a broader Keys-wide snapshot, not a Key West neighborhood report. (Source: Momentum Research)
• Key West single-family, August: A local market summary citing Florida Realtors SunStats reported 110 active single-family listings, 22 pending, and 15 closed sales. The median sale price was $1.17 million, down 6.3% year over year. Pending sales were up 47%, while closed sales were down 25%. One month is a small sample, but the contrast suggests buyers were engaging even as closings lagged. (Source: Florida Keys Real Estate)

These figures use different reporting windows and methodologies. They should not be combined into one trend line. They do, however, reinforce a practical point: buyers are still making decisions, but pricing, presentation, and property-specific value matter.

What does this mean in the neighborhoods I watch?

Old Town

Old Town is not one uniform market. The block, the condition of the house, parking, pool, elevation, and quality of renovation can create substantial differences between otherwise comparable properties. Historic homes with thoughtful renovations and a clear story remain compelling, but buyers are more deliberate about what they are paying for.

For sellers, the first asking price and the first two weeks of presentation matter. For buyers, a property that has been sitting may offer room to negotiate, but days on market alone do not make a property a bargain. The reason it has been sitting matters.

Midtown West

Midtown West deserves to be evaluated on its own merits rather than treated as a discount version of Old Town. Buyers often compare lot size, parking, layout, condition, and proximity to Old Town. The $3.1 million sale at 1230 South Street is a useful example of what a distinctive property can achieve, but one transaction does not establish a market-wide benchmark.

For buyers, Midtown West can offer a different combination of space, residential character, and access. For sellers, the property needs to be compared with the right competing homes, not simply the nearest high-profile sale.

Casa Marina

Casa Marina attracts a different set of priorities: larger lots, parking, proximity to the beach, and a more residential setting. Buyers looking for a full-time home or a substantial second home may place a premium on those features.

The opportunity here is often in understanding the complete property, not just its interior square footage. Lot usability, flood exposure, elevation, outdoor space, and the cost of insurance all belong in the pricing conversation.

Truman Annex

Truman Annex remains a highly desirable address. The gated setting, walkability, and location have not changed. The economics of ownership have.

The special weekly transient rental rights ended on December 22, 2025. Affected properties can no longer operate as short-term rentals of less than one month under those former rights. The City placed the associated transient licenses into inactive status and voided them; owners may pursue non-transient licensing for longer-term rentals. (Source: Florida Keys Weekly Newspapers)

That change matters when evaluating comparable sales. A pre-expiration sale may have reflected the ability to generate weekly rental income. A buyer today cannot simply assume that same income stream is available. Those older sales may still help explain location value, condition, and buyer demand, but they should not be used as direct pricing evidence without accounting for the lost rental rights.

The buyer profile has shifted toward people purchasing Truman Annex for personal use, a second home, or longer-term rental use where permitted. Sellers need to price for the property and rights that exist today, not the investment model that existed before the sunset.

What should buyers understand right now?

There are opportunities, but they are not necessarily found by looking for the lowest asking price.

• Look beyond the list price. Evaluate condition, deferred maintenance, insurance, flood exposure, elevation, and likely renovation costs together.
• Ask what the property can legally do. Rental rights, permits, HARC approvals, and zoning should be verified rather than assumed.
• Be prepared to negotiate intelligently. A seller with an extended market time may be more flexible, but a well-positioned property can still attract serious competition.
• Consider both historic and new construction. A properly renovated historic home offers character and established location. New construction can offer modern systems, layout, and reduced near-term maintenance. The right comparison is total ownership cost and property quality, not simply price per square foot.

What should sellers understand right now?

The market is not necessarily rejecting good properties. It is rejecting the assumption that every property will command a premium regardless of price or presentation.

A successful sale starts with a realistic understanding of the competition. The first two weeks are important. Preparation, photography, video, pricing, and distribution need to work together from the beginning.

For historic properties, the story matters, but it has to be supported by the facts: renovation quality, documented improvements, HARC approvals, flood exposure, and the details that make that particular block desirable.

For newer homes, construction quality, permits, elevation, systems, finishes, and warranties deserve attention. Buyers at the higher end are looking closely at what they are getting for their money.

Where do I see opportunity in Key West?

I see the strongest opportunities in three areas:

1. Well-positioned historic homes. Properties with thoughtful renovations, strong architectural character, and realistic pricing can stand apart.
2. Quality new construction. Buyers who want modern layouts and systems without taking on a major renovation may find value in well-executed new homes, provided the construction and documentation support the asking price.
3. Properties that need a more thoughtful strategy. Some sellers are still anchored to older comparable sales or an aspirational asking price. Where the property itself is sound, a change in pricing or presentation can create an opportunity for a buyer and a better path forward for a seller.

For me, the common thread is that the property has to be evaluated on its own merits. A citywide median does not price a historic home on Eaton Street, a new residence in Casa Marina, or a condominium in Truman Annex.

Which numbers matter before making a neighborhood-specific decision?

The public figures above provide context, but I would not present them as definitive 90-day statistics for Old Town, Midtown West, Casa Marina, or Truman Annex.

For a precise neighborhood update, I would pull the following from the MLS for August 8 through November 6, 2026, comparing the same period in 2025 where sample size allows:

• Closed sales and total volume: actual transaction activity
• Median and average sale price: price movement, with sample-size context
• Median price per square foot: useful only when property types are comparable
• New listings and active inventory: competition facing sellers
• Pending sales: current buyer engagement
• Median days to contract and total DOM: how long properties are taking to sell
• Sale price to original list price: how accurately sellers are pricing
• Sale price to final list price: negotiation after price adjustments
• Price reductions: how much repricing is occurring
• Single-family vs. condo/townhouse: avoids mixing very different property types
• Price bands ($1.5M–$3M, $3M–$5M, and $5M+): more relevant to the high-end market

I would also separate historic homes from newer construction where the data permits, and isolate Truman Annex sales before and after December 22, 2025. If the sample is small, I would say so rather than force a conclusion.

A note from me

The Key West market rewards local knowledge and careful judgment. The right price is not determined by a broad headline, and the right property is not always the one with the lowest price per square foot.

Whether you are considering a move, thinking about selling, or simply keeping an eye on the value of your property, I am happy to give you a candid assessment of what is happening on your particular street.

Talk soon,

Damian

Damian Vantriglia, REALTOR® Berkshire Hathaway HomeServices Keys Real Estate | Luxury Collection 305-741-9411 · damian@keysrealestate.com