Spring 2026 Island Estate Report | Key West Market Update

The Key West market entered the spring of 2026 in a familiar posture: constrained inventory, steady luxury demand, and a buyer pool that has grown more selective, not smaller.

What follows is a read on where the market stands and what it suggests for the months ahead.

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The Headline Numbers

• Active inventory remains below three months of supply across most Old Town segments — technically a seller's market, though one behaving more cautiously than the headlines suggest.
• Median days on market shortened modestly from the prior quarter, particularly for properties priced between $2M and $5M.
• Median sale price held firm, with modest appreciation in single-family Old Town homes and softer movement in condo inventory.
• Luxury segment ($5M+) continues to transact quietly, often off the public market.

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What Is Actually Moving

The properties selling well share a consistent profile: mature landscaping, recent systems (roof, HVAC, electrical), and a coherent interior. Properties requiring significant renovation are sitting longer, even in prime locations, as buyers factor in the rising cost of island construction and the time involved in HARC review.

The message is clear — buyers are paying for readiness, not potential.

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The Insurance Factor

Insurance remains the single most discussed variable in every transaction. Premiums in coastal zones have stabilized relative to the volatility of prior years, but underwriting requirements — wind mitigation, roof age, elevation — are scrutinized more closely than ever.

For sellers, a current wind mitigation report and a roof within underwriting tolerance have become near-prerequisites for a smooth sale. For buyers, understanding the insurance landscape before making an offer is no longer optional.

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Off-Market and the Luxury Quiet

A meaningful share of high-end transactions continue to occur without ever reaching the public listing services. These are relationships transactions — properties matched to pre-qualified buyers through agent networks. If the public market feels thin at the top end, it is partly because the top end operates on a different channel.

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What to Watch

Heading into the back half of the year, the variables to watch are interest rate movement, insurance carrier appetite, and whether the seasonal influx of second-home buyers translates into contracted inventory. The fundamentals — limited land, enduring demand, geographic constraint — remain the island's long-term argument.

For a tailored read on your specific neighborhood or property, the conversation is always the best starting point.

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Damian Vantriglia is a Key West native and REALTOR® with Berkshire Hathaway HomeServices Keys Real Estate. Market observations are directional and not a substitute for a property-specific consultation.