Upper Keys Real Estate: Midyear 2026 Market Report

Ocean Sotheby's International Realty closed the first six months of 2026 with over $388.3 million in total sales volume company-wide — up from $222.3 million in the same period last year. That is not a modest gain. It is a signal that this market, and the clients who trust us to navigate it, are moving with confidence.

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Ocean Sotheby's International Realty: YTD 2026 by the Numbers

$388.3M — Total sales volume, company-wide, YTD  2026

‍$259M — Total sales volume, Upper Keys office

‍$3.41M — Average sales price, Upper Keys office

‍$22M+ — Top sale in the Florida Keys, H1 2026 (Upper Keys & Key West office)

Ocean SIR finished the first half of 2026 as the #1 office in the Upper Florida Keys, holding a 7.66% market share with the Florida Keys Board of Realtors and the most followed local real estate brand on Instagram and YouTube.

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Beyond the volume figures, the firm claimed:

• Highest sale Keys-wide in 2026
• Highest sale in the Sunset Key neighborhood
• Highest sale in Key West
• Highest sale on Upper Matecumbe Key (Avocado St — co-listed by Leslie Leopold)
• Highest sale on Lower Matecumbe Key (Costa Bravo — co-sold by Leslie Leopold)
• 50% of the top 10 sales throughout the Florida Keys

These results are backed by 1 dedicated marketing team across 3 offices Keys-wide, an infrastructure that no independent brokerage in this market can replicate.

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A Note From Leslie

Through the first half of 2026, Leslie Leopold co-sold a total volume of $42,872,500 across some of the most significant transactions the Upper Keys market has seen this year, including both the highest sale on Upper Matecumbe and Lower Matecumbe Key.

For sellers considering when and how to bring their property to market, the midyear data is clear: well-represented properties in this market are transacting at record levels. The buyers are here. The question is whether your property is positioned to reach them.

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What This Means If You're Buying or Selling

For sellers: inventory remains limited and well-priced, well-marketed properties are moving. With an average sales price of $3.41M in the Upper Keys and a top sale exceeding $22M, the range of what this market can deliver is significant — and representation matters at every level.

For buyers: the Upper Keys market rewards those who move with clarity and local knowledge. Understanding which properties represent genuine value — and which ones don't — requires the kind of insight that only comes from decades in this market.

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Whether you are thinking about selling your Florida Keys home or ready to begin your search, we would welcome the conversation. Connect with Leslie & Annie →

View our current listings and sold portfolio to see what representation looks like at this level. Explore properties →