Upper Keys Neighborhoods
Six Islands.
Two oceans.
One stretch of road.
From Key Largo to Lower Matecumbe, the Upper Keys stretch across more than 30 miles of coastline — each community with its own character, its own water, and its own real estate story.
The Atlantic Ocean borders the east side — sunrise views, deeper water, ocean fishing. Florida Bay and the Gulf of Mexico border the west — calmer water, spectacular sunsets, backcountry fishing. Choosing your side before you search is the single most important decision most buyers don't know they need to make.
Beyond oceanside versus bayside, each community has its own character: price tier, property mix, deed restrictions, rental culture, and lifestyle feel. We know the differences. We'll help you find your fit.
Oceanside
Bayside
Find your island
Every stretch of the Upper Keys has its own character. Let us show you where you belong.
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Featured Listings
The Keys to the Islands
Upper Keys Real Estate: Midyear 2026 Market Report
The numbers are in and for buyers, sellers, and anyone watching the Upper Keys real estate market, the first half of 2026 tells a compelling story.
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Villa Lago Named Sotheby's Extraordinary Property of the Day
We are proud to announce that Villa Lago — 75090 Overseas Highway, Islamorada — has been selected as the Sotheby's International Realty® Extraordinary Property of the Day, featured across the brand's global social media channels to an audience of more than one million followers worldwide.
Ready to find your place in the Keys?
Buying, selling, or simply curious what your property is worth. No pressure — just honest conversation from people who know this place better than anyone.