For the last few years, buying a home in Windermere meant moving fast, waiving contingencies, and hoping your offer was the one that stood out among a dozen others. That era isn't entirely gone, but it's fading. Windermere's housing market in 2026 is shifting toward something buyers here haven't see

Most of Florida's housing market is cooling off in 2026. Windermere's $3 million-and-up segment isn't reading the same memo. Statewide, Florida is working through a healthy rebalancing. Inventory is loosening, homes are sitting on the market longer than they did a couple of years ago, and buyers fin

If you're buying, selling, or just keeping an eye on home values in Windermere, Florida, here's your mid-year snapshot of exactly what happened in our local market through the end of June 2026. I pulled the numbers straight from the MLS — 363 closed home sales across Windermere and the surrounding 3