Are home prices in Windermere expected to rise or level off in 2026?

If you’re looking at Windermere, Florida, you’re in one of Central Florida’s premium-neighborhoods, so the rules shift slightly compared to the broader market. Here’s how 2025 is playing out and what to expect moving forward.

Current trend snapshot:
Statewide for Florida, the median sales price of single-family homes is holding at approximately $410,000 for the third quarter of 2025, down ~1.2% year-over-year. (Florida Realtors, Redfin) Inventory is growing and the months-of-supply is edging toward more balanced territory. (Redfin)
In Windermere’s premium segment, prices tend to lag or exceed broader state metrics because of lot size, luxury finishes, and lifestyle amenities.

What does that mean for price direction in Windermere?

• Expect moderate upward pressure, not runaway gains. Because inventory in higher-end homes often remains constrained, luxury markets like Windermere can hold value well.

• But don’t assume massive gains are automatic. Given that Florida overall is seeing prices “level off” rather than skyrocketing, Windermere’s appreciation will likely be steadier and dependent on condition, neighborhood, and upgrades.

• Sellers in Windermere will still command good prices—if the home checks the boxes: great location, high-end finishes, desirable lot, and low deferred maintenance. Buyers, however, will benefit from more negotiating room than the overheated years.

Advice for each side:

• Buyers: Don’t wait for huge discounts—luxury homes still maintain value. Use the market’s stabilization to negotiate wisely (e.g., inspection items, upgrades, closing costs) rather than expecting a fire-sale.

• Sellers: Pricing matters more than ever. In a market where some buyers have more options, you want to present your luxury home with the right price, quality staging, marketing, and highlight district foliage, lake access, community features. If you overprice expecting 2021-style jump, you risk cabin-fever on the market.

Bottom line:
Windermere remains a strong hold in 2025—but expect maturity rather than mania. The market is less “wild boom” and more “smart, careful growth.” With my local insights in West Orlando/Windermere area, I can help you benchmark the true value in your specific Windermere micro-neighborhood.

Interested in a recent sales review of luxury homes in Windermere? I can pull comparable stats for your specific street, so you know exactly where you stand.