According to realtor.com, In June 2025, the median listing price of a home in Windermere, Florida was $1.1 million, a decrease of -9.4% from the previous year. The median price per square foot for a listing house was $329. $799K was the median price of a home sold.

A limited number of townhomes, gated community houses, luxury estates on the Butler Chain of Lakes, and high-end single-family homes are all available in Windermere. Features like expansive lots, private docks, pools, and custom architecture are common in many properties.

Known for their upscale amenities, beachfront homes, and golf courses, popular neighbourhoods include Isleworth, Lake Butler Sound, and Keenes Pointe. For purchasers looking for accessibility and attractiveness, Windsor Landing and Windermere's historic town centre are also desirable locations.

Olympia High School, Gotha Middle School, and Windermere Elementary are among the well-regarded public schools in Windermere. Well-known private schools like Windermere Preparatory School, which offers a college-prep curriculum from pre-K through 12th grade, are also available to families.

Numerous neighbourhood bakeries, cafes, and family-run eateries can be found in Windermere. At Town Square Park, locals also take pleasure in a monthly food truck festival. Just a short drive away are good alternatives for ethnic cuisine, casual dining, and gourmet dining at nearby Dr. Phillips and Winter Garden.