Windermere Real Estate

Windermere is one of the most prestigious addresses in Central Florida. My clients here value the privacy, the Butler Chain of Lakes offering 11 interconnected lakes for boating and skiing, and being zoned to top-rated Orange County schools like Windermere High. It's a quiet, tree-lined community that feels a world away yet sits only 15 miles from downtown Orlando.

The August 2026 median sale price for a single-family home in Windermere was $960,000, down 12.7 percent from $1,100,000 a year earlier, with a year to date median of $970,000, down 3.4 percent. The range is dramatic: townhomes and condos have a median of $395,000, up 6.8 percent, established neighborhoods trade between $700,000 and $1.5 million, and Isleworth estates regularly exceed $5 million. It's one of the widest price bands in Central Florida. Market figures as of August 2026. Source: Stellar MLS.

Isleworth is the flagship, offering a championship golf course alongside lakefront estates. Keene's Pointe pairs a Jack Nicklaus course with slightly more accessible pricing. Lake Butler Sound is my pick for waterfront enthusiasts wanting private docks. For buyers under $700,000, Windermere Trails and Windermere Cay are the smart entry points.

Orange County effective property tax rates in Windermere are about 1.0 to 1.2 percent, though absolute dollars are high given elevated home values. HOA fees vary sharply: $150 to $300 per month in Windermere Trails, $350 to $600 in Keene's Pointe, and Isleworth carries club initiation and annual fees well above typical HOA costs. I will get you the current figures before you make any decision.

Windermere is roughly 15 miles from downtown Orlando, a 25 to 30-minute drive via FL-429 and I-4. Walt Disney World sits about 10 miles south, a 15 to 20-minute drive. Dr. Phillips Restaurant Row is just 8 minutes away, which is a major lifestyle draw for the executives and physicians I work with here.

Windermere sellers are accepting the lowest share of list price of any market on this site, and that favors you. Windermere single-family homes took 91 days to sell in August 2026, up from 70 a year earlier, supply sits at 4.6 months, and sellers accepted 95.1 percent of list price, down from 96.2 percent. On a $960,000 home, that gap is roughly $47,000 of negotiating room. Townhomes and condos are tighter at 4.0 months of supply. Market figures as of August 2026. Source: Stellar MLS.