Areas We Serve

Windermere Real Estate

Your local REALTOR® serving Windermere and surrounding communities.

Market Overview

Luxury lakefront living and prestigious communities like Isleworth and Keene's Pointe. Known for excellent schools, privacy, and proximity to Disney and Dr. Phillips. A top choice for executives and families seeking upscale homes. Windermere's chain of lakes, tree-lined streets, and exclusive estates define one of Central Florida's most coveted addresses.

Popular Communities in Windermere

Isleworth

Gated golf community with multi-million dollar estates on the Butler Chain of Lakes.

Keene's Pointe

Luxury gated community with a Jack Nicklaus-designed golf course.

Lake Butler Sound

Elegant waterfront homes with private docks and lake access.

Windermere Trails

Newer homes offering a more accessible entry point to the Windermere lifestyle.

Frequently Asked Questions

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 Windermere median home price in 2026 is approximately $875,000, but the range is dramatic. Windermere Trails townhomes start around $475,000, established neighborhoods trade between $700,000 and $1.5 million, and Isleworth estates regularly exceed $5 million with a top sale above $30 million. It's one of the widest price bands in Central Florida.

Isleworth is the flagship, offering a Nick Faldo-redesigned golf course and 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 HOA and club initiation fees that together can exceed $100,000 upfront plus $30,000-plus annually.

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.

Luxury markets like Windermere have softened somewhat in 2026, with inventory around 6 months of supply — buyer-friendly by historical standards. High-end homes above $2 million are now averaging 90 to 120 days on market, and I'm negotiating meaningful price reductions on 40 percent of my Windermere transactions. It's a strong window for well-qualified luxury buyers.

Ready to Explore Windermere?

Whether you're buying, selling, or investing in Windermere, I'm here to help you every step of the way.