Windermere
Lakefront estates and luxury living in one of Central Florida's most prestigious communities. Windermere is where Southwest Orlando's finest homes meet Chain of Lakes living.
The crown jewel of Southwest Orlando.
Windermere is consistently ranked among the most desirable communities in Central Florida. Situated on the prestigious Butler Chain of Lakes, this town of approximately 5,000 residents is known for its estate-style homes, mature oak canopies, and an atmosphere of refined privacy.
Home to several professional athletes and executives, Windermere offers gated communities like Isleworth, Butler Bay, and Windermere Club alongside custom lakefront estates that regularly trade in the multi-million-dollar range. The town maintains strict zoning that preserves its small-town character even as surrounding areas develop.
The Windermere area is served by top-rated Orange County Public Schools, including Windermere High School and Gotha Middle School. The town's proximity to the Butler Chain of Lakes makes it a paradise for boating, fishing, and watersports enthusiasts.
Where to look in Windermere.
Isleworth
Gated golf and lakefront community with estates from $1M to $10M+. Home to Isleworth Golf & Country Club.
Butler Bay
Waterfront and interior homes with access to the Butler Chain. A mix of custom estates and planned communities.
Windermere Club
Gated community with a golf course, tennis, and a family-friendly atmosphere. Homes from the $500Ks to $1M+.
Keene's Pointe
Master-planned community with a Jack Nicklaus-designed golf course. Family-oriented with excellent schools nearby.
Tilden's Grove
Upscale single-family community with tree-lined streets, a community pool, and proximity to downtown Windermere.
Where is Windermere?
Living in Windermere, answered.
A few questions buyers and relocators ask most often about Windermere.
What's it like to live in Windermere?
Windermere is one of Central Florida's most prestigious communities, known for lakefront estates, mature oak canopies, and refined privacy on the Butler Chain of Lakes. It's a small town of roughly 5,000 residents with a strong sense of exclusivity.
Is Windermere a good fit for luxury buyers?
Very much so. Gated communities like Isleworth, Butler Bay, and Windermere Club feature custom estates that regularly trade in the multi-million-dollar range, and the town's strict zoning preserves its character.
What are the schools like?
Windermere is served by top-rated Orange County Public Schools, including Windermere High School and Gotha Middle School.
How close is Windermere to Disney?
About 15 minutes, which makes it convenient for theme park access while still feeling like a world away.
What can I do outdoors in Windermere?
The Butler Chain of Lakes is a paradise for boating, fishing, and watersports, and the area's tree-lined streets and lakefront parks make it easy to stay outdoors year-round.
What is an HOA and should I expect one?
Homeowners associations are common across Southwest Orlando's master-planned communities, and Windermere is no exception. They manage shared common areas and set community rules, though the specifics vary from one community to the next. I'll go over each home's HOA details before you make an offer so you know exactly what you're getting into.
What is a CDD?
A Community Development District is a special taxing district that funds community infrastructure like roads, utilities, and amenities. Homes in newer master-planned communities often carry a CDD assessment. I'll show you the exact CDD for any home you're considering so there are no surprises at closing.
How does home insurance work in Florida?
Florida home insurance works differently from most other states. Policies typically bundle dwelling, windstorm, and liability coverage, and flood insurance is usually a separate policy. Premiums vary by location, the age of the roof, and the coverage you choose, so I can point you to local carriers and include insurance estimates in your offer review.
How do property taxes work, and what is the homestead exemption?
Florida property taxes are set by the county, and owner-occupants who make a home their primary residence can apply for a homestead exemption, which reduces the assessed value taxed for most purposes. That exemption applies only to your primary home; investment and second homes are taxed at the non-homestead rate.
Interested in Windermere?
Windermere's luxury market moves quickly. Let me help you navigate the options and find the right property for your lifestyle and budget.
Talk About Windermere