Windermere


Windermere is an incorporated town in western Orange County known for its lakeside setting, luxury homes, and quiet residential character along the Butler Chain of Lakes. The community is defined by tree-lined streets, waterfront properties, and a small-town atmosphere just minutes from Orlando.


Windermere borders both Horizon West and Winter Garden, which is why these areas are often referenced together in real estate searches. Nearby neighborhoods share schools, shopping, dining, and major road access, allowing residents to enjoy Windermere’s lake-focused lifestyle while remaining closely connected to the surrounding West Orange County communities.

Windermere Real Estate Snapshot

Average Price $2.1M
Lowest Price $295K
Highest Price $27M
Total Listings 294
Avg. Days On Market 102
Avg. Price/SQFT $441

Property Types (active listings)

Windermere Properties


Windermere Market Snapshot
Sold Homes 2025

616 Homes Sold Residential 2025
$900,000 Median Sold Price Close Price
65 Days Average Days On Market (ADOM)

Homes & Neighborhoods in Windermere 

Windermere is an incorporated town in southwest Orange County known for luxury homes, lakefront living, and proximity to both Winter Garden and Horizon West. Windermere homes for sale include gated estates, waterfront properties on the Butler Chain of Lakes, and established residential neighborhoods with custom-built homes and upscale amenities.

Many Windermere neighborhoods sit minutes from Winter Garden’s historic downtown and overlap geographically with Horizon West, which is why these three areas are often searched together in real estate listings, school zoning, and mailing addresses. Buyers comparing Windermere, Winter Garden, and Horizon West typically evaluate home age, lake access, community style, and proximity to major roadways.

Windermere Recreation, Lifestyle & Nearby Communities

Windermere is best known for the Butler Chain of Lakes, offering boating, fishing, and water sports. The town also features a small historic downtown, private golf communities such as Isleworth and Keene’s Pointe, and access to nearby shopping, dining, and entertainment in Winter Garden and Horizon West.

Residents benefit from shared infrastructure across west Orange County, including major highways, schools, and commercial centers. This connectivity allows Windermere homeowners to enjoy a quieter, residential setting while remaining close to the newer developments of Horizon West and the walkable downtown lifestyle of Winter Garden.

Windermere Location & Area Overview

Windermere is located just west of Orlando and south of Winter Garden, with Horizon West directly adjacent to the town’s western edge. Its location near State Road 429 and the Florida Turnpike provides convenient access throughout Central Florida, including employment centers and major attractions.

Because of the close relationship between Windermere, Winter Garden, and Horizon West, these areas are commonly grouped together in buyer searches. Windermere offers a distinct identity within this region, combining lakefront living, established neighborhoods, and proximity to the broader west Orange County real estate market.


Florida Homes Group Logo

Talk With a Local Expert in Horizon West, Winter Garden & Windermere

Get in Touch About Florida Homes Group

Windermere FAQs

Is Windermere, FL a good place to live for families and professionals?

Yes. Windermere is considered a desirable place to live for families and professionals due to its quiet residential setting, access to highly regarded schools, and proximity to major employment centers. Many residents also consider nearby Winter Garden and Horizon West when comparing housing options and lifestyle preferences.

What are the pros and cons of living in Windermere compared to Winter Garden or Horizon West?

Windermere offers a more private, lakeside lifestyle with larger homes and waterfront access, while Winter Garden provides a walkable historic downtown and Horizon West features newer, master-planned communities. Windermere typically has higher home prices and lower inventory, which can be a drawback for some buyers but appealing for those seeking exclusivity.

How expensive is it to live in Windermere?

Windermere generally has higher home prices than nearby areas such as Winter Garden and Horizon West, particularly for waterfront and luxury properties. The cost of living reflects larger home sizes, lake access, and established neighborhoods, though buyers may find more variety at different price points in adjacent communities.

Are schools in Windermere highly rated and is it a safe community?

Windermere is served by Orange County Public Schools and is often associated with well-rated school zones. The town is also known for its low-density residential layout and strong sense of community, contributing to its reputation as a safe and family-friendly area.

What is the lifestyle like in Windermere?

The Windermere lifestyle centers around lakefront living, outdoor recreation, and private residential communities. Many residents enjoy boating on the Butler Chain of Lakes, golf club amenities, and a quieter pace of life while remaining close to shopping, dining, and events in Winter Garden and Horizon West.

How close is Windermere to Disney World, downtown Orlando, and major highways?

Windermere is located just minutes from Walt Disney World and offers convenient access to downtown Orlando via State Road 429 and the Florida Turnpike. Its location also places residents close to Winter Garden, Horizon West, and other west Orange County destinations.

Which Windermere neighborhoods are most popular?

Popular Windermere neighborhoods include Isleworth and Keene’s Pointe, which are known for gated entrances, golf courses, and waterfront homes. Buyers also compare nearby communities in Winter Garden and Horizon West when evaluating home styles, pricing, and neighborhood amenities.

How does Horizon West compare to Windermere for homebuyers?

Horizon West offers newer construction and master-planned neighborhoods, while Windermere focuses on established communities and lakefront estates. Buyers often compare the two areas based on home age, price point, amenities, and proximity to Winter Garden and major roadways.