Windermere is a small charming town located in West Orange County. As an isthmus between some of the largest lakes on the famous Butler Chain of lakes Windermere is one of the most beautiful and prestigious towns to live in the greater Orlando area and all of Florida.Windermere Florida Real Estate

The city of Windermere is dedicated to the preservation of the natural atmosphere and history of the downtown area. Downtown Windermere is centered on none other than Main Street. There are a number of historic buildings and store fronts in downtown, ornate street lamps, small central park and even a few unpaved streets. Looking for a homemade breakfast or lunch from scratch? Trip Advisor says to check out Dixie Cream Café located in a charming 50’s style building. The Downtown Business Committee is a team of local business owners dedicated to the preservation of the historic atmosphere and putting on family friendly events for the community including old car shows, fall festivals, food truck fun, and live local musicians. Every Friday from 9-2 is the Windermere Farmer’s Market in front of Town Hall full of fresh local food, produce, and hand crafted goods.


Windermere Florida Real EstateThe history of Main Street is popular in Windermere but Windermere is probably most known for its number of resort style housing communities, lake front estate homes, and long list of big name residents. There is a home to fit every lifestyle in Windermere from Condos to single family homes to sprawling mansions. Some of the most noteworthy communities in Windermere include Isleworth, Keene’s Pointe, and Lake Butler Sound.

People look to live in Windermere for the quiet small town lifestyle in the most beautiful lake front real estate in West Orange County. Windermere also offers young residents some of the best education opportunities found in the state of Florida and the United States. The public schools in Windermere are part of the Orange County School District with some of the highest ranked schools in Florida. There are also a large number of highly prestigious private schools including Windermere Prep, a school world renowned for its excellence.

Windermere is just minutes from everything in the Greater Orlando area located between the up and coming Horizon West area located in Winter Garden and the Dr. Phillips area of Orlando. Windermere is just minutes from amenities such as Restaurant Row, Mall of Millennia, Downtown Orlando, and all area theme parks including Walt Disney World.

Considering a home in Windermere? Let us help you with our unique buying services and dedication to finding you the perfect home. Our goal is to help home buyers find their perfect Orlando area home.

Start your search for all homes and information in these communities located in Windermere Florida

Isleworth in Windermere

Keene’s Point Community in Windermere

Chaine Du Lac


Casa Del Lago

Carrington Townhomes

Sunset Bay

Vineyards Windermere

Lake Davis Reserve

Estates at Windermere

Casabella at Windermere


Provence at Lake Sheen

Gardens of Isleworth

Keene’s Point

Lake Cawood Estates

Manors at Butler Bay

Butler Bay at Windermere Club

Peachtree Park

Worthington Park


Tilden's Grove

Ashlin Park

Harbor Isles

Belmere Village


Sawyer Sound

Windermere Pointe


Magnolia Park

Southern Acres

Westover Club


Willows @ Lake Rhea

Woods of Windermere

Marina Bay

Windermere Trails

The Preserve at the Lakes of Windermere


Images by Christian Lambert & Matt Correia Flickr

Brand New Townhouses in Windermere

Brand New Townhouses in Windermere

Vineyard Square is one of Windemere's newest premier townhouse communities. Located along Calera Aly in Windemere, this new construction townhouse complex features 2-4 bedrooms, 2 1/2 bathrooms, a two-car garage and all of the other top-rated interior Continue reading

Windermere Landing

Windermere Landing

Windermere Landing is a newer housing community in Windermere. This community is located on Chase Road behind Keene’s Point and offers energy efficient homes in one of the most sought after places to live in Central Florida. There are three different Continue reading

Vineyard Square

Vineyard Square

Vineyard Square is a new townhome community of Windermere. These homes offer low maintenance living in one of the most sought after places to live in Central Florida. It is a great neighborhood for nature lovers not far from the Tibet-Butler Continue reading



Estancia is a brand new residential community in Windermere Florida. These homes allow you to live in this highly sought after town among old moss covered trees and unpaved streets in today's modern homes. Who knows you might even end up with a famous Continue reading

Rosser Reserve

Rosser Reserve

Rosser Reserve is one of the newest luxury communities of Windermere. Located on the shores of Lake Down along the Butler Chain of Lakes, this community is in one of the most sought after places in Windermere right across from the main gate of the famous Continue reading



Vineyards is a quiet new housing community of Windermere Florida. Windermere is one of the most sought after towns to live in Central Florida known for being surrounded by the gorgeous Butler Chain of Lakes, number of estate style homes, and large list of Continue reading

The Preserve at the Lakes of Windermere

The Preserve at the Lakes of Windermere

The Preserve at the Lakes of Windermere-Peachtree is a gated housing community in the town of Windermere near the Horizon West area. This community is located on Reams Road and Greenbank Avenue close to several area amenities. The houses in The Continue reading

Windermere Trails

Windermere Trails

Windermere Trails is a newer housing community in the town of Windermere near the Horizon’s West area. This community is located on Reams Road and Silver Lake Drive. Homes in Windermere Trails are built by Meritage Homes and Beazer Homes. Meritage Continue reading

Sandy Shores

Sandy Shores

In between the housing communities of Reserve at Lake Butler Sound and Waterstone is the well-established hidden gem community of Sandy Shores. This neighborhood is located in the heart of Windermere along the southern shore of Lake Butler on Winter Continue reading

Oxford Moor

Oxford Moor

Oxford Moor is a housing community in the town of Windermere. This community is made up of 85 Mediterranean and contemporary style estate homes located on Winter Garden Vineland Road just west of Marleon Drive. Oxford Moor is a private gated community Continue reading

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