Windermere High School, Windermere, FL, Real Estate

Windermere High School is a 9-12 school in the Orange School District school district, and is located at 5523 Winter Garden Vineland Road in Windermere, FL. The school services all or some of: Orlando, Windermere, Winter Garden, and Golden Oak. Windermere High School currently has 218 single family homes for sale with an average list price of $1,904,546.49, 34 townhouses for sale with an average list price of $409,827.15, 5 condos for sale with an average list price of $3,854,900, and 11 lots for sale with an average list price of $2,965,363.55 that attend the school. The average annual property tax for homes that attend Windermere High School is $9,894.73.

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Arlington Bay

Arlington Bay is a single-family home community in Orlando, Florida, built between 2005 and 2006. It currently has 2 single family homes for sale with an average list price of $583,950. The homes range in size from 2,042 ft2 to 2,824 ft2. The HOA fees range from $41 to $50 per month. The average annual property tax for Arlington Bay is $5,087.76. It is located in Orange County. The Arlington Bay subdivision is a gated, single family home community in Orlando, FL. Arlington Bay features 93 homes, most were constructed in 2005 and 2006. The homes range in square footage from 1,561 sqft to 3,041 sqft. 15 homes are nestled on the 2 ponds situated in Arlington Bay. This subdivision is located West of Winter Garden Vineland Road, in between Lake Sheen and Lake Mabel. ... Read more
Median Price: $505,000
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Arrowhead Lakes

Arrowhead Lakes is a single-family home community in Winter Garden, Florida, built between 1950 and 2002. It currently has 1 single family home for sale with a list price of $650,000. The homes range in size from 1,008 ft2 to 3,392 ft2. The average annual property tax for Arrowhead Lakes is $3,412.48. It is located in Orange County. ... Read more
Median Price: $490,000
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Ashlin Park

Ashlin Park is a single-family home and townhouse community in the Lakeside Village neighborhood of Windermere, Florida, built between 2014 and 2017. It currently has 4 single family homes for sale with an average list price of $717,725 and 2 townhouses for sale with an average list price of $419,000. The homes range in size from 1,466 ft2 to 3,092 ft2. The HOA fees range from $60 to $347 per month. The average annual property tax for Ashlin Park is $5,488.65. It is located in Orange County. ... Read more
Median Price: $459,000
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Bellaria

Bellaria is a single-family home community in Windermere, Florida, built between 2007 and 2015. It currently has 2 single family homes for sale with an average list price of $3,275,000. The homes range in size from 3,640 ft2 to 6,930 ft2. The HOA fees range from $447 to $499 per month. The average annual property tax for Bellaria is $19,978.04. It is located in Orange County. ... Read more
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Butler Bay

Butler Bay is a single-family home community in Windermere, Florida, built between 1983 and 2008. It currently has 3 single family homes for sale with an average list price of $2,261,333.33. The homes range in size from 2,649 ft2 to 6,819 ft2. The HOA fees range from $108 to $392 per month. The average annual property tax for Butler Bay is $11,901.21. It is located in Orange County. Butler Bay is a desirable residential neighborhood, renowned for its serene lakeside setting and relaxed upscale living. Nestled near the Butler Chain of Lakes, including scenic spots like Lake Crescent and Lake Roberts, the area features expansive single-family homes—many waterfront or lake-view—with spacious lots shaded by mature trees. Developed primarily since the 1980s, Butler Bay includes established subdivisions such as the Manors at Butler Bay and parts associated with the Windermere Club, offering a mix of luxury properties ranging from mid-six figures to well over a million dollars. Residents enjoy a peaceful, family-friendly atmosphere with strong community ties, proximity to downtown Windermere's quaint shops and dining, and convenient access to Orlando attractions, making it an idyllic escape that balances tranquility with Central Florida's vibrant lifestyle. ... Read more
Median Price: $1,258,250
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Real Estate News

Homes Just Sold That Attend Windermere High School: February 24th to March 2nd

Homes Just Sold That Attend Windermere High School: February 24th to March 2nd - March 3, 2026

The Windermere High School area had 12 sales during the week of Tuesday, February 24 to Monday, March 2, including including 10 single family homes for sale with an average ... continue reading
New Homes with In-ground Swimming Pools That Attend Windermere High School: February 22nd to February 28th

New Homes with In-ground Swimming Pools That Attend Windermere High School: February 22nd to February 28th - March 1, 2026

The Windermere High School area had new homes for sale with an in-ground swimming pool during the month of Sunday, February 22 to Saturday, February 28, including 2 single ... continue reading
New Homes For Sale This Week That Attend Windermere High School: February 20th to February 26th

New Homes For Sale This Week That Attend Windermere High School: February 20th to February 26th - February 27, 2026

The Windermere High School area had 9 new homes for sale during the week of Friday, February 20 to Thursday, February 26, including including 7 single family homes for sale ... continue reading
New Construction Homes For Sale This Week That Attend Windermere High School: February 18th to February 24th

New Construction Homes For Sale This Week That Attend Windermere High School: February 18th to February 24th - February 25, 2026

The Windermere High School area had only 1 new construction home during the week of Wednesday, February 18 to Tuesday, February 24, and it was a single family home for ... continue reading
Homes Just Sold That Attend Windermere High School: February 17th to February 23rd

Homes Just Sold That Attend Windermere High School: February 17th to February 23rd - February 24, 2026

The Windermere High School area had 10 sales during the week of Tuesday, February 17 to Monday, February 23, including including 8 single family homes for sale with an average ... continue reading
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