1990 to 2013Years built
2,400 to 9,600+ sq ftHome size
4 to 7 bedroomsBedrooms
Gotha & Dr. Phillips SideArea
Why people move here

Estate homes and tennis courts off Windy Ridge Road.

Windsor Hill is about 100 estate homes from 1990 to 2013 on Windy Ridge Road, with four to seven bedrooms and some homes over 9,000 square feet.
A park, tennis courts and a playground are shared. The Grove and Gotha Park are each about two miles away.
Upsizers who want an estate home with room for everyone.

Windsor Hill at a glance

Location: Windy Ridge Road at Windsor Hill Drive

Builder: Custom and individual builders

Built: 1990 to 2013

Homes: About 100 homes

Home types: Estate homes

Size: About 2,400 to 9,600+ sq ft

Bedrooms: 4 to 7 bedrooms

Area: Gotha & Dr. Phillips Side

Life here

What Windsor Hill has

🌳Community park
🎾Tennis courts
🛠Playground
🌊Butler Chain access for select homes
Proximity

What is close to Windsor Hill

  • Gotha Park ~2 mi
  • The Grove (Publix) ~2 mi
  • Downtown Windermere ~3 mi
  • Isleworth Golf and Country Club ~4 mi

Approximate distances from the community entrance. Walt Disney World is roughly 15 to 20 minutes away off-peak. Two-lane roads around the lakes and SR 535 slow down at rush hour, so send me your work address and I will map your real commute.

Schools

🏫 Thornebrooke Elementary

🏫 Gotha Middle

🏫 Olympia High

Orange County Public Schools. Zoning changes, so verify every address.

The numbers

Windsor Hill market snapshot

Windsor Hill had 2 closed sales in the last 12 months. That is too few for a median that means anything, so I price homes here one at a time.

Get the real numbers for Windsor Hill

Call or text me at 407.502.4719 and I will send every recent closed sale in and around Windsor Hill, straight from Stellar MLS, with what each one tells us about value.

Stellar MLS, residential closed sales, 12 months ending September 30, 2026. Pulled Oct 15, 2026 and refreshed every quarter. Deemed reliable but not guaranteed. For a specific home, request a custom report.

Live MLS listings

Windsor Hill homes for sale right now

Straight from Stellar MLS. Save the search and get new Windsor Hill listings the day they hit.

Start of list of properties

Free guides

Buying or selling in Windsor Hill?

Pick your guide, tell me where to send it, and it opens right away.

🏡 Buyer Guide

How buying in Windsor Hill works, from new construction versus resale to what to verify on HOA, CDD and school zoning.

🔑 Seller Guide

Pricing, prep and timing for selling your current home, including how to sell and buy at the same time without moving twice.

Questions buyers ask

Windsor Hill FAQ

Where is Windsor Hill in Windermere?

Windsor Hill is in the Gotha and Dr. Phillips side of Windermere, west of Apopka-Vineland Road, at Windy Ridge Road at Windsor Hill Drive.

How far is Windsor Hill from Walt Disney World?

Roughly 15 to 20 minutes off-peak from this part of Windermere. I will map the exact drive from the entrance before you choose.

When were homes in Windsor Hill built?

1990 to 2013. Most homes were built by individual or custom builders.

What amenities does Windsor Hill have?

Community park, Tennis courts, Playground, Butler Chain access for select homes.

Is Windsor Hill a gated community?

Windsor Hill is not listed as gated. Ask me about gated options nearby.

What schools serve Windsor Hill?

Schools commonly listed for this community: Thornebrooke Elementary, Gotha Middle, Olympia High. Assignments change, so verify zoning for a specific address with the OCPS School Locator.

Is Windsor Hill in the Town of Windermere?

Many Windermere addresses are in unincorporated Orange County, not the Town. Taxes, rules and services differ, so I confirm the jurisdiction for every address.

What do homes in Windsor Hill sell for?

Too few homes sold in Windsor Hill in the last 12 months for a reliable median. Call or text me at 407.502.4719 and I will send recent closed sales in and around Windsor Hill from Stellar MLS.

Your next step

Thinking about Windsor Hill?

Give me 30 minutes and tell me your timeline. I will send back:

  • Recent closed sales in Windsor Hill, straight from Stellar MLS
  • Town or county, HOA and lake access for the homes that fit
  • Your real commute, mapped from the entrance

No pressure. If you are selling a home somewhere else first, we will plan both sides together.

Semper Fi to your real estate needs. Jorge Martinez, REALTOR®

Information deemed reliable but not guaranteed. Community details come from public sources and change over time; distances are approximate. Market data from Stellar MLS. Buyers should verify Town or county jurisdiction, school assignments, HOA, CDD, lake access and all property details independently. The JEM Property Group is an independently owned and operated real estate team affiliated with Keller Williams Realty. Equal Housing Opportunity.