2001 to 2005Years built
2,350 to 4,350 sq ftHome size
GatedEntry
LennarBuilder
Why people move here

Gated Mediterranean homes between Gotha and Windermere.

Windsor Landing is a gated Lennar community from 2001 to 2005 on Maguire Road, between Gotha and Windermere. Every home has at least four bedrooms, with two and three car garages.
Freedom Park is about half a mile away and downtown Windermere is about two miles. It is a south Ocoee address with a Windermere-side feel.
Upsizers who want four bedrooms or more and a Windermere-adjacent address.

Windsor Landing at a glance

Location: Maguire Road at Sagecrest Drive, with a second entrance at Thornebrooke Drive

Builder: Lennar

Built: 2001 to 2005

Homes: 215 homes

Home types: Single-family homes

Size: About 2,350 to 4,350 sq ft

Bedrooms: 4 to 5 bedrooms

Entry: Gated

Area: South Ocoee & Maguire Road

Life here

What Windsor Landing has

🛡Gated entry
⚓Fishing dock
🛠Playground
🏀Basketball court
🏛Mediterranean-style architecture
Proximity

What is close to Windsor Landing

  • Freedom Park ~0.5 mi
  • Plantation Grove (Publix) ~1 mi
  • Downtown Windermere ~2 mi
  • SR 50 shopping ~2 mi

Approximate distances from the community entrance. Walt Disney World is roughly 20 to 25 minutes away off-peak. SR 50, Clarke Road and Maguire Road back up 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 Landing market snapshot

$750,000Median sale priceLast 12 months.
24 daysDays on marketMedian cumulative days on market.
8Closed sales8 the year before.
98%Sale-to-list price ratioMedian for the last 12 months.

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 Landing homes for sale right now

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

Start of list of properties

Free guides

Buying or selling in Windsor Landing?

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

🏡 Buyer Guide

How buying in Windsor Landing 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 Landing FAQ

Where is Windsor Landing in Ocoee?

Windsor Landing is in south Ocoee along the Maguire Road corridor, at Maguire Road at Sagecrest Drive, with a second entrance at Thornebrooke Drive.

How far is Windsor Landing from Walt Disney World?

Roughly 20 to 25 minutes off-peak from this part of Ocoee. I will map the exact drive from the entrance before you choose.

When were homes in Windsor Landing built?

2001 to 2005, by Lennar.

What amenities does Windsor Landing have?

Gated entry, Fishing dock, Playground, Basketball court, Mediterranean-style architecture.

Is Windsor Landing a gated community?

Yes. Windsor Landing has a gated entry. I confirm gate type and access rules for any home before you write an offer.

What schools serve Windsor Landing?

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 Landing inside Ocoee city limits?

Most Ocoee neighborhoods are inside city limits, but some homes with an Ocoee, Apopka, Winter Garden or Orlando mailing address sit in unincorporated Orange County. Taxes, utilities and services differ, so I confirm the jurisdiction for every address.

What do homes in Windsor Landing sell for?

Per Stellar MLS, the median sale price in Windsor Landing was $750,000 across 8 closed sales in the 12 months ending September 30, 2026. Call or text me at 407.502.4719 for recent sales that match your home.

Your next step

Thinking about Windsor Landing?

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

  • Recent closed sales in Windsor Landing, straight from Stellar MLS
  • City or county, HOA and CDD 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 city 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.