1998 to 2021Years built
3,000 to 6,100 sq ftHome size
GatedEntry
Summerport & SR 535Area
Why people move here

A gated circle of 32 custom homes on Lake Cawood.

Lake Cawood Estates is a small gated community of 32 custom homes on Lake Cawood, built between 1998 and 2021. Plans run from about 3,000 to over 6,000 square feet.
Windermere High and Publix at Cornerstone are both a short walk away, which is rare for an estate neighborhood.
Buyers who want a gate, the water and Windermere High a short walk away.

Lake Cawood Estates at a glance

Location: Winter Garden Vineland Road (SR 535) at Lake Cawood Drive

Builder: Custom and individual builders

Built: 1998 to 2021

Homes: 32 homesites

Home types: Custom single-family homes

Size: About 3,000 to 6,100 sq ft

Bedrooms: 4 to 6 bedrooms

Entry: Gated

Area: Summerport & SR 535

Life here

What Lake Cawood Estates has

🛡Gated entry
🌊Lake Cawood waterfront
Proximity

What is close to Lake Cawood Estates

  • Windermere High ~0.1 mi
  • Cornerstone at Summerport (Publix) ~0.2 mi
  • Winter Garden Village ~3 mi
  • AdventHealth Winter Garden ~3.5 mi

Approximate distances from the community entrance. Walt Disney World is roughly 10 to 15 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

🏫 Keene's Crossing Elementary

🏫 Bridgewater Middle

🏫 Windermere High

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

The numbers

Lake Cawood Estates market snapshot

Lake Cawood Estates 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 Lake Cawood Estates

Call or text me at 407.502.4719 and I will send every recent closed sale in and around Lake Cawood Estates, 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

Lake Cawood Estates homes for sale right now

Straight from Stellar MLS. Save the search and get new Lake Cawood Estates listings the day they hit.

Start of list of properties

Free guides

Buying or selling in Lake Cawood Estates?

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

🏡 Buyer Guide

How buying in Lake Cawood Estates 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

Lake Cawood Estates FAQ

Where is Lake Cawood Estates in Windermere?

Lake Cawood Estates is in the SR 535 corridor near Summerport, Windermere High and Windermere Prep, at Winter Garden Vineland Road (SR 535) at Lake Cawood Drive.

How far is Lake Cawood Estates from Walt Disney World?

Roughly 10 to 15 minutes off-peak from this part of Windermere. I will map the exact drive from the entrance before you choose.

When were homes in Lake Cawood Estates built?

1998 to 2021. Most homes were built by individual or custom builders.

What amenities does Lake Cawood Estates have?

Gated entry, Lake Cawood waterfront.

Is Lake Cawood Estates a gated community?

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

What schools serve Lake Cawood Estates?

Schools commonly listed for this community: Keene's Crossing Elementary, Bridgewater Middle, Windermere High. Assignments change, so verify zoning for a specific address with the OCPS School Locator.

Is Lake Cawood Estates 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 Lake Cawood Estates sell for?

Too few homes sold in Lake Cawood Estates 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 Lake Cawood Estates from Stellar MLS.

Your next step

Thinking about Lake Cawood Estates?

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

  • Recent closed sales in Lake Cawood Estates, 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.