2013 to 2019Years built
3,100 to 6,900 sq ftHome size
GatedEntry
Toll BrothersBuilder
Why people move here

Gated Toll Brothers homes on half-acre lots.

Casabella is a gated Toll Brothers community of 79 homesites on McKinnon Road, built from 2013 to 2019. Half-acre lots and five to seven bedroom plans make it one of the roomiest newer neighborhoods in Windermere.
A private park sits inside the gate. Winter Garden Village and Publix are each about two miles away.
Upsizers who need serious bedroom count on a big lot.

Casabella at Windermere at a glance

Location: West Lake Butler Boulevard at McKinnon Road

Builder: Toll Brothers

Built: 2013 to 2019

Homes: 79 homesites

Home types: Single-family homes on half-acre lots

Size: About 3,100 to 6,900 sq ft

Bedrooms: 5 to 7 bedrooms

Entry: Gated

Area: McKinnon & Maguire Road

Life here

What Casabella at Windermere has

🛡Gated entry
🏡Half-acre homesites
🌳Private community park
Proximity

What is close to Casabella at Windermere

  • Cornerstone at Summerport (Publix) ~2 mi
  • Winter Garden Village ~2.3 mi
  • AdventHealth Winter Garden ~3 mi
  • Roper YMCA ~4 mi

Approximate distances from the community entrance. Walt Disney World is roughly 20 to 25 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

🏫 Windermere Elementary

🏫 Bridgewater Middle

🏫 Windermere High

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

The numbers

Casabella at Windermere market snapshot

$3,037,500Median sale priceLast 12 months.
118 daysDays on marketMedian cumulative days on market.
6Closed sales2 the year before.
94%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

Casabella at Windermere homes for sale right now

Straight from Stellar MLS. Save the search and get new Casabella at Windermere listings the day they hit.

Start of list of properties

Free guides

Buying or selling in Casabella at Windermere?

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

🏡 Buyer Guide

How buying in Casabella at Windermere 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

Casabella at Windermere FAQ

Where is Casabella at Windermere in Windermere?

Casabella at Windermere is in the McKinnon Road and Maguire Road side of Windermere, toward Winter Garden, at West Lake Butler Boulevard at McKinnon Road.

How far is Casabella at Windermere from Walt Disney World?

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

When were homes in Casabella at Windermere built?

2013 to 2019, by Toll Brothers.

What amenities does Casabella at Windermere have?

Gated entry, Half-acre homesites, Private community park.

Is Casabella at Windermere a gated community?

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

What schools serve Casabella at Windermere?

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

Is Casabella at Windermere 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 Casabella at Windermere sell for?

Per Stellar MLS, the median sale price in Casabella at Windermere was $3,037,500 across 6 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 Casabella at Windermere?

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

  • Recent closed sales in Casabella at Windermere, 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.