1986 to todayYears built
2,700 to 24,000+ sq ftHome size
Guard-gatedEntry
Butler Chain & TownArea
Why people move here

Central Florida's best-known guard-gated golf and lake community.

Isleworth wraps around Lake Butler, Lake Tibet, Lake Chase, Lake Louise and Lake Isleworth on the Butler Chain, with Lake Bessie on the other side. Inside the 24-hour gate: a private golf club, a tennis center, a clubhouse restaurant and concierge service.
Homes range from about 2,700 square feet to estates over 20,000. Restaurant Row is about four miles east, and the Lake Down boat ramp is right outside the gate.
Executives and athletes relocating who want privacy, golf and the chain in one address.

Isleworth at a glance

Location: Conroy-Windermere Road at Isleworth Country Club Drive, west of Apopka-Vineland Road

Builder: Custom and individual builders

Built: 1986 to today

Homes: About 360 homesites

Home types: Estate homes

Size: About 2,700 to 24,000+ sq ft

Bedrooms: 3 to 6+ bedrooms

Entry: Guard-gated

Area: Butler Chain & Town

Life here

What Isleworth has

🛡24-hour guard gate
⛳Isleworth Golf and Country Club
🏠Clubhouse and restaurant
🎾Tennis center
⚓Boat ramp and private docks
🗝Concierge
🛠Playground
Proximity

What is close to Isleworth

  • Lake Down boat ramp ~0.1 mi
  • The Grove (Publix) ~0.7 mi
  • R.D. Keene Park ~1.3 mi
  • Restaurant Row ~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

🏫 Windermere Elementary

🏫 Chain of Lakes Middle

🏫 Olympia High

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

The numbers

Isleworth market snapshot

$4,318,750Median sale priceDown 0.3% from $4,330,000 the year before.
34 daysDays on marketMedian cumulative days on market.
16Closed sales15 the year before.
95%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

Isleworth homes for sale right now

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

Start of list of properties

Free guides

Buying or selling in Isleworth?

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

🏡 Buyer Guide

How buying in Isleworth 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

Isleworth FAQ

Where is Isleworth in Windermere?

Isleworth is in the Town side of Windermere, near Lake Butler and Lake Down, at Conroy-Windermere Road at Isleworth Country Club Drive, west of Apopka-Vineland Road.

How far is Isleworth 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 Isleworth built?

1986 to today. Most homes were built by individual or custom builders.

What amenities does Isleworth have?

24-hour guard gate, Isleworth Golf and Country Club, Clubhouse and restaurant, Tennis center, Boat ramp and private docks, Concierge, Playground.

Is Isleworth a gated community?

Yes. Isleworth has a staffed guard gate. I confirm gate type and access rules for any home before you write an offer.

What schools serve Isleworth?

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

Is Isleworth 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 Isleworth sell for?

Per Stellar MLS, the median sale price in Isleworth was $4,318,750 across 16 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 Isleworth?

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

  • Recent closed sales in Isleworth, 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.