Windermere 34786 · Butler Chain of Lakes

Isleworth Homes for Sale in Windermere, FL

A guard-gated community of custom estates on about 600 acres along the Butler Chain of Lakes, wrapped around the private Isleworth Golf & Country Club, with homes built mostly from the late 1980s through the 2000s and new custom builds still underway.

Written by Jared Jones Updated October 2026 Jared Jones Team, Brokered by eXp Realty

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Current Isleworth homes on the market.

$4,287,500Median sold price (12 months · 15 sales)
30 daysMedian days on market (CDOM); 6 of 15 closings show 0
1990 to 2004Typical year built (middle 50% of sales)

Stellar MLS sold data, closings Oct 31, 2025 through Aug 20, 2026 (export pulled Oct 14, 2026).

At a glance (as of October 2026)
FactFigure
Closed sales (last 12 months)15
Median sold price (last 12 months)$4,287,500 (15 sales)
Median price per sq ft$721
Median days on market30 days (CDOM); 6 of 15 closings show 0 days
Single-family median (sold)$4,125,000 (14 sales)
Typical year-built range1990 to 2004 (middle 50% of sales)
Active listings24 (Stellar MLS, Oct 14, 2026)
Legal subdivision namesIsleworth, Isleworth 01 Amd, Isleworth West
ZIP34786

Sources: Stellar MLS (sold closings last 12 months; export pulled Oct 14, 2026; closings in file run Oct 31, 2025 to Aug 20, 2026); Stellar MLS active listings (Oct 14, 2026); Stellar MLS listing records for Isleworth (community features and HOA).

Where is Isleworth in Windermere?

Isleworth is a guard-gated community of about 600 acres in the Windermere 34786 market, set on the Butler Chain of Lakes. The main gate is on Isleworth Country Club Drive, and the private Isleworth Golf & Country Club sits inside the community. Dr. Phillips dining and shopping are nearby, with I-4 and Apopka-Vineland Road close by for trips across Central Florida. Streets inside the gate include Isleworth Country Club Drive, Latrobe Drive, Deacon Circle, Lake Louise Drive, and Louise Cove Drive.

Location snapshot

  • ZIP: 34786
  • Area: Windermere, Orange County
  • Main gate: Isleworth Country Club Drive
  • Water: Butler Chain of Lakes
  • Size: about 600 acres

What’s around

  • Dining and shops: Dr. Phillips
  • Downtown: Town of Windermere
  • Roads: I-4, Apopka-Vineland Road
  • Theme parks: a short drive away
  • Schools: check Orange County Find My School by address

What amenities does Isleworth include?

Isleworth has a mandatory HOA, and recent listings show the dues cover the 24-hour guard gate and community security. The golf course, clubhouse dining, fitness, and tennis run through Isleworth Golf & Country Club, a private club whose 18-hole course was designed by Arnold Palmer and Ed Seay and opened in 1986. Club membership is separate from home ownership, so buying a home here does not include it. Every sold home and every active listing in the data recorded a private pool, and many lots sit on the Butler Chain. Ask us for the current HOA dues on any address you like.

Guard gate24-hour manned gate and community security
Golf clubPrivate Isleworth Golf & Country Club, separate membership
CourseArnold Palmer and Ed Seay design, opened 1986
LakesButler Chain of Lakes frontage on many lots
Private poolsRecorded on every home in the sold and active data
HOAMandatory HOA; we pull current dues per address

What do Isleworth homes typically look like?

Isleworth is a community of custom homes. Of the 15 sales in the last 12 months, 14 were single-family homes and 1 was a villa, built from 1987 to 2012. Heated living areas in that sample ran from 2,983 to 16,257 square feet with 3 to 7 bedrooms, and sold prices ranged from $2,745,000 to $11,500,000. The 24 active listings on October 14, 2026 were all single-family homes priced from $2,800,000 to $19,500,000, including three new custom builds dated 2026 and 2027. Treat these ranges as a guide to the sample, not a promise for a specific listing.

How does Isleworth compare to nearby Windermere options?

Buyers looking at Isleworth often also tour Keene’s Pointe homes for sale, another gated Windermere golf community, and compare lakefront estates across the wider Windermere market. Because the golf club is private and membership is separate, read Best Private Clubs in Orlando (2026) before you shop, and Orlando Gated Communities: Worth It? (2026) for the trade-offs of guard-gated living. Then use this page for active Isleworth inventory.

Winter Garden & Horizon West area overview. City-wide context, not Isleworth-specific. Watch when you want the bigger picture.

Video: Jared Jones Team / YouTube

Frequently asked questions

Where is Isleworth located?

Isleworth is a guard-gated community of about 600 acres in the Windermere 34786 market, on the Butler Chain of Lakes. The main gate is on Isleworth Country Club Drive, with Dr. Phillips, I-4, and Apopka-Vineland Road close by.

What do Isleworth homes sell for?

Across 15 closed sales in the last 12 months (closings from October 31, 2025 through August 20, 2026), the median sold price was $4,287,500, or $721 per square foot, with a median of 30 days on market. Six of the 15 closings show 0 days on market. Sold prices ranged from $2,745,000 to $11,500,000.

Does buying a home in Isleworth include golf club membership?

No. Isleworth Golf & Country Club is a private club, and membership is separate from home ownership. Buyers who want access to the course, clubhouse, and club amenities apply for membership on their own terms with the club.

Is Isleworth gated?

Yes. Isleworth has a 24-hour manned guard gate, and recent listings show the HOA dues cover the guard gate and community security.

How do I see current Isleworth homes for sale?

Use the live listings block on this page for active inventory, or call or text the Jared Jones Team at 407-706-5000. Stellar MLS showed 24 active Isleworth listings on October 14, 2026, and we can set an alert for new ones that match your criteria.

Browse nearby

Thinking about a home in Isleworth?

Call or text the Jared Jones Team at 407-706-5000. We will pull current comps, get HOA details on the homes you like, and arrange private showings through the gate.

About the author

Jared Jones

Jared Jones leads the Jared Jones Team, Brokered by eXp Realty, serving Windermere, Winter Garden, Horizon West, and Greater Orlando. Office: 504 W Plant Street, 1st and 2nd Floors, Winter Garden, FL 34787. Phone: 407-706-5000.

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