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Isleworth, Windermere FL. 600 guard-gated acres on the Butler Chain of Lakes, median sale price $4,998,261. Market data, the club, schools by address, and discreet representation from Adams Equities.
Isleworth is a guard-gated community of approximately 600 acres in Windermere, Orange County, Florida, on the Butler Chain of Lakes. It is built around the Isleworth Golf & Country Club and is the highest-priced residential community in the Orlando metropolitan area by median sale price.
The Butler Chain is thirteen interconnected lakes holding more than 5,000 acres of surface water, and in 1985 it became the first lake system in Florida designated Outstanding Florida Waters. Isleworth carries over seven miles of shoreline with private members-only docks.
Frontage on the larger open lakes, frontage on the smaller connected lakes, and cove or canal access that reaches the main water each price differently. Two homes a hundred yards apart can sit on very different water.
The course opened for play in 1986 to an Arnold Palmer and Ed Seay design and was reworked by Steve Smyers in 2003-04. It plays par 72 at roughly 7,544 yards from the championship tees. The 89,000-square-foot Mediterranean clubhouse carries a fitness centre, a spa, several restaurants and event space, alongside six Har-Tru clay courts, one Plexi Cushion court and a padel court.
Memberships are by invitation only and the club states that a waiting list is currently in place. The club does not publish whether membership conveys with a home purchase, so it should be established during diligence rather than assumed.
School assignment splits inside the community, which most published guides to Isleworth get wrong. Elementary is Windermere Elementary across the addresses tested. Isleworth Country Club Drive and Isleworth Gardens Drive fall to Chain of Lakes Middle and Olympia High; southern streets such as Louise Cove Drive fall to Bridgewater Middle and Windermere High. Checked against the Orange County Public Schools 2026-27 attendance-zone layer on 17 August 2026.
Median sale price for the three months ending June 2026 was $4,998,261 at $784 per square foot, with a median 40 days on market. The median rests on three June sales and should be treated as directional. Days on market moved from 179 a year earlier to 40 with price flat.
Keene's Pointe trades at $467 per square foot against Isleworth's $784. Recent closings: 5525 Isleworth Country Club Drive at $11,500,000 in May 2026, 5271 Isleworth Country Club Drive at $8,500,000 in September 2025, 9310 Isleworth Gardens Drive at $3,550,000 in November 2025, and 4711 Joanna Garden Court at $2,950,000 in February 2026.
The median sale price was $4,998,261 for the three months ending June 2026, at $784 per square foot (Redfin, retrieved 17 August 2026). That median rests on a small number of sales, so treat it as directional. Recent closings run from roughly $2.95 million to $11.5 million, and the community holds Central Florida's single-family record at $35,000,000, set in February 2023.
Not automatically. Isleworth Golf & Country Club states that memberships are by invitation only and that a waiting list is currently in place. The club does not publish whether membership conveys with a home purchase, so it should be established during diligence rather than assumed.
Assignment splits inside the community. Elementary is Windermere Elementary across the addresses tested, but Isleworth Country Club Drive and Isleworth Gardens Drive fall to Chain of Lakes Middle and Olympia High, while southern streets such as Louise Cove Drive fall to Bridgewater Middle and Windermere High. Checked against the Orange County Public Schools 2026-27 attendance-zone layer on 17 August 2026. Zones are redrawn periodically; confirm per address.
Yes. Isleworth has 24-hour guarded gates with concierge services across approximately 600 acres on the Butler Chain of Lakes.
Arnold Palmer and Ed Seay. The course opened for play in 1986 and was reworked by Steve Smyers in 2003-04. It plays par 72 at roughly 7,544 yards from the championship tees.
Isleworth is in Windermere, Orange County, Florida, on the Butler Chain of Lakes. It is roughly 13 miles by road from Magic Kingdom, 15 miles from downtown Orlando, and 20 miles from Orlando International Airport.
Adams Equities — boutique luxury real estate brokerage. Office: 9100 Conroy Windermere Road, Suite 200, Windermere, FL 34786. Phone: +1 407-448-3757. Edgar Adams, Founder & Managing Broker. Alexander Adams, Principal & Market Strategist.
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