Isleworth Homes for Sale
Ultra-luxury 600-acre guard-gated golf community on the Butler Chain of Lakes.
Homes for sale in Isleworth
Inside Isleworth
Isleworth is a 600-acre guard-gated golf and country club community in Windermere, developed beginning in 1986. The subdivision comprises approximately 380 custom estate homes, predominantly ranging from 4,000 to 24,000 square feet, positioned along seven miles of well maintained Butler Chain of Lakes shoreline. Homes have appreciated 127 percent between 2015 and 2025, underscoring the community’s status as a perpetual seller’s market where luxury inventory remains scarce and strategically managed.
The centerpiece of Isleworth is the Arnold Palmer-designed championship golf course, originally laid out by Palmer and Ed Seay, later refined by course architect Steve Smyers. This 18-hole course is recognized as one of Florida’s most challenging layouts, accessible to residents and club members. The community also features an 89,000-square-foot clubhouse equipped with formal and casual dining venues, state-of-the-art fitness facilities, spa services, professional tennis courts, and a concierge team providing customized resident services. Twenty-four-hour manned security at the guard gate provides continuity and peace of mind.
School zoning within Isleworth varies by address, with elementary, middle, and high school attendance areas all administered by Orange County Public Schools. The community attracts professional athletes, CEOs, medical professionals, and entertainment figures seeking privacy and championship-level amenities. Notably, Isleworth carries no Community Development District (CDD) fees, a financial advantage unavailable in many newer luxury golf communities.
Current home prices range from $2.5 million to $14.25 million, with recent year-over-year activity reflecting seventeen home sales and an average selling price near $5.35 million. HOA fees range from $160 to $1,763 monthly, covering 24-hour guard-gated security, common area maintenance, private roads, cable TV, internet services, and escrow reserves. Club membership fees, which cover golf, clubhouse access, dining, tennis, and fitness facilities, are assessed separately and vary by membership tier. For buyers seeking to verify school zone assignment for a specific property address, Market Connect Realty agents can confirm current OCPS zoning before offer submission.
The facts
Frequently asked
What is the price range for homes in Isleworth?
Isleworth homes currently range from $2.5 million to $14.25 million. Recent market data from February 2026 shows an average asking price of $5.78 million and average selling price near $5.35 million. The wide range reflects varying lot sizes, waterfront proximity, and home square footage, which span from approximately 2,800 to 31,000 square feet.
Is Isleworth a gated community?
Yes. Isleworth is a guard-gated community with 24-hour manned security at the entrance. Continuous security patrols provide additional oversight. The gated status is a core feature of the community's controlled access and resident privacy, supported by deed restrictions and architectural review oversight.
What schools are zoned for Isleworth?
Isleworth properties are typically zoned to Orange County Public Schools, and the area has more than one middle school and high school zone depending on the address. Because Orange County zoning shifts block-by-block, verify the specific address with a Market Connect Realty agent before purchase.
What are the HOA fees in Isleworth?
HOA fees range from $160 to $1,763 monthly, covering 24-hour security, common area maintenance, private road upkeep, cable TV, internet, and reserves. Golf club membership fees, which provide course access and all clubhouse amenities, are separate and vary by membership category.
What amenities does Isleworth offer?
Isleworth features an Arnold Palmer-designed championship golf course, 89,000-square-foot clubhouse with formal and casual dining, state-of-the-art fitness center, spa services, professional tennis courts, community pool, private boat ramps, and dock facilities. An onsite concierge service coordinates customized resident services and recreational programming.
How many homes are in Isleworth?
Isleworth contains approximately 380 custom-built estate homes. The community was originally developed beginning in 1986 and continued building through 2023. The limited inventory and controlled development pace have contributed to strong appreciation and consistent buyer demand.
Is short-term rental allowed in Isleworth?
Short-term rental policies in Isleworth are governed by HOA deed restrictions and community guidelines. Details regarding rental duration and frequency restrictions are not publicly available. Contact a Market Connect Realty agent to confirm current rental policy and any owner approval requirements for your specific property.
What year was Isleworth developed?
Isleworth was originally developed beginning in 1986 and continued development through 2023. Early phases featured the Arnold Palmer golf course and initial estate home construction. The community's decades-long maturation has resulted in a stable, fully established neighborhood with established landscaping and amenities.