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Illustrative estate-home streetscape with mature oak trees, landscaped lawns and spacious homes set back from a gently curving road.

Windermere, Florida

Isleworth Homes for Sale

Explore estate homes in a private golf-club community among the Butler Chain of Lakes. Discover the setting and local life as you consider a primary residence or second home.

Windermere, Florida

Explore Isleworth homes for sale in Windermere, Florida, one of Central Florida’s most prestigious private golf communities. Set among the Butler Chain of Lakes, Isleworth is known for its exceptional luxury homes, expansive lakefront estates, championship golf and beautifully maintained surroundings. Properties range from elegant custom residences to substantial waterfront estates with private docks, pools and impressive outdoor living spaces. At Top Villas Realty, we help buyers understand the differences between Isleworth’s locations, lots and individual homes, from golf-course and water views to privacy, property size and long-term ownership considerations. Browse the latest Isleworth real estate for sale below, with our local insight to help you identify the homes that best match what you’re looking for.

Top Villas Intelligence

Know what a home will earn before you buy

Create a free account to see projected rental revenue, ownership costs and operating yield on every eligible listing.

Sample: $118,400 gross rental revenue at 74% projected occupancy, $61,900 operating income and a 7.2% operating yield, with high confidence.

Isleworth Property Market at a Glance

Review property counts, current homes for sale and the median asking price alongside individual listings.

Homes in community
485
For sale now
24
Median list price
$5,149,750

Rental figures are modelled from comparable nightly rates and are not a guarantee of income.

Estate Homes in an Established Lake Setting

Isleworth spans 600 acres among the Butler Chain of Lakes, with estate homes framed by mature oak and cypress trees. Landscaped streets and outdoor sculpture give the community a distinctive residential character, while golf-course and shoreline settings offer different outlooks to consider when comparing properties. The Gardens of Isleworth adds a custom-home enclave with designs by Goehring & Morgan. For a primary residence or second home, the choice is about more than the broader lake setting: consider how a particular home’s layout, outdoor spaces and position suit the way you live. Views, frontage and other features belong to individual properties, so use each sale listing to understand what a home actually offers.

Illustrative lake setting inspired by Isleworth in Windermere, Florida, with estate homes nestled among mature oaks, cypress trees and landscaped grounds.

Golf and the Clubhouse Setting

Isleworth’s 18-hole championship golf course anchors the community’s club-centered setting. Created by Arnold Palmer and enhanced by Steve Smyers in 2003, the course features rolling terrain and large, undulating greens. For buyers who enjoy golf, its design is an important part of understanding the community beyond the homes themselves. The 89,000-square-foot Mediterranean-style clubhouse serves as the center of club activity, bringing member dining, fitness and social spaces into the same setting. Together, the course and clubhouse help define Isleworth’s character, but they remain club facilities: purchasing a home does not automatically grant access.

Club Facilities for Recreation and Social Life

Club facilities support exercise, family activities and time outdoors in a community with more than seven miles of shoreline.

  • Fitness and Spa

    A fitness center, exercise classes, personal training and spa treatments give members options for regular workouts and time to unwind.

  • Racquet Sports

    Six Har-Tru clay courts, one Plexi Cushion court, a padel court and a multi-sport court offer members several ways to make racquet sports part of the week.

  • Poolside on Lake Louise

    The clubhouse pool overlooks Lake Louise, pairing an infinity edge with a children’s splash pad for swimming and family recreation through the club.

  • Dining and Youth Activities

    Member dining and a poolside bar and grill complement after-school activities, seasonal celebrations and Camp Isleworth, supporting a social club routine.

  • Recreation on the Lakes

    Private members-only docks serve interconnected lakes for boating, fishing, paddleboarding and waterskiing; they are distinct from an individual home’s dock.

Everyday Life Around Windermere

Public facilities around Windermere add another dimension to everyday life beyond the private club. The Windermere library branch at 530 Main Street offers public computers, Wi-Fi, printing, a language-learning lab and children’s programming. These services can support practical errands, personal interests and family routines whether you live in the area year-round or use your home seasonally. On Fridays, the town’s farmers market at Town Square Park, 520 Main Street, brings together produce, seafood, baked goods, flowers and handmade goods. A library visit or market stop offers a way to participate in local life. Consider these public resources alongside the home itself and any club activities you hope to pursue.

Recently sold here

11 homes sold nearby in the last 12 months · median $2,600,000

Where Isleworth is located

485 homes · 1.1 sq mi

Gaby Sadler, Property Specialist

Gaby Sadler

Property Specialist, Serhant

Talk to Gaby before you buy

I can arrange viewings, answer your questions and prepare a personalized rental projection for any home you're considering.

Questions About Buying in Isleworth

Find Your Home in Isleworth

Begin with the properties for sale, then compare the details that will shape your time at home. You may prioritize a particular outlook, a layout that accommodates visiting family or outdoor spaces suited to your daily routine. For a primary residence or second home, weigh those property-specific features alongside Isleworth’s established landscape and the wider Windermere setting. Keep club membership as a separate consideration so your shortlist reflects both the home you want and the activities that matter to you.

Explore homes for sale in Isleworth