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Isleworth: Luxury Gated Community Chosen by the Rich & Famous in Florida

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Few communities in Florida can match Isleworth in prestige and desirability. Conceptualized by golf legend Arnold Palmer and home to some of the nation’s most influential athletes, entertainers, and entrepreneurs, Isleworth has the kind of provenance and history that elevate it above other Florida communities. Here’s what buyers should know about living in this affluent enclave.

Table of Contents

About Isleworth

Isleworth, Florida is a gated community offering luxury real estate. With an estimated population of just 900 and a limited selection of finely crafted homes, it is one of the most desirable places to live in the Windermere area.


Once Florida’s citrus bowl, the community was formerly known as the “Isle of Worth” to reflect its bountiful nature. Founders Joshua and Sydney Chase built their citrus company on the land in 1884 due to a severe frost and scarce supply in Sanford. The name would be shortened to Isleworth later on. The first residents were Sydney, who built a bungalow in the area in 1913, and his son Frank, who moved to Isleworth in 1935 with his wife Helen.

Arnold Palmer purchased land in Isleworth in 1984 with plans of developing a community. The community would offer luxury real estate and upscale amenities with the jewel being a private 18-hole golf course. Palmer partnered with The Concord Corporation of San Antonio for the project before selling to Aviva Land Holdings in 1993.

Aviva Land Holdings redeveloped the 600-acre community to include estate-style homes. The community was marketed with the tagline “Only The Best” to reflect its luxuriousness and exclusivity. Today, Isleworth, Florida is one of the most desirable places to live in the Sunshine State, offering lake views and privileged access to world-class amenities.


The community is nestled along the shores of the Butler Chain of Lakes, in the southwest suburb of Windermere. It is located in Orange County in Central Florida giving residents access to Downtown Orlando and some of Florida’s finest beaches. It encompasses roughly 0.9 square miles. The nearest major airport is the Orlando International Airport.

What it’s known for

Field Casual Clothing couple

Isleworth is known for world-class golf amenities. It is one of the most prestigious golf communities in Central Florida attracting golf enthusiasts and professional athletes from all over the country.

Other than golf, the community also offers tennis and water-based activities. Its unique lakeside setting makes it ideal for those who enjoy nature and the outdoors. It offers the best of resort-style living set amidst Florida’s tropical sun-drenched landscape.

With gated and guarded entrances, the community is also one of the most exclusive areas in Windermere. Residents enjoy a safe environment where they can live their most enjoyable life among like-minded people.

Luxury homes for sale in Isleworth, Florida are more than trophy properties. These homes are known for excellent craftsmanship and timeless designs. The community works with some of the nation’s most reputable luxury builders to maintain the highest levels of quality.

Isleworth Country Club homes for sale

Architecture Balcony Caribbean

Overview of the market

Price range, property types, architectural styles

The housing market offers an excellent selection of single-family homes. Vacant land is also available. Luxury homes for sale in Isleworth, Florida are expansive, offering thousands of square feet of living space along with oversized garages, spacious driveways, and landscaped gardens.

The most coveted homes and vacant lots are located along the waterfront and the golf course. Popular architectural styles include Mediterranean, Spanish Revival, Italianate, and Contemporary. The homes in the community were designed to blend seamlessly into Central Florida’s scenic landscape.

Home prices in Isleworth, Florida can easily go up to seven figures, ranging from $1.2 million to upwards of $4 million. Homeowners association (HOA) fees can cost anywhere from $1,500 to $1,659 per quarter. However, buyers are more than willing to pay a premium for a home in this private community as evidenced by the number of high-profile individuals who have owned property in Isleworth.

There is a high demand for property in this affluent community with only a few active listings at any given time, since many homeowners prefer to hold onto their properties whether for personal use or rental opportunities.

The Isleworth lifestyle

Isleworth has mastered the art of casual elegance with finely crafted homes and well-maintained facilities. Residents enjoy a relaxed lifestyle with easy access to golf and tennis facilities, gleaming lakes, and lush gardens. There is an emphasis on wellness with fitness classes and outdoor recreation. Although the community has a serene environment, residents are never too far from the action, with access to Downtown Orlando’s bars, clubs, and restaurants.

Notable community features and amenities

Aspirations Balance Beach

Isleworth residents enjoy a high quality of life with peaceful surroundings, beautiful scenery, and exclusive access to world-class recreational facilities. Many of the activities in the community revolve around the Butler Chain of Lakes as well as a well-appointed clubhouse with Mediterranean-style architecture.

Some of the community’s amenities include:

    • Isleworth Country Club — The country club ranks among the Top 100 Platinum Clubs of the World for its exceptional facilities and services. The clubhouse spans 89,000 square feet and has over 200 staff members and service providers to create an unparalleled experience for all members. The clubhouse hosts socials and events where residents can meet and get to know other members of the community.


    • Fitness center and spa —Located within the clubhouse, the fitness center features high-end cardio and strength training equipment. It also offers fitness classes and personal training to help members stay on top of their fitness goals. The spa provides skin treatments and body massages.


    • Infinity edge pool—Club members have access to a stunning infinity-edge resort-style pool with views of Lake Louise as well as a children’s splash pad for the younger kids. For adults, the poolside area features daybeds and a poolside bar and grill, which is perfect for laid-back gatherings.


    • Tennis Center —Players of all skill levels can play tennis and racquet at the Tennis Center, which features a Plexi Cushion court, a multi-sport court, a padel court, six Har-Tru clay courts, and private locker rooms. The center offers programs ranging from basic to intermediate.


    • Lake Louise and the Butler Chain of Lakes — The community provides access to roughly seven miles of pristine shoreline. Residents can enjoy a variety of water-based activities, including swimming, fishing, boating, paddle boarding, and waterskiing. Club members have access to private docks with direct access to the lakes surrounding the community.


    • On-site dining —The clubhouse offers exciting culinary experiences with a team of chefs and seasonal menus inspired by different cultures around the world. Its kitchen staff are trained to very high standards and use organic produce and seasonal ingredients to create exquisite dishes.


    • Youth programs and family activities —The community organizes seasonal and year-round activities for families and youth. These include summer camp, after school programs, and holiday celebrations. Camp Isleworth is a renowned summer camp that helps young persons meet new people and hone skills.

Schools, activities and attractions near Isleworth, Florida

Schools serving Isleworth residents include:

  • Windermere Elementary
  • Windermere Prep
  • Chain of Lakes Middle School
  • Olympia High School

Nearby shops and service providers include:

  • Nemours Children’s Primary Care
  • Sanctuary Spa
  • Walmart
  • Publix
  • Luv-N-Care Animal Hospital of Windermere
  • Windermere Branch Library

Located just outside Orlando, the community offers access to renowned Florida attractions such as:

  • Walt Disney World Resort
  • Universal Orlando Resort
  • Magic Kingdom
  • Epcot
  • SeaWorld Orlando

Contact Central Florida Realtors for more insider information on attractions in and around Isleworth.

Membership information

Aside from HOA fees, club members need to pay one-time and ongoing fees for privileged access to the clubhouse and its services and amenities. These fees include:

  • Golf membership initiation fee — Starts at $100,000 and up
  • Monthly golf dues —Starts at $2000 and up
  • Social membership initiation fee — $20,000
  • Monthly social dues — $750

Take note that fees are subject to change. Visit the Isleworth website for updates and information. Consult with a luxury real estate professional for advice on HOA and membership fees.

Buyers can also check The Golden Bear Club in Windermere. The club features a Jack Nickaus-designed golf course, a luxurious clubhouse, and other upscale amenities.

Where to live in Isleworth

Architecture Backgrounds Beauty In Nature

Gardens of Isleworth (Alexandra Garden Court, Aviva Garden Court, Isleworth Garden Drive, and Joanna Garden Court)

The Gardens of Isleworth is the newest section of the community. The area offers a small selection of custom built homes by luxury builder Goehring & Morgan. Prevalent architectural styles include Spanish Revival, Island Caribbean, Dutch Colonial, and Contemporary.

Designed with estate-style living in mind, the area has gardens, professional landscaping, and water features. Most homes vary in size from approximately 3,600 to 6,500 square feet. Home prices can go up to seven figures.

Isleworth Country Club Drive

There are approximately 15 homes to the south of this street and they are located along the golf course. These homes command golf course views, particularly the 1st, 10th, 17th, and 18th holes. Property sizes range from over 3,000 to 8,800 square feet. Many of the homes in this part of the community were built between 1986 and 2003.

Isleworth Country Club Drive to Monterey Club Court

Buyers will find a handful of waterfront homes on the northern edge of Isleworth Country Club Drive, including a few waterfront homes located on the pond in Monterey Club Court. Property sizes range from more than 4,100 to 12,000 square feet. Many of the homes in this area were built between 1990 and 2004.

There is also a limited selection of non-waterfront homes ranging from approximately 3,600 to 11,000 square feet in size. The majority of these homes were constructed sometime between 1988 and 1996.

Isleworth Country Club Road

Buyers can choose from a fine selection of golf course properties overlooking the 3rd, 4th, 5th, 6th, 7th, and 8th holes. Some homes have views of Lake Bessie. The homes in this area offer roughly 3,000 to more than 11,000 square feet. Many of these homes were built between 1987 and 2006.

Isleworth Country Club Drive to Laurel Valley Drive and Worsham Court

The most coveted homes in the area are located on the Lake Butler side. Property sizes range from approximately 4,800 to 14,100 square feet. Home prices in this area can go up to seven or eight figures.

Eastern section (Louise Cove Drive to Cypress Chase Drive)

The eastern section of the community has about 25 home sites and is nestled on the eastern banks of scenic Lake Louise. The main entrance to this section can be found on the east side of Chase Road, just across the entrance to Lake Butler Sound.

The housing here is divided between lakefront and non-lakefront homes of varying sizes. Most homes in this part of town are newer construction, having been built between 2000 and 2014. The majority of lakefront homes were constructed between 2002 and 2008.

Non-lakefront homes span from 4,000 to over 8,000 square feet while lakefront properties typically offer 5,000 to more than 9,000 square feet of living space.

Lake Louise Drive to Walzer Court and Walzer Way

To the right of Isleworth Country Club Drive lies Lake Louise Drive followed by Walzer Court and Walzer Way. This area offers several golf course properties, some of which command views of the 16th and 17th holes. These homes range in size from 6,000 to nearly 8,000 square feet. The majority of the properties here were built between 2002 and 2005.

There are also more than a dozen waterfront homes and homesites on Lake Louise. These properties range in size from 4,000 to over 21,500 square feet. Many of the homes here were constructed between 1989 and 2011.

Fairway Oaks Drive to Wentworth Court

Many of the homes in this part of the community were constructed between 1990 and 2006. Most homes offer roughly 3,700 to over 7,700 square feet of living space. The most coveted homes are the waterfront properties along Lake Bessie, a 164-acre body of water. These lakefront homes offer more space than non-lakefront homes, ranging from 4,000 to over 15,000 square feet in size and were built between 1991 and 2015.

Payne Stewart Drive, Lake Isleworth Court, Green Island Cove, Deacon Court, and Deacon Circle

This area offers an excellent selection of lakefront homes along Lake Chase, Lake Isleworth, and Lake Louise. These properties offer roughly 2,600 to over 15,300 square feet of living space. Most of the housing stock was built between 1986 and 2012. There are also several non-lakefront homes offering about 2,700 to 3,400 square feet of living space. Many of these homes were constructed between 1987 and 1999.

McCormick Place

This area offers a limited selection of homes varying in size from 4,800 to more than 7,200 in size. Most of the homes here were constructed between 1987 and 1997.

Chestnut Ridge Drive, Latrobe Drive, and Vardon Drive

There is a good mix of waterfront and non-waterfront homes in this area. Property sizes vary from about 3,200 to 11,300 square feet. Many of the homes here were built between 1986 and 2009.. Waterfront properties are either located on Lake Bessie or on ponds.

With so many desirable areas in the community, choosing is truly the hard part. Talk to a luxury real estate professional for in-depth information on luxury homes for sale in Isleworth, Florida.

The who’s who of Isleworth

Isleworth, Florida attracts high net worth individuals and public figures due to its exclusivity and privacy. The community has been home to several professional athletes, including Tiger Woods, Mark O’Meara, Charles Howell, Stuart Appleby, Robert Allenby, Vince Carter, and Shaquille O’Neal.

The affluent suburb of Windermere has been home to many high-profile individuals, including baseball player Johnny Damon, Westgate founder David Siegal, Creed guitarist Mark Tremonti, NFL players Devon Hester and Derrick Mason, and actors Morgan Freeman and Wesley Snipes.

The members of 90s pop acts the Backstreet Boys and N’Sync also lived in Windermere with former manager Lou Pearlman.

Needless to say, Isleworth residents are no strangers to fame and success. Many are drawn to the community for the privacy and security it offers.

Isleworth, Florida is calling

Count yourself among Isleworth’s affluent residents and start enjoying the luxury resort lifestyle. Listed Luxury/Coldwell Banker Global Luxury is here to help you find the perfect home. Call our Central Florida Realtors at 407.620.8597 or send an email to Frank(at)ListedLuxury(dotted)com to get started. Our company is led by Frank Benevento, a luxury real estate professional with 21 years of experience. Frank is the #1 single agent in Seminole County for 2020 with more than $35 million in sales.

Friendly but professional, we help clients navigate the world of luxury listings, we also help with paperwork, HOA and club membership fees. We’re a detail-oriented, client-focused real estate company offering first-rate service in Isleworth, Orlando, Winter Park, and Lake Mary.