Isleworth Realty
Isleworth Realty is Orlando’s real estate expert for buying and selling luxury homes in Isleworth
Isleworth Realty is Orlando’s real estate expert for buying and selling luxury homes in Isleworth Golf & Country Club located in Windermere, FL. Building on our relationships with Tavistock Group and Christie’s International Real Estate, nobody works harder or has more resources to market and sell your home than Isleworth Realty.
02/06/2026
Celebrating a strong start to the year with more than $10M in sold and pending properties in January 2026. We’re proud to support our clients wherever their real estate goals take them, within the gates of Isleworth and beyond.
12/30/2025
JUST SOLD IN ISLEWORTH
Set along Isleworth’s 4th fairway and fully reimagined in 2019, this exquite golf-front estate offers modern design and refined living in one of the finest golf club communities in the world. Spanning more than 5,700 square feet of interior living space, the residence features 6 bedrooms and 8.5 baths, with exceptional living spaces and a sparkling pool overlooking the panoramic golf course views. Purchased at $4,400,000
09/05/2025
JUST SOLD IN ISLEWORTH
5271 Isleworth Country Club Drive
Purchased at $8,500,000
Nestled on a sprawling 1.17-acre lot originally hand selected by golf legend Arnold Palmer, this remarkable estate is perfectly positioned to capture breathtaking views of the first and tenth holes. Meticulously maintained, the grand residence encompasses 11,403 square feet of living space thoughtfully designed to provide both functionality and style.
08/12/2025
Isleworth estate tops Windermere sales from July 21 to 27 | West Orange Times & Observer The home at 9724 Chestnut Ridge Drive, Windermere, sold July 25, for $4,330,000.
08/01/2025
UNDER CONTRACT: Perfectly positioned to capture breathtaking views of the first and tenth holes, this remarkable estate provides a lifestyle of unmatched elegance and comfort. Meticulously maintained, this grand estate encompasses 11,403 square feet of living space thoughtfully designed to provide both functionality and style.
07/25/2025
Just Sold in Isleworth: Experience refined lakefront living in this exceptional estate, ideally located within the renowned Isleworth Golf & Country Club. Set along the shores of Lake Bessie on a beautifully landscaped 0.56-acre lot, the home spans 5, 557 square feet of luxurious living space. Purchased at $4,330,000
07/12/2025
Just Sold by IWR Realty. Nestled along the serene shores of Lake Sawyer within the highly desired Windermere community in Central Florida, this stunning property in Lake Sawyer Estates has been sold by Michelle Corbin of IWR Realty. Purchased at $1,400,000.
02/22/2025
Featured Friday Estate
9832 Laurel Valley Drive
6 Bedrooms | 7 Full Bathrooms | 3 Half Bathrooms | 11,100 Sq. Ft. | 0.60 Acre
Newly Offered at $10,475,000
Spanning 11,100 square feet of luxurious living space across three levels, this stunning property is perfect for those who seek the finest in lakefront living. The exquisitely remodeled estate offers a spectacular setting along the shores of Lake Butler and the famed Butler Chain of Lakes. Designed for both comfort and entertainment, the home offers an array of exceptional living spaces including six bedrooms, an entertainment lounge with full bar, a spacious theater room, a golf simulator and more.
01/24/2025
Featured Friday Estate
5518 Worsham Court
5 Bedrooms | 7 Full Bathrooms | 1 Half Bathrooms | 8,203 Sq. Ft. | 0.99 Acre
Offered at $6,650,000
Beautifully positioned along the back nine of Isleworth's renowned championship golf course, this expansive property spans more than 8,200 square feet of luxurious living space. Featuring a complete remodel with structural add-ons that have added over 2,000 square feet to the original footprint, the estate is a masterpiece of design and functionality, where every detail has been meticulously crafted to create the perfect family retreat.
https://youtu.be/abp8v0Nqke4
12/20/2024
Just Sold
5092 Isleworth Country Club Dr
$4,000,000
This exquisite estate sits along the front nine of Isleworth’s championship golf course, providing breathtaking views of the newly renovated Hole 6. Boasting 6,115 square feet of meticulous living space, this home ensures a seamless transition for its fortunate new owners.
12/20/2024
5190 Latrobe Drive
5 Bedrooms | 5 Full Bathrooms | 3 Half Bathrooms |7,191 sq. ft. | 0.73 acre
Located within the gates of the Isleworth Golf and Country Club community, this luxurious modern masterpiece is a superb build by Rial Jones with Jones Clayton Construction. The open floor plan with 30+ foot ceilings boasts large windows allowing plenty of natural light. The interior features have been thoughtfully designed by Wendy Kensler with Design Specifications. The estate includes top-of-the-line appliances and accessories such as Ultra-Aire Dehumidifiers, Control4 Smart Homes System, and Hunter Douglas Shades. The lush landscaping creates a private oasis on this oversized lot at 0.73 acres. Complete with a sparkling infinity pool and spa, featuring a Fyre Glass fireplace with remote control screens and a fully equipped outdoor kitchen. This unique state-of-the-art property is a contemporary showpiece with plenty of space to relax and entertain.
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Address
9350 Conroy Windermere Road
Windermere, FL
34786
Opening Hours
| Monday | 8:30am - 5:30pm |
| Tuesday | 8:30am - 5:30pm |
| Wednesday | 8:30am - 5:30pm |
| Thursday | 8:30am - 5:30pm |
| Friday | 8:30am - 5:30pm |
| Saturday | 9am - 4pm |