Tour
#O6315165, Ayoub Aitelhaj, Listing office: THE SIMON SIMAAN GROUP
$14,250,000 List price
5525 Isleworth Country Club Dr Windermere, FL 34786
5 beds
5 full, 1 partial
9,511 sqft
1.0 acres
$1,498 / sqft
House
Property details
About 5525 Isleworth Country Club Dr
Exceptional in both style and scale, this extraordinary Isleworth estate represents the pinnacle of luxury living in one of the finest golf club communities in the world. Designed by architect Terry Irwin and built by Ballard Construction, with interior designs by Faith Fournet, the property has been fully transformed and thoughtfully curated over the last three years to deliver exceptional comfort, sophistication and panache at every turn. The two-story estate is set on a pristine 1.02-acre golf-front home site along Isleworth's famed championship golf course and from the moment you enter, you'll be captivated by the artistry in design and modern innovation. The interiors span more than 9,500 square feet living and 13,000 under roof, blending 5 bedrooms, 5.5 baths and an array of indoor and outdoor living areas with uncompromisingly luxurious finishes designed for effortless entertaining and quiet moments alike. At the heart of the home, the showstopping glass-enclosed wine room—temperature-controlled and with a 2,400-bottle capacity—is a collector's dream and the ultimate conversation piece. The primary suite is a sanctuary unto itself, featuring a magnificent two-story closet and dedicated dressing room with a bar. Indulge in true tranquility within the home’s private wellness suite, complete with exercise room, a rejuvenating steam room, dry sauna and invigorating cold plunge tub. Additional interior highlights include the grand kitchen with Cristallo quartzite lighted countertops; a fully custom lounge with full bar; an upper-level game room with bar; an oversized, air-conditioned garage accommodating up to 8 vehicles; two laundry rooms; and more. Outdoor spaces are equally impressive, with an expansive lanai and balcony, a custom swimming pool with fire pits, meticulously landscaped yard adorned with integrated lighting, sound and lush, native greenery and putting green —all overlooking panoramic views of Isleworth’s championship golf course. Whether hosting guests or enjoying a peaceful evening at home, this estate offers a rare opportunity to live a life of unmatched beauty, comfort, and distinction in one of Central Florida's most desirable enclaves.
Highlights
Home typeSingle Family Residence
HeatingCentral, Electric
StatusActive
CoolingCentral Air, Zoned
Size9,511 sqft
Lot size1.02 Acres
Year built1999
ParkingElectric Vehicle Charging Station(s), Garage Door Opener, Oversized
MLS #O6304800
Attached garage6 spaces
FireplaceElectric, Gas
ViewGolf Course
Private poolYes
Virtual tour
Summary
- Partial Bathrooms: 1
- Full Bathrooms: 5
- Appliances: Bar Fridge, Oven, Dishwasher, Disposal, Freezer, Ice Maker, Microwave, Refrigerator, Tankless Water Heater, Washer, Wine Cooler
- Flooring Type: Marble, Tile, Wood
- Interior: Built-in Features, Ceiling Fans(s), High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Sauna, Smart Home, Stone Counters, Walk-In Closet(s), Wet Bar
- Fireplace: Electric, Gas
- Total Bedroom Count: 5
- Garage Space: 6 spaces
- Attached Garage: Yes
- Private Pool: Yes
- Parking: Electric Vehicle Charging Station(s), Garage Door Opener, Oversized
- View: Golf Course
- Exterior: Balcony, Lighting, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Rain Gutters
- Architectural Style: Custom
- Heating: Central, Electric
- Cooling: Central Air, Zoned
- List Price: $14,250,000
- Price/SqFt: $1,498
- HOA Amount: $3129 Quarterly
- Annual Tax Amount: $33,391
- Tax Year: 2023
- Lot: Cul-De-Sac, Landscaped, On Golf Course, Paved
- Directions: West on Conroy Windermere RD, at traffic circle take 3rd exit onto Main Street. Turn right onto Chase Road. Turn right onto Isleworth Country Club Drive. House will be on your left.
- Year Built: 1999
- Stories: 2
- Living Area: 9,511 SqFt
- Lot Size: 1.02 Acres
- MLS Number: O6304800
- MLS Name: MFRMLS
- Office Name: ISLEWORTH REALTY LLC
- Office Phone: (407) 909-9000
- Listing Agent: Monica Lochmandy
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Last updated on: 7/13/2025, 3:34:31 PM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.
Price information
Property sales
| Date | Event | Price |
|---|---|---|
| Nov 19, 2019 | Home Sold | $1,800,000 |
Tax history
| Year | Assessment | Property Tax |
|---|---|---|
| 2023 | $2,232,057 | $33,391 |
| 2022 | $1,826,805 | $29,127 |
| 2021 | $1,694,005 | $29,127 |
| 2020 | $1,701,776 | $27,531 |
| 2018 | $2,045,433 | $34,394 |
| 2017 | $2,012,693 | $34,214 |
History based on county public records data.
Nearby schools
10
Windermere Elementary School
Public District KG-5
1.8 mi
•11125 Park Ave
9
Sunset Park Elementary School
Public District KG-5
2.1 mi
•12050 Overstreet Rd
8
Palm Lake Elementary School
Public District KG-5
2.7 mi
•8000 Pin Oak Dr
School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.
Neighborhood
The neighbors living near this home have an average income of $94,580. Most Windermere, FL residents have annual incomes between $35k-100k. Residents typically live in married, no kids family. The majority of residents in this area have post secondary degree education.
How much money do the neighbors make?
13%
<35k
40%
35k-100k
23%
100k-200k
24%
200k+
What level of education do the neighbors have?
High School Diploma
Post Secondary Degree
Masters Degree
Doctorate
What types of families live nearby?
24%
Single, No Kids
6%
Single, with Kids
44%
Married, No Kids
26%
Married, with Kids
Are the neighbors home owners or renters?
Home Owners
Renters
How old are people in this area?
13%
<11 yrs old
11%
12-17 yrs old
12%
18-34 yrs old
51%
35-64 yrs old
13%
65+ yrs old
What do the neighbors do for fun?
Hiking/backpacking
Skiing/snowboarding
Men's Tennis
Where do the neighbors shop?
Nordstrom Rack
Nordstrom
Bloomingdales
Where do the neighbors go to eat?
Chipotle
California Pizza Kitchen
Bonefish Grill
What do the neighbors drive?
Mazda
BMW
Lexus
What do the neighbors listen to?
Rock
Talk/Personality
News
All data provided by Home Junction and Claritas
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Frequently asked questions
About 5525 Isleworth Country Club Dr
The listing price of 5525 Isleworth Country Club Dr property is $14,250,000.
The property 5525 Isleworth Country Club Dr is a house located in Windermere, Florida, 34786.
Active Listing: 5525 Isleworth Country Club Dr is For Sale (Active/New) which means the seller is accepting offers.
The nearby schools for 5525 Isleworth Country Club Dr are: Windermere Elementary School (GreatSchools Rating 10/10), Sunset Park Elementary School (GreatSchools Rating 9/10), Palm Lake Elementary School (GreatSchools Rating 8/10), Chain of Lakes Middle School (GreatSchools Rating 3/10), Horizon West Middle School (GreatSchools Rating 7/10), Windy Ridge School (GreatSchools Rating 8/10), Olympia High School (GreatSchools Rating 6/10), Windermere High School (GreatSchools Rating 8/10), Dr. Phillips High School (GreatSchools Rating 5/10).
According to the records, the last property tax for 2023 is $33,391 (source: MLS/based on county public records data).
The last sale was on November 19, 2019 for $1,800,000 (source: MLS/tax record).
The property at 5525 Isleworth Country Club Dr has 5 bedrooms and 5 full and 1 half bathrooms.
The property 5525 Isleworth Country Club Dr is 9,511 SqFt (source: MLS/tax record).
The year of construction for 5525 Isleworth Country Club Dr is 1999.
This home is located at 5525 Isleworth Country Club Dr in Windermere, FL and zip code 34786 in the Lake Butler neighborhood. This 9,511 square foot home, which was built in 1999, sits on a 1.02 acre lot. Features: 5 bedrooms, 6 bathrooms. It has been listed on Rocket Homes since May 19, 2025 and is currently priced at $14,250,000.
While more than 4 listings in Windermere, FL in June 2025 were sold above asking price, there were more than 9 listings sold at asking price, and more than 47 were sold below. The number of homes for sale in Windermere, FL increased by 2.8% between May and June 2025. Listings spent 84 days on the market in June 2025, and had a median list price of $740,000 during the same period.
From Rocket Homes Real Estate and based on county public records data.