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5525 ISLEWORTH COUNTRY CLUB DR
WINDERMERE, FL, 34786
$14,250,000
5 Beds
5.5 Baths
9,511 SqFt
1.02 Acres
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MLS #O6304800 image #0
Under contract-accepting backup offers. One or more photo(s) has been virtually staged. 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 more than 2,200-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.

Property Details

Price:
$14,250,000
MLS #:
O6304800
Status:
Pending
Beds:
5
Baths:
5.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
ISLEWORTH
Neighborhood:
34786windermere
Listed Date:
May 19, 2025
Finished Sq Ft:
9,511
Total Sq Ft:
12,319
Lot Size:
44,529 sqft / 1.02 acres (approx)
Year Built:
1999
CustomWaterfrontLakefrontPoolPrimary Bedroom Main FloorCommunity Gated34786 – Windermere34786windermereIsleworthWindermere ElemChain Of Lakes MiddleOlympia HighLake Butler Chain Of LakesGolf CoursePer Isleworth Community Association (ica)8-12 MonthsPets Allowed

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Schools

Elementary School:
Windermere Elem
Middle School:
Chain of Lakes Middle
High School:
Olympia High

Interior

Appliances
Bar Fridge, Built-In Oven, Dishwasher, Disposal, Freezer, Ice Maker, Microwave, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator
Bathrooms
5 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air, Zoned
Flooring
Marble, Tile, Hardwood
Heating
Central, Electric
Interior Features
Built-in Features, Ceiling Fan(s), High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Sauna, Smart Home, Stone Counters, Walk-In Closet(s), Wet Bar
Laundry Features
Inside, Laundry Room
Levels
Two

Exterior

Architectural Style
Custom
Attached Garage YN
1
Community Features
Lake, Private Boat Ramp, Gated Community – Guard, Golf Carts OK, Playground
Construction Materials
Block, Concrete
Covered Spaces
6
Direction Faces
Northeast
Exterior Features
Balcony, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Rain Gutters
Fencing
Fenced
Garage Spaces
6
Lot Features
Cul-De-Sac, Landscaped, On Golf Course
Other Structures
Outdoor Kitchen
Parking Features
Electric Vehicle Charging Station(s), Garage Door Opener, Oversized
Patio And Porch Features
Porch, Screened
Roof
Tile
Security Features
Gated Community, Security Gate, Security System
Spa Features
Heated, In Ground
View
Golf Course
Waterfront Features
Lake

Financial

HOA Fee
$3,672
HOA Fee Frequency
Quarterly
HOA Includes
24-Hour Guard, Cable TV, Escrow Reserves Fund, Internet, Maintenance Grounds, Maintenance Repairs, Private Road, Security
HOA Name
Dan O’Connell
Tax Year
2024
Taxes
$37,372

Map

Community

Subdivisions in WINDERMERE

Market Summary

Current real estate data for Single Family in WINDERMERE as of Apr 23, 2026
289
Single Family Listed
96
Avg DOM
458
Avg $ / SqFt
$2,232,330
Avg List Price

Property Summary

    Located in the ISLEWORTH subdivision, 5525 ISLEWORTH COUNTRY CLUB DR WINDERMERE FL is a Single Family for sale in WINDERMERE, FL, 34786. It is listed for $14,250,000 and features 5 beds, 6 baths, and has approximately 9,511 square feet of living space, and was originally constructed in 1999. The current price per square foot is $1,498. The average price per square foot for Single Family listings in WINDERMERE is $458. The average listing price for Single Family in WINDERMERE is $2,232,330. To schedule a showing of MLS#o6304800 at 5525 ISLEWORTH COUNTRY CLUB DR in WINDERMERE, FL, contact your Preferred Real Estate Brokers agent at 4076987254.

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5525 ISLEWORTH COUNTRY CLUB DR
WINDERMERE, FL