5525 Isleworth Country Club Dr, Windermere, FL 34786
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About this home
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.
Est. $5,219 per month, based on comparable rentals
Sale and tax history for 5525 Isleworth Country Club Dr
Sale History
Tax History
Date
Event
Price
Stellar MLS as Distributed by MLS Grid #O6304800
May 15, 2026
Sold
$11,500,000
$1,209/sq ft
Apr 17, 2026
Pending
—
May 19, 2025
Listed
$14,250,000
$1,498/sq ft
Stellar MLS as Distributed by MLS Grid #O5816776
Nov 15, 2019
Sold
$1,800,000
$189/sq ft
Oct 8, 2019
Pending
—
Oct 2, 2019
Listed
$1,925,000
$202/sq ft
Take a look at this TREMENDOUS OPPORTUNITY in world famous Isleworth! This ESTATE OWNED property represents the least expensive price per square foot in Isleworth! With solid comps and a mainly cosmetic rehab, this property represents an opportunity that rarely presents itself in one of the most prestigious, private golf club communities in the world. Truly ONE OF A KIND TUSCAN VILLA features 6 bedrooms (including STUDIO APARTMENT With SEPARATE ENTRANCE), 6 1/2 bathrooms on a PREMIUM DOUBLE LOT with views of the 14th fairway of Isleworth Country Club’s golf course. FLEXIBLE FLOOR PLAN can easily be modified. Master Suite is amazing with 3 walk-in closets, oversized walk-in shower, plumbed for a tub, MASSIVE dual vanities & access to PRIVATE OPEN DECK. Ensuite bedrooms are generously sized & have spacious walk-in closets. Due to the double lot, there are many options to add a pool & outdoor entertaining area & still have plenty of yard leftover! Volume ceilings, hammered wood beams, fireplace, extensive moldings, GORGEOUS STAINED GLASS, circular brick pavered driveway, oversized 3 car garage. Did you notice the SPECTACULAR HARDWOOD FLOORS? Check out the STUNNING LANAI! TONS OF NATURAL LIGHT! Isleworth is set amidst grand cypress & oak trees & surrounded by freshwater lakes, the 600-acre golf club community's natural environment provides an exquisite backdrop. Thousands of trees & flowers, along with sculptures and magnificent estates, line the streets, CREATING A STUNNING SETTING NOT FOUND ANYWHERE ELSE.
Stellar MLS as Distributed by MLS Grid #O5770405
Sep 15, 2019
Listing Removed
—
Jun 17, 2019
Price Changed
*
May 17, 2019
Relisted
—
May 2, 2019
Pending
—
Mar 15, 2019
Listed
*
Public Records
Apr 27, 1998
Sold
$75,000
$8/sq ft
Public Records
Jun 9, 1995
Sold
$133,000
$14/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$44,078 (+17.9%)
$925,000 + $1,740,010
$2,665,010
2024
$37,372 (+11.9%)
$925,000 + $1,740,010
$2,665,010
2023
$33,391 (+14.6%)
$925,000 + $1,410,957
$2,335,957
2022
$29,128 (+5.8%)
$725,000 + $1,101,805
$1,826,805
2021
$27,531 (+2.9%)
$725,000 + $1,101,805
$1,826,805
2020
$26,758 (−22.5%)
$725,000 + $969,005
$1,694,005
2019
$34,529 (+0.4%)
$770,000 + $1,308,892
$2,078,892
2018
$34,395 (+0.5%)
$770,000 + $1,308,892
$2,078,892
2017
$34,215 (−0.2%)
$770,000 + $1,242,693
$2,012,693
2016
$34,290 (−0.3%)
$770,000 + $1,242,693
$2,012,693
2015
$34,376 (+5.5%)
$770,000 + $1,162,686
$1,932,686
2014
$32,597 (+10.8%)
2013
$29,419 (+3.2%)
2012
$28,507
Public record
Public record
Zoning
Beds
5
Baths
6
Stories
2
Lot width
—
Lot depth
—
Lot size
1.02 Acres
Year renovated
1999
Sq. Ft.
7,653
Year built
1999
Style
Single Family Residential
County
Orange County
APN
282316389901550
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Aug 17, 2026.
P-D
Planned Development District
To provide for planned residential communities, containing a variety of residential structures and diversity of building arrangements, with complementary and compatible commercial or industrial uses or both; planned commercial centers with complementary and compatible residential or industrial uses or both; planned tourist commercial centers with complementary and compatible uses which may include tourist attractions, theme parks, residential and light storage; or planned industrial parks with complementary and compatible residential or commercial uses or both; and public and quasipublic facilities developed in accordance with an approved development plan; To allow diversification of uses, structures, and open spaces in a manner compatible with existing and permitted land uses on abutting properties; To reduce improvement and energy costs through a more efficient use of land design and smaller networks of utilities and streets than is possible through application of other zoning districts and subdivision requirements; To ensure that development will occur according to limitations of use, design, density, coverage and phasing stipulated on an approved development plan; To preserve the natural amenities and environmental assets of the land by encouraging the preservation and improvement of scenic and functional open areas; To encourage an increase in the amount and use of open space areas by permitting a more economical and concentrated use of building areas than would be possible through conventional zoning districts; To provide maximum opportunity for application of innovative concepts of site planning in the creation of aesthetically pleasing living, shopping and working environments on properties of adequate size, shape and location; The P-D district is a flexible zoning district which is intended to provide an appropriate balance between the intensity of development and the ability to provide adequate capacity within the support services and facilities.
Permitted uses
Include but are not limited to:
No uses permitted by right
Property details
Parking
Parking Information
Parking Features: Electric Vehicle Charging Station(s), Garage Door Opener, Oversized
Garage Spaces: 6
Has Attached Garage
Has Garage
Interior
Virtual Tour
Bedroom Information
# of Bedrooms: 5
Bathroom Information
# of Full Baths (Total): 5
# of Half Baths (Total): 1
Laundry Room Information
Laundry Features: Inside, Laundry Room
Other Rooms Information
Additional Rooms: Family Room,Great Room
# of Rooms: 8
Fireplace Information
Has Fireplace
Fireplace Features: Electric, Gas
Heating & Cooling
Heating Information: Central, Electric
Cooling Information: Central Air, Zoned
Interior Features
Interior Features: Built-in Features, Ceiling Fans(s), High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Sauna, Stone Counters, Walk-in Closet(s), Wet Bar
Appliances: Bar Fridge, Built-In Oven, Dishwasher, Disposal, Freezer, Ice Maker, Microwave, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator
Lot Features: Cul-De-Sac, Landscaped, On Golf Course, Paved
Lot Size Acres: 1.02
Road Surface Type: Paved
Lot Size Square Meters: 4137
Building Information
MFR_BuildingAreaTotalSrchSqM: 1144.47
Financial
Tax Information
Tax Annual Amount: $37,372.24
Tax Year: 2024
Lease / Rent Details
Lease Restrictions YN: 0
Utilities
Utility Information
Water Source: Public
Sewer: Septic Tank
Utilities: Cable Connected, Electricity Connected, Natural Gas Connected, Sprinkler Well, Water Connected
Additional Water Information: The Isleworth community is set along six of the lakes within the much desirable Butler Chain of Lakes. We offer a private, community boat ramp for our residents eager to enjoy these great waters.
Middle Or Junior High School: Chain of Lakes Middle
High School: Olympia High
Location Information
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.
Condo Information
Floor Number: 2
Community Information
Community Features: Golf Carts OK, Playground, Street Lights
Pets Allowed: Breed Restrictions, Yes
Public facts
Beds: 5
Baths: 6.0
Sq. Ft.: 7,653
Stories: 2.0
Lot Size: 1.02 acres
Style: Single Family Residential
Year Built: 1999
Year Renovated: 1999
County: Orange County
APN: 282316389901550
Home facts updated by county records on Aug 17, 2026
Other
Miscellaneous Information
Third Party YN: 1
Listing Information
Attribution Contact: 407-909-9000
Previous Status: Pending
Backups Requested YN: 1
Listing Date Information
Days to Contract: 333
Status Contractual Search Date: 2026-05-15
Listing Price Information
Calculated List Price By Calculated Sq Ft: 1498.27
Green Information
Green Verification Count: 0
Direction Faces: Northeast
Home Information
Living Area: 9511
Living Area Units: Square Feet
Living Area Source: Owner
Living Area Meters: 883.60
Building Area Total: 12319
Building Area Units: Square Feet
Building Area Source: Owner
Foundation Details: Block, Slab
Builder Name: Ballard Custom Homes
Stories Total: 2
Levels: Two
Security Features: Gated Community, Security Gate, Security System
Around this home
Schools
Windermere Elementary School
Public PreK-5 • Assigned • 1.8mi
10/10
Chain Of Lakes Middle School
Public 6-8 • Assigned • 2.2mi
3/10
Olympia High School
Public 9-12 • Assigned • 2.3mi
5/10
Provided by GreatSchools
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
2/10 Fire Factor
0.00% chance of being in a wildfire in next 30 years
8/10 Heat Factor
7 days above 108° expected this year, 23 days in 30 years
10/10 Wind Factor
99% chance of strong winds in next 30 years
1/10 Air Factor
0 unhealthy days expected this year, 0 days in 30 years
Provided by First Street
Historical weather
Windermere, FL • 34786
Average low and high temperatures (°F)
68
48
75
54
81
60
84
65
90
72
91
74
92
76
91
76
89
75
83
69
78
60
73
55
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
93/ 100
Exceptional sunlight
Sunscore
This home receives average direct sun exposure in the zip code. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
10.2 hrs
7.4 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$10.97M – $13.28M
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