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$8,500,000
New Listing

5092 ISLEWORTH COUNTRY CLUB DRIVE
WINDERMERE, FL 34786

For Sale|Single Family Residence|Active
4
Beds
5
Total Baths
5
Full Baths
7,100
SqFt
$1,197
/SqFt
1995
Built
Subdivision:
ISLEWORTH
County:
Orange
Call Now: (561) 935-3331
Is this the listing for you? We can help make it yours.
(561) 935-3331
5092 ISLEWORTH COUNTRY CLUB DRIVE5092 ISLEWORTH COUNTRY CLUB DRIVE5092 ISLEWORTH COUNTRY CLUB DRIVE5092 ISLEWORTH COUNTRY CLUB DRIVE
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Set along the front nine of Isleworth championship golf course with breathtaking views of Hole 6, this grand estate occupies an oversized lot along Isleworth’s main drive and has been beautifully reimagined with an extensive transformation over the last two years. The result is a sophisticated, move-in-ready home where timeless architectural character blends seamlessly with thoroughly modern style. Originally built by Pellegrini Homes and expanded to 7,100 square feet, the residence retains its signature architectural details, including custom ceilings, travertine floors with intricate tile inlays, and carefully crafted shell stone columns. The grandeur of the formal living room is accentuated by its soaring 20-foot ceiling, magnificent chandelier, and stately stone fireplace. A former bonus room has been thoughtfully transformed into the home's impressive new chef's kitchen, featuring custom cabinetry, an Italian-made 48-inch ILVE range, a luxury appliance collection, and elegant finishes. The original kitchen has been reimagined as a sophisticated entertaining bar with custom cabinetry, a built-in espresso cabinet, wine storage, and dedicated space for morning coffee and smoothies. Both spaces connect effortlessly to the casual dining area and formal dining room, creating an exceptional flow for everyday living and entertaining. The family room offers an open, airy setting with a built-in media display and effortless connection to the lanai. The main-level owner's suite provides a private retreat with a cozy fireplace, dual closets, and a lavish bath featuring dual vanities, a walk-in shower, and a luxurious soaking tub framed by elegant stone columns. A new main-level bedroom with private en-suite bath and an enlarged loft suite add flexibility for family and guests. Throughout the residence, new flooring, custom cabinetry and built-ins, designer lighting including bespoke Italian Murano glass fixtures, custom drapery, automated shades, and beautifully appointed furnishings create a cohesive, elevated aesthetic. Custom London-made closet lighting adds another layer of thoughtful detail, while modernized infrastructure, integrated technology, whole-home Wi-Fi, security, and smart-home features provide a seamless foundation for today's lifestyle. Outside, the residence has been transformed into an exceptional setting for both relaxation and entertaining. The pool has been resurfaced, outdoor living areas expanded, and a new outdoor kitchen and grilling area added, while a completely redesigned landscape, lighting, fencing, and fountain features enhance the grounds. Upstairs, the bedroom suites and expansive balcony capture panoramic views of the golf course and sparkling waters of Lake Bessie. The European-style lanai, with its graceful balustrade, creates an inviting setting for al fresco gatherings and captivating sunsets. This exceptional estate offers a rare combination of timeless architectural character, comprehensive modern improvements, sophisticated design, and an enviable golf-front setting within Isleworth.

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Listing Snapshot
Price 
$8,500,000
Days On Site 
0 Days
Bedrooms 
4
Inside Area (SqFt) 
7,100 sqft
Total Baths 
5
Full Baths 
5
Partial Baths 
N/A
Lot Size 
0.93 Acres
Year Built 
1995
MLS® Number 
O6446272
Status 
Active
Property Tax 
$57,070.63
HOA/Condo/Coop Fees 
$1,224 monthly
Sq Ft Source 
Owner
Friends & Family
Recent Activity
4 hours agoListing updated with changes from the MLS®
24 hours agoListing first seen on site
General Features
Acres 
0.93
Attached Garage 
Yes
Direction Faces 
East
Foundation 
Slab
Garage 
Yes
Garage Spaces 
4
Levels 
Two
Parking 
Circular DrivewayGarage Door OpenerGarage Faces SideGolf Cart GarageAttached
Pets 
Breed RestrictionsYes
Property Sub Type 
Single Family Residence
Security 
Closed Circuit Camera(s)Gated CommunitySecurity GateSecurity LightsSecurity SystemSmoke Detector(s)
Sewer 
Septic Tank
SqFt Total 
10319
Style 
Mediterranean
Utilities 
Cable AvailableNatural Gas AvailableCable ConnectedElectricity ConnectedNatural Gas ConnectedUnderground Utilities
Water Source 
Public
Zoning 
P-D
Interior Features
Appliances 
Bar FridgeConvection OvenDishwasherDisposalDryerElectric Water HeaterExhaust FanFreezerIce MakerMicrowaveRangeRange HoodRefrigeratorWasherWine Refrigerator
Cooling 
Central AirZoned
Fireplace 
Yes
Fireplace Features 
Living Room
Flooring 
BrickCarpetMarbleWood
Furnished 
Negotiable
Heating 
CentralZoned
Interior 
Built-in FeaturesCathedral Ceiling(s)Crown MoldingEat-in KitchenHigh CeilingsStone CountersVaulted Ceiling(s)Walk-In Closet(s)Wet Bar
Laundry Features 
Laundry Room
Spa 
Yes
Window Features 
Window CoveringsDrapesShuttersWindow Treatments
Dining Room 
Level - FirstDescription - Room4
Family Room 
Level - FirstDescription - Room5
Kitchen 
Level - FirstFeatures - Granite Counters, Kitchen IslandDescription - Room2
Living Room 
Level - FirstDescription - Room1
Master Bedroom 
Level - FirstDescription - Room3
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Exterior Features
Construction Details 
BlockStucco
Exterior 
BalconyLightingOutdoor GrillOutdoor ShowerRain Gutters
Fencing 
Fenced
Lot Features 
LandscapedOn Golf CoursePavedPrivate
Pool Features 
In GroundPrivate
Private Pool 
Yes
Roof 
Tile
Spa 
Yes
Spa Features 
HeatedIn Ground
View 
LakeWaterGardenGolf CourseTrees/Woods
Waterfront Features 
BUTLER CHAIN OF LAKES
Waterview 
LakeWaterGardenGolf CourseTrees/Woods
Windows/Doors 
Window CoveringsDrapesShuttersWindow Treatments
Community Features
Association Amenities 
Cable TVGatedMaintenancePlaygroundSecurity
Association Fee 
$3672.0
Association Fee Frequency 
Quarterly
Community Features 
GatedFitness CenterGolfPlaygroundPoolTennis Court(s)Street Lights
MLS Area 
34786 - Windermere
Township 
23
Financing Terms Available 
CashConventional
Roads 
Paved
Schools
School District
Unknown
Elementary School
Windermere Elem
Middle School
Chain of Lakes Middle
High School
Olympia High
Listing courtesy of ISLEWORTH REALTY LLC (407) 491-2690



Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2026, Stellar MLS.
Last checked: 2026-10-02 10:42 AM EDT

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
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