Virtual TourMap

For SaleSingle Family ResidenceActive

5092 Isleworth Country Club Drive

Windermere, FL 34786

$8,500,000

42 Days On Site

  • 4Beds
  • 5Baths5 full
  • 7,100Sq Ft
  • $1,197Per Sq Ft
  • 0.93Acres
  • 1995Built
Subdivision
Isleworth
County
Orange
MLS®
O6446272

Overview

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.

Listing Snapshot

Price
$8,500,000
Days On Site
42 Days
Bedrooms
4
Inside Area (SqFt)
7,100 sqft
Total Baths
5
Full Baths
5
Partial Baths
0
Lot Size
0.93 Acres
Year Built
1995
MLS® Number
O6446272
Status
Active
Property Tax
$57,070.63 (2026)
HOA/Condo/Coop Fees
$1,224 monthly
Sq Ft Source
Owner

Property Details

General Features

17 items
Acres
0.93
Attached Garage
Yes
Direction Faces
East
Foundation
Slab
Garage
Yes
Garage Spaces
4
Levels
Two
Parking
Circular Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Garage, Attached
Pets
Breed Restrictions, Yes
Property Sub Type
Single Family Residence
Security
Closed Circuit Camera(s), Gated Community, Security Gate, Security Lights, Security System, Smoke Detector(s)
Sewer
Septic Tank
SqFt Total
10,319
Style
Mediterranean
Utilities
Cable Available, Natural Gas Available, Cable Connected, Electricity Connected, Natural Gas Connected, Underground Utilities
Water Source
Public
Zoning
P-D

Interior Features

16 items
Appliances
Bar Fridge, Convection Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
Cooling
Central Air, Zoned
Fireplace
Yes
Fireplace Features
Living Room
Flooring
Brick, Carpet, Marble, Wood
Furnished
Negotiable
Heating
Central, Zoned
Interior
Built-in Features, Cathedral Ceiling(s), Crown Molding, Eat-in Kitchen, High Ceilings, Stone Counters, Vaulted Ceiling(s), Walk-In Closet(s), Wet Bar
Laundry Features
Laundry Room
Spa
Yes
Window Features
Window Coverings, Drapes, Shutters, Window Treatments

Rooms

RoomDimensionsLevelFeatures
Dining RoomFirstDescription - Room4
Family RoomFirstDescription - Room5
KitchenFirstGranite Counters, Kitchen Island, Description - Room2
Living RoomFirstDescription - Room1
Master BedroomFirstDescription - Room3

Exterior Features

13 items
Construction Details
Block, Stucco
Exterior
Balcony, Lighting, Outdoor Grill, Outdoor Shower, Rain Gutters
Fencing
Fenced
Lot Features
Landscaped, On Golf Course, Paved, Private
Pool Features
In Ground, Private
Private Pool
Yes
Roof
Tile
Spa
Yes
Spa Features
Heated, In Ground
View
Lake, Water, Garden, Golf Course, Trees/Woods
Waterfront Features
BUTLER CHAIN OF LAKES
Waterview
Lake, Water, Garden, Golf Course, Trees/Woods
Windows/Doors
Window Coverings, Drapes, Shutters, Window Treatments

Community Features

8 items
Association Amenities
Cable TV, Gated, Maintenance, Playground, Security
Association Fee
$3672.0
Association Fee Frequency
Quarterly
Community Features
Gated, Fitness Center, Golf, Playground, Pool, Tennis Court(s), Street Lights
MLS Area
34786 - Windermere
Township
23
Financing Terms Available
Cash, Conventional
Roads
Paved

Location

5092 Isleworth Country Club Drive, Windermere, FL 34786 · 34786 - Windermere

Neighborhood & Commute

ZIP Code 34786

Median household income
$127,371
Income per person
$64,053
Households
17,419
Average household size
2.82
Median age
38.9

Source: Walk Score.

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

Schools

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

Price & Status History

  1. Listing updated with changes from the MLS®
  2. Listing first seen on site
  3. Status changed to Active

Friends & Family

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Listing courtesy of ISLEWORTH REALTY LLC (407) 491-2690

Stellar MLS

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: 2026-11-12 10:35 AM EST

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