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Windermere, FL · Single Family Residence

5092 Isleworth Country Club Dr

$8,500,000
List price
4Bedrooms
5Bathrooms
7,100Square feet
0.93Acres

THE SETTING, AND THE DETAILS

A closer look.

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.

Private poolGarage

The details that help you decide.

Details supplied with the listing. Information that was not provided is marked below.

Home essentials
Price per square foot
$1,197
Full bathrooms
5
Half bathrooms
0
Heated living area
7100
Lot size (acres)
0.93
Lot size (sq ft)
40620
Year built
1995
Property type
Residential
Property style
Mediterranean
Interior & rooms
Interior features
Built-in Features, Cathedral Ceiling(s), Ceiling Fans(s), Central Vaccum, Crown Molding, Eat-in Kitchen, High Ceilings, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Solid Wood Cabinets, Stone Counters, Vaulted Ceiling(s), Walk-In Closet(s), Wet Bar, Window Treatments
Appliances
Bar Fridge, Built-In Oven, Convection Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer, Water Filtration System, Wine Refrigerator
Flooring
Brick, Carpet, Marble, Travertine, Wood
Additional rooms
Not provided
Land, water & community
Waterfront
No
Waterfront type
Not provided
Water body / lake name
BUTLER CHAIN OF LAKES
Water view
Lake - Chain of Lakes
Dock
Not provided
Dock features
Not provided
Other views
Garden, Golf Course, Trees/Woods, Water
Lot features
Landscaped, On Golf Course, Oversized Lot, Paved, Private
Exterior features
Balcony, Lighting, Outdoor Grill, Outdoor Shower, Rain Gutters
Community amenities
Association Recreation - Owned, Community Mailbox, Fitness Center, Golf Carts OK, Golf, Playground, Pool, Tennis Court(s), Street Lights
Zoning
P-D
Current use
Not provided
Horse amenities
Not provided
Fencing
Fenced
Other structures
Not provided
Pool, parking & systems
Private pool
Yes
Pool features
In Ground, Lighting
Garage
Yes
Garage spaces
4
Carport
No
Carport spaces
Not provided
Parking features
Circular Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Garage
Fireplace
Yes
Fireplace features
Living Room, Primary Bedroom
Heating
Central, Zoned
Cooling
Central Air, Zoned
Water supply
Public
Sewer
Septic Tank
Utilities
Cable Connected, Electricity Connected, Fire Hydrant, Natural Gas Connected, Underground Utilities
Construction
Construction materials
Block, Stucco
Roof
Tile
Foundation
Slab
Stories
Not provided
Levels
Two
Location & schools
City
WINDERMERE
Subdivision
ISLEWORTH
County
Orange
ZIP code
34786
Elementary school
Windermere Elem
Middle school
Chain of Lakes Middle
High school
Olympia High
Association, taxes & listing
HOA / association
Yes
Association fee
$3,672
Fee frequency
Quarterly
Included services
Guard - 24 Hour, Cable TV, Escrow Reserves Fund, Internet, Maintenance Grounds, Maintenance, Private Road, Security
Association amenities
Cable TV, Gated, Maintenance, Optional Additional Fees, Playground, Security
Additional association fee
Not provided
Additional fee frequency
Not provided
Condo fee
Not provided
Condo fee frequency
Not provided
Annual property taxes
$57,070.63
Tax year
2026
Other annual assessments
Not provided
CDD
No
Listing status
Active
Days on market
0
Listing broker
ISLEWORTH REALTY LLC
MLS number
MFRO6446272

Explore the area

Location supplied with the listing. Confirm boundaries and access for the property.

Listed by ISLEWORTH REALTY LLC · MLS MFRO6446272
Source: mfrmls · Listing updated 2026-10-01 17:31:17 UTC.
Information is deemed reliable but is not guaranteed. Availability and details may change.

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