5092 Isleworth Country Club Drive, Windermere, FL 34786
$8,500,000 - For Sale
Property Details
Price: $8,500,000
Sq Ft: 7,100
($1,197 per sqft)
Bedrooms: 4
Bathrooms: 5
City:Windermere
County:Orange
Type:Single Family
Development:Isleworth
Subdivision:Isleworth
Acres:0.9300
Virtual Tour/Floorplan:View
Year Built:1995
Listing Number:O6446272
Status Code:A-Active
Taxes:$57,070.63
Tax Year: 2026
Garage: 4
/ Y
Furnishings: Negotiable
Pets Allowed: Breed Restrictions, Yes
Total Recurring Fees: $1,224
Total Recurring Fee Frequency: 0.00
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Equipment:
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
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
Exterior Features:
Balcony
Lighting
Outdoor Grill
Outdoor Shower
Rain Gutters
View:
Garden
Golf Course
Trees/Woods
Water
Amenities:
Cable TV
Gated
Maintenance
Optional Additional Fees
Playground
Security
Financial Information:
Taxes: $57,070.63
Tax Year: 2026
Association Fee: $3,672.00
Association Fee Frequency: Quarterly
Room Dimensions:
Laundry: Laundry Room
School Information:
Elementary School: Windermere Elem
Middle School: Chain Of Lakes Middle
Junior High: Chain Of Lakes Middle
High School: Olympia High
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View Virtual Tour
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.
Building Description: Mediterranean
MLS Area: 34786 - Windermere
Total Square Footage: 10,319
Price per Square Feet: $1,197.18
Water: Public
Construction: Block, Stucco
Date Listed: 2026-10-01 00:00:00
Pool: Y
Pool Description: In Ground, Lighting
Private Spa: Y
Furnished: Negotiable
Windows: Drapes, Shutters, Window Treatments
Parking: Circular Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Garage
Garage Description: Y
Garage Spaces: 4
Attached Garage: Y
Flooring: Brick, Carpet, Marble, Travertine, Wood
Roof: Tile
Heating: Central, Zoned
Cooling: Central Air, Zoned
Fireplace: Y
Security: Closed Circuit Camera(S), Gated Community, Security Gate, Security Lights, Security System, Smoke Detector(S)
Laundry: Laundry Room
Pets: Breed Restrictions, Yes
Sewer: Septic Tank
Lot Desc.: Landscaped, On Golf Course, Oversized Lot, Paved, Private
Parcel ID: 16-23-28-3899-0
Amenities: Cable Tv, Gated, Maintenance, Optional Additional Fees, Playground, Security
Listing Courtesy Of: Isleworth Realty Llc
michelle.corbin@isleworth.com
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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Additional Information:
Building Description: Mediterranean
MLS Area: 34786 - Windermere
Total Square Footage: 10,319
Price per Square Feet: $1,197.18
Water: Public
Construction: Block, Stucco
Date Listed: 2026-10-01 00:00:00
Pool: Y
Pool Description: In Ground, Lighting
Private Spa: Y
Furnished: Negotiable
Windows: Drapes, Shutters, Window Treatments
Parking: Circular Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Garage
Garage Description: Y
Garage Spaces: 4
Attached Garage: Y
Flooring: Brick, Carpet, Marble, Travertine, Wood
Roof: Tile
Heating: Central, Zoned
Cooling: Central Air, Zoned
Fireplace: Y
Security: Closed Circuit Camera(S), Gated Community, Security Gate, Security Lights, Security System, Smoke Detector(S)
Laundry: Laundry Room
Pets: Breed Restrictions, Yes
Sewer: Septic Tank
Lot Desc.: Landscaped, On Golf Course, Oversized Lot, Paved, Private
Parcel ID: 16-23-28-3899-0
Amenities: Cable Tv, Gated, Maintenance, Optional Additional Fees, Playground, Security
Map of 5092 Isleworth Country Club Drive, Windermere, FL 34786
Listing Courtesy Of: Isleworth Realty Llc
michelle.corbin@isleworth.com
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Location
2100 Constitution Boulevard
Sarasota, FL 34231
Contact
Jennifer Leblanc, Broker
941-400-0374
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