5092 ISLEWORTH COUNTRY CLUB DRIVE Windermere, FL $ 8,500,000
5092 ISLEWORTH COUNTRY CLUB DRIVE
$ 8,500,000
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5092 ISLEWORTH COUNTRY CLUB DRIVE

Windermere, FL, 34786
$ 8,500,000
Bedrooms4 Baths5.0 Sq 7,100

Monthly Estimate*

$ 53,670

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Single Family Home for sale in Windermere, FL

for $8,500,000 with 4 bedrooms and 5 full baths. This 7,100 square foot home was built in 1995 on a lot size of 0.93.

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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Single Family Active

Price

$ 8,500,000

Bedrooms

4

Full Bath

5

Property Type

Single Family

Taxes

$ 57,070

Style

Mediterranean

Lot Size

0.93

Year Built

1995

Town/City

Windermere

County/Region

Orange

MLS | Web ID

O6446272

Features
General
Sewer Septic Tank
Heating Central Zoned
Cooling Central Air Zoned
Utilities Cable Connected Electricity Connected Fire Hydrant Natural Gas Connected Street Lights Underground Utilities
Roof Tile
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
Zoning P-D
HOA Fee 3672
Garage Spaces 4
Association Fee Includes 24-Hour Guard Cable TV Escrow Reserves Fund Internet Maintenance Grounds Maintenance Repairs Private Road Security
Architectural Style Mediterranean
Pool Features In Ground Lighting
Security Features Closed Circuit Camera(s) Gated Community Security Gate Security Lights Security System Smoke Detector(s)
Construction Materials Block Stucco
Pets Allowed Breed Restrictions Yes
Year Built 1995
View Garden Golf Course Trees/Woods Water
Levels Two
Property Subtype Single Family Residence
Tax Year 2026
Ownership Fee Simple
Community Features Association Recreation - Owned Community Mailbox Fitness Center Golf Carts OK Golf Playground Pool Tennis Court(s)
Assoc Fee Paid Per Quarterly
County Orange
New Construction false
Property Type Residential
Association Amenities Cable TV Gated Maintenance Optional Additional Fees Playground Security
Attached Garage true
Subdivision Name ISLEWORTH
Facing Direction East
Garage Y/N true
Total Rooms 5
Full Baths 5
Status Active
Directions I-4 to Conroy Windermere Road west to Isleworth subdivision. Stay straight on Isleworth Country Club Drive. Estate will be on the Left or Right.
High School Olympia High
City WINDERMERE
Body of Water BUTLER CHAIN OF LAKES
Association Name Dan O’Connell
Senior Community Y/N false
MLS Area 34786 - Windermere
Lot Size Units Square Feet
Lot Size Square Feet 40620
Carport Y/N false
Listing Terms Cash Conventional
Spa Features Heated In Ground
Elementary School Windermere Elem
Land Lease Y/N false
Tax Annual Amount 57070.63
Middle/Junior High School Chain of Lakes Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://player.vimeo.com/video/1230185615?h=e9768a3a03&badge=0&autopause=0&player_id=0&app_id=58479
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Owner
Tax Lot 48
Legal Description N 73 DEG W 204.27 FT S 22 DEG W ALONG LOTS 47 & 48 FOR 146.32 FT TO POB
Water View Lake - Chain of Lakes
Minimum Lease 8-12 Months
Water Access Y/N false
Monthly HOA Amount 1224
Water View Y/N true
Flood Zone Code X
In Law Suite YN false
Flood Zone Code X Y
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Interior
Interior Amenities Built-in Features Cathedral Ceiling(s) Ceiling Fan(s) Central Vacuum Crown Molding Eating Space 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
Flooring Brick/Stone Carpet Marble Travertine Hardwood
Furnished Y/N Negotiable
Fireplace Features Living Room Master Bedroom
Air Conditioning Y/N true
Heating Y/N true
Window Features Drapes Shutters Window Treatments
Fireplace Y/N true
Half Baths 0
Laundry Features Laundry Room
Total Bedrooms 4
Total Baths 5
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Exterior
Exterior Amenities Balcony French Doors Irrigation System Lighting Outdoor Grill Outdoor Shower Rain Gutters
Vegetation Mature Landscaping Trees/Landscaped
Fencing Fenced
Parking Features Circular Driveway Garage Door Opener Garage Faces Side Golf Cart Garage
Lot Features Landscaped On Golf Course Oversized Lot
Water Source Public
Lot Size Area 40620
Foundation Details Slab
Spa true
Building Area Total 10319
Lot Size Acres 0.93
Road Surface Type Paved
Private Pool true
Waterfront Y/N false
Covered Spaces 4
Road Frontage Type Street Paved Private Road
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* Excluded Features
List By
Isleworth Realty Llc

Broker

michelle.corbin@isleworth.com

Email

Affordability Calculator

$58,426
Per Month
92%
8%
0%
Monthly Principal & Interest
$53,670
Monthly Property Taxes
$4,756
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Olympia High High School High School
Pricing History
DatePricePrice ChangeDescription
10/1/2026$8,500,000 Listed Price

Map


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5092 ISLEWORTH COUNTRY CLUB DRIVE, Windermere, FL, 34786 is a Single Family Home for sale at $8,500,000 with 7,100 sqft and a lot size of 0.93. 5092 ISLEWORTH COUNTRY CLUB DRIVE has 4 bedrooms, 5.0 baths, and was built in 1995. The property's zip code is 34786 which is in Windermere, FL