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5092 Isleworth Country Club Drive, Windermere, FL

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$8,500,000

($1,197/sqft)

List Status: Active
5092 Isleworth Country Club Drive
Windermere, FL 34786


4 beds
5 baths
7100 living sqft
Top Features
  • View: Water, Garden, Golf Course, Trees/Woods
  • Subdivision: Isleworth
  • Built in  1995
  • Single Family Residence
Description
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
Property Details
Property Features
Property Sub Type
Single Family Residence
View
Water, Garden, Golf Course, Trees/Woods
Parking
Garage Faces Side, Circular Driveway, Garage Door Opener, Golf Cart Garage
Pool
Lighting, In Ground
County
Orange
Subdivision
ISLEWORTH
Interior Features
MlsStatus
Active
Additional Information
Additional Lease Restrictions
Per Isleworth Community Association (ICA)
Additional Water Information
The Isleworth community is set along six of the lakes within the much desirable Butler Chain of Lakes. We offer a private, community boat ramp for our residents eager to enjoy these great waters.
Amenities Additional Fees
Club amenities are available to Club members only. Residents of the community are not required to join the Isleworth Golf & Country Club.
Appliances
Freezer, Built-In Oven, Electric Water Heater, Exhaust Fan, Dishwasher, Bar Fridge, Microwave, Range Hood, Refrigerator, Disposal, Dryer, Range, Washer, Wine Refrigerator, Water Filtration System, Convection Oven, Ice Maker
Approval Process
Per Isleworth Community Association (ICA)
Architectural Style
Mediterranean
Association Amenities
Cable TV, Optional Additional Fees, Maintenance, Security, Gated, Playground
Association Fee
3672
Association Fee Frequency
Quarterly
Association Fee Includes
Maintenance Grounds, Cable TV, Private Road, Guard - 24 Hour, Internet, Maintenance, Security, Escrow Reserves Fund
Association Fee Requirement
Required
Bathrooms Total Integer
5
Building Area Source
Public Records
Building Area Total
10319
Building Area Total Srch SqM
958.67
Building Area Units
Square Feet
Calculated List Price By Calculated SqFt
1197.18
Community Features
Golf Carts OK, Golf, Community Mailbox, Tennis Court(s), Fitness Center, Street Lights, Pool, Association Recreation - Owned, Playground
Construction Materials
Stucco, Block
Cooling
Zoned, Central Air
Country
US
Cumulative Days On Market
1
Current Price
8500000.00
Direction Faces
East
Elementary School
Windermere Elem
Exterior Features
Outdoor Grill, Balcony, Lighting, Outdoor Shower, Rain Gutters
Fencing
Fenced
Fireplace Features
Primary Bedroom, Living Room
Flood Zone Code
X
Flooring
Wood, Brick, Travertine, Carpet, Marble
Foundation Details
Slab
Furnished
Negotiable
Garage Spaces
4
Heating
Zoned, Central
High School
Olympia High
Interior Features
Eat-in Kitchen, Built-in Features, High Ceilings, Cathedral Ceiling(s), Central Vaccum, Walk-In Closet(s), Wet Bar, Window Treatments, Crown Molding, Vaulted Ceiling(s), Solid Wood Cabinets, Stone Counters, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Ceiling Fans(s)
Laundry Features
Laundry Room
Levels
Two
List AOR
Orlando Regional
Living Area Meters
659.61
Living Area Source
Owner
Living Area Units
Square Feet
Lot Features
Paved, Landscaped, On Golf Course, Private, Oversized Lot
Lot Size Acres
0.93
Lot Size Square Feet
40620
Lot Size Square Meters
3774
Middle Or Junior School
Chain of Lakes Middle
Minimum Lease
8-12 Months
Modification Timestamp
2026-10-02T10:49:22.808Z
Monthly HOA Amount
1224.00
Occupant Type
Owner
Other Equipment
Irrigation Equipment
Ownership
Fee Simple
Parcel Number
16-23-28-3899-00-480
Pet Restrictions
Per Orange County breed restrictions, number limits and leash laws.
Pets Allowed
Yes, Breed Restrictions
Public Survey Range
28
Public Survey Section
16
RATIO Current Price By Calculated SqFt
1197.18
Road Surface Type
Paved
Roof
Tile
Room Count
5
Security Features
Security Gate, Closed Circuit Camera(s), Gated Community, Security Lights, Security System, Smoke Detector(s)
Sewer
Septic Tank
Spa Features
Heated, In Ground
Tax Annual Amount
57070.63
Tax Block
00
Tax Book Number
16/118
Tax Lot
48
Tax Year
2026
Total Acreage
1/2 to less than 1
Total Annual Fees
14688.00
Total Monthly Fees
1224.00
Township
23
Universal Property Id
US-12095-N-162328389900480-R-N
Unparsed Address
5092 ISLEWORTH COUNTRY CLUB DR
Utilities
Underground Utilities, Cable Connected, Fire Hydrant, Natural Gas Connected, Electricity Connected
Vegetation
Mature Landscaping, Trees/Landscaped
Water Body Name
BUTLER CHAIN OF LAKES
Water Source
Public
Water View
Lake - Chain of Lakes
Window Features
Window Treatments, Drapes, Shutters
Zoning
P-D
Neighborhood Map
Popup

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MLS #MFRO6446272 Listing courtesy of Isleworth Realty Llc provided by Stellar MLS.



All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independent verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. The source of the listing data is as follows: Stellar MLS (updated 11/15/26 6:51 PM) |

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