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$8,500,000

4 Beds 5 Baths 7,100 SQFT 0.93 Acres
Type: Single Family

5092 ISLEWORTH COUNTRY CLUB DRIVE
WINDERMERE, FL 34786

MLS#: O6446272
Abby Tomassoni
Abby Tomassoni
The Real Estate Advantage
Phone: 763.234.9123
Office: 763.755.1100
Presented by: ISLEWORTH REALTY LLC with 407-909-9000. - 407-909-9000

Property 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 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.


 

Interior Features

Bedrooms

Total Bedrooms4

Bathrooms

Half Baths0
Total Baths5

Other Interior Features

LivingAreaSource0 sqft
Air Conditioning Y/NYes
Fireplace FeaturesLiving Room, Master Bedroom
Fireplace Y/NYes
FlooringBrick/Stone, Carpet, Marble, Travertine, Hardwood
Furnished Y/NNegotiable
Heating Y/NYes
Interior AmenitiesBuilt-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
Laundry FeaturesLaundry Room
Window FeaturesDrapes, Shutters, Window Treatments

General

Additional Parcels Y/NNo
AppliancesBar 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
Architectural StyleMediterranean
Assoc Fee Paid PerQuarterly
Association AmenitiesCable TV, Gated, Maintenance, Optional Additional Fees, Playground, Security
Association Fee Includes24-Hour Guard, Cable TV, Escrow Reserves Fund, Internet, Maintenance Grounds, Maintenance Repairs, Private Road, Security
Association NameDan O’Connell
Attached Garage Yes
Body of WaterBUTLER CHAIN OF LAKES
Building Area Units0 sqft
Carport Y/NNo
CityWINDERMERE
Community FeaturesAssociation Recreation - Owned, Community Mailbox, Fitness Center, Golf Carts OK, Golf, Playground, Pool, Tennis Court(s)
Construction MaterialsBlock, Stucco
CoolingCentral Air, Zoned
CountyOrange
DirectionsI-4 to Conroy Windermere Road west to Isleworth subdivision. Stay straight on Isleworth Country Club Drive. Estate will be on the Left or Right.
Elementary SchoolWindermere Elem
Facing DirectionEast
Flood Zone CodeX
Flood Zone Code XY
Full Baths5
Garage Spaces4
Garage Y/NYes
HOA Fee$3672
HeatingCentral, Zoned
High SchoolOlympia High
In Law Suite YNNo
Land Lease Y/NNo
Lease Considered Y/NYes
Legal DescriptionN 73 DEG W 204.27 FT S 22 DEG W ALONG LOTS 47 & 48 FOR 146.32 FT TO POB
LevelsTwo
Listing TermsCash, Conventional
Living Area Units0 sqft
Lot Size Square Feet40620
Lot Size UnitsSquare Feet
MLS Area34786 - Windermere
Middle/Junior High SchoolChain of Lakes Middle
Minimum Lease8-12 Months
Monthly HOA Amount$1,224
New ConstructionNo
Occupancy TypeOwner
OwnershipFee Simple
Pets AllowedBreed Restrictions, Yes
Pool FeaturesIn Ground, Lighting
Property SubtypeSingle Family Residence
Property TypeResidential
RoofTile
Security FeaturesClosed Circuit Camera(s), Gated Community, Security Gate, Security Lights, Security System, Smoke Detector(s)
Senior Community Y/NNo
SewerSeptic Tank
Spa FeaturesHeated, In Ground
Standard StatusActive
StatusActive
Subdivision NameISLEWORTH
Tax Annual Amount$57,071
Tax Lot48
Tax Year2026
Total Rooms5
UtilitiesCable Connected, Electricity Connected, Fire Hydrant, Natural Gas Connected, Street Lights, Underground Utilities
ViewGarden, Golf Course, Trees/Woods, Water
Virtual TourClick here
Water Access Y/NNo
Water ViewLake - Chain of Lakes
Water View Y/NYes
Year Built1995
ZoningP-D

Exterior

Building Area Total10,319 sqft
Covered Spaces4
Exterior AmenitiesBalcony, French Doors, Irrigation System, Lighting, Outdoor Grill, Outdoor Shower, Rain Gutters
FencingFenced
Foundation DetailsSlab
Lot FeaturesLandscaped, On Golf Course, Oversized Lot
Lot Size Acres0.93
Lot Size Area40,620 sqft
Parking FeaturesCircular Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Garage
Private PoolYes
Road Frontage TypeStreet Paved, Private Road
Road Surface TypePaved
SpaYes
VegetationMature Landscaping, Trees/Landscaped
Water SourcePublic
Waterfront Y/NNo

Additional Details

Price History

  

Similar Properties

$8,500,000

4 Beds 5 Baths 7,100 SQFT 0.93 Acres
Type: Single Family

5092 ISLEWORTH COUNTRY CLUB DRIVE
WINDERMERE, FL 34786

MLS#: O6446272
Abby Tomassoni
Abby Tomassoni
The Real Estate Advantage
Phone: 763.234.9123
Office: 763.755.1100