5243 ISLEWORTH COUNTRY CLUB DRIVE
WINDERMERE, FL, 34786

Price$5,325,000
Beds4
Baths6
SqFt6,424

Status:Active
Property Type:Residential
School:
Presenting a magnificent Isleworth golf front estate with sweeping lake views, perched above holes #2 and #9 and Lake Chase, combining a completely reimagined interior with designer elegance and modern grand style. With no neighbors on three sides, this stunning home offers a unique combination of privacy mixed with rare golf and water vistas. Home recently underwent a major “spare no expense” remodel by McNally Construction and design by Debby Dearth of McNally Design using the highest quality materials combining the latest designs with timeless Mediterranean architecture. Enter to an impressive foyer and Great Room with soaring 20-foot ceilings above and basket weaved marble and wood flooring below, complemented by wood beams, stone gas fireplace with marble mantle, and shimmering chandeliers. An adjacent cocktail bar next to the dining room is fitted with Cristallo quartzite counters and a temperature-controlled wine cellar that can easily accommodate 700+ bottles of wine. The well-appointed chef’s kitchen is fully equipped with a large center island, custom wood cabinetry, Italian dolomite counter tops, Sub Zero refrigerator, and a Wolf gas range with griddle. Family room and breakfast nook are perfectly sized for everyday entertaining with vaulted ceilings, reclaimed wood floors, and access to the pool patio and summer kitchen cabana. The dramatic first floor primary retreat features picturesque windows and a luxurious spa-like bath complete with chandelier, breakfast bar with Sub Zero fridge, dual vanities, garden tub, glass shower, and French doors to a walled outdoor space. The master closet provides access to a discrete room at the top of a spiral staircase that can be a gym, second study, or hidden Pilates room. Up the main staircase are three additional bedroom suites and a movie theater. An executive office is located on the first floor. Exterior living spaces feature a large covered lanai, heated saltwater pool, full pool bath, summer kitchen with stainless steel grill, sink, beverage refrigerator, custom-built stacked stone outdoor fireplace, and nearly 300 feet of golf frontage. Notable upgrades done in 2023 include a brand new tile roof, replacement of all custom doors and windows, remodeled kitchen, bathrooms with Kohler fixtures, door hardware, cocktail bar, flooring, Control 4 smart house features for lighting, electric shades, cameras, HVAC, pool equipment, garage doors, locks, built-in sound system, pool resurface, new pool heater, landscaping, complete interior and exterior paint, and exterior gray pavers. Home is built with concrete construction on both first and second floors. The 600-acre Isleworth community, surrounding the Butler Chain of Lakes, is a residential enclave that sets the standard of excellence for Central Florida living. Isleworth Golf & Country Club, which is located within the community, is recognized as one of the Top 100 Platinum Clubs of the World offering separate membership opportunities that provide access to golf, tennis, fitness, Clubhouse dining and social events, swimming in the resort-style pool and sundeck, dock, and an abundance of activities. Enjoy a lifestyle defined by casual elegance in a setting that sets the standard for luxury living.

Listing provided by: STOCKWORTH REALTY GROUP, Rob Rahter

Source: Stellar MLS, MLS#: O6348067

Price $5,325,000
Bedrooms 4
Full Baths 5
Half Baths 1
Total Baths 6
Property Style Custom, Mediterranean
Lot Size Area 22199
Lot Size Area Units Square Feet
Acres 0.51
Property Type Residential
Sub type Single Family Residence
MLS Sub type Single Family Residence
Features Built-in Features, Ceiling Fan(s), Central Vacuum, Coffered Ceiling(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Stone Counters, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s), Wet Bar, Window Treatments
Exterior Features French Doors, Irrigation System, Lighting, Outdoor Kitchen, Storage
Year Built 1992
Subdivision ISLEWORTH
View Golf Course, Water
Roof Tile
Waterfront LAKE CHASE
Heating Central, Electric, Zoned
Foundation Slab
Lot Description In County, Level, On Golf Course
Laundry Features Inside
Pool features Heated, In Ground, Salt Water
Parking Description Circular Driveway, Garage Faces Side, Golf Cart Garage
Garage spaces 3
Association Name Dan O’Connell
Association Fee 3672
Association Amenities Gated, Park, Security
Directions From I-4, take Conroy Road West. From Apopka Vineland Rd and Conroy Windermere Roads, go west on Conroy Windermere into Windermere. Left into Isleworth. After guard house, go straight on Isleworth Country Club Drive. House is on the left.
County Orange
Latitude 28.481
Longitude -81.524382
Market Area 34786 – Windermere
Address 5243 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, FL 34786
Postal Code 34786
City WINDERMERE
State FL
Country United States
Listing Office STOCKWORTH REALTY GROUP
Listing Office Phone 407-909-5900
Listing Agent Rob Rahter
Listing Agent Phone 407-497-4526
Special listing conditions None
Ownership Fee Simple
Terms Cash, Conventional
Virtual Tour URL https://www.propertypanorama.com/instaview/stellar/O6348067
Elementary School Windermere Elem
Middle School Chain of Lakes Middle
High School Olympia High
Days on market 142
MLS Status Active
Listing Date Oct 9, 2025
Listing Last Modified Feb 28, 2026
Tax ID 282316389902310
Tax Year 2024
Tax Annual Amount 50194
MLS Area 34786 – Windermere
MLS # O6348067

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