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5243 Isleworth Country Club Drive, Windermere, FL

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$5,325,000

($829/sqft)

List Status: Active
5243 Isleworth Country Club Drive
Windermere, FL 34786


4 beds
5 baths
6424 living sqft
Top Features
  • View: Water, Golf Course
  • Subdivision: Isleworth
  • Built in  1992
  • Single Family Residence
Description
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 stain
Property Details
Additional Information
Additional Lease Restrictions
Contact the Isleworth Community Association (ICA); Minimum 1 year lease required
Additional Parcels YN
false
Additional Rooms
Attic, Breakfast Room Separate, Den/Library/Office, Family Room, Great Room, Loft, Media Room, Storage Rooms
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
Bar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
Approval Process
Contact the Isleworth Community Association (ICA); Minimum 1 year lease required
Architectural Style
Custom, Mediterranean
Association Amenities
Gated, Park, Security
Association Approval Required YN
1
Association Email
Dan.oconnell@isleworth.com
Association Fee
3129
Association Fee Frequency
Quarterly
Association Fee Includes
Guard - 24 Hour, Management, Private Road, Security
Association Fee Requirement
Required
Association URL
isleworth.com
Association YN
true
Attached Garage YN
true
Available For Lease YN
1
Bathrooms Total Integer
6
Building Area Source
Public Records
Building Area Total
7246
Building Area Total Srch SqM
673.18
Building Area Units
Square Feet
Calculated List Price By Calculated SqFt
828.92
Carport YN
false
Community Features
Buyer Approval Required, Deed Restrictions, Gated Community - Guard, Golf Carts OK, Golf, Park, Street Lights
Construction Materials
Block, Stucco
Cooling
Central Air, Zoned
Country
US
Cumulative Days On Market
19
Current Price
5325000.00
Direction Faces
North
Elementary School
Windermere Elem
Exterior Features
French Doors, Lighting, Outdoor Kitchen, Storage
Fencing
Fenced, Other
Fireplace Features
Gas, Living Room, Outside
Fireplace YN
true
Flood Zone Code
X
Flood Zone Date
2009-09-25
Flood Zone Panel
12095C0385F
Flooring
Carpet, Marble, Tile, Wood
Foundation Details
Slab
Furnished
Unfurnished
Garage Dimensions
31x24
Garage Spaces
3
Garage YN
true
Heating
Central, Electric, Zoned
High School
Olympia High
Home Warranty YN
false
Homestead YN
1
Interior Features
Built-in Features, Ceiling Fans(s), Central Vaccum, Coffered Ceiling(s), Crown Molding, Eat-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
Internet Address Display YN
true
Internet Automated Valuation Display YN
true
Internet Consumer Comment YN
true
Internet Entire Listing Display YN
true
Laundry Features
Inside
Lease Restrictions YN
1
Levels
Two
List AOR
Orlando Regional
Living Area Meters
596.81
Living Area Source
Estimated
Living Area Units
Square Feet
Lot Features
In County, Level, On Golf Course, Paved
Lot Size Acres
0.51
Lot Size Square Feet
22199
Lot Size Square Meters
2062
Middle Or Junior School
Chain of Lakes Middle
Minimum Lease
1-2 Years
Modification Timestamp
2025-10-29T01:10:09.405Z
Monthly HOA Amount
1043.00
New Construction YN
false
Number Of Septics
1
Occupant Type
Owner
Other Equipment
Irrigation Equipment
Other Structures
Outdoor Kitchen
Ownership
Fee Simple
Parcel Number
28-23-16-3899-02-310
Patio And Porch Features
Covered, Porch, Rear Porch
Pet Restrictions
Refer to ICA Documents
Pets Allowed
Yes
Planned Unit Development YN
1
Pool Private YN
true
Postal Code Plus 4
8900
Public Survey Range
28
Public Survey Section
16
RATIO Current Price By Calculated SqFt
828.92
Realtor Info
As-Is, Brochure Available, No Sign
Road Responsibility
Private Maintained Road
Road Surface Type
Asphalt
Roof
Tile
Room Count
11
Security Features
Closed Circuit Camera(s), Gated Community, Security System, Security System Owned, Smoke Detector(s), Touchless Entry
Senior Community YN
false
Sewer
Septic Tank
Showing Requirements
Listing Agent Must Accompany, ShowingTime
Spa YN
false
Status Change Timestamp
2025-10-09T21:54:45.000Z
Tax Annual Amount
50194
Tax Block
2
Tax Book Number
16-118
Tax Legal Description
ISLEWORTH 16/118 LOT 231
Tax Lot
231
Tax Year
2024
Total Acreage
1/2 to less than 1
Total Annual Fees
12516.00
Total Monthly Fees
1043.00
Township
23
Universal Property Id
US-12095-N-282316389902310-R-N
Unparsed Address
5243 ISLEWORTH COUNTRY CLUB DR
Utilities
Cable Connected, Natural Gas Connected, Underground Utilities, Water Connected
Vegetation
Mature Landscaping, Oak Trees
Water Access
Lake - Chain of Lakes
Water Access YN
1
Water Body Name
LAKE CHASE
Water Extras
Boat Ramp - Private, Skiing Allowed
Water Extras YN
1
Water Source
Public
Water View
Lake - Chain of Lakes
Water View YN
1
Waterfront YN
false
Window Features
Blinds, Insulated Windows, Shutters, Thermal Windows
Zoning
P-D
Zoning Compatible YN
1
Neighborhood Map
Popup

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MLS #MFRO6348067 Listing courtesy of Stockworth Realty Group 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 10/28/25 4:55 PM) |

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