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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
Additional Information
Additional Lease Restrictions
Per Isleworth Community Association (ICA)
Additional Parcels YN
false
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
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
Approval Process
Per Isleworth Community Association (ICA)
Architectural Style
Mediterranean
Association Amenities
Cable TV, Gated, Maintenance, Optional Additional Fees, Playground, Security
Association Approval Required YN
1
Association Email
dan.oconnell@Isleworth.com
Association Fee
3672
Association Fee Frequency
Quarterly
Association Fee Includes
Guard - 24 Hour, Cable TV, Escrow Reserves Fund, Internet, Maintenance Grounds, Maintenance, Private Road, Security
Association Fee Requirement
Required
Association YN
true
Attached Garage YN
true
Available For Lease YN
1
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
Carport YN
false
Community Features
Association Recreation - Owned, Community Mailbox, Fitness Center, Golf Carts OK, Golf, Playground, Pool, Tennis Court(s), Street Lights
Construction Materials
Block, Stucco
Cooling
Central Air, Zoned
Country
US
Current Price
8500000.00
Direction Faces
East
Elementary School
Windermere Elem
Exterior Features
Balcony, Lighting, Outdoor Grill, Outdoor Shower, Rain Gutters
Fencing
Fenced
Fireplace Features
Living Room, Primary Bedroom
Fireplace YN
true
Flood Zone Code
X
Flooring
Brick, Carpet, Marble, Travertine, Wood
Foundation Details
Slab
Furnished
Negotiable
Garage Spaces
4
Garage YN
true
Heating
Central, Zoned
High School
Olympia High
Homestead YN
1
Interior Features
Built-in Features, Cathedral Ceiling(s), Ceiling Fans(s), Central Vaccum, Crown Molding, Eat-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
Internet Address Display YN
true
Internet Automated Valuation Display YN
true
Internet Consumer Comment YN
false
Internet Entire Listing Display YN
true
Laundry Features
Laundry Room
Lease Restrictions YN
1
Levels
Two
List AOR
Orlando Regional
Living Area Meters
659.61
Living Area Source
Owner
Living Area Units
Square Feet
Lot Features
Landscaped, On Golf Course, Oversized Lot, Paved, Private
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
2026-10-01T17:31:17.372Z
Monthly HOA Amount
1224.00
New Construction YN
false
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
Breed Restrictions, Yes
Pool Private YN
true
Public Survey Range
28
Public Survey Section
16
RATIO Current Price By Calculated SqFt
1197.18
Realtor Info
As-Is, Assoc approval required, No Sign
Road Surface Type
Paved
Roof
Tile
Room Count
5
Security Features
Closed Circuit Camera(s), Gated Community, Security Gate, Security Lights, Security System, Smoke Detector(s)
Senior Community YN
false
Sewer
Septic Tank
Showing Requirements
24 Hour Notice, Appointment Only, Call Before Showing, Call Listing Agent, Listing Agent Must Accompany, See Remarks
Spa Features
Heated, In Ground
Spa YN
true
Status Change Timestamp
2026-10-01T14:56:20.000Z
Tax Annual Amount
57070.63
Tax Block
00
Tax Book Number
16/118
Tax Legal Description
N 73 DEG W 204.27 FT S 22 DEG W ALONG LOTS 47 & 48 FOR 146.32 FT TO POB
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
Cable Connected, Electricity Connected, Fire Hydrant, Natural Gas Connected, Underground Utilities
Vegetation
Mature Landscaping, Trees/Landscaped
Water Body Name
BUTLER CHAIN OF LAKES
Water Source
Public
Water View
Lake - Chain of Lakes
Water View YN
1
Waterfront YN
false
Window Features
Drapes, Shutters, Window Treatments
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 10/1/26 5:59 PM) |

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