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$3,975,000
New Listing

5050 ISLEWORTH COUNTRY CLUB DRIVE
WINDERMERE, FL 34786

For Sale|Single Family Residence|Active
4
Beds
5
Total Baths
4
Full Baths
1
Partial Bath
3,365
SqFt
$1,181
/SqFt
1987
Built
Subdivision:
ISLEWORTH
County:
Orange
Call Now: 407-495-2546
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407-495-2546
5050 ISLEWORTH COUNTRY CLUB DRIVE5050 ISLEWORTH COUNTRY CLUB DRIVE5050 ISLEWORTH COUNTRY CLUB DRIVE5050 ISLEWORTH COUNTRY CLUB DRIVE
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Monthly Payment (Est.)

$18,136
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Situated on the 6th fairway along the course of Isleworth Golf & Country Club, this updated golf front sparkles with new porcelain tile throughout and modern chandeliers. This single-story residence was renovated in 2020 featuring a new tile roof, fresh paint inside and out, all bathrooms updated and a fully renovated kitchen. Spanning over 3,300 square feet, the 4-bedroom, 4.5-bath is nestled in the heart of Windermere, Florida. The foyer with groin ceiling is light and bright as natural light floods into the home from the glass entryway. Arched details abound in the entrance and this staple in Mediterranean design is carried throughout the estate. Two steps down into the sunken formal living room, the gas fireplace is the centerpiece featuring an artistic stone slab above the hearth and framed by wall-to-wall stacked stone. Completing the space are four large arched windows, two arched doors providing access to the back garden and a built-in dry bar. Situated between the family room and formal living room, and serviced by the nearby kitchen, the formal dining room offers the same illumination of natural sunlight from two large arched windows. The kitchen features new KitchenAid stainless steel appliances, a NXR Pro gas range and built-in 40 bottle Euro Cave wine fridge. The custom cabinetry provides ample storage and tastefully pairs in a dark grey-brown tone with the white tile backsplash, multi-tonal grey to white tile range hood and marble counters with soft neutral veins. The custom cabinetry continues seamlessly into the family room with built-in entertainment center. Down the hall from the kitchen and family room are the guest rooms. The first features an ensuite bathroom and the other two bedrooms are serviced by the hall bath with dual sinks. The hall bath also provides access to the patio and serves as the pool bath. Situated on the opposite end of the home, we find the primary suite, powder bath off the foyer and a flex room. The primary is airy and bright with arched windows, stacked stone fireplace and a dazzling chandelier. The suite features two separate bathrooms – one with walk-in shower and the second with free-standing soaking tub. The walk-in closet offers a warm cedar wood ceiling and custom built-ins. The flex room proposes many uses whether it be an office, nursery, gym, den or library. This stunning property offers a seamless blend of indoor-outdoor living boasting a covered patio with fireplace, open-air pool with spa and views of the fairway. Rounding out the estate is a welcoming circular driveway that extends to the rear motor court with two-car garage plus golf cart parking. Whether hosting or unwinding, this home elevates every moment.

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Listing Snapshot
Price 
$3,975,000
Days On Site 
0 Days
Bedrooms 
4
Inside Area (SqFt) 
3,365 sqft
Total Baths 
5
Full Baths 
4
Partial Baths 
1
Lot Size 
0.52 Acres
Year Built 
1987
MLS® Number 
O6372348
Status 
Active
Property Tax 
$28,793
HOA/Condo/Coop Fees 
$1,043 monthly
Sq Ft Source 
Public Records
Friends & Family
Recent Activity
11 hours agoListing updated with changes from the MLS®
17 hours agoListing first seen on site
General Features
Acres 
0.52
Attached Garage 
Yes
Direction Faces 
Southeast
Foundation 
Block
Garage 
Yes
Garage Spaces 
2
Levels 
One
Parking 
Circular DrivewayDrivewayGarage Door OpenerGarage Faces RearOversizedAttached
Pets 
Breed RestrictionsCats OKDogs OKYes
Property Sub Type 
Single Family Residence
Security 
Gated Community
Sewer 
Septic Tank
SqFt Total 
4843
Utilities 
Natural Gas AvailableCable AvailableElectricity ConnectedNatural Gas ConnectedPhone AvailableUnderground UtilitiesWater Connected
Water Source 
Public
Zoning 
P-D
Interior Features
Appliances 
DishwasherDisposalDryerGas Water HeaterMicrowaveRangeRange HoodRefrigeratorTankless Water HeaterWasherWater SoftenerWine Refrigerator
Cooling 
Central AirZoned
Fireplace 
Yes
Fireplace Features 
Living RoomOutside
Flooring 
Tile
Furnished 
Negotiable
Heating 
CentralElectricZoned
Interior 
Built-in FeaturesEat-in KitchenHigh CeilingsStone CountersWalk-In Closet(s)
Laundry Features 
InsideLaundry Room
Spa 
Yes
Window Features 
BlindsDrapesTinted Windows
Bathroom 1 
Dimensions - 5x7Level - First
Bathroom 4 
Dimensions - 6x13Level - FirstFeatures - Double Vanity, Stone Counters
Bedroom 2 
Dimensions - 12x11Level - FirstFeatures - Stone Counters
Bedroom 3 
Dimensions - 13x11Level - First
Bedroom 4 
Dimensions - 12x12Level - First
Den 
Dimensions - 16x7Level - First
Dining Room 
Dimensions - 12x16Level - First
Family Room 
Dimensions - 13x23Level - First
Kitchen 
Dimensions - 13x23Level - FirstFeatures - Stone Counters
Laundry 
Dimensions - 6x12Level - First
Living Room 
Dimensions - 19x17Level - FirstFeatures - Bar
Master Bathroom 
Level - FirstFeatures - Stone Counters
Master Bedroom 
Dimensions - 20x20Level - First
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Exterior Features
Construction Details 
BlockStucco
Exterior 
LightingRain Gutters
Fencing 
Fenced
Lot Features 
PrivateOn Golf CoursePavedLandscaped
Patio And Porch 
CoveredRear Porch
Pool Features 
GuniteTilePrivate
Private Pool 
Yes
Roof 
TileConcrete
Spa 
Yes
Spa Features 
In Ground
View 
Golf Course
Waterview 
Golf Course
Windows/Doors 
BlindsDrapesTinted Windows
Community Features
Association Amenities 
Basketball CourtCable TVGatedPlaygroundSecurity
Association Dues 
3129
Community Features 
GatedClubhouseFitness CenterGolfPlaygroundPoolRestaurantTennis Court(s)Street Lights
Financing Terms Available 
CashConventional
HOA Fee Frequency 
Quarterly
MLS Area 
34786 - Windermere
Roads 
Asphalt
Township 
23
Schools
School District
Unknown
Elementary School
Windermere Elem
Middle School
Chain of Lakes Middle
High School
Olympia High
Listing courtesy of COMPASS FLORIDA LLC (904) 449-2184



Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2026, Stellar MLS.
Last checked: 2026-01-10 05:34 PM EST

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
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