5050 ISLEWORTH COUNTRY CLUB DRIVE Windermere, FL $ 3,975,000
5050 ISLEWORTH COUNTRY CLUB DRIVE
$ 3,975,000
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5050 ISLEWORTH COUNTRY CLUB DRIVE

Windermere, FL, 34786
$ 3,975,000
Bedrooms4 Baths4.1 Sq 3,365

Monthly Estimate*

$ 24,475

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Single Family Home for sale in Windermere, FL

for $3,975,000 with 4 bedrooms and 4 full baths, 1 half bath. This 3,365 square foot home was built in 1987 on a lot size of 0.52.

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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Single Family Active

Price

$ 3,975,000

Bedrooms

4

Full Bath

4

Half Bath

1

Property Type

Single Family

Taxes

$ 28,793

Style

Single Family Residence

Lot Size

0.52

Year Built

1987

Town/City

Windermere

County/Region

Orange

MLS | Web ID

O6372348

Features
General
Sewer Septic Tank
Heating Central Electric Zoned
Cooling Central Air Zoned
Utilities BB/HS Internet Available Cable Available Electricity Connected Natural Gas Connected Phone Available Public Sprinkler Meter Street Lights Underground Utilities Water Connected
Possession Close Of Escrow
Roof Tile Concrete
Appliances Dishwasher Disposal Dryer Gas Water Heater Microwave Range Range Hood Refrigerator Tankless Water Heater Washer Water Softener Wine Refrigerator
Zoning P-D
HOA Fee 3129
Garage Spaces 2
Association Fee Includes 24-Hour Guard Cable TV Escrow Reserves Fund Maintenance Grounds Maintenance Repairs Private Road Security
Patio/Porch Features Covered Rear Porch
Pool Features Gunite Tile
Security Features Gated Community
Construction Materials Block Stucco
Pets Allowed Breed Restrictions Cats OK Dogs OK Yes
Year Built 1987
View Golf Course
Levels One
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
Waterfront Features Lake Waterfront
Community Features Community Boat Ramp Lake Water Access Waterfront Association Recreation - Owned Clubhouse Community Mailbox Fitness Center Gated Community - Guard Golf Carts OK Golf Irrigation-Reclaimed Water Playground Pool Restaurant Special Community Restrictions Tennis Court(s)
Assoc Fee Paid Per Quarterly
County Orange
New Construction false
Property Type Residential
Association Amenities Basketball Court Cable TV Fence Restrictions Gated Optional Additional Fees Playground Security Vehicle Restrictions
Attached Garage true
Subdivision Name ISLEWORTH
Facing Direction Southeast
Garage Y/N true
Total Rooms 13
Full Baths 4
Status Active
Directions I-4 to Conroy Windermere Road west to Isleworth subdivision on the left. From Isleworth Country Club Drive home is on the right.
High School Olympia High
City WINDERMERE
Association Name Dan O'Connell
Senior Community Y/N false
MLS Area 34786 - Windermere
Lot Size Units Square Feet
Lot Size Square Feet 22514
Carport Y/N false
Listing Terms Cash Conventional
Spa Features In Ground
Elementary School Windermere Elem
Property Attached Y/N false
Land Lease Y/N false
Tax Annual Amount 28793
Middle/Junior High School Chain of Lakes Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://vimeo.com/1152694715/11acf9d015?fl=pl&fe=sh
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Owner
Tax Lot 41
Legal Description ISLEWORTH 16/118 LOT 41
Minimum Lease 7 Months
Water Access Y/N false
Monthly HOA Amount 1043
Additional Rooms Den/Library/Office Formal Dining Room Separate Formal Living Room Separate
Water View Y/N false
Flood Zone Code X
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Interior
Interior Amenities Built-in Features Central Vacuum Eating Space In Kitchen High Ceilings Kitchen/Family Room Combo Primary Bedroom Main Floor Solid Wood Cabinets Stone Counters Walk-In Closet(s) Window Treatments
Flooring Porcelain Tile
Furnished Y/N Negotiable
Fireplace Features Living Room Outside Master Bedroom
Air Conditioning Y/N true
Heating Y/N true
Window Features Blinds Drapes Rods Shades Tinted Windows
Fireplace Y/N true
Half Baths 1
Laundry Features Inside Laundry Room
Total Bedrooms 4
Total Baths 5
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Exterior
Exterior Amenities Irrigation System Lighting Rain Gutters Sliding Doors Sprinkler Metered
Vegetation Mature Landscaping Oak Trees
Fencing Fenced
Parking Features Golf Cart Parking Circular Driveway Driveway Garage Door Opener Garage Faces Rear Oversized
Lot Features On Golf Course In County Landscaped
Water Source Public
Lot Size Area 22514
Foundation Details Block
Spa true
Building Area Total 4843
Lot Dimensions 190 x 151 x 128 x 145
Lot Size Acres 0.52
Road Surface Type Paved Asphalt
Private Pool true
Waterfront Y/N false
Covered Spaces 2
Road Frontage Type Private Road Street Paved
Road Responsibility Private Maintained Road
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* Excluded Features
List By
Compass Florida Llc

Broker

toni.cafferty@compass.com

Email

Affordability Calculator

$26,874
Per Month
91%
9%
0%
Monthly Principal & Interest
$24,475
Monthly Property Taxes
$2,399
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Olympia High High School High School
Pricing History
DatePricePrice ChangeDescription
1/10/2026$3,975,000 Listed Price

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5050 ISLEWORTH COUNTRY CLUB DRIVE, Windermere, FL, 34786 is a Single Family Home for sale at $3,975,000 with 3,365 sqft and a lot size of 0.52. 5050 ISLEWORTH COUNTRY CLUB DRIVE has 4 bedrooms, 4.1 baths, and was built in 1987. The property's zip code is 34786 which is in Windermere, FL