Map

For SaleSingle Family ResidenceActive

5050 Isleworth Country Club Drive

Windermere, FL 34786

$3,189,000

69 Days On Site

  • 4Beds
  • 5Baths4 full, 1 half
  • 3,365Sq Ft
  • $948Per Sq Ft
  • 0.52Acres
  • 1987Built
Subdivision
Isleworth
County
Orange
MLS®
O6438618

Overview

Positioned along the 6th fairway of Isleworth Golf & Country Club, this thoughtfully updated single-story residence offers a rare combination of privacy, golf-course views and effortless everyday living. A welcoming circular drive and mature oaks set the stage, while inside, nearly 3,400 square feet unfolds in a light-filled collection of spaces designed to feel equally comfortable for quiet evenings at home or a house full of guests.

Natural light pours through the glass entry into a dramatic foyer with a groin-vaulted ceiling, introducing the architectural character found throughout the home. Arched openings lead into the formal living room, where a striking stone fireplace creates a natural gathering place and walls of glass frame views of the garden and fairway beyond. The formal dining space provides an elegant backdrop for entertaining while remaining connected to the heart of the home.

The renovated kitchen is both inviting and exceptionally functional, featuring a professional-style gas range, integrated appliances and a 40-bottle wine refrigerator. Custom cabinetry, marble countertops and a distinctive tile range hood complete the space, while additional cabinetry flows seamlessly into the family room to create a built-in entertainment center. Natural light reflects beautifully across the large-format tile floors, creating a bright, cohesive feel from room to room.

The primary suite is privately positioned on the northeast wing, welcoming golden morning light into the space. The retreat features a distinctive dual-bath arrangement—one with a walk-in shower and the other with a freestanding soaking tub—along with a cedar-lined walk-in closet with custom built-ins. Three additional bedrooms provide comfortable accommodations for family and guests, including one with an ensuite bath, while the updated hall bath offers dual sinks and convenient pool access. A separate flex room easily adapts as an office, library, fitness room or additional retreat.

Outside, a covered patio with fireplace extends the living space year-round, overlooking the open-air pool and spa with the manicured fairway beyond. A rear motor court, two-car garage and dedicated golf-cart parking complete the property. Recent improvements, including a 2020 slate roof, refreshed exterior paint, renovated kitchen and baths, complement the home’s established character. With its single-story footprint, private setting and half-acre golf-course homesite, the opportunity is as compelling as the lifestyle within the gates.

Listing Snapshot

Price
$3,189,000
Days On Site
69 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
O6438618
Status
Active
Property Tax
$28,793 (2025)
HOA/Condo/Coop Fees
$1,224 monthly
Sq Ft Source
Public Records

Property Details

General Features

16 items
Acres
0.52
Attached Garage
Yes
Direction Faces
Southeast
Foundation
Block
Garage
Yes
Garage Spaces
2
Levels
One
Parking
Circular Driveway, Driveway, Garage Door Opener, Garage Faces Rear, Oversized, Attached
Pets
Breed Restrictions, Cats OK, Dogs OK, Yes
Property Sub Type
Single Family Residence
Security
Gated Community
Sewer
Septic Tank
SqFt Total
4,843
Utilities
Natural Gas Available, Cable Available, Electricity Connected, Natural Gas Connected, Phone Available, Underground Utilities, Water Connected
Water Source
Public
Zoning
P-D

Interior Features

24 items
Appliances
Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Water Softener, Wine Refrigerator
Cooling
Central Air, Zoned
Fireplace
Yes
Fireplace Features
Living Room, Outside
Flooring
Tile
Furnished
Negotiable
Heating
Central, Electric, Zoned
Interior
Built-in Features, Eat-in Kitchen, High Ceilings, Stone Counters, Walk-In Closet(s)
Laundry Features
Inside, Laundry Room
Spa
Yes
Window Features
Blinds, Drapes, Tinted Windows

Rooms

RoomDimensionsLevelFeatures
Bathroom 15x7First
Bathroom 46x13FirstDouble Vanity, Stone Counters
Bedroom 212x11FirstStone Counters
Bedroom 313x11First
Bedroom 412x12First
Den16x7First
Dining Room12x16First
Family Room13x23First
Kitchen13x23FirstStone Counters
Laundry6x12First
Living Room19x17FirstBar
Master BathroomFirstStone Counters
Master Bedroom20x20First

Exterior Features

13 items
Construction Details
Block, Stucco
Exterior
Lighting, Rain Gutters
Fencing
Fenced
Lot Features
Landscaped, On Golf Course, Paved, Private
Patio And Porch
Covered, Rear Porch
Pool Features
Gunite, Tile, Private
Private Pool
Yes
Roof
Concrete, Tile
Spa
Yes
Spa Features
In Ground
View
Golf Course
Waterview
Golf Course
Windows/Doors
Blinds, Drapes, Tinted Windows

Community Features

8 items
Association Amenities
Basketball Court, Cable TV, Gated, Playground, Security
Association Fee
$3672.0
Association Fee Frequency
Quarterly
Community Features
Gated, Clubhouse, Fitness Center, Golf, Playground, Pool, Restaurant, Tennis Court(s), Street Lights
MLS Area
34786 - Windermere
Township
23
Financing Terms Available
Cash, Conventional
Roads
Asphalt

Location

5050 Isleworth Country Club Drive, Windermere, FL 34786 · 34786 - Windermere

Neighborhood & Commute

ZIP Code 34786

Median household income
$127,371
Income per person
$64,053
Households
17,419
Average household size
2.82
Median age
38.9

Source: Walk Score.

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

Schools

Elementary School
Windermere Elem
Middle School
Chain of Lakes Middle
High School
Olympia High

Price & Status History

  1. Listing updated with changes from the MLS®
  2. Listing first seen on site
  3. Price changed to $3,189,000
  4. Status changed to Active

Friends & Family

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Listing courtesy of COMPASS FLORIDA LLC (904) 449-2184

Stellar MLS

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: 2026-11-12 08:44 PM EST

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