Virtual TourMap

For SaleSingle Family ResidenceActive

5138 Fairway Oaks Dr

Windermere, FL 34786

$4,999,500

204 Days On Site

  • 4Beds
  • 5Baths5 full
  • 4,330Sq Ft
  • $1,155Per Sq Ft
  • 0.5Acres
  • 1994Built
Subdivision
Isleworth
County
Orange
MLS®
O6401757

Overview

Set along Isleworth’s signature 12th fairway, this fully reimagined estate captures the essence of refined golf course living within the renowned Isleworth Golf & Country Club—recognized among the finest private club communities in the world. Encompassing more than 4,300 square feet, the single-story residence has been completely transformed inside and out. Thoughtfully redesigned interiors showcase all-new flooring throughout, beautifully renovated bedrooms and baths, and a striking glass-enclosed wine tower serving as a true centerpiece that is both functional and an unforgettable conversation element anchoring the main living spaces. Every detail throughout the home has been elevated, from designer lighting installations that bring character and sophistication to each room, to the seamless flow of living and entertaining spaces. The kitchen is a true showpiece, featuring all-new appliances—including a striking black range with matching hood, refrigerator, and microwave—all accented with elegant gold detailing for a bold, designer-forward statement. Custom cabinetry is paired with exquisite countertops, highlighted by a dramatic waterfall-edge island that anchors the space and seamlessly blends everyday functionality with elevated, modern style.The outdoor living area features a reimagined pool and all-new pool deck creating a resort-style setting, perfectly positioned to take in breathtaking sunsets over the golf course and water. The half-acre homesite has been thoughtfully cleared and fenced to maximize both privacy and panoramic views, offering an exceptional backdrop for everyday living and entertaining alike. Framed by the fairways, the residence captures views of Lake Brenda - also known as Hourglass Pond - a small, privately maintained 10-acre water body that serves as a peaceful and picturesque part of the community setting. Additional features include a home office, in-home laundry room, and a three-car garage. Residents of Isleworth enjoy an unparalleled lifestyle surrounded by the Butler Chain of Lakes, with access to world-class golf, dining, and amenities, all just moments from Central Florida’s premier shopping, dining, and entertainment destinations.

Listing Snapshot

Price
$4,999,500
Days On Site
204 Days
Bedrooms
4
Inside Area (SqFt)
4,330 sqft
Total Baths
5
Full Baths
5
Partial Baths
0
Lot Size
0.5 Acres
Year Built
1994
MLS® Number
O6401757
Status
Active
Property Tax
$19,599.37 (2025)
HOA/Condo/Coop Fees
$1,224 monthly
Sq Ft Source
Public Records

Property Details

General Features

17 items
Acres
0.5
Attached Garage
Yes
Direction Faces
Northeast
Foundation
Slab
Garage
Yes
Garage Spaces
3
Levels
One
Parking
Circular Driveway, Garage Door Opener, Garage Faces Side, Attached
Pets
Breed Restrictions
Property Sub Type
Single Family Residence
Security
Gated Community, Security Gate
Sewer
Septic Tank
SqFt Total
5,911
Style
Traditional
Utilities
Cable Available, Natural Gas Available, Cable Connected, Electricity Connected, Natural Gas Connected, Water Connected
Water Source
Public
Zoning
P-D

Interior Features

23 items
Appliances
Bar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
Cooling
Central Air, Zoned
Fireplace
Yes
Fireplace Features
Family Room
Flooring
Tile
Furnished
Furnished
Heating
Electric, Natural Gas
Interior
Built-in Features, Crown Molding, Eat-in Kitchen, Stone Counters, Walk-In Closet(s)
Laundry Features
Inside, Laundry Room
Spa
Yes

Rooms

RoomDimensionsLevelFeatures
Bathroom 2FirstDescription - Room4
Bathroom 3FirstDescription - Room6
Bathroom 4FirstDescription - Room8
Bedroom 2FirstDescription - Room3
Bedroom 3FirstDescription - Room5
Bedroom 4FirstDescription - Room7
Dining RoomFirstDescription - Room12
Family RoomFirstDescription - Room10
KitchenFirstDescription - Room9
Living RoomFirstDescription - Room11
Master BathroomFirstDescription - Room2
Master BedroomFirstDescription - Room1
OfficeFirstDescription - Room13

Exterior Features

13 items
Construction Details
Block, Stucco
Exterior
Lighting, Rain Gutters
Fencing
Other
Lot Features
Landscaped, On Golf Course
Patio And Porch
Covered, Rear Porch
Pool Features
Heated, In Ground, Private
Private Pool
Yes
Roof
Tile
Spa
Yes
Spa Features
Heated, In Ground
View
Lake, Pond, Water, Golf Course
Waterfront Features
LAKE BRENDA AKA HOURGLASS POND
Waterview
Lake, Pond, Water, Golf Course

Community Features

8 items
Association Amenities
Cable TV, Gated, Playground, Security
Association Fee
$3672.0
Association Fee Frequency
Quarterly
Community Features
Gated, Playground, Street Lights
MLS Area
34786 - Windermere
Township
23
Financing Terms Available
Cash, Conventional
Roads
Paved

Location

5138 Fairway Oaks Dr, 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. Status changed to Active
  3. Price changed to $4,999,500
  4. Listing first seen on site

Friends & Family

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Listing courtesy of ISLEWORTH REALTY LLC (407) 230-6888

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: 2026-11-15 12:37 PM EST

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