← Back to IsleworthACTIVE · MLS MFRO6401757

Windermere, FL · Single Family Residence

5138 Fairway Oaks Dr

$4,999,500
MLS MFRO6401757
4Bedrooms
5Bathrooms
4,330Square feet
0.5Acres

THE SETTING, AND THE DETAILS

A closer look.

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.

Private poolGarage

The details that help you decide.

Details supplied with the listing. Information that was not provided is marked below.

Home essentials
Price per square foot
$1,155
Full bathrooms
5
Half bathrooms
0
Heated living area
4330
Lot size (acres)
0.5
Lot size (sq ft)
21939
Year built
1994
Property type
Residential
Property style
Traditional
Interior & rooms
Interior features
Built-in Features, Ceiling Fans(s), Crown Molding, Eat-in Kitchen, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Solid Surface Counters, Stone Counters, Thermostat, Walk-In Closet(s)
Appliances
Bar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
Flooring
Tile
Additional rooms
Not provided
Land, water & community
Waterfront
No
Waterfront type
Not provided
Water body / lake name
LAKE BRENDA AKA HOURGLASS POND
Water view
Lake,Pond
Dock
No
Dock features
Not provided
Other views
Golf Course, Water
Lot features
Landscaped, On Golf Course, Oversized Lot
Exterior features
Lighting, Rain Gutters
Community amenities
Buyer Approval Required, Community Mailbox, Gated Community - Guard, Golf Carts OK, Playground, Street Lights
Zoning
P-D
Current use
Not provided
Horse amenities
Not provided
Fencing
Other
Other structures
Not provided
Pool, parking & systems
Private pool
Yes
Pool features
Deck, Heated, In Ground
Garage
Yes
Garage spaces
3
Carport
No
Carport spaces
Not provided
Parking features
Circular Driveway, Garage Door Opener, Garage Faces Side
Fireplace
Yes
Fireplace features
Family Room
Heating
Electric, Natural Gas
Cooling
Central Air, Zoned
Water supply
Public
Sewer
Septic Tank
Utilities
Cable Connected, Electricity Connected, Fiber Optics, Natural Gas Connected, Water Connected
Construction
Construction materials
Block, Stucco
Roof
Tile
Foundation
Slab
Stories
Not provided
Levels
One
Location & schools
City
WINDERMERE
Subdivision
ISLEWORTH
County
Orange
ZIP code
34786
Elementary school
Windermere Elem
Middle school
Chain of Lakes Middle
High school
Olympia High
Association, taxes & listing
HOA / association
Yes
Association fee
$3,672
Fee frequency
Quarterly
Included services
Guard - 24 Hour, Cable TV, Escrow Reserves Fund, Internet, Maintenance Grounds, Private Road, Security
Association amenities
Cable TV, Gated, Playground, Security
Additional association fee
Not provided
Additional fee frequency
Not provided
Condo fee
Not provided
Condo fee frequency
Not provided
Annual property taxes
$19,599.37
Tax year
2025
Other annual assessments
Not provided
CDD
No
Listing status
Active
Days on market
137
Listing broker
ISLEWORTH REALTY LLC
MLS number
MFRO6401757

Explore the area

Location supplied with the listing. Confirm boundaries and access for the property.

Listed by ISLEWORTH REALTY LLC · MLS MFRO6401757
Source: mfrmls · Listing updated 2026-09-16 16:50:11 UTC.
Information is deemed reliable but is not guaranteed. Availability and details may change.

Listing photograph

MLS MFRO6401757 · ISLEWORTH REALTY LLC

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