IDX

Listed by Monica Lochmandy · Courtesy of ISLEWORTH REALTY LLC · Agent MLS ID# MFR261067417 · Deemed reliable but not guaranteed. · Listing updated: Sep 16, 2026 · 4:50 PM

5138 FAIRWAY OAKS DR

Windermere, Orange, FL, 34786

Active

$4,999,500

$1155/sqft

4Beds
5Baths
4,330Sq Ft
1994Built
137Days on Market

About this home

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.

Facts & Features

MFRO6401757
$4,999,500
Active
4
5
5
0
4,330 sqft
0.5000
1994
Residential
Single Family Residence
Traditional

Community Information

5138 FAIRWAY OAKS DR
Isleworth
Windermere
Orange
FL
34786
No

Amenities

Cable TV, Gated, Security, Playground
N/A
No
No
Yes

Interior

Ceiling Fans(s), Walk-In Closet(s), Eat-in Kitchen, Living Room/Dining Room Combo, Kitchen/Family Room Combo, Stone Counters, Thermostat, Crown Molding, Solid Surface Counters, Built-in Features
Electric, Natural Gas
Central Air, Zoned
Tile
Family Room
N/A
Dishwasher, Disposal, Dryer, Ice Maker, Microwave, Refrigerator, Washer, Electric Water Heater, Freezer, Range, Range Hood, Exhaust Fan, Bar Fridge, Wine Refrigerator

Exterior

Rain Gutters, Lighting
Block, Stucco
Slab
Tile
Other
Landscaped, Oversized Lot, On Golf Course

School Information

Windermere Elem
Chain Of Lakes Middle
Olympia High

Additional Information

April 25, 2026
137
P-D
Northeast
No

Mortgage Calculator

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This calculator provides estimates for informational purposes only and is not a loan offer, pre-approval, or commitment to lend. Actual rates, payments, and loan terms vary by lender and are subject to credit approval, income/asset verification, and market conditions. Property tax and homeowners insurance shown are estimates and may differ. PMI applies when the down payment is under 20%. For an official Loan Estimate, contact a licensed mortgage lender. ISLEWORTH REALTY LLC is a licensed real estate brokerage, not a mortgage lender. Equal Housing Opportunity.

137 days on market

Listing updated: Sep 16, 2026 · 4:50 PM

Listed by: Monica Lochmandy · 407-230-6888—ISLEWORTH REALTY LLC · 407-909-9000

Updated from Real Estate Market Data

Location

Ahmed ElbatrawyAhmed ElbatrawyEmpire Network Realty

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