Curious about this home?

Ask anything — no agents, no pressure

Try asking

About This Home

This 4-bedroom, 5-bathroom single family at 5138 FAIRWAY OAKS DR in Windermere, FL is listed for $5,500,000 ($1,270 per sqft). Built in 1994, the home offers 4,330 sqft of living space on a 0.50 acres lot.

Agent Description

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.

Key Features

  • Built in 1994
  • 0.50 acre lot
  • Private pool
  • Fireplace

Property Details

5 full
1994

Amenities

PoolFireplace

Monthly Cost Estimate

$29,415/mo

20% down · 6.5% · 30 years

Principal$3,978
Interest$23,833
Insurance$1,604

Estimates only. Actual payments may vary.

Location

5138 FAIRWAY OAKS DR

Windermere, FL 34786

ISLEWORTH

Features & Amenities

Interior Features

Built-in FeaturesCeiling Fans(s)Crown MoldingEat-in KitchenKitchen/Family Room ComboLiving Room/Dining Room ComboSolid Surface CountersStone CountersThermostatWalk-in Closet(s)

Exterior Features

French DoorsLightingRain GuttersPool

Property Details

Flooring

Tile

Construction

BlockStucco

Parking

DrivewayGarageGarage - Attached

Heating

Electric (Heating)Fireplace(s)Natural Gas

Cooling

Central AirZoned

Appliances

DishwasherDryerFreezerGarbage DisposerIce MakerMicrowaveRangeRefrigeratorRefrigerator - Wine StorageWasher

Questions & Answers

This 4-bedroom, 5-bathroom single family at 5138 FAIRWAY OAKS DR is listed at $5,500,000 ($1,270/sqft). The estimated monthly payment is $23,833 based on 20% down at 6.5% interest.

Key features include: Built in 1994, 0.50 acre lot, Private pool, Fireplace. Interior Features: Built-in Features, Ceiling Fans(s), Crown Molding. Exterior Features: French Doors, Lighting, Rain Gutters.

This property is listed by Monica Lochmandy and can be reached at 4072306888 or mlochmandy@isleworth.com.

ML

Monica Lochmandy

Agent at ISLEWORTH REALTY LLC

(407) 230-6888

Listed by ISLEWORTH REALTY LLC · View on Broker Site

MLS# O6401757· Source: listhub· Updated 39 days ago

Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

5138 FAIRWAY OAKS DR, Windermere, FL 34786

Open this listing in: