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5138 FAIRWAY OAKS DR, WINDERMERE, FL - photo 1

$4,999,500

5138 FAIRWAY OAKS DR

WINDERMERE, FL 34786

Estimated payment $29,527/month

includes HOA $3,672/mo · estimated tax · estimated insurance · 20% down, 6.5%, 30 yr

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4Beds
5Baths
4,330Sq Ft
$1155Price/Sq Ft

Preferred partner

Kinsfolk Realty

Kinsfolk Signature Realty

Powered by Hometrino

(813) 602-0498

Highlights

HOA $3,672/mo
Private Pool
Fireplace
Garage
Built in 1994
21,939 sqft Lot

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.

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Facts & features

Bedrooms & bathrooms

  • •Bedrooms:4
  • •Bathrooms:5
  • •Full bathrooms:5
  • •Half bathrooms:0

Heating

  • •Has Heating:Yes

Interior area

  • •Total structure area:4,330 sqft
  • •Total interior livable area:4,330 sqft

Parking

  • •Parking features:N/A
  • •Garage spaces:0
  • •Has attached garage:No

Lot

  • •Size:21,939 sqft

Details

  • •Parcel number:N/A

Type & style

  • •Home type:Single Family Residence
  • •Property subtype:Residential

Materials

  • • N/A

Condition

  • •Year built:1994

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Price history

DateEventPrice
2026-04-25T00:00:00.000ZListed for sale$4,999,500$1155/sqft

Listing Agent

Monica Lochmandy

ISLEWORTH REALTY LLC

Brokerage Phone: 407-909-9000

Source: Stellar MLS · MLS #O6401757

Data Powered by Home Junction, Inc.

Nearby

Schools

CENTRAL FLORIDA POLYTECHNIC ACADEMY

Elementary · 1.4 mi

CHAIN OF LAKES MIDDLE

High · 1.6 mi

OLYMPIA HIGH

High · 1.8 mi

Supermarkets

Tim's Wine Market

0.9 mi

Publix

1.3 mi

Walmart Grocery Pickup

1.6 mi

Dining

Tavistock Champions Grill

0.5 mi

Pizza 14

0.7 mi

Dixie Cream Cafe

0.8 mi

Parks

Fernwood Park

0.7 mi

Johnson Park

0.7 mi

Egret Isle Sanctuary

0.7 mi

Beaches

Conrad Beach

5.3 mi

West Beach

5.3 mi

East Beach

5.3 mi

Nearby amenity locations include data © OpenStreetMap contributors.