5138 FAIRWAY OAKS DR WINDERMERE FL 34786 MLS #O6401757

5138 FAIRWAY OAKS DR
WINDERMERE, FL, 34786
$5,500,000
4 Beds
5 Baths
4,330 SqFt
0.5 Acres
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MLS #O6401757 image #0
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.

Property Details

Price:
$5,500,000
MLS #:
O6401757
Status:
Active
Beds:
4
Baths:
5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
ISLEWORTH
Neighborhood:
34786windermere
Listed Date:
Apr 25, 2026
Finished Sq Ft:
4,330
Total Sq Ft:
5,911
Lot Size:
21,939 sqft / 0.50 acres (approx)
Year Built:
1994
TraditionalPoolCommunity Gated34786 – Windermere34786windermereIsleworthWindermere ElemChain Of Lakes MiddleOlympia HighLake Brenda Aka Hourglass PondPer Isleworth Community Association (ica)8-12 MonthsBreed Restrictions

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Schools

Elementary School:
Windermere Elem
Middle School:
Chain of Lakes Middle
High School:
Olympia High

Interior

Appliances
Bar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
Bathrooms
5 Full Bathrooms
Cooling
Central Air, Zoned
Flooring
Porcelain Tile
Heating
Electric, Natural Gas
Interior Features
Built-in Features, Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Solid Surface Counters, Stone Counters, Thermostat, Walk-In Closet(s)
Laundry Features
Corridor Access, Inside, Laundry Room
Levels
One

Exterior

Architectural Style
Traditional
Association Amenities
Cable TV, Gated, Playground, Security
Attached Garage YN
1
Community Features
Community Boat Ramp, Water Access, Buyer Approval Required, Community Mailbox, Gated Community – Guard, Golf Carts OK, Playground
Construction Materials
Block, Stucco
Covered Spaces
3
Direction Faces
Northeast
Exterior Features
French Doors, Lighting, Rain Gutters
Fencing
Other
Garage Spaces
3
Lot Features
Landscaped, On Golf Course, Oversized Lot
Open Parking YN
1
Parking Features
Circular Driveway, Garage Door Opener, Garage Faces Side
Patio And Porch Features
Covered, Rear Porch
Roof
Tile
Security Features
Gated Community, Security Gate
Spa Features
Heated, In Ground
View
Golf Course, Water

Financial

HOA Fee
$3,672
HOA Fee Frequency
Quarterly
HOA Includes
24-Hour Guard, Cable TV, Escrow Reserves Fund, Internet, Maintenance Grounds, Private Road, Security
HOA Name
Dan O’Connell
HOA Phone
407-909-2071
Tax Year
2025
Taxes
$19,599

Map

Community

Subdivisions in WINDERMERE

Market Summary

Current real estate data for Single Family in WINDERMERE as of Apr 27, 2026
290
Single Family Listed
98
Avg DOM
460
Avg $ / SqFt
$2,237,531
Avg List Price

Property Summary

    Located in the ISLEWORTH subdivision, 5138 FAIRWAY OAKS DR WINDERMERE FL is a Single Family for sale in WINDERMERE, FL, 34786. It is listed for $5,500,000 and features 4 beds, 5 baths, and has approximately 4,330 square feet of living space, and was originally constructed in 1994. The current price per square foot is $1,270. The average price per square foot for Single Family listings in WINDERMERE is $460. The average listing price for Single Family in WINDERMERE is $2,237,531. To schedule a showing of MLS#o6401757 at 5138 FAIRWAY OAKS DR in WINDERMERE, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.

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5138 FAIRWAY OAKS DR
WINDERMERE, FL