5138 FAIRWAY OAKS DR Windermere, FL $ 5,500,000
5138 FAIRWAY OAKS DR
$ 5,500,000
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5138 FAIRWAY OAKS DR

Windermere, FL, 34786
$ 5,500,000
Bedrooms4 Baths5.0 Sq 4,330

Monthly Estimate*

$ 33,864

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Single Family Home for sale in Windermere, FL

for $5,500,000 with 4 bedrooms and 5 full baths. This 4,330 square foot home was built in 1994 on a lot size of 0.5.

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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Single Family Active

Price

$ 5,500,000

Bedrooms

4

Full Bath

5

Property Type

Single Family

Taxes

$ 19,599

Style

Traditional

Lot Size

0.5

Year Built

1994

Town/City

Windermere

County/Region

Orange

MLS | Web ID

O6401757

Features
General
Sewer Septic Tank
Heating Electric Natural Gas
Cooling Central Air Zoned
Utilities Cable Connected Electricity Connected Fiber Optics Natural Gas Connected Street Lights Water Connected
Roof Tile
Appliances Bar Fridge Dishwasher Disposal Dryer Electric Water Heater Exhaust Fan Freezer Ice Maker Microwave Range Range Hood Refrigerator Washer Wine Refrigerator
Zoning P-D
HOA Fee 3672
Garage Spaces 3
Association Fee Includes 24-Hour Guard Cable TV Escrow Reserves Fund Internet Maintenance Grounds Private Road Security
Patio/Porch Features Covered Rear Porch
Architectural Style Traditional
Pool Features Deck Heated In Ground
Security Features Gated Community Security Gate
Construction Materials Block Stucco
Pets Allowed Breed Restrictions
Year Built 1994
View Golf Course Water
Levels One
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
Community Features Community Boat Ramp Water Access Buyer Approval Required Community Mailbox Gated Community - Guard Golf Carts OK Playground
Assoc Fee Paid Per Quarterly
County Orange
New Construction false
Property Type Residential
Association Amenities Cable TV Gated Playground Security
Attached Garage true
Subdivision Name ISLEWORTH
Facing Direction Northeast
Garage Y/N true
Total Rooms 13
Full Baths 5
Status Active
Directions From Apopka Vineland Road to West on Conroy Windermere to Left into Isleworth (Isleworth Country Club Drive) to Right on Fairway Oaks.
High School Olympia High
City WINDERMERE
Body of Water LAKE BRENDA AKA HOURGLASS POND
Association Name Dan O’Connell
Senior Community Y/N false
MLS Area 34786 - Windermere
Lot Size Units Square Feet
Lot Size Square Feet 21939
Carport Y/N false
Listing Terms Cash Conventional
Spa Features Heated In Ground
Elementary School Windermere Elem
Land Lease Y/N false
Tax Annual Amount 19599.37
Middle/Junior High School Chain of Lakes Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://player.vimeo.com/video/1183953909?h=f00523e43b&badge=0&autopause=0&player_id=0&app_id=58479
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Vacant
Tax Lot 108
Legal Description ISLEWORTH 16/118 LOT 108
Water View Lake Pond
Minimum Lease 8-12 Months
Water Access Y/N false
Monthly HOA Amount 1224
Water View Y/N true
Flood Zone Code X
DockY/N false
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Interior
Interior Amenities 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)
Flooring Porcelain Tile
Furnished Y/N Furnished
Fireplace Features Family Room
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Half Baths 0
Laundry Features Corridor Access Inside Laundry Room
Total Bedrooms 4
Total Baths 5
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Exterior
Exterior Amenities French Doors Lighting Rain Gutters
Fencing Other
Parking Features Circular Driveway Garage Door Opener Garage Faces Side
Lot Features Landscaped On Golf Course Oversized Lot
Water Source Public
Lot Size Area 21939
Foundation Details Slab
Spa true
Building Area Total 5911
Lot Size Acres 0.5
Road Surface Type Paved
Private Pool true
Waterfront Y/N false
Covered Spaces 3
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* Excluded Features
List By
Isleworth Realty Llc

Broker

mlochmandy@isleworth.com

Email

Affordability Calculator

$35,498
Per Month
95%
5%
0%
Monthly Principal & Interest
$33,864
Monthly Property Taxes
$1,633
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Olympia High High School High School
Pricing History
DatePricePrice ChangeDescription
4/25/2026$5,500,000 Listed Price

Map


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5138 FAIRWAY OAKS DR, Windermere, FL, 34786 is a Single Family Home for sale at $5,500,000 with 4,330 sqft and a lot size of 0.5. 5138 FAIRWAY OAKS DR has 4 bedrooms, 5.0 baths, and was built in 1994. The property's zip code is 34786 which is in Windermere, FL