5138 Fairway Oaks Dr, Windermere, FL, 34786

Address

5138 Fairway Oaks Dr, WINDERMERE, FL

Listing Type

Active

Price

$ 4,999,500

Your Agent

Xena Vallone

Lic R.E. Broker, Broker / Owner

Cell: 941-224-5950

Property Attributes

MLS#O6401757
TypeSingle Family
Listing Status Active
CountyOrange
CityWINDERMERE
AreaWindermere
NeighborhoodISLEWORTH
Zip34786
StyleTraditional
Year Built1994
Taxes$ 19599
Price$ 4,999,500
Bedrooms4
Full Bathrooms5
Half Bathrooms0
Sqr Footage4330
Lot Size0.5 Acres

Data Source:

Stellar MLS

Property 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.

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

Price History
4/25/2026	Listed $5,500,000
8/14/2026	9$4,999,500

General Features

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
In Law Suite YN	false
Flood Zone Code X	Yes
DockY/N	false

Interior Features

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
Laundry Features	Corridor Access,Inside,Laundry Room
Total Bedrooms	4
LivingAreaSource	Public Records
Total Baths	5

Exterior Features

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