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5138 Fairway Oaks Dr, Windermere, FL

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$4,999,500

($1,155/sqft)

List Status: Active
5138 Fairway Oaks Dr
Windermere, FL 34786


4 beds
5 baths
4330 living sqft
Top Features
  • View: Water, Golf Course
  • Subdivision: Isleworth
  • Built in  1994
  • Single Family Residence
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 unparallele
Property Details
Property Features
Property Sub Type
Single Family Residence
View
Water, Golf Course
Parking
Garage Faces Side, Circular Driveway, Garage Door Opener
Pool
Heated, Deck, In Ground
County
Orange
Subdivision
ISLEWORTH
Interior Features
MlsStatus
Active
Additional Information
Additional Lease Restrictions
Per Isleworth Community Association (ICA)
Additional Water Information
The Isleworth community is set along six of the lakes within the much desirable Butler Chain of Lakes. We offer a private, community boat ramp for our residents eager to enjoy these great waters.
Amenities Additional Fees
Club amenities are available to Club members only. Residents of the community are not required to join the Isleworth Golf & Country Club.
Appliances
Freezer, Electric Water Heater, Exhaust Fan, Dishwasher, Bar Fridge, Microwave, Range Hood, Refrigerator, Disposal, Dryer, Range, Washer, Wine Refrigerator, Ice Maker
Approval Process
Per Isleworth Community Association (ICA)
Architectural Style
Traditional
Association Amenities
Cable TV, Security, Gated, Playground
Association Fee
3672
Association Fee Frequency
Quarterly
Association Fee Includes
Maintenance Grounds, Cable TV, Private Road, Guard - 24 Hour, Internet, Security, Escrow Reserves Fund
Association Fee Requirement
Required
Bathrooms Total Integer
5
Building Area Source
Public Records
Building Area Total
5911
Building Area Total Srch SqM
549.15
Building Area Units
Square Feet
Calculated List Price By Calculated SqFt
1154.62
Community Features
Buyer Approval Required, Golf Carts OK, Community Mailbox, Gated Community - Guard, Street Lights, Playground
Construction Materials
Stucco, Block
Cooling
Zoned, Central Air
Country
US
Cumulative Days On Market
137
Current Price
4999500.00
Direction Faces
Northeast
Elementary School
Windermere Elem
Exterior Features
Lighting, Rain Gutters
Fencing
Other
Fireplace Features
Family Room
Flood Zone Code
X
Flooring
Tile
Foundation Details
Slab
Furnished
Furnished
Garage Spaces
3
Heating
Electric, Natural Gas
High School
Olympia High
Interior Features
Solid Surface Counters, Thermostat, Eat-in Kitchen, Crown Molding, Built-in Features, Stone Counters, Kitchen/Family Room Combo, Ceiling Fans(s), Living Room/Dining Room Combo, Walk-In Closet(s)
Laundry Features
Laundry Room, Corridor Access, Inside
Levels
One
List AOR
Orlando Regional
Living Area Meters
402.27
Living Area Source
Public Records
Living Area Units
Square Feet
Lot Features
Landscaped, On Golf Course, Oversized Lot
Lot Size Acres
0.5
Lot Size Square Feet
21939
Lot Size Square Meters
2038
Middle Or Junior School
Chain of Lakes Middle
Minimum Lease
8-12 Months
Modification Timestamp
2026-09-16T16:50:11.015Z
Monthly HOA Amount
1224.00
Occupant Type
Vacant
Ownership
Fee Simple
Parcel Number
16-23-28-3899-01-080
Patio And Porch Features
Rear Porch, Covered
Pet Restrictions
Per Orange County breed restrictions, number limits and leash laws.
Pets Allowed
Breed Restrictions
Previous List Price
5500000
Price Change Timestamp
2026-08-14T18:31:24.000Z
Public Survey Range
28
Public Survey Section
16
RATIO Current Price By Calculated SqFt
1154.62
Road Surface Type
Paved
Roof
Tile
Room Count
13
Security Features
Security Gate, Gated Community
Sewer
Septic Tank
Spa Features
Heated, In Ground
Tax Annual Amount
19599.37
Tax Block
01
Tax Book Number
16/118
Tax Lot
108
Tax Year
2025
Total Acreage
1/2 to less than 1
Total Annual Fees
14688.00
Total Monthly Fees
1224.00
Township
23
Universal Property Id
US-12095-N-162328389901080-R-N
Unparsed Address
5138 FAIRWAY OAKS DR
Utilities
Fiber Optics, Water Connected, Cable Connected, Natural Gas Connected, Electricity Connected
Water Body Name
LAKE BRENDA AKA HOURGLASS POND
Water Source
Public
Water View
Pond, Lake
Zoning
P-D
Neighborhood Map
Popup

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MLS #MFRO6401757 Listing courtesy of Isleworth Realty Llc provided by Stellar MLS.

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All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independent verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. The source of the listing data is as follows: Stellar MLS (updated 11/9/26 11:02 AM) |

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