5138 Fairway Oaks Dr, Windermere, FL 34786
$4,999,500 - For Sale
Property Details
Price: $4,999,500
Sq Ft: 4,330
($1,155 per sqft)
Bedrooms: 4
Bathrooms: 5
City:Windermere
County:Orange
Type:Single Family
Development:Isleworth
Subdivision:Isleworth
Acres:0.5000
Virtual Tour/Floorplan:View
Year Built:1994
Listing Number:O6401757
Status Code:A-Active
Taxes:$19,599.37
Tax Year: 2025
Garage: 3
/ Y
Furnishings: Furnished
Pets Allowed: Breed Restrictions
Total Recurring Fees: $1,224
Total Recurring Fee Frequency: 0.00
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Equipment:
Bar Fridge
Dishwasher
Disposal
Dryer
Electric Water Heater
Exhaust Fan
Freezer
Ice Maker
Microwave
Range
Range Hood
Refrigerator
Washer
Wine Refrigerator
Interior Features:
Built-in Features
Ceiling Fans(s)
Crown Molding
Eat-in Kitchen
Kitchen/Family Room Combo
Living Room/Dining Room Combo
Solid Surface Counters
Stone Counters
Thermostat
Walk-In Closet(s)
Exterior Features:
Lighting
Rain Gutters
View:
Golf Course
Water
Amenities:
Cable TV
Gated
Playground
Security
Financial Information:
Taxes: $19,599.37
Tax Year: 2025
Association Fee: $3,672.00
Association Fee Frequency: Quarterly
Room Dimensions:
Laundry: Corridor Access, Inside, Laundry Room
School Information:
Elementary School: Windermere Elem
Middle School: Chain Of Lakes Middle
Junior High: Chain Of Lakes Middle
High School: Olympia High
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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.
Building Description: Traditional
MLS Area: 34786 - Windermere
Total Square Footage: 5,911
Price per Square Feet: $1,154.62
Water: Public
Construction: Block, Stucco
Date Listed: 2026-04-25 00:00:00
Pool: Y
Pool Description: Deck, Heated, In Ground
Private Spa: Y
Furnished: Furnished
Parking: Circular Driveway, Garage Door Opener, Garage Faces Side
Garage Description: Y
Garage Spaces: 3
Attached Garage: Y
Flooring: Tile
Roof: Tile
Heating: Electric, Natural Gas
Cooling: Central Air, Zoned
Fireplace: Y
Security: Gated Community, Security Gate
Laundry: Corridor Access, Inside, Laundry Room
Pets: Breed Restrictions
Sewer: Septic Tank
Lot Desc.: Landscaped, On Golf Course, Oversized Lot
Parcel ID: 16-23-28-3899-0
Amenities: Cable Tv, Gated, Playground, Security
Listing Courtesy Of: Isleworth Realty Llc
mlochmandy@isleworth.com
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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Additional Information:
Building Description: Traditional
MLS Area: 34786 - Windermere
Total Square Footage: 5,911
Price per Square Feet: $1,154.62
Water: Public
Construction: Block, Stucco
Date Listed: 2026-04-25 00:00:00
Pool: Y
Pool Description: Deck, Heated, In Ground
Private Spa: Y
Furnished: Furnished
Parking: Circular Driveway, Garage Door Opener, Garage Faces Side
Garage Description: Y
Garage Spaces: 3
Attached Garage: Y
Flooring: Tile
Roof: Tile
Heating: Electric, Natural Gas
Cooling: Central Air, Zoned
Fireplace: Y
Security: Gated Community, Security Gate
Laundry: Corridor Access, Inside, Laundry Room
Pets: Breed Restrictions
Sewer: Septic Tank
Lot Desc.: Landscaped, On Golf Course, Oversized Lot
Parcel ID: 16-23-28-3899-0
Amenities: Cable Tv, Gated, Playground, Security
Map of 5138 Fairway Oaks Dr, Windermere, FL 34786
Listing Courtesy Of: Isleworth Realty Llc
mlochmandy@isleworth.com
PRECISE REALTY CORP
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Location
2100 Constitution Boulevard
Sarasota, FL 34231
Contact
Jennifer Leblanc, Broker
941-400-0374
IDX information is provided exclusively for consumers’ personal, noncommercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. The data relating to real estate for sale on this Website comes in part from the Broker Reciprocity Program (BR Program) of My Florida Regional MLS DBA Stellar MLS. The source of this real property information is the copyrighted and proprietary database compilation of the My Florida Regional MLS DBA Stellar MLS and © 2026. Information last refreshed: 2026-10-08 04:20:40
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