For SaleSingle Family ResidenceActive
5138 Fairway Oaks Dr
Windermere, FL 34786
$4,999,500
204 Days On Site
- 4Beds
- 5Baths5 full
- 4,330Sq Ft
- $1,155Per Sq Ft
- 0.5Acres
- 1994Built
- Subdivision
- Isleworth
- County
- Orange
- MLS®
- O6401757
Overview
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.
Listing Snapshot
- Price
- $4,999,500
- Days On Site
- 204 Days
- Bedrooms
- 4
- Inside Area (SqFt)
- 4,330 sqft
- Total Baths
- 5
- Full Baths
- 5
- Partial Baths
- 0
- Lot Size
- 0.5 Acres
- Year Built
- 1994
- MLS® Number
- O6401757
- Status
- Active
- Property Tax
- $19,599.37 (2025)
- HOA/Condo/Coop Fees
- $1,224 monthly
- Sq Ft Source
- Public Records
Property Details
General Features
17 items
- Acres
- 0.5
- Attached Garage
- Yes
- Direction Faces
- Northeast
- Foundation
- Slab
- Garage
- Yes
- Garage Spaces
- 3
- Levels
- One
- Parking
- Circular Driveway, Garage Door Opener, Garage Faces Side, Attached
- Pets
- Breed Restrictions
- Property Sub Type
- Single Family Residence
- Security
- Gated Community, Security Gate
- Sewer
- Septic Tank
- SqFt Total
- 5,911
- Style
- Traditional
- Utilities
- Cable Available, Natural Gas Available, Cable Connected, Electricity Connected, Natural Gas Connected, Water Connected
- Water Source
- Public
- Zoning
- P-D
Interior Features
23 items
- Appliances
- Bar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
- Cooling
- Central Air, Zoned
- Fireplace
- Yes
- Fireplace Features
- Family Room
- Flooring
- Tile
- Furnished
- Furnished
- Heating
- Electric, Natural Gas
- Interior
- Built-in Features, Crown Molding, Eat-in Kitchen, Stone Counters, Walk-In Closet(s)
- Laundry Features
- Inside, Laundry Room
- Spa
- Yes
Rooms
| Room | Dimensions | Level | Features |
|---|---|---|---|
| Bathroom 2 | First | Description - Room4 | |
| Bathroom 3 | First | Description - Room6 | |
| Bathroom 4 | First | Description - Room8 | |
| Bedroom 2 | First | Description - Room3 | |
| Bedroom 3 | First | Description - Room5 | |
| Bedroom 4 | First | Description - Room7 | |
| Dining Room | First | Description - Room12 | |
| Family Room | First | Description - Room10 | |
| Kitchen | First | Description - Room9 | |
| Living Room | First | Description - Room11 | |
| Master Bathroom | First | Description - Room2 | |
| Master Bedroom | First | Description - Room1 | |
| Office | First | Description - Room13 |
Exterior Features
13 items
- Construction Details
- Block, Stucco
- Exterior
- Lighting, Rain Gutters
- Fencing
- Other
- Lot Features
- Landscaped, On Golf Course
- Patio And Porch
- Covered, Rear Porch
- Pool Features
- Heated, In Ground, Private
- Private Pool
- Yes
- Roof
- Tile
- Spa
- Yes
- Spa Features
- Heated, In Ground
- View
- Lake, Pond, Water, Golf Course
- Waterfront Features
- LAKE BRENDA AKA HOURGLASS POND
- Waterview
- Lake, Pond, Water, Golf Course
Community Features
8 items
- Association Amenities
- Cable TV, Gated, Playground, Security
- Association Fee
- $3672.0
- Association Fee Frequency
- Quarterly
- Community Features
- Gated, Playground, Street Lights
- MLS Area
- 34786 - Windermere
- Township
- 23
- Financing Terms Available
- Cash, Conventional
- Roads
- Paved
Location
5138 Fairway Oaks Dr, Windermere, FL 34786 · 34786 - Windermere
Neighborhood & Commute
ZIP Code 34786
- Median household income
- $127,371
- Income per person
- $64,053
- Households
- 17,419
- Average household size
- 2.82
- Median age
- 38.9
Source: Walk Score.
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
Schools
- Elementary School
- Windermere Elem
- Middle School
- Chain of Lakes Middle
- High School
- Olympia High
Price & Status History
- Listing updated with changes from the MLS®
- Status changed to Active
- Price changed to $4,999,500
- Listing first seen on site
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