Date
Details
Price
Change
Source
4/25/2026
Listed
$5,500,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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$5,500,000 Just Listed
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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.
Full Property Details
Full Property Details for 5138 Fairway Oaks Dr
General
- Price: $5,500,000
- HOA FEE: $1,224/month
- HOA FEE FREQ.: Quarterly
- Taxes: $19,599 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6401757
- Updated: 4/25/2026
- Added to Site: 1 day(s) ago
Rental Information
- Min. Lease: 8-12 Months
Interior
- Number of Rooms: 13
- Interior Features: Built-in Features, Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, Kitchen and Family Room Combination, Living Room/Dining Room Combo, Solid Surface Counters, Stone Counters, Thermostat, Walk-In Closet(s)
- Fireplace: Yes
- Fireplace(s): Family Room
- Appliances: Bar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
- Furnishings: Furnished
- Flooring: Porcelain Tile
Rooms
Bathrooms
- Total Bathrooms: 5
- Full Bathrooms: 5
Bedrooms
- Total Bedrooms: 4
Other Rooms
- Laundry: Corridor Access, Inside, Laundry Room
Additional Information
- Shared Amenities: Cable TV, Gated, Playground, Security
- Pool: Yes
- Private Pool: Yes
- Pool Description: Deck, Heated, In Ground
- Spa: Yes
- Spa Description: Heated, In Ground
- Security/Safety: Gated Community, Security Gate
Exterior
- Exterior Features: French Doors, Lighting, Rain Gutters
- Deck/Patio: Covered, Rear Porch
- Porch/Patio/Deck: Covered, Rear Porch
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 3
- Covered Spaces: 3
- Parking Features: Circular Driveway, Garage Door Opener, Garage Faces Side
Location
- Area: 34786 - Windermere
- County: Orange
- Development Name: 34786 - Windermere
- Subdivision: ISLEWORTH
- Driving Directions: From Apopka Vineland Road to West on Conroy Windermere to Left into Isleworth (Isleworth Country Club Drive) to Right on Fairway Oaks.
- Direction Faces: Northeast
School Information
- Elementary School: Windermere Elem
- Middle School: Chain of Lakes Middle
- High School: Olympia High
Community
- Community Name: 34786 - Windermere
- Community Features: Community Boat Ramp, Water Access, Buyer Approval Required, Community Mailbox, Gated Community - Guard, Golf Carts OK, Playground
- Optional Amenities: Cable TV, Gated, Playground, Security
- Association: Yes
- Assoc. Name: Dan O’Connell
- Assoc. Fees Include: 24-Hour Guard, Cable TV, Escrow Reserves Fund, Internet, Maintenance Grounds, Private Road, Security
- Pet Restrictions: Per Orange County breed restrictions, number limits and leash laws.
Heating & Cooling
- Cooling Type: Central Air, Zoned
- Heating Type: Electric, Natural Gas
Utilities
- Sewer: Septic Tank
- Water District: LAKE BRENDA AKA HOURGLASS POND
- Water: Public
- Utility Description: Cable Connected, Electricity Connected, Fiber Optics, Natural Gas Connected, Street Lights, Water Connected
Structural Information
- Architectural Info: Traditional
- Architectural Style: Traditional
- Exterior Const.: Block, Stucco
- Roof: Tile
- Stories/Levels: One
- Square Feet: 4,330
- Sq. Ft. Source: Public Records
- Year Built: 1994
Lot Features
- Property View: Golf Course, Water
- Lot Size (Acres): 0.5
- Lot Size (Sq. Ft.): 21,939
- Lot Size: 21939
- Street/Road Desc.: Paved
- Fencing (Description): Other
Water Features
- Water View: Yes
- Water Front Name: LAKE BRENDA AKA HOURGLASS POND
Financial Considerations
- Association Fee: $3,672
- Assoc Fee Freq.: Quarterly
- Assoc Fee Desc.: Required
- Tax Amount: $19,599.37
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: ISLEWORTH 16/118 LOT 108
- Flood Zone Info: X
- APN: 162328389901080
- Property ID: 162328389901080
- Block/Lot/Section: 1
Listed by Isleworth Realty Llc
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Listing agents
— 5138 Fairway Oaks Dr —
Isleworth Realty Llc
Isleworth Realty Llc
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 5138 Fairway Oaks Dr
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Windermere Elementary School 11125 Park Avenue, Windermere, FL 34786 | K-5 | 1.8 mi |
Chain Of Lakes Middle School 8700 Conroy Windermere Road, Orlando, FL 32835 | 6-8 | 1.7 mi |
Olympia High School 4301 South Apopka Vineland Road, Orlando, FL 32835 | 9-12 | 1.8 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 5138 Fairway Oaks Dr
Estimate the Cost
Estimate the Cost for 5138 Fairway Oaks Dr
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Sold by Stellar Non-Member Office
5138 Fairway Oaks Dr, Windermere, FL 34786 (MLS# O6401757) is a Single Family property with 4 bedrooms and 5 full bathrooms. 5138 Fairway Oaks Dr is currently listed for $5,500,000 and was received on April 25, 2026. Want to learn more about 5138 Fairway Oaks Dr? Do you have questions about finding other Single Family real estate for sale in Windermere? You can browse all Windermere real estate or contact a Coldwell Banker agent to request more information.