Home in 5138 Fairway Oaks Dr Windermere for sale with MLS# O6401757
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.
5138 Fairway Oaks Dr, Windermere, FL 34786
- Price:
- $5,500,000.00
- Original List Price:
- $5,500,000.00
- List Price per Sq Ft (Calculated, Approx.):
- $1,270.21
- Listing Type:
- For Sale
- Status:
- Active
- Listing Category:
- Residential
- Property Type:
- Single Family House
- MLS Number:
- O6401757
- Bedrooms:
- 4
- Bathrooms Total:
- 5
- Full Bath:
- 5
- Living Area:
- 4,330 Sqft
- Built-Up Area:
- 5,911 Sqft
- Lot Area:
- 21,939 Sqft
- Building Area Source:
- Public Records
- Living Area Source:
- Public Records
- Lot Features:
- On Golf Course, Oversized Lot, Landscaped
- Lot Size Acres:
- 0.5
- View from the Property:
- Water, Golf Course
- Waterfront:
- No
- Private Pool
- Swimming Pool Features:
- Heated, In Ground, Deck
- Spa
- Spa Features:
- Heated, In Ground
- Security:
- Security Gate, Gated Community
- Furnished:
- Furnished
- Appliances:
- Dryer, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Freezer, Electric Water Heater, Ice Maker, Exhaust Fan, Range, Range Hood, Wine Refrigerator, Bar Fridge
- Interior:
- Eat-in Kitchen, Walk-In Closet(s), Built-in Features, Ceiling Fans(s), Kitchen/family Room Combo, Living Room/dining Room Combo, Stone Counters, Thermostat, Solid Surface Counters, Crown Molding
- Exterior:
- Lighting, Rain Gutters, French Doors
- Patio and Porch:
- Covered, Rear Porch
- Laundry:
- Inside, Laundry Room, Corridor Access
- Fireplace
- Fireplace:
- Family Room
- Air Conditioning System:
- Zoned, Central Air
- Heating System:
- Electric, Natural Gas, Natural Gas
- Fence:
- Other
- Property Entrance Faces:
- Northeast
- Water View
- Water View Details:
- Pond, Lake
- Year Built:
- 1994
- Roof:
- Tile
- Architectural Style:
- Traditional
- Levels:
- One
- Construction Materials:
- Block, Stucco
- Flooring:
- Tile
- Foundation Details:
- Slab
- Flood Zone Code:
- X
- Tax Annual Amount:
- $19,599.37
- Tax Year:
- 2025
- Association Fee:
- $3,672.00
- Association Fee Frequency:
- Quarterly
- Total Annual Fees:
- $14,688.00
- Total Monthly Fees:
- $1,224.00
- Garage
- Garage Spaces:
- 3
- Attached Garage
- Parking Features:
- Garage Door Opener, Circular Driveway, Garage Faces Side
- Sewer:
- Septic Tank
- Utilities Available:
- Electricity Connected, Natural Gas Connected, Water Connected, Cable Connected, Fiber Optics
- Water Source:
- Public
- Association
- Minimum Lease Term:
- 8-12 Months
- Pets Allowed?:
- Breed Restrictions
- Amenities Provided by the Homeowner's Association (HOA):
- Playground, Security, Gated, Cable Tv
- Subdivision Name:
- ISLEWORTH
- Community Features:
- Street Lights, Playground, Golf Carts Ok, Buyer Approval Required, Community Mailbox, Gated Community - Guard
- Association Fee Includes:
- Maintenance Grounds, Cable Tv, Security, Internet, Escrow Reserves Fund, Guard - 24 Hour, Private Road
- Senior Community:
- No
- Association Fee Required:
- Required
- Association Management:
- Dan O’Connell
- Association Phone:
- 407-909-2071
- Listing Terms Considered by Seller:
- Cash, Conventional
- Occupant Type:
- Vacant
- Lease Considered:
- Yes
- Tax Legal Description:
- ISLEWORTH 16/118 LOT 108
- Real Estate Folio Number (Parcel Number):
- 16-23-28-3899-01-080
- Zoning:
- P-D
- Title to the property is held by owner as:
- Fee Simple
- Elementary School:
- Hollywood Park
- High School:
- Olympia High
- Middle Or Junior School:
- Chain Of Lakes Middle
- Originally published on:
- April 25, 2026 12:23 pm
- Active on the market since:
- April 25, 2026
- Listing Agreement executed on:
- April 23, 2026
- Listing Status Last Changed On:
- April 25, 2026 12:23 pm
- Photos updated on:
- May 5, 2026 6:46 pm
- Last Modified:
- May 5, 2026 6:46 pm
- Association Approval Required
- Courtesy of:
- ISLEWORTH REALTY LLC
- Attribution:
- 407-909-9000
- Road Surface Type:
- Paved
- Street Name:
- FAIRWAY OAKS DR
- Street Number:
- 5138
- City:
- WINDERMERE
- State:
- Florida
- Zip Code:
- 34786
- County:
- Orange
- Latitude:
- N28° 29' 3.4''
- Longitude:
- W82° 28' 10.4''
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Neighborhood Stats
Source: U.S. Census Bureau, ACS 5-Year Estimates
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