5138 FAIRWAY OAKS DR, WINDERMERE, FL 34786

  • Open House
  • New Listing
  • Virtual Tour
  • Price Reduced$500,500
  • Active

$4,999,500

  • 4 BedroomBedrooms
  • 5 BathroomBathrooms
  • 4,330 Sq.Ft.
  • Single Family
  • Active
  • MLS# O6401757
  • Floor Plan
  • Sold on 
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Property Description

Set along Isleworths signature 12th fairway, this fully reimagined estate captures the essence of refined golf course living within the renowned Isleworth Golf & Country Clubrecognized 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 appliancesincluding a striking black range with matching hood, refrigerator, and microwaveall 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 Floridas premier shopping, dining, and entertainment destinations.

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Property Details 5138 FAIRWAY OAKS DR, WINDERMERE, FL 34786

Facts & Features

  • MLS #: O6401757
  • Status: Active
  • Date Listed: 04/25/2026
  • Type: Single Family
  • Sub Type: Single Family Residence
  • Year Built: 1994
  • Style: Traditional
  • Price: $4,999,500
  • Acres: 0.50
  • Area: 34786 - Windermere
  • County: Orange
  • Subdivision: ISLEWORTH
  • Bedrooms: 4
  • Bathrooms: 5
  • Full Baths: 5
  • Total SqFt: 4,330

Amenities

  • Amenities: Cable TV, Gated, Playground, Security
  • Parking: Circular Driveway, Garage Door Opener, Garage Faces Side
  • # of Garages: 3
  • Features: Buyer Approval Required, Community Mailbox, Gated Community - Guard, Golf Carts OK, Playground, Street Lights
  • Waterfront: Yes
  • Waterfront Type: Public
  • Pool: Yes
  • Pool Type: Deck, Heated, In Ground

Interior

  • 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)
  • Flooring: Tile
  • Appliances: Bar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
  • Utilities: Cable Connected, Electricity Connected, Fiber Optics, Natural Gas Connected, Water Connected
  • Heating: Electric, Natural Gas
  • Cooling: Central Air, Zoned

Exterior

  • Exterior Features: Lighting, Rain Gutters
  • Lot Description: Landscaped, On Golf Course, Oversized Lot
  • Roof: Tile
  • Construction: Block, Stucco

Schools

  • Elementary: Windermere Elem
  • Middle: Chain of Lakes Middle
  • High: Olympia High

Additional Information

  • Zoning: P-D

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