5138 Fairway Oaks Dr, Windermere, FL 34786

Windermere
Local realty services provided by:Better Homes and Gardens Real Estate Synergy
5138 Fairway Oaks Dr,Windermere, FL 34786
$4,999,500
  • 4 Beds
  • 5 Baths
  • 4,330 sq. ft.
  • Single family
  • Active
Listed by: monica lochmandy, sarah longwell
Office: isleworth realty llc.
MLS#:O6401757
Source:MFRMLS

Price summary

  • Price:$4,999,500
  • Price per sq. ft.:$845.8
  • Monthly HOA dues:$1,224

About this home

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...

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Home facts

  • Year built:1994
  • Subdivision & Development:ISLEWORTH
  • Listing ID #:O6401757
  • Added:194 day(s) ago
  • Updated:November 05, 2026 at 10:53 PM

Rooms and interior

  • Bedrooms:4
  • Total bathrooms:5
  • Full bathrooms:5
  • Flooring:Tile
  • Dining Description:Eat In Kitchen, Living Room/Dining Room Combo
  • Kitchen Description:Bar Fridge, Dishwasher, Disposal, Eat-in Kitchen, Exhaust Fan, Freezer, Ice Maker, Kitchen/Family Room Combo, Microwave, Range, Range Hood, Refrigerator, Solid Surface Counters, Stone Counters, Wine Refrigerator
  • Bedroom Description:Walk-In Closet(s)
  • Living area:4,330 sq. ft.

Heating and cooling

  • Cooling:Central Air, Zoned
  • Heating:Electric, Natural Gas
  • Central air:Yes

Structure and exterior

  • Roof:Tile
  • Year built:1994
  • Building area:4,330 sq. ft.
  • Lot area:0.5 Acres
  • Lot Features:Landscaped, On Golf Course, Oversized
  • Architectural Style:Traditional
  • Construction Materials:Block, Stucco
  • Exterior Features:Covered Porch/Patio, Lighting, Rain Gutters, Rear Porch
  • Foundation Description:Slab
  • Levels:1 Story

Schools

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

Utilities

  • Water:Public, Water Connected
  • Sewer:Septic Tank

Finances and disclosures

  • Price:$4,999,500
  • Price per sq. ft.:$845.8
  • Tax amount:$19,599 (2025)

Features and amenities

  • Appliances:Bar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
  • Laundry features:Dryer, Inside, Laundry Room, Washer
  • Amenities:Built-In Features, Cable Connected, Cable TV, Ceiling Fans(s), Crown Molding, Eat-in Kitchen, Fiber Optics, Gated, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Natural Gas Connected, Playground, Security, Solid Surface Counters, Stone Counters, Thermostat, Walk-In Closet(s)
  • Pool features:Heated, In Ground, Pool/Deck, Private Pool

Parking

  • Parking description:Attached Garage, Circular Driveway, Garage Door Opener, Garage Faces Side
  • Garage:Yes
  • Garage spaces:3
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