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Single family home for sale at 5138 Fairway Oaks Dr, Windermere, FL 34786 | MLS# O6401757 | Listing updated on 2026-09-16
Photo 1 of Single family home for sale at 5138 Fairway Oaks Dr, Windermere, FL 34786 | MLS# O6401757 | Listing updated on 2026-09-16
Photo 2 of Single family home for sale at 5138 Fairway Oaks Dr, Windermere, FL 34786 | MLS# O6401757 | Listing updated on 2026-09-16
Photo 3 of Single family home for sale at 5138 Fairway Oaks Dr, Windermere, FL 34786 | MLS# O6401757 | Listing updated on 2026-09-16
Photo 4 of Single family home for sale at 5138 Fairway Oaks Dr, Windermere, FL 34786 | MLS# O6401757 | Listing updated on 2026-09-16
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$4,999,500

Monthly Est:$24,884

  • Beds Icon4 Beds
  • Beds Icon
    5 Baths
  • Beds Icon4,330sqft

5138 Fairway Oaks Dr, Windermere, FL 34786

$24,884/moEst:

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  • Single Family Residence

  • Built in 1994

  • $1,224/mo HOA

  • 21,939 sqft lot

  • $1,155/sq.ft

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.

  • Houzeo last checked: 2 hours ago
  • Listing updated: September 16, 2026 at 4:50 pm
  • Listing Provided by: Monica Lochmandy (407) 230-6888 , Sarah Longwell | ISLEWORTH REALTY LLC (407) 909-9000
  • Source: Stellar MLS-FL | MLS#: O6401757 Stellar MLS-FL

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Orange County

  • City

    Windermere

  • Neighborhood

    --

  • Year Built

    1994

  • HOA Fees

    $1224/mo

  • Finished Area

    4,330 sqft

  • Lot Size

    21,939 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    Stellar MLS

  • MLS Number

    O6401757

  • MLS Status

    Active

  • Days on Market

    186

  • Cumulative Days on Market

    137

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Location

HOA Management

Dan O’Connell

HOA Fees

$3,672/ Quarterly

Amenities

Amenities and services may be covered by one or multiple associations and service providers.

Internet Internet

Security Gate Security Gate

Cable TV Cable TV

Security Guard Security Guard

Park Playground Park Playground

Maintenance Maintenance

Escrow Reserves Fund Escrow Reserves Fund

Private Road Private Road

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 4

    Bathrooms: 5

  • Primary Bedroom

    Level: First

  • Primary Bathroom

    Level: First

  • Bedroom 2

    Level: First

  • Bathroom 2

    Level: First

  • Bedroom 3

    Level: First

  • Bathroom 3

    Level: First

  • Bedroom 4

    Level: First

  • Bathroom 4

    Level: First

  • Kitchen

    Level: First

  • Family Room

    Level: First

  • Living Room

    Level: First

  • Dining Room

    Level: First

  • Office

    Level: First

Interior

  • Exterior Features

    Lighting, Rain Gutters

  • Sewer

    Septic Tank

  • Heating

    Electric, Natural Gas

  • Cooling

    Central Air, Zoned

  • 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)

  • Appliances

    Bar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator

  • Flooring

    Tile

Construction

  • Year Built

    Year Built: 1994

  • Home type

    Single Family Residence

  • Foundation Details

    Slab

  • Architectural Style

    Traditional

  • Construction Materials

    Block, Stucco

  • Roof

    Tile

Utilities & Energy

  • Parking Features

    Circular Driveway, Garage Door Opener, Garage Faces Side

  • Security Features

    Gated Community, Security Gate

  • Pool Features

    Deck, Heated, In Ground

  • Association Amenities

    Cable Tv, Gated, Playground, Security

  • Fireplace Features

    Family Room

  • Laundry Features

    Corridor Access, Inside, Laundry Room

  • Utilities

    Cable Connected, Electricity Connected, Fiber Optics, Natural Gas Connected, Water Connected

  • Water Source

    Public

Other Features

  • Lot Features

    Landscaped, On Golf Course, Oversized Lot

  • Community Features

    Buyer Approval Required, Community Mailbox, Gated Community Guard, Golf Carts Ok, Playground, Street Lights

  • Patio And Porch Features

    Covered, Rear Porch

  • Subdivision Name

    Isleworth

Price History

DateEventPrice

08/14/2026

Source: mls_logoStellar MLS-FL #MFRO6401757

Listing Removed

$4,999,500 -9.10%

$1,155/sqft

04/25/2026

Source: mls_logoStellar MLS-FL #MFRO6401757

Listed for Sale

$5,500,000 +89.66%

$1,270/sqft

09/24/2025

Source: mls_logoStellar MLS-FL #MFRO6282470

Sold

$2,900,000 +16.00%

$670/sqft

09/24/2025

Source: mls_logoStellar MLS-FL #MFRO6282470

Price Decreased

$2,500,000 -13.79%

$577/sqft

08/17/2025

Source: mls_logoStellar MLS-FL #MFRO6282470

Pending

$2,900,000

$670/sqft

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Nearby Homes

Based on information from Stellar MLS® through Oct 28, 2026, 02:15PM as submitted to and distributed by MLS GRID. All data is obtained from various sources and may not have been verified by the broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers’ personal non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end-user license agreement prescribed by the Member Participant’s applicable MLS, if any, and as amended from time to time. © 2026 Stellar MLS. All Rights Reserved.

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