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For sale
    • $5,500,000

    5138 FAIRWAY OAKS DR, WINDERMERE, FL 34786

    4beds
    4,330sqft
    : 
    $38,554/mo
    Get pre-qualified
    Single Family Residence
    Built in 1994
    0.5 Acres Lot
    $5,056,100 Zestimate®
    $1,270/sqft
    $1,224/mo HOA

    What's special

    Exquisite countertopsThree-car garageHome officeDramatic waterfall-edge islandStriking glass-enclosed wine towerCustom cabinetryElegant gold detailing
    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.
    97 days
    |
    646
    |
    20
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Monica Lochmandy 407-230-6888,

    ISLEWORTH REALTY LLC 407-909-9000,

    Sarah Longwell 407-920-8451,

    ISLEWORTH REALTY LLC

    Source: Stellar MLS,MLS#: O6401757MLS LogoOriginating MLS: Orlando Regional

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 5
      • Full bathrooms: 5
      Primary bedroom
      • Description: Room1
      • Features: Dual Closets
      • Level: First
      Bedroom 2
      • Description: Room3
      • Features: Walk-In Closet(s)
      • Level: First
      Bedroom 3
      • Description: Room5
      • Features: Walk-In Closet(s)
      • Level: First
      Bedroom 4
      • Description: Room7
      • Features: Walk-In Closet(s)
      • Level: First
      Primary bathroom
      • Description: Room2
      • Level: First
      Bathroom 2
      • Description: Room4
      • Level: First
      Bathroom 3
      • Description: Room6
      • Level: First
      Bathroom 4
      • Description: Room8
      • Level: First
      Dining room
      • Description: Room12
      • Level: First
      Family room
      • Description: Room10
      • Level: First
      Kitchen
      • Description: Room9
      • Level: First
      Living room
      • Description: Room11
      • Level: First
      Office
      • Description: Room13
      • Level: First
      Heating
      • Electric, Natural Gas
      Cooling
      • Central Air, Zoned
      Appliances
      • Included: Bar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Washer, Wine Refrigerator
      • Laundry: Corridor Access, Inside, Laundry Room
      Features
      • Built-in Features, Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Solid Surface Counters, Stone Counters, Thermostat, Walk-In Closet(s)
      • Flooring: Porcelain Tile
      • Doors: French Doors
      • Has fireplace: Yes
      • Fireplace features: Family Room
      • Furnished: Yes
      Interior area
      • Total structure area: 5,911
      • Total interior livable area: 4,330 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 3
      • Parking features: Circular Driveway, Garage Door Opener, Garage Faces Side
      • Attached garage spaces: 3
      • Has uncovered spaces: Yes
      Features
      • Levels: One
      • Stories: 1
      • Patio & porch: Covered, Rear Porch
      • Exterior features: Lighting, Rain Gutters
      • Has private pool: Yes
      • Pool features: Deck, Heated, In Ground
      • Has spa: Yes
      • Spa features: Heated, In Ground
      • Fencing: Other
      • Has view: Yes
      • View description: Golf Course, Water, Lake, Pond
      • Has water view: Yes
      • Water view: Water,Lake,Pond
      • Body of water: LAKE BRENDA AKA HOURGLASS POND
      Lot
      • Size: 0.5 Acres
      • Features: Landscaped, On Golf Course, Oversized Lot
      Details
      • Parcel number: 162328389901080
      • Zoning: P-D
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Traditional
      • Property subtype: Single Family Residence
      Materials
      • Block, Stucco
      • Foundation: Slab
      • Roof: Tile
      Condition
      • New construction: No
      • Year built: 1994

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Public
      • Utilities for property: Cable Connected, Electricity Connected, Fiber Optics, Natural Gas Connected, Street Lights, Water Connected

      Community & HOA

      Community
      • Features: Community Boat Ramp, Water Access, Buyer Approval Required, Community Mailbox, Gated Community - Guard, Golf Carts OK, Playground
      • Security: Gated Community, Security Gate
      • Pet fee: $0 monthly
      • Subdivision: ISLEWORTH
      HOA
      • Has HOA: Yes
      • Amenities included: Cable TV, Gated, Playground, Security
      • Services included: 24-Hour Guard, Cable TV, Reserve Fund, Internet, Maintenance Grounds, Private Road, Security
      • HOA fee: $1,224 monthly
      • HOA name: Dan O’Connell
      • HOA phone: 407-909-2071
      Location
      • Region: Windermere

      Financial & listing details

      • Price per square foot: $1,270/sqft
      • Tax assessed value: $1,939,570
      • Annual tax amount: $19,599
      • Date on market: 4/25/2026
      • Cumulative days on market: 98 days
      • Listing terms: Cash,Conventional
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Electric utility on property: Yes
      • Road surface type: Paved

        Estimated market value

        $5,056,100

        $4.80M - $5.31M

        $7,612/mo

        Price history

        DateEventPrice
        4/25/2026Listed for sale$5,500,000+120%$1,270/sqft
        Source: Stellar MLS #O6401757 Report a problem
        9/24/2025Sold$2,500,000-13.8%$577/sqft
        Source: Stellar MLS #O6282470 Report a problem
        8/17/2025Pending sale$2,900,000$670/sqft
        Source: Stellar MLS #O6282470 Report a problem
        7/1/2025Price change$2,900,000-9.4%$670/sqft
        Source: Stellar MLS #O6282470 Report a problem
        6/21/2025Pending sale$3,200,000$739/sqft
        Source: Stellar MLS #O6282470 Report a problem
        3/1/2025Listed for sale$3,200,000-1.5%$739/sqft
        Source: Stellar MLS #O6282470 Report a problem
        3/1/2025Listing removed$3,250,000$751/sqft
        Source: Stellar MLS #O6214823 Report a problem
        10/21/2024Price change$3,250,000-6.5%$751/sqft
        Source: Stellar MLS #O6214823 Report a problem
        7/5/2024Listed for sale$3,475,000+304.1%$803/sqft
        Source: Stellar MLS #O6214823 Report a problem
        9/10/1997Sold$860,000+28.6%$199/sqft
        Source: Public Record Report a problem
        3/6/1996Sold$669,000$155/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2024$18,964 +7.2%$1,177,892 +3%
        2023$17,687 +3%$1,143,584 +3%
        2022$17,176 +1.2%$1,110,276 +3%
        2021$16,973 +0.7%$1,077,938 +1.4%
        2020$16,863 +0.8%$1,063,055 +2.3%
        2019$16,728 +0.7%$1,039,154 +1.9%
        2018$16,611 $1,019,778 -25.9%
        2017$16,611 +1.1%$1,376,011 +1.5%
        2016$16,432 +0.1%$1,355,535 +4.8%
        2015$16,410 -2.7%$1,292,962 +7.6%
        2014$16,866 +2%$1,201,684 +3.1%
        2013$16,530 +1%$1,165,453 -1.5%
        2012$16,368 +2.7%$1,183,783 -3.5%
        2011$15,943 +4.2%$1,227,134 -3.1%
        2010$15,294 $1,266,468 -3%
        2009-- $1,305,108 -12%
        2008$14,229 +1.9%$1,482,734 -3.5%
        2007$13,962 -6.3%$1,536,490 +10.9%
        2006$14,905 0%$1,385,441 +7.3%
        2005$14,906 +4.3%$1,291,057 +4.9%
        2004$14,294 +0.1%$1,230,868 +24.5%
        2003$14,276 +3.4%$988,361 +18.1%
        2002$13,801 -1.2%$836,843 +2.8%
        2001$13,971 +2.4%$813,931 +5.7%
        2000$13,646 $770,228
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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        Climate risks

        Neighborhood: 34786

        Getting around

        3 / 100
        Car-Dependent
        25 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Windermere Elem
        • Middle: Chain of Lakes Middle
        • High: Olympia High

        Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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