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Under contract
    • $245,000

    1638 WINDSOR OAK COURT, KISSIMMEE, FL 34744

    3beds
    1,380sqft
    : 
    $1,810/mo
    Get pre-qualified
    Townhouse
    Built in 1999
    871 Square Feet Lot
    $-- Zestimate®
    $178/sqft
    $180/mo HOA

    What's special

    Modern fixturesCommunity poolNew garbage disposalFarmhouse sinkNew cabinets
    Under contract-accepting backup offers. Whether you live here year-round or use it as your Florida escape, this property offers the best of both worlds, personal enjoyment and rental income potential when you’re away. Welcome to this beautifully maintained and fully upgraded townhome in the heart of Kissimmee, located in the quiet, gated community of Windsor Oaks. This spacious 3-bedroom, 2.5-bath home features a flexible layout with two master suites upstairs and a third bedroom on the main level that can also serve as a home office, den, or gym. Major improvements give this home incredible value and peace of mind: the roof was replaced just 8 months ago, the A/C is only 2 years old, the water heater is brand new, the sliding glass door recently installed new, and all appliances including washer and dryer are included.You’ll find a bright and inviting open-concept living and dining area that flows seamlessly into the kitchen. The kitchen has been fully upgraded with new cabinets, modern fixtures, a farmhouse sink, quartz countertops with a beautiful backsplash, and a new garbage disposal. All bathrooms feature new cabinetry and fixtures, while the upstairs and bedrooms are finished with new laminate flooring. Windsor Oaks provides a low HOA, short-term rental approval, and a community pool, making this property ideal for investors and first-time homeowners alike. With shops, restaurants, and entertainment nearby, this home blends modern upgrades with everyday convenience.
    25 days
    |
    470
    |
    34
    |

    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    Lissette Escobar 407-340-8115,

    PREFERRED REAL ESTATE BROKERS 407-440-4900

    Source: Stellar MLS,MLS#: S5153418MLS LogoOriginating MLS: Orlando Regional

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 3
      • Full bathrooms: 2
      • 1/2 bathrooms: 1
      Rooms
      • Room types: Utility Room
      Primary bedroom
      • Features: Walk-In Closet(s)
      • Level: Second
      • Area: 196 Square Feet
      • Dimensions: 14x14
      Bedroom 2
      • Features: Ceiling Fan(s), Built-in Closet
      • Level: First
      • Area: 90 Square Feet
      • Dimensions: 9x10
      Bedroom 3
      • Features: Built-in Closet
      • Level: Second
      • Area: 196 Square Feet
      • Dimensions: 14x14
      Primary bathroom
      • Features: Ceiling Fan(s)
      • Level: Second
      Bathroom 2
      • Level: Second
      Bathroom 3
      • Level: First
      Balcony porch lanai
      • Level: First
      Dining room
      • Level: First
      Kitchen
      • Features: Stone Counters
      • Level: First
      • Area: 90 Square Feet
      • Dimensions: 9x10
      Living room
      • Features: Ceiling Fan(s)
      • Level: First
      • Area: 210 Square Feet
      • Dimensions: 15x14
      Heating
      • Electric
      Cooling
      • Central Air
      Appliances
      • Included: Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
      • Laundry: In Kitchen, Inside, Laundry Closet
      Features
      • Ceiling Fan(s), Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, PrimaryBedroom Upstairs, Solid Surface Counters, Solid Wood Cabinets, Thermostat, Walk-In Closet(s)
      • Flooring: Ceramic Tile, Laminate
      • Doors: Sliding Doors
      • Windows: Window Treatments
      • Has fireplace: No
      Interior area
      • Total structure area: 1,490
      • Total interior livable area: 1,380 sqft
      Video & virtual tour

      Property

      Features
      • Levels: Two
      • Stories: 2
      • Patio & porch: Covered, Enclosed, Porch, Rear Porch, Screened
      • Exterior features: Lighting, Rain Gutters, Sidewalk
      Lot
      • Size: 871 Square Feet
      • Features: Private, Sidewalk
      • Residential vegetation: Trees/Landscaped
      Details
      • Parcel number: 142529236500010120
      • Zoning: KSRP
      • Special conditions: None

      Construction

      Type & style
      • Home type: Townhouse
      • Architectural style: Contemporary
      • Property subtype: Townhouse
      Materials
      • Block, Stucco
      • Foundation: Slab
      • Roof: Shingle
      Condition
      • New construction: No
      • Year built: 1999

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: Cable Available, Electricity Available, Public, Sewer Connected, Street Lights, Water Available

      Community & HOA

      Community
      • Features: Deed Restrictions, Gated Community - No Guard, Pool, Sidewalks
      • Security: Fire Sprinkler System, Gated Community, Smoke Detector(s)
      • Pet fee: $0 monthly
      • Subdivision: WINDSOR OAKS
      HOA
      • Has HOA: Yes
      • Services included: Community Pool, Pool Maintenance, Private Road
      • HOA fee: $180 monthly
      • HOA name: Leslie Ludlam / AMG of Central Florida
      • HOA phone: 407-847-9950
      Location
      • Region: Kissimmee

      Financial & listing details

      • Price per square foot: $178/sqft
      • Tax assessed value: $186,200
      • Annual tax amount: $2,008
      • Date on market: 7/9/2026
      • Cumulative days on market: 26 days
      • Listing terms: Cash,Conventional,FHA,VA Loan
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Electric utility on property: Yes
      • Road surface type: Paved

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        7/16/2026Contingent$245,000$178/sqft
        Source: Stellar MLS #S5153418 Report a problem
        7/10/2026Listed for sale$245,000-7.5%$178/sqft
        Source: Stellar MLS #S5153418 Report a problem
        5/1/2026Listing removed$265,000$192/sqft
        Source: Stellar MLS #S5133782 Report a problem
        3/11/2026Listed for sale$265,000$192/sqft
        Source: Stellar MLS #S5133782 Report a problem
        3/7/2026Pending sale$265,000$192/sqft
        Source: Stellar MLS #S5133782 Report a problem
        2/11/2026Price change$265,000-7%$192/sqft
        Source: Stellar MLS #S5133782 Report a problem
        12/13/2025Price change$284,900-3.4%$206/sqft
        Source: Stellar MLS #S5133782 Report a problem
        9/5/2025Listed for sale$295,000+288.2%$214/sqft
        Source: Stellar MLS #S5133782 Report a problem
        9/3/2014Sold$76,000-3.8%$55/sqft
        Source: Public Record Report a problem
        9/3/2014Pending sale$79,000$57/sqft
        Source: PRUDENTIAL RESULTS REALTY #S4724823 Report a problem
        8/7/2014Price change$79,000-1.1%$57/sqft
        Source: Prudential Results Realty #S4724823 Report a problem
        7/24/2014Price change$79,900-3.9%$58/sqft
        Source: Prudential Results Realty #S4724823 Report a problem
        6/20/2014Price change$83,100-4.9%$60/sqft
        Source: Prudential Results Realty #S4724823 Report a problem
        5/21/2014Price change$87,400-5%$63/sqft
        Source: Prudential Results Realty #S4724823 Report a problem
        5/18/2014Listed for sale$92,000-27%$67/sqft
        Source: Prudential Results Realty #S4724823 Report a problem
        3/4/2005Sold$126,000+40.2%$91/sqft
        Source: Public Record Report a problem
        11/4/2002Sold$89,900$65/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$2,298 +14.4%$186,200 -1.8%
        2024$2,008 +3%$189,600 +14.1%
        2023$1,949 +4.1%$166,200 +11.8%
        2022$1,873 -1.5%$148,700 +11.6%
        2021$1,900 +8%$133,200 +7.9%
        2020$1,759 +12.3%$123,500 +20.1%
        2019$1,567 $102,800 +48.3%
        2018$1,567 +21.8%$69,300 +2.7%
        2017$1,287 +0.7%$67,500 +1%
        2016$1,279 +0.1%$66,800 +9.7%
        2015$1,277 +7.4%$60,900 +17.8%
        2014$1,189 $51,700 +2.8%
        2013-- $50,300 -0.6%
        2012-- $50,600 -5.8%
        2011-- $53,700 -7.7%
        2010-- $58,200 -45.2%
        2009-- $106,200 -10.2%
        2008-- $118,310 +54.1%
        2004-- $76,750
        2003-- $76,750
        Find assessor info on the county website

        Monthly payment

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        Payment breakdown

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        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: 34744

        Getting around

        19 / 100
        Car-Dependent
        30 / 100
        Some Transit
        39 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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