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For sale
    • Price cut: $25K (9/15)
    $625,000

    2540 WINNERS CIRCLE, KISSIMMEE, FL 34744

    4beds
    3,246sqft
    : 
    $4,282/mo
    Get pre-qualified
    Single Family Residence
    Built in 2000
    0.5 Acres Lot
    $622,400 Zestimate®
    $193/sqft
    $-- HOA

    What's special

    Private poolTwo-car attached garageSpacious two-story pool homePrivate backyard retreatStandout curb appealTile roofMature landscaping
    Virtually Staged. **WELCOME HOME** NO HOA, HALF AN ACRE of land, a PRIVATE POOL, and a full SEPARATE APARTMENT on the main floor – welcome to your next chapter on Winners Circle in the Winners Park community of Kissimmee! EXTERIOR PAINT (2023), NEW WINDOWS (2022), DETACHED AIR CONDITIONED GARAGE (2022), septic tank serviced (2022) – big-ticket items are already started, giving you confidence and flexibility from day one. Situated on an expansive .50 ACRE LOT, this spacious two-story POOL HOME delivers over 3,000 square feet of living space, mature landscaping, a TILE ROOF, long paver driveway, and standout curb appeal. The SCREENED POOL with PAVER DECK creates a private backyard retreat with room to entertain, garden, or just spread out. Inside, the flexible layout is ideal for large households, multi-generational living, or anyone needing versatile space. The full first-floor apartment includes its own kitchen open to a living area, bedroom, and full bath – perfect for in-laws, guests, extended stays, or even creative work from home options! The main home features comfortable formal and family spaces, a well-equipped kitchen with casual dining, and an expansive FLORIDA ROOM complete with a full bath and cozy office space – offering endless possibilities for hobbies, remote work, or additional entertaining. Upstairs, a BONUS/LOFT anchors the remaining bedrooms, while the generous PRIMARY SUITE provides a peaceful escape with an updated private en-suite bath. Car enthusiasts, hobbyists, or entrepreneurs will appreciate the two-car attached garage plus the like-new detached, air-conditioned garage – currently used as a dojo, but easily transformed into a workshop, craft studio, gym, or business space. Updated yet still offering room to personalize, this home offers the rare combination of space, privacy, flexibility, and location. Perfectly situated just off Simpson Road, you will enjoy easy access to the Florida Turnpike, shopping, dining, area lakes, attractions, and world-famous theme parks – all while coming home to a quiet, established neighborhood with no HOA restrictions. Room to grow inside and out. Versatility for today and tomorrow. Schedule your tour today and be the winner on Winners Circle! **Seller may consider buyer concessions if made in an offer**
    218 days
    800
    115

    Zillow last checked:

    Listing updated:

    Listed by:

    Jenny Wemert 407-809-1193,

    WEMERT GROUP REALTY LLC 407-743-8356,

    Paul Michelotti 407-797-7388,

    WEMERT GROUP REALTY LLC

    Source: Stellar MLS,MLS#: O6382446MLS LogoOriginating MLS: Orlando Regional

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 5
      • Full bathrooms: 4
      • 1/2 bathrooms: 1
      Rooms
      • Room types: Bonus Room, Den/Library/Office, Family Room, Florida Room, Dining Room, Living Room, Loft
      Primary bedroom
      • Features: Ceiling Fan(s), En Suite Bathroom, Walk-In Closet(s)
      • Level: Second
      • Area: 182 Square Feet
      • Dimensions: 14x13
      Bedroom 2
      • Features: Ceiling Fan(s), Built-in Closet
      • Level: Second
      • Area: 154 Square Feet
      • Dimensions: 14x11
      Bedroom 3
      • Features: Ceiling Fan(s), Built-in Closet
      • Level: Second
      • Area: 132 Square Feet
      • Dimensions: 12x11
      Bedroom 4
      • Features: Ceiling Fan(s), Built-in Closet
      • Level: First
      • Area: 110 Square Feet
      • Dimensions: 11x10
      Primary bathroom
      • Level: Second
      • Area: 117 Square Feet
      • Dimensions: 13x9
      Dining room
      • Features: Ceiling Fan(s)
      • Level: First
      • Area: 144 Square Feet
      • Dimensions: 12x12
      Family room
      • Features: Ceiling Fan(s)
      • Level: First
      • Area: 221 Square Feet
      • Dimensions: 17x13
      Kitchen
      • Features: Breakfast Bar, Pantry
      • Level: First
      • Area: 264 Square Feet
      • Dimensions: 22x12
      Kitchen
      • Level: First
      • Area: 140 Square Feet
      • Dimensions: 14x10
      Living room
      • Features: Ceiling Fan(s)
      • Level: First
      • Area: 160 Square Feet
      • Dimensions: 16x10
      Living room
      • Features: Ceiling Fan(s)
      • Level: First
      • Area: 144 Square Feet
      • Dimensions: 12x12
      Loft
      • Features: Ceiling Fan(s)
      • Level: Second
      Heating
      • Central, Electric
      Cooling
      • Central Air
      Appliances
      • Included: Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer, Water Filtration System, Water Softener
      • Laundry: In Garage
      Features
      • Ceiling Fan(s), Eating Space In Kitchen, Kitchen/Family Room Combo, Living Room/Dining Room Combo, PrimaryBedroom Upstairs, Solid Surface Counters, Stone Counters, Walk-In Closet(s), In-Law Floorplan
      • Flooring: Carpet, Tile
      • Doors: Sliding Doors
      • Windows: Window Treatments, Hurricane Shutters
      • Has fireplace: No
      Interior area
      • Total structure area: 3,710
      • Total interior livable area: 3,246 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 4
      • Parking features: Boat, Curb Parking, Driveway, Garage Door Opener, Golf Cart Parking, Ground Level, Guest, On Street, Oversized, Parking Pad, RV Access/Parking
      • Attached garage spaces: 4
      • Has uncovered spaces: Yes
      Features
      • Levels: Two
      • Stories: 2
      • Patio & porch: Covered, Enclosed, Front Porch, Patio, Rear Porch
      • Exterior features: Lighting, Private Mailbox, Rain Gutters, Storage
      • Has private pool: Yes
      • Pool features: Auto Cleaner, Gunite, In Ground, Lighting, Screen Enclosure
      Lot
      • Size: 0.5 Acres
      • Features: Cul-De-Sac, Landscaped, Oversized Lot, Street Dead-End
      • Residential vegetation: Fruit Trees, Mature Landscaping, Trees/Landscaped
      Details
      • Additional structures: Other, Shed(s), Workshop
      • Parcel number: 172530551500010060
      • Zoning: OR1C
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Block, Stucco
      • Foundation: Slab
      • Roof: Tile
      Condition
      • New construction: No
      • Year built: 2000

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Public
      • Utilities for property: BB/HS Internet Available, Cable Available, Electricity Connected, Fiber Optics, Water Connected

      Community & HOA

      Community
      • Pet fee: $0 monthly
      • Subdivision: WINNERS PARK
      HOA
      • Has HOA: No
      Location
      • Region: Kissimmee

      Financial & listing details

      • Price per square foot: $193/sqft
      • Tax assessed value: $382,800
      • Annual tax amount: $3,688
      • Date on market: 2/19/2026
      • Cumulative days on market: 148 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

        $622,400

        $591,000 - $654,000

        $3,863/mo

        Price history

        DateEventPrice
        9/15/2026Price change$625,000-3.8%$193/sqft
        Source: Stellar MLS #O6382446 Report a problem
        8/30/2026Pending sale$650,000$200/sqft
        Source: Stellar MLS #O6382446 Report a problem
        8/11/2026Listed for sale$650,000$200/sqft
        Source: Stellar MLS #O6382446 Report a problem
        7/8/2026Contingent$650,000$200/sqft
        Source: Stellar MLS #O6382446 Report a problem
        7/6/2026Pending sale$650,000$200/sqft
        Source: Stellar MLS #O6382446 Report a problem
        7/3/2026Price change$650,000-5.7%$200/sqft
        Source: Stellar MLS #O6382446 Report a problem
        6/23/2026Price change$689,000-1.4%$212/sqft
        Source: Stellar MLS #O6382446 Report a problem
        5/28/2026Price change$699,000-3.6%$215/sqft
        Source: Stellar MLS #O6382446 Report a problem
        5/13/2026Price change$725,000-1.9%$223/sqft
        Source: Stellar MLS #O6382446 Report a problem
        3/28/2026Price change$739,000-1.5%$228/sqft
        Source: Stellar MLS #O6382446 Report a problem
        3/3/2026Price change$750,000-6.3%$231/sqft
        Source: Stellar MLS #O6382446 Report a problem
        2/19/2026Listed for sale$800,000+308.2%$246/sqft
        Source: Stellar MLS #O6382446 Report a problem
        12/20/2022Listing removed--
        Source: Zillow Rentals Report a problem
        12/16/2022Listed for rent$1,300
        Source: Zillow Rentals Report a problem
        5/1/2003Sold$196,000+684%$60/sqft
        Source: Public Record Report a problem
        7/15/1996Sold$25,000$8/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$3,688 +5.3%$382,800 -0.2%
        2024$3,503 +2.4%$383,600 +1.6%
        2023$3,422 +4.4%$377,500 +12.9%
        2022$3,277 +1.2%$334,300 +12.7%
        2021$3,239 -34.2%$296,600 +9.9%
        2020$4,922 +32.7%$269,900 +6.3%
        2019$3,710 $253,800 +3.8%
        2018$3,710 $244,555 +2.1%
        2017-- $239,525 +2.1%
        2016$3,672 +1.1%$234,599 +0.7%
        2015$3,632 +8.3%$232,969 +0.8%
        2014$3,353 $231,121 +1.5%
        2013-- $227,706 +1.7%
        2012-- $223,900 -3.2%
        2011-- $231,200 -4.8%
        2010-- $242,900 -18%
        2009-- $296,200 -23.5%
        2008-- $387,200 +116.5%
        2002$2,512 +1.9%$178,878 +1.6%
        2001$2,464 +515.8%$176,061 +633.6%
        2000$400 $24,000
        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.
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        Climate risks

        Neighborhood: 34744

        Getting around

        23 / 100
        Minimal Transit

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: East Lake Elem
        • Middle: Neptune Middle (6-8)
        • High: Tohopekaliga High School

        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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