Skip main navigation
For sale
    • Price cut: $10K (7/17)
    $410,000

    420 E CYPRESS STREET, WINTER GARDEN, FL 34787

    3beds
    1,616sqft
    : 
    $2,744/mo
    Get pre-qualified
    Single Family Residence
    Built in 1950
    8,440 Square Feet Lot
    $403,400 Zestimate®
    $254/sqft
    $-- HOA

    What's special

    Fully furnishedBeautifully updated kitchenNew roofEnergy-efficient double-pane windowsOversized lotSpacious fully fenced backyardAll-new flooring
    Welcome to this stunning, fully renovated and fully furnished home, perfectly situated on an oversized lot in one of Winter Garden's most exciting and rapidly growing areas. Whether you're looking for a primary residence, a turnkey investment, or a second home, this move-in-ready property offers the perfect blend of comfort, style, and convenience. Inside, you'll find an open-concept floor plan filled with natural light, featuring all-new flooring, recessed lighting throughout, energy-efficient double-pane windows, and a beautifully updated kitchen complete with stainless steel appliances. Major improvements include a new roof and a 3.5-ton AC system, providing peace of mind for years to come. Step outside and enjoy the spacious, fully fenced backyard, offering plenty of room for entertaining, pets, play, or simply relaxing outdoors. Located just one mile from Historic Downtown Winter Garden, you'll enjoy easy access to award-winning dining, shopping, farmers markets, and community events, all while living in a welcoming, family-friendly neighborhood. Fully furnished, beautifully updated, and truly move-in ready, this home offers a rare opportunity to enjoy all that Winter Garden has to offer from day one.
    73 days
    |
    1,454
    |
    93
    |

    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    Trevor Zwick 863-303-6114,

    KELLER WILLIAMS ELITE PARTNERS III REALTY 321-527-5111

    Source: Stellar MLS,MLS#: O6412414MLS LogoOriginating MLS: Lake and Sumter

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 2
      • Full bathrooms: 2
      Primary bedroom
      • Features: Dual Sinks, En Suite Bathroom, Shower No Tub, Dual Closets
      • Level: First
      Kitchen
      • Features: Breakfast Bar
      • Level: First
      Living room
      • Level: First
      Heating
      • Central
      Cooling
      • Central Air
      Appliances
      • Included: Dishwasher, Microwave, Range, Refrigerator
      • Laundry: Other
      Features
      • Kitchen/Family Room Combo, Stone Counters, Vaulted Ceiling(s)
      • Flooring: Luxury Vinyl
      • Has fireplace: No
      Interior area
      • Total structure area: 1,616
      • Total interior livable area: 1,616 sqft
      Video & virtual tour

      Property

      Features
      • Levels: One
      • Stories: 1
      • Exterior features: Lighting, Other
      • Fencing: Fenced,Vinyl
      Lot
      • Size: 8,440 Square Feet
      Details
      • Parcel number: 122227649620028
      • Zoning: R-2
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Stucco, Wood Frame
      • Foundation: Slab
      • Roof: Shingle
      Condition
      • New construction: No
      • Year built: 1950

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: Electricity Available

      Community & HOA

      Community
      • Pet fee: $0 monthly
      • Subdivision: OVERSTREET CRATE
      HOA
      • Has HOA: No
      Location
      • Region: Winter Garden

      Financial & listing details

      • Price per square foot: $254/sqft
      • Tax assessed value: $292,192
      • Annual tax amount: $5,517
      • Date on market: 6/1/2026
      • Cumulative days on market: 71 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

        $403,400

        $383,000 - $424,000

        $2,578/mo

        Price history

        DateEventPrice
        7/17/2026Price change$410,000-2.4%$254/sqft
        Source: Stellar MLS #O6412414 Report a problem
        6/18/2026Price change$420,000-1.2%$260/sqft
        Source: Stellar MLS #O6412414 Report a problem
        6/1/2026Listed for sale$425,000+6.3%$263/sqft
        Source: Stellar MLS #O6412414 Report a problem
        4/11/2024Sold$399,900$247/sqft
        Source: Stellar MLS #O6171645 Report a problem
        3/13/2024Pending sale$399,900$247/sqft
        Source: Stellar MLS #O6171645 Report a problem
        3/6/2024Price change$399,900-13%$247/sqft
        Source: Stellar MLS #O6171645 Report a problem
        1/18/2024Listed for sale$459,900-4.2%$285/sqft
        Source: Stellar MLS #O6171645 Report a problem
        11/15/2023Listing removed--
        Source: Stellar MLS #O6117198 Report a problem
        9/13/2023Price change$479,900-8.6%$297/sqft
        Source: Stellar MLS #O6117198 Report a problem
        7/27/2023Price change$524,900-6.3%$325/sqft
        Source: Stellar MLS #O6117198 Report a problem
        7/7/2023Price change$559,900-2.6%$346/sqft
        Source: Stellar MLS #O6117198 Report a problem
        6/9/2023Listed for sale$574,900+187.5%$356/sqft
        Source: Stellar MLS #O6117198 Report a problem
        5/11/2021Listing removed--
        Source: Stellar MLS #O5914433 Report a problem
        2/4/2021Sold$200,000$124/sqft
        Source: Public Record Report a problem
        1/13/2021Pending sale$200,000$124/sqft
        Source: Stellar MLS #O5914433 Report a problem
        1/13/2021Listed for sale$200,000$124/sqft
        Source: Stellar MLS #O5914433 Report a problem
        1/13/2021Pending sale$200,000$124/sqft
        Source: Stellar MLS #O5914433 Report a problem
        1/10/2021Listed for sale$200,000+32.5%$124/sqft
        Source: Stellar MLS #O5914433 Report a problem
        5/22/2018Sold$151,000-5.6%$93/sqft
        Source: Public Record Report a problem
        2/7/2018Listing removed$159,900$99/sqft
        Source: RISING REALTY OF SOUTH FLORIDA #T2910908 Report a problem
        1/18/2018Price change$159,900-5.9%$99/sqft
        Source: RISING REALTY OF SOUTH FLORIDA #T2910908 Report a problem
        1/2/2018Price change$169,900-5.6%$105/sqft
        Source: RISING REALTY OF SOUTH FLORIDA #T2910908 Report a problem
        12/2/2017Price change$179,900-5.3%$111/sqft
        Source: RISING REALTY OF SOUTH FLORIDA #T2910908 Report a problem
        10/27/2017Listed for sale$189,900+108.7%$118/sqft
        Source: RISING REALTY OF SOUTH FLORIDA #T2910908 Report a problem
        6/15/2017Listing removed$90,993$56/sqft
        Source: Auction.com Report a problem
        5/23/2017Listed for sale--
        Source: Auction.com Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2024$4,881 +27.8%$279,362 +25.7%
        2023$3,818 +12.5%$222,179 +10%
        2022$3,394 +88.4%$201,981 +46.9%
        2021$1,802 +1.2%$137,481 +1.4%
        2020$1,781 +2%$135,583 +2.3%
        2019$1,745 -25.1%$132,535 +3.6%
        2018$2,330 $127,948 +85%
        2017$2,330 +75.9%$69,154 +18.2%
        2016$1,324 +11.1%$58,517 +2.5%
        2015$1,192 +96.3%$57,100 +10.5%
        2014$607 +2.4%$51,654 +2.3%
        2013$593 +1.9%$50,473 +0.6%
        2012$582 +3.9%$50,161 +6.4%
        2011$560 +4%$47,146 -18.6%
        2010$539 $57,947 -14.3%
        2009-- $67,643 -21.4%
        2008$498 +18.9%$86,057 -13.7%
        2007$419 -1.4%$99,707 +7.4%
        2006$425 +6.9%$92,853 +82.7%
        2005$398 +7.6%$50,835 +2.8%
        2004$370 +3%$49,460 +12.5%
        2003$359 +4.7%$43,971 +4%
        2002$343 $42,286
        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.
        See how much you could borrow to make a competitive offer.
        Get pre-qualified

        Climate risks

        Neighborhood: 34787

        Getting around

        74 / 100
        Very Walkable
        62 / 100
        Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Maxey Elem
        • Middle: Lakeview Middle
        • High: West Orange High

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

        A local agent can set up tours, give advice and negotiate with sellers.

        Browse local experts

        Similar homes

              Nearby cities

              Nearby neighborhoods

              Nearby zip codes

              Other Winter Garden Topics

                Search
                Updates
                Favorites
                Plan
                Inbox