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Off market
  • $456,700

    418 Charles St, Winter Garden, FL 34787

    5beds
    2,239sqft
    Single Family Residence
    Built in ----
    -- sqft lot
    $456,700 Zestimate®
    $204/sqft
    $3,320 Estimated rent

    Home value

    $456,700

    $416,000 - $502,000

    $3,320/mo

    Zestimate® history
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    What's special

    Fenced yardTwo-car garageOpen-concept floor planNearby parksStainless steel appliancesGenerous closet space

    Luxury and Character: Main 3Bedrooms/2Bath PLUS 2Bedrooms/1Bath in-law suite! Nestled in the highly desirable Golf Cart District, this charming home offers the perfect blend of character, culture, and convenience in the heart of Downtown Winter Garden. This beautifully maintained residence is thoughtfully designed as two fully independent living spaces, featuring a 3-bedroom, 2-bath main home plus a private 2-bedroom, 1-bath mother-in-law suiteideal for multigenerational living, guests, or income-producing flexibility. Inside the main home, the open-concept floor plan creates a seamless flow between the living, dining, and kitchen areas, making it perfect for both everyday living and entertaining. The kitchen is thoughtfully appointed with granite countertops and stainless steel appliances, offering a modern, functional space for cooking and gathering. Each bedroom is filled with natural light and offers generous closet space, ensuring comfort and versatility throughout. A two-car garage adds convenience and additional storage. What truly sets this property apart is its dual-living design with complete separation and privacy. The private 2/1 in-law suite, located on the right side of the home, functions as a fully self-contained residenceperfect for extended family, elderly parents, adult children, or guests seeking true independence while staying close. Step outside and enjoy a lifestyle that feels straight out of a postcard. Just moments away, Downtown Winter Garden offers a vibrant yet welcoming atmosphere filled with locally owned boutiques, award-winning restaurants, cozy coffee shops, breweries, and the beloved Plant Street Market. Weekends come alive with the renowned Winter Garden Farmers Market, live music, and seasonal community events along the historic brick-lined streets. For outdoor enthusiasts, immediate access to the West Orange Trail, a scenic 22-mile paved trail, invites walking, jogging, and biking through beautiful Central Florida landscapes. Nearby parks and year-round community events enhance the area's strong sense of charm and connection. Despite its quaint hometown feel, this location also provides quick and easy access to major highways, making commutes to Orlando, area theme parks, and surrounding communities effortless. This is a rare opportunity to enjoy the energy of downtown living while coming home to space, privacy, and a truly flexible dual-living layout designed for modern life. **Resident Benefits Package (RBP) $59/month** All residents are enrolled in the Resident Benefits Package, which includes: * Liability insurance * Credit building to help improve your credit score with on-time rent payments * Up to $1 million in identity theft protection * Move-in concierge service for easy utility and home service setup * Best-in-class resident rewards program * On-demand pest control * HVAC air filter delivery * And more (full details provided upon application) **Additional Details** * Security deposit-free option available for qualified tenants through **Obligo** * Application fee: 80 per applicant** (18 years and older) * One-time admin fee: 295 upon approval** Amenities: fenced yard, in-law suite

    This property is off market, which means it's not currently listed for sale or rent on Zillow. This may be different from what's available on other websites or public sources.

    Zillow last checked:

    Listing updated:

    Source: Zillow Rentals

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 5
    • Bathrooms: 3
    • Full bathrooms: 3
    Heating
    • Forced Air
    Cooling
    • Central Air
    Appliances
    • Included: Dishwasher, Dryer, Range Oven, Refrigerator, Washer
    • Laundry: In Unit
    Features
    • Flooring: Tile
    Interior area
    • Total interior livable area: 2,239 sqft

    Property

    Parking
    • Parking features: Attached
    • Has attached garage: Yes
    • Details: Contact manager
    Features
    • Patio & porch: Porch
    • Exterior features: Heating system: ForcedAir
    Details
    • Parcel number: 272223794809130

    Construction

    Type & style
    • Home type: SingleFamily
    • Property subtype: Single Family Residence

    Community & HOA

    Community
    • Deposit fee: $2,600
    • Application fee: $80
    Location
    • Region: Winter Garden

    Financial & listing details

    • Price per square foot: $204/sqft
    • Tax assessed value: $308,972
    • Annual tax amount: $4,929
    • Date on market: 4/2/2026
    • Lease term: 1 Year

    Price history

    DateEventPrice
    4/2/2026Listing removed$2,500$1/sqft
    Source: Zillow Rentals Report a problem
    3/26/2026Price change$2,500-3.8%$1/sqft
    Source: Zillow Rentals Report a problem
    1/21/2026Listed for rent$2,600-8.8%$1/sqft
    Source: Zillow Rentals Report a problem
    9/17/2024Listing removed$2,850$1/sqft
    Source: Zillow Rentals Report a problem
    9/6/2024Price change$2,850-4.2%$1/sqft
    Source: Zillow Rentals Report a problem
    8/29/2024Price change$2,975-0.8%$1/sqft
    Source: Zillow Rentals Report a problem
    8/20/2024Price change$3,000-6.3%$1/sqft
    Source: Zillow Rentals Report a problem
    8/16/2024Listed for rent$3,200+60%$1/sqft
    Source: Zillow Rentals Report a problem
    6/27/2024Listing removed--
    Source: Zillow Rentals Report a problem
    6/23/2024Listed for rent$2,000$1/sqft
    Source: Zillow Rentals Report a problem
    11/18/2022Sold$350,000-6.7%$156/sqft
    Source: Public Record Report a problem
    10/15/2022Price change$375,000-2.6%$167/sqft
    Source: Stellar MLS #O6059198 Report a problem
    9/26/2022Pending sale$385,000$172/sqft
    Source: Stellar MLS #O6059198 Report a problem
    9/12/2022Listed for sale$385,000+54%$172/sqft
    Source: Stellar MLS #O6059198 Report a problem
    9/14/2021Listing removed--
    Source: Stellar MLS #O5967657 Report a problem
    8/21/2021Listed for sale$250,000+25%$112/sqft
    Source: Stellar MLS #O5967657 Report a problem
    8/6/2021Sold$200,000+316.7%$89/sqft
    Source: Public Record Report a problem
    8/24/2000Sold$48,000$21/sqft
    Source: Public Record Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2024$4,929 +3.8%$308,972 +3.5%
    2023$4,749 +75.2%$298,464 +75.9%
    2022$2,710 +73.6%$169,706 +76.9%
    2021$1,561 +4.4%$95,956 +5.2%
    2020$1,495 +2.4%$91,188 +5.5%
    2019$1,460 +4.3%$86,394 +10%
    2018$1,400 $78,540 -0.8%
    2017$1,400 +11.3%$79,205 +21%
    2016$1,258 +12.5%$65,480 +2.3%
    2015$1,118 +16.8%$64,008 +19.3%
    2014$958 +3.5%$53,644 +2.9%
    2013$925 +0%$52,140 +0.7%
    2012$925 -2.8%$51,789 -2.4%
    2011$952 -12.1%$53,065 -14.9%
    2010$1,083 $62,352 -27.9%
    2009-- $86,491 -21.8%
    2008$1,744 -7.4%$110,641 -7.6%
    2007$1,883 -6.6%$119,696 +4.1%
    2006$2,016 +21.2%$114,971 +25.3%
    2005$1,664 +14.6%$91,789 +13.3%
    2004$1,451 +6.5%$81,048 +8.6%
    2003$1,363 -6.9%$74,641 -7%
    2002$1,464 +9.4%$80,253 +12.8%
    2001$1,338 +152.3%$71,159 +5.5%
    2000$530 $67,470
    Find assessor info on the county website

    Neighborhood: 34787

    Nearby schools

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    Estimated market value
    $456,700
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    Estimated market value
    $456,700