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Sold for $465,000
    • $465,000

    275 VIRGINIA DRIVE, WINTER GARDEN, FL 34787

    4beds
    2,004sqft
    Single Family Residence
    Built in 1955
    10,383 Square Feet Lot
    $468,300 Zestimate®
    $232/sqft
    $3,064 Estimated rent

    Home value

    $468,300

    $426,000 - $515,000

    $3,064/mo

    Zestimate® history
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    What's special

    Custom workshopPrivate entranceFresh updatesNeutral colorsCozy breakfast nookTiled bathHandy sprinkler-system
    Discover the best of community and convenience at 275 Virginia Drive! This charming, mid-century gem created treasured memories for the same owners since 1955. A perfect blend of vintage character with some fresh updates, this classic 4-bedroom, 2.5 bath ranch has been meticulously cared for and is move-in-ready, but could also present an ideal canvas for a designer’s brush. Situated on a quiet street in the golf cart district of downtown Winter Garden, this home has the benefit of being closely located to the vibrant downtown area where top-rated dining, trendy shops, and the weekly farmer’s market await. For even more recreation, the West Orange Trail is one block away for jogging and biking, or take a quick golf cart ride to appreciate the serenity of Lake Apopka. Beyond a front entrance showcasing the original owner’s beveled-glass artistry, natural light from a large picture window enhances the vintage hardwood floors and neutral colors flowing throughout the living room and secondary bedrooms. An efficient kitchen features a cozy breakfast nook adjacent to the combined great room and dining area; an ample, open space for entertainment and holiday gatherings with loved ones. The separate, primary bedroom is generous, boasting a private entrance and a full, tiled bath. The roof, HVAC, and some plumbing fixtures were replaced within the last few years and in August 2025, a new and upgraded electrical system was installed. Outside, a handy sprinkler-system helps keep the sunny front yard lush while the backyard is surrounded by mature trees and shrubbery, making it a perfect spot for little ones and four-legged friends to roam freely without worry, as well as cookouts, or just outdoor relaxation in the warm Florida weather. Creative folks will spend countless hours in the custom workshop situated on its own concrete slab, and complete with attic storage and window A/C. This shed could easily be insulated and upgraded to create a comfortable space for a hobby area, man cave or anything else to suit your needs! This charming home is brimming with nostalgia and is ready and waiting to be your new forever home. Don’t miss your chance to own a piece of Winter Garden history, schedule a private showing TODAY!!!

    Zillow last checked:

    Listing updated:

    Listed by:

    Laura Halbig 407-694-2959,

    DENIZ REALTY PARTNERS LLC 407-704-0780

    Bought with:

    Brandon Haywood, 3537815

    BHHS FLORIDA REALTY

    Source: Stellar MLS,MLS#: G5103561MLS LogoOriginating MLS: Lake and Sumter

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 4
    • Bathrooms: 3
    • Full bathrooms: 2
    • 1/2 bathrooms: 1
    Rooms
    • Room types: Family Room, Living Room
    Primary bedroom
    • Features: En Suite Bathroom, Walk-In Closet(s)
    • Level: First
    • Area: 263.31 Square Feet
    • Dimensions: 13.1x20.1
    Bedroom 2
    • Features: En Suite Bathroom, Walk-In Closet(s)
    • Level: First
    • Area: 131 Square Feet
    • Dimensions: 10x13.1
    Bedroom 3
    • Features: Ceiling Fan(s), Built-in Closet
    • Level: First
    • Area: 176.53 Square Feet
    • Dimensions: 13.9x12.7
    Bedroom 4
    • Features: Built-in Closet
    • Level: First
    • Area: 115.7 Square Feet
    • Dimensions: 9.11x12.7
    Primary bathroom
    • Features: Shower No Tub, Single Vanity
    • Level: First
    • Area: 25.46 Square Feet
    • Dimensions: 3.8x6.7
    Bathroom 2
    • Features: Single Vanity, Tub With Shower
    • Level: First
    • Area: 39.69 Square Feet
    • Dimensions: 4.9x8.1
    Bathroom 3
    • Level: First
    • Area: 19.73 Square Feet
    • Dimensions: 4.8x4.11
    Dining room
    • Level: First
    • Area: 119.21 Square Feet
    • Dimensions: 13.1x9.1
    Family room
    • Features: Ceiling Fan(s)
    • Level: First
    • Area: 400.68 Square Feet
    • Dimensions: 21.2x18.9
    Kitchen
    • Level: First
    • Area: 150.66 Square Feet
    • Dimensions: 18.6x8.1
    Living room
    • Features: Built-In Shelving
    • Level: First
    • Area: 203.36 Square Feet
    • Dimensions: 16.4x12.4
    Heating
    • Central, Heat Pump
    Cooling
    • Central Air
    Appliances
    • Included: Dishwasher, Dryer, Range, Refrigerator, Washer
    • Laundry: Inside
    Features
    • Ceiling Fan(s), Living Room/Dining Room Combo, Primary Bedroom Main Floor, Split Bedroom
    • Flooring: Carpet, Ceramic Tile, Hardwood
    • Windows: Window Treatments
    • Has fireplace: No
    Interior area
    • Total structure area: 2,091
    • Total interior livable area: 2,004 sqft

    Property

    Parking
    • Parking features: Driveway, On Street
    • Has uncovered spaces: Yes
    Features
    • Levels: One
    • Stories: 1
    • Exterior features: Irrigation System, Private Mailbox, Storage
    Lot
    • Size: 10,383 Square Feet
    • Features: Oversized Lot
    Details
    • Additional structures: Shed(s)
    • Parcel number: 142227801600310
    • Zoning: R-2
    • Special conditions: None

    Construction

    Type & style
    • Home type: SingleFamily
    • Property subtype: Single Family Residence
    Materials
    • Block
    • Foundation: Crawlspace
    • Roof: Shingle
    Condition
    • New construction: No
    • Year built: 1955

    Utilities & green energy

    • Sewer: Public Sewer
    • Water: Public
    • Utilities for property: BB/HS Internet Available, Cable Available, Electricity Available, Sewer Available, Sprinkler Meter, Water Available

    Community & HOA

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

    Financial & listing details

    • Price per square foot: $232/sqft
    • Tax assessed value: $349,278
    • Annual tax amount: $5,571
    • Date on market: 10/21/2025
    • Cumulative days on market: 129 days
    • Listing terms: Cash,Conventional,FHA,VA Loan
    • Ownership: Fee Simple
    • Total actual rent: 0
    • Electric utility on property: Yes
    • Road surface type: Asphalt, Paved

    Price history

    DateEventPrice
    12/2/2025Sold$465,000-2.1%$232/sqft
    Source: Stellar MLS #G5103561 Report a problem
    10/29/2025Pending sale$475,000$237/sqft
    Source: Stellar MLS #G5103561 Report a problem
    10/21/2025Listed for sale$475,000-2%$237/sqft
    Source: Stellar MLS #G5103561 Report a problem
    10/1/2025Listing removed$484,900$242/sqft
    Source: Stellar MLS #O6298968 Report a problem
    9/11/2025Listed for sale$484,900$242/sqft
    Source: Stellar MLS #O6298968 Report a problem
    8/25/2025Pending sale$484,900$242/sqft
    Source: Stellar MLS #O6298968 Report a problem
    6/23/2025Listed for sale$484,900$242/sqft
    Source: Stellar MLS #O6298968 Report a problem
    6/5/2025Pending sale$484,900$242/sqft
    Source: Stellar MLS #O6298968 Report a problem
    5/8/2025Listed for sale$484,900$242/sqft
    Source: Stellar MLS #O6298968 Report a problem
    4/23/2025Pending sale$484,900$242/sqft
    Source: Stellar MLS #O6298968 Report a problem
    4/11/2025Listed for sale$484,900-22.4%$242/sqft
    Source: Stellar MLS #O6298968 Report a problem
    8/29/2024Listing removed$625,000$312/sqft
    Source: Stellar MLS #O6235015 Report a problem
    8/23/2024Listed for sale$625,000+34622.2%$312/sqft
    Source: Stellar MLS #O6235015 Report a problem
    2/19/2021Listing removed--
    Source: Zillow Rental Manager Report a problem
    2/11/2021Price change$1,900-5%$1/sqft
    Source: Zillow Rental Manager Report a problem
    2/1/2021Price change$2,000-4.8%$1/sqft
    Source: Zillow Rental Manager Report a problem
    1/12/2021Price change$2,100-4.5%$1/sqft
    Source: Zillow Rental Manager Report a problem
    12/20/2020Listed for rent$2,200+18.9%$1/sqft
    Source: Owner Report a problem
    12/30/2018Sold$1,800$1/sqft
    Source: Agent Provided Report a problem
    11/23/2018Listing removed$1,850$1/sqft
    Source: SOUTHERN HERITAGE REALTY, INC #O5743281 Report a problem
    11/15/2018Price change$1,850-5.1%$1/sqft
    Source: SOUTHERN HERITAGE REALTY, INC #O5743281 Report a problem
    11/1/2018Listed for rent$1,950$1/sqft
    Source: SOUTHERN HERITAGE REALTY, INC #O5743281 Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2024$5,572 +26.1%$349,278 +25.8%
    2023$4,417 +538.1%$277,643 +138.9%
    2022$692 +4.5%$116,212 +3%
    2021$662 +2.3%$112,827 +1.4%
    2020$647 +3.3%$111,269 +2.3%
    2019$627 +3%$108,767 +1.9%
    2018$608 +3.3%$106,739 -36.1%
    2017$589 -1.3%$166,940 +7.8%
    2016$597 -3.8%$154,840 +4.3%
    2015$621 -1.8%$148,497 +19.9%
    2014$632 +3.4%$123,867 +12.3%
    2013$611 +1.2%$110,327 +0.9%
    2012$604 +3.7%$109,342 -1.8%
    2011$583 +4.7%$111,329 -7.8%
    2010$556 $120,773 -14.3%
    2009-- $140,864 -21.1%
    2008$487 -25.9%$178,547 -6%
    2007$658 -17.9%$189,886 +11.3%
    2006$801 +1.2%$170,682 +32.1%
    2005$791 +7.5%$129,173 +24.2%
    2004$736 -23.7%$104,038 +5.8%
    2003$965 +3.6%$98,295 +1.5%
    2002$931 -0.6%$96,886 +20.8%
    2001$937 +3.7%$80,208 +5.5%
    2000$903 $76,056
    Find assessor info on the county website

    Neighborhood: 34787

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    Nearby schools

    GreatSchools rating
    Schools provided by the listing agent
    • Elementary: Dillard Street 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.

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    Estimated market value
    $468,300
    Get a cash offer in 3 minutes
    Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
    Estimated market value
    $468,300

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