Back on Market! Welcome to 363 South Main Street in the heart of downtown Winchester, KY—this spacious 3-bedroom, 2-bath home offers 2,142 square feet of character, updates, and convenience. Ideally located close to all local amenities and just 5 minutes from I-64, you'll enjoy easy access to shopping, dining, and commuting. The home features beautiful hardwood floors and an updated kitchen with plenty of cabinet space, perfect for everyday living and entertaining. Recent improvements include a new roof, soffit, and gutters, along with an updated HVAC system, fresh exterior paint, professional pressure washing, and refreshed landscaping—making this property truly move-in ready. A versatile loft space provides additional storage or future potential, while the covered front porch, back deck, and fenced backyard create the perfect setup for relaxing or hosting guests. This is a rare opportunity to own a well-updated home in a prime downtown location.
Sold for $253,000
$253,000
363 S Main St, Winchester, KY 40391
3beds
2,142sqft
Single Family Residence
Built in 1940
0.49 Acres Lot
$253,100 Zestimate®
$118/sqft
$1,830 Estimated rent
Home value
$253,100
$220,000 - $291,000
$1,830/mo
Zestimate® history
Owner options
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$1,830/mo
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$1,830/mo
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$1,522/mo
Est. payment
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$1,522/mo
Est. payment
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List your homeWhat's special
Zillow last checked:
Listing updated:
Listed by:
Zachary Otis 606-336-3659,
HomeLand Real Estate Inc
Bought with:
Randy Rodriguez, 304186
TrueNorth Realty and Management
Source: Imagine MLS,MLS#: 26009123
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Primary bedroom
- Level: First
Bedroom 2
- Level: First
Bedroom 3
- Level: First
Bathroom 1
- Level: First
Bathroom 2
- Level: First
Dining room
- Level: First
Kitchen
- Level: First
Living room
- Level: First
Utility room
- Level: First
Heating
- Electric, Natural Gas
Cooling
- Ceiling Fan(s), Electric
Appliances
- Included: Refrigerator, Cooktop, Oven
Features
- Eat-in Kitchen, Walk-In Closet(s), Ceiling Fan(s)
- Flooring: Carpet, Hardwood, Tile
- Doors: Storm Door(s)
- Windows: Blinds, Screens
- Basement: Crawl Space
- Has fireplace: No
Interior area
- Total structure area: 2,142
- Total interior livable area: 2,142 sqft
- Finished area above ground: 2,142
- Finished area below ground: 0
Property
Parking
- Parking features: Driveway, Off Street
- Has uncovered spaces: Yes
Features
- Levels: One
- Fencing: Wood
- Has view: Yes
- View description: Neighborhood
Lot
- Size: 0.49 Acres
Details
- Additional structures: Shed(s)
- Parcel number: 054400204600
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Concrete Perimeter, Stone
- Roof: Shingle
Condition
- New construction: No
- Year built: 1940
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Electricity Connected, Sewer Connected, Water Connected
Community & neighborhood
Location
- Region: Winchester
- Subdivision: Thomson Addition
Price history
| Date | Event | Price |
|---|---|---|
| 6/12/2026 | Sold | $253,000+1.2%$118/sqft |
Source:  Imagine MLS #26009123 Report a problem | ||
| 5/1/2026 | Contingent | $250,000$117/sqft |
Source: Imagine MLS #26009123 Report a problem | ||
| 4/29/2026 | Listed for sale | $250,000$117/sqft |
Source: Imagine MLS #26009123 Report a problem | ||
| 4/28/2026 | Contingent | $250,000$117/sqft |
Source: Imagine MLS #26009123 Report a problem | ||
| 4/26/2026 | Listed for sale | $250,000+11.1%$117/sqft |
Source: Imagine MLS #26009123 Report a problem | ||
| 11/9/2025 | Listing removed | $225,000$105/sqft |
Source: Imagine MLS #25502680 Report a problem | ||
| 10/1/2025 | Price change | $225,000-2.1%$105/sqft |
Source: Imagine MLS #25502680 Report a problem | ||
| 9/16/2025 | Price change | $229,9000%$107/sqft |
Source: Imagine MLS #25009250 Report a problem | ||
| 9/11/2025 | Price change | $230,000-3.8%$107/sqft |
Source: Imagine MLS #25009250 Report a problem | ||
| 8/27/2025 | Listed for sale | $239,000$112/sqft |
Source: Imagine MLS #25009250 Report a problem | ||
| 8/19/2025 | Pending sale | $239,000$112/sqft |
Source: Imagine MLS #25009250 Report a problem | ||
| 7/18/2025 | Price change | $239,000-4%$112/sqft |
Source: Imagine MLS #25009250 Report a problem | ||
| 6/29/2025 | Price change | $249,000-3.9%$116/sqft |
Source: Imagine MLS #25009250 Report a problem | ||
| 5/19/2025 | Price change | $259,000-5.8%$121/sqft |
Source: Imagine MLS #25009250 Report a problem | ||
| 5/5/2025 | Listed for sale | $275,000+97.1%$128/sqft |
Source: Imagine MLS #25009250 Report a problem | ||
| 10/19/2017 | Sold | $139,500-6.3%$65/sqft |
Source: Imagine MLS #1719612 Report a problem | ||
| 9/5/2017 | Pending sale | $148,900$70/sqft |
Source: Better Homes and Gardens Real Estate Cypress #1719612 Report a problem | ||
| 8/27/2017 | Listed for sale | $148,900+11.5%$70/sqft |
Source: Better Homes & Gardens, Cypres #1719612 Report a problem | ||
| 9/10/2010 | Sold | $133,527+161.8%$62/sqft |
Source:  Imagine MLS #1012306 Report a problem | ||
| 5/29/2009 | Sold | $51,000$24/sqft |
Source: Imagine MLS #823258 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $1,395 +1.5% | $139,500 |
| 2023 | $1,374 | $139,500 |
| 2022 | $1,374 +0.3% | $139,500 |
| 2021 | $1,370 -0.2% | $139,500 |
| 2020 | $1,373 +574.1% | $139,500 |
| 2019 | $204 | $139,500 |
| 2018 | $204 | $139,500 +4.5% |
| 2017 | $204 +4.5% | $133,500 |
| 2016 | $195 | $133,500 |
| 2015 | $195 | $133,500 |
| 2013 | $195 | $133,500 |
| 2011 | -- | $133,500 |
| 2010 | -- | $133,500 |
Find assessor info on the county website
Neighborhood: 40391
Nearby schools
GreatSchools rating
- 5/10Shearer Elementary SchoolGrades: K-4Distance: 0.6 mi
- 5/10Robert D Campbell Junior High SchoolGrades: 7-8Distance: 0.8 mi
- 5/10George Rogers Clark High SchoolGrades: 9-12Distance: 2.5 mi
Schools provided by the listing agent
- Elementary: Shearer
- Middle: Robert Campbell
- High: GRC
Source: Imagine 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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$253,100
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+$5,062
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$258,162
- Kentucky
- Clark County
- Winchester
- 40391
- 363 S Main St
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