382 S Main St, Winchester, KY 40391
Home value
$370,200
$337,000 - $407,000
$2,098/mo
Owner options
$2,098/mo
Rent Zestimate®
Find your next renter with Zillow Rental Manager. Plus, with online applications, you can quickly screen prospective tenants – for free.
$2,098/mo
Rent Zestimate®
$1,789/mo
Est. payment
Refinancing to a lower rate could help reduce your monthly payments and save thousands over the life of the loan.
$1,789/mo
Est. payment
Explore your selling options
Work with a Zillow partner agent
Leverage their expertise and Zillow's premium Showcase listings to get your home seen by more buyers.
Get startedList with your own agent
Get your home in front of millions of buyers by listing it on Zillow.
Learn how to do itSell it yourself
Take full control of how buyers see your home on Zillow by listing For Sale by Owner (FSBO).
List your homeWhat's special
Zillow last checked:
Listing updated:
Michelle R Blackburn 859-707-5955,
RE/MAX Creative, Winchester
Alyssa Ryan, 270324
Marshall Lane Real Estate - Lexington
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 3
Primary bedroom
- Level: Second
Bedroom 1
- Level: First
Bedroom 2
- Level: Second
Bedroom 3
- Level: Second
Bedroom 4
- Level: Second
Bathroom 1
- Level: First
Bathroom 2
- Level: Second
Bathroom 3
- Level: Third
Dining room
- Level: First
Foyer
- Level: First
Foyer
- Level: Second
Kitchen
- Level: First
Living room
- Level: First
Other
- Description: Finished attic could be bedroom or recreation room
- Level: Third
Heating
- Forced Air, Natural Gas
Cooling
- Central Air, Ceiling Fan(s), Electric
Appliances
- Included: Dryer, Dishwasher, Refrigerator, Washer, Range
- Laundry: Electric Dryer Hookup, Main Level, Washer Hookup
Features
- Entrance Foyer, Eat-in Kitchen, Walk-In Closet(s), Ceiling Fan(s)
- Flooring: Carpet, Hardwood, Vinyl
- Doors: Storm Door(s)
- Windows: Insulated Windows, Skylight(s), Blinds, Screens
- Basement: Full,Sump Pump,Unfinished,Walk-Out Access
- Number of fireplaces: 4
- Fireplace features: Dining Room, Gas Log, Living Room, Master Bedroom
Interior area
- Total structure area: 3,310
- Total interior livable area: 3,310 sqft
- Finished area above ground: 3,310
- Finished area below ground: 0
Property
Parking
- Total spaces: 2
- Parking features: Basement, Driveway, Garage Door Opener, Garage Faces Side
- Garage spaces: 2
- Has uncovered spaces: Yes
Features
- Levels: Two
- Exterior features: Other
- Fencing: Wood
Lot
- Size: 0.27 Acres
- Features: Landscaped, Many Trees
Details
- Additional structures: Shed(s)
- Parcel number: 054202100900
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Stone
- Roof: Dimensional Style,Shingle
Condition
- New construction: No
- Year built: 1893
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected
Community & HOA
Community
- Subdivision: Thomson Addition
HOA
- Has HOA: No
Location
- Region: Winchester
Financial & listing details
- Price per square foot: $112/sqft
- Tax assessed value: $209,000
- Annual tax amount: $1,537
- Date on market: 4/24/2026
Price history
| Date | Event | Price |
|---|---|---|
| 9/4/2026 | Sold | $370,000-1.3%$112/sqft |
Source: | ||
| 8/18/2026 | Pending sale | $375,000$113/sqft |
Source: | ||
| 8/5/2026 | Contingent | $375,000$113/sqft |
Source: | ||
| 6/24/2026 | Price change | $375,000-2.6%$113/sqft |
Source: | ||
| 6/10/2026 | Price change | $385,000-2.5%$116/sqft |
Source: | ||
| 5/14/2026 | Price change | $395,000-4.8%$119/sqft |
Source: | ||
| 4/24/2026 | Listed for sale | $415,000+299%$125/sqft |
Source: | ||
| 8/31/1998 | Sold | $104,000$31/sqft |
Source: | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $1,537 +30.4% | $209,000 +27.3% |
| 2024 | $1,179 -27.1% | $164,200 |
| 2023 | $1,617 | $164,200 |
| 2022 | $1,617 +0.3% | $164,200 |
| 2021 | $1,613 -0.2% | $164,200 |
| 2020 | $1,616 +574.1% | $164,200 |
| 2019 | $240 | $164,200 |
| 2018 | $240 | $164,200 |
| 2017 | $240 | $164,200 |
| 2016 | $240 | $164,200 |
| 2015 | $240 | $164,200 |
| 2013 | $240 | $164,200 |
| 2011 | -- | $164,200 |
| 2010 | -- | $164,200 |
Neighborhood: 40391
Nearby homes
- $340,4003 bd2 ba2.2k sqft3 Moundale Ave, Winchester, KY 40391Off Market
- $184,9003 bd1 ba1.6k sqft376 S Main St, Winchester, KY 40391Off Market

- $192,300-- bd-- ba1.6k sqft381 S Main St, Winchester, KY 40391Off Market

- $199,5002 bd1 ba972 sqft374 S Main St, Winchester, KY 40391Sold

- $228,5004 bd2 ba1.8k sqft394 S Main St, Winchester, KY 40391Sold
- $221,2003 bd2 ba1.4k sqft366 S Main St, Winchester, KY 40391Off Market
- $190,3003 bd1 ba1.3k sqft387 S Main St, Winchester, KY 40391Off Market
- $185,7003 bd1 ba1k sqft406 S Main St, Winchester, KY 40391Off Market
Nearby schools
GreatSchools rating
- 5/10Shearer Elementary SchoolGrades: K-4Distance: 0.7 mi
- 5/10Robert D Campbell Junior High SchoolGrades: 7-8Distance: 0.7 mi
- 5/10George Rogers Clark High SchoolGrades: 9-12Distance: 2.4 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.
Sell for more on Zillow
Sell for more on Zillow
- Kentucky
- Clark County
- Winchester
- 40391
- 382 S Main St