Beautifully updated 3-bedroom, 2-bath home in the heart of Winchester! Brand-new siding and a welcoming front porch set the tone. Inside, you'll find a light-filled living room with a decorative fireplace and cozy reading nook, plus refinished hardwood floors throughout most of the main level. The first-floor bedroom has new carpet and easy access to a fully updated full bath. The remodeled kitchen features modern finishes, a built-in pantry, and opens to the back porch and newly paved driveway—perfect for bringing in groceries. The dining room is bright and spacious with built-in storage.
Upstairs includes a laundry room with closet, utility sink, and attic access for extra storage. You'll also find a bonus room perfect for an office or creative space, and a private primary suite with a walk-in closet and its own full bath. Fresh paint, updated lighting, modernized bathrooms, and a 3-year-old roof add to the appeal. The new gas HVAC (downstairs) adds year-round comfort.
Outside, enjoy a fully fenced backyard, concrete driveway and parking pad, a 13X20 outbuilding with 12-ft ceilings and black metal roof, plus a storage shed. Move-in ready. Call today!
Sold for $244,000
$244,000
252 S Highland St, Winchester, KY 40391
3beds
1,944sqft
Single Family Residence
Built in 1935
6,969 Square Feet Lot
$251,200 Zestimate®
$126/sqft
$1,682 Estimated rent
Home value
$251,200
$196,000 - $324,000
$1,682/mo
Zestimate® history
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List your homeWhat's special
Refinished hardwood floorsModern finishesDecorative fireplaceWelcoming front porchPrivate primary suiteRemodeled kitchenParking pad
Zillow last checked:
Listing updated:
Listed by:
Austina Bruton 859-749-7880,
The Howard Realty Co
Bought with:
Austina Bruton, 269043
The Howard Realty Co
Source: Imagine MLS,MLS#: 25016251
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Primary bedroom
- Level: Second
Bedroom 1
- Level: First
Bedroom 2
- Level: Second
Bathroom 1
- Description: Full Bath
- Level: First
Bathroom 2
- Description: Full Bath
- Level: Second
Dining room
- Level: First
Dining room
- Level: First
Kitchen
- Level: First
Living room
- Level: First
Living room
- Level: First
Utility room
- Level: Second
Heating
- Natural Gas
Cooling
- Electric
Appliances
- Included: Dryer, Disposal, Dishwasher, Refrigerator, Washer, Range
- Laundry: Electric Dryer Hookup, Washer Hookup
Features
- Walk-In Closet(s), Ceiling Fan(s)
- Flooring: Carpet, Hardwood, Laminate, Tile
- Doors: Storm Door(s)
- Windows: Storm Window(s), Blinds, Screens
- Basement: Crawl Space
- Has fireplace: Yes
- Fireplace features: Living Room
Interior area
- Total structure area: 1,944
- Total interior livable area: 1,944 sqft
- Finished area above ground: 1,944
- Finished area below ground: 0
Property
Parking
- Parking features: Driveway
- Has uncovered spaces: Yes
Features
- Levels: One and One Half
- Patio & porch: Patio, Porch
- Fencing: Wood
- Has view: Yes
- View description: Neighborhood
Lot
- Size: 6,969 Square Feet
Details
- Parcel number: 054400101100
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Stone
- Roof: Shingle
Condition
- New construction: No
- Year built: 1935
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Subdivision: Downtown
Location
- Region: Winchester
Financial & listing details
- Price per square foot: $126/sqft
- Tax assessed value: $179,900
- Annual tax amount: $1,799
- Date on market: 7/25/2025
Price history
| Date | Event | Price |
|---|---|---|
| 9/12/2025 | Sold | $244,000-2.4%$126/sqft |
Source:  Imagine MLS #25016251 Report a problem | ||
| 8/12/2025 | Pending sale | $249,900$129/sqft |
Source: Imagine MLS #25016251 Report a problem | ||
| 7/25/2025 | Listed for sale | $249,900+38.9%$129/sqft |
Source: Imagine MLS #25016251 Report a problem | ||
| 3/18/2022 | Sold | $179,900$93/sqft |
Source: Imagine MLS #20124788 Report a problem | ||
| 1/19/2022 | Pending sale | $179,900$93/sqft |
Source: Imagine MLS #20124788 Report a problem | ||
| 1/15/2022 | Listed for sale | $179,900$93/sqft |
Source: Imagine MLS #20124788 Report a problem | ||
| 1/3/2022 | Pending sale | $179,900$93/sqft |
Source: Imagine MLS #20124788 Report a problem | ||
| 1/3/2022 | Listed for sale | $179,900$93/sqft |
Source: Imagine MLS #20124788 Report a problem | ||
| 12/22/2021 | Pending sale | $179,900$93/sqft |
Source: Imagine MLS #20124788 Report a problem | ||
| 12/17/2021 | Listed for sale | $179,900$93/sqft |
Source: Imagine MLS #20124788 Report a problem | ||
| 12/7/2021 | Pending sale | $179,900$93/sqft |
Source: Imagine MLS #20124788 Report a problem | ||
| 11/24/2021 | Listed for sale | $179,900$93/sqft |
Source: Imagine MLS #20124788 Report a problem | ||
| 11/20/2021 | Pending sale | $179,900$93/sqft |
Source: Imagine MLS #20124788 Report a problem | ||
| 11/17/2021 | Listed for sale | $179,900+49.3%$93/sqft |
Source: Imagine MLS #20124788 Report a problem | ||
| 2/4/2016 | Sold | $120,500-2.8%$62/sqft |
Source:  Imagine MLS #1513851 Report a problem | ||
| 12/18/2015 | Pending sale | $124,000$64/sqft |
Source: Rector Hayden REALTORS - Winchester #1513851 Report a problem | ||
| 9/10/2015 | Price change | $124,000-0.8%$64/sqft |
Source: Winchester Office #1513851 Report a problem | ||
| 8/20/2015 | Price change | $125,000-1.6%$64/sqft |
Source: Winchester Office #1513851 Report a problem | ||
| 6/25/2015 | Listed for sale | $127,000+12.7%$65/sqft |
Source: Rector Hayden, Realtors #1513851 Report a problem | ||
| 10/30/2013 | Sold | $112,700-1.1%$58/sqft |
Source: Imagine MLS #1315447 Report a problem | ||
| 8/2/2013 | Price change | $113,900-5%$59/sqft |
Source: ERA Select Real Estate #1315447 Report a problem | ||
| 5/7/2013 | Price change | $119,900-0.8%$62/sqft |
Source: Owner Report a problem | ||
| 5/5/2013 | Listed for sale | $120,900+1.6%$62/sqft |
Source: Owner Report a problem | ||
| 6/24/2009 | Sold | $119,000+14.5%$61/sqft |
Source: Imagine MLS #910333 Report a problem | ||
| 9/18/2006 | Sold | $103,900$53/sqft |
Source: Imagine MLS #633322 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $1,799 +14.1% | $179,900 |
| 2023 | $1,576 | $179,900 +12.4% |
| 2022 | $1,576 +33.1% | $160,000 +32.8% |
| 2021 | $1,184 -0.2% | $120,500 |
| 2020 | $1,186 +574.1% | $120,500 |
| 2019 | $176 | $120,500 |
| 2018 | $176 | $120,500 |
| 2017 | $176 | $120,500 |
| 2016 | $176 | $120,500 +6.9% |
| 2015 | $176 +6.9% | $112,700 -5.3% |
| 2013 | $165 | $119,000 |
| 2011 | -- | $119,000 |
| 2010 | -- | $119,000 |
Find assessor info on the county website
Neighborhood: 40391
Nearby homes
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Nearby schools
GreatSchools rating
- 5/10Shearer Elementary SchoolGrades: K-4Distance: 0.4 mi
- 5/10Robert D Campbell Junior High SchoolGrades: 7-8Distance: 1 mi
- 5/10George Rogers Clark High SchoolGrades: 9-12Distance: 2.7 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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- Kentucky
- Clark County
- Winchester
- 40391
- 252 S Highland St
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