382 S Main Street, Winchester, KY 40391
Local realty services provided by:Better Homes and Gardens Real Estate Fern Leaf Group
382 S Main Street,Winchester, KY 40391
$370,000
- 4 Beds
- 3 Baths
- - sq. ft.
- Single family
- Sold
Listed by: michelle r blackburn
Office: re/max creative, winchester
MLS#:26008931
Source:KY_LBAR
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Price summary
- Price:$370,000
About this home
Built in 1893, this beautifully maintained home is filled with the charm and craftsmanship that's hard to find today, along with the modern updates buyers appreciate. Situated on a corner lot just minutes from historic downtown Winchester, you'll love the walkable location with South Main Grocery & Grill, a local favorite known for its country ham sandwiches and home-cooked meals, right across the street. The Clark County Public Library, College Park, and downtown Winchester's shops, restaurants, and local events are all just a short walk away. Inside, you'll find over 3,300 square feet featuring four bedrooms, three full baths, soaring ceilings, gorgeous hardwood floors, four fireplaces, beautiful original woodwork, and an updated kitchen that complements the home's historic character. Multiple living spaces provide plenty of room for entertaining, working from home, hosting guests, or simply spreading out, plus the convenience of a basement-entry garage. Enjoy your morning coffee or unwind in the evening from the inviting front porch, the perfect spot for a porch swing and visiting with neighbors. Out back, you'll appreciate the screened-in porch overlooking the secluded-feeling backyard, an ideal space for relaxing, grilling, or enjoying a quiet evening outdoors. Homes like this don't come along often. Rich in history, full of character, and ideally located near the heart of downtown, this home offers the perfect mixture of classic architecture, modern updates, and everyday convenience. Enjoy the charm of small-town living while still being an easy commute to Lexington for work, shopping, dining, and entertainment. If you've been dreaming of owning a home with historic charm, modern comforts, and a location that truly lets you enjoy the best of Winchester, this is one you won't want to miss....
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Home facts
- Year built:1893
- Subdivision & Development:Thomson Addition
- Listing ID #:26008931
- Added:137 day(s) ago
- Updated:September 08, 2026 at 05:46 PM
Rooms and interior
- Bedrooms:4
- Total bathrooms:3
- Full bathrooms:3
- Rooms Total:14
- Flooring:Carpet, Hardwood, Vinyl
- Basement:Yes
- Basement Description:Full, Unfinished
Heating and cooling
- Cooling:Electric
- Heating:Forced Air, Natural Gas
- Central air:Yes
Structure and exterior
- Year built:1893
- Architectural Style:Colonial
- Construction Materials:Vinyl Siding
Schools
- High school:GRC
- Middle school:Robert Campbell
- Elementary school:Shearer
Utilities
- Water:Public
- Sewer:Public Sewer
Finances and disclosures
- Price:$370,000
Features and amenities
- Laundry features:Electric Dryer Hookup, Main Level, Washer Hookup
- Amenities:Blinds, Ceiling Fan(s), Insulated Windows, Screens, Skylight(s)
Parking
- Parking description:Basement, Driveway, Garage Door Opener, Garage Faces Side
- Garage:Yes
- Garage spaces:2
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