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
$375,000
- 4 Beds
- 3 Baths
- 3,310 sq. ft.
- Single family
- Active
Listed by: michelle r blackburn
Office: re/max creative, winchester
MLS#:26008931
Source:KY_LBAR
Price summary
- Price:$375,000
- Price per sq. ft.:$113.29
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....
Contact an agent
Home facts
- Year built:1893
- Listing ID #:26008931
- Added:79 day(s) ago
- Updated:July 12, 2026 at 03:35 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
- Living area:3,310 sq. ft.
Heating and cooling
- Cooling:Electric
- Heating:Forced Air, Natural Gas
- Central air:Yes
Structure and exterior
- Year built:1893
- Building area:3,310 sq. ft.
- Lot area:0.27 Acres
- 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:$375,000
- Price per sq. ft.:$113.29
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
New listings near 382 S Main Street
- New
$749,900Active3 beds 3 baths2,735 sq. ft.2180 Big Stoner Road, Winchester, KY 40391
MLS# 26017698Listed by: INDIGO & CO - New
$319,900Active5 beds 2 baths2,082 sq. ft.128 Cherokee Drive, Winchester, KY 40391
MLS# 26017629Listed by: OAK & ACRE
$350,000Pending4 beds 3 baths2,591 sq. ft.411 Skylark Drive, Winchester, KY 40391
MLS# 26017601Listed by: KELLER WILLIAMS COMMONWEALTH- New
$225,000Active3 beds 4 baths1,892 sq. ft.128 Abbeywood Court, Winchester, KY 40391
MLS# 26017061Listed by: ERA SELECT REAL ESTATE - New
$795,000Active3 beds 3 baths3,336 sq. ft.6356 Van Meter Road, Winchester, KY 40391
MLS# 26017477Listed by: FREEDOM REALTY & PROPERTY MANAGEMENT - New
$229,900Active3 beds 2 baths1,200 sq. ft.491 Hidden Hills Way, Winchester, KY 40391
MLS# 26017144Listed by: HOMEFIRST REAL ESTATE - New
$326,000Active48.54 Acres380 Howard Creek Road #380, Winchester, KY 40391
MLS# 26017069Listed by: COLDWELL BANKER MCMAHAN - New
$274,900Active4 beds 3 baths1,377 sq. ft.304 Sandra Drive, Winchester, KY 40391
MLS# 26016975Listed by: THE AGENCY - New
$374,900Active3 beds 2 baths2,269 sq. ft.15 Moundale Avenue, Winchester, KY 40391
MLS# 26016576Listed by: FREEDOM REALTY & PROPERTY MANAGEMENT - Open Sun, 12 to 2pmNew
$415,000Active3 beds 2 baths2,304 sq. ft.215 Delaplain Road, Winchester, KY 40391
MLS# 26016762Listed by: MARSHALL LANE REAL ESTATE - LEXINGTON