KY
Clark
Winchester
40391
382 S Main Street
382 S Main Street, Winchester, KY 40391
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Listing Type
Single Family
Listing Status
Active
60
$375,000

Home Details for 382 S Main Street

Price
$375,000
Type
Residential
Bedrooms
4
Total Bathrooms
3
Full Bathrooms
3
Square feet
3310
Year built
1893
Lot size acres
0.27
County
Clark
Total rooms
14
Garage
2
Basement
Full, Sump Pump, Unfinished, Walk-Out Access
Days on site
92
MLS Listing#
26008931
Property Description

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.

Property Features
  • House Interior
    • Entrance Foyer
    • Eat-in Kitchen
    • Walk-In Closet(s)
    • Ceiling Fan(s)
  • Utilities
    • Electricity Connected
    • Natural Gas Connected
    • Sewer Connected
    • Water Connected
  • Parking
    • Basement
    • Driveway
    • Garage Door Opener
    • Garage Faces Side
  • Basement
    • Full
    • Sump Pump
    • Unfinished
    • Walk-Out Access
  • Cooling Information
    • Central Air
    • Ceiling Fan(s)
    • Electric
  • Fire Place
    • Dining Room
    • Gas Log
    • Living Room
  • Heating Information
    • Forced Air
    • Natural Gas
  • Water Features
    • Public
School Information
School Information for 382 S Main Street, Winchester, KY 40391
Elementary School
Shearer
Middle School
Robert Campbell
High School
GRC
Listing Courtesy: RE/MAX Creative, Winchester - 859-422-2000
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Last Updated: 2026-07-20 11:33:06
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EXIT REALTY CRUTCHER
502A Saffell St. , Lawrenceburg, KY 40342
John Rennels
License #: 75712
Sales Representative
Office
502 839 9822
Agent
502 598 8378
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