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    1 home
      1 home available
      382 S Main Street, Winchester, KY 40391
      NEW 4 days ago
      382 S Main Street, Winchester, KY 40391
      $415,000
      4beds
      3bath
      3,310sqft
      0.27acres
      House for Sale

      382 S Main Street, Winchester, KY 40391

      Listing by: RE/MAX Creative, Winchester
      1 - 1 of 1 results
      © 2026 Imagine MLS
      Display of MLS Data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals.
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      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      382 S Main Street, Winchester, KY 40391
      NEW 4 days ago
      $415,000
      4beds
      3full,half bath
      3,310sqft
      0.27acres

      382 S Main Street, Winchester, KY 40391

      House for Sale by Michelle R BlackburnRE/MAX Creative, Winchester.

      Data checked -. Listing last updated 3 days ago.
      1. Overview
      2. Details
      3. More 

      Spacious and full of character, this unique 4 bedroom, 3 bath home sits on a corner lot on South Main right across from the iconic South Main Grocery. Inside, you are welcomed by a two story foyer and a layout that offers flexibility with a living room, main level bedroom, full bath, and a dining room that could also function as an office with double doors. The kitchen has space for eat in dining and connects to the laundry room, with access to the screened in porch, private hot tub area, and fenced backyard. A second staircase in the rear adds to the home's charm and functionality. Upstairs features a sitting area, the primary bedroom, and additional bedrooms with access to a shared full bath complete with a clawfoot tub. The finished attic or loft offers great bonus space that could be used as a fourth bedroom, rec room, or guest area and includes another full bath with a jacuzzi tub, along with unfinished attic space for additional storage. The basement level provides a large unfinished area for storage and includes an attached garage. Outside, you will find a covered side porch, a spacious side yard, a fenced backyard, and a storage shed. There is plenty of parking with a front parking pad and an extended side driveway. The home features a mix of flooring throughout and is filled with character including original doors, knobs, mantels, and four working fireplaces.

      Details
        Property type
      Residential
        Year built
      1893
        Heating
      Forced Air, Natural Gas
        Cooling
      Central Air, Ceiling Fan(s), Electric
        Garage
      Yes (2 space)
        Parking spots
      -
      26008931
      MLS ID
      Active
      Status
      04-24-2026
      On market date
        Laundry features
      Electric Dryer Hookup, Main Level, Washer Hookup
        Fireplace
      Yes
        Architectural Style
      Colonial
        Basement
      Full, Sump Pump, Unfinished, Walk-Out Access
        View
      Interior features
      Entrance Foyer, Eat-in Kitchen, Walk-In Closet(s), Ceiling Fan(s)
      Exterior features
      Other
      Lot features
      Landscaped, Many Trees
      Appliances included
      Dryer, Dishwasher, Refrigerator, Washer, Range
      Construction materials
      Vinyl Siding
      Flooring
      Carpet, Hardwood, Vinyl
      Monthly taxes
      -
      Yearly taxes
      -
      School district
      Clark County - 7
      Schools
      Shearer, Robert Campbell, GRC
      Senior community
      No
      Open Houses
      In-Person
      No upcoming in-person open houses
      Virtual
      No upcoming virtual open houses
      Contact Agent
      Michelle R Blackburn
      Michelle R Blackburn
      REALTOR® Salesperson, RE/MAX Creative, Winchester
       
       
      Location
      From Lexington, I64 East to Winchester Exit 96, right on Maple Expressway, left on Lexington Ave by Speedway, right on Main Street. House is on the right on corner of Main St. and Moundale. Directly across from South Main Grocery
      For Sale Nearby
      No nearby homes are For Sale Nearby.
      Recently Sold
      No nearby homes have been Recently Sold.
      382 S Main Street, Winchester, KY 40391, is a 4 bedroom, 3 bathroom, 3310 sqft. Single Family Residence built in 1893. This property is currently available for sale and was listed on Imagine Your Home on 4-24-2026. The MLS# for this Single Family Residence is MLS# 26008931.
      Display of MLS Data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals.
      Copyright ©2026