382 S Main Street, Winchester, KY 40391

• 4 beds |
• 3 baths |
• 3,310 sqft

Property Description

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.

Listing Status:

Active

Date Added:

April 24, 2026

Data Last Updated:

May 21, 2026 at 12:40AM

Listing Office:

RE/MAX Creative, Winchester : 859-422-2000

MLS ID:

26008931

Interior

• General: Entrance FoyerEat-in KitchenWalk-In Closet(s)Ceiling Fan(s)
• Appliances: DryerDishwasherRefrigeratorWasherRange
• Laundry: Electric Dryer HookupMain LevelWasher Hookup
• Basement: FullSump PumpUnfinishedWalk-Out Access
• Flooring: CarpetHardwoodVinyl
• A/C: Central AirCeiling Fan(s)Electric
• Heating: Forced AirNatural Gas
• Fireplace: Dining RoomGas LogLiving RoomPrimary BedroomFireplaceFireplaces: 4

Exterior

• General: OtherShed(s)
• Style: Colonial
• Other Structures: Shed(s)
• Parking: BasementDrivewayGarage Door OpenerGarage Faces Side

Construction

• Roofing: Dimensional StyleShingle
• Windows: Insulated WindowsSkylight(s)BlindsScreens
• General: Vinyl SidingTwoStone

Location

• Originating MLS: Imagine MLS (Bluegrass REALTORS®)
• School District: Clark County - 7
• County: Clark

Lot

• Zoning: 054-2021-009-00
• Fencing: Wood

Utilities

• Utilities: Electricity ConnectedNatural Gas ConnectedSewer ConnectedWater Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Imagine MLS (Bluegrass REALTORS®)