382 S Main Street, Winchester, KY 40391

• 4 beds |
• 3 baths |
• 3,310 sqft

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.

Listing Status:

Active

Date Added:

April 24, 2026

Data Last Updated:

July 5, 2026 at 10:41PM

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®)