USAKYWinchesterThomson Addition382 S Main St

382 S Main St, Winchester, KY

Name: 382 S Main St, For Sale in Winchester - eXp Realty
Brand: RE/MAX Creative, Winchester
SKU: 26008931
Price: 375000 USD

House

For Sale

Listed price in listed location currency (USD).

$375,000

432

MLS® 26008931

Key Facts
Description
Rooms
Map

Key Facts

Type Single Family Residence

Levels Residential

Size 3310 sqft

Garage Yes

Taxes

Days Active 78

Lot Size 0.27 Acres

Approx. Age 1893

Avg. Price Per Sqft $113

MLS® Number 26008931

Property Address: 382 S Main St, Winchester, KY, 40391-2466

Average square foot calculated using Size range provided by listing agent.

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.

MLS® Number26008931

Laundry LevelMain

Central VacNo

FireplaceYes

Acreage

Exterior

GarageYes

Approx. Age1893

BasementFull, Sump Pump, Unfinished, Walk-Out Access

DrivewayBasement, Driveway, Garage Door Opener, Garage Faces Side

Garage Spaces

HeatForced Air, Natural Gas

A/CCentral Air, Ceiling Fan(s), Electric

Extras

Price History

-End Date

Not Sold YetSold Price

For Sale

Apr 23, 2026List Date

$375,000List Price

Commute

Commute

Starting Address

Destination Address

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