382 S Main Street, Winchester, KY 40391
Thomson Addition · Clark County
Key Facts
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 Information
Property Type
Residential
Sub-Type
Single Family Residence
Structure Type
House
Year Built
1893
Living Area
3,310 sq ft
Lot Size
0.27 acres
Garage Spaces
2
MLS® Listing#
26008931
Property Features
Interior
Exterior
Appliances
Cooling
Heating
Flooring
Fireplace
Basement
Parking
Laundry
Fencing
Lot Features
Construction
Foundation
Roof
Windows
Other Structures
Utilities
Sewer
Water Source
Rooms
- Second
- Second
- First
- Third
- Bathroom 1First
- Bathroom 2Second
- Bathroom 3Third
- Bedroom 1First
- Bedroom 2Second
- Bedroom 3Second
- Bedroom 4Second
- Dining RoomFirst
- KitchenFirst
- Living RoomFirst
Schools
- Elementary:
- Shearer
- Middle:
- Robert Campbell
- High:
- GRC
Financial Details
HOA
None
Parcel Number
054-2021-009-00
Directions
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
Affordability Calculator
$75,000
Estimated monthly payment
$1,996/mo
Principal $300,000 · Est. interest $418,527 over 30 yrs
Neighborhood Market Statistics
How this home compares to active listings in Winchester, KY
- $341,379
- Median Listing Price
- 57
- Median Days on Market
- 2,048
- Median Sq Ft
- $176
- Median Price / Sq Ft
- 116
- Active Listings
- This home’s price is 10% above the area median.
- Its price per sq ft is 36% below the area median.
Market statistics compiled from active EXIT Realty® and MLS listings in Winchester, KY.
Location
Points of Interest in Winchester, KY
Showing the Winchester area map.
Nearby Schools
St Agatha Academy
School · 0.4 mi away
Hannah McClure Elementary School
Elementary · 0.5 mi away
Shearer Elementary School
Elementary · 0.7 mi away
Robert D Campbell Pto
Secondary · 0.7 mi away
Kentucky Tech Clark Co Center
School · 0.7 mi away
Phoenix Academy
School · 0.8 mi away
Fannie Bush Elementary School
Elementary · 1.1 mi away
Victory Heights School
School · 1.4 mi away
Central Elementary School
Elementary · 1.6 mi away
Willis H. Justice Elementary School
Elementary · 1.6 mi away
Conkwright Middle School
School · 1.7 mi away
William G. Conkwright Elementary
Elementary · 1.7 mi away
Calvary Christian Church
School · 1.7 mi away
Flutterby Discovery Center
School · 1.9 mi away
Clark County Area Technology Center
Secondary · 1.9 mi away
Clark County Christian School
Elementary · 2.1 mi away
GRC Cardinals Nest
School · 2.4 mi away
Clark County Public Schools
School · 2.4 mi away
Henry E Baker Intermediate
Secondary · 2.4 mi away
Clark Middle School
School · 2.4 mi away
Commute Calculator
Nearby Homes
Similar Homes Nearby
Similar Home Values
Comparable nearby listings and their asking prices.
| Address | Price | Beds | Baths | Sq Ft |
|---|---|---|---|---|
| 119 Sunset Heights, Winchester, KY | $265,000 | 3 | 1 | 1,324 |
| 20 Jackson Street, Winchester, KY | $270,000 | 3 | 2 | 1,650 |
| 316 Buffalo Trace, Winchester, KY | $272,900 | 3 | 2 | 1,356 |
| 162 French Avenue, Winchester, KY | $273,900 | 4 | 1 | 2,327 |
| 137 Eastridge Drive, Winchester, KY | $274,500 | 3 | 2 | 1,420 |
| 304 Sandra Drive, Winchester, KY | $274,900 | 4 | 3 | 1,377 |
Moving Cost Estimate
EXIT Agents in Winchester
Listing Courtesy: RE/MAX Creative, Winchester - 8594222000
Last Updated: 2026-04-23