382 S Main St, Winchester, KY, 40391
About This Home
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.
Getting Around
Somewhat Walkable
Very Limited Transit
Somewhat BikeableSchools
Construction
Condition
- Year built: 1893
Materials
- Foundation: Stone
- Roof: Dimensional Style,Shingle
- Construction materials: Vinyl Siding
Type & Style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subType: Single Family Residence
Interior
Appliances
- Appliances included: Dryer,Dishwasher,Refrigerator,Washer,Range
- Laundry features: Electric Dryer Hookup,Main Level,Washer Hookup
Basement
- Has basement: Yes
- Basement: Full,Sump Pump,Unfinished,Walk-Out Access
Bathroom1
- Level: First
Bathroom2
- Level: Second
Bathroom3
- Level: Third
Bedroom1
- Level: First
Bedroom2
- Level: Second
Bedroom3
- Level: Second
Bedroom4
- Level: Second
Bedrooms & Bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 3
Dining Room
- Level: First
Features
- Entrance Foyer,Eat-in Kitchen,Walk-In Closet(s),Ceiling Fan(s)
- Door features: Storm Door(s)
- Window features: Insulated Windows,Skylight(s),Blinds,Screens
- Flooring: Carpet,Hardwood,Vinyl
- Number of fireplaces: 4
- Fireplace features: Dining Room,Gas Log,Living Room,Master Bedroom
- Fireplace: Yes
- Finished area below ground: 0
- Finished area above ground: 3,310
Foyer
- Level: First
Foyer
- Level: Second
Heating & Cooling
- Heating features: Forced Air,Natural Gas
- Cooling features: Central Air,Ceiling Fan(s),Electric
Interior Area
- Total structure area: 3,310
- Total interior livable area: 3,310 sqft
Kitchen
- Level: First
Living Room
- Level: First
Master Bedroom
- Level: Second
Other
- Level: Third
Property
Details
- Parcel number: 054202100900
Features
- Levels: Two
- Exterior features: Other
- Fencing: Wood
Lot
- Lot size: 0.27 Acres
- Features: Landscaped,Many Trees
Parking
- Total spaces: 2
- Parking features: Basement,Driveway,Garage Door Opener,Garage Faces Side
- Has garage: Yes
- Attached garage spaces: 2
- Covered spaces: 2
- Has uncovered spaces: Yes
Climate Risk is Financial Risk
Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.
Biggest Threats for This Home
- Lightning
- Strong Wind
- Tornado
- Winter Weather
- Cold Wave
- Hail
- Inland Flooding
- Ice Storm
How This Home’s Risks Compare
FEMA Declared Disasters Across Kentucky Counties
Understanding the Costs
Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.
Estimated Costs Today
| Monthly | Annual | |
|---|---|---|
| Mortgage | $1,896 | $22,752 |
| Home Insurance * | $183 | $2,196 |
| Property Taxes | $299 | $3,588 |
| Electricity | $261 | $3,136 |
| Total | $2,639 | $31,668 |
Income You'd Need if You Spent...
Kentucky FAIR Plan Programs
How Costs Could Change Over Time
Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.
Comparing Against the Market
Price Per Sq Ft
vs Other Active Listings
Avg $/sqft
vs Homes Sold Last Month
Median $/sqft
Current Market Trends
Median Price Per Square Foot
The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.
Historicals for This Listing
Zestimate History ($/sqft)
Price History
| Date | Event | Price |
|---|---|---|
| 2026-08-05 | Contingent | $375,000 |
| 2026-06-24 | Price change | $375,000 |
| 2026-06-10 | Price change | $385,000 |
| 2026-05-14 | Price change | $395,000 |
| 2026-04-24 | Listed for sale | $415,000 |
| 1998-08-31 | Sold | $104,000 |
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