Welcome to 363 South Main Street in the heart of Winchester, Kentucky! This charming 3-bedroom, 2-bath home offers the perfect blend of timeless character and modern convenience. Built in 1940, the home exudes classic appeal with thoughtful updates that meet today's lifestyle. With 2,142 square feet of living space, there's plenty of room for a growing family to spread out and feel right at home. You'll love the inviting layout, featuring a cozy loft area ideal for relaxing with a good book or creating a quiet retreat. Located just minutes from local schools, shops, and restaurants, this home provides unbeatable convenience in a welcoming community. Don't miss your chance to tour this beautifully maintained gem--schedule your showing today and see why 363 South Main Street could be your perfect next home!
For sale
Price cut: $16K (5/19)
$259,000
363 S Main St, Winchester, KY 40391
3beds
2,142sqft
Est.:
Single Family Residence
Built in 1940
0.49 Acres Lot
$250,200 Zestimate®
$121/sqft
$-- HOA
What's special
Timeless characterModern convenienceCozy loft area
- 34 days
- on Zillow |
- 1,369 |
- 86 |
Zillow last checked: 7 hours ago
Listing updated: May 19, 2025 at 01:33am
Listed by:
Zachary Otis 606-336-3659,
Homeland Real Estate Inc
Source: Imagine MLS,MLS#: 25009250

Travel times
Tour with a buyer’s agent
Tour with a buyer’s agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Primary bedroom
- Level: 1
Bedroom
- Level: 1
Bedroom
- Level: 1
Dining room
- Level: 1
Other
- Level: 1
Other
- Level: 1
Kitchen
- Level: 1
Living room
- Level: 1
Rec room
- Description: There is a spiral staircase that leads to a small loft. The seller's used it for an art room.
- Level: 1
Utility room
- Level: 1
Heating
- Natural Gas
Cooling
- Electric
Appliances
- Included: Dryer, Washer, Refrigerator, Range, Microwave, Dishwasher
Features
- Dining Area, Attic
- Flooring: Carpet, Tile, Hardwood
- Has basement: No
- Has fireplace: Yes
Interior area
- Total structure area: 2,142
- Total interior livable area: 2,142 sqft
- Finished area above ground: 2,142
- Finished area below ground: 0
Property
Parking
- Parking features: Driveway
Features
- Levels: One
- Patio & porch: Deck, Porch
Lot
- Size: 0.49 Acres
Details
- Parcel number: 054400204600
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Stone
- Roof: Composition,Shingle
Condition
- Year built: 1940
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Electricity Connected, Sewer Connected, Water Connected
Community & HOA
Community
- Subdivision: Thomson Addition
Location
- Region: Winchester
Financial & listing details
- Price per square foot: $121/sqft
- Tax assessed value: $139,500
- Annual tax amount: $1,373
- Date on market: 5/5/2025
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