363 S Main Street Winchester, KY $ 250,000
363 S Main Street
$ 250,000
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363 S Main Street

Winchester, KY, 40391
$ 250,000
Bedrooms3 Baths2.0 Sq 2,142

Monthly Estimate*

$ 1,539

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Single Family Home for sale in Winchester, KY

for $250,000 with 3 bedrooms and 2 full baths. This 2,142 square foot home was built in 1940 on a lot size of 0.49.

Welcome to 363 South Main Street in the heart of downtown Winchester, KY—this spacious 3-bedroom, 2-bath home offers 2,142 square feet of character, updates, and convenience. Ideally located close to all local amenities and just 5 minutes from I-64, you'll enjoy easy access to shopping, dining, and commuting. The home features beautiful hardwood floors and an updated kitchen with plenty of cabinet space, perfect for everyday living and entertaining. Recent improvements include a new roof, soffit, and gutters, along with an updated HVAC system, fresh exterior paint, professional pressure washing, and refreshed landscaping—making this property truly move-in ready. A versatile loft space provides additional storage or future potential, while the covered front porch, back deck, and fenced backyard create the perfect setup for relaxing or hosting guests. This is a rare opportunity to own a well-updated home in a prime downtown location.

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Single Family Active

Price

$ 250,000

Bedrooms

3

Full Bath

2

Property Type

Single Family

Taxes

$ 0

Style

Single Family Residence

Lot Size

0.49

Year Built

1940

Town/City

Winchester

County/Region

Clark

MLS | Web ID

26009123

Features
Interior
Interior Amenities Ceiling Fan(s) Eat-in Kitchen Primary Downstairs Walk-In Closet(s)
Basement Crawl Space
Flooring Carpet Hardwood Tile
Basement (Y/N) N
Air Conditioning Y/N Y
Heating Y/N Y
Window Features Blinds Screens
Fireplace Y/N N
Above Grade Finished Area 2142.0
Half Baths 0
Total Bedrooms 3
Below Grade Finished Area 0.0
Total Baths 2
Heating-Natural Gas True
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General
Sewer Public Sewer
Heating Electric Natural Gas
Cooling Ceiling Fan(s) Electric
Utilities Electricity Connected Sewer Connected Water Connected
Possession Negotiable
Roof Shingle
Appliances Cooktop Oven Refrigerator
Patio/Porch Features Deck Porch
Construction Materials Vinyl Siding
Year Built 1940
View Neighborhood
Levels One
Property Subtype Single Family Residence
Parcel Number 054-4002-046-00
County Clark
New Construction N
Property Type Residential
HOA N
Attached Garage N
Subdivision Name Thomson Addition
Garage Y/N N
Other Structures Shed(s)
Total Rooms 9
Full Baths 2
Status Active
Directions From Exit 96 - Turn left onto Paris Rd. towards Winchester. After 1.6 Miles turn left onto W Lexington Avenue. Then turn right onto S Main Street and the property will be on the left after half a mil
High School GRC
City Winchester
High School District Clark County - 7
MLS Area 007 - Clark County
Lot Size Units Acres
Lot Size Square Feet 21344.4
Carport Y/N N
Elementary School Shearer
Land Lease Y/N N
Home Warranty Y/N N
Middle/Junior High School Robert Campbell
MLS Area Minor 007 - Clark County
Lease Considered Y/N N
Rent Control Y/N N
Standard Status Active
Senior Community None
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Exterior
Fencing Wood
Parking Features Driveway Off Street
Water Source Public
Lot Size Area 0.49
Foundation Details Concrete Perimeter Stone
Building Area Total 2142.0
Lot Size Acres 0.49
Lot Size Source Public Records
Waterfront Y/N N
Door Features Storm Door(s)
Crops Included Y/N N
Horse Y/N N
Irrigation Water Rights Y/N N
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Internal Only
Street Number 1 363
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* Excluded Features
List By
Homeland Real Estate Inc

Broker

zack@kyhomeland.com

Email

Affordability Calculator

$1,539
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Monthly Principal & Interest
$1,539
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Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3289857 Elementary School
3291684 Middle School
GRC High School High School
Pricing History
DatePricePrice ChangeDescription
4/26/2026$250,000 Listed Price

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363 S Main Street, Winchester, KY, 40391 is a Single Family Home for sale at $250,000 with 2,142 sqft and a lot size of 0.49. 363 S Main Street has 3 bedrooms, 2.0 baths, and was built in 1940. The property's zip code is 40391 which is in Winchester, KY