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Deborah Campbell
REALTOR®
(606) 599-5774
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382 S Main Street, Winchester, KY 40391

$375,000
  • 382 S Main Street, Winchester, KY 40391 Main Photo

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Active
BEDS4 BATHS3 full SQUARE FEET3,310 MLS#26008931
STATUS PROPERTY TYPEResidential - Single Family SUBDIVISIONThomson Addition SCHOOLClark County - 7

Property 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.

382 S Main Street | MLS# 26008931

This single family home located at 382 S Main Street, Winchester, KY 40391 is currently listed for sale with an asking price of $375,000. This property was built in 1893 and has 4 bedrooms and 3 full baths with 3310 sq. ft. S Main Street is located in the Thomson Addition subdivision within the Clark County - 7 school district. Search Thomson Addition real estate on debbie.salliedavidson.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Cooling: Central Air, Ceiling Fan(s), Electric
Fireplaces: 4
Fuel Type: Gas
Garage: 2
Heating: Forced Air, Natural Gas
Home Style: Colonial
Lot Size: 0.27 Acres
Roof Type: Dimensional Style, Shingle
Stories: 2.0
Year Built: 1893

Amenities

Entrance Foyer
Eat-in Kitchen
Walk-In Closet(s)
Ceiling Fan(s)
Other

Feature Descriptions

Appliance Features: Dryer, Dishwasher, Refrigerator, Washer, Range
Attic: Finished, Permanent Stairs, Walk-In Attic
Basement Features: Full, Sump Pump, Unfinished, Walk-Out Access
Days on Site: 85
Exterior: Vinyl Siding
Fireplace Features: Dining Room, Gas Log, Living Room, Primary Bedroom
Flooring: Carpet, Hardwood, Vinyl
Laundry: Electric Dryer Hookup, Main Level, Washer Hookup
Laundry Features: Electric Dryer Hookup, Main Level, Washer Hookup
Lot Dimensions: 0.270 acre(s)
Lot Features: Landscaped, Many Trees
Parcel #: 054-2021-009-00
Parking Notes: Basement, Driveway, Garage Door Opener, Garage Faces Side
Rooms Total: 14
Structures: Shed(s)
Structure Type: House
Utilities: Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected
Window Features: Insulated Windows, Skylight(s), Blinds, Screens

Local Schools

High School: GRC
Middle School: Robert Campbell
Elementary School: Shearer
School District: Clark County - 7

Listed By / Shown By

Listed By

Agency Name: RE/MAX Creative, Winchester

Shown By

Agent Name: Deborah Campbell
Agent Phone: (606) 599-5774
Agency Title: SALLIE DAVIDSON, REALTORS

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Estimated Payment

$ 1,456.51 per month $1,347.13 Principal & Interest $0.00 Property Tax (data not provided by mls) $109.38 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 07/18/2026. The listing information on this page last changed on 07/18/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Sat 07/18/2026 12:01:47 AM EST) or Imagine MLS (last updated Fri 07/17/2026 11:15:25 PM EST). Real estate listings held by brokerage firms other than SALLIE DAVIDSON, REALTORS may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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