382 S Main Street, Winchester, KY 40391 (MLS# 26008931)

382 S Main Street, Winchester, KY 40391

$375,000

Side porch *porch swing does not convey*

finished attic - could be used as a bonus room or 4th bedroom

Property Type: Residential Bedrooms: 4 Baths: 3 Square Footage: 3,310 Lot Size (sq. ft.): 11,761 Status: Active

Current Price: $375,000 List Date: 4/24/2026 Last Modified: 7/27/2026

Overview

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 o ... (Read more)

Listing Details MLS# 26008931

Listing Information

Comp Sale YN: No
Property Sub Type: Single Family Residence

Status Change Information

Price Change Timestamp: 2026-06-24T00:16:50Z
Status Change Timestamp: 2026-04-23

Address

County: Clark
Street Number: 382
Street Direction Prefix: S
Street Name: Main
Street Suffix: Street
State: KY
Zip Code: 40391
Zip +4: 2466
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
Parcel Number: 054-2021-009-00

Contract

Original List Price: 415000
Start Showing Date: 2026-04-23
Listing Contract Date: 2026-04-23
Listing Agreement: Exclusive Right To Sell
Occupant Type: Vacant
Office Exclusive YN: No
List Price/SqFt: 113.29

Tax Legal

MLS Area Major: 007 - Clark County
Subdivision Name: Thomson Addition
High School District: Clark County - 7

Interior

Bedrooms Total: 4
Bathrooms Total: 3
Bathrooms Full: 3
Above Grade Finished Area: 3310
Non-Compliant Total SqFt: 307
Living Area: 3310
Living Area Source: Appraiser
Basement YN: Yes
Fireplace YN: Yes
Fireplaces Total: 4
Bathrooms Half: 0
Below Grade Finished Area: 0
Above Grade Unfinished Area: 0
Below Grade Unfinished Area: 0

More Information

Parking Information

Garage YN: Yes
Garage Spaces: 2
Carport YN: No

Building

Year Built: 1893
Accessibility Features YN: No

Lot

Lot Size Source: Public Records
Lot Size Acres: 0.27
Lot Size Square Feet: 11761.2
Pool Private YN: No
Waterfront YN: No
Water Body Access YN: No
Horse YN: No

Utilities

Cooling YN: Yes
Heating YN: Yes
Electricity Connected: Yes
Natural Gas Connected: Yes
Sewer Connected: Yes
Water Connected: Yes

Remarks

Public Remarks: 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.

Amenity Fee Details

Amenity Fee YN: No

Showing Information

Showing Instructions: Alarm should be disarmed for all scheduled showings, but if for any reason it is set, the code is 1520.

Room Types

Bathroom 1 Level: First
Bathroom 2 Level: Second
Bathroom 3 Level: Third
Bedroom 1 Level: First
Bedroom 2 Level: Second
Bedroom 3 Level: Second
Bedroom 4 Level: Second
Dining Room Level: First
Foyer Level: Second
Kitchen Level: First
Living Room Level: First
Other Level: Third
Primary Bedroom Level: Second
Bathroom 1: Yes
Bathroom 2: Yes
Bathroom 3: Yes
Bedroom 1: Yes
Bedroom 2: Yes
Bedroom 3: Yes
Bedroom 4: Yes
Dining Room: Yes
Foyer: Yes
Kitchen: Yes
Living Room: Yes
Other: Yes
Primary Bedroom: Yes
Utility Room: Yes

Currently Not Used

List Price/Acre: 1388888.89

Tax & Legal

Elementary School: Shearer
Middle Or Junior School: Robert Campbell
High School: GRC
Tax Rate: 0.123

Association/Community

Association YN: No

Appliances

Dishwasher: Yes
Dryer: Yes
Range: Yes
Refrigerator: Yes
Washer: Yes

Architectural Style

Colonial: Yes

Attic Features

Finished: Yes
Permanent Stairs: Yes
Walk-In Attic: Yes

Basement

Full: Yes
Sump Pump: Yes
Unfinished: Yes
Walk-Out Access: Yes

Construction Materials

Vinyl Siding: Yes

Cooling

Ceiling Fan(s): Yes
Central Air: Yes
Electric: Yes

Exterior Features

Hot Tub: Yes
Storm Door(s): Yes
Other: Yes

Fencing

Wood: Yes

Fireplace Features

Dining Room: Yes
Gas Log: Yes
Living Room: Yes
Primary Bedroom: Yes

Flooring

Carpet: Yes
Hardwood: Yes
Vinyl: Yes

Foundation Details

Stone: Yes

Heating

Forced Air: Yes
Natural Gas: Yes

Interior Features

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

Laundry Features

Electric Dryer Hookup: Yes
Main Level: Yes
Washer Hookup: Yes

Levels

Two: Yes

Lot Features

Landscaped: Yes
Many Trees: Yes

Other Structures

Shed(s): Yes

Parking Features

Basement: Yes
Driveway: Yes
Garage Door Opener: Yes
Garage Faces Side: Yes

Patio And Porch Details

Front Porch: Yes
Screened Porch: Yes
Side Porch: Yes

Patio And Porch Features

Porch: Yes
Other: Yes

Possession

Close Of Escrow: Yes
Close Plus 3 Days: Yes

Roof

Dimensional Style: Yes
Shingle: Yes

Sewer

Public Sewer: Yes

Structure Type

House: Yes

Water Heater

Electric: Yes

Water Source

Public: Yes

Window Features

Blinds: Yes
Insulated Windows: Yes
Screens: Yes
Skylight(s): Yes

Showing Requirements

Call Listing Agent: Yes
Show Anytime: Yes
Showing Service: Yes

Property Features

Utilities: Electricity Connected; Natural Gas Connected; Sewer Connected; Water Connected; Electricity Connected; Natural Gas Connected; Sewer Connected; Water Connected Appliances: Dishwasher; Dryer; Range; Refrigerator; Washer Architectural Style: Colonial Attic Features: Finished; Permanent Stairs; Walk-In Attic Basement: Full; Sump Pump; Unfinished; Walk-Out Access Construction Materials: Vinyl Siding Cooling: Ceiling Fan(s); Central Air; Electric Exterior Features: Hot Tub; Storm Door(s); Other Fencing: Wood Fireplace Features: Dining Room; Gas Log; Living Room; Primary Bedroom Flooring: Carpet; Hardwood; Vinyl Foundation Details: Stone Heating: Forced Air; Natural Gas Interior Features: Ceiling Fan(s); Eat-in Kitchen; Entrance Foyer; Walk-In Closet(s) Laundry Features: Electric Dryer Hookup; Main Level; Washer Hookup Levels: Two Lot Features: Landscaped; Many Trees Other Structures: Shed(s) Parking Features: Basement; Driveway; Garage Door Opener; Garage Faces Side Patio And Porch Details: Front Porch; Screened Porch; Side Porch Patio And Porch Features: Porch; Other Possession: Close Of Escrow; Close Plus 3 Days Roof: Dimensional Style; Shingle Sewer: Public Sewer Structure Type: House Water Heater: Electric Water Source: Public Window Features: Blinds; Insulated Windows; Screens; Skylight(s) Showing Requirements: Call Listing Agent; Show Anytime; Showing Service Room Types: Bathroom 1; Bathroom 2; Bathroom 3; Bedroom 1; Bedroom 2; Bedroom 3; Bedroom 4; Dining Room; Foyer; Kitchen; Living Room; Other; Primary Bedroom; Utility Room

Room Information

Room Name	Level	Remarks
Foyer	First
Living Room	First
Dining Room	First
Bedroom 1	First
Kitchen	First
Bathroom 1	First
Foyer	Second
Primary Bedroom	Second
Bedroom 2	Second
Bedroom 3	Second
Bedroom 4	Second
Bathroom 2	Second
Other	Third	Finished attic could be bedroom or recreation room
Bathroom 3	Third

Documents

Sellers Disclosure Of Property Condition ›

Lead Based Paint Disclosure ›

Utility Information ›

Listing Office: RE/MAX Creative, Winchester

Last Updated: July - 27 - 2026

Information deemed reliable but not guaranteed.