# 382 S Main Street, Winchester, KY 40391

> **TL;DR:** 4bd/3ba single family, $395,000 ($119/sqft), built 1893, 3,310 sqft.
> Fireplace, Hardwood, A/C. Est. $1,712/mo. Listed 39 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $395,000 |
| Price/sqft | $119 |
| Bedrooms | 4 |
| Bathrooms | 3 full |
| Square Feet | 3,310 |
| Year Built | 1893 |
| Lot Size | 11,761 sqft (0.27 acres) |
| Stories | 2 |
| Property Type | Single Family (Single Family Residence) |
| Status | For Sale |
| Days on Market | 39 |

## Why This Home Stands Out

- **Hardwood Floors** - Throughout the home

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Mortgage (20% down, 6.5%) | $1,712 |
| **Total** | **$1,712** |

## Nearby Schools

- **Elementary:** Shearer
- **Middle:** Robert Campbell
- **High:** GRC

## Key Amenities

- Fireplace
- Hardwood
- A/C

## Property Highlights

- Built in 1893
- 0.27 acre lot
- 2 stories
- Fireplace

## Description

### Agent Description
Spacious and full of character, this unique 4 bedroom, 3 bath home sits on a corner lot on South Main right across from the iconic South Main Grocery. Inside, you are welcomed by a two story foyer and a layout that offers flexibility with a living room, main level bedroom, full bath, and a dining room that could also function as an office with double doors. The kitchen has space for eat in dining and connects to the laundry room, with access to the screened in porch, private hot tub area, and fenced backyard. A second staircase in the rear adds to the home's charm and functionality. Upstairs features a sitting area, the primary bedroom, and additional bedrooms with access to a shared full bath complete with a clawfoot tub. The finished attic or loft offers great bonus space that could be used as a fourth bedroom, rec room, or guest area and includes another full bath with a jacuzzi tub, along with unfinished attic space for additional storage. The basement level provides a large unfinished area for storage and includes an attached garage. Outside, you will find a covered side porch, a spacious side yard, a fenced backyard, and a storage shed. There is plenty of parking with a front parking pad and an extended side driveway. The home features a mix of flooring throughout and is filled with character including original doors, knobs, mantels, and four working fireplaces.

## Location

- **Address:** 382 S Main Street, Winchester, KY 40391
- **County:** Clark
- **Neighborhood:** Thomson Addition
- **Coordinates:** 37.984389, -84.181842
- **Google Maps:** https://www.google.com/maps?q=37.984389,-84.181842

## Listing Agent

- **Name:** Michelle R Blackburn
- **Brokerage:** RE/MAX Creative, Winchester
- **Phone:** 8597075955
- **Email:** michelle@michelleblackburn.com

## Primary Photo

![382 S Main Street - Primary Photo](http://lh.rdcpix.com/726b127a847539237cd925466e267412l-f2471157873r.jpg)

*60 total photos available on [listing page](https://www.propertysimple.com/listing/382-s-main-street-winchester-ky-40391-26008931)*

---

**MLS#:** 26008931 | **Updated:** 2026-06-18
**Source:** listhub

*Copyright © 2026 ImagineMLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.*

[View on PropertySimple](https://www.propertysimple.com/listing/382-s-main-street-winchester-ky-40391-26008931)

---

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