# 221 S Highland Street, Winchester, KY 40391

> **TL;DR:** 5bd/3ba residential multi family, $239,000 ($79/sqft), built 1930, 3,007 sqft.
> A/C. Est. $1,279/mo. Listed 3 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $239,000 |
| Price/sqft | $79 |
| Bedrooms | 5 |
| Bathrooms | 3 full |
| Square Feet | 3,007 |
| Year Built | 1930 |
| Lot Size | 6,970 sqft (0.16 acres) |
| Stories | 2 |
| Property Type | Residential Multi Family (Other) |
| Status | For Sale |
| Days on Market | 3 |

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $1,209 |
| Estimated Insurance | $70 |
| **Total** | **$1,279** |

## Nearby Schools

- **High:** GRC

## Key Amenities

- A/C

## Property Highlights

- Built in 1930
- 0.16 acre lot
- 2 stories
- 5 parking spaces

## Description

### Agent Description
Excellent investment opportunity!!! A triplex near downtown Winchester. Close to everything. The main level features a unit with 2 bedrooms, 1 full bath, 2 living areas, a large eat-in kitchen and a laundry room. The upstairs unit features 2 bedrooms, 1 full bath, a living room, and an eat-in kitchen. The lower level features a 1 bedroom, 1 full bathroom, a large living room and an eat-in kitchen. The main level unit rents for $1299 per month. The upper unit rents for $895 per month. When the lower level is rented it rents for $799 per month. You will find plenty of parking in the back. There is a carport and storage building that also goes with this property.

## Location

- **Address:** 221 S Highland Street, Winchester, KY 40391
- **County:** Clark
- **Neighborhood:** Downtown
- **Coordinates:** 37.989228, -84.176817
- **Google Maps:** https://www.google.com/maps?q=37.989228,-84.176817

## Listing Agent

- **Name:** Libby Vanmeter
- **Brokerage:** Marshall Lane Real Estate - Lexington
- **Phone:** 8597714811

## Primary Photo

![221 S Highland Street - Primary Photo](http://lh.rdcpix.com/741b4dd45bbb94e088322a52402f9fadl-f1151513709r.jpg)

*39 total photos available on [listing page](https://www.propertysimple.ai/listing/221-s-highland-street-winchester-ky-40391-26015897)*

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**MLS#:** 26015897 | **Updated:** 2026-08-01
**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.ai/listing/221-s-highland-street-winchester-ky-40391-26015897)

---

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  "description": "Excellent investment opportunity!!! A triplex near downtown Winchester. Close to everything. The main level features a unit with 2 bedrooms, 1 full bath, 2 living areas, a large eat-in kitchen and a laundry room. The upstairs unit features 2 bedrooms, 1 full bath, a living room, and an eat-in kitchen. The lower level features a 1 bedroom, 1 full bathroom, a large living room and an eat-in kitchen. The main level unit rents for $1299 per month. The upper unit rents for $895 per month. When the lo",
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