# 221 S Highland Street, Winchester, KY 40391

> **TL;DR:** 5bd/3ba residential multi family, $246,400 ($82/sqft), built 1930, 3,007 sqft.
> A/C. Est. $1,068/mo. Listed 9 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $246,400 |
| Price/sqft | $82 |
| Bedrooms | 5 |
| Bathrooms | 3 full |
| Square Feet | 3,007 |
| Year Built | 1930 |
| Lot Size | 6,970 sqft (0.16 acres) |
| Stories | 1 |
| Property Type | Residential Multi Family (Other) |
| Status | For Sale |
| Days on Market | 9 |

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Mortgage (20% down, 6.5%) | $1,068 |
| **Total** | **$1,068** |

## Nearby Schools

- **High:** GRC

## Key Amenities

- A/C

## Property Highlights

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

## Description

### Agent Description
INVESTOR SPECIAL, You have the opportunity to purchase a fully occupied tri-plex in the heart of Winchester with instant cash flow. Main level unit is a large 2 bed, one bath. Upstairs unit is also a 2 bed, one bath, and lower level is a 1 bed, one bath unit. There is street parking and alley access with parking in the rear. All units have their own exterior entrance. Some utilities are metered together, landlord does cover utility expenses. Please call with any questions, please do not disturb the tenants!

## Location

- **Address:** 221 S Highland Street, Winchester, KY 40391
- **County:** Clark
- **Neighborhood:** Downtown
- **Coordinates:** 37.98926, -84.176987
- **Google Maps:** https://www.google.com/maps?q=37.98926,-84.176987

## Listing Agent

- **Name:** Joshua Lynch
- **Brokerage:** The Brokerage
- **Phone:** 8594286379
- **Email:** josh@thebrokerageky.com

## Primary Photo

![221 S Highland Street - Primary Photo](http://lh.rdcpix.com/089826b977ea95875d6edfd69cd8d7cel-f856654984r.jpg)

*13 total photos available on [listing page](https://www.propertysimple.com/listing/221-s-highland-street-winchester-ky-40391-26006685)*

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**MLS#:** 26006685 | **Updated:** 2026-04-25
**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/221-s-highland-street-winchester-ky-40391-26006685)

---

## Structured Data

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  "name": "221 S Highland Street, Winchester, KY 40391",
  "description": "INVESTOR SPECIAL, You have the opportunity to purchase a fully occupied tri-plex in the heart of Winchester with instant cash flow. Main level unit is a large 2 bed, one bath. Upstairs unit is also a 2 bed, one bath, and lower level is a 1 bed, one bath unit. There is street parking and alley access with parking in the rear. All units have their own exterior entrance. Some utilities are metered together, landlord does cover utility expenses. Please call with any questions, please do not disturb ",
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```