# 265 S Highland Street, Winchester, KY 40391

> **TL;DR:** 8bd/4ba residential multi family, $505,000 ($100/sqft), built 1940, 5,058 sqft.
> A/C. Est. $2,188/mo. Listed 29 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $505,000 |
| Price/sqft | $100 |
| Bedrooms | 8 |
| Bathrooms | 4 full |
| Square Feet | 5,058 |
| Year Built | 1940 |
| Lot Size | 6,098 sqft (0.14 acres) |
| Stories | 2 |
| Property Type | Residential Multi Family (Other) |
| Status | For Sale |
| Days on Market | 29 |

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Mortgage (20% down, 6.5%) | $2,188 |
| **Total** | **$2,188** |

## Nearby Schools

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

## Key Amenities

- A/C

## Property Highlights

- Built in 1940
- 0.14 acre lot
- 2 stories

## Description

### Agent Description
Great investment opportunity in downtown Winchester! This spacious quadplex has been updated throughout and offers a true turn-key multi-family property. Each unit features two bedrooms, one bathroom, a full kitchen, and its own private laundry area. Utilities are separately metered, allowing tenants to handle their own services and helping keep operating costs manageable. With a total of 8 bedrooms, 4 bathrooms, and approximately 5058 square feet, this property provides strong rental potential in a convenient location close to downtown shopping, dining, and local amenities. The units are clean, well-maintained, and ready for new tenants, making this an excellent option for investors seeking a solid income-producing property. Schedule your showing today before this opportunity is gone!

## Location

- **Address:** 265 S Highland Street, Winchester, KY 40391
- **County:** Clark
- **Neighborhood:** Downtown
- **Coordinates:** 37.987145, -84.177947
- **Google Maps:** https://www.google.com/maps?q=37.987145,-84.177947

## Listing Agent

- **Name:** J Corey Griffo
- **Brokerage:** RE/MAX Elite Lexington
- **Phone:** 5028047067
- **Email:** james.c.griffo@gmail.com

## Primary Photo

![265 S Highland Street - Primary Photo](http://lh.rdcpix.com/eabe69e973ba2ead04b80fc721a0d35al-f3921707716r.jpg)

*31 total photos available on [listing page](https://www.propertysimple.com/listing/265-s-highland-street-winchester-ky-40391-26004961)*

---

**MLS#:** 26004961 | **Updated:** 2026-04-24
**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/265-s-highland-street-winchester-ky-40391-26004961)

---

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