# 508 & 512 Winchester Avenue, Middlesboro, KY 40965

> **TL;DR:** 2bd/2ba multi-family, $960,000 ($143/sqft), built 1980, 6,696 sqft.
> A/C. Est. $4,160/mo. Listed 63 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $960,000 |
| Price/sqft | $143 |
| Bedrooms | 2 |
| Bathrooms | 2 full |
| Square Feet | 6,696 |
| Year Built | 1980 |
| Lot Size | 23,958 sqft (0.55 acres) |
| Stories | 2 |
| Property Type | Multi-Family (Apartment) |
| Status | For Sale |
| Days on Market | 63 |

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Mortgage (20% down, 6.5%) | $4,160 |
| **Total** | **$4,160** |

## Nearby Schools

- **High:** Middlesboro Ind

## Key Amenities

- A/C

## Property Highlights

- Built in 1980
- 0.55 acre lot
- 2 stories
- 12 parking spaces

## Description

### Agent Description
Prime Multi-Family Investment Opportunity - 508 & 512 Winchester Avenue, Middlesboro, KY This exceptional offering presents two adjacent multi-family apartment buildings totaling 13,392 square feet of living area on a combined 1.23 acres of land. Located at 508 Winchester Ave (6,696 sq ft on 0.55 acres) and 512 Winchester Ave (6,696 sq ft on 0.68 acres), these properties provide a rare chance to acquire substantial rental inventory in one convenient location. Built for efficiency and scale, each building offers significant square footage ideal for multiple residential units, making them well-suited for investors seeking strong cash flow potential in the Middlesboro market. The generous lot sizes allow for ample parking, green space, or future expansion opportunities. Situated along Winchester Avenue, the properties benefit from convenient access to local amenities, major thoroughfares, and the broader Middlesboro community. Whether you're an experienced multifamily investor or looking to expand your portfolio, this paired offering represents a solid foundation for long-term rental income and value appreciation.

## Location

- **Address:** 508 & 512 Winchester Avenue, Middlesboro, KY 40965
- **County:** Bell
- **Neighborhood:** City Limits
- **Coordinates:** 36.604661, -83.721167
- **Google Maps:** https://www.google.com/maps?q=36.604661,-83.721167

## Listing Agent

- **Name:** Beth Combs
- **Brokerage:** Turn Key Realty
- **Phone:** 6062691807
- **Email:** bethcombs9390@yahoo.com

## Primary Photo

![508 & 512 Winchester Avenue - Primary Photo](http://lh.rdcpix.com/79c44bd2bd9ebbfb7117de31dd45d13fl-f3090087859r.jpg)

*2 total photos available on [listing page](https://www.propertysimple.com/listing/508-512-winchester-avenue-middlesboro-ky-40965-26007224)*

---

**MLS#:** 26007224 | **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/508-512-winchester-avenue-middlesboro-ky-40965-26007224)

---

## Structured Data

```json
{
  "@context": "https://schema.org",
  "@type": "RealEstateListing",
  "name": "508 & 512 Winchester Avenue, Middlesboro, KY 40965",
  "description": "Prime Multi-Family Investment Opportunity - 508 & 512 Winchester Avenue, Middlesboro, KY This exceptional offering presents two adjacent multi-family apartment buildings totaling 13,392 square feet of living area on a combined 1.23 acres of land. Located at 508 Winchester Ave (6,696 sq ft on 0.55 acres) and 512 Winchester Ave (6,696 sq ft on 0.68 acres), these properties provide a rare chance to acquire substantial rental inventory in one convenient location. Built for efficiency and scale, each",
  "url": "https://www.propertysimple.com/listing/508-512-winchester-avenue-middlesboro-ky-40965-26007224",
  "image": "http://lh.rdcpix.com/79c44bd2bd9ebbfb7117de31dd45d13fl-f3090087859r.jpg",
  "datePosted": "2026-06-18",
  "price": 960000,
  "priceCurrency": "USD",
  "address": {
    "@type": "PostalAddress",
    "streetAddress": "508 & 512 Winchester Avenue",
    "addressLocality": "Middlesboro",
    "addressRegion": "KY",
    "postalCode": "40965",
    "addressCountry": "US"
  },
  "geo": {
    "@type": "GeoCoordinates",
    "latitude": 36.604661,
    "longitude": -83.721167
  },
  "numberOfBedrooms": 2,
  "numberOfBathroomsTotal": 2,
  "numberOfFullBathrooms": 2,
  "floorSize": {
    "@type": "QuantitativeValue",
    "value": 6696,
    "unitCode": "FTK"
  },
  "yearBuilt": 1980
}
```