# 2002 Winchester Avenue, Middlesboro, KY 40965

> **TL;DR:** 2bd/1ba single family, $135,000 ($121/sqft), built 1940, 1,120 sqft.
> A/C. Est. $722/mo. Listed 132 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $135,000 |
| Price/sqft | $121 |
| Bedrooms | 2 |
| Bathrooms | 1 full |
| Square Feet | 1,120 |
| Year Built | 1940 |
| Lot Size | 7,501 sqft (0.17 acres) |
| Stories | 1 |
| Property Type | Single Family (Single Family Residence) |
| Status | Active |
| Days on Market | 132 |

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $683 |
| Estimated Insurance | $39 |
| **Total** | **$722** |

## Nearby Schools

- **Elementary:** Middlesboro Ind
- **Middle:** Middlesboro Ind
- **High:** Middlesboro Ind

## Key Amenities

- A/C

## Property Highlights

- Built in 1940
- 0.17 acre lot

## Description

### Agent Description
CHARMING 2 BEDROOM/ONE BATH HOME! This charming 2 bedroom, 1 bath home offers a perfect blend of comfort and convenience, completely outside of the flood zone. Enjoy leisurely mornings on the large covered front porch or entertain guest on the back deck overlooking your private fully fenced in yard - perfect for pets or gardening. This move in ready property also features a detached 2 -car carport, providing ample shaded parking and storage. Don't miss this gem, conveniently located close to all the local amenities. Plus only a 10 minutes drive to LMU main campus.

## Location

- **Address:** 2002 Winchester Avenue, Middlesboro, KY 40965
- **County:** Bell
- **Neighborhood:** City Limits
- **Coordinates:** 36.602625, -83.74398
- **Google Maps:** https://www.google.com/maps?q=36.602625,-83.74398

## Listing Agent

- **Name:** Sheila Durham
- **Brokerage:** Coldwell Banker Bisceglia Realty & Auction Co
- **Phone:** 6064999029
- **Broker Phone:** 606-269-7970
- **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/2002-Winchester-Ave_Middlesboro_KY_40965_M39521-78493?f=listhub&s=LBARKY&m=26010030&c=propsimple)

## Photos

![2002 Winchester Avenue - Photo 1](http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f161827649r.jpg)

![2002 Winchester Avenue - Photo 2](http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f1376715173r.jpg)

![2002 Winchester Avenue - Photo 3](http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3991117857r.jpg)

![2002 Winchester Avenue - Photo 4](http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f629265248r.jpg)

![2002 Winchester Avenue - Photo 5](http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3451923522r.jpg)

![2002 Winchester Avenue - Photo 6](http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3816763728r.jpg)

![2002 Winchester Avenue - Photo 7](http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f2029492210r.jpg)

![2002 Winchester Avenue - Photo 8](http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f2842526275r.jpg)

![2002 Winchester Avenue - Photo 9](http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f1148827390r.jpg)

![2002 Winchester Avenue - Photo 10](http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3265357044r.jpg)

![2002 Winchester Avenue - Photo 11](http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f921159333r.jpg)

![2002 Winchester Avenue - Photo 12](http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3991049954r.jpg)

![2002 Winchester Avenue - Photo 13](http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f82161789r.jpg)

![2002 Winchester Avenue - Photo 14](http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3422534338r.jpg)

![2002 Winchester Avenue - Photo 15](http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f799708100r.jpg)

![2002 Winchester Avenue - Photo 16](http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f2761337485r.jpg)

![2002 Winchester Avenue - Photo 17](http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f2183220187r.jpg)

![2002 Winchester Avenue - Photo 18](http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3160149428r.jpg)

![2002 Winchester Avenue - Photo 19](http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3034120829r.jpg)

![2002 Winchester Avenue - Photo 20](http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3951483898r.jpg)

![2002 Winchester Avenue - Photo 21](http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3669153614r.jpg)

![2002 Winchester Avenue - Photo 22](http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f1461312734r.jpg)

![2002 Winchester Avenue - Photo 23](http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f2090840322r.jpg)

![2002 Winchester Avenue - Photo 24](http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f2031485426r.jpg)

![2002 Winchester Avenue - Photo 25](http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f1396447850r.jpg)

![2002 Winchester Avenue - Photo 26](http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f1900431011r.jpg)

---

**MLS#:** 26010030 | **Updated:** 2026-09-12
**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/2002-winchester-avenue-middlesboro-ky-40965-26010030)

---

## Structured Data

```json
{
  "@context": "https://schema.org",
  "@type": "RealEstateListing",
  "@id": "https://www.propertysimple.ai/listing/2002-winchester-avenue-middlesboro-ky-40965-26010030#listing",
  "url": "https://www.propertysimple.ai/listing/2002-winchester-avenue-middlesboro-ky-40965-26010030",
  "name": "2002 Winchester Avenue, Middlesboro, KY 40965",
  "description": "CHARMING 2 BEDROOM/ONE BATH HOME! This charming 2 bedroom, 1 bath home offers a perfect blend of comfort and convenience, completely outside of the flood zone. Enjoy leisurely mornings on the large covered front porch or entertain guest on the back deck overlooking your private fully fenced in yard - perfect for pets or gardening. This move in ready property also features a detached 2 -car carport, providing ample shaded parking and storage. Don't miss this gem, conveniently located close to all the local amenities. Plus only a 10 minutes drive to LMU main campus.",
  "image": [
    "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f161827649r.jpg",
    "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f1376715173r.jpg",
    "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3991117857r.jpg",
    "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f629265248r.jpg",
    "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3451923522r.jpg",
    "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3816763728r.jpg",
    "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f2029492210r.jpg",
    "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f2842526275r.jpg",
    "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f1148827390r.jpg",
    "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3265357044r.jpg",
    "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f921159333r.jpg",
    "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3991049954r.jpg",
    "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f82161789r.jpg",
    "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3422534338r.jpg",
    "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f799708100r.jpg",
    "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f2761337485r.jpg",
    "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f2183220187r.jpg",
    "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3160149428r.jpg",
    "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3034120829r.jpg",
    "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3951483898r.jpg",
    "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3669153614r.jpg",
    "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f1461312734r.jpg",
    "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f2090840322r.jpg",
    "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f2031485426r.jpg",
    "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f1396447850r.jpg",
    "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f1900431011r.jpg"
  ],
  "primaryImageOfPage": {
    "@type": "ImageObject",
    "url": "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f161827649r.jpg",
    "caption": "2002 Winchester Avenue - Middlesboro, KY"
  },
  "datePosted": "2026-05-06T00:00:00+00:00",
  "dateModified": "2026-09-12T20:37:29.591631+00:00",
  "mainEntity": {
    "@type": "Accommodation",
    "@id": "https://www.propertysimple.ai/listing/2002-winchester-avenue-middlesboro-ky-40965-26010030#property",
    "name": "2002 Winchester Avenue, Middlesboro, KY 40965",
    "address": {
      "@type": "PostalAddress",
      "streetAddress": "2002 Winchester Avenue",
      "addressLocality": "Middlesboro",
      "addressRegion": "KY",
      "postalCode": "40965",
      "addressCountry": "US"
    },
    "geo": {
      "@type": "GeoCoordinates",
      "latitude": 36.602625,
      "longitude": -83.74398
    },
    "image": [
      "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f161827649r.jpg",
      "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f1376715173r.jpg",
      "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3991117857r.jpg",
      "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f629265248r.jpg",
      "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3451923522r.jpg",
      "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3816763728r.jpg",
      "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f2029492210r.jpg",
      "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f2842526275r.jpg",
      "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f1148827390r.jpg",
      "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3265357044r.jpg",
      "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f921159333r.jpg",
      "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3991049954r.jpg",
      "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f82161789r.jpg",
      "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3422534338r.jpg",
      "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f799708100r.jpg",
      "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f2761337485r.jpg",
      "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f2183220187r.jpg",
      "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3160149428r.jpg",
      "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3034120829r.jpg",
      "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3951483898r.jpg",
      "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f3669153614r.jpg",
      "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f1461312734r.jpg",
      "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f2090840322r.jpg",
      "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f2031485426r.jpg",
      "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f1396447850r.jpg",
      "http://lh.rdcpix.com/abda398869083c064d6c5c80c87ebb24l-f1900431011r.jpg"
    ],
    "identifier": {
      "@type": "PropertyValue",
      "propertyID": "MLS",
      "value": "26010030"
    },
    "accommodationCategory": "Single Family Residence",
    "numberOfBedrooms": 2,
    "numberOfBathroomsTotal": 1,
    "numberOfFullBathrooms": 1,
    "floorSize": {
      "@type": "QuantitativeValue",
      "value": 1120,
      "unitCode": "FTK",
      "unitText": "square feet"
    },
    "yearBuilt": 1940,
    "amenityFeature": [
      {
        "@type": "LocationFeatureSpecification",
        "name": "Heating",
        "value": "Electric (Heating), Heat Pump (Heating)"
      },
      {
        "@type": "LocationFeatureSpecification",
        "name": "Cooling",
        "value": "Electric, Central Air, Heat Pump"
      },
      {
        "@type": "LocationFeatureSpecification",
        "name": "Appliances",
        "value": "Refrigerator, Range"
      },
      {
        "@type": "LocationFeatureSpecification",
        "name": "Flooring",
        "value": "Laminate, Vinyl"
      },
      {
        "@type": "LocationFeatureSpecification",
        "name": "Construction Materials",
        "value": "Vinyl Siding"
      },
      {
        "@type": "LocationFeatureSpecification",
        "name": "Parking Features",
        "value": "Carport"
      },
      {
        "@type": "LocationFeatureSpecification",
        "name": "Air Conditioning",
        "value": true
      }
    ],
    "additionalProperty": [
      {
        "@type": "PropertyValue",
        "name": "Lot Size",
        "value": "0.17 acres"
      },
      {
        "@type": "PropertyValue",
        "name": "Stories",
        "value": 1
      },
      {
        "@type": "PropertyValue",
        "name": "Property Subtype",
        "value": "Single Family Residence"
      }
    ]
  },
  "offers": {
    "@type": "Offer",
    "@id": "https://www.propertysimple.ai/listing/2002-winchester-avenue-middlesboro-ky-40965-26010030#offer",
    "url": "https://www.propertysimple.ai/listing/2002-winchester-avenue-middlesboro-ky-40965-26010030",
    "price": 135000,
    "priceCurrency": "USD",
    "businessFunction": "http://purl.org/goodrelations/v1#Sell",
    "availability": "https://schema.org/InStock",
    "seller": {
      "@id": "https://www.propertysimple.ai/listing/2002-winchester-avenue-middlesboro-ky-40965-26010030#agent"
    }
  },
  "provider": {
    "@type": "Person",
    "@id": "https://www.propertysimple.ai/listing/2002-winchester-avenue-middlesboro-ky-40965-26010030#agent",
    "name": "Sheila Durham",
    "telephone": "6064999029",
    "worksFor": {
      "@type": "Organization",
      "@id": "https://www.propertysimple.ai/listing/2002-winchester-avenue-middlesboro-ky-40965-26010030#brokerage",
      "name": "Coldwell Banker Bisceglia Realty & Auction Co",
      "telephone": "606-269-7970"
    }
  }
}
```