$100,000
$5K PRICE DROP

416 Winchester Ave Middlesboro, KY 40965

Estimated payment $605/month

Total Views 6,714
6 Beds
4 Baths
2,520 Sq Ft
$40 Price per Sq Ft

About This Home

Come check out 416 Winchester Ave Middlesboro KY. This property could be utilized as apartments or as one large unit. Parking allows for 4 vehicles out front and the driveway allows for a couple more. Level lot, tons of space. Public records show the building being built in 1891, there is a metal roof that's approximately a year old, hardwood flooring throughout with a mix of some vinyl flooring. The property does need some work but would make a nice rental producing property. City water, city sewer, high speed internet. Property is being sold as is and all information pertaining to the property was taken from public records.

Listing Agent

Megan Stanaford

Black Diamond Realty License #296125 Listed on: 07/10/2025

Black Diamond Realty

Property Details

Home Type

  • Apartment

Est. Annual Taxes

  • $729

Year Built

  • Built in 1891

Parking

  • Parking Available

Home Design

  • Metal Roof

Interior Spaces

  • 2,520 Sq Ft Home
  • 2-Story Property

Bedrooms and Bathrooms

  • 6 Bedrooms
  • 4 Full Bathrooms

Schools

  • Middlesboro Ind
  • Not Applicable Middle School
  • Middlesboro Ind High School

Additional Features

  • 9,148 Sq Ft Lot
  • Heating Available

Community Details

  • 2 Units
  • City Limits Subdivision

Listing and Financial Details

  • Assessor Parcel Number 069-44-10-008.00

Property Details

Home Type

Apartment

Est. Annual Taxes

$729

Year Built

Built in 1891

Lot Details

0

Listing Details

  • Property Type: Residential Income
  • Structure Type: Apartments
  • Year Built: 1891
  • Location Tax Legal Info:Elementary School: Middlesboro Ind
  • Location Tax Legal Info:Middle or Junior School: Middlesboro Ind
  • Location Tax Legal Info:High School: Middlesboro Ind
  • Location Tax Legal Info:Intermediate School: Not Applicable
  • Contract Info:On Market Date: 2025-07-09
  • General Property Description:Lot Size Acres: 0.21
  • Utilities:Electricity2: Electricity Connected
  • Utilities Sewer: Sewer Connected
  • Water: Water Connected
  • Roof:Metal3: Yes
  • General Property Description:Approximate Living Area: 2520.0
  • General Property Description:Number of Buildings: One
  • General Property Description:Number of Stories: Two
  • Unit Info:_pound_ of Units: 2
  • Structure Type:Apartments: Yes
  • Special Features: None
  • Property Sub Type: MultiFamily

Interior Features

  • Full Bathrooms: 4
  • Total Bathrooms: 4
  • Total Bedrooms: 6
  • Lot Size Area: 0.21

Exterior Features

  • Roof: Metal
  • List Price: 100000.0

Garage/Parking

  • Parking 1 - 5 Spaces: Yes

Utilities

  • Heating: Electric
  • Heating: Yes
  • Heating:Electric: Yes

Schools

  • Elementary School: Middlesboro Ind
  • High School: Middlesboro Ind
  • Middle or Junior School: Middlesboro Ind

Lot Info

  • Lot Size Acres: 0.21
  • Lot Size Sq Ft: 9148.0
  • Parcel Number: 069-44-10-008.00
  • Zoning Description: City

Multi Family

  • Number of Units Total: 2

Map

Range of Values:

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Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2024 $729 $70,000 $70,000 $0
2023 $733 $70,000 $0 $0
2022 $950 $90,000 $0 $0
2021 $960 $90,000 $0 $0
2020 $963 $90,000 $0 $0
2019 $964 $90,000 $0 $0
2018 $898 $90,000 $0 $0
2017 $896 $90,000 $0 $0
2016 $892 $90,000 $0 $0
2014 $826 $90,000 $0 $0
2011 $51 $90,000 $0 $0
Source: Public Records

Property History

Date Event Price Change Sq Ft Price
07/25/2025 07/25/25 Price Changed $100,000 -4.8% $40 / Sq Ft
07/10/2025 07/10/25 For Sale $105,000 -- $42 / Sq Ft
Source: ImagineMLS (Bluegrass REALTORS®)

Purchase History

Date Type Sale Price Title Company
Warranty Deed $70,000 Imag Title
Commissioners Deed $67,500 --
Source: Public Records

Source: ImagineMLS (Bluegrass REALTORS®)

MLS Number: 25014789

ImagineMLS (Bluegrass REALTORS®)

APN: 069-44-10-008.00