416 Winchester Ave Middlesboro, KY 40965
Property details
About 416 Winchester Ave
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.
Highlights
Summary
- Full Bathrooms: 4
- Total Bedroom Count: 6
- Parking: 1 - 5 Spaces
- Heating: Electric
- List Price: $105,000
- Price/SqFt: $41
- Annual Tax Amount: $732
- Tax Year: 2023
- Directions: From Hearthside bank on Cumberland Ave, turn right onto Cumberland Ave. In 0.4 of a mile turn left onto S 21St Street then right onto Winchester Ave. Property will be on your right in 0.2 of a mile.
- Year Built: 1891
- Stories: 2
- Living Area: 2,520 SqFt
- Lot Size: 0.21 Acres
- MLS Number: 25014789
- Office Name: Black Diamond Realty
- Office Phone: (606) 552-0879
- Office Email: myblackdiamondrealty@gmail.com
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Data displayed may be a portion of, and not a complete set of all listings published in the MLS.
Last updated on: 7/13/2025, 10:45:32 AM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.
Price information
Property sales
We're sorry, we currently don't have property sales data for this listing.
Tax history
| Year | Assessment | Property Tax |
|---|---|---|
| 2023 | $70,000 | $732 |
| 2022 | $90,000 | $950 |
| 2021 | $90,000 | $960 |
| 2019 | $90,000 | $963 |
| 2018 | $90,000 | $898 |
| 2017 | $90,000 | $- |
History based on county public records data.
Nearby schools
5
Middlesboro Elementary School
Public District PK-4
1.0 mi
•3400 Cumberland Ave
4
Ellen Myers Primary School
Public District PK-4
3.7 mi
•275 Nettleton Rd
6
Tazewell-New Tazewell Elementary School
Public District KG-4
13.4 mi
•501 Davis Dr
School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.
Neighborhood
The neighbors living near this home have an average income of $27,966. The most common annual income of people living in Middlesboro, KY is less than $<35k. The majority of families are single, no kids. The most common level of education of people living in this area is high school diploma.
How much money do the neighbors make?
What level of education do the neighbors have?
What types of families live nearby?
Are the neighbors home owners or renters?
How old are people in this area?
What do the neighbors do for fun?
Figure Skating
Pro Wrestling
Extreme Sports
Where do the neighbors shop?
Kmart
Wal-Mart
Academy Sports & Outdoors
Where do the neighbors go to eat?
Bob Evans
Sonic
Little Caesars
What do the neighbors drive?
Buick
Oldsmobile
Chevrolet
What do the neighbors listen to?
Oldies- Contemporary Inspirational
Country
Frequently asked questions
Living in Middlesboro, KY
Transportation in Middlesboro includes a network of roads that connect residents to nearby cities and amenities. Public transit options are available, with schedules that cater to the needs of the community. The area's walkability varies, with certain neighborhoods being more pedestrian-friendly than others. Ride-sharing services are present, offering additional transportation choices for residents.
The community is served by a number of public schools, ensuring educational opportunities for children at various levels. Healthcare needs are met by local clinics and a hospital that provides a range of services from primary care to emergency treatment. Retail and dining options are available, with local businesses reflecting the culture and tastes of Middlesboro. The public library system supports the community's educational and informational needs.
Middlesboro is known for its welcoming atmosphere and a sense of tight-knit community. The area prides itself on local events that bring residents together, reflecting the town's cultural identity and values. The community's character is further defined by its scenic surroundings and local parks, which contribute to the town's peaceful and family-friendly ambiance.
Middlesboro's housing market offers a blend of residential options, with single-family homes being a significant component. The architectural styles vary, providing a mix of traditional and contemporary designs that cater to a range of preferences. While the exact composition of the housing market is not specified, there is a presence of both homeowners and renters within the community.
About 416 Winchester Ave
The listing price of 416 Winchester Ave property is $105,000.
The property 416 Winchester Ave is a multi located in Middlesboro, Kentucky, 40965.
Active Listing: 416 Winchester Ave is For Sale (Active/New) which means the seller is accepting offers.
The nearby schools for 416 Winchester Ave are: Middlesboro Elementary School (GreatSchools Rating 5/10), Ellen Myers Primary School (GreatSchools Rating 4/10), Tazewell-New Tazewell Elementary School (GreatSchools Rating 6/10), Middlesboro Middle School (GreatSchools Rating 4/10), Yellow Creek School Center (GreatSchools Rating 7/10), H. Y. Livesay Middle School (GreatSchools Rating 7/10), Middlesboro High School (GreatSchools Rating 4/10), Cumberland Gap High School (GreatSchools Rating 5/10), Bell County High School (GreatSchools Rating 6/10).
According to the records, the last property tax for 2023 is $732 (source: MLS/based on county public records data).
The property 416 Winchester Ave is 2,520 SqFt (source: MLS/tax record).
The year of construction for 416 Winchester Ave is 1891.
This home is located at 416 Winchester Ave in Middlesboro, KY and zip code 40965. This 2,520 square foot home, which was built in 1891, sits on a 0.21 acre lot. Features: 6 bedrooms, 4 bathrooms. It has been listed on Rocket Homes since July 10, 2025 and is currently priced at $105,000.
Middlesboro, KY housing market in June 2025 saw over 1 listings sold above listed price, more than 0 sold at listed price and over 3 sold below. Between May and June 2025, Middlesboro, KY real estate market has seen increase in the number of listings by 1.8%. While the average time on the market in June 2025 was 375 days, the median list price was $160,000.