116 E Winchester Ave, Middlesboro, KY 40965
OFF MARKET

$115,000

Trulia Estimate
  • Studio
  • 1 Bath
  • 2,182 sqft

116 E Winchester Ave, Middlesboro, KY 40965

Est. Refi. Payment $740/mo*
Refinance Your Home
Currently Off Market - Sold Jun 21, 2007 for $62,000

Home Value

Trulia Estimate
$115K
Since last month
Increased$4K (+4%)
Since last year
Increased$9K (+8.8%)
Since last sale
Increased$53K (+85.5%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +76% in the last 10 years
MonthEstimated value
2026
August 2026$115K
July 2026$111K
June 2026$117K
May 2026$115K
April 2026$115K
March 2026$115K
February 2026$106K
January 2026$101K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
514 Exeter Ave, Middlesboro, KY
0.37
Single-Family Home
$40,000
11/05/25
3
1
1,250
515 Winchester Ave, Middlesboro, KY
0.37
Single-Family Home
$60,000
09/03/25
3
1
1,100
316 Exeter Ave, Middlesboro, KY
0.20
Single-Family Home
$65,000
07/31/26
4
2
2,592
413 S 26th St, Middlesboro, KY
0.47
Single-Family Home
$100,000
02/04/26
2
1
1,008
727 Winchester Ave, Middlesboro, KY
0.52
Single-Family Home
$115,000
10/09/25
1
1,800
304 W Chester Ave, Middlesboro, KY
0.18
Single-Family Home
$87,000
03/12/26
1
1,344
725 Winchester Ave, Middlesboro, KY
0.51
Single-Family Home
$110,000
07/09/26
1
820
414 N 24th St, Middlesboro, KY
0.33
Single-Family Home
$167,000
09/15/25
4
2
1,600
305 N 15th St, Middlesboro, KY
0.60
Single-Family Home
$50,000
11/03/25
2
1
876
923 Winchester Ave, Middlesboro, KY
0.72
Single-Family Home
$70,000
07/08/26
1
1
800

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
215 S 21st St, Middlesboro, KY 40965
0.03
$120,000
5
4
2,844
For Sale
117 Winchester Ave, Middlesboro, KY 40965
0.02
-
-
-
-
Off Market
415 S 21st St, Middlesboro, KY 40965
0.09
-
3
2
1,750
Off Market
201 Exeter Ave, Middlesboro, KY 40965
0.10
$141,700
3
2
1,485
Off Market
205 Exeter Ave, Middlesboro, KY 40965
0.11
$15,000
-
-
-
For Sale
401 S 20th St, Middlesboro, KY 40965
0.11
$84,100
3
2
920
Off Market
311 S 22nd St, Middlesboro, KY 40965
0.12
-
3
1
1,548
Off Market
407 22nd St, Middlesboro, KY 40965
0.14
$113,700
2
1
1,116
Off Market
209 S 19th St, Middlesboro, KY 40965
0.13
$215,000
3
2
1,352
For Sale
119 S 20th St, Middlesboro, KY 40965
0.16
$250,000
2
2
1,750
For Sale
114 W Rochester Ave, Middlesboro, KY 40965
0.13
$175,000
3
2
1,008
Recently Sold
307 W Chester Ave, Middlesboro, KY 40965
0.16
$133,100
3
3
2,064
Off Market

Local Information

  • Map ViewExplore the area around 116 E Winchester Ave.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1910
Living Area
2,182 sqft
Price/Sqft
$53
Parking
Garage

About this House

This single-family home is located at 116 E Winchester Ave, Middlesboro, KY. 116 E Winchester Ave is in Middlesboro, KY and in ZIP code 40965. This property has 1 bathroom and approximately 2,182 sqft of floor space. This property has a lot size of 5357 sqft and was built in 1910.
116 E Winchester Ave, Middlesboro, KY 40965 is a studio, 1 bathroom, 2,182 sqft single-family home built in 1910. It last sold for $62,000 on Jun 21, 2007. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $115,000, with a rent estimate of $1,462/month.

Home Details for 116 E Winchester Ave

Interior Features

Heating & Cooling
Heating: GasHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 1.5
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: CompositionFoundation Type: Slab
Parking & Garage
GarageParking: Garage Detached, Off Street

Property Information

Year Built
Year Built: 1910
Property Type / Style
Property Type: Single Family HomeArchitecture: A-frame

Lot Information

Lot Area: 5357 sqft

Price and Tax history

DateEventPrice
Jun 21, 2007
Source: N/A
Sold
$62,000

Market trends in Middlesboro

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
49
2MoM

Around this home

What Locals Say about Middlesboro

At least 43 Trulia users voted on each feature.

  • 93 % Say car is needed

  • 87 % Say yards are well-kept

  • 81 % Say parking is easy

  • 77 % Say there's holiday spirit

  • 71 % Say kids play outside

  • 69 % Say it's dog friendly

  • 61 % Say they plan to stay for at least 5 years

  • 58 % Say there's wildlife

  • 54 % Say neighbors are friendly

  • 52 % Say people would walk alone at night

  • 49 % Say it's quiet

  • 44 % Say there are sidewalks

  • 40 % Say it's walkable to restaurants

  • 37 % Say streets are well-lit

  • 28 % Say there are community events

  • 27 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Dawn R.
    "There is a big National park for hiking and dog walking within 2 minutes of. Middlesboro and Hours of fun hiking and walking the dog. "
    2
    Flag
  • Johanna.bowling
    "I drive to work ( Realtor) and I drive my kids to school although they could take the school bus if they wanted . It is a small community and it is fairly easy to get around town , everything is close by "
    2
    Flag
  • Jared C.
    "It's amazing!!! Great community and good neighborhood watch group. Safe streets and clean area. National Park nearby with good hiking trails and amazing views."
    1
    Flag
  • Dawn R.
    "Feeling of being in the country but within city limits. Small town living, free concerts, festivals, hiking, kayaking and other forms of entertainment. "
    1
    Flag
  • Jared C.
    "It is the safest neighborhood in the county. We have a neighborhood watch group. Also beautiful views of the mountains and close to town."
    0
    Flag
  • loulou8094
    "I live here and this is a beautiful neighborhood, quit, within walking distance to everything in town, just a nice area"
    0
    Flag
  • Laura K.
    "It's a quiet branch off Greenwood, not too many folks on this street, back off the road so low traffic and noise, walking distance of Ford Woods Park and if you really like to walk you can go down the hill to the Post office or City hall or even Kroger. Middlesboro is not much for nightlife or public transportation in general. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 116 E Winchester Ave

  • What is 116 E Winchester Ave estimated to be worth?
    Trulia's estimated value for 116 E Winchester Ave in Middlesboro, KY is $115,000.
  • What is the price history for 116 E Winchester Ave?
    116 E Winchester Ave in Middlesboro, KY last sold for $62,000 in June 2007.
  • Is Middlesboro a buyer's or seller's market?
    Middlesboro is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Middlesboro?
    Residents describe Middlesboro, KY as well-kept, easy to park in, and dog-friendly. Most residents say you need a car. See recently sold homes in Middlesboro, KY.
  • How big is the lot at 116 E Winchester Ave?
    The lot at 116 E Winchester Ave in Middlesboro, KY is about 0.12 acres (5,357 sq ft).
  • Does 116 E Winchester Ave have a garage?
    Yes, 116 E Winchester Ave in Middlesboro, KY has a garage.

Apartments for Rent

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Off Market Homes Near 116 E Winchester Ave

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