114 E Winchester Ave, Middlesboro, KY 40965
OFF MARKET

114 E Winchester Ave
Middlesboro, KY 40965

  • 2 Beds
  • 1 Bath
  • 980 sqft
2 Beds
1 Bath
980 sqft

Local Information

  • Map ViewExplore the area around 114 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
Living Area
980 sqft
Parking
None

Description

This single-family home is located at 114 E Winchester Ave, Middlesboro, KY. 114 E Winchester Ave is in Middlesboro, KY and in ZIP code 40965. This property has 2 bedrooms, 1 bathroom and approximately 980 sqft of floor space. This property has a lot size of 5357 sqft.
114 E Winchester Ave, Middlesboro, KY 40965 is a 2 bedroom, 1 bathroom, 980 sqft single-family home. It last sold for $23,000 on Apr 1, 1990. It is currently off market. The Trulia Estimate rent is $1,068/month.

Home Details for 114 E Winchester Ave

Interior Features

Levels, Entrance, & Accessibility
Stories: 1

Exterior Features

Exterior Home Features
Roof: CompositionExterior: OtherFoundation Type: Concrete Block
Parking & Garage
Parking: None

Property Information

Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 5357 sqft

Price History for 114 E Winchester Ave

DatePriceEventSource
04/01/1990$23,000Sold
N/A

Market trends in Middlesboro

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
51
5MoM
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Property Tax and Assessment

Year2024
Tax$208
Assessment$20,000
Home facts updated by county records

Comparable Sales for 114 E Winchester Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
514 Exeter Ave, Middlesboro, KY
0.34
Single-Family Home
$40,000
11/05/25
3
1
1,250
413 S 26th St, Middlesboro, KY
0.44
Single-Family Home
$100,000
02/04/26
2
1
1,008
515 Winchester Ave, Middlesboro, KY
0.35
Single-Family Home
$60,000
09/03/25
3
1
1,100
305 N 15th St, Middlesboro, KY
0.62
Single-Family Home
$50,000
11/03/25
2
1
876
114 W Rochester Ave, Middlesboro, KY
0.13
Single-Family Home
$175,000
12/31/25
3
2
1,008
714 Dorchester Ave, Middlesboro, KY
0.61
Single-Family Home
$175,000
03/03/26
3
1
1,000
422 Wilderness Rd, Middlesboro, KY
0.62
Single-Family Home
$134,500
07/25/25
2
1
850
212 S 22nd St, Middlesboro, KY
0.12
Single-Family Home
$10,000
08/07/25
2
1,682
923 Winchester Ave, Middlesboro, KY
0.70
Single-Family Home
$70,000
07/08/26
1
1
800
707 Gloucester Ave, Middlesboro, KY
0.53
Single-Family Home
$169,900
05/22/26
3
2
1,184

Nearby homes

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Assigned Schools

These are the assigned schools for 114 E Winchester Ave.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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

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Apartments for Rent

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Homes for sale near 114 E Winchester Ave

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Off Market Homes Near 114 E Winchester Ave

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