116 E Winchester Ave, Middlesboro, KY 40965
OFF MARKET

116 E Winchester Ave
Middlesboro, KY 40965

  • Studio
  • 1 Bath
  • 2,182 sqft

$109,900

Trulia Estimate
as of May 28, 2026
Est. Refi. Payment $696/mo*
Refinance Your Home

$109,900

Trulia Estimate
as of May 28, 2026
Est. Refi. Payment $696/mo*
Refinance Your Home
Studio
1 Bath
2,182 sqft

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
No Info

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 History for 116 E Winchester Ave

DatePriceEventSource
06/21/2007$62,000Sold
N/A
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Property Tax and Assessment

Year2024
Tax$645
Assessment$62,000
Home facts updated by county records

Comparable Sales for 116 E Winchester Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
407 N 24th St, Middlesboro, KY
0.54
Single-Family Home
$65,000
08/25/25
1
2,019
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
112 Exeter Ave, Middlesboro, KY
0.05
Single-Family Home
$80,000
07/24/25
1
1,236
212 S 22nd St, Middlesboro, KY
0.14
Single-Family Home
$10,000
08/07/25
2
1,682
413 S 26th St, Middlesboro, KY
0.47
Single-Family Home
$100,000
02/04/26
2
1
1,008
725 Winchester Ave, Middlesboro, KY
0.51
Single-Family Home
$50,000
03/27/26
1
820
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
414 N 24th St, Middlesboro, KY
0.33
Single-Family Home
$167,000
09/15/25
4
2
1,600

Nearby homes

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Assigned Schools

These are the assigned schools for 116 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

  • 79 % Say there's holiday spirit

  • 71 % Say kids play outside

  • 68 % 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

Apartments for Rent

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Homes for sale near 116 E Winchester Ave

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Off Market Homes Near 116 E Winchester Ave

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Homes for rent near 116 E Winchester Ave

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116 E Winchester Ave, Middlesboro, KY 40965 is a studio, 1 bathroom, 2,182 sqft single-family home built in 1910. This property is not currently available for sale. 116 E Winchester Ave was last sold on Jun 21, 2007 for $62,000. The current Trulia Estimate for 116 E Winchester Ave is $109,900.