1602 Winchester Ave, Middlesboro, KY 40965
OFF MARKET

1602 Winchester Ave
Middlesboro, KY 40965

  • Studio
  • 1 Bath
  • 1,032 sqft (on 0.40 acres)

$121,900

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $771/mo*
Refinance Your Home

$121,900

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $771/mo*
Refinance Your Home
Studio
1 Bath
1,032 sqft
(on 0.40 acres)

Home Value

Trulia Estimate
$122K
Since last month
Decreased$4K (-2.8%)
Since last year
Decreased$1K (-1.1%)
Since last sale
Increased$58K (+89.8%)
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 +63% in the last 10 years
MonthEstimated value
2026
August 2026$123K
July 2026$127K
June 2026$125K
May 2026$130K
April 2026$135K
March 2026$130K
February 2026$130K
January 2026$115K
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
1720 Exeter Ave, Middlesboro, KY
0.16
Single-Family Home
$84,000
04/30/26
2
1
1,456
1807 Winchester Ave, Middlesboro, KY
0.15
Single-Family Home
$152,500
07/21/26
3
1
1,104
409 Meadow Ln, Middlesboro, KY
0.17
Single-Family Home
$168,000
04/22/26
4
1.5
1,120
923 Winchester Ave, Middlesboro, KY
0.57
Single-Family Home
$70,000
07/08/26
1
1
800
1618 Winchester Ave, Middlesboro, KY
0.04
Single-Family Home
$103,000
08/25/25
2
1,240
1315 Winchester Ave, Middlesboro, KY
0.23
Single-Family Home
$210,500
12/22/25
2
1,684
515 Winchester Ave, Middlesboro, KY
0.92
Single-Family Home
$60,000
09/03/25
3
1
1,100
106 S 38th St, Middlesboro, KY
0.28
Single-Family Home
$180,000
10/21/25
3
2
1,404
164 Walker Ln, Middlesboro, KY
0.50
Single-Family Home
$176,500
02/11/26
3
1.5
1,040
140 Chasteen Dr, Middlesboro, KY
0.33
Single-Family Home
$202,000
02/17/26
3
2
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
1618 W Winchester Ave, Middlesboro, KY 40965
0.05
$128,800
3
1.5
1,200
Off Market
1619 Winchester Ave, Middlesboro, KY 40965
0.06
$76,300
2
1.5
1,364
Off Market
1807 Winchester Ave, Middlesboro, KY 40965
0.15
$152,500
3
1
1,104
Recently Sold
1720 Exeter Ave, Middlesboro, KY 40965
0.16
$115,000
2
1
1,456
For Sale
409 Meadow Ln, Middlesboro, KY 40965
0.17
$168,000
4
1.5
1,120
Recently Sold
1408 Exeter Ave, Middlesboro, KY 40965
0.20
$179,300
3
2
1,404
Off Market
1813 Winchester Ave, Middlesboro, KY 40965
0.18
$66,300
2
1
1,008
Off Market
3306 W Cumberland Ave, Middlesboro, KY 40965
0.23
$340,000
3
2
2,126
Recently Sold
405 S 37th St, Middlesboro, KY 40965
0.19
$129,900
4
2
1,908
For Sale
1801 Exeter Ave, Middlesboro, KY 40965
0.20
-
2
1
700
Off Market
1408 W Rochester Ave, Middlesboro, KY 40965
0.24
$212,700
3
2
2,184
Off Market
1809 Exeter Ave, Middlesboro, KY 40965
0.23
$40,900
3
1
1,064
Off Market

Local Information

  • Map ViewExplore the area around 1602 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
1984
Lot Size
0.4 acres
Living Area
1,032 sqft
Price/Sqft
$118
Parking
Garage

About this House

This single-family home is located at 1602 Winchester Ave, Middlesboro, KY. 1602 Winchester Ave is in Middlesboro, KY and in ZIP code 40965. This property has 1 bathroom and approximately 1,032 sqft of floor space. This property has a lot size of 0.40 acres and was built in 1984.
1602 Winchester Ave, Middlesboro, KY 40965 is a studio, 1 bathroom, 1,032 sqft single-family home built in 1984. It last sold for $65,000 on Jun 1, 2001. It is currently off market. The Trulia Estimate is $121,900, with a rent estimate of $1,423/month.

Home Details for 1602 Winchester Ave

Interior Features

Heating & Cooling
Heating: ElectricHeating Fuel: Electric
Levels, Entrance, & Accessibility
Stories: 1

Exterior Features

Exterior Home Features
Roof: CompositionExterior: Brick
Parking & Garage
GarageParking: Garage Attached, Off Street

Property Information

Year Built
Year Built: 1984
Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 0.40 acres

Price and Tax history

DateEventPrice
Jun 1, 2001
Source: N/A
Sold
$65,000

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
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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

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Apartments for Rent

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Homes for sale near 1602 Winchester Ave

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Off Market Homes Near 1602 Winchester Ave

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Frequently asked questions about 1602 Winchester Ave

  • What is 1602 Winchester Ave estimated to be worth?
    Trulia's estimated value for 1602 Winchester Ave in Middlesboro, KY is $121,900.
  • What is the price history for 1602 Winchester Ave?
    1602 Winchester Ave in Middlesboro, KY last sold for $65,000 in June 2001.
  • 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 1602 Winchester Ave?
    The lot at 1602 Winchester Ave in Middlesboro, KY is about 0.40 acres (17,511 sq ft).
  • Does 1602 Winchester Ave have a garage?
    Yes, 1602 Winchester Ave in Middlesboro, KY has a garage.