Chester Ave, Middlesboro, KY 40965
OFF MARKET

$135,500

Trulia Estimate
  • Studio

Chester Ave, Middlesboro, KY 40965

Est. Refi. Payment $890/mo*
Refinance Your Home
Currently Off Market - Sold Oct 8, 2013 for $35,000

Home Value

Trulia Estimate
$136K
Since last month
Increased$300 (+0.2%)
Since last year
Increased$37K (+36.3%)
Since last sale
Increased$102K (+291.4%)
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 +359% in the last 10 years
MonthEstimated value
2026
September 2026$137K
June 2026$137K
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
316 Exeter Ave, Middlesboro, KY
0.12
Single-Family Home
$65,000
07/31/26
4
2
2,592
514 Exeter Ave, Middlesboro, KY
0.24
Single-Family Home
$40,000
11/05/25
3
1
1,250
114 W Rochester Ave, Middlesboro, KY
0.26
Single-Family Home
$175,000
12/31/25
3
2
1,008
304 W Chester Ave, Middlesboro, KY
0.02
Single-Family Home
$87,000
03/12/26
1
1,344
315 S 24th St, Middlesboro, KY
0.16
Single-Family Home
$22,500
12/23/25
1
816
705 Worchester Ave, Middlesboro, KY
0.49
Single-Family Home
$31,667
10/22/25
-
1,036
119 Fleetwood Rd, Middlesboro, KY
0.58
Single-Family Home
$16,800
08/20/26
6
1
1,197
419 S 20th St, Middlesboro, KY
0.30
Single-Family Home
$45,000
05/29/26
-
1,056
132 S 21st St, Middlesboro, KY
0.12
Single-Family Home
$141,000
10/06/25
-
5,880
727 Winchester Ave, Middlesboro, KY
0.37
Single-Family Home
$115,000
10/09/25
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
312 W Chester Ave, Middlesboro, KY 40965
0.02
$299,000
6
4
3,594
For Sale
307 W Chester Ave, Middlesboro, KY 40965
0.02
$113,500
3
3
2,064
Off Market
321 E Chester Ave, Middlesboro, KY 40965
0.04
$275,000
-
-
-
For Sale
407 22nd St, Middlesboro, KY 40965
0.11
$113,000
2
1
1,116
Off Market
403 Winchester Ave, Middlesboro, KY 40965
0.12
$120,000
-
-
-
Recently Sold
316 Exeter Ave, Middlesboro, KY 40965
0.12
$65,000
4
2
2,592
Recently Sold
501 W Chester Ave, Middlesboro, KY 40965
0.14
$107,200
2
1
948
Off Market
312 S 23rd St, Middlesboro, KY 40965
0.12
$120,700
3
2
1,870
Off Market
306 Exeter Ave, Middlesboro, KY 40965
0.13
$108,600
3
2
1,760
Off Market
311 S 22nd St, Middlesboro, KY 40965
0.13
-
3
1
1,548
Off Market
400 Gloucester Ave, Middlesboro, KY 40965
0.19
$279,000
4
2
2,032
For Sale
512 W Chester Ave, Middlesboro, KY 40965
0.16
$126,200
3
2
2,100
Off Market

Local Information

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

Home Highlights

Single-Family Home
0.85 acre lot

About this House

This single-family home is located at Chester Ave, Middlesboro, KY. Chester Ave is in Middlesboro, KY and in ZIP code 40965. This property has a lot size of 0.85 acres.
Chester Ave, Middlesboro, KY 40965 is a studio single-family home. It last sold for $35,000 on Oct 8, 2013. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $135,500, with a rent estimate of $1,878/month.

Home Details for Chester Ave

Property Information

Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 0.85 acres

Price and Tax history

DateEventPrice
Oct 8, 2013
Source: N/A
Sold
$35,000

Market trends in Middlesboro

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
47
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 Chester Ave

  • What is Chester Ave estimated to be worth?
    Trulia's estimated value for Chester Ave in Middlesboro, KY is $135,500.
  • What is the price history for Chester Ave?
    Chester Ave in Middlesboro, KY last sold for $35,000 in October 2013.
  • Is Middlesboro a buyer's or seller's market?
    Middlesboro is currently a balanced 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 Chester Ave?
    The lot at Chester Ave in Middlesboro, KY is about 0.85 acres (36,851 sq ft).

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Off Market Homes Near Chester Ave

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