217 E Chester Ave, Middlesboro, KY 40965
OFF MARKET

$122,000

Trulia Estimate
  • Studio
  • 2 Baths
  • 1,584 sqft

217 E Chester Ave, Middlesboro, KY 40965

Est. Refi. Payment $795/mo*
Refinance Your Home
Currently Off Market - Sold Mar 17, 2009 for $48,000

Home Value

Trulia Estimate
$122K
Since last month
Decreased$6K (-4.9%)
Since last year
Increased$22K (+22.5%)
Since last sale
Increased$74K (+154.4%)
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 +157% in the last 10 years
MonthEstimated value
2026
August 2026$122K
July 2026$128K
June 2026$130K
May 2026$130K
April 2026$121K
March 2026$124K
February 2026$119K
January 2026$96K
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
0.57
Single-Family Home
$40,000
11/05/25
3
1
1,250
305 N 15th St, Middlesboro, KY
0.39
Single-Family Home
$50,000
11/03/25
2
1
876
414 N 24th St, Middlesboro, KY
0.54
Single-Family Home
$167,000
09/15/25
4
2
1,600
316 Exeter Ave, Middlesboro, KY
0.41
Single-Family Home
$65,000
07/31/26
4
2
2,592
206 Summit Dr, Middlesboro, KY
0.34
Single-Family Home
$240,000
06/23/26
4
2.5
1,832
114 W Rochester Ave, Middlesboro, KY
0.29
Single-Family Home
$175,000
12/31/25
3
2
1,008
307 Englewood Rd, Middlesboro, KY
0.48
Single-Family Home
$3,000
03/05/26
2
1,072
707 Gloucester Ave, Middlesboro, KY
0.71
Single-Family Home
$169,900
05/22/26
3
2
1,184
708 Ilchester Ave, Middlesboro, KY
0.76
Single-Family Home
$175,000
01/13/26
3
2
1,312
114 W Rochester Ave, Middlesboro, KY
0.27
Single-Family Home
$175,000
01/23/26
1
918

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
240 S 19th St, Middlesboro, KY 40965
0.07
$119,500
3
1
1,500
Off Market
421 Queensbury Heights Rd, Middlesboro, KY 40965
0.14
$233,200
Studio
-
3,240
Off Market
209 S 19th St, Middlesboro, KY 40965
0.17
$215,000
3
2
1,352
For Sale
119 S 20th St, Middlesboro, KY 40965
0.15
$250,000
2
2
1,750
For Sale
200 Colonial Hts, Middlesboro, KY 40965
0.17
$2,750,000
99
58
50,352
Recently Sold
Brush Mountain Cir #36, Middlesboro, KY 40965
0.16
$128,600
Studio
-
200
Off Market
717 Highway 441, Middlesboro, KY 40965
0.16
$295,000
5
3
2,100
For Sale
117 Winchester Ave, Middlesboro, KY 40965
0.22
-
-
-
-
Off Market
401 S 20th St, Middlesboro, KY 40965
0.22
$93,400
3
2
920
Off Market
215 S 21st St, Middlesboro, KY 40965
0.22
$120,000
5
4
2,844
For Sale
114 E Rochester Ave, Middlesboro, KY 40965
0.27
$157,300
3
1
1,066
Off Market
415 S 21st St, Middlesboro, KY 40965
0.28
-
3
2
1,750
Off Market

Local Information

  • Map ViewExplore the area around 217 E Chester Ave.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1910
1,584 sqft
$77/sqft

About this House

This single-family home is located at 217 E Chester Ave, Middlesboro, KY. 217 E Chester Ave is in Middlesboro, KY and in ZIP code 40965. This property has 2 bathrooms and approximately 1,584 sqft of floor space. This property has a lot size of 5793 sqft and was built in 1910.
217 E Chester Ave, Middlesboro, KY 40965 is a studio, 2 bathroom, 1,584 sqft single-family home built in 1910. It last sold for $48,000 on Mar 17, 2009. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $122,000, with a rent estimate of $1,538/month.

Home Details for 217 E Chester Ave

Interior Features

Heating & Cooling
Heating: GasAir ConditioningCooling System: CentralHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2

Exterior Features

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

Property Information

Year Built
Year Built: 1910
Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 5793 sqft

Price and Tax history

DateEventPrice
Mar 17, 2009
Source: N/A
Sold
$48,000

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 217 E Chester Ave

  • What is 217 E Chester Ave estimated to be worth?
    Trulia's estimated value for 217 E Chester Ave in Middlesboro, KY is $122,000.
  • What is the price history for 217 E Chester Ave?
    217 E Chester Ave in Middlesboro, KY last sold for $48,000 in March 2009.
  • 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.
  • Does 217 E Chester Ave have air conditioning?
    Yes, 217 E Chester Ave in Middlesboro, KY has air conditioning.
  • How big is the lot at 217 E Chester Ave?
    The lot at 217 E Chester Ave in Middlesboro, KY is about 0.13 acres (5,793 sq ft).

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