561 Sherwood Rd, Middlesboro, KY 40965
OFF MARKET

$158,500

Trulia Estimate
  • Studio

561 Sherwood Rd, Middlesboro, KY 40965

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Home Value

Trulia Estimate
$159K
Since last month
Increased$11K (+7.7%)
Since last year
Increased$34K (+27%)
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 +35% in the last 10 years
MonthEstimated value
2026
October 2026$159K
September 2026$204K
August 2026$147K
February 2026$131K
January 2026$165K
2025
2024
2023
2022
2021
2020

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
9 Cherokee Dr, Middlesboro, KY
0.20
Single-Family Home
$150,000
02/24/26
2
1,188
109 Hollywood Dr, Middlesboro, KY
0.24
Single-Family Home
$275,000
11/03/25
3
2.5
3,544
103 Bellwood Rd, Middlesboro, KY
0.31
Single-Family Home
$13,600
08/10/26
3
1
862
Bellwood Rd, Middlesboro, KY
0.33
Single-Family Home
$22,500
10/29/25
-
-
Bellwood Rd, Middlesboro, KY
0.33
Single-Family Home
$10,000
10/17/25
-
-
112 Bell Rd, Middlesboro, KY
0.35
Single-Family Home
$65,000
02/03/26
1
770
27 North St, Middlesboro, KY
0.35
Single-Family Home
$65,000
05/15/26
-
960
441 Ky Lick Fork Rd, Middlesboro, KY
0.35
Single-Family Home
$18,000
07/21/26
-
-
832 N 25th St, Middlesboro, KY
0.36
Single-Family Home
$305,000
05/14/26
6
3.5
4,033
105 Nutwood Rd, Middlesboro, KY
0.49
Single-Family Home
$15,000
10/01/26
3
1
728

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
561 Sherwood Rd, Middlesboro, KY 40965
0.00
$435,900
5
3
4,168
Off Market
102 Laurelwood Rd, Middlesboro, KY 40965
0.04
-
Studio
-
-
Off Market
102 Laurelwood Rd, Middlesboro, KY 40965
0.04
$197,100
Studio
2
1,800
Off Market
102 Laurelwood Rd, Middlesboro, KY 40965
0.04
$158,500
Studio
-
-
Off Market
102 Laurelwood Rd, Middlesboro, KY 40965
0.04
$194,200
Studio
2
3,149
Off Market
102 Laurelwood Rd, Middlesboro, KY 40965
0.04
$104,500
Studio
1
1,064
Off Market
830 Cherokee Dr, Middlesboro, KY 40965
0.07
-
Studio
3
2,837
Off Market
159 Hopper Rd, Middlesboro, KY 40965
0.09
$174,500
3
1
2,016
Off Market
422 Sherwood Rd, Middlesboro, KY 40965
0.10
$68,200
2
1
1,136
Off Market
305 Englewood Rd #1, Middlesboro, KY 40965
0.11
-
2
1
-
Off Market
305 Englewood Rd #4, Middlesboro, KY 40965
0.11
-
2
1
-
Off Market
305 Englewood Rd #3, Middlesboro, KY 40965
0.11
$137,800
8
4
2,750
Off Market
420 Sherwood Rd, Middlesboro, KY 40965
0.12
$87,200
3
1
1,344
Off Market
602 Sherwood Rd, Middlesboro, KY 40965
0.12
$141,500
Studio
-
1,680
Off Market
355 Sherwood Rd, Middlesboro, KY 40965
0.12
-
Studio
-
1,070
Off Market
108 Cawood Ln, Middlesboro, KY 40965
0.13
$89,600
2
1.5
1,134
Off Market
125 Cawood Ln, Middlesboro, KY 40965
0.13
$135,000
2
2
1,400
For Sale
109 Cawood Ln, Middlesboro, KY 40965
0.14
-
2
1
900
Off Market
354 Sherwood Rd, Middlesboro, KY 40965
0.14
$151,900
3
2
1,610
Off Market
13 Cherokee Dr, Middlesboro, KY 40965
0.14
$227,200
Studio
2
1,596
Off Market

Local Information

  • Map ViewExplore the area around 561 Sherwood Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home

About this House

This single-family home is located at 561 Sherwood Rd, Middlesboro, KY. 561 Sherwood Rd is in Middlesboro, KY and in ZIP code 40965.
561 Sherwood Rd, Middlesboro, KY 40965 is a studio single-family home. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $158,500, with a rent estimate of $1,449/month.

Home Details for 561 Sherwood Rd

Property Information

Property Type / Style
Property Type: Single Family Home

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

This October

Trick-or-Treat Score

Built from what locals say about this neighborhood.
  • 77% say there's holiday spirit
  • 54% say neighbors are friendly
  • 44% say there are sidewalks
Trulia Trick or TreatStart Ghost Hunt
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. "
    3
    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. "
    2
    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 561 Sherwood Rd

  • What is 561 Sherwood Rd estimated to be worth?
    Trulia's estimated value for 561 Sherwood Rd in Middlesboro, KY is $158,500.
  • 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.
  • What are the closest schools to 561 Sherwood Rd?
    The closest schools to 561 Sherwood Rd in Middlesboro, KY are Middlesboro Elementary School (Pre-K, rated 5/10), Middlesboro High School (rated 6/10), Middlesboro Middle School (Elementary, rated 5/10).

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