Is a car needed in Middlesboro, KY?

As of early 2026, 93% of users say car is needed

Are yards well-kept in Middlesboro, KY?

As of early 2026, 87% of users say yards are well-kept

Is parking easy in Middlesboro, KY?

As of early 2026, 81% of users say parking is easy

Does Middlesboro, KY show holiday spirit?

As of early 2026, 77% of users say there's holiday spirit

Do kids play outside in Middlesboro, KY?

As of early 2026, 71% of users say kids play outside

Is Middlesboro, KY dog-friendly?

As of early 2026, 69% of users say it's dog friendly

Do residents of Middlesboro, KY plan to stay at least 5 years?

As of early 2026, 61% of users say they plan to stay for at least 5 years

Is there wildlife in Middlesboro, KY?

As of early 2026, 58% of users say there's wildlife

Are neighbors friendly in Middlesboro, KY?

As of early 2026, 54% of users say neighbors are friendly

Would people walk alone at night in Middlesboro, KY?

As of early 2026, 52% of users say people would walk alone at night

Is Middlesboro, KY quiet?

As of early 2026, 49% of users say it's quiet

Does Middlesboro, KY have sidewalks?

As of early 2026, 44% of users say there are sidewalks

Is Middlesboro, KY walkable to restaurants?

As of early 2026, 40% of users say it's walkable to restaurants

Are the streets well-lit in Middlesboro, KY?

As of early 2026, 37% of users say streets are well-lit

Are there community events in Middlesboro, KY?

As of early 2026, 28% of users say there are community events

Is Middlesboro, KY walkable to grocery stores?

As of early 2026, 27% of users say it's walkable to grocery stores

What is the price history for 107 Cherry St?

107 Cherry St in Middlesboro, KY last sold for $15,000 in August 2008.

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 .

What are the closest schools to 107 Cherry St?

The closest schools to 107 Cherry St 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).

How big is the lot at 107 Cherry St?

The lot at 107 Cherry St in Middlesboro, KY is about 0.11 acres (5,009 sq ft).

OFF MARKET

$15,000

Last sold price

Studio
1 Bath
864 sqft

107 Cherry St, Middlesboro, KY 40965

Currently Off Market - Sold Aug 6, 2008 for $15,000

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

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
102 Cherry St, Vine Grove, KY	0.04	Single-Family Home	$149,500	07/20/26	2	1	920
103 Bellwood Rd, Middlesboro, KY	0.29	Single-Family Home	$13,600	08/10/26	3	1	862
103 Nutwood Rd, Middlesboro, KY	0.60	Single-Family Home	$17,000	07/24/26	2	1	1,244
112 Bell Rd, Middlesboro, KY	0.30	Single-Family Home	$65,000	02/03/26		1	770
134 Barkley Dr, Middlesboro, KY	0.45	Single-Family Home	$70,000	09/11/25	3	2	1,296
305 N 15th St, Middlesboro, KY	1.12	Single-Family Home	$50,000	11/03/25	2	1	876
428 Wilderness Rd, Middlesboro, KY	0.83	Single-Family Home	$147,000	10/27/25	3	1	1,320
307 Englewood Rd, Middlesboro, KY	1.03	Single-Family Home	$3,000	03/05/26		2	1,072
63 Old Pineville Pike, Middlesboro, KY	0.47	Single-Family Home	$145,000	08/17/26	3	2	1,560
714 Dorchester Ave, Middlesboro, KY	1.18	Single-Family Home	$175,000	03/03/26	3	1	1,000

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
102 Cherry St, Vine Grove, KY 40175	0.04	$149,500	2	1	920	Recently Sold
111 Cherry St, Middlesboro, KY 40965	0.03	-	-	-	-	Off Market
114 Willow St, Middlesboro, KY 40965	0.06	$81,400	2	1	904	Off Market
116 Willow St, Middlesboro, KY 40965	0.07	$81,400	2	1	904	Off Market
1323 N 25th St, Middlesboro, KY 40965	0.13	$134,200	3	2	2,000	Off Market
1315 N 25th St, Middlesboro, KY 40965	0.22	$75,000	3	1	960	Off Market
101 Kim Ln, Middlesboro, KY 40965	0.34	$411,000	5	4	3,874	Off Market
Abbey Ln, Middlesboro, KY 40965	0.37	-	-	-	-	Off Market
Winchester Ave, Middlesboro, KY 40965	0.37	-	-	-	-	Off Market
431 Bellwood Rd, Middlesboro, KY 40965	0.38	$146,000	3	2	1,848	Off Market
63 Old Pineville Pike, Middlesboro, KY 40965	0.47	$145,000	3	2	1,560	Recently Sold
223/225 Bratley Dr, Middlesboro, KY 40965	0.46	-	-	-	-	Off Market

Local Information

Map ViewExplore the area around 107 Cherry St.
Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

1923

Living Area

864 sqft

Parking

None

About this House

This single-family home is located at 107 Cherry St, Middlesboro, KY. 107 Cherry St is in Middlesboro, KY and in ZIP code 40965. This property has 1 bathroom and approximately 864 sqft of floor space. This property has a lot size of 5009 sqft and was built in 1923.

107 Cherry St, Middlesboro, KY 40965 is a studio, 1 bathroom, 864 sqft single-family home built in 1923. It last sold for $15,000 on Aug 6, 2008. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate rent is $1,255/month.

Home Details for 107 Cherry St

Interior Features
Levels, Entrance, & Accessibility Stories: 1
Interior Details Number of Rooms: 4

Exterior Features
Exterior Home Features Roof: MetalFoundation Type: Piers
Parking & Garage Parking: None

Property Information
Year Built Year Built: 1923
Property Type / Style Property Type: Single Family Home

Lot Information
Lot Area: 5009 sqft

Price and Tax history

Date	Event	Price
Aug 6, 2008 Source: N/A	Sold	$15,000

Year	Property tax	Tax assessment
2024	$52	$5,000

Additional Cost

Market trends in Middlesboro

Last updated July 2026

Avg. sale price

—

Sale-to-List Price

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Price per sq ft

—

Available listings

2MoM

Around this home

Middlesboro Elementary School
PK-4
Public
499 Students
Middlesboro Independent School District
5/10
GreatSchools Rating
Parent Rating Average
This school does not want to deal with parents, so they make it to where parents cannot get involved. They schedule parent teacher conferences in the hours of you work you cannot attend. They also only give notice a few days in advance so requesting time off work in order to attend is impossible. If you do get to attend you speak to the teacher for a total of 5minutes before you are forced out. Policies are constantly changing and of course parents are never made aware of the changes.
Parent Review
8y ago
2 Reviews

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
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.
Resident
6y ago
"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
Resident
7y ago
"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.
Resident
8y ago
"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.
Resident
8y ago
"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.
Resident
8y ago
"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
12y ago
"I live here and this is a beautiful neighborhood, quit, within walking distance to everything in town, just a nice area"
0
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Laura K.
15y ago
"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
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LGBTQ Local Legal Protections

Frequently asked questions about 107 Cherry St

What is the price history for 107 Cherry St?
107 Cherry St in Middlesboro, KY last sold for $15,000 in August 2008.
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.
What are the closest schools to 107 Cherry St?
The closest schools to 107 Cherry St 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).
How big is the lot at 107 Cherry St?
The lot at 107 Cherry St in Middlesboro, KY is about 0.11 acres (5,009 sq ft).