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

OFF MARKET

Gloucester, Middlesboro, KY 40965

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
27 North St, Middlesboro, KY	0.01	Single-Family Home	$65,000	05/15/26		-	960
441 Ky Lick Fork Rd, Middlesboro, KY	0.01	Single-Family Home	$18,000	07/21/26		-	-
112 Bell Rd, Middlesboro, KY	0.09	Single-Family Home	$65,000	02/03/26		1	770
103 Bellwood Rd, Middlesboro, KY	0.16	Single-Family Home	$13,600	08/10/26	3	1	862
105 Nutwood Rd, Middlesboro, KY	0.24	Single-Family Home	$15,000	10/01/26	3	1	728
199 Bellwood Rd, Middlesboro, KY	0.25	Single-Family Home	$20,100	08/06/26		-	-
215 Ellenwood Rd, Middlesboro, KY	0.26	Single-Family Home	$4,200	07/23/26		-	-
103 Nutwood Rd, Middlesboro, KY	0.27	Single-Family Home	$17,000	07/24/26	2	1	1,244
103 Nutwood Rd, Middlesboro, KY	0.27	Single-Family Home	$80,000	10/26/26		2	1,664
103 Leafwood Rd, Middlesboro, KY	0.37	Single-Family Home	$164,000	02/21/26	2	2	1,326

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.

Address	Price	Bed	Bath	Sqft	Status
126 Chasteen Ln, Middlesboro, KY 40965	-	3	1	845	Off Market
Noetown Rd, Middlesboro, KY 40965	-	Studio	1	936	Off Market
217 Ky Devils Gdn, Middlesboro, KY 40965	-	Studio	-	1,120	Off Market
3486 Ky Old Rdg, Middlesboro, KY 40965	-	Studio	-	600	Off Market
441 Key, Middlesboro, KY 40965	-	Studio	-	-	Off Market
131 Deb & Poe Smith Ln, Middlesboro, KY 40965	-	Studio	1	1,042	Off Market
441 Ky Lick Frk, Middlesboro, KY 40965	$261,000	Studio	-	-	Off Market
217 Ky Groundhog Holw, Middlesboro, KY 40965	-	Studio	-	-	Off Market
3486 Ky Cannon Ck Rd, Middlesboro, KY 40965	-	Studio	-	-	Off Market
102 Martinwood Rd, Middlesboro, KY 40965	$98,600	3	2	1,250	Off Market
Chester Ave, Middlesboro, KY 40965	-	Studio	-	-	Off Market
Brush Mountain Farms #1, Middlesboro, KY 40965	-	Studio	-	-	Off Market
1534 Page Cutoff, Middlesboro, KY 40965	-	Studio	-	-	Off Market
Abbey Ln, Middlesboro, KY 40965	-	-	-	-	Off Market
Winchester Ave, Middlesboro, KY 40965	-	-	-	-	Off Market
25 E US Hwy, Middlesboro, KY 40965	$169,000	Studio	-	-	Off Market
Venado Dr, Middlesboro, KY 40965	-	-	-	-	Off Market
206 High Point Rd, Middlesboro, KY 40965	-	-	-	-	Off Market
4804 Cumblerland Ave, Middlesboro, KY 40965	-	-	-	-	Off Market
69 Route 2, Middlesboro, KY 40965	-	-	-	-	Off Market

Homes for rent near Gloucester

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Local Information

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

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About this House

Gloucester is in Middlesboro, KY and in ZIP code 40965.

Gloucester, Middlesboro, KY 40965 is a unknown. This property is not currently displayed as for sale or rent on Trulia.

Home Details for Gloucester

Property Information
Property Type / Style Property Type: Unknown

Additional Cost

Market trends in Middlesboro

Last updated September 2026

Avg. sale price

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Sale-to-List Price

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Price per sq ft

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Available listings

7MoM

Sourced by Trulia Market Trends

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
9y 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. "
3
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. "
2
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
13y ago
"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.
16y 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
Flag

LGBTQ Local Legal Protections

Apartments for Rent

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Contact for price
1-2 bd
1-2 ba
370 S 13th St #f320a52c6,
Middlesboro, KY 40965
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Middlesboro
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Off Market Homes Near Gloucester

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SOLD
NOV 3, 2026
$53,000
2 bd
1.5 ba
1,426 sqft
123 Cawood Ln,
Middlesboro, KY 40965
Mountain Realty
SOLD
NOV 3, 2026
$65,000
2 bd
1 ba
910 sqft
310 Barkley Dr,
Middlesboro, KY 40965
REMAX PROFESSIONAL'S
SOLD
OCT 28, 2026
$142,000
2 bd
1 ba
792 sqft
815 Dorchester Ave,
Middlesboro, KY 40965
Backwoods Realty & Development
SOLD
OCT 26, 2026
$144,000
1 ba
1,228 sqft
814 Dorchester Ave,
Middlesboro, KY 40965
SOLD
OCT 26, 2026
$80,000
2 ba
1,664 sqft
103 Nutwood Rd,
Middlesboro, KY 40965
SOLD
OCT 23, 2026
$80,000
4 bd
2 ba
1,664 sqft
120 Redwood Rd #A & B,
Middlesboro, KY 40965
Black Diamond Realty, Imagine MLS
SOLD
OCT 21, 2026
$69,000
1,224 sqft
32 Abbey Ct,
Middlesboro, KY 40965
SOLD
OCT 21, 2026
$32,500
US Highway 25e Vista Venado Sub,
Middlesboro, KY 40965
SOLD
OCT 14, 2026
$40,000
1,236 sqft
104 Alpine Rd,
Middlesboro, KY 40965
SOLD
OCT 14, 2026
$32,500
103 Does Xing,
Middlesboro, KY 40965
Century 21 Virginia Wilder Real Estate
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Homes for sale near Gloucester

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0.85 ACRES
$469,900
3 bd
2.5 ba
3,258 sqft
225 Sherwood Rd,
Middlesboro, KY 40965
Mountain Realty Group LLC, Imagine MLS
0.5 ACRES
$320,000
5 bd
3 ba
3,000 sqft
103 Sherwood Rd,
Middlesboro, KY 40965
Realty Group
0.4 ACRES
$135,000
2 bd
2 ba
1,400 sqft
125 Cawood Ln,
Middlesboro, KY 40965
Realty Group
0.75 ACRES
$279,000
3 bd
3 ba
2,210 sqft
515 Englewood Rd,
Middlesboro, KY 40965
Backwoods Realty & Development
NEW - 4 HRS AGO
0.35 ACRES
$320,000
4 bd
2.5 ba
2,053 sqft
802 Cirencester Ave,
Middlesboro, KY 40965
REMAX PROFESSIONAL'S
0.26 ACRES
$234,900
3 bd
2 ba
2,191 sqft
508 Worchester Ave,
Middlesboro, KY 40965
Mountain Realty Group LLC, Imagine MLS
$105,900
3 bd
2 ba
1,966 sqft
412 N 24th St,
Middlesboro, KY 40965
Turn Key Realty, Imagine MLS
0.41 ACRES
$285,000
3 bd
1.5 ba
2,400 sqft
406 N 25th St,
Middlesboro, KY 40965
Realty Group
0.45 ACRES
$264,900
5 bd
2.5 ba
3,068 sqft
207 Arthur Hts,
Middlesboro, KY 40965
Coldwell Banker Bisceglia Realty & Auction Co, Imagine MLS
0.76 ACRES
$200,000
3 bd
1.5 ba
2,154 sqft
116 Edgewood Rd,
Middlesboro, KY 40965
Black Diamond Realty, Imagine MLS
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