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, 79% 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, 68% 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, 45% 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

FOR SALE

1.69 ACRES

321 E Chester Ave
Middlesboro, KY 40965

$275,000

$299,000

Est. Mortgage $1,617/mo*

Get Pre-Qualified

$275,000

$299,000

Est. Mortgage $1,617/mo*

Get Pre-Qualified

(on 1.69 acres)

Local Information

-- mins to

Commute Destination

Description

1.695 flat acres in the city of Middlesboro. Zoned B3 (Central Business District). Some uses permitted are: Wholesale & Retail Trade, Sporting Goods, Banks, Theater, Auto Repair, Pharmacy, Hotel-Motel, Bed & Breakfast, and Multi Family

Home Highlights

Parking

No Info

Outdoor

No Info

HOA

None

Price/Sqft

No Info

Listed

180+ days ago

Home Details for 321 E Chester Ave

Interior Features
Appliances & Utilities Utilities: Electricity Available, Natural Gas Available, Sewer Available, Water Available

Exterior Features
Surface & Elevation Topography: Level, Cleared

Days on Market
Days on Market: 180+

Property Information
Property Type / Style Property Type: LandProperty Subtype: Unimproved Land
Property Information Usage of Home: ResidentialParcel Number: 0694409002.00, 0694409007.00

Price & Status
Price List Price: $275,000

Active Status
MLS Status: Active

Location
Direction & Address City: MiddlesboroCommunity: City Limits

Agent Information
Listing Agent Listing ID: 25012296

Lot Information
Lot Area: 1.69 Acres

Miscellaneous
Mls Number: 25012296

Last check for updates: about 1 hour ago

Listing courtesy of Kevin Bisceglia, (606) 269-7970

Coldwell Banker Bisceglia Realty & Auction Co

Source: Imagine MLS, MLS#25012296

Also Listed on East Tennessee Realtors, Imagine MLS, East Tennessee Realtors.

Price History for 321 E Chester Ave

Date	Price	Event	Source
05/07/2026	$275,000	PriceChange	East Tennessee Realtors #1304132
Price Change $24,000 (-8%)
03/27/2026	$299,000	PriceChange	East Tennessee Realtors #1304132
Price Change $50,900 (-15%)
06/10/2025	$349,900	Listed For Sale	East Tennessee Realtors #1304132

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Comparable Sales for 321 E Chester Ave

Address	Distance	Property Type	Sold Price	Sold Date	Bath	Sqft
Lot 6 Bellwood Rd, Middlesboro, KY	1.42	Lot/Land	$13,000	09/25/25	-	-
423 N 10th St, Middlesboro, KY	1.25	Lot/Land	$1,250,000	09/05/25	-	-
Lot 1 Bellwood Rd, Middlesboro, KY	1.53	Lot/Land	$10,000	10/17/25	-	-
Lot 2 Bellwood Rd, Middlesboro, KY	1.53	Lot/Land	$22,500	10/17/25	-	-
Arie Turner Ln, Middlesboro, KY	2.21	Lot/Land	$26,000	11/26/25	-	-
19 Venado Dr, Middlesboro, KY	2.30	Lot/Land	$40,000	05/30/25	-	-
305 Doe Xing, Middlesboro, KY	2.53	Lot/Land	$265,500	01/23/26	-	-
Windermere Dr, Middlesboro, KY	2.83	Lot/Land	$32,500	03/19/26	-	-
LOT Tractd Hillcrest Dr, Cumberland Gap, TN	3.01	Lot/Land	$35,000	12/11/25	-	-

Assigned Schools

These are the assigned schools for 321 E Chester Ave.

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
79 % Say there's holiday spirit
71 % Say kids play outside
68 % 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
45 % 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

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
6y 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
7y 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
7y 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
7y 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
Flag
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
Flag

LGBTQ Local Legal Protections

Additional Cost

Kevin Bisceglia, Coldwell Banker Bisceglia Realty & Auction Co

Agent Phone: (606) 269-7970

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

321 E Chester Ave, Middlesboro, KY 40965 is a lot/land. This property is currently available for sale and was listed by Imagine MLS on Jun 10, 2025. The MLS # for this home is MLS# 25012296.

321 E Chester Ave
Middlesboro, KY 40965

$275,000

$275,000

Local Information