Cherokee Dr, Middlesboro, KY 40965
OFF MARKET

Cherokee Dr
Middlesboro, KY 40965

  • Studio

$339,500

Trulia Estimate
as of May 27, 2026
Est. Refi. Payment $1,994/mo*
Refinance Your Home

$339,500

Trulia Estimate
as of May 27, 2026
Est. Refi. Payment $1,994/mo*
Refinance Your Home
Studio

Local Information

Map showing home location
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-- mins to
Commute Destination

Description

This single-family home is located at Cherokee Dr, Middlesboro, KY. Cherokee Dr is in Middlesboro, KY and in ZIP code 40965.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
No Info
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for Cherokee Dr

Property Information

Property Type / Style
Property Type: Single Family Home

Price History for Cherokee Dr

DatePriceEventSource
08/28/2006$250,000Sold
N/A
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Property Tax and Assessment

Year2024
Tax$2,603
Assessment$250,000
Home facts updated by county records

Comparable Sales for Cherokee Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
9 Cherokee Dr, Middlesboro, KY
0.02
Single-Family Home
$150,000
02/24/26
2
1,188
109 Hollywood Dr, Middlesboro, KY
0.29
Single-Family Home
$275,000
11/03/25
3
2.5
3,544
832 N 25th St, Middlesboro, KY
0.31
Single-Family Home
$305,000
05/14/26
6
3.5
4,033
806 Manchester Ave, Middlesboro, KY
0.35
Single-Family Home
$186,000
05/28/25
2
2
1,899
840 N 25th St, Middlesboro, KY
0.34
Single-Family Home
$165,000
08/07/25
4
1.5
3,400
810 Worchester Ave, Middlesboro, KY
0.43
Single-Family Home
$222,500
05/22/26
3
3
2,000
515 N 25th St, Middlesboro, KY
0.44
Single-Family Home
$196,000
11/26/25
3
1
2,000
123 Twin Acres Rd, Middlesboro, KY
0.50
Single-Family Home
$272,700
06/13/25
4
2
3,338
805 Worchester Ave, Middlesboro, KY
0.46
Single-Family Home
$324,900
04/17/26
5
3
2,250
101 Kim Ln, Middlesboro, KY
0.47
Single-Family Home
$400,000
06/06/25
5
4
3,874

Nearby homes

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Assigned Schools

These are the assigned schools for Cherokee Dr.
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

  • 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

Apartments for Rent

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Homes for sale near Cherokee Dr

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Off Market Homes Near Cherokee Dr

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Homes for rent near Cherokee Dr

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Cherokee Dr, Middlesboro, KY 40965 is a studio single-family home. This property is not currently available for sale. Cherokee Dr was last sold on Aug 28, 2006 for $250,000. The current Trulia Estimate for Cherokee Dr is $339,500.