Cherokee Dr, Middlesboro, KY 40965
OFF MARKET

Cherokee Dr
Middlesboro, KY 40965

  • Studio
  • 3 Baths
  • 2,837 sqft

$369,700

Trulia Estimate
as of Aug 14, 2026
Est. Refi. Payment $2,186/mo*
Refinance Your Home

$369,700

Trulia Estimate
as of Aug 14, 2026
Est. Refi. Payment $2,186/mo*
Refinance Your Home
Studio
3 Baths
2,837 sqft

Home Value

Trulia Estimate
$370K
Since last month
Decreased$9K (-2.3%)
Since last year
Increased$26K (+7.6%)
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 +29% in the last 10 years
MonthEstimated value
2026
August 2026$367K
July 2026$361K
June 2026$376K
May 2026$367K
April 2026$357K
March 2026$357K
February 2026$358K
January 2026$345K
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
805 Worchester Ave, Middlesboro, KY
0.46
Single-Family Home
$324,900
04/17/26
5
3
2,250
810 Worchester Ave, Middlesboro, KY
0.43
Single-Family Home
$222,500
05/22/26
3
3
2,000
2824 W Cumberland Ave, Middlesboro, KY
0.72
Single-Family Home
$390,000
08/27/25
4
2.5
2,500
515 N 25th St, Middlesboro, KY
0.44
Single-Family Home
$196,000
11/26/25
3
1
2,000
708 Ilchester Ave, Middlesboro, KY
0.51
Single-Family Home
$175,000
01/13/26
3
2
1,312
2702 W Cumberland Ave, Middlesboro, KY
0.72
Single-Family Home
$350,000
04/24/26
4
2
3,211
2920 W Cumberland Ave, Middlesboro, KY
0.74
Single-Family Home
$120,000
06/12/26
3
3.5
2,214
2410 Cumberland Ave, Middlesboro, KY
0.77
Single-Family Home
$250,000
07/09/26
2
3,076
35th St, Middlesboro, KY
0.80
Single-Family Home
$310,000
04/02/26
3
3
1,836
103 Leafwood Rd, Middlesboro, KY
0.59
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
Distance
Price
Bed
Bath
Sqft
Status
17 Cherokee Dr, Middlesboro, KY 40965
0.03
$284,900
4
3
3,500
Off Market
164 Hendrickson Hill Cemetery Rd, Middlesboro, KY 40965
0.07
$274,600
3
2
1,904
Off Market
103 Kingsbury Woods Rd, Middlesboro, KY 40965
0.12
$369,000
3
3
3,397
For Sale
811 Cherokee Dr, Middlesboro, KY 40965
0.19
$204,300
3
2
1,644
Off Market
806 Cirencester Ave, Middlesboro, KY 40965
0.22
$264,500
3
2
1,572
Off Market
609 Elmwood Rd, Middlesboro, KY 40965
0.24
$288,800
4
3
3,808
Off Market
605 Elmwood Dr, Middlesboro, KY 40965
0.26
$199,500
3
1.5
1,306
Off Market
422 Sherwood Rd, Middlesboro, KY 40965
0.28
$69,100
2
1
1,136
Off Market
125 Cawood Ln, Middlesboro, KY 40965
0.30
$142,500
2
2
1,400
For Sale
109 Hollywood Dr, Middlesboro, KY 40965
0.29
$275,000
3
2.5
3,544
Recently Sold
832 N 25th St, Middlesboro, KY 40965
0.31
$305,000
6
3.5
4,033
Recently Sold
999-25 London Hwy, Corbin, KY 40701
0.32
-
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around Cherokee Dr.
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1966
Living Area
2,837 sqft
Price/Sqft
$130
Parking
Garage

About this House

This single-family home is located at Cherokee Dr, Middlesboro, KY. Cherokee Dr is in Middlesboro, KY and in ZIP code 40965. This property has 3 bathrooms and approximately 2,837 sqft of floor space. This property was built in 1966.
Cherokee Dr, Middlesboro, KY 40965 is a studio, 3 bathroom, 2,837 sqft single-family home built in 1966. It is currently off market. The Trulia Estimate is $369,700, with a rent estimate of $2,110/month.

Home Details for Cherokee Dr

Interior Features

Heating & Cooling
Heating: GasAir ConditioningCooling System: CentralHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 1
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: CompositionFoundation Type: Concrete
Parking & Garage
GarageParking: Garage Attached, Off Street

Property Information

Year Built
Year Built: 1966
Property Type / Style
Property Type: Single Family HomeArchitecture: A-frame

Price and Tax history

YearProperty taxTax assessment
2024
$2,502
$286,700
Home facts updated by county records

Market trends in Middlesboro

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
49
2MoM
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Around this home

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.
    "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

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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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Frequently asked questions about Cherokee Dr

  • What is Cherokee Dr estimated to be worth?
    Trulia's estimated value for Cherokee Dr in Middlesboro, KY is $369,700.
  • 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 Cherokee Dr?
    The closest schools to Cherokee Dr 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).
  • Does Cherokee Dr have air conditioning?
    Yes, Cherokee Dr in Middlesboro, KY has air conditioning.
  • Does Cherokee Dr have a garage?
    Yes, Cherokee Dr in Middlesboro, KY has a garage.