808 Cherokee Dr, Middlesboro, KY 40965
Property image
Property image
OFF MARKET

808 Cherokee Dr
Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 1,867 sqft (on 0.32 acres)

$276,700

Trulia Estimate
as of Jul 25, 2026

$276,700

Trulia Estimate
as of Jul 25, 2026
3 Beds
2 Baths
1,867 sqft
(on 0.32 acres)

Local Information

  • Map ViewExplore the area around 808 Cherokee Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1979
Lot Size
0.32 acres
Living Area
1,867 sqft
Price/Sqft
$148
Parking
Garage

About this House

MOTIVATED SELLER!! SELLER SAYS MOVE IT!! THIS HOME IS CLOSE TO THE ONE OF THE OLDEST GOLF COURSE'S . LARGE BRICK HOME IN GREAT SHAPE. 3 BDRM'S, 2 FULL BATHS, NICE FENCED IN YARD. PRICED TO MOVE!!
808 Cherokee Dr, Middlesboro, KY 40965 is a 3 bedroom, 2 bathroom, 1,867 sqft single-family home built in 1979. It last sold for $243,800 on Jan 11, 2023. It is currently off market. The Trulia Estimate is $276,700, with a rent estimate of $1,777/month.

Home Details for 808 Cherokee Dr

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: Central, OtherHeating Fuel: Forced Air
Interior Details
Number of Rooms: 7Types of Rooms: Dining Room, Family Room
Appliances & Utilities
DishwasherDisposalDryerRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Tile, Carpet, Hardwood

Exterior Features

Exterior Home Features
Roof: OtherExterior: Brick
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1979
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Lot Information

Lot Area: 0.32 acres

Price History for 808 Cherokee Dr

DatePriceEventSource
01/11/2023$243,800Sold
East Tennessee Realtors #1203040
11/25/2022$259,500PendingEast Tennessee Realtors #1203040
10/12/2022$259,500PriceChange
East Tennessee Realtors #1203040
09/21/2022$269,000PriceChange
East Tennessee Realtors #1203040
08/22/2022$275,000PriceChange
East Tennessee Realtors #1203040
08/19/2022$280,000Listed For SaleEast Tennessee Realtors #1203040
05/15/2020$155,000Sold
East Tennessee Realtors #1097715
11/20/2019$156,000PendingAgent Provided
09/12/2019$156,000PriceChange
Agent Provided
07/26/2019$164,000PriceChange
Agent Provided
04/29/2019$169,900PriceChange
Agent Provided
02/10/2019$184,900Listed For SaleN/A
06/26/2015$135,000Sold
East Tennessee Realtors #917269
03/18/2015$149,900Listed For SaleAgent Provided

Market trends in Middlesboro

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
51
5MoM
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Comparable Sales for 808 Cherokee Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
810 Worchester Ave, Middlesboro, KY
0.38
Single-Family Home
$222,500
05/22/26
3
3
2,000
515 N 25th St, Middlesboro, KY
0.38
Single-Family Home
$196,000
11/26/25
3
1
2,000
840 N 25th St, Middlesboro, KY
0.28
Single-Family Home
$165,000
08/07/25
4
1.5
3,400
708 Ilchester Ave, Middlesboro, KY
0.45
Single-Family Home
$175,000
01/13/26
3
2
1,312
805 Worchester Ave, Middlesboro, KY
0.41
Single-Family Home
$324,900
04/17/26
5
3
2,250
728 Winchester Ave, Middlesboro, KY
0.83
Single-Family Home
$250,000
09/17/25
3
2
1,505
2702 W Cumberland Ave, Middlesboro, KY
0.66
Single-Family Home
$350,000
04/24/26
4
2
3,211
103 Leafwood Rd, Middlesboro, KY
0.54
Single-Family Home
$164,000
02/21/26
2
2
1,326
707 Gloucester Ave, Middlesboro, KY
0.64
Single-Family Home
$169,900
05/22/26
3
2
1,184
203 George Ann Dr, Middlesboro, KY
1.09
Single-Family Home
$256,000
04/24/26
3
2
1,792

Nearby homes

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Assigned Schools

These are the assigned schools for 808 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

  • 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 808 Cherokee Dr

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Off Market Homes Near 808 Cherokee Dr

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