Welcome to this versatile 3-bedroom, 2-bathroom home offering 1,296 sq. ft. of living space in a convenient Middlesboro location. With a new roof and a freshly painted exterior, this property is move-in ready and full of potential.
Step inside to find a layout that offers both comfort and flexibility. The home features multiple kitchens and laundry areas, creating the unique opportunity to easily convert the property into two rental units or maintain it as a single-family residence with extra convenience.
The outside is just as impressive, with a spacious fenced backyard, perfect for gatherings, pets, or a garden. You'll also appreciate ample off-street parking, seasonal mountain views, and plenty of storage space throughout.
Located close to schools, shopping, and town amenities, this property combines practicality with investment potential. Whether you're looking for a family home or an income-producing opportunity, 252 Chasteen Drive is a must-see!
For sale
Price cut: $9K (5/14)
$99,999
252 Chasteen Dr, Middlesboro, KY 40965
3beds
1,296sqft
Single Family Residence
Built in 1948
7,840 Square Feet Lot
$-- Zestimate®
$77/sqft
$-- HOA
What's special
Freshly painted exteriorNew roofPlenty of storage spaceSeasonal mountain viewsMultiple kitchensAmple off-street parkingLaundry areas
- 293 days |
- 313 |
- 14 |
Zillow last checked:
Listing updated:
Listed by:
Aaron Rose 423-300-8531,
Realty Network, Inc
Source: East Tennessee Realtors,MLS#: 1316842
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Rooms
- Room types: Bonus Room
Heating
- Central, Natural Gas
Cooling
- Central Air, Ceiling Fan(s)
Appliances
- Included: Range
Features
- Eat-in Kitchen, Bonus Room
- Flooring: Laminate, Carpet, Vinyl
- Windows: Insulated Windows, Aluminum Frames
- Basement: Crawl Space
- Has fireplace: No
- Fireplace features: None
Interior area
- Total structure area: 1,296
- Total interior livable area: 1,296 sqft
Property
Parking
- Parking features: Off Street, Designated Parking
Features
- Has view: Yes
- View description: Mountain(s)
Lot
- Size: 7,840 Square Feet
- Features: Level
Details
- Additional structures: Storage
- Parcel number: 0583300049.00
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Traditional
- Property subtype: Single Family Residence
Materials
- Vinyl Siding, Frame
Condition
- Year built: 1948
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Location
- Region: Middlesboro
Financial & listing details
- Price per square foot: $77/sqft
- Tax assessed value: $90,500
- Annual tax amount: $942
- Date on market: 9/28/2025
- Listing terms: New Loan,Cash,Conventional
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 5/14/2026 | Price change | $99,999-8.3%$77/sqft |
Source:  East Tennessee Realtors #1316842 Report a problem | ||
| 12/10/2025 | Price change | $109,000-5.2%$84/sqft |
Source: East Tennessee Realtors #1316842 Report a problem | ||
| 10/22/2025 | Price change | $115,000-3.4%$89/sqft |
Source: East Tennessee Realtors #1316842 Report a problem | ||
| 9/28/2025 | Listed for sale | $119,000$92/sqft |
Source: East Tennessee Realtors #1316842 Report a problem | ||
| 8/7/2025 | Listing removed | $119,000$92/sqft |
Source: East Tennessee Realtors #1241257 Report a problem | ||
| 5/18/2025 | Price change | $119,000+13.3%$92/sqft |
Source: East Tennessee Realtors #1241257 Report a problem | ||
| 3/18/2025 | Listed for sale | $105,000$81/sqft |
Source: East Tennessee Realtors #1241257 Report a problem | ||
| 3/13/2025 | Pending sale | $105,000$81/sqft |
Source: East Tennessee Realtors #1241257 Report a problem | ||
| 1/13/2025 | Price change | $105,000-3.7%$81/sqft |
Source: East Tennessee Realtors #1241257 Report a problem | ||
| 9/26/2024 | Listed for sale | $109,000$84/sqft |
Source: East Tennessee Realtors #1241257 Report a problem | ||
| 8/30/2024 | Pending sale | $109,000$84/sqft |
Source: East Tennessee Realtors #1241257 Report a problem | ||
| 6/4/2024 | Listed for sale | $109,000$84/sqft |
Source: East Tennessee Realtors #1241257 Report a problem | ||
| 5/16/2024 | Pending sale | $109,000$84/sqft |
Source: East Tennessee Realtors #1241257 Report a problem | ||
| 1/30/2024 | Price change | $109,000-5.2%$84/sqft |
Source: East Tennessee Realtors #1241257 Report a problem | ||
| 9/29/2023 | Listed for sale | $115,000-3.4%$89/sqft |
Source: East Tennessee Realtors #1241257 Report a problem | ||
| 9/24/2023 | Listing removed | -- |
Source:  Imagine MLS #23009694 Report a problem | ||
| 4/22/2023 | Listed for sale | $119,000$92/sqft |
Source: East Tennessee Realtors #1221656 Report a problem | ||
| 4/19/2023 | Pending sale | $119,000$92/sqft |
Source: East Tennessee Realtors #1221656 Report a problem | ||
| 3/23/2023 | Listed for sale | $119,000+260.6%$92/sqft |
Source: East Tennessee Realtors #1221656 Report a problem | ||
| 4/13/2018 | Sold | $33,000+10%$25/sqft |
Source: East Tennessee Realtors #1019970 Report a problem | ||
| 10/19/2006 | Sold | $30,000$23/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $942 -0.6% | $90,500 |
| 2023 | $948 +171.9% | $90,500 +174.2% |
| 2022 | $348 -1% | $33,000 |
| 2021 | $352 -0.3% | $33,000 |
| 2020 | $353 -0.1% | $33,000 |
| 2019 | $353 +18% | $33,000 +10% |
| 2018 | $299 | $30,000 |
| 2017 | -- | $30,000 |
| 2016 | -- | $30,000 |
| 2014 | $275 +1520% | $30,000 |
| 2011 | $17 -85.1% | $30,000 |
| 2010 | $114 | $30,000 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.Climate risks
Neighborhood: 40965
Nearby schools
GreatSchools rating
- 5/10Middlesboro Elementary SchoolGrades: PK-4Distance: 0.6 mi
- 5/10Middlesboro Middle SchoolGrades: 5-8Distance: 0.6 mi
- 6/10Middlesboro High SchoolGrades: 9-12Distance: 0.8 mi
- $31,0002 bd1 ba1.3k sqft251 Chasteen Dr, Middlesboro, KY 40965Off Market
- $24,0002 bd1 ba576 sqft254 Chasteen Dr, Middlesboro, KY 40965Off Market
- $83,900-- bd-- ba840 sqft250 Chasteen Dr, Middlesboro, KY 40965Off Market
- $115,7003 bd1 ba1.8k sqft133 Chasteen Dr, Middlesboro, KY 40965Off Market
- $137,2005 bd2 ba1.4k sqft249 Chasteen Dr, Middlesboro, KY 40965Off Market
- $70,3002 bd1 ba768 sqft137 Chasteen Dr, Middlesboro, KY 40965Off Market
- $71,100-- bd-- ba952 sqft131 Chasteen Dr, Middlesboro, KY 40965Off Market
- $109,0002 bd1 ba1.4k sqft256 Chasteen Dr, Middlesboro, KY 40965Off Market
A local agent can set up tours, give advice and negotiate with sellers.
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