400 Gloucester Ave, Middlesboro, KY, 40965
About This Home
Nestled in the heart of downtown Middlesboro, this beautifully maintained 1930 home offers over 2,000 square feet of comfortable living space with 4 bedrooms and 2 full baths. The updated kitchen is designed for both style and functionality, featuring custom soft-close cabinetry, under-cabinet lighting, a double oven, and a French-door refrigerator with double freezer drawers. This kitchen also has a fill-pot feature next to the stove. The kitchen's backdown is where you will , find a covered deck—perfect for entertaining family and friends. Situated on a quiet dead-end street, this property combines the convenience of downtown living with the privacy and tranquility you've been looking for. The home offers a flexible floor plan with two bedrooms on the main level with cedar lined closets and two bedrooms upstairs. The foyer entryway offers a closet and space for coats and shoes to conveniently stored. A spacious living room with a fireplace creates a warm gathering space, while the formal dining room and vented sunroom provide additional areas for relaxation and entertaining. The basement includes a two-car garage, workshop, and ample storage space, offering plenty of room for hobbies and organization. Schedule an appointment TODAY!
Getting Around
Car-Dependent
Very Limited Transit
BikeableSchools
Construction
Condition
- Year built: 1930
Materials
- Foundation: Block,Concrete Perimeter
- Roof: Composition,Dimensional Style,Shingle
- Construction materials: Brick Veneer
Type & Style
- Home type: SingleFamily
- Architectural style: Mid-Century Modern
- Property subType: Single Family Residence
Interior
Appliances
- Appliances included: Disposal,Double Oven,Dishwasher,Refrigerator,Range
- Laundry features: Electric Dryer Hookup,Washer Hookup
Basement
- Has basement: Yes
- Basement: Full,Unfinished
Bathroom1
- Level: First
Bedroom2
- Level: First
Bedrooms & Bathrooms
- Bedrooms: 4
- Bathrooms: 2
- Full bathrooms: 2
Dining Room
- Level: First
Features
- Entrance Foyer
- Window features: Blinds
- Flooring: Carpet,Hardwood,Slate
- Number of fireplaces: 1
- Fireplace features: Living Room
- Fireplace: Yes
- Finished area below ground: 0
- Finished area above ground: 2,032
Foyer
- Level: First
Heating & Cooling
- Heating features: Electric,Heat Pump
- Cooling features: Electric,Heat Pump
Interior Area
- Total structure area: 2,032
- Total interior livable area: 2,032 sqft
Kitchen
- Level: First
Living Room
- Level: First
Master Bedroom
- Level: First
Utility Room
- Level: Lower
Property
Details
- Parcel number: 0694114005.00
Features
- Levels: One and One Half
- Exterior features: Other
- Fencing: None
- Has view: Yes
- View description: Mountain(s)
Lot
- Lot size: 0.48 Acres
- Features: Other,Many Trees
Parking
- Total spaces: 2
- Parking features: Attached Garage,Basement,Garage Door Opener,Off Street
- Has garage: Yes
- Attached garage spaces: 2
- Covered spaces: 2
- Has uncovered spaces: Yes
Climate Risk is Financial Risk
Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.
Biggest Threats for This Home
- Inland Flooding
- Cold Wave
- Strong Wind
- Winter Weather
- Hail
- Tornado
How This Home’s Risks Compare
FEMA Declared Disasters Across Kentucky Counties
Understanding the Costs
Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.
Estimated Costs Today
| Monthly | Annual | |
|---|---|---|
| Mortgage | $1,511 | $18,132 |
| Home Insurance * | $201 | $2,412 |
| Property Taxes | $265 | $3,180 |
| Electricity | $160 | $1,925 |
| Total | $2,137 | $25,644 |
Income You'd Need if You Spent...
Kentucky FAIR Plan Programs
How Costs Could Change Over Time
Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.
Comparing Against the Market
Price Per Sq Ft
vs Other Active Listings
Avg $/sqft
vs Homes Sold Last Month
Median $/sqft
Current Market Trends
Median Price Per Square Foot
The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.
Historicals for This Listing
Zestimate History ($/sqft)
Price History
| Date | Event | Price |
|---|---|---|
| 2026-07-31 | Listed for sale | $299,000 |
| 2020-07-21 | Sold | $178,000 |
| 2020-06-06 | Pending sale | $179,900 |
| 2020-05-22 | Price change | $179,900 |
| 2020-03-16 | Price change | $184,900 |
| 2020-03-02 | Listed for sale | $189,000 |
| 2017-10-16 | Sold | $178,100 |
| 2017-05-08 | Listing removed | $189,000 |
| 2017-03-24 | Listed for sale | $189,000 |
| 2014-05-02 | Sold | $140,000 |
For Sale by Agent
View on Zillow