400 Gloucester Ave, Middlesboro, KY 40965
Property image
Property image
OFF MARKET

400 Gloucester Ave
Middlesboro, KY 40965

  • 4 Beds
  • 2 Baths
  • 2,032 sqft

$249,500

Trulia Estimate
as of Jul 27, 2026
Est. Refi. Payment $1,514/mo*
Refinance Your Home

$249,500

Trulia Estimate
as of Jul 27, 2026
Est. Refi. Payment $1,514/mo*
Refinance Your Home
4 Beds
2 Baths
2,032 sqft

Local Information

  • Map ViewExplore the area around 400 Gloucester Ave.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1930
Living Area
2,032 sqft
Price/Sqft
$123
Parking
Garage

About this House

There are so many things to love about this charming four-bedroom, two bath red brick home! It is tucked in the back of a quiet neighborhood, but close enough to walk to downtown for town gatherings and activities. Mature trees surround this home, and the large yard is wonderful for running and playing, and the outdoor/patio area in the back is perfect for your grill. The rustic slate tiled entryway invites you and your guests into a home that has a mix of old-world character paired with modern luxuries. The spacious living room has original hardwood floors, a fireplace, built-in bookshelves, and a bright sunroom w/french doors. The recently updated kitchen features stainless steel appliances, butcher block countertops, subway tile backsplash, custom cabinetry, and plenty of room to
400 Gloucester Ave, Middlesboro, KY 40965 is a 4 bedroom, 2 bathroom, 2,032 sqft single-family home built in 1930. It last sold for $178,000 on Jul 21, 2020. It is currently off market. The Trulia Estimate is $249,500, with a rent estimate of $1,652/month.

Home Details for 400 Gloucester Ave

Interior Features

Heating & Cooling
Heating: Heat Pump, ElectricAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Appliances & Utilities
Refrigerator

Exterior Features

Exterior Home Features
Roof: CompositionExterior: BrickFoundation Type: Concrete Block
Parking & Garage
GarageParking Space: 1Parking: Garage Attached

Property Information

Year Built
Year Built: 1930
Property Type / Style
Property Type: Single Family Home

Price History for 400 Gloucester Ave

DatePriceEventSource
07/21/2020$178,000Sold
East Tennessee Realtors #1109596
06/06/2020$179,900PendingAgent Provided
05/22/2020$179,900PriceChange
Agent Provided
03/16/2020$184,900PriceChange
Agent Provided
03/02/2020$189,000Listed For SaleAgent Provided
10/16/2017$178,100Sold
Imagine MLS #3026035
05/08/2017$189,000ListingRemovedAgent Provided
03/24/2017$189,000Listed For SaleAgent Provided
05/02/2014$140,000Sold
East Tennessee Realtors #875420

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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Property Tax and Assessment

Year2024
Tax$1,853
Assessment$178,000
Home facts updated by county records

Comparable Sales for 400 Gloucester Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
414 N 24th St, Middlesboro, KY
0.38
Single-Family Home
$167,000
09/15/25
4
2
1,600
707 Gloucester Ave, Middlesboro, KY
0.27
Single-Family Home
$169,900
05/22/26
3
2
1,184
708 Ilchester Ave, Middlesboro, KY
0.32
Single-Family Home
$175,000
01/13/26
3
2
1,312
919 W Rochester Ave, Middlesboro, KY
0.62
Single-Family Home
$167,000
09/15/25
4
2
2,024
515 N 25th St, Middlesboro, KY
0.32
Single-Family Home
$196,000
11/26/25
3
1
2,000
728 Winchester Ave, Middlesboro, KY
0.38
Single-Family Home
$250,000
09/17/25
3
2
1,505
2702 W Cumberland Ave, Middlesboro, KY
0.33
Single-Family Home
$350,000
04/24/26
4
2
3,211
840 N 25th St, Middlesboro, KY
0.51
Single-Family Home
$165,000
08/07/25
4
1.5
3,400
810 Worchester Ave, Middlesboro, KY
0.42
Single-Family Home
$222,500
05/22/26
3
3
2,000
114 W Rochester Ave, Middlesboro, KY
0.44
Single-Family Home
$175,000
12/31/25
3
2
1,008

Nearby homes

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Assigned Schools

These are the assigned schools for 400 Gloucester Ave.
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 400 Gloucester Ave

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Off Market Homes Near 400 Gloucester Ave

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