2002 Winchester Ave, Middlesboro, KY 40965
Property image
Property image
FOR SALE

$135,000

  • 2 Beds
  • 1 Bath
  • 1,120 sqft

2002 Winchester Ave, Middlesboro, KY 40965

Est. Mortgage $872/mo*
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Home Highlights

Single-Family Home
Built in 1940
$121/sqft
2 Carport Spaces

Local Information

  • Map ViewExplore the area around 2002 Winchester Ave.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

CHARMING 2 BEDROOM/ONE BATH HOME! This charming 2 bedroom, 1 bath home offers a perfect blend of comfort and convenience, completely outside of the flood zone. Enjoy leisurely mornings on the large covered front porch or entertain guest on the back deck overlooking your private fully fenced in yard - perfect for pets or gardening. This move in ready property also features a detached 2 -car carport, providing ample shaded parking and storage. Don't miss this gem, conveniently located close to all the local amenities. Plus only a 10 minutes drive to LMU main campus.
Last check for updates: about 9 hours ago
Listing courtesy of Sheila Durham, (606) 499-9029
Coldwell Banker Bisceglia Realty & Auction Co
Source: Imagine MLS, MLS#26010030
Also Listed on Imagine MLS.

Home Details for 2002 Winchester Ave

Interior Features

Interior Details
Basement: Crawl SpaceNumber of Rooms: 2Types of Rooms: Master Bedroom, Kitchen
Beds & Baths
Number of Bedrooms: 2Number of Bathrooms: 1Number of Bathrooms (full): 1
Dimensions and Layout
Living Area: 1120 Square Feet
Appliances & Utilities
Utilities: Cable Connected, Sewer Connected, Water ConnectedAppliances: Refrigerator, RangeLaundry: Electric Dryer Hookup,Washer HookupRefrigerator
Heating & Cooling
Heating: Electric,Heat PumpHas CoolingAir Conditioning: Central Air,Electric,Heat PumpHas HeatingHeating Fuel: Electric
Fireplace & Spa
No Fireplace
Windows, Doors, Floors & Walls
Window: Insulated Windows, BlindsFlooring: Laminate, Vinyl
Levels, Entrance, & Accessibility
Levels: OneFloors: Laminate, Vinyl
View
Has a ViewView: Mountain(s)

Exterior Features

Exterior Home Features
Roof: MetalFencing: Chain LinkOther Structures: Shed(s)Foundation: BlockNo Private Pool
Parking & Garage
Number of Carport Spaces: 2Number of Covered Spaces: 2Has a CarportNo GarageNo Attached GarageParking Spaces: 2Parking: Detached Carport
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Farm & Range
Not Allowed to Raise Horses
Finished Area
Finished Area (above surface): 1120 Square Feet

Days on Market

Days on Market: 128

Property Information

Year Built
Year Built: 1940
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Shotgun
Building
Construction Materials: Vinyl SidingDoes Not Include Home Warranty
Property Information
Parcel Number: 0574400065.00

Price & Status

Price
List Price: $135,000Price Per Sqft: $121
Status Change & Dates
Possession Timing: Close Of Escrow

Active Status

MLS Status: Active

Location

Direction & Address
City: MiddlesboroCommunity: City Limits
School Information
Elementary School: Middlesboro IndJr High / Middle School: Middlesboro IndHigh School: Middlesboro IndHigh School District: Middlesboro Independent

Agent Information

Listing Agent
Listing ID: 26010030

Building

Building Area
Building Area: 1120 Square Feet

HOA

No HOA

Lot Information

Lot Area: 7501.032 sqft

Miscellaneous

Mls Number: 26010030Above Grade Unfinished Area: 1120

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

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

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

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
1807 Winchester Ave, Middlesboro, KY
0.18
Single-Family Home
$152,500
07/21/26
3
1
1,104
1720 Exeter Ave, Middlesboro, KY
0.20
Single-Family Home
$84,000
04/30/26
2
1
1,456
106 S 38th St, Middlesboro, KY
0.14
Single-Family Home
$180,000
10/21/25
3
2
1,404
409 Meadow Ln, Middlesboro, KY
0.28
Single-Family Home
$168,000
04/22/26
4
1.5
1,120
140 Chasteen Dr, Middlesboro, KY
0.21
Single-Family Home
$202,000
02/17/26
3
2
1,800
923 Winchester Ave, Middlesboro, KY
0.90
Single-Family Home
$70,000
07/08/26
1
1
800

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
2103 Winchester Ave, Middlesboro, KY 40965
0.11
$211,600
3
1
2,100
Off Market
106 S 38th St, Middlesboro, KY 40965
0.14
$184,000
3
2
1,404
Off Market
2107 Winchester Ave, Middlesboro, KY 40965
0.12
$29,000
-
-
-
For Sale
407 S 38th St, Middlesboro, KY 40965
0.15
$132,400
2
1
804
Off Market
1813 Winchester Ave, Middlesboro, KY 40965
0.16
$66,700
2
1
1,008
Off Market
1807 Winchester Ave, Middlesboro, KY 40965
0.18
$152,500
3
1
1,104
Recently Sold
1809 Exeter Ave, Middlesboro, KY 40965
0.17
$41,100
3
1
1,064
Off Market
3800 W Cumberland Ave, Middlesboro, KY 40965
0.21
$205,800
3
1.5
1,624
Off Market
3806 Cumberland Dr, Middlesboro, KY 40965
0.22
$166,600
3
1
1,120
Off Market
3806 W Cumberland Ave, Middlesboro, KY 40965
0.23
$153,800
3
1
1,120
Off Market
114 George Ann Dr, Middlesboro, KY 40965
0.23
$292,700
4
2
1,796
Off Market

Price and Tax history

DateEventPrice
May 6, 2026
Source: Imagine MLS #26010030
Listed For Sale
$135,000
Apr 23, 2007
Source: N/A
Sold
$30,000

LGBTQ Local Legal Protections

Sheila Durham, Coldwell Banker Bisceglia Realty & Auction Co
Agent Phone: (606) 499-9029
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

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Frequently asked questions about 2002 Winchester Ave

  • What is the estimated monthly payment for 2002 Winchester Ave?
    Based on a $135,000 list price with 20% down at today's rates, the estimated monthly payment for 2002 Winchester Ave in Middlesboro, KY is approximately $886 (about $728 principal & interest, $83 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • 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 homes for sale in Middlesboro, KY.
  • What are the closest schools to 2002 Winchester Ave?
    The closest schools to 2002 Winchester Ave 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 2002 Winchester Ave have air conditioning?
    Yes, 2002 Winchester Ave in Middlesboro, KY has air conditioning.
  • Does 2002 Winchester Ave have laundry facilities?
    Yes, 2002 Winchester Ave in Middlesboro, KY has laundry facilities.
  • How big is the lot at 2002 Winchester Ave?
    The lot at 2002 Winchester Ave in Middlesboro, KY is about 0.17 acres (7,501 sq ft).
2002 Winchester Ave, Middlesboro, KY 40965 is a 2 bedroom, 1 bathroom, 1,120 sqft single-family home built in 1940. This property is currently available for sale and was listed by Imagine MLS on May 6, 2026. The MLS # for this home is MLS# 26010030.