1705 Winchester Ave, Middlesboro, KY 40965
OFF MARKET

1705 Winchester Ave
Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 1,344 sqft

$114,100

Trulia Estimate
as of May 11, 2026
Est. Refi. Payment $698/mo*
Refinance Your Home

$114,100

Trulia Estimate
as of May 11, 2026
Est. Refi. Payment $698/mo*
Refinance Your Home
3 Beds
1 Bath
1,344 sqft

Homes for sale near 1705 Winchester Ave

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Apartments for Rent

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Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

This single-family home is located at 1705 Winchester Ave, Middlesboro, KY. 1705 Winchester Ave is in Middlesboro, KY and in ZIP code 40965. This property has 3 bedrooms, 1 bathroom and approximately 1,344 sqft of floor space. This property has a lot size of 7535 sqft and was built in 1923.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 1705 Winchester Ave

Interior Features

Interior Details
BasementNumber of Rooms: 6
Heating & Cooling
Heating: GasHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 1

Exterior Features

Exterior Home Features
Roof: CompositionExterior: OtherFoundation Type: Concrete Block
Parking & Garage
GarageParking: Garage Attached, Off Street

Property Information

Year Built
Year Built: 1923
Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 7535 sqft

Price History for 1705 Winchester Ave

DatePriceEventSource
07/01/2002$65,000Sold
N/A
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Property Tax and Assessment

Year2024
Tax$937
Assessment$90,000
Home facts updated by county records

Comparable Sales for 1705 Winchester Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1809 Exeter Ave, Middlesboro, KY
0.13
Single-Family Home
$40,000
07/30/25
3
1
1,064
1813 Winchester Ave, Middlesboro, KY
0.09
Single-Family Home
$65,000
07/29/25
2
1
1,008
600 38th St, Middlesboro, KY
0.23
Single-Family Home
$90,000
07/15/25
2
1
1,040
409 Meadow Ln, Middlesboro, KY
0.09
Single-Family Home
$168,000
04/22/26
4
1.5
1,120
106 S 38th St, Middlesboro, KY
0.24
Single-Family Home
$180,000
10/21/25
3
2
1,404
3202 W Cumberland Ave, Middlesboro, KY
0.42
Single-Family Home
$107,500
07/31/25
3
2
2,044
140 Chasteen Dr, Middlesboro, KY
0.23
Single-Family Home
$202,000
02/17/26
3
2
1,800
921 Winchester Ave, Middlesboro, KY
0.67
Single-Family Home
$105,000
04/17/26
3
2
1,344
925 Winchester Ave, Middlesboro, KY
0.65
Single-Family Home
$95,000
04/17/26
3
2
1,056
164 Walker Ln, Middlesboro, KY
0.50
Single-Family Home
$176,500
02/11/26
3
1.5
1,040

Assigned Schools

These are the assigned schools for 1705 Winchester 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

  • 79 % Say there's holiday spirit

  • 71 % Say kids play outside

  • 68 % 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

  • 45 % 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

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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Homes for rent near 1705 Winchester Ave

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Off Market Homes Near 1705 Winchester Ave

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1705 Winchester Ave, Middlesboro, KY 40965 is a 3 bedroom, 1 bathroom, 1,344 sqft single-family home built in 1923. This property is not currently available for sale. 1705 Winchester Ave was last sold on Jul 1, 2002 for $65,000. The current Trulia Estimate for 1705 Winchester Ave is $114,100.