1705 Winchester Ave, Middlesboro, KY 40965
OFF MARKET

1705 Winchester Ave
Middlesboro, KY 40965

  • 3 Beds
  • 1 Bath
  • 1,344 sqft

$127,800

Trulia Estimate
as of Aug 9, 2026

$127,800

Trulia Estimate
as of Aug 9, 2026
3 Beds
1 Bath
1,344 sqft

Local Information

  • Map ViewExplore the area around 1705 Winchester 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
1923
Living Area
1,344 sqft
Price/Sqft
$95
Parking
Garage

About this House

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.
1705 Winchester Ave, Middlesboro, KY 40965 is a 3 bedroom, 1 bathroom, 1,344 sqft single-family home built in 1923. It last sold for $65,000 on Jul 1, 2002. It is currently off market. The Trulia Estimate is $127,800, with a rent estimate of $1,461/month.

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

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$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
1807 Winchester Ave, Middlesboro, KY
0.08
Single-Family Home
$152,500
07/21/26
3
1
1,104
1720 Exeter Ave, Middlesboro, KY
0.06
Single-Family Home
$84,000
04/30/26
2
1
1,456
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
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
923 Winchester Ave, Middlesboro, KY
0.65
Single-Family Home
$70,000
07/08/26
1
1
800
164 Walker Ln, Middlesboro, KY
0.50
Single-Family Home
$176,500
02/11/26
3
1.5
1,040
203 George Ann Dr, Middlesboro, KY
0.39
Single-Family Home
$256,000
04/24/26
3
2
1,792

Nearby homes

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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

  • 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

LGBTQ Local Legal Protections

Apartments for Rent

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Homes for sale near 1705 Winchester Ave

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Off Market Homes Near 1705 Winchester Ave

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Frequently asked questions about 1705 Winchester Ave

  • What is 1705 Winchester Ave estimated to be worth?
    Trulia's estimated value for 1705 Winchester Ave in Middlesboro, KY is $127,800.
  • What is the price history for 1705 Winchester Ave?
    1705 Winchester Ave in Middlesboro, KY last sold for $65,000 in July 2002.
  • Is Middlesboro a buyer's or seller's market?
    Middlesboro is currently a buyer's market, based on recent for-sale activity.
  • 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 recently sold homes in Middlesboro, KY.
  • How big is the lot at 1705 Winchester Ave?
    The lot at 1705 Winchester Ave in Middlesboro, KY is about 0.17 acres (7,535 sq ft).
  • Does 1705 Winchester Ave have a garage?
    Yes, 1705 Winchester Ave in Middlesboro, KY has a garage.