205 George Ann Dr, Middlesboro, KY 40965
OFF MARKET

$236,900

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,512 sqft

205 George Ann Dr, Middlesboro, KY 40965

Est. Refi. Payment $1,491/mo*
Refinance Your Home
Currently Off Market - Sold Aug 31, 2011 for $145,000

Home Value

Trulia Estimate
$237K
Since last month
Decreased$4K (-1.7%)
Since last year
Increased$10K (+4.5%)
Since last sale
Increased$92K (+63.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +53% in the last 10 years
MonthEstimated value
2026
September 2026$237K
August 2026$241K
July 2026$244K
June 2026$249K
May 2026$244K
April 2026$242K
March 2026$234K
February 2026$232K
January 2026$227K
2025
2024
2023
2020
2019
2018
2017
2016

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
106 S 38th St, Middlesboro, KY
0.19
Single-Family Home
$180,000
10/21/25
3
2
1,404
203 George Ann Dr, Middlesboro, KY
0.02
Single-Family Home
$256,000
04/24/26
3
2
1,792
115 George Ann Dr, Middlesboro, KY
0.03
Single-Family Home
$271,500
12/16/25
3
2
2,008
1807 Winchester Ave, Middlesboro, KY
0.31
Single-Family Home
$152,500
07/21/26
3
1
1,104
409 Meadow Ln, Middlesboro, KY
0.46
Single-Family Home
$168,000
04/22/26
4
1.5
1,120
140 Chasteen Dr, Middlesboro, KY
0.50
Single-Family Home
$202,000
02/17/26
3
2
1,800
4605 Cumberland Ave, Middlesboro, KY
0.55
Single-Family Home
$170,000
06/04/26
3
2
1,056
3008 Highway 441, Middlesboro, KY
0.73
Single-Family Home
$168,700
01/21/26
3
1.5
1,800
1720 Exeter Ave, Middlesboro, KY
0.39
Single-Family Home
$85,000
09/10/26
2
1
1,456
834 S 31st St, Middlesboro, KY
0.80
Single-Family Home
$82,369
11/17/25
3
2
1,490

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
115 George Ann Dr, Middlesboro, KY 40965
0.03
$271,500
3
2
2,008
Recently Sold
114 George Ann Dr, Middlesboro, KY 40965
0.11
$294,100
4
2
1,796
Off Market
3806 W Cumberland Ave, Middlesboro, KY 40965
0.10
$154,300
3
1
1,120
Off Market
3806 Cumberland Dr, Middlesboro, KY 40965
0.10
$169,500
3
1
1,120
Off Market
3800 W Cumberland Ave, Middlesboro, KY 40965
0.11
$208,300
3
1.5
1,624
Off Market
106 S 38th St, Middlesboro, KY 40965
0.19
$182,500
3
2
1,404
Off Market
1807 Winchester Ave, Middlesboro, KY 40965
0.31
$152,500
3
1
1,104
Recently Sold
2002 Winchester Ave, Middlesboro, KY 40965
0.32
$135,000
2
1
1,120
For Sale
1813 Winchester Ave, Middlesboro, KY 40965
0.35
$66,000
2
1
1,008
Off Market
2103 Winchester Ave, Middlesboro, KY 40965
0.37
$212,300
3
1
2,100
Off Market
1720 Exeter Ave, Middlesboro, KY 40965
0.39
$85,000
2
1
1,456
Recently Sold
2107 Winchester Ave, Middlesboro, KY 40965
0.39
$29,000
-
-
-
For Sale

Local Information

  • Map ViewExplore the area around 205 George Ann Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1968
1,512 sqft
$157/sqft
Garage

About this House

This single-family home is located at 205 George Ann Dr, Middlesboro, KY. 205 George Ann Dr is in Middlesboro, KY and in ZIP code 40965. This property has 3 bedrooms, 2 bathrooms and approximately 1,512 sqft of floor space. This property has a lot size of 9234 sqft and was built in 1968.
205 George Ann Dr, Middlesboro, KY 40965 is a 3 bedroom, 2 bathroom, 1,512 sqft single-family home built in 1968. It last sold for $145,000 on Aug 31, 2011. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $236,900, with a rent estimate of $1,561/month.

Home Details for 205 George Ann Dr

Interior Features

Heating & Cooling
Heating: GasAir ConditioningCooling System: CentralHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 1
Fireplace & Spa
Fireplace

Exterior Features

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

Property Information

Year Built
Year Built: 1968
Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 9234 sqft

Price and Tax history

DateEventPrice
Aug 31, 2011
Source: N/A
Sold
$145,000

Market trends in Middlesboro

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
47
2MoM

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. "
    3
    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. "
    2
    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

Frequently asked questions about 205 George Ann Dr

  • What is 205 George Ann Dr estimated to be worth?
    Trulia's estimated value for 205 George Ann Dr in Middlesboro, KY is $236,900.
  • What is the price history for 205 George Ann Dr?
    205 George Ann Dr in Middlesboro, KY last sold for $145,000 in August 2011.
  • Is Middlesboro a buyer's or seller's market?
    Middlesboro is currently a balanced 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.
  • Does 205 George Ann Dr have air conditioning?
    Yes, 205 George Ann Dr in Middlesboro, KY has air conditioning.
  • How big is the lot at 205 George Ann Dr?
    The lot at 205 George Ann Dr in Middlesboro, KY is about 0.21 acres (9,234 sq ft).

Apartments for Rent

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