238 Windermere Dr, Middlesboro, KY 40965
Property image
Property image
OFF MARKET

$296,100

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,603 sqft (on 0.41 acres)

238 Windermere Dr, Middlesboro, KY 40965

Est. Refi. Payment $1,834/mo*
Refinance Your Home
Currently Off Market - Sold Aug 8, 2025 for $265,000

Home Value

Trulia Estimate
$296K
Since last month
Increased$9K (+3.2%)
Since last year
Increased$30K (+11.4%)
Since last sale
Increased$31K (+11.7%)
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 +60% in the last 10 years
MonthEstimated value
2026
August 2026$296K
July 2026$287K
June 2026$295K
May 2026$290K
April 2026$285K
March 2026$281K
February 2026$278K
January 2026$274K
2025
2024
2023
2022
2021
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
220 Windermere Dr, Middlesboro, KY
0.11
Single-Family Home
$240,000
01/30/26
3
2.5
1,692
314 Picadilly Ct, Middlesboro, KY
0.06
Single-Family Home
$293,000
02/06/26
4
2.5
2,576
23 Castleford Way, Middlesboro, KY
0.38
Single-Family Home
$183,500
07/17/26
3
1.5
1,080
5 Abbey Ln, Middlesboro, KY
0.61
Single-Family Home
$239,500
11/19/25
3
2
1,221
11 Castleford Way, Middlesboro, KY
0.41
Single-Family Home
$189,500
05/20/26
3
1
1,100
6 Hampton Ct, Middlesboro, KY
0.46
Single-Family Home
$250,000
03/04/26
4
3
1,966
1425 Highway 441, Middlesboro, KY
0.92
Single-Family Home
$155,000
07/27/26
3
1.5
1,242
63 Old Pineville Pike, Middlesboro, KY
1.43
Single-Family Home
$145,000
08/17/26
3
2
1,560
3008 Highway 441, Middlesboro, KY
1.90
Single-Family Home
$168,700
01/21/26
3
1.5
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
Windermere Dr, Middlesboro, KY 40965
0.05
$32,500
-
-
-
Recently Sold
230 Windermere Dr, Middlesboro, KY 40965
0.06
$257,300
3
2
2,099
Off Market
314 Picadilly Ct, Middlesboro, KY 40965
0.06
$293,000
4
2.5
2,576
Recently Sold
220 Windermere Dr, Middlesboro, KY 40965
0.11
$240,000
3
2.5
1,692
Recently Sold
212 Windermere Dr, Middlesboro, KY 40965
0.14
$229,100
3
2
1,476
Off Market
156 Wellington Dr, Middlesboro, KY 40965
0.16
$230,000
3
1.5
1,320
For Sale
150 Wellington Dr, Middlesboro, KY 40965
0.18
$208,500
3
2
1,140
Off Market
218 Windermere Dr, Middlesboro, KY 40965
0.24
$230,700
3
2
1,296
Off Market
140 Wellington Dr, Middlesboro, KY 40965
0.26
$199,900
4
2
1,612
For Sale
206 Nottingham Dr, Middlesboro, KY 40965
0.27
$194,800
2
2
1,059
Off Market
23 Castleford Way, Middlesboro, KY 40965
0.38
$183,500
3
1.5
1,080
Recently Sold

Local Information

  • Map ViewExplore the area around 238 Windermere Dr.
  • Schools6 Preschool Schools6 Elementary Schools6 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2001
0.41 acre lot
1,603 sqft
$185/sqft
2 Car Garage

About this House

BEATUIFUL AMBLESIDE HOME! This home is nestled in the beautiful Ambleside subdivision with 3 bedrooms and 2 baths. The main living space has a main suite including a walk-in closet, 2 bedrooms, guest bath, kitchen, living room, dining room and laundry room. There are hardwood flooring and carpet throughout the home with vinyl in the kitchen and baths. There is a laundry room on the main floor off from the kitchen with a large pantry. This home has potential for growth with an unfinished upstairs and full size basement. There is a 2 car garage and a large deck in the back with an extra entry to the main bedroom. The house has 1604 square feet on the main floor with an additional 900 square feet upstairs that could be finished for a bonus room or spare bedroom. The basement has an additional 891 square feet ready for storage or additional living space. This home is positioned nicely on a 55X175 lot with an additional building lot separate from the home. This home has all the convenience of single floor living with options. Call today for a showing!
238 Windermere Dr, Middlesboro, KY 40965 is a 3 bedroom, 2 bathroom, 1,603 sqft single-family home built in 2001. It last sold for $265,000 on Aug 8, 2025 (5% below the $279,900 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $296,100, with a rent estimate of $1,774/month.
Last check for updates: about 22 hours ago
Listed by Sheila Durham, (606) 499-9029
Coldwell Banker Bisceglia Real
Bought with: Sheila Durham, (606) 499-9029, Coldwell Banker Bisceglia Real
Source: East Tennessee Realtors, MLS#1303859

Home Details for 238 Windermere Dr

Active Status

MLS Status: Closed

Interior Features

Interior Details
Basement: UnfinishedNumber of Rooms: 8
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1603 Square Feet
Appliances & Utilities
Appliances: Dishwasher, Range, RefrigeratorDishwasherRefrigerator
Heating & Cooling
Heating: Central,Heat Pump,ElectricHas CoolingAir Conditioning: Central Air,Ceiling Fan(s)Has HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: NoneNo Fireplace
Windows, Doors, Floors & Walls
Flooring: Carpet, Hardwood, Vinyl
Levels, Entrance, & Accessibility
Floors: Carpet, Hardwood, Vinyl
View
Has a ViewView: Mountain(s)
Security
Security: Smoke Detector(s)

Exterior Features

Exterior Home Features
No Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Off Street,Attached,Main Level
Water & Sewer
Sewer: Public Sewer

Property Information

Year Built
Year Built: 2001
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Traditional
Building
Construction Materials: BrickNot Attached Property
Property Information
Parcel Number: 0681000105.45

Price & Status

Price
List Price: $279,900
Status Change & Dates
Off Market Date: Fri Jun 20 2025

Media

Location

Direction & Address
City: MiddlesboroCommunity: Ambleside
School Information
Elementary School: Yellow CreekJr High / Middle School: Bell CentralHigh School: Bell County

Building

Building Area
Building Area: 1603 Square Feet

HOA

No HOA

Lot Information

Lot Area: 0.41 acres

Miscellaneous

BasementMls Number: 1303859

Price and Tax history

DateEventPrice
Aug 8, 2025
Source: East Tennessee Realtors #1303859
Sold
$265,000
Jun 21, 2025
Source: East Tennessee Realtors #1303859
Pending
$279,900
Jun 12, 2025
Source: East Tennessee Realtors #1303859
PendingToActive
$279,900
Jun 10, 2025
Source: East Tennessee Realtors #1303859
Pending
$279,900
Jun 7, 2025
Source: East Tennessee Realtors #1303859
Listed For Sale
$279,900

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. "
    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

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.
Listing Information presented by local MLS brokerage: Zillow, Inc., local broker - Eric Young - (865) 378-5282.

Frequently asked questions about 238 Windermere Dr

  • What is 238 Windermere Dr estimated to be worth?
    Trulia's estimated value for 238 Windermere Dr in Middlesboro, KY is $296,100.
  • What is the price history for 238 Windermere Dr?
    238 Windermere Dr in Middlesboro, KY last sold for $265,000 in August 2025.
  • 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 238 Windermere Dr have air conditioning?
    Yes, 238 Windermere Dr in Middlesboro, KY has air conditioning.
  • How big is the lot at 238 Windermere Dr?
    The lot at 238 Windermere Dr in Middlesboro, KY is about 0.41 acres (17,860 sq ft).

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