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

$230,700

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,296 sqft (on 0.32 acres)

218 Windermere Dr, Middlesboro, KY 40965

Est. Refi. Payment $1,446/mo*
Refinance Your Home
Currently Off Market - Sold Aug 8, 2025 for $225,000

Home Value

Trulia Estimate
$231K
Since last month
Increased$600 (+0.3%)
Since last year
Increased$5K (+2%)
Since last sale
Increased$5K (+2.3%)
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
September 2026$230K
August 2026$231K
July 2026$230K
June 2026$233K
May 2026$231K
April 2026$231K
March 2026$230K
February 2026$227K
January 2026$227K
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
0.35
Single-Family Home
$240,000
01/30/26
3
2.5
1,692
23 Castleford Way, Middlesboro, KY
0.58
Single-Family Home
$183,500
07/17/26
3
1.5
1,080
314 Picadilly Ct, Middlesboro, KY
0.24
Single-Family Home
$293,000
02/06/26
4
2.5
2,576
5 Abbey Ln, Middlesboro, KY
0.77
Single-Family Home
$239,500
11/19/25
3
2
1,221
11 Castleford Way, Middlesboro, KY
0.58
Single-Family Home
$189,500
05/20/26
3
1
1,100
6 Hampton Ct, Middlesboro, KY
0.64
Single-Family Home
$250,000
03/04/26
4
3
1,966
1425 Highway 441, Middlesboro, KY
1.11
Single-Family Home
$155,000
07/27/26
3
1.5
1,242
63 Old Pineville Pike, Middlesboro, KY
1.66
Single-Family Home
$145,000
08/17/26
3
2
1,560
3008 Highway 441, Middlesboro, KY
1.99
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
238 Windermere Dr, Middlesboro, KY 40965
0.24
$294,400
3
2
1,603
Off Market
314 Picadilly Ct, Middlesboro, KY 40965
0.24
$293,000
4
2.5
2,576
Recently Sold
156 Wellington Dr, Middlesboro, KY 40965
0.26
$230,000
3
1.5
1,320
For Sale
Windermere Dr, Middlesboro, KY 40965
0.28
$32,500
-
-
-
Recently Sold
230 Windermere Dr, Middlesboro, KY 40965
0.30
$257,300
3
2
2,099
Off Market
150 Wellington Dr, Middlesboro, KY 40965
0.30
$209,900
3
2
1,140
Off Market
220 Windermere Dr, Middlesboro, KY 40965
0.35
$240,000
3
2.5
1,692
Recently Sold
212 Windermere Dr, Middlesboro, KY 40965
0.36
$229,100
3
2
1,476
Off Market
206 Nottingham Dr, Middlesboro, KY 40965
0.37
$194,800
2
2
1,059
Off Market
140 Wellington Dr, Middlesboro, KY 40965
0.40
$199,900
4
2
1,612
For Sale
118 Wellington Dr, Middlesboro, KY 40965
0.56
$230,500
3
2
1,600
Off Market

Local Information

  • Map ViewExplore the area around 218 Windermere Dr.
  • Schools6 Preschool Schools6 Elementary Schools6 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2002
0.32 acre lot
1,296 sqft
$178/sqft
Garage

About this House

COZY RANCHER NESTLED IN THE HEART OF MIDDLESBORO! This gem is in Ambleside! This cozy rancher has 1296 square feet with lots of storage space. The open floor plan makes family time and entertaining even more enjoyable. The main bedroom has two closets and a custom shower. The extended ceilings add character to this home. There is laminate and Vinyl floors throughout the home, closet space at the end of the hall and entrance way closet for extra storage. The kitchen has updated appliances. There is crown molding throughout the home and cozy gas fireplace in the living room. Enjoy your morning coffee or cuddle on the swing of the large front porch. The beautiful landscaping is added curb appeal to the wonderful ranch home. There is a nice flat backyard with a deck and privacy fence. This home would be a great starter home or just as sweet as a forever home. Call today for a showing.
218 Windermere Dr, Middlesboro, KY 40965 is a 3 bedroom, 2 bathroom, 1,296 sqft single-family home built in 2002. It last sold for $225,000 on Aug 8, 2025 (4% below the $235,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $230,700, with a rent estimate of $1,566/month.
Last check for updates: about 11 hours ago
Listed by Sheila Durham, (606) 499-9029
Coldwell Banker Bisceglia Realty & Auction Co
Bought with: Sheila Durham, (606) 499-9029, Coldwell Banker Bisceglia Realty & Auction Co
Source: Imagine MLS, MLS#25013288

Home Details for 218 Windermere Dr

Interior Features

Interior Details
Basement: Crawl SpaceNumber of Rooms: 8Types of Rooms: Master Bedroom, Bedroom 1, Bedroom 2, Bathroom 1, Bathroom 2, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1296 Square Feet
Appliances & Utilities
Utilities: Electricity Connected, Sewer Connected, Water Connected, Propane ConnectedAppliances: Dishwasher, Refrigerator, RangeDishwasherLaundry: Electric Dryer Hookup,Washer HookupRefrigerator
Heating & Cooling
Heating: Electric,Heat PumpHas CoolingAir Conditioning: Heat PumpHas HeatingHeating Fuel: Electric
Fireplace & Spa
Fireplace: Gas Log, Living Room, VentlessHas a Fireplace
Windows, Doors, Floors & Walls
Window: Insulated Windows, Blinds, ScreensFlooring: Laminate, Vinyl
Levels, Entrance, & Accessibility
Levels: OneFloors: Laminate, Vinyl
View
Has a ViewView: Neighborhood

Exterior Features

Exterior Home Features
Roof: Composition ShinglePatio / Porch: Deck, PorchFencing: WoodOther Structures: Shed(s)Foundation: BlockNo Private Pool
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 1Parking: Attached Garage,Driveway
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1296 Square Feet

Property Information

Year Built
Year Built: 2002
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: HouseArchitecture: Ranch
Building
Construction Materials: Vinyl SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 0681000105.30

Price & Status

Price
List Price: $235,000
Status Change & Dates
Off Market Date: Wed Jul 09 2025Possession Timing: Close Of Escrow

Active Status

MLS Status: Closed

Location

Direction & Address
City: MiddlesboroCommunity: Rural
School Information
Elementary School: Bell CentralJr High / Middle School: Bell CentralHigh School: Bell CoHigh School District: Bell County - 87

Building

Building Area
Building Area: 1296 Square Feet

Community

Community Features: Pool

Lot Information

Lot Area: 0.32 acres

Miscellaneous

Mls Number: 25013288Above Grade Unfinished Area: 1296

Additional Information

Pool

Price and Tax history

DateEventPrice
Aug 8, 2025
Source: Imagine MLS #25013288
Sold
$225,000
Jul 9, 2025
Source: Imagine MLS #25013288
Pending
$235,000
Jul 8, 2025
Source: Imagine MLS #25013288
PriceChange
$235,000
Price decreased by 6%
Jun 21, 2025
Source: Imagine MLS #25013288
Listed For Sale
$249,000
Jun 29, 2021
Source: East Tennessee Realtors #1155021
Sold
$170,000

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. "
    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.

Frequently asked questions about 218 Windermere Dr

  • What is 218 Windermere Dr estimated to be worth?
    Trulia's estimated value for 218 Windermere Dr in Middlesboro, KY is $230,700.
  • What is the price history for 218 Windermere Dr?
    218 Windermere Dr in Middlesboro, KY last sold for $225,000 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 218 Windermere Dr have air conditioning?
    Yes, 218 Windermere Dr in Middlesboro, KY has air conditioning.
  • Does 218 Windermere Dr have a pool?
    Yes, 218 Windermere Dr in Middlesboro, KY has a pool.

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