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

230 Windermere Dr
Middlesboro, KY 40965

  • 3 Beds
  • 2 Baths
  • 2,099 sqft (on 0.50 acres)

$256,300

Trulia Estimate
as of Aug 7, 2026

$256,300

Trulia Estimate
as of Aug 7, 2026
3 Beds
2 Baths
2,099 sqft
(on 0.50 acres)

Local Information

  • Map ViewExplore the area around 230 Windermere Dr.
  • Schools6 Preschool Schools6 Elementary Schools6 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2007
Lot Size
0.5 acres
Living Area
2,099 sqft
Price/Sqft
$122
Parking
Garage

About this House

Three bedroom, two bath well maintained home in beautiful Ambleside Subdivision. Living room and kitchen/dining room combo. Hardwood floors, covered porch and attached 2 car garage. All three bedrooms and the bathrooms are on the main level with a bonus room upstairs that could be used as a fourth bedroom or office. Don't wait on this one, they never last long .
230 Windermere Dr, Middlesboro, KY 40965 is a 3 bedroom, 2 bathroom, 2,099 sqft single-family home built in 2007. It last sold for $250,000 on May 5, 2025 (7% below the $270,000 asking price). It is currently off market. The Trulia Estimate is $256,300, with a rent estimate of $1,847/month.

Home Details for 230 Windermere Dr

Interior Features

Interior Details
Basement: Crawl SpaceNumber of Rooms: 7
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 2099 Square Feet
Appliances & Utilities
Appliances: Dishwasher, Range, RefrigeratorDishwasherRefrigerator
Heating & Cooling
Heating: Heat Pump,ElectricHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
Fireplace: NoneNo Fireplace
Windows, Doors, Floors & Walls
Window: Insulated WindowsFlooring: Carpet, Hardwood, Vinyl
Levels, Entrance, & Accessibility
Floors: Carpet, Hardwood, Vinyl
View
Has a ViewView: Mountain(s)

Exterior Features

Exterior Home Features
No Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageParking Spaces: 2Parking: Garage
Water & Sewer
Sewer: Public Sewer

Property Information

Year Built
Year Built: 2007
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Contemporary
Building
Construction Materials: Vinyl Siding, BrickNot Attached Property
Property Information
Parcel Number: 0681000105.41

Price & Status

Price
List Price: $270,000
Status Change & Dates
Off Market Date: Thu Jan 30 2025

Active Status

MLS Status: Closed

Location

Direction & Address
City: MiddlesboroCommunity: Ambleside

Building

Building Area
Building Area: 2099 Square Feet

Lot Information

Lot Area: 0.50 acres

Miscellaneous

Mls Number: 1271144
Last check for updates: about 13 hours ago
Listed by Mike Hensley, (606) 269-1737
REMAX PROFESSIONAL'S
Bought with: Mike Hensley, (606) 269-1737, REMAX PROFESSIONAL'S
Source: East Tennessee Realtors, MLS#1271144

Price History for 230 Windermere Dr

DatePriceEventSource
05/05/2025$250,000Sold
East Tennessee Realtors #1271144
01/30/2025$270,000PendingEast Tennessee Realtors #1271144
10/15/2024$270,000PriceChange
East Tennessee Realtors #1271144
09/30/2024$275,000PriceChange
East Tennessee Realtors #1271144
08/23/2024$280,000PriceChange
East Tennessee Realtors #1271144
08/09/2024$285,000PriceChange
East Tennessee Realtors #1271144
07/27/2024$290,000Listed For SaleEast Tennessee Realtors #1271144
08/01/2022$222,000Sold
East Tennessee Realtors #1196519
06/26/2022$239,900PendingEast Tennessee Realtors #1196519
06/23/2022$239,900Listed For SaleRE/MAX International #1196519
11/17/2014$158,500Sold
East Tennessee Realtors #888493

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
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2024
Tax$2,566
Assessment$222,000
Home facts updated by county records

Comparable Sales for 230 Windermere Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
238 Windermere Dr, Middlesboro, KY
0.06
Single-Family Home
$265,000
08/08/25
3
2
1,603
220 Windermere Dr, Middlesboro, KY
0.08
Single-Family Home
$240,000
01/30/26
3
2.5
1,692
314 Picadilly Ct, Middlesboro, KY
0.11
Single-Family Home
$293,000
02/06/26
4
2.5
2,576
218 Windermere Dr, Middlesboro, KY
0.30
Single-Family Home
$225,000
08/08/25
3
2
1,296
6 Hampton Ct, Middlesboro, KY
0.44
Single-Family Home
$250,000
03/04/26
4
3
1,966
23 Castleford Way, Middlesboro, KY
0.36
Single-Family Home
$183,500
07/17/26
3
1.5
1,080
206 Nottingham Dr, Middlesboro, KY
0.30
Single-Family Home
$190,000
08/21/25
2
2
1,059
10 Thaxted Ln, Middlesboro, KY
0.79
Single-Family Home
$280,000
08/29/25
3
2
2,096
5 Abbey Ln, Middlesboro, KY
0.61
Single-Family Home
$239,500
11/19/25
3
2
1,221
11 Castleford Way, Middlesboro, KY
0.40
Single-Family Home
$189,500
05/20/26
3
1
1,100

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 230 Windermere Dr.
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

Skip to last item
Skip to first item

Homes for sale near 230 Windermere Dr

Skip to last item
Skip to first item

Off Market Homes Near 230 Windermere Dr

Skip to last item
Skip to first item
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.