Windermere Dr, Middlesboro, KY 40965
SOLD
MAR 19, 2026

Windermere Dr
Middlesboro, KY 40965

    $32,500

    Last Sold: Mar 19, 2026
    19% below list $40K
    Est. Refi. Payment $257/mo*
    Refinance Your Home

    $32,500

    Last Sold: Mar 19, 2026
    19% below list $40K
    Est. Refi. Payment $257/mo*
    Refinance Your Home
    (on 0.67 acres)

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    Local Information

    Map showing home location
    © Google
    -- mins to
    Commute Destination

    Description

    Here is your chance to own land in AMBLESIDE!! I heard a rumor they aren't making any more! 2 lots listed together for $40k or seller is willing to separate the property for qualified, serious buyers.
    Seller is willing to have property cleared for buyer.

    In county with city sewer and water!
    This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from March 28, 2026

    Home Highlights

    Parking
    No Info
    Outdoor
    No Info
    HOA
    None
    Price/Sqft
    No Info
    Listed
    114 days ago

    Home Details for Windermere Dr

    Interior Features

    Appliances & Utilities
    Utilities: Cable TV
    View
    Has a ViewView: Country Setting

    Exterior Features

    Exterior Home Features
    No Private Pool
    Parking & Garage
    No Carport

    Property Information

    Property Type / Style
    Property Type: LandProperty Subtype: Land
    Property Information
    Parcel Number: .

    Price & Status

    Price
    List Price: $40,000
    Status Change & Dates
    Off Market Date: Tue Feb 24 2026

    Active Status

    MLS Status: Closed

    Location

    Direction & Address
    City: MiddlesboroCommunity: Ambleside

    Lot Information

    Lot Area: 0.67 acres

    Offer

    Listing Terms: Cash, Conventional, New Loan

    Miscellaneous

    Mls Number: 1326396

    Additional Information

    HOA Amenities: Other
    Last check for updates: about 3 hours ago
    Listed by Misti McGrath, (606) 670-1838
    Realty Group
    Bought with: Misti McGrath, (606) 670-1838, Realty Group
    Source: East Tennessee Realtors, MLS#1326396

    Price History for Windermere Dr

    DatePriceEventSource
    03/19/2026$32,500Sold
    East Tennessee Realtors #1326396
    02/24/2026$40,000PendingEast Tennessee Realtors #1326396
    01/14/2026$40,000Listed For SaleEast Tennessee Realtors #1326396
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    Comparable Sales for Windermere Dr

    Address
    Distance
    Property Type
    Sold Price
    Sold Date
    Bed
    Bath
    Sqft
    Lot 2 Bellwood Rd, Middlesboro, KY
    1.32
    Lot/Land
    $22,500
    10/17/25
    -
    -
    Lot 6 Bellwood Rd, Middlesboro, KY
    1.42
    Lot/Land
    $13,000
    09/25/25
    -
    -
    Lot 1 Bellwood Rd, Middlesboro, KY
    1.32
    Lot/Land
    $10,000
    10/17/25
    -
    -
    Arie Turner Ln, Middlesboro, KY
    2.64
    Lot/Land
    $26,000
    11/26/25
    -
    -
    19 Venado Dr, Middlesboro, KY
    2.74
    Lot/Land
    $40,000
    05/30/25
    -
    -
    305 Doe Xing, Middlesboro, KY
    2.52
    Lot/Land
    $265,500
    01/23/26
    -
    -
    423 N 10th St, Middlesboro, KY
    2.74
    Lot/Land
    $1,250,000
    09/05/25
    -
    -
    LOT Tractd Hillcrest Dr, Cumberland Gap, TN
    4.96
    Lot/Land
    $35,000
    12/11/25
    -
    -

    Assigned Schools

    These are the assigned schools for 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

    • 79 % Say there's holiday spirit

    • 71 % Say kids play outside

    • 68 % 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

    • 45 % 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

    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.

    Homes for rent near Windermere Dr

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    Off Market Homes Near Windermere Dr

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    Windermere Dr, Middlesboro, KY 40965 is a lot/land. This property is not currently available for sale. Windermere Dr was last sold on Mar 19, 2026 for $32,500 (19% lower than the asking price of $40,000).