Is a car needed in Middlesboro, KY?

As of early 2026, 93% of users say car is needed

Are yards well-kept in Middlesboro, KY?

As of early 2026, 87% of users say yards are well-kept

Is parking easy in Middlesboro, KY?

As of early 2026, 81% of users say parking is easy

Does Middlesboro, KY show holiday spirit?

As of early 2026, 77% of users say there's holiday spirit

Do kids play outside in Middlesboro, KY?

As of early 2026, 71% of users say kids play outside

Is Middlesboro, KY dog-friendly?

As of early 2026, 69% of users say it's dog friendly

Do residents of Middlesboro, KY plan to stay at least 5 years?

As of early 2026, 61% of users say they plan to stay for at least 5 years

Is there wildlife in Middlesboro, KY?

As of early 2026, 58% of users say there's wildlife

Are neighbors friendly in Middlesboro, KY?

As of early 2026, 54% of users say neighbors are friendly

Would people walk alone at night in Middlesboro, KY?

As of early 2026, 52% of users say people would walk alone at night

Is Middlesboro, KY quiet?

As of early 2026, 49% of users say it's quiet

Does Middlesboro, KY have sidewalks?

As of early 2026, 44% of users say there are sidewalks

Is Middlesboro, KY walkable to restaurants?

As of early 2026, 40% of users say it's walkable to restaurants

Are the streets well-lit in Middlesboro, KY?

As of early 2026, 37% of users say streets are well-lit

Are there community events in Middlesboro, KY?

As of early 2026, 28% of users say there are community events

Is Middlesboro, KY walkable to grocery stores?

As of early 2026, 27% of users say it's walkable to grocery stores

What is the price history for Windermere Dr?

Windermere Dr in Middlesboro, KY last sold for $32,500 in March 2026.

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 .

What are the closest schools to Windermere Dr?

The closest schools to Windermere Dr in Middlesboro, KY are Bell Central School Center (Pre-K/Elementary/Middle, rated 6/10), Bell County High School (rated 5/10), Frakes School Center (Pre-K/Elementary/Middle, rated 8/10).

SOLD

MAR 19, 2026

$32,500

Last sold price

Windermere Dr, Middlesboro, KY 40965

Est. Refi. Payment $270/mo*

Refinance Your Home

Currently Off Market - Sold Mar 19, 2026 for $32,500 (19% below list price)

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

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	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	-	-
1577 Beans Fork Rd, Middlesboro, KY	2.48	Lot/Land	$130,000	08/25/26	-	-
Arie Turner Ln, Middlesboro, KY	2.64	Lot/Land	$26,000	11/26/25	-	-
305 Doe Xing, Middlesboro, KY	2.52	Lot/Land	$265,500	01/23/26	-	-
403 Winchester Ave, Middlesboro, KY	2.87	Lot/Land	$120,000	08/14/26	-	-
904A E Cumberland Ave, Middlesboro, KY	3.23	Lot/Land	$32,000	09/18/26	-	-
2503 Exeter Ave, Middlesboro, KY	3.10	Lot/Land	$12,000	07/09/26	-	-

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	0.05	$296,700	3	2	1,603	Off Market
230 Windermere Dr, Middlesboro, KY 40965	0.02	$257,300	3	2	2,099	Off Market
314 Picadilly Ct, Middlesboro, KY 40965	0.09	$293,000	4	2.5	2,576	Recently Sold
220 Windermere Dr, Middlesboro, KY 40965	0.08	$240,000	3	2.5	1,692	Recently Sold
212 Windermere Dr, Middlesboro, KY 40965	0.12	$229,900	3	2	1,476	Off Market
156 Wellington Dr, Middlesboro, KY 40965	0.19	$230,000	3	1.5	1,320	For Sale
150 Wellington Dr, Middlesboro, KY 40965	0.20	$211,000	3	2	1,140	Off Market
218 Windermere Dr, Middlesboro, KY 40965	0.28	$230,000	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	0.29	$194,200	2	2	1,059	Off Market
23 Castleford Way, Middlesboro, KY 40965	0.36	$183,500	3	1.5	1,080	Recently Sold

Local Information

Map ViewExplore the area around Windermere Dr.
Schools6 Preschool Schools6 Elementary Schools6 Middle Schools1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Lot/Land

0.67 acre lot

About this House

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!

Windermere Dr, Middlesboro, KY 40965 is a lot/land. It last sold for $32,500 on Mar 19, 2026 (19% below the $40,000 asking price). This property is not currently displayed as for sale or rent on Trulia.

Last check for updates: about 5 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

Home Details for Windermere Dr

Active Status
MLS Status: Closed

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

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

Price and Tax history

Date	Event	Price
Mar 19, 2026 Source: East Tennessee Realtors #1326396	Sold	$32,500
Feb 24, 2026 Source: East Tennessee Realtors #1326396	Pending	$40,000
Jan 14, 2026 Source: East Tennessee Realtors #1326396	Listed For Sale	$40,000

Additional Cost

Market trends in Middlesboro

Last updated August 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

2MoM

Around this home

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.
Resident
6y ago
"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
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Johanna.bowling
Resident
7y ago
"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
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Jared C.
Resident
8y ago
"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
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Dawn R.
Resident
8y ago
"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.
Resident
8y ago
"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
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loulou8094
12y ago
"I live here and this is a beautiful neighborhood, quit, within walking distance to everything in town, just a nice area"
0
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Laura K.
15y ago
"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
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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 Windermere Dr

What is the price history for Windermere Dr?
Windermere Dr in Middlesboro, KY last sold for $32,500 in March 2026.
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.
What are the closest schools to Windermere Dr?
The closest schools to Windermere Dr in Middlesboro, KY are Bell Central School Center (Pre-K/Elementary/Middle, rated 6/10), Bell County High School (rated 5/10), Frakes School Center (Pre-K/Elementary/Middle, rated 8/10).