# 156 Wellington Drive, Middlesboro, KY 40965

> **TL;DR:** 3bd/2ba single family, $230,000 ($174/sqft), built 1994, 1,320 sqft.
> Pool, Fireplace, A/C. Est. $1,230/mo. Listed 221 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $230,000 |
| Price/sqft | $174 |
| Bedrooms | 3 |
| Bathrooms | 1 full, 1 half |
| Square Feet | 1,320 |
| Year Built | 1994 |
| Lot Size | 13,068 sqft (0.30 acres) |
| Property Type | Single Family (Single Family Residence) |
| Status | Active |
| Days on Market | 221 |

## Why This Home Stands Out

- **Pool** - Pool listed; type not specified

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $1,163 |
| Estimated Insurance | $67 |
| **Total** | **$1,230** |

## Nearby Schools

- **Elementary:** Middlesboro Ind
- **Middle:** Middlesboro Ind
- **High:** Middlesboro Ind

## Key Amenities

- Pool
- Fireplace
- A/C

## Property Highlights

- Built in 1994
- 0.30 acre lot
- Private pool
- Fireplace

## Description

### Agent Description
Welcome home to this spacious and inviting 3-bedroom, 1.5-bath property that offers both comfort and versatility! In addition to the three bedrooms, you'll find a bonus room that can easily serve as a 4th bedroom, home office, or flex space to fit your needs. This home features both a cozy living room and a separate den, providing plenty of space for relaxing or entertaining. The den is highlighted by a charming fireplace-perfect for gathering on cooler evenings. The eat-in kitchen offers a warm and functional space for everyday meals. Step outside to enjoy a large backyard complete with a swimming pool, an expansive deck, and a screened-in area attached to the deck-perfect for relaxing without worrying about pests while still enjoying the outdoors. Whether you're hosting guests or unwinding after a long day, this outdoor space has it all. With its flexible layout, multiple living spaces, and great indoor and outdoor amenities, this home has something for everyone. Don't miss your chance to make it yours!

## Location

- **Address:** 156 Wellington Drive, Middlesboro, KY 40965
- **County:** Bell
- **Neighborhood:** Windermere
- **Coordinates:** 36.642492, -83.737505
- **Google Maps:** https://www.google.com/maps?q=36.642492,-83.737505

## Listing Agent

- **Name:** Megan Stanaford
- **Brokerage:** Black Diamond Realty
- **Broker Phone:** 606-552-0879
- **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/156-Wellington-Dr_Middlesboro_KY_40965_M38801-80693?f=listhub&s=LBARKY&m=26005639&c=propsimple)

## Photos

![156 Wellington Drive - Photo 1](http://lh.rdcpix.com/bd883094d802cb2bf00f48e847f01f8bl-f3023146543r.jpg)

![156 Wellington Drive - Photo 2](http://lh.rdcpix.com/bd883094d802cb2bf00f48e847f01f8bl-f3181124931r.jpg)

![156 Wellington Drive - Photo 3](http://lh.rdcpix.com/bd883094d802cb2bf00f48e847f01f8bl-f3788709124r.jpg)

![156 Wellington Drive - Photo 4](http://lh.rdcpix.com/bd883094d802cb2bf00f48e847f01f8bl-f3540270357r.jpg)

![156 Wellington Drive - Photo 5](http://lh.rdcpix.com/bd883094d802cb2bf00f48e847f01f8bl-f1569857398r.jpg)

![156 Wellington Drive - Photo 6](http://lh.rdcpix.com/bd883094d802cb2bf00f48e847f01f8bl-f73320616r.jpg)

![156 Wellington Drive - Photo 7](http://lh.rdcpix.com/bd883094d802cb2bf00f48e847f01f8bl-f405280236r.jpg)

![156 Wellington Drive - Photo 8](http://lh.rdcpix.com/bd883094d802cb2bf00f48e847f01f8bl-f2413544241r.jpg)

![156 Wellington Drive - Photo 9](http://lh.rdcpix.com/bd883094d802cb2bf00f48e847f01f8bl-f1946441630r.jpg)

![156 Wellington Drive - Photo 10](http://lh.rdcpix.com/bd883094d802cb2bf00f48e847f01f8bl-f3525669671r.jpg)

![156 Wellington Drive - Photo 11](http://lh.rdcpix.com/bd883094d802cb2bf00f48e847f01f8bl-f3323853673r.jpg)

![156 Wellington Drive - Photo 12](http://lh.rdcpix.com/bd883094d802cb2bf00f48e847f01f8bl-f2494916858r.jpg)

![156 Wellington Drive - Photo 13](http://lh.rdcpix.com/bd883094d802cb2bf00f48e847f01f8bl-f2441417537r.jpg)

![156 Wellington Drive - Photo 14](http://lh.rdcpix.com/bd883094d802cb2bf00f48e847f01f8bl-f172120818r.jpg)

![156 Wellington Drive - Photo 15](http://lh.rdcpix.com/bd883094d802cb2bf00f48e847f01f8bl-f2121457568r.jpg)

![156 Wellington Drive - Photo 16](http://lh.rdcpix.com/bd883094d802cb2bf00f48e847f01f8bl-f566807840r.jpg)

![156 Wellington Drive - Photo 17](http://lh.rdcpix.com/bd883094d802cb2bf00f48e847f01f8bl-f2736441637r.jpg)

---

**MLS#:** 26005639 | **Updated:** 2026-10-22
**Source:** listhub

*Copyright © 2026 ImagineMLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.*

[View on PropertySimple](https://www.propertysimple.ai/listing/156-wellington-drive-middlesboro-ky-40965-5343bd09794741e2b7861aba4aefdff7)

---

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