239 Pendleton St, Winchester, KY 40391
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OFF MARKET

239 Pendleton St
Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,504 sqft (on 0.45 acres)

$157,500

Trulia Estimate
as of Aug 14, 2026
Est. Refi. Payment $974/mo*
Refinance Your Home

$157,500

Trulia Estimate
as of Aug 14, 2026
Est. Refi. Payment $974/mo*
Refinance Your Home
3 Beds
1 Bath
1,504 sqft
(on 0.45 acres)

Home Value

Trulia Estimate
$158K
Since last month
Increased$2K (+1.1%)
Since last year
Decreased$8K (-4.5%)
Since last sale
Increased$39K (+32.3%)
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 +303% in the last 10 years
MonthEstimated value
2026
August 2026$159K
July 2026$158K
June 2026$157K
May 2026$154K
April 2026$155K
March 2026$148K
February 2026$153K
January 2026$146K
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
146 Cook Ave, Winchester, KY
0.15
Single-Family Home
$156,000
01/16/26
3
1
1,274
107 Sycamore St, Winchester, KY
0.28
Single-Family Home
$85,000
05/22/26
3
1
1,504
22 Magnolia St, Winchester, KY
0.18
Single-Family Home
$157,530
07/22/26
2
1
842
12 Linden Ave, Winchester, KY
0.17
Single-Family Home
$215,000
04/08/26
3
2
1,050
15 Holly Ave, Winchester, KY
0.20
Single-Family Home
$214,900
12/05/25
3
2
1,200
116 Linden Ave, Winchester, KY
0.29
Single-Family Home
$200,000
08/19/25
3
2
1,164
44 5th St, Winchester, KY
0.63
Single-Family Home
$173,000
09/22/25
3
1
1,270
47 Watts Rd, Winchester, KY
0.41
Single-Family Home
$200,000
03/04/26
3
2
1,893
31 Vine St, Winchester, KY
0.60
Single-Family Home
$186,500
12/08/25
3
1
1,443
245 Ecton Rd, Winchester, KY
0.64
Single-Family Home
$200,000
01/14/26
3
1
1,074

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
61 Melbourne St, Lexington, KY 40391
0.06
$15,000
-
-
-
Recently Sold
220 Pendleton St, Winchester, KY 40391
0.08
$140,000
2
1
902
Recently Sold
614 N Main St, Winchester, KY 40391
0.14
-
-
-
-
Off Market
146 Cook Ave, Winchester, KY 40391
0.15
$156,000
3
1
1,274
Recently Sold
14 Cook Ave, Winchester, KY 40391
0.15
$219,000
3
2
1,261
For Sale
174 Cook Ave, Winchester, KY 40391
0.18
$138,000
2
1
986
For Sale
9 Cook Ave, Winchester, KY 40391
0.15
$218,200
3
1
1,200
Off Market
12 Linden Ave, Winchester, KY 40391
0.17
$215,000
3
2
1,050
Recently Sold
22 Magnolia St, Winchester, KY 40391
0.18
$157,530
2
1
842
Recently Sold
16 Linden Ave, Winchester, KY 40391
0.19
$1,200,000
16
16
7,480
For Sale
15 Sycamore St, Winchester, KY 40391
0.21
$91,800
3
1
1,144
Off Market
15 Holly Ave, Winchester, KY 40391
0.20
$214,900
3
2
1,200
Recently Sold

Local Information

  • Map ViewExplore the area around 239 Pendleton St.
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1945
Lot Size
0.45 acres
Living Area
1,504 sqft
Price/Sqft
$105
Parking
Garage

About this House

This single-family home is located at 239 Pendleton St, Winchester, KY. 239 Pendleton St is in Winchester, KY and in ZIP code 40391. This property has 3 bedrooms, 1 bathroom and approximately 1,504 sqft of floor space. This property has a lot size of 0.45 acres and was built in 1945.
239 Pendleton St, Winchester, KY 40391 is a 3 bedroom, 1 bathroom, 1,504 sqft single-family home built in 1945. It last sold for $120,000 on May 6, 2022. It is currently off market. The Trulia Estimate is $157,500, with a rent estimate of $1,383/month.

Home Details for 239 Pendleton St

Interior Features

Heating & Cooling
Heating: GasHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Number of Rooms: 6

Exterior Features

Exterior Home Features
Roof: CompositionExterior: BrickFoundation Type: Concrete Block
Parking & Garage
GarageParking: Garage Attached, Off Street

Property Information

Year Built
Year Built: 1945
Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 0.45 acres

Price and Tax history

DateEventPrice
May 6, 2022
Source: Imagine MLS #22004520
Sold
$120,000
Mar 26, 2022
Source: Imagine MLS #22004520
Pending
$120,000
Mar 12, 2022
Source: Imagine MLS #22004520
Listed For Sale
$120,000
Oct 18, 2002
Source: N/A
Sold
$25,500

Market trends in Winchester

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$255K
$15.67KMoM
Sale-to-List Price
98.8%
0.3%MoM
Price per sq ft
$165
$9MoM
Available listings
161
3MoM
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Around this home

What Locals Say about Winchester

At least 181 Trulia users voted on each feature.

  • 89 % Say car is needed

  • 87 % Say yards are well-kept

  • 85 % Say parking is easy

  • 77 % Say it's dog friendly

  • 73 % Say kids play outside

  • 68 % Say there's holiday spirit

  • 61 % Say there are sidewalks

  • 57 % Say it's quiet

  • 53 % Say neighbors are friendly

  • 53 % Say people would walk alone at night

  • 48 % Say they plan to stay for at least 5 years

  • 44 % Say there's wildlife

  • 39 % Say streets are well-lit

  • 26 % Say it's walkable to restaurants

  • 24 % Say it's walkable to grocery stores

  • 22 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Dustin Conner
    "Rock the block events pride events Christmas parades Halloween parades beer cheese festival concerts 4th of July events free ice cream cone day"
    0
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  • Jdhurley12
    "Seems safe so far. Halloween is very popular in this neighborhood. I would recommend others to live here."
    0
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  • Kimberly Sparks
    "I was raised here. It’s always been my home and I’m trying to make it my kids home as well. I’m just trying "
    0
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  • Ccharles
    "Where I live, there are lots of space for dogs to roam and run to get their energy out. Coyotes do inhabit the area so just be mindful when your dogs are outside. "
    2
    Flag
  • Clarissa R. C.
    "Beer cheese festival is the best and The brewery is awesome. Lumas is cool too. It’s a great place to live and feel safe "
    0
    Flag
  • Joyce S.
    "Great neighborhood for walking dogs. Plenty of room to walk and areas are easy to pick up waste. Neighbors are friendly for people and pets "
    8
    Flag
  • Joyce S.
    "Great neighborhood that looks out for each other and sits on the Golf Course. Very clean, quiet neighborhood"
    5
    Flag
  • Karen K.
    "Community yard sales, lots of children and the parents watch out for each other’s children. Schools are very good. "
    2
    Flag
  • Alishacorley23
    "downtown is kind of shady but I'm from here so I know alot of people. and its cute and historic thank you."
    4
    Flag
  • Garrison9908
    "We Have a neighborhood association with a dedicated group of families that live in the area and are personally involved and educated on issues surrounding them."
    0
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  • Awallace08
    "Quiet neighborhood close to schools and shopping. Low crime area, low traffic area, properties are kept cut and clean "
    1
    Flag
  • Barb H.
    "My neighborhood is an excellent place to call home. I always see people out walking their dogs. The neighbors are friendly. "
    0
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  • Garrison9908
    "My neighborhood is a neighborhood of avid boaters and fisherman who like to live near the Kentucky River. There are a few clubs that people gather together for as well as a couple of local restaurants that are hang outs. "
    0
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  • Garrison9908
    "I’ve lived in this neighborhood for over 30 years. It is a close knit community with individuals residing here that love nature, love the Kentucky River, and all things outdoors."
    0
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  • Bridgetgwyn27
    "I travel over 25 miles a day to the next county. Can be busy especially during the 5’ o’clock hour. "
    1
    Flag
  • StephanieD
    "This is a beautiful neighborhood. On the forth of July you can sit on your deck or porch and watch the most spectacular fire work shows. It is an easy picturesque drive to Hamburg or Richmond and a quick five minute jaunt if you need a gallon of milk. Everybody I met is polite and courteous and it is very dog friendly- I once had a neighbor on another street put water out for the dogs walking by his house to drink. I wouldn't want to live anywhere else."
    1
    Flag
  • Barbara.smith13
    "There’s a pit bull that lives on east broadway that has tried to kill my dog on more than 1 occasion. I called the cops the first They did Nothing bout the attack. Put the Pitt back in his lot hooked him bk up to the car chain he was attached too!!! "
    0
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  • Barbarataulbee
    "I live here. The neighbors a great. It’s also very dog and cat friendly. Every body helps each other that lives here. They also watch out for each other. There’s never any crime in out neighborhood. "
    0
    Flag
  • Barbarataulbee
    "They would love to live here cause people watch out for each other and their doggie. Dogs are very safe in our neighborhood. "
    0
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  • Shelby G.
    "lots of street dances, 3 festivals, many community events put on by the local churches. Christmas and homecoming parades are themed, downtown does a "trick or treat on main" which is also where the street dances and beer cheese festival are."
    0
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  • Townsend m.
    "you will see dogs and their owners walking all the time in colonial park. it is a very quiet neighborhood. everyone is very nice and sweet all the kids do fundraisers for school and everyone participates."
    4
    Flag
  • Dana B.
    "Some areas are great for walking or biking but a car is needed in most areas. The traffic and commute are generally worry free. "
    0
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  • Ragan
    "Many opportunities for community involvement. Very interstate accessible so a short trip to many major cities and a lot of outdoor recreation spots. "
    0
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  • Heatherbcass
    "I have lived in my current residence for 3 years and my neighbors are like family and we all have a babysitter anytime we need one!!"
    0
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  • Cristy J.
    "very safe and friendly area, no through traffic. walk to elementary and secondary school"
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Apartments for Rent

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Explore by feature - Pet Friendly

9 pet-friendly rentals in Winchester, KY

Explore by feature - Air Conditioning

14 rentals with air conditioning in Winchester, KY

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10 rentals with a washer/dryer in Winchester, KY

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Homes for sale near 239 Pendleton St

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Off Market Homes Near 239 Pendleton St

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Frequently asked questions about 239 Pendleton St

  • What is 239 Pendleton St estimated to be worth?
    Trulia's estimated value for 239 Pendleton St in Winchester, KY is $157,500.
  • What is the price history for 239 Pendleton St?
    239 Pendleton St in Winchester, KY last sold for $120,000 in May 2022.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Winchester?
    The median sale price in Winchester is $255K. That is up $15.67K from the prior month.
  • How big is the lot at 239 Pendleton St?
    The lot at 239 Pendleton St in Winchester, KY is about 0.45 acres (19,602 sq ft).
  • Does 239 Pendleton St have a garage?
    Yes, 239 Pendleton St in Winchester, KY has a garage.