237 Pendleton St, Winchester, KY 40391
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Property image
OFF MARKET

237 Pendleton St
Winchester, KY 40391

  • 2 Beds
  • 1 Bath
  • 2,989 sqft

$110,900

Trulia Estimate
as of Aug 10, 2026

$110,900

Trulia Estimate
as of Aug 10, 2026
2 Beds
1 Bath
2,989 sqft

Local Information

  • Map ViewExplore the area around 237 Pendleton St.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1945
Living Area
2,989 sqft
Price/Sqft
$37
Parking
Garage

About this House

This single-family home is located at 237 Pendleton St, Winchester, KY. 237 Pendleton St is in Winchester, KY and in ZIP code 40391. This property has 2 bedrooms, 1 bathroom and approximately 2,989 sqft of floor space. This property has a lot size of 9147 sqft and was built in 1945.
237 Pendleton St, Winchester, KY 40391 is a 2 bedroom, 1 bathroom, 2,989 sqft single-family home built in 1945. It last sold for $59,600 on Jan 13, 2003. It is currently off market. The Trulia Estimate is $110,900, with a rent estimate of $1,241/month.

Home Details for 237 Pendleton St

Interior Features

Heating & Cooling
Heating: GasHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Number of Rooms: 5

Exterior Features

Exterior Home Features
Roof: CompositionExterior: OtherFoundation Type: Concrete Block
Parking & Garage
GarageParking: Garage Detached

Property Information

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

Lot Information

Lot Area: 9147 sqft

Price History for 237 Pendleton St

DatePriceEventSource
01/13/2003$59,600Sold
Imagine MLS #210359
09/24/2001$49,000Sold
Imagine MLS #2109307

Market trends in Winchester

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$239K
$7.67KMoM
Sale-to-List Price
99.1%
0.4%MoM
Price per sq ft
$156
$2MoM
Available listings
163
10MoM
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Property Tax and Assessment

Year2024
Tax$491
Assessment$49,100
Home facts updated by county records

Comparable Sales for 237 Pendleton St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
107 Sycamore St, Winchester, KY
0.28
Single-Family Home
$85,000
05/22/26
3
1
1,504
22 Magnolia St, Winchester, KY
0.17
Single-Family Home
$157,530
07/22/26
2
1
842
146 Cook Ave, Winchester, KY
0.14
Single-Family Home
$156,000
01/16/26
3
1
1,274
233 E Washington St, Winchester, KY
0.55
Single-Family Home
$155,500
04/06/26
2
1
1,088
15 Holly Ave, Winchester, KY
0.19
Single-Family Home
$214,900
12/05/25
3
2
1,200
12 Linden Ave, Winchester, KY
0.17
Single-Family Home
$215,000
04/08/26
3
2
1,050
116 Linden Ave, Winchester, KY
0.29
Single-Family Home
$200,000
08/19/25
3
2
1,164
47 Watts Rd, Winchester, KY
0.41
Single-Family Home
$200,000
03/04/26
3
2
1,893
220 Pendleton St, Winchester, KY
0.06
Single-Family Home
$140,000
11/24/25
2
1
902
31 Vine St, Winchester, KY
0.58
Single-Family Home
$186,500
12/08/25
3
1
1,443

Nearby homes

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Assigned Schools

These are the assigned schools for 237 Pendleton St.
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 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
    Flag
  • Jdhurley12
    "Seems safe so far. Halloween is very popular in this neighborhood. I would recommend others to live here."
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Cristy J.
    "very safe and friendly area, no through traffic. walk to elementary and secondary school"
    0
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Apartments for Rent

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Explore by feature - Pet Friendly

19 pet-friendly rentals in Winchester, KY

Explore by feature - Air Conditioning

17 rentals with air conditioning in Winchester, KY

Explore by feature - Washer/dryer

11 rentals with a washer/dryer in Winchester, KY

Homes for sale near 237 Pendleton St

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Off Market Homes Near 237 Pendleton St

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Frequently asked questions about 237 Pendleton St

  • What is 237 Pendleton St estimated to be worth?
    Trulia's estimated value for 237 Pendleton St in Winchester, KY is $110,900.
  • What is the price history for 237 Pendleton St?
    237 Pendleton St in Winchester, KY last sold for $59,600 in January 2003.
  • 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 $239K. That is down $7.67K from the prior month.
  • How big is the lot at 237 Pendleton St?
    The lot at 237 Pendleton St in Winchester, KY is about 0.21 acres (9,147 sq ft).
  • Does 237 Pendleton St have a garage?
    Yes, 237 Pendleton St in Winchester, KY has a garage.