129 Upper St, Winchester, KY 40391
OFF MARKET

$42,000

Tax assessed value
  • 2 Beds
  • 1 Bath
  • 1,066 sqft

129 Upper St, Winchester, KY 40391

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
Bed
Bath
Sqft
406 W Washington St, Winchester, KY
0.15
Single-Family Home
$9,000
09/18/25
2
1
1,428
44 5th St, Winchester, KY
0.14
Single-Family Home
$173,000
09/22/25
3
1
1,270
17 Waveland Ave, Winchester, KY
0.48
Single-Family Home
$178,000
08/11/26
2
1
1,061
228 Forest Ct, Winchester, KY
0.48
Single-Family Home
$210,000
10/20/25
3
1
1,053
605 College St, Winchester, KY
0.51
Single-Family Home
$179,000
08/05/26
2
1
1,484
321 Carolina Avenue, Winchester, KY
0.42
Single-Family Home
$210,000
08/10/26
3
1
1,050
200 Madison Ave, Winchester, KY
0.23
Single-Family Home
$175,000
12/29/25
3
2
1,124
111 Fitch Ave, Winchester, KY
0.61
Single-Family Home
$139,000
05/29/26
2
1
915
22 Magnolia St, Winchester, KY
0.59
Single-Family Home
$157,530
07/22/26
2
1
842
40 Garner St, Winchester, KY
0.47
Single-Family Home
$185,000
02/06/26
3
1
1,354

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
409 Walnut St, Winchester, KY 40391
0.05
$80,500
2
1
1,246
Off Market
415 Walnut St, Winchester, KY 40391
0.08
$252,700
3
2
1,825
Off Market
407 Walnut St, Winchester, KY 40391
0.07
$258,600
3
2
2,146
Off Market
230 Elm St, Winchester, KY 40391
0.11
$261,200
3
3
2,429
Off Market
433 Perkins St, Winchester, KY 40391
0.11
$206,700
3
2
1,080
Off Market
12 Denny Ave, Winchester, KY 40391
0.12
$214,000
3
2
1,093
Off Market
24 Spring St, Winchester, KY 40391
0.09
$175,000
3
1
1,173
Foreclosure
44 5th St, Winchester, KY 40391
0.14
$178,500
3
1
1,270
Off Market
16 Denny Ave, Winchester, KY 40391
0.14
$125,000
3
1
1,152
For Sale
11 Spring St, Winchester, KY 40391
0.13
$119,800
2
1
1,100
Off Market
432 W Washington St, Winchester, KY 40391
0.14
$211,700
3
2
1,088
Off Market
406 W Washington St, Winchester, KY 40391
0.15
-
2
1
1,428
Off Market

Local Information

  • Map ViewExplore the area around 129 Upper St.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1930
Living Area
1,066 sqft

About this House

This single-family home is located at 129 Upper St, Winchester, KY. 129 Upper St is in Winchester, KY and in ZIP code 40391. This property has 2 bedrooms, 1 bathroom and approximately 1,066 sqft of floor space. This property has a lot size of 6098 sqft and was built in 1930.
129 Upper St, Winchester, KY 40391 is a 2 bedroom, 1 bathroom, 1,066 sqft single-family home built in 1930. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate rent is $1,320/month.

Home Details for 129 Upper St

Interior Features

Interior Details
Basement
Heating & Cooling
Heating: GasHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 1

Property Information

Year Built
Year Built: 1930
Property Type / Style
Property Type: Single Family Home

Exterior Features

Exterior Home Features
Exterior: OtherFoundation Type: Stone

Lot Information

Lot Area: 6098 sqft

Price and Tax history

YearProperty taxTax assessment
2025
$404
$42,000
Home facts updated by county records

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

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
    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
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  • Cristy J.
    "very safe and friendly area, no through traffic. walk to elementary and secondary school"
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 129 Upper St

  • 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.
  • What do residents say about Winchester?
    Residents describe Winchester, KY as well-kept, easy to park in, and dog-friendly. Most residents say you need a car. See recently sold homes in Winchester, KY.
  • What are the closest schools to 129 Upper St?
    The closest schools to 129 Upper St in Winchester, KY are Conkwright Elementary School (rated 4/10), George Rogers Clark High School (rated 5/10), Rev. Henry E. Baker Sr. Interm. School (Elementary, rated 5/10).
  • How big is the lot at 129 Upper St?
    The lot at 129 Upper St in Winchester, KY is about 0.14 acres (6,098 sq ft).

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