16 Upper St, Winchester, KY 40391
OFF MARKET

$159,400

Trulia Estimate
  • 2 Beds
  • 2 Baths
  • 1,435 sqft (on 0.35 acres)

16 Upper St, Winchester, KY 40391

Est. Refi. Payment $1,015/mo*
Refinance Your Home
Currently Off Market - Sold Jul 9, 2013 for $75,000

Home Value

Trulia Estimate
$159K
Since last month
Decreased$11K (-6.2%)
Since last year
Decreased$10K (-5.7%)
Since last sale
Increased$85K (+112.8%)
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 +119% in the last 10 years
MonthEstimated value
2026
August 2026$160K
August 2026$159K
July 2026$170K
June 2026$179K
May 2026$184K
April 2026$184K
March 2026$172K
February 2026$169K
January 2026$169K
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
10 Upper St, Winchester, KY
0.02
Single-Family Home
$193,600
05/27/26
4
3
1,792
37 7th St, Winchester, KY
0.32
Single-Family Home
$215,000
03/18/26
3
2
1,680
44 5th St, Winchester, KY
0.23
Single-Family Home
$173,000
09/22/25
3
1
1,270
33 Bon Haven Ave, Winchester, KY
0.66
Single-Family Home
$100,000
09/24/25
3
2
1,386
406 W Washington St, Winchester, KY
0.11
Single-Family Home
$9,000
09/18/25
2
1
1,428
200 Madison Ave, Winchester, KY
0.26
Single-Family Home
$175,000
12/29/25
3
2
1,124
73 Fitch Ave, Winchester, KY
0.47
Single-Family Home
$171,600
08/17/26
3
2
1,295
314 Carolina Ave, Winchester, KY
0.43
Single-Family Home
$244,000
09/18/25
4
2
1,800
334 S Burns Ave, Winchester, KY
0.61
Single-Family Home
$165,000
06/12/26
3
1.5
1,636
34 N Burns Ave, Winchester, KY
0.32
Single-Family Home
$200,000
10/02/25
3
2
1,500

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
432 W Washington St, Winchester, KY 40391
0.06
$211,000
3
2
1,088
Off Market
24 Spring St, Winchester, KY 40391
0.09
$175,000
3
1
1,173
Foreclosure
406 W Washington St, Winchester, KY 40391
0.11
-
2
1
1,428
Off Market
11 Spring St, Winchester, KY 40391
0.12
$117,200
2
1
1,100
Off Market
360 W Washington St, Winchester, KY 40391
0.12
$187,500
3
1
1,232
Off Market
409 Walnut St, Winchester, KY 40391
0.15
$83,300
2
1
1,246
Off Market
407 Walnut St, Winchester, KY 40391
0.17
$258,600
3
2
2,146
Off Market
415 Walnut St, Winchester, KY 40391
0.17
$252,600
3
2
1,825
Off Market
352 W Washington St, Winchester, KY 40391
0.14
$165,400
3
1.5
1,246
Off Market
12 Denny Ave, Winchester, KY 40391
0.18
$214,000
3
2
1,093
Off Market
16 Denny Ave, Winchester, KY 40391
0.18
$98,500
3
1
1,152
For Sale
433 Perkins St, Winchester, KY 40391
0.20
$206,800
3
2
1,080
Off Market

Local Information

  • Map ViewExplore the area around 16 Upper St.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1970
0.35 acre lot
1,435 sqft
$111/sqft
Garage

About this House

Brick ranch with carport. Well cared for home through the years. Comfortable living room, and family room with see through f/p connecting the two areas. The bedrooms are nice sized and the master has bath, walk in closet and washer/dryer area. Enjoy the deep back yard with an outbuilding for storage. Brokered And Advertised By: Tom Goebel & Company Listing Agent: Annette Goebel
16 Upper St, Winchester, KY 40391 is a 2 bedroom, 2 bathroom, 1,435 sqft single-family home built in 1970. It last sold for $75,000 on Jul 9, 2013. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $159,400, with a rent estimate of $1,424/month.

Home Details for 16 Upper St

Interior Features

Heating & Cooling
Heating: GasAir ConditioningCooling System: CentralHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Number of Rooms: 7
Fireplace & Spa
Fireplace

Exterior Features

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

Property Information

Year Built
Year Built: 1970
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Lot Information

Lot Area: 0.35 acres

Price and Tax history

DateEventPrice
Jul 9, 2013
Source: Imagine MLS #1313256
Sold
$75,000
Jul 9, 2013
Source: Agent Provided
Listed For Sale
$78,000

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
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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"
    0
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LGBTQ Local Legal Protections

Frequently asked questions about 16 Upper St

  • What is 16 Upper St estimated to be worth?
    Trulia's estimated value for 16 Upper St in Winchester, KY is $159,400.
  • What is the price history for 16 Upper St?
    16 Upper St in Winchester, KY last sold for $75,000 in July 2013.
  • 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.
  • Does 16 Upper St have air conditioning?
    Yes, 16 Upper St in Winchester, KY has air conditioning.
  • How big is the lot at 16 Upper St?
    The lot at 16 Upper St in Winchester, KY is about 0.35 acres (15,246 sq ft).

Explore by feature - Pet Friendly

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Apartments for Rent

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Off Market Homes Near 16 Upper St

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