32 Jackson St, Winchester, KY 40391
Property image
Property image
FOR SALE

$189,000

Original price: $199,000
  • 3 Beds
  • 1 Bath
  • 1,152 sqft

32 Jackson St, Winchester, KY 40391

Est. Mortgage $1,200/mo*
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Home Highlights

Single-Family Home
Built in 1940
$164/sqft
Garage

Local Information

  • Map ViewExplore the area around 32 Jackson St.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

What's unique:New roofOversized garageHuge backyardSpacious bedrooms
This beautiful home is located just minutes from historic downtown Winchester. It has 3 spacious bedrooms and 1 full bath. The home has a new roof. When you walk out back you will find an oversized garage. The huge backyard is all fenced in. Make an appointment to tour this one before it's gone.
Last check for updates: about 21 hours ago
Listing courtesy of Dale Hatton, (859) 556-0330
Dream Maker Realty, LLC
Source: Imagine MLS, MLS#26020135
Also Listed on Imagine MLS.

Home Details for 32 Jackson St

Interior Features

Interior Details
Number of Rooms: 8Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bathroom 1, Kitchen, Living Room, Utility Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 1Number of Bathrooms (full): 1
Dimensions and Layout
Living Area: 1152 Square Feet
Appliances & Utilities
Utilities: Electricity Connected, Natural Gas Connected, Sewer ConnectedAppliances: Dishwasher, Refrigerator, CooktopDishwasherLaundry: Electric Dryer HookupRefrigerator
Heating & Cooling
Heating: Natural GasHas CoolingAir Conditioning: Central Air,GasHas HeatingHeating Fuel: Natural Gas
Fireplace & Spa
No Fireplace
Windows, Doors, Floors & Walls
Window: BlindsFlooring: Hardwood
Levels, Entrance, & Accessibility
Levels: OneFloors: Hardwood

Exterior Features

Exterior Home Features
Roof: ShingleFencing: Chain LinkFoundation: BlockNo Private Pool
Parking & Garage
No CarportHas a GarageNo Attached GarageHas Open ParkingParking: Detached Garage,Driveway
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Farm & Range
Not Allowed to Raise Horses
Finished Area
Finished Area (above surface): 1152 Square Feet

Days on Market

Days on Market: 56

Property Information

Year Built
Year Built: 1940
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch
Building
Construction Materials: Vinyl SidingDoes Not Include Home Warranty
Property Information
Parcel Number: 054302000900

Price & Status

Price
List Price: $189,000Price Per Sqft: $164
Status Change & Dates
Possession Timing: Close Of Escrow

Active Status

MLS Status: Active

Location

Direction & Address
City: Winchester
School Information
Elementary School: ShearerJr High / Middle School: Conkwright(Legacy)High School: GRCHigh School District: Clark County - 7

Agent Information

Listing Agent
Listing ID: 26020135

Building

Building Area
Building Area: 1152 Square Feet

HOA

No HOA

Lot Information

Lot Area: 7840.8 sqft

Miscellaneous

Mls Number: 26020135Above Grade Unfinished Area: 1152

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
    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
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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
    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
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Market trends in Winchester

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$269K
$14.3KMoM
Sale-to-List Price
99.3%
0.5%MoM
Price per sq ft
$164
$0MoM
Available listings
157
5MoM

Home Value

Trulia Estimate
$185K
Since last month
Decreased$8K (-4%)
Since last year
Increased$33K (+21.9%)
Since last sale
Increased$132K (+249.8%)
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 +277% in the last 10 years
MonthEstimated value
2026
September 2026$185K
August 2026$193K
July 2026$208K
June 2026$151K
May 2026$153K
April 2026$149K
March 2026$145K
February 2026$142K
January 2026$130K
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
118 Park Ave, Lexington, KY
0.12
Single-Family Home
$136,000
08/27/26
3
1
1,150
233 E Washington St, Winchester, KY
0.07
Single-Family Home
$155,500
04/06/26
2
1
1,088
31 Vine St, Winchester, KY
0.10
Single-Family Home
$186,500
12/08/25
3
1
1,443
371 E Washington St, Winchester, KY
0.22
Single-Family Home
$178,500
07/10/26
3
1
1,198
220 E Washington St, Winchester, KY
0.04
Single-Family Home
$135,000
08/28/26
3
1
1,097
37 Ashland Ave, Winchester, KY
0.26
Single-Family Home
$139,000
05/29/26
2
1
904

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
20 Jackson St, Winchester, KY 40391
0.03
$261,500
3
2
1,650
Off Market
37 Jackson St, Winchester, KY 40391
0.04
$191,200
3
1
1,400
Off Market
48 Jackson St, Winchester, KY 40391
0.04
$201,300
5
3
-
Off Market
220 E Washington St, Winchester, KY 40391
0.04
$135,000
3
1
1,097
Recently Sold
42 Park Ave, Winchester, KY 40391
0.07
$209,000
3
1.5
1,129
Off Market
233 E Washington St, Winchester, KY 40391
0.07
$155,500
2
1
1,088
Recently Sold
21 Vine St, Winchester, KY 40391
0.10
$223,900
3
1
1,080
Off Market
31 Vine St, Winchester, KY 40391
0.10
$186,500
3
1
1,443
Recently Sold
217 E Washington St, Lexington, KY 40391
0.09
$265,100
4
3
2,183
Off Market
116 Park Ave, Winchester, KY 40391
0.11
$139,500
1
1
1,576
Off Market
118 Park Ave, Lexington, KY 40391
0.12
$136,000
3
1
1,150
Recently Sold

Price and Tax history

DateEventPrice
Sep 8, 2026
Source: Imagine MLS #26020135
PriceChange
$189,000
Price decreased by 5%
Aug 8, 2026
Source: Imagine MLS #26020135
PriceChange
$199,000
Price decreased by 5%
Jul 28, 2026
Source: Imagine MLS #26020135
Listed For Sale
$209,000
Sep 21, 2004
Source: N/A
Sold
$53,000

LGBTQ Local Legal Protections

Dale Hatton, Dream Maker Realty, LLC
Agent Phone: (859) 556-0330
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

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Frequently asked questions about 32 Jackson St

  • What is the estimated monthly payment for 32 Jackson St?
    Based on a $189,000 list price with 20% down at today's rates, the estimated monthly payment for 32 Jackson St in Winchester, KY is approximately $1,212 (about $1,022 principal & interest, $115 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 32 Jackson St compare to homes in Winchester?
    32 Jackson St in Winchester, KY is listed at $189,000, about 30% below the $269K median sale price in Winchester.
  • 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 homes for sale in Winchester, KY.
  • What are the closest schools to 32 Jackson St?
    The closest schools to 32 Jackson St in Winchester, KY are George Rogers Clark High School (rated 5/10), Rev. Henry E. Baker Sr. Interm. School (Elementary, rated 5/10), Robert D Campbell Junior High School (rated 5/10).
  • Does 32 Jackson St have air conditioning?
    Yes, 32 Jackson St in Winchester, KY has air conditioning.
  • Does 32 Jackson St have laundry facilities?
    Yes, 32 Jackson St in Winchester, KY has laundry facilities.
32 Jackson St, Winchester, KY 40391 is a 3 bedroom, 1 bathroom, 1,152 sqft single-family home built in 1940. This property is currently available for sale and was listed by Imagine MLS on Jul 28, 2026. The MLS # for this home is MLS# 26020135.