7 Calloway St, Winchester, KY 40391
OFF MARKET

$324,800

Trulia Estimate
  • 6 Beds
  • 5 Baths
  • 4,600 sqft

7 Calloway St, Winchester, KY 40391

Est. Refi. Payment $1,991/mo*
Refinance Your Home
Currently Off Market - Sold Nov 15, 2019 for $40,000

Home Value

Trulia Estimate
$325K
Since last month
Decreased$11K (-3.1%)
Since last year
Decreased$400 (-0.1%)
Since last sale
Increased$286K (+714.3%)
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 +227% in the last 10 years
MonthEstimated value
2026
August 2026$326K
August 2026$325K
July 2026$336K
June 2026$356K
May 2026$338K
April 2026$348K
March 2026$350K
February 2026$358K
January 2026$347K
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
297 S Main St, Winchester, KY
0.20
Multi-Family Home
$325,000
04/09/26
6
4
3,544
321 S Maple St, Winchester, KY
0.20
Multi-Family Home
$270,000
10/14/25
6
4
4,490
217 S Highland St, Winchester, KY
0.03
Multi-Family Home
$180,000
07/02/26
4
2
2,683
101 S Burns Avenue #1,2,3,4, Winchester, KY
0.38
Multi-Family Home
$580,000
05/29/26
8
4
5,046
146 W Lexington Ave, Winchester, KY
0.36
Multi-Family Home
$267,000
03/24/26
8
3
3,393
21 Beckner St, Winchester, KY
0.56
Multi-Family Home
$280,000
08/26/26
6
4
3,090
101 S Burns Ave, Winchester, KY
0.38
Multi-Family Home
$580,000
06/08/26
8
4
1,296
23 1/2 Wheeler St, Winchester, KY
0.52
Multi-Family Home
$347,000
01/05/26
8
4
3,706
17 W Lexington Ave, Winchester, KY
0.24
Multi-Family Home
$355,000
07/06/26
8
8
4,000
144 Holly Ave, Winchester, KY
0.89
Multi-Family Home
$260,000
06/09/26
8
5
3,637

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
229 S Highland St, Winchester, KY 40391
0.02
$165,000
4
3
3,462
For Sale
217 S Highland St, Winchester, KY 40391
0.03
$180,000
4
2
2,683
Recently Sold
14 Calloway St, Winchester, KY 40391
0.04
$261,400
3
2.5
1,500
Off Market
116 Alabama St, Winchester, KY 40391
0.05
$247,300
4
2
1,626
Off Market
118 Alabama St, Winchester, KY 40391
0.06
$194,800
3
2
1,408
Off Market
101 Alabama St, Winchester, KY 40391
0.06
$155,900
1
2
1,056
For Sale
252 S Highland St, Winchester, KY 40391
0.08
$252,100
3
2
1,944
Off Market
128 Alabama St, Winchester, KY 40391
0.07
$207,800
3
2
1,526
Off Market
129 S Highland St, Winchester, KY 40391
0.09
$296,400
6
4
-
Off Market
254 S Highland St, Winchester, KY 40391
0.09
$249,800
4
2
3,395
Off Market
104 Georgia St, Winchester, KY 40391
0.09
$262,300
3
2
1,758
Off Market
112 Georgia St, Winchester, KY 40391
0.10
$202,900
3
1
1,738
Off Market

Local Information

  • Map ViewExplore the area around 7 Calloway St.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Multi-Family
Built in 1940
4,600 sqft
$71/sqft

About this House

This studio apartment features new carpet and fresh pain throughout. Conveniently located in downtown WInchester near shopping, restaurants and parks. All utilities are included. Tenant is responsible for cable/ internet. Pet friendly following standard breed restrictions.
7 Calloway St, Winchester, KY 40391 is a 6 bedroom, 5 bathroom, 4,600 sqft multi-family built in 1940. It last sold for $40,000 on Nov 15, 2019. More recently, it was listed as a rental in January 2020 with an asking price of $550 per month. That rental listing was removed on March 10, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $324,800, with a rent estimate of $1,484/month.

Home Details for 7 Calloway St

Interior Features

Interior Details
BasementNumber of Rooms: 16
Heating & Cooling
Heating: Forced Air, GasHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Linoleum Vinyl
Appliances & Utilities
Refrigerator

Exterior Features

Exterior Home Features
Roof: CompositionExterior: BrickFoundation Type: Stone

Property Information

Year Built
Year Built: 1940
Property Type / Style
Property Type: Multi Family

Community

Units in Building: 1

Lot Information

Lot Area: 3641 sqft

Price and Tax history

DateEventPrice
Mar 10, 2020
Source: Agent Provided
ListingRemoved
$550
Jan 10, 2020
Source: Agent Provided
Listed For Rent
$550
Nov 15, 2019
Source: Imagine MLS #1925030
Sold
$40,000
Oct 26, 2019
Source: Agent Provided
Pending
$40,000
Oct 26, 2019
Source: Agent Provided
Listed For Sale
$40,000

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
    Flag
  • 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
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 7 Calloway St

  • What is 7 Calloway St estimated to be worth?
    Trulia's estimated value for 7 Calloway St in Winchester, KY is $324,800.
  • What is the price history for 7 Calloway St?
    7 Calloway St in Winchester, KY last sold for $40,000 in November 2019.
  • 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.

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Apartments for Rent

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Off Market Homes Near 7 Calloway St

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