14 Calloway St, Winchester, KY 40391
Property image
Property image
OFF MARKET

$262,400

Trulia Estimate
  • 3 Beds
  • 2.5 Baths
  • 1,500 sqft

14 Calloway St, Winchester, KY 40391

Est. Refi. Payment $1,637/mo*
Refinance Your Home
Currently Off Market - Sold Jun 9, 2025 for $250,000

Home Value

Trulia Estimate
$262K
Since last month
Increased$800 (+0.3%)
Since last year
Increased$9K (+3.6%)
Since last sale
Increased$13K (+5%)
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 +334% in the last 10 years
MonthEstimated value
2026
September 2026$263K
August 2026$262K
July 2026$260K
June 2026$262K
May 2026$262K
April 2026$262K
March 2026$255K
February 2026$255K
January 2026$255K
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
21 Kentucky St, Winchester, KY
0.18
Single-Family Home
$219,900
05/28/26
3
2
1,340
134 Central Ave, Winchester, KY
0.20
Single-Family Home
$300,000
09/03/26
3
2
1,946
47 Buckner St, Winchester, KY
0.22
Single-Family Home
$165,000
04/30/26
3
2
1,635
17 Euclid Ave, Winchester, KY
0.41
Single-Family Home
$245,000
05/08/26
3
2
1,656
339 S Main St, Winchester, KY
0.29
Single-Family Home
$219,900
07/17/26
4
1.5
1,848
29 Euclid Ave, Winchester, KY
0.44
Single-Family Home
$190,000
04/30/26
3
2
1,498
313 S Burns Ave, Winchester, KY
0.45
Single-Family Home
$197,377
05/15/26
3
2
1,518
34 N Burns Ave, Winchester, KY
0.58
Single-Family Home
$200,000
10/02/25
3
2
1,500
115 College St, Winchester, KY
0.35
Single-Family Home
$295,000
12/27/25
3
2
1,839

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
128 Alabama St, Winchester, KY 40391
0.03
$208,500
3
2
1,526
Off Market
118 Alabama St, Winchester, KY 40391
0.02
$194,800
3
2
1,408
Off Market
116 Alabama St, Winchester, KY 40391
0.01
$249,400
4
2
1,626
Off Market
101 Alabama St, Winchester, KY 40391
0.04
$155,900
1
2
1,056
For Sale
254 S Highland St, Winchester, KY 40391
0.07
$252,600
4
2
3,395
Off Market
252 S Highland St, Winchester, KY 40391
0.07
$252,900
3
2
1,944
Off Market
112 Georgia St, Winchester, KY 40391
0.07
$202,200
3
1
1,738
Off Market
229 S Highland St, Winchester, KY 40391
0.05
$165,000
4
3
3,462
For Sale
104 Georgia St, Winchester, KY 40391
0.07
$260,100
3
2
1,758
Off Market
265 S Highland St, Winchester, KY 40391
0.10
$455,000
8
4
5,058
For Sale
217 S Highland St, Winchester, KY 40391
0.07
$180,000
4
2
2,683
Recently Sold

Local Information

  • Map ViewExplore the area around 14 Calloway St.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1940
1,500 sqft
$175/sqft

About this House

What's unique:Updated laundry roomUpdated en-suite bathroomNew bathroomsNew flooringNew hvacNew kitchen
Beautiful and completely remodeled! Welcome to this stunning home. As you pull up, you will notice a brand new driveway and the inviting front entry.
Upon entering, you will love the open floor plan and the brand new luxury vinyl plank flooring. The bright inviting kitchen is just waiting for you to cook and entertain. With brand new cabinets, quartz countertops, stainless steel appliances and brand new fixtures, you will enjoy your time in this beautiful kitchen. The updated laundry room and remodeled half bath are on the first floor off of the kitchen. The large first floor primary bedroom has a beautiful updated en-suite bathroom with a large walk in tiled shower and new vanity with sink. Your guests will feel right at home upstairs enjoying the two additional bedrooms and a newly updated full bathroom with a tub shower combo.

1year old roof, new hvac, new driveway, new siding, new flooring, new kitchen, new bathrooms, new plumbing, new electrical system, new foundation, freshly painted.

This beautiful home is move in ready. Don't wait! Your new home is waiting for you.
14 Calloway St, Winchester, KY 40391 is a 3 bedroom, 3 bathroom, 1,500 sqft single-family home built in 1940. It last sold for $250,000 on Jun 9, 2025 (1% below the $252,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $262,400, with a rent estimate of $1,524/month.
Last check for updates: about 8 hours ago
Listed by Libby VanMeter, (859) 771-4811
Marshall Lane Real Estate - Lexington
Bought with: Michael R Hilario, (859) 749-4112, The Agency
Source: Imagine MLS, MLS#25003180

Home Details for 14 Calloway St

Interior Features

Interior Details
Number of Rooms: 3Types of Rooms: Master Bedroom, Bedroom 1, Bedroom 2, Bathroom 1, Bathroom 2, Bathroom 3, Kitchen, Living Room, Utility Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 1500 Square Feet
Appliances & Utilities
Appliances: Dishwasher, Microwave, Refrigerator, RangeDishwasherLaundry: Electric Dryer Hookup,Washer HookupMicrowaveRefrigerator
Heating & Cooling
Heating: Electric,Heat PumpHas CoolingAir Conditioning: Electric,Heat PumpHas HeatingHeating Fuel: Electric
Windows, Doors, Floors & Walls
Flooring: Marble, Tile, Vinyl
Levels, Entrance, & Accessibility
Levels: One and One HalfFloors: Marble, Tile, Vinyl
View
Has a ViewView: Neighborhood

Exterior Features

Exterior Home Features
Roof: Composition ShinglePatio / Porch: DeckFoundation: Block, Stone
Parking & Garage
No CarportNo Garage
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1500 Square Feet

Property Information

Year Built
Year Built: 1940
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: HouseArchitecture: House
Building
Construction Materials: Vinyl SidingNot a New Construction
Property Information
Parcel Number: 054400400300

Price & Status

Price
List Price: $252,000
Status Change & Dates
Off Market Date: Thu May 08 2025Possession Timing: Close Of Escrow

Active Status

MLS Status: Closed

Location

Direction & Address
City: WinchesterCommunity: South Park Addition
School Information
Elementary School: ShearerJr High / Middle School: Robert CampbellHigh School: GRCHigh School District: Clark County - 7

Building

Building Area
Building Area: 1500 Square Feet

Lot Information

Lot Area: 4443.12 sqft

Miscellaneous

Mls Number: 25003180Above Grade Unfinished Area: 1500

Price and Tax history

DateEventPrice
Jun 9, 2025
Source: Imagine MLS #25003180
Sold
$250,000
May 8, 2025
Source: Imagine MLS #25003180
Contingent
$252,000
May 5, 2025
Source: Imagine MLS #25003180
PriceChange
$252,000
Price decreased by 3%
Apr 29, 2025
Source: Imagine MLS #25003180
PriceChange
$259,500
Price decreased by 1%
Apr 23, 2025
Source: Imagine MLS #25003180
PriceChange
$261,000
Price decreased by 1%

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

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

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.

Frequently asked questions about 14 Calloway St

  • What is 14 Calloway St estimated to be worth?
    Trulia's estimated value for 14 Calloway St in Winchester, KY is $262,400.
  • What is the price history for 14 Calloway St?
    14 Calloway St in Winchester, KY last sold for $250,000 in June 2025.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Winchester?
    The median sale price in Winchester is $269K. That is up $14.3K from the prior month.
  • Does 14 Calloway St have air conditioning?
    Yes, 14 Calloway St in Winchester, KY has air conditioning.
  • Does 14 Calloway St have laundry facilities?
    Yes, 14 Calloway St in Winchester, KY has laundry facilities.

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Off Market Homes Near 14 Calloway St

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