404 Jameson Way, Winchester, KY 40391
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OFF MARKET

404 Jameson Way
Winchester, KY 40391

  • 3 Beds
  • 1 Bath
  • 1,075 sqft

$199,600

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $1,212/mo*
Refinance Your Home

$199,600

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $1,212/mo*
Refinance Your Home
3 Beds
1 Bath
1,075 sqft

Home Value

Trulia Estimate
$200K
Since last month
Decreased$2K (-1%)
Since last year
Increased$5K (+2.7%)
Since last sale
Increased$92K (+86.4%)
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 +234% in the last 10 years
MonthEstimated value
2026
August 2026$199K
July 2026$199K
June 2026$202K
May 2026$199K
April 2026$199K
March 2026$199K
February 2026$196K
January 2026$192K
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
110 Colonial Park Dr, Winchester, KY
0.11
Single-Family Home
$201,000
09/04/25
3
1
1,235
310 Sarah Ct, Winchester, KY
0.14
Single-Family Home
$213,900
09/10/25
3
2
1,072
210 Shannon Ct, Winchester, KY
0.14
Single-Family Home
$239,000
08/07/26
3
2
1,164
300 Vanover Way, Winchester, KY
0.16
Single-Family Home
$150,000
10/14/25
3
2
1,092
521 Acadia Way, Winchester, KY
0.03
Single-Family Home
$216,000
02/27/26
4
2
1,370
193 Greenway Dr, Winchester, KY
0.47
Single-Family Home
$148,000
05/29/26
3
1
1,030
511 Acadia Way, Winchester, KY
0.08
Single-Family Home
$217,500
09/30/25
4
2
1,400
109 Spicer Rd, Winchester, KY
0.43
Single-Family Home
$91,600
08/04/26
5
1
1,281
2146 Ironworks Rd, Winchester, KY
0.36
Single-Family Home
$80,000
05/13/26
2
1
1,017
195 Center Dr, Winchester, KY
0.39
Single-Family Home
$125,000
05/15/26
6
1
1,566

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
411 Jameson Way, Winchester, KY 40391
0.05
$189,900
3
1
1,000
Off Market
412 Jameson Way, Winchester, KY 40391
0.05
$194,200
3
1
1,073
Off Market
605 Dixiana Dr, Lexington, KY 40391
0.05
$193,000
3
1
1,044
Off Market
502 Corley Ln, Winchester, KY 40391
0.04
$211,200
3
2
1,289
Off Market
521 Acadia Way, Winchester, KY 40391
0.03
$216,000
4
2
1,370
Recently Sold
523 Acadia Way, Lexington, KY 40391
0.04
$229,100
4
2
1,480
Off Market
517 Acadia Way, Lexington, KY 40391
0.04
$224,200
4
2
1,400
Off Market
418 Jameson Way, Winchester, KY 40391
0.08
$263,300
3
2.5
1,680
Off Market
113 Mary Way, Winchester, KY 40391
0.11
$244,300
3
2
1,050
Off Market
513 Acadia Way, Lexington, KY 40391
0.07
$217,300
4
2
1,344
Off Market
421 Jameson Way, Winchester, KY 40391
0.12
$274,700
3
2.5
1,487
Off Market
450 Jameson Way, Winchester, KY 40391
0.09
$218,000
4
2
1,458
Recently Sold

Local Information

  • Map ViewExplore the area around 404 Jameson Way.
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1990
Living Area
1,075 sqft
Price/Sqft
$186

About this House

WOW - This home qualifies for 100% financing, purchase with little to no money down if you qualify. Three bedroom, 1 bath brick ranch that has laminate flooring throughout. No carpet. Large living room and kitchen. This property is completely fenced and is move in ready. Don't miss this one.
404 Jameson Way, Winchester, KY 40391 is a 3 bedroom, 1 bathroom, 1,075 sqft single-family home built in 1990. It last sold for $107,000 on Oct 25, 2018. It is currently off market. The Trulia Estimate is $199,600, with a rent estimate of $1,383/month.

Home Details for 404 Jameson Way

Interior Features

Heating & Cooling
Heating: Heat Pump, ElectricHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Laminate
Interior Details
Number of Rooms: 6Types of Rooms: Walk In Closet
Appliances & Utilities
MicrowaveRefrigerator

Exterior Features

Exterior Home Features
Roof: CompositionExterior: BrickFoundation Type: Concrete BlockPatio
Parking & Garage
Parking: Carport

Property Information

Year Built
Year Built: 1990
Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 6534 sqft

Price and Tax history

DateEventPrice
Oct 25, 2018
Source: Imagine MLS #1821484
Sold
$107,000
Sep 24, 2018
Source: Agent Provided
Pending
$107,777
Sep 17, 2018
Source: Agent Provided
Listed For Sale
$107,777
Jul 5, 2017
Source: Imagine MLS #1709538
Sold
$96,000
Jun 5, 2017
Source: Agent Provided
Pending
$97,900

Market trends in Winchester

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$239K
$7.67KMoM
Sale-to-List Price
99.1%
0.4%MoM
Price per sq ft
$156
$2MoM
Available listings
163
10MoM
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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
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  • 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
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  • 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. "
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  • 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. "
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  • 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."
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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
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  • 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
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  • 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
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  • 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"
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Explore by feature - Pet Friendly

19 pet-friendly rentals in Winchester, KY

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19 rentals with air conditioning in Winchester, KY

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Homes for sale near 404 Jameson Way

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Off Market Homes Near 404 Jameson Way

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Frequently asked questions about 404 Jameson Way

  • What is 404 Jameson Way estimated to be worth?
    Trulia's estimated value for 404 Jameson Way in Winchester, KY is $199,600.
  • What is the price history for 404 Jameson Way?
    404 Jameson Way in Winchester, KY last sold for $107,000 in October 2018.
  • 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 $239K. That is down $7.67K from the prior month.
  • How big is the lot at 404 Jameson Way?
    The lot at 404 Jameson Way in Winchester, KY is about 0.15 acres (6,534 sq ft).
  • Does 404 Jameson Way have parking?
    Yes, 404 Jameson Way in Winchester, KY has on-site parking.