419 Winchester Dr, Hampton, VA 23666
Property image
Property image
OFF MARKET

$255,700

Trulia Estimate
as of Oct 2, 2026
  • 3 Beds
  • 1 Bath
  • 1,152 sqft

419 Winchester Dr, Hampton, VA 23666

Northampton

Home Highlights

Single-Family Home
1,152 sqft
$222/sqft

Local Information

  • Map ViewExplore the area around 419 Winchester Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

What's unique:Fresh paintedHardwood floorsLaundry appliances
Nice size 3-bedroom house in Great Area. Close to shopping, bases, parks and I-64 Interstate. Fresh painted and updated, Hardwood floors, All package Kitchen and laundry appliances... Ready for move in.
Please Text Agent for more info and private showing.

Rent/Lease on 12-month term.
Owner/Landlord managing own property in rental term.
419 Winchester Dr, Hampton, VA 23666 is a 3 bedroom, 1 bathroom, 1,152 sqft single-family home in Northampton. It last sold for $88,000 on Jan 10, 2018 (5,076% above the $1,700 asking price). More recently, it was listed as a rental in December 2025 with an asking price of $1,700 per month. That rental listing was removed on January 17, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $255,700, with a rent estimate of $1,758/month.

Home Details for 419 Winchester Dr

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: Central AirHeating Fuel: Forced Air
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Hardwood

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Comparable Sales for 419 Winchester Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
45 Londonshire Ter, Hampton, VA
0.43
Single-Family Home
$155,000
03/31/26
3
1
1,200 sqft
823 Headrow Ter, Hampton, VA
0.35
Single-Family Home
$272,500
09/28/26
3
1
1,013 sqft
303 Dover Rd, Hampton, VA
0.51
Single-Family Home
$187,000
02/27/26
3
1
1,204 sqft
110 Londonshire Ter, Hampton, VA
0.27
Single-Family Home
$224,000
06/10/26
3
1.5
1,040 sqft
531 Dafia Dr, Hampton, VA
0.16
Single-Family Home
$275,000
05/13/26
3
2
1,714 sqft
307 Dover Rd, Hampton, VA
0.50
Single-Family Home
$233,000
03/13/26
3
1
1,000 sqft
215 Avon Rd, Hampton, VA
0.61
Single-Family Home
$140,000
02/04/26
3
1
1,513 sqft
419 Patrician Dr, Hampton, VA
0.14
Single-Family Home
$300,000
10/24/25
4
2
1,404 sqft
125 Cynthia Dr, Hampton, VA
0.54
Single-Family Home
$315,000
05/04/26
3
1
1,152 sqft
103 Londonshire Ter, Hampton, VA
0.33
Single-Family Home
$290,000
02/20/26
3
2
1,050 sqft

Nearby homes

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Around this home

Neighborhood Overview

Northampton
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Northampton

At least 226 Trulia users voted on each feature.

  • 91 % Say car is needed

  • 82 % Say parking is easy

  • 81 % Say it's dog friendly

  • 77 % Say there are sidewalks

  • 75 % Say yards are well-kept

  • 74 % Say there's holiday spirit

  • 65 % Say streets are well-lit

  • 60 % Say it's quiet

  • 56 % Say kids play outside

  • 48 % Say it's walkable to grocery stores

  • 46 % Say people would walk alone at night

  • 45 % Say neighbors are friendly

  • 45 % Say they plan to stay for at least 5 years

  • 36 % Say it's walkable to restaurants

  • 35 % Say there's wildlife

  • 18 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Kermit89060
    "Halloween and Yard sales"
    0
    Flag
  • Melsevcik
    "It is a nice area, residents have lived here awhile. Everyone knows eqch other. It is friendly. Most take care of their lawn well "
    0
    Flag
  • Marquita Smith
    "My commute is fine depending on what time of the day that I leave out for work. 95%of the time is a clear commute "
    3
    Flag
  • Mary Jo Mcconville
    "Great family neighborhood. I have raised my children here. There are parks and grocery stores and pharmacies nearby. Also a new public school just outside of the neighborhood."
    2
    Flag
  • Mmks9xn5yx
    "There are sidewalks to walk your dogs as well as great street lighting if you walk them at night. The streets are also wide enough if there isn’t a sidewalk you won’t have to worry about cars"
    0
    Flag
  • Trulia User
    "there are dog walkers and plenty of loose dogs also. I don't feel comfortable walking the block qith my children because of it."
    3
    Flag
  • Trulia User
    "quiet neighborhood, people normally stay to themselves. alot of car break ins a few blocks over. close to everything. only downside is that you are really close to your neighbors so you can hear everything outside."
    2
    Flag
  • Trulia User
    "There are a lot of elementary and middle school kids in our area. It’s fun to watch them play ball or ride bikes together. "
    1
    Flag
  • Trulia User
    "Close to everything you need or want. Food, clothing, coffee, restaurants, and great community focus. "
    0
    Flag
  • Karen D. .
    "We have lived here for 12 years and it’s been nice and friendly neighbors and convenient to shopping and the interstate."
    4
    Flag
  • Mykab2003
    "i live here for 3 years peaceful . Packages sometime lost due to mail handlers and wrong number sequence out here !! Good to raise kids "
    30
    Flag
  • Susanhazelwood8430
    "most all of my neighbors are very friendly and look out for each other. we all have cameras as well "
    1
    Flag
  • Brandon A. A. L.
    "My neighbors are great, but there is quite a bit of crime that keeps becoming more frequent. It’s a convenient place to live pretty close to everything. "
    26
    Flag
  • Travone.hamilton
    "The new businesses developing in the area make my neighborhood unique to live in. You should definitely check it it "
    4
    Flag
  • Brittbrat4.bd
    "I’ve lived here for 10 years and it is not, nor has it ever been parking in the evenings or weekends!"
    6
    Flag
  • Austinkmartin97
    "I’ve lived in the neighborhood for a year, and it’s so quiet compared to other parts of Hampton or Newport News. I rarely hear gunshots (which is saying a lot for the city we live in) and I don’t worry about people trying to run my car."
    11
    Flag
  • Trulia User
    "It’s a pretty nice neighborhood for the most part. I don’t think I would walk alone at dusk or in the dark, but I feel like that’s most places now days. "
    7
    Flag
  • Kelly O.
    "Having a car is pretty imperative, but we’re very close to the highway which is extremely convenient"
    3
    Flag
  • Kelly O.
    "Very friendly neighbors in general. The nicer and not so nice areas around here run right into each other, so it can be a little tricky to find the right area."
    4
    Flag
  • Anthonybrown35
    "They would not have a problem with this neighborhood. The area is nice and quiet. I see neighbors with walking their pets all the time. "
    2
    Flag
  • Bengill7
    "We’ve loved this neighborhood for 18 years - it’s family oriented and close to everything including all the military installations, shopping and entertainment. Best neighborhood in Hampton."
    7
    Flag
  • Viciousdove
    "My neighborhood has great access to transportation, there is a school across the street through the woods. There’s a walk path to get to it. It’s close to shopping centers and many other things such as the park and War museum."
    0
    Flag
  • Trulia User
    "it's relatively quiet at night. everyone knows someone and law enforcement are in the community so its not that much crime in the area."
    2
    Flag

LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
Jan 17, 2026
Source: Zillow Rentals
ListingRemoved
$1,700
Dec 30, 2025
Source: Zillow Rentals
Listed For Rent
$1,700
Sep 27, 2018
Source: Agent Provided
ListingRemoved
$1,100
Sep 17, 2018
Source: Agent Provided
Listed For Rent
$1,100
Jan 10, 2018
Source: WMLS #1742145
Sold
$88,000

Frequently asked questions about 419 Winchester Dr

  • What is 419 Winchester Dr estimated to be worth?
    Trulia's estimated value for 419 Winchester Dr in Hampton, VA is $255,700.
  • What is the price history for 419 Winchester Dr?
    419 Winchester Dr in Hampton, VA last sold for $88,000 in January 2018.
  • Is Hampton a buyer's or seller's market?
    Hampton is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Hampton?
    The median sale price in Hampton is $285K. That is up $1.33K from the prior month.
  • Does 419 Winchester Dr have air conditioning?
    Yes, 419 Winchester Dr in Hampton, VA has air conditioning.
  • Does 419 Winchester Dr have laundry facilities?
    Yes, 419 Winchester Dr in Hampton, VA has in-unit laundry.

Homes for rent near 419 Winchester Dr

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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