244 Upland Dr, Hampton, VA 23666
OFF MARKET

244 Upland Dr
Hampton, VA 23666

Northampton
  • 4 Beds
  • 3 Baths
  • 2,472 sqft

$446,100

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $2,677/mo*
Refinance Your Home

$446,100

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $2,677/mo*
Refinance Your Home
4 Beds
3 Baths
2,472 sqft

Local Information

  • Map ViewExplore the area around 244 Upland Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1993
Living Area
2,472 sqft
Price/Sqft
$180
Parking
Garage

About this House

This single-family home is located at 244 Upland Dr, Hampton, VA. 244 Upland Dr is in the Northampton neighborhood in Hampton, VA and in ZIP code 23666. This property has 4 bedrooms, 3 bathrooms and approximately 2,472 sqft of floor space. This property has a lot size of 9147 sqft and was built in 1993.
244 Upland Dr, Hampton, VA 23666 is a 4 bedroom, 3 bathroom, 2,472 sqft single-family home in Northampton, built in 1993. It last sold for $255,000 on Apr 9, 2015. More recently, it was listed as a rental in August 2014 with an asking price of $1,800 per month. That rental listing was removed on March 7, 2015. It is currently off market. The Trulia Estimate is $446,100, with a rent estimate of $2,817/month.

Home Details for 244 Upland Dr

Interior Features

Heating & Cooling
Heating: Other, GasAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet, Hardwood
Interior Details
Number of Rooms: 8Types of Rooms: Breakfast Nook, Pantry
Appliances & Utilities
Cable ReadyDishwasherDisposalRefrigerator
Fireplace & Spa
FireplaceJetted Bath Tub

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Vinyl, Brick
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1993
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 9147 sqft

Price History for 244 Upland Dr

DatePriceEventSource
04/09/2015$255,000Sold
N/A
03/07/2015$1,800ListingRemovedAgent Provided
02/24/2015$264,000Listed For SaleAgent Provided
08/30/2014$1,800Listed For RentAgent Provided
02/16/2013$1,800ListingRemovedAgent Provided
11/14/2012$1,800Listed For RentAgent Provided
10/05/2011$1,800ListingRemovedAgent Provided
09/22/2011$1,800Listed For RentAgent Provided
09/08/2011$289,900ListingRemovedAgent Provided
03/04/2011$289,900Listed For SaleAgent Provided
08/09/2006$309,000Sold
N/A

Market trends in Northampton

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$287K
$8.5KMoM
Sale-to-List Price
—
Price per sq ft
$180
$2MoM
Available listings
68
11MoM
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Property Tax and Assessment

Year2025
Tax$4,404
Assessment$377,000
Home facts updated by county records

Comparable Sales for 244 Upland Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
13 Valentine Ct, Hampton, VA
0.15
Single-Family Home
$355,000
08/20/25
4
2.5
2,294
217 Upland Dr, Hampton, VA
0.13
Single-Family Home
$436,500
12/29/25
4
2.5
2,519
122 Michaels Woods Dr, Hampton, VA
0.28
Single-Family Home
$300,000
04/24/26
4
2.5
2,222
4 Fulcher Ct, Hampton, VA
0.15
Single-Family Home
$450,000
07/13/26
4
2.5
2,200
4 Mullins Ct, Hampton, VA
0.10
Single-Family Home
$489,000
07/02/26
5
2.5
2,652
4 Paquette Ct, Hampton, VA
0.26
Single-Family Home
$450,000
10/22/25
4
2.5
2,410
3 Kaleigh Ct, Hampton, VA
0.30
Single-Family Home
$435,000
09/25/25
4
2.5
2,586
39 Locksley Dr, Hampton, VA
0.21
Single-Family Home
$465,000
06/29/26
5
2.5
2,640
2 Fulcher Ct, Hampton, VA
0.14
Single-Family Home
$490,000
05/12/26
3
3
2,024
9 Ancel Ct, Hampton, VA
0.35
Single-Family Home
$355,000
06/18/26
4
2.5
2,171

Nearby homes

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Assigned Schools

These are the assigned schools for 244 Upland Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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.
  • 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

Apartments for Rent

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Explore by feature - Pet Friendly

111 pet-friendly rentals in Hampton, VA

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Explore by feature - Outdoor Space

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Homes for sale near 244 Upland Dr

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Off Market Homes Near 244 Upland Dr

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Frequently asked questions about 244 Upland Dr

  • What is 244 Upland Dr estimated to be worth?
    Trulia's estimated value for 244 Upland Dr in Hampton, VA is $446,100.
  • What is the price history for 244 Upland Dr?
    244 Upland Dr in Hampton, VA last sold for $255,000 in April 2015.
  • Is Hampton a buyer's or seller's market?
    Hampton is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Hampton?
    The median sale price in Hampton is $287K. That is up $8.5K from the prior month.
  • Does 244 Upland Dr have air conditioning?
    Yes, 244 Upland Dr in Hampton, VA has air conditioning.
  • How big is the lot at 244 Upland Dr?
    The lot at 244 Upland Dr in Hampton, VA is about 0.21 acres (9,147 sq ft).