314 Winchester Dr, Hampton, VA 23666
Property image
Property image
PENDING
3D VIEW
0.26 ACRES

$320,000

  • 4 Beds
  • 2 Baths
  • 1,632 sqft (on 0.26 acres)

314 Winchester Dr, Hampton, VA 23666

Northampton
Est. Mortgage $1,916/mo*
Get Pre-Qualified

Home Highlights

Parking
Garage
Outdoor
Porch, Patio
Price/Sqft
$196
Listed
42 days ago
Climate Control
Forced Air, Electric & Central Air

Local Information

  • Map ViewExplore the area around 314 Winchester Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

A Home Filled With Decades of Love: Now Ready for Its Next Chapter
Some homes are simply houses; This one is different. Cherished by the same family since 1962, this beautifully renovated Hampton gem carries 60+ years of warmth within its walls; & a thoughtful top-to-bottom refresh that makes it feel brand new. Step inside to gleaming refinished hardwood floors that glow with their original luster, setting the tone throughout. The updated kitchen impresses immediately: new cabinetry, countertops, floor, sink, disposal, SS stove, DW & an existing SS refrigerator; everything you need, nothing overlooked. Just beyond, a flexible dining area/den flows naturally into the expansive family room, where beautifully restored French doors add an elegant, inviting touch. The living room anchors the original footprint with a picture window and rich hardwood floors. The original part of the house, offers three bedrooms, each with refinished hardwood floors, in a range of sizes to suit everyone. The largest bedroom provides plenty of space, a comfortable mid-sized room adapts easily to your needs & the cozy third bedroom is perfectly sized for a nursery, home office, craft room or creative hideaway; just as the current owner used it. A full bath rounds out the original part of the home. When the family grew, so did the home: a 1970s addition brought the spacious family room & Primary Suite. A detached garage w/ large workshop & a large patio was added prior. Both garage doors are brand new. Don't miss the charming sunroom out back — a peaceful retreat that opens up to gentle breezes on beautiful spring days. The backyard overlooks Kraft Elementary School playground, a sweet bonus. Location checks every box: minutes from Peninsula Town Center, Sandy Bottom Nature Park, Hampton Roads Center Parkway, I-64, Langley AFB and Ft Eustis. A rare opportunity to own a home with real history & real heart. Homes like this don't come along often.
Last check for updates: about 13 hours ago
Listing courtesy of Karen Steen, (804) 269-1605
Long & Foster REALTORS, (804) 340-0840
Originating MLS: Central Virginia Regional MLS
Source: CVRMLS, MLS#2616349
Also Listed on Long & Foster Broker Feed, CVRMLS.

Home Details for 314 Winchester Dr

Interior Features

Interior Details
Basement: Crawl SpaceNumber of Rooms: 9Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Dining Room, Family Room, Florida Room, Full Bath, Kitchen, Laundry, Living Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1632 Square Feet
Appliances & Utilities
Utilities: Sewer Not AvailableAppliances: Dishwasher, Exhaust Fan, Electric Cooking, Electric Water Heater, Disposal, Ice Maker, Microwave, Oven, Refrigerator, Stove, WasherDishwasherDisposalLaundry: Washer Hookup,Dryer HookupMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Electric,Forced AirHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Electric
Windows, Doors, Floors & Walls
Door: French Doors, Sliding Doors, Storm Door(s)Flooring: Vinyl, Wood
Levels, Entrance, & Accessibility
Stories: 1Number of Stories: 1Levels: OneAccessibility: Accessibility Features, Grab BarsFloors: Vinyl, Wood
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Rear Porch, Glass Enclosed, PatioFencing: Back Yard, Chain Link, Partial, FencedOther Structures: Shed(s), OutbuildingExterior: Out Building(s), Storage, Shed, Paved Driveway
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1Has a GarageNo Attached GarageHas Open ParkingParking Spaces: 1Parking: Driveway,Detached,Garage,Off Street,Paved,Storage,Workshop in Garage
Pool
Pool: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: None
Finished Area
Finished Area (above surface): 1632 Square Feet

Days on Market

Days on Market: 42

Property Information

Year Built
Year Built: 1954
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch
Building
Construction Materials: Frame, Plaster, Vinyl SidingNot a New ConstructionNot Attached Property
Property Information
Condition: ResaleParcel Number: 4001810

Price & Status

Price
List Price: $320,000Price Per Sqft: $196
Status Change & Dates
Off Market Date: Tue Aug 04 2026Possession Timing: Close Of Escrow

Active Status

MLS Status: Pending

Media

Location

Direction & Address
City: HamptonCommunity: Winchester Park
School Information
Elementary School: Christopher C. KraftJr High / Middle School: Cesar TarrantHigh School: Bethel

Agent Information

Listing Agent
Listing ID: 2616349

Community

Community Features: Street Lights, Sidewalks

HOA

Association for this Listing: Central Virginia Regional MLS

Lot Information

Lot Area: 0.26 acres

Business

Business Information
Ownership: Individuals

Miscellaneous

Mls Number: 2616349Living Area Range Units: Square FeetAttic: Floored, Walk-upAttribution Contact: 804-269-1605Above Grade Unfinished Area: 1632Above Grade Unfinished Area Units: Square FeetActivation Date: Fri Jul 17 2026Below Grade Unfinished Area Units: Square FeetStart Showing Date: Sat Jul 18 2026Universal Property Id: US-51650-N-4001810-R-N

Additional Information

Street LightsSidewalksDays On Market Replication: 20

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.
  • 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

Market trends in Northampton

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$287K
$733MoM
Sale-to-List Price
100.0%
Price per sq ft
$186
$6MoM
Available listings
72
4MoM

Home Value

Trulia Estimate
$318K
Since last month
Decreased$800 (-0.2%)
Since last year
Increased$63K (+24.5%)
Since last sale
Increased$306K (+2,319.7%)
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 +103% in the last 10 years
MonthEstimated value
2026
August 2026$319K
July 2026$320K
June 2026$320K
May 2026$252K
April 2026$255K
March 2026$262K
February 2026$252K
January 2026$260K
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
504 Gold Cup Rd, Hampton, VA
0.27
Single-Family Home
$351,000
07/02/26
4
2
1,650
531 Dafia Dr, Hampton, VA
0.17
Single-Family Home
$275,000
05/13/26
3
2
1,714
208 Lowden Hunt Dr, Hampton, VA
0.19
Single-Family Home
$232,000
05/08/26
4
2
1,709
419 Patrician Dr, Hampton, VA
0.26
Single-Family Home
$300,000
10/24/25
4
2
1,404
110 Londonshire Ter, Hampton, VA
0.23
Single-Family Home
$224,000
06/10/26
3
1.5
1,040
500 Blue Run Cir, Hampton, VA
0.31
Single-Family Home
$319,900
05/19/26
3
1.5
1,569
306 Lynnhaven Dr, Hampton, VA
0.40
Single-Family Home
$345,000
02/23/26
4
2
1,800
52 Londonshire Ter, Hampton, VA
0.26
Single-Family Home
$290,000
07/27/26
3
1.5
1,092
825 Weymouth Ter, Hampton, VA
0.40
Single-Family Home
$235,000
04/27/26
4
3
1,803
108 Londonshire Ter, Hampton, VA
0.23
Single-Family Home
$334,223
06/11/26
5
2.5
1,949

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 Winchester Drive, Hampton, VA 23666
0.14
$294,500
3
2
1,152
Off Market
531 Dafia Dr, Hampton, VA 23666
0.17
$377,000
3
2
1,714
For Sale
208 Lowden Hunt Dr, Hampton, VA 23666
0.19
$359,900
4
2
1,709
For Sale
512 Concord Dr, Hampton, VA 23666
0.24
$360,000
4
2
2,050
Recently Sold
611 Burton St, Hampton, VA 23666
0.22
$433,800
3
2.5
2,359
Off Market
515 Burton St, Hampton, VA 23666
0.23
$406,100
4
2.5
2,042
Off Market
305 Lampros Ct, Hampton, VA 23666
0.25
$313,900
3
2.5
1,493
Off Market
110 Londonshire Ter, Hampton, VA 23666
0.23
$245,000
3
1.5
1,040
For Sale

Price and Tax history

DateEventPrice
Aug 5, 2026
Source: CVRMLS #2616349
Pending
$320,000
Jul 17, 2026
Source: CVRMLS #2616349
Listed For Sale
$320,000
Jun 1, 1962
Source: N/A
Sold
$13,200

LGBTQ Local Legal Protections

Karen Steen, Long & Foster REALTORS, (804) 340-0840
Agent Phone: (804) 269-1605
All or a portion of the multiple Listing information is provided by the Central Virginia Regional Multiple Listing Service, LLC, from a copyrighted compilation of Listing s. All CVR MLS information provided is deemed reliable but is not guaranteed accurate. The compilation of Listings and each individual Listing are ©2026 Central Virginia Regional Multiple Listing Service, LLC. All rights reserved.

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Frequently asked questions about 314 Winchester Dr

  • What is the estimated monthly payment for 314 Winchester Dr?
    Based on a $320,000 list price with 20% down at today's rates, the estimated monthly payment for 314 Winchester Dr in Hampton, VA is approximately $1,972 (about $1,657 principal & interest, $240 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 314 Winchester Dr compare to homes in Hampton?
    314 Winchester Dr in Hampton, VA is listed at $320,000, about 12% above the $287K median sale price in Hampton.
  • What do residents say about the Northampton neighborhood?
    Residents describe the Northampton neighborhood in Hampton, VA as easy to park in, dog-friendly, and pedestrian-friendly. See homes for sale in Northampton, Hampton.
  • What are the closest schools to 314 Winchester Dr?
    The closest schools to 314 Winchester Dr in Hampton, VA are Bethel High School (rated 7/10), Cesar Tarrant Middle School (rated 5/10), Christopher C. Kraft Elementary School (rated 6/10).
  • Does 314 Winchester Dr have air conditioning?
    Yes, 314 Winchester Dr in Hampton, VA has air conditioning.
  • Does 314 Winchester Dr have laundry facilities?
    Yes, 314 Winchester Dr in Hampton, VA has laundry facilities.
314 Winchester Dr, Hampton, VA 23666 is a 4 bedroom, 2 bathroom, 1,632 sqft single-family home built in 1954. 314 Winchester Dr is located in Northampton, Hampton. This property is currently available for sale and was listed by CVRMLS on Jun 15, 2026. The MLS # for this home is MLS# 2616349.