4402 Chesapeake Ave, Hampton, VA 23669
OFF MARKET

4402 Chesapeake Ave
Hampton, VA 23669

Downtown
  • 4 Beds
  • 4 Baths
  • 4,012 sqft (on 0.44 acres)

$1,038,000

Trulia Estimate
as of May 17, 2026
Est. Refi. Payment $5,972/mo*
Refinance Your Home

$1,038,000

Trulia Estimate
as of May 17, 2026
Est. Refi. Payment $5,972/mo*
Refinance Your Home
4 Beds
4 Baths
4,012 sqft
(on 0.44 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Spectacular brick waterfront Southern Mansion overlooking the beautiful waters of Hampton Roads. The home features 4 spacious bedrooms, 3 1/2 baths, a pool, and gazebo. Full of southern charm with hardwood and ceramic tile floors throughout. The details of the house are exquisite and reminiscent of days gone by, and with 3 fireplaces you will feel so cozy in winter. A must see for the discriminating buyer.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Patio, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 4402 Chesapeake Ave

Interior Features

Heating & Cooling
Heating: Heat Pump, ElectricAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Hardwood
Interior Details
Number of Rooms: 6Types of Rooms: Walk In Closet, Dining Room, Pantry
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: BrickFoundation Type: Crawl RaisedPatio
Pool
Pool
Parking & Garage
GarageParking Space: 1Parking: Garage Attached

Property Information

Year Built
Year Built: 1954
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.44 acres

Price History for 4402 Chesapeake Ave

DatePriceEventSource
01/26/2018$551,000Sold
N/A
12/04/2017$599,000PendingAgent Provided
09/13/2017$599,000PriceChange
Agent Provided
07/11/2017$699,900Listed For SaleAgent Provided
06/02/2015$745,000ListingRemovedAgent Provided
01/27/2015$745,000PriceChange
Agent Provided
04/19/2014$825,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax$8,989
Assessment$779,200
Home facts updated by county records

Comparable Sales for 4402 Chesapeake Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
4043 Catesby Jones Dr, Hampton, VA
0.11
Single-Family Home
$635,000
06/09/25
6
4.5
4,000
4017 Buchanan Dr, Hampton, VA
0.29
Single-Family Home
$462,500
12/15/25
5
3.5
3,423
4002 Chesapeake Ave, Hampton, VA
0.48
Single-Family Home
$782,800
08/18/25
5
3.5
3,000
4012 Buchanan Dr, Hampton, VA
0.32
Single-Family Home
$350,000
02/06/26
4
3
2,672
3748 Chesapeake Ave, Hampton, VA
0.76
Single-Family Home
$586,700
07/11/25
5
3.5
3,547
200 Congress Ave, Hampton, VA
0.11
Single-Family Home
$1,350,000
08/18/25
4
4
4,643
4031 Chesapeake Ave, Hampton, VA
0.26
Single-Family Home
$323,050
12/16/25
3
3
2,688
116 Ivy Home Rd, Hampton, VA
0.37
Single-Family Home
$315,000
11/25/25
3
2.5
1,804
108 Worden Ave, Hampton, VA
0.18
Single-Family Home
$214,223
08/04/25
4
2
2,088
4006 Monitor Dr, Hampton, VA
0.33
Single-Family Home
$385,000
10/23/25
4
2
2,215

Assigned Schools

These are the assigned schools for 4402 Chesapeake Ave.
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

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

What Locals Say about Downtown

At least 93 Trulia users voted on each feature.

  • 90 % Say car is needed

  • 81 % Say yards are well-kept

  • 78 % Say parking is easy

  • 77 % Say it's dog friendly

  • 72 % Say there are sidewalks

  • 71 % Say there's holiday spirit

  • 63 % Say it's walkable to restaurants

  • 59 % Say streets are well-lit

  • 56 % Say kids play outside

  • 53 % Say it's quiet

  • 48 % Say they plan to stay for at least 5 years

  • 48 % Say neighbors are friendly

  • 44 % Say it's walkable to grocery stores

  • 44 % Say people would walk alone at night

  • 38 % Say there's wildlife

  • 26 % Say there are community events

Learn more about our methodology.
  • Theresa Morgan
    "Everyone’s confusing this neighborhood with downtown Hampton it is not in downtown Hampton. It is off mercury across from Hardee’s - in a private gated community. It is on a peninsula surrounded by natural surroundings and water on three sides Has a clubhouse ,a pool ,grounds are kept incredibly nice. They have wildlife projects. Everyone is friendly and speaks and waves. I walk at sunrise and after dark at 12 o’clock at night the only thing that scares me every now and then is the occasional surprise by a rabbit, but my dog loves them "
    1
    Flag
  • Theresa Morgan
    "I don’t know where that person got. It wasn’t safe and people raced through the neighborhood. It’s in a gated community Everybody is very friendly. It’s quiet. We’re surrounded by water a beautiful wildlife I walk at night during the day I see all the ospreys egrets Heron The pier is lit up at night. You can walk out on that. Everybody respects others nobody throws trash out. I feel blessed."
    1
    Flag
  • Cierra townes
    "It’s a great place to live especially to raise children. Everything is in close proximity and it’s not busy with traffic all the time."
    1
    Flag
  • Sandnsea2022
    "This is a great neighborhood to raise a family in. I believe that in a few years the price of real estate will increase. I purchased my home 5 years ago here and the value has more than doubled. Very safe area, neighbors walk dogs and the children are friendly."
    2
    Flag
  • Trulia User
    "I love this growing area. Many locations for children to play and local fun activities are arriving such as the aquaplex, buckroe, and many more."
    2
    Flag
  • Trulia User
    "Neighbors are friendly and the location is close to the highway. Grocery store is right around the corner. "
    6
    Flag
  • Pat M.
    "Nice wide sidewalks to walk. interesting architecture to view around the downtown area. neighbors are friendly. "
    2
    Flag
  • Bela.vandevender
    "Block party and all the restaurants on Queens street, make this neighborhood special. There are so many nice houses that have potential but unfortunately owners don’t care and have allowed everything to seem run down "
    8
    Flag
  • Dominique S.
    "It’s so unsafe people will get robbed jumped plus they play on your door. It’s not safe for kids people speed through the neighborhood "
    84
    Flag
  • Dominique S.
    "This area is nice but not very safe for children or packages. There so many issues gunshots, robbery, stealing,trash, fighting and lots of trash"
    2
    Flag
  • Denisebell41
    "Family community. On a bus line for transportation for people with no car. Local police lives in the neighborhood. Park for kids are nearby. Crime is low. "
    0
    Flag
  • Nicole M.
    "It's a good neighborhood to raise kids. It does not have a near by park to play in. The bus is not far away."
    4
    Flag
  • Nicole M.
    "It's a good neighborhood to raise kids. It does not have a near by park to play in. The bus is not far away."
    1
    Flag
  • Michael A. Landon
    "I've owned a house in this neighborhood for three years and have not had any problems. It's a quite neighborhood and people are friendly and helpful."
    35
    Flag
  • Tonya
    "There are people walking their dogs here everyday. Most pick up after their dogs and respect people’s property. "
    4
    Flag
  • J_dub369
    "Dogs are welcomed, must be on a leash and cannot be on any kind of tiedown in the front yard. only allowed to roam free outside in your backyard if you have a fenced in backyard"
    5
    Flag
  • Phyllis
    "Because the people I known for years are still living around the same area and they are respectful,kind,and caring and everyone looks out for each other"
    55
    Flag
  • Krista L.
    "During the day time, Darling Stadium is a beautiful place to watch the local football games and the park next to it is great for dog walks."
    0
    Flag
  • resident
    "I know this area of Hampton and I personally would not live there. I hear of a lot of crime around this neighborhood and while it may look nice, it's not an area where you'd want to take walks in the evening or be out alone after dark. "
    0
    Flag
  • Sarah
    "I work at NASA in Hampton and stayed with friends near this house before I bought my home in Newport News. I had my car broken into and the traffic in the morning was terrible from the bus. The area is near downtown so you get a lot of foot traffic across the lawn at night. "
    5
    Flag

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Off Market Homes Near 4402 Chesapeake Ave

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4402 Chesapeake Ave, Hampton, VA 23669 is a 4 bedroom, 4 bathroom, 4,012 sqft single-family home built in 1954. 4402 Chesapeake Ave is located in Downtown, Hampton. This property is not currently available for sale. 4402 Chesapeake Ave was last sold on Jan 26, 2018 for $551,000. The current Trulia Estimate for 4402 Chesapeake Ave is $1,038,000.