3900 Oak Dr E, Chesapeake, VA 23321
OFF MARKET

3900 Oak Dr E
Chesapeake, VA 23321

Western Branch North
  • 6 Beds
  • 7 Baths
  • 6,078 sqft (on 3.70 acres)

$1,509,900

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $8,794/mo*
Refinance Your Home

$1,509,900

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $8,794/mo*
Refinance Your Home
6 Beds
7 Baths
6,078 sqft
(on 3.70 acres)

Local Information

  • Map ViewExplore the area around 3900 Oak Dr E.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1988
Lot Size
3.7 acres
Living Area
6,078 sqft
Price/Sqft
$248
Parking
Garage

About this House

Awe inspiring estate with private entry and backyard peninsula! All brick Georgian with 3 levels of space with breathtaking views of Sterns Creek! Cook's kitchen with dual ovens & dishwashers. Sub Zero fridge and oversized center island. Game room with additional kitchen and fireplace overlooks salt water pool and expansive yard. Master suite with coffee/wine bar and deluxe walk in closet. The master bath offers marble floors, gorgeous tiled shower, and stand alone tub. Never leave home with your own private theatre room with projection screen and seating for the whole family! Dual detached garages with parking for 4 and finished apartment above one and storage above the other. Custom built by the original builder of the neighborhood (Buck Wheeler). 50 yr roof, 5 zone HVAC, gas powered back up generator, and much more!
3900 Oak Dr E, Chesapeake, VA 23321 is a 6 bedroom, 8 bathroom, 6,078 sqft single-family home in Western Branch North, built in 1988. It last sold for $1,150,000 on May 14, 2020. It is currently off market. The Trulia Estimate is $1,509,900, with a rent estimate of $3,772/month.

Home Details for 3900 Oak Dr E

Interior Features

Heating & Cooling
Heating: Forced Air, Heat Pump, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Tile, Concrete, Hardwood
Interior Details
AtticNumber of Rooms: 13Types of Rooms: Walk In Closet, Office, Pantry, Workshop
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowave
Fireplace & Spa
FireplaceHot Tub or Spa

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Wood, BrickFoundation Type: OtherPatio
Pool
Pool
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1988
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 3.70 acres

Price History for 3900 Oak Dr E

DatePriceEventSource
05/14/2020$1,150,000Sold
N/A
04/05/2019$1,299,000Listed For SaleAgent Provided
08/08/2016$900,000Sold
N/A
05/12/2016$975,000Listed For SaleAgent Provided
08/17/2001$825,000Sold
N/A

Market trends in Western Branch North

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$363K
$4.67KMoM
Sale-to-List Price
100.0%
Price per sq ft
$201
$9MoM
Available listings
122
8MoM
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Property Tax and Assessment

Year2025
Tax$12,757
Assessment$1,263,100
Home facts updated by county records

Comparable Sales for 3900 Oak Dr E

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
3000 Ferguson Dr, Portsmouth, VA
0.36
Single-Family Home
$875,000
11/13/25
5
3.5
4,475
3117 Harvesttime Cres, Chesapeake, VA
0.22
Single-Family Home
$745,000
06/17/26
6
4
4,683
3321 Tyre Neck Rd, Chesapeake, VA
0.51
Single-Family Home
$990,000
11/07/25
4
2.5
3,900
3917 Oak Dr E, Chesapeake, VA
0.16
Single-Family Home
$539,900
11/21/25
4
2.5
2,600
4305 Manchester Rd, Portsmouth, VA
0.85
Single-Family Home
$590,000
05/14/26
5
6
5,163
2417 Sterling Point Dr, Portsmouth, VA
0.37
Single-Family Home
$554,000
04/21/26
5
3.5
3,589
5111 Sweetbriar Cir, Portsmouth, VA
0.34
Single-Family Home
$481,890
03/25/26
4
3.5
2,800
3809 Harding Dr, Chesapeake, VA
0.35
Single-Family Home
$473,000
04/22/26
4
2.5
2,607
5221 Sweetbriar Cir, Portsmouth, VA
0.41
Single-Family Home
$513,000
06/18/26
3
3
2,798
2804 Lilley Cove Dr, Chesapeake, VA
1.24
Single-Family Home
$1,300,000
04/11/26
5
4
5,099

Nearby homes

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Assigned Schools

These are the assigned schools for 3900 Oak Dr E.
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

Western Branch North
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Western Branch North

At least 204 Trulia users voted on each feature.

  • 90 % Say it's dog friendly

  • 87 % Say car is needed

  • 86 % Say parking is easy

  • 78 % Say kids play outside

  • 75 % Say yards are well-kept

  • 74 % Say there's holiday spirit

  • 69 % Say it's quiet

  • 69 % Say there are sidewalks

  • 63 % Say people would walk alone at night

  • 62 % Say streets are well-lit

  • 56 % Say they plan to stay for at least 5 years

  • 54 % Say neighbors are friendly

  • 45 % Say it's walkable to grocery stores

  • 43 % Say it's walkable to restaurants

  • 42 % Say there's wildlife

  • 26 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Tyrone Davis
    "School bus stop locations are close to the homes. Good place to raise a family, or retire. Neighborhood yards are kept up"
    0
    Flag
  • Trulia User
    "Trick or treating is big here. People from other neighborhoods come and the houses here really go all out. "
    1
    Flag
  • Trulia User
    "Kid friendly , lots of libraries and activities, lots of families, sidewalks are plentiful, everything you need is a close drive. "
    0
    Flag
  • Trulia User
    "big fence in yards, great people who love dogs and animals in general. streets have sidewalks so when you walk your dog you hace plenty of room to walk, and no need to worry about neighborhood traffic "
    0
    Flag
  • Trulia User
    "The character of the homes and the friendliness of the neighbors. It’s quiet and there’s a strong sense of pride in home ownership. "
    2
    Flag
  • Trulia User
    "Great place to live with everything you need within 10 minutes. Mall, groceries, home improvement, vet, restaurants and more. "
    3
    Flag
  • Trulia User
    "The park is amazing to take your children to. There are plenty of sidewalk areas if you like to take a walk around the area or jog too. 🙂"
    0
    Flag
  • Trulia User
    "I have lived here 8 years. Clean, safe area to live. Interstate and stores are close by. A great place to raise a family. "
    2
    Flag
  • Trulia User
    "It’s expensive but safe and great schools it’s very expensive to live here in comparison to surrounding areas"
    0
    Flag
  • Trulia User
    "A lot of people grew up here and went to school here. Long story short and decided to raise their children here. What a great community."
    0
    Flag
  • Daniel A. S. M.
    "We’ve enjoyed owning a home here. It’s a very safe community. Lots of families walk their dogs, exercise, and ride bikes every day. It’s a joyful and friendly neighborhood to live in. We’re going to miss living here. "
    7
    Flag
  • Trulia User
    "Driving to peninsula or Norfolk/VB requires the use of a tunnel or a bridge at the minimum, so commutes tend to be a bit longer because of that. Otherwise, the commute is pretty much the same as anywhere else due to traffic snares throughout Hampton Roads."
    2
    Flag
  • Michael H.
    "I've lived here for a while and I feel it's a safe neighborhood and a good neighborhood to live in with a family. There are plenty of stores and restaurants and also plenty of places to reside. I would recommend the area to others "
    17
    Flag
  • Clarkdeajah
    "Great area to live in , also a great place to raise a family in . Everything is you’ll need is right in the area "
    4
    Flag
  • Karchrn1113
    "Holiday events. Yearly community yard sales. Halloween costume parades. Neighborhood water egg hunt."
    2
    Flag
  • Ebone D.
    "I just recently moved out here so can’t say too much but so far I love it. Diverse, friendly, quiet, safe, and seemingly unknown neighborhood."
    11
    Flag
  • Dee4u22
    "I live here and love it. It’s safe and shopping and everything near by. Kids activities all within teach as well. School system is great I heard. "
    4
    Flag
  • Clarkdeajah
    "Nothing really , there nothing really to complain about , it’s a lot of people who have dogs in this neighborhood "
    1
    Flag
  • Mslona97
    "I lived in this neighborhood for 4 years and I love the peace and quiet. Packages are delivered and not bothered with. "
    6
    Flag
  • Mzbubbela
    "Mostly fine! Occasionally there is a jam at the high rise but I have no real complaints. Can usually get to or from work in less than forty minutes. "
    0
    Flag
  • Hannah M.
    "My commute is great and easy. Getting anywhere in town is easily accessible. Buses, uber, lyft are all available resources."
    0
    Flag
  • Mzbubbela
    "This is a fantastic, family friendly area! The schools are good and the streets are safe. It’s the kind of place where children can ride their bikes and people hang Christmas lights. You know your neighbors and people wave as their walking down the street, I love living here!"
    0
    Flag
  • Shari R.
    "Good area, decent schools, as with any place it’s the parents’ responsibility to watch and take care of their children (of any age)."
    1
    Flag
  • Khalid F.
    "Love this area I feel safe here definitely a great place to raise your kids western branch high school is the best school in the area in my opinion "
    9
    Flag
  • WBresident
    "Wonderful location close to amenities. Very family friendly neighborhoods. Yards are maintained. Good public school system. "
    0
    Flag
  • Willisja25
    "Schools are great and the busses/drivers take their job seriously! Beautiful walk/run/bike path follows Bruce Road. Neighbors are all friendly and are always out walking their dogs and waving hi. "
    1
    Flag
  • Katherine H.
    "such a lovely place to raise a family. school are great, crime is low. would recommend this area to everyone!"
    0
    Flag
  • Kassie M.
    "Friendly people always out. Nice trails to walk walk on. Lots of grassy areas. No dog park in immediate arena "
    0
    Flag
  • Tgood4
    "The area looks to share information about all things animals, from vets, grooming, pet sitters to helping find lost pets "
    0
    Flag

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Apartments for Rent

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Explore by feature - Pet Friendly

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Explore by feature - Outdoor Space

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Homes for sale near 3900 Oak Dr E

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Off Market Homes Near 3900 Oak Dr E

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Frequently asked questions about 3900 Oak Dr E

  • What is 3900 Oak Dr E estimated to be worth?
    Trulia's estimated value for 3900 Oak Dr E in Chesapeake, VA is $1,509,900.
  • What is the price history for 3900 Oak Dr E?
    3900 Oak Dr E in Chesapeake, VA last sold for $1,150,000 in May 2020.
  • Is Chesapeake a buyer's or seller's market?
    Chesapeake is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Chesapeake?
    The median sale price in Chesapeake is $363K. That is down $4.67K from the prior month.
  • Does 3900 Oak Dr E have air conditioning?
    Yes, 3900 Oak Dr E in Chesapeake, VA has air conditioning.
  • Does 3900 Oak Dr E have a pool?
    Yes, 3900 Oak Dr E in Chesapeake, VA has a pool.