4101 Daggerboard Dr, Chesapeake, VA 23321
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Property image
OFF MARKET

4101 Daggerboard Dr
Chesapeake, VA 23321

Western Branch South
  • 5 Beds
  • 4 Baths
  • 2,565 sqft

$428,600

Trulia Estimate
as of Jul 7, 2026
Est. Refi. Payment $2,480/mo*
Refinance Your Home

$428,600

Trulia Estimate
as of Jul 7, 2026
Est. Refi. Payment $2,480/mo*
Refinance Your Home
5 Beds
4 Baths
2,565 sqft

Local Information

  • Map ViewExplore the area around 4101 Daggerboard Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

This single-family home is located at 4101 Daggerboard Dr, Chesapeake, VA. 4101 Daggerboard Dr is in the Western Branch South neighborhood in Chesapeake, VA and in ZIP code 23321. This property has 5 bedrooms, 4 bathrooms and approximately 2,565 sqft of floor space. This property was built in 2011.
4101 Daggerboard Dr, Chesapeake, VA 23321 is a 5 bedroom, 4 bathroom, 2,565 sqft single-family home in Western Branch South, built in 2011. It last sold for $352,500 on Mar 17, 2023. More recently, it was listed as a rental in May 2023 with an asking price of $2,775 per month. That rental listing was removed on May 16, 2023. It is currently off market. The Trulia Estimate is $428,600, with a rent estimate of $3,608/month.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 4101 Daggerboard Dr

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: OtherHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Interior Details
AtticNumber of Rooms: 8
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: OtherFoundation Type: Slab
Parking & Garage
GarageParking: Garage Detached, Off Street

Property Information

Year Built
Year Built: 2011
Property Type / Style
Property Type: Single Family Home

Price History for 4101 Daggerboard Dr

DatePriceEventSource
05/16/2023ListingRemovedZillow Rentals
05/12/2023$2,775Listed For RentZillow Rentals
03/17/2023$352,500Sold
N/A
02/28/2023$348,900Listed For SaleREIN Inc. #10476033
04/17/2012$260,000Sold
N/A

Market trends in Chesapeake

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$386K
$3.67KMoM
Sale-to-List Price
100.0%
Price per sq ft
$213
$3MoM
Available listings
909
54MoM
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Property Tax and Assessment

Year2025
Tax$4,119
Assessment$407,800
Home facts updated by county records

Comparable Sales for 4101 Daggerboard Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
4305 Mast Head Way, Chesapeake, VA
0.22
Single-Family Home
$396,000
01/21/26
5
3.5
2,417
1609 Kingfisher Ct, Chesapeake, VA
0.28
Single-Family Home
$895,000
09/02/25
6
4
3,300
4141 Sunkist Rd, Chesapeake, VA
0.38
Single-Family Home
$384,900
08/15/25
3
2.5
2,268
4200 Airline Blvd, Chesapeake, VA
0.29
Single-Family Home
$345,000
09/16/25
3
2.5
1,592
1704 Sandy Pines Ct, Chesapeake, VA
0.17
Single-Family Home
$355,900
02/27/26
3
2
1,459
1800 Whites Landing Ct, Chesapeake, VA
0.38
Single-Family Home
$600,000
01/14/26
4
2.5
2,525
1630 Dock Landing Rd, Chesapeake, VA
0.38
Single-Family Home
$565,000
12/02/25
4
2.5
2,900
3820 Whites Lndg, Chesapeake, VA
0.44
Single-Family Home
$830,000
07/18/25
5
3.5
4,023
3941 Sextant St, Chesapeake, VA
0.38
Single-Family Home
$329,500
06/22/26
4
2
1,485
4128 Sunkist Rd, Chesapeake, VA
0.33
Single-Family Home
$300,000
08/26/25
3
2
1,799

Nearby homes

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Assigned Schools

These are the assigned schools for 4101 Daggerboard 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

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

What Locals Say about Western Branch South

At least 110 Trulia users voted on each feature.

  • 93 % Say car is needed

  • 93 % Say parking is easy

  • 85 % Say it's dog friendly

  • 84 % Say kids play outside

  • 82 % Say yards are well-kept

  • 79 % Say it's quiet

  • 77 % Say there's holiday spirit

  • 71 % Say people would walk alone at night

  • 59 % Say streets are well-lit

  • 58 % Say they plan to stay for at least 5 years

  • 56 % Say neighbors are friendly

  • 49 % Say there's wildlife

  • 41 % Say there are sidewalks

  • 39 % Say there are community events

  • 22 % Say it's walkable to grocery stores

  • 16 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Our neighborhood is a hidden gem, tight bit community that offers special events for children around the holidays and random get together during the summer. It’s a great time and place to live!!!"
    0
    Flag
  • Trulia User
    "My only wish is that the Main road would have sidewalks, if it did walking to the park would be much easier."
    0
    Flag
  • Trulia User
    "Very safe and private. Neighbors care about each other! New neighborhood elementary school is nearing completion. "
    1
    Flag
  • Trulia User
    "It has been nice living here for 6 years now. It’s very quiet and my neighbors are the sweetest. We all look out for each other and our kids. Western Branch is definitely a great place to raise a family. "
    0
    Flag
  • Trulia User
    "A few years ago we did holiday events for every holiday! My favorite was Christmas Caroling door to door! This neighborhood in Chadswyck Terrace is amazing! Neighbors are always so kind, helpful, thoughtful, and friendly. Overall I have really enjoyed living here. "
    0
    Flag
  • Trulia User
    "Best neighbors ever. Everyone is friendly and looks out for one another. I feel safe here letting my kids play outside. "
    0
    Flag
  • Natenumber5
    "There are plenty of bus stops along the main road. Not far from the I64, I264, interchange, which allows for a sub 30 min drive to any shipyard. Perfect location for anyone in a trade or the military."
    1
    Flag
  • Unknownroad4me
    "The Chesapeake City Park has a dog park that is perfect for the furry friends and is surrounded by calming nature. "
    0
    Flag
  • Donnamrice
    "Great schools, great neighbors, yards are well-kept, and there are neighborhood events about 3-4 times per year. "
    1
    Flag
  • Thomas.guirkin
    "Very safe location to raise a family. Many military families in the area as well. Most are 30s/40s. Very unique neighborhood with a mix of new and older homes."
    2
    Flag
  • Thomas.guirkin
    "It’s very do friendly with plenty of sidewalks. The area is also very safe. There is so,e heavy traffic from time to time, but usually it’s pretty tame."
    0
    Flag
  • Thomas.guirkin
    "This is a great neighborhood! We are renting a house currently but are now looking to buy in this area in the next several months. It’s easy access to the interstate and traffic is manageable."
    10
    Flag
  • Thomas.guirkin
    "Very nice area with easy access to the interstate and only 30 minutes from the beach. Traffic isn’t too bad either"
    0
    Flag
  • Jennifer T.
    "This neighborhood feels safe. The children play outside together often. Neighbors tend to look out for one another. We’ve been happy living here. It’s a friendly and peaceful area to raise kids. "
    1
    Flag
  • Bryonspah
    "this neighborhood is known for the family atmosphere. very quite and shaded with the opportunity to walk your dogs along other homeowners in the neighborhood. "
    2
    Flag
  • Macsgirl
    "It is all brick homes, manicured yards, and wide roads. Very beautiful neighborhood. I have been her a year and have not experienced or heard of any crime. "
    0
    Flag
  • Eduk8u2
    "I've lived here for fifteen years, and it's the PERFECT place to raise a family! Come give Bailey's Creek a try! "
    6
    Flag
  • Marie R.
    "Its a great place for young families. Very friendly and lots of areas to meet other young couples. Community is close to 664 and 64. Has good schools! Neighbors are quite friendly and there are many families in the military in this area. "
    1
    Flag
  • Otisosei
    "great neighborhood. quite and easy to get out and walk or bike. very safe with city parks close by. community center is right outside the neighborhood and numerous shopping centers and the Chesapeake square mall is less than a quarter mile away. "
    6
    Flag
  • Kaneishaport
    "its just a friendly place to live. well kept and well maintained i love being here and i feel safe at all times..."
    3
    Flag
  • Ava D.
    "There’s a lot of dogs in this neighborhood that are usually outside so if your dog isn’t good with other dogs it might not work out"
    1
    Flag
  • Stacey J.
    "I've lived in this neighborhood for three years. It's quite and has friendly neighbors that look out for another. "
    2
    Flag
  • Carolynn W.
    "It’s a wonderful and friendly atmosphere i l have neighbors I’ve known for years and they are always asking to come over , but this area is a lot of older and young family’s "
    2
    Flag

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Homes for sale near 4101 Daggerboard Dr

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Off Market Homes Near 4101 Daggerboard Dr

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