4404 Greendell Rd, Chesapeake, VA 23321
Property image
Property image
OFF MARKET

$387,900

Trulia Estimate
as of Sep 11, 2026
  • 5 Beds
  • 2.5 Baths
  • 1,900 sqft

4404 Greendell Rd, Chesapeake, VA 23321

Western Branch North

Home Highlights

Single-Family Home
1,900 sqft
$204/sqft

Local Information

  • Map ViewExplore the area around 4404 Greendell Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

For Rent Spacious 5 Bedroom Home in Western Branch! Available February 15th

Located in the highly desirable Western Branch community, this well-maintained and spacious 5-bedroom home offers comfort, convenience, and exceptional outdoor amenities. Set within a top-rated school district and close to major conveniences, this property is an excellent choice for those seeking a thoughtfully updated and inviting residence.

Interior Features:
The home features a generous primary bedroom with an impressive walk-in closet outfitted with built-in shelving for ample storage and organization.

Throughout the years, the property has received numerous upgrades, including:

Two brand-new HVAC systems for reliable year-round climate control

Updated bathrooms

A refreshed laundry room

A new water heater

Outdoor Features:
A standout feature of this property is the expansive 900 sq. ft. shed/workshop, ideal for storage, projects, or hobby use. The large, level yard offers extensive space for outdoor activities and entertainment.

The backyard includes multiple raised organic garden beds currently producing fresh vegetables and herbs, perfect for both new and seasoned gardeners. A recently built pergola provides a peaceful outdoor retreat for relaxing or hosting guests.

Additional Amenities

Whole-home water filtration system, providing softened and filtered water throughout

Driveway parking for three to four vehicles

Pet Policy:
This property is pet-friendly. A pet deposit is required for each pet, along with documentation for all animals residing on the premises. Pet deposit's are non-refundable.

Location:
Conveniently situated near Western Branch's top-rated schools, shopping centers, restaurants, interstates, and everyday amenities, this home offers an ideal blend of accessibility and neighborhood tranquility.

The renter is responsible for all utilities. Lawn care can be negotiated.
The home is available for a 1-year lease, followed by a month-to-month option. The owner is willing to offer a 2-year lease. Lease terms may be negotiable for military families.
Smoking is strictly prohibited inside the home due to a severe allergy of one of the owners.
The pet deposit is non-refundable. Tenants must clean up after their pets, and any pet-related damage exceeding the deposit amount will be deducted from the standard security deposit. A maximum of two dogs is permitted.

Tenants are responsible for basic maintenance, including replacing air filters and lightbulbs.
4404 Greendell Rd, Chesapeake, VA 23321 is a 5 bedroom, 3 bathroom, 1,900 sqft single-family home in Western Branch North. It last sold for $290,000 on Feb 23, 2021 (11,114% above the $2,586 asking price). More recently, it was listed as a rental in November 2025 with an asking price of $2,586 per month. That rental listing was removed on November 25, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $387,900, with a rent estimate of $2,903/month.

Home Details for 4404 Greendell Rd

Interior Features

Heating & Cooling
Heating: Heat PumpAir ConditioningCooling System: Central AirHeating Fuel: Heat Pump
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Carpet, Tile

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Exterior Features

Exterior Home Features
Garden

Comparable Sales for 4404 Greendell Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
4416 Greendell Rd, Chesapeake, VA
0.05
Single-Family Home
$385,000
08/04/26
4
2.5
1,456 sqft
3403 Bernies Ct S, Chesapeake, VA
0.27
Single-Family Home
$385,000
08/13/26
4
2.5
1,674 sqft
3112 Jasmine Ct, Chesapeake, VA
0.17
Single-Family Home
$531,500
06/30/26
4
2.5
2,280 sqft
3440 Bernies Ct S, Chesapeake, VA
0.34
Single-Family Home
$367,950
10/30/25
4
2.5
1,688 sqft
4208 Pineridge Ct, Chesapeake, VA
0.27
Single-Family Home
$445,000
04/15/26
4
2.5
2,211 sqft
3428 Collins Blvd, Chesapeake, VA
0.25
Single-Family Home
$310,000
09/29/25
3
1.5
1,416 sqft
4211 Redfern Ln, Chesapeake, VA
0.18
Single-Family Home
$409,900
05/14/26
3
2
1,416 sqft
3360 Brandywine Dr, Chesapeake, VA
0.44
Single-Family Home
$310,000
10/02/25
4
2
1,713 sqft
4060 Belvedere Dr, Chesapeake, VA
0.46
Single-Family Home
$315,000
02/27/26
4
2
2,052 sqft
3352 Brandywine Dr, Chesapeake, VA
0.41
Single-Family Home
$360,000
01/15/26
4
2
1,437 sqft

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Rental Market Trends in Western Branch North

Last updated Sep 2026
Trulia Rent Estimate$2,903/mo
Average rent
$2.2K
Available listings
33
View rental market trends in Chesapeake, VA

Around this home

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

LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
Nov 25, 2025
Source: Zillow Rentals
ListingRemoved
$2,586
Nov 19, 2025
Source: Zillow Rentals
Listed For Rent
$2,586
Feb 23, 2021
Source: N/A
Sold
$290,000
Jan 10, 2021
Source: Agent Provided
Listed For Sale
$284,900
Dec 7, 2020
Source: N/A
Sold
$206,100

Frequently asked questions about 4404 Greendell Rd

  • What is 4404 Greendell Rd estimated to be worth?
    Trulia's estimated value for 4404 Greendell Rd in Chesapeake, VA is $387,900.
  • What is the price history for 4404 Greendell Rd?
    4404 Greendell Rd in Chesapeake, VA last sold for $290,000 in February 2021.
  • 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 $373K. That is up $10.02K from the prior month.
  • Does 4404 Greendell Rd have air conditioning?
    Yes, 4404 Greendell Rd in Chesapeake, VA has air conditioning.
  • Does 4404 Greendell Rd have laundry facilities?
    Yes, 4404 Greendell Rd in Chesapeake, VA has in-unit laundry.

Homes for rent near 4404 Greendell Rd

Skip to last item
Skip to first item

Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
Skip to last item
  • Results are loading
Skip to first item