4319 Greenleaf Dr, Chesapeake, VA 23321
OFF MARKET

$717,500

Trulia Estimate
  • 5 Beds
  • 2.5 Baths
  • 2,961 sqft (on 0.83 acres)

4319 Greenleaf Dr, Chesapeake, VA 23321

Western Branch North
Est. Refi. Payment $4,398/mo*
Refinance Your Home
Currently Off Market - Sold Sep 3, 2015 for $300,000

Home Value

Trulia Estimate
$718K
Since last month
Decreased$5K (-0.8%)
Since last year
Increased$49K (+7.4%)
Since last sale
Increased$412K (+137.3%)
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 +138% in the last 10 years
MonthEstimated value
2026
September 2026$712K
August 2026$718K
July 2026$717K
June 2026$728K
May 2026$722K
April 2026$711K
March 2026$706K
February 2026$685K
January 2026$662K
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
4257 Meadow Wood Dr, Chesapeake, VA
0.27
Single-Family Home
$300,000
05/05/26
4
2.5
2,621
3000 Miars Grn, Chesapeake, VA
0.08
Single-Family Home
$965,000
09/01/26
5
5
4,680
2800 Ashwood Dr, Chesapeake, VA
0.25
Single-Family Home
$503,500
01/23/26
4
2.5
2,381
4333 Munford Ln, Chesapeake, VA
0.52
Single-Family Home
$560,000
01/02/26
5
3
3,158
2829 Meadow Wood Dr W, Chesapeake, VA
0.40
Single-Family Home
$399,900
12/19/25
4
2
2,300
2717 N Elizabeth Harbor Dr, Chesapeake, VA
0.45
Single-Family Home
$360,000
07/10/26
4
2.5
1,774
4219 Foxxglen Run, Chesapeake, VA
0.20
Single-Family Home
$830,000
09/09/26
4
3.5
4,120
2829 Meadow Wood Dr E, Chesapeake, VA
0.40
Single-Family Home
$440,000
11/07/25
4
2
2,301
4407 McCaan Quay, Chesapeake, VA
0.32
Single-Family Home
$625,000
07/17/26
3
3.5
3,499
4208 McKenna Close, Chesapeake, VA
0.21
Single-Family Home
$679,000
10/07/25
5
4.5
4,100

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
2836 Greenwood Road, Chesapeake, VA 23321
0.09
$446,400
3
2
1,997
Off Market
3000 Miars Grn, Chesapeake, VA 23321
0.08
$965,000
5
5
4,680
Recently Sold
2816 Ashwood Dr, Chesapeake, VA 23321
0.17
$574,700
5
3.5
2,870
Off Market
2848 Meadowview Rd, Chesapeake, VA 23321
0.16
$420,000
3
2
1,713
Recently Sold
4208 McKenna Close, Chesapeake, VA 23321
0.21
$702,800
5
4.5
4,100
Off Market
4219 Foxxglen Run, Chesapeake, VA 23321
0.20
$830,000
4
3.5
4,120
Recently Sold
2801 Ashwood Dr, Chesapeake, VA 23321
0.25
$490,000
4
2.5
2,315
Recently Sold
2800 Ashwood Dr, Chesapeake, VA 23321
0.25
$503,500
4
2.5
2,381
Recently Sold
4212 McKenna Close, Chesapeake, VA 23321
0.22
$733,000
5
3.5
3,782
Recently Sold
2860 Greenview Rd, Chesapeake, VA 23321
0.23
$635,000
5
3.5
3,643
For Sale
4248 Meadowridge Drive, Chesapeake, VA 23321
0.26
$438,000
3
2
1,712
Off Market
4244 Meadow Wood Dr, Chesapeake, VA 23321
0.32
$407,500
3
2
1,805
Recently Sold

Local Information

  • Map ViewExplore the area around 4319 Greenleaf Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1970
0.83 acre lot
2,961 sqft
$242/sqft
Garage

About this House

WATERFRONT - Custom built, 1-owner home in heart of Western Branch! Approximately 3,000 sqft. of living space at the end of secluded court. Generously-sized rooms throughout, with separate living, dining, and family rooms. Two gas fireplaces on first floor . Enjoy views of Drum Point Creek (W. Elizabeth River) from large, screened-in porch. Roughly 280' of shoreline along navigable tidal stream. Oversized 2-car garage. Alarm system. Neighborhood pool and boat slip with NO POA fees!
4319 Greenleaf Dr, Chesapeake, VA 23321 is a 5 bedroom, 3 bathroom, 2,961 sqft single-family home in Western Branch North, built in 1970. It last sold for $300,000 on Sep 3, 2015. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $717,500, with a rent estimate of $3,374/month.

Home Details for 4319 Greenleaf Dr

Interior Features

Levels, Entrance, & Accessibility
Stories: 2
Interior Details
AtticTypes of Rooms: Walk In Closet
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Heating & Cooling
Air Conditioning
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Vinyl, BrickFoundation Type: Other
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1970Year Updated: 2016
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.83 acres

Price and Tax history

DateEventPrice
Sep 3, 2015
Source: N/A
Sold
$300,000
Aug 14, 2015
Source: Agent Provided
PriceChange
$349,500
Price decreased by 2%
Jul 17, 2015
Source: Agent Provided
PriceChange
$354,900
Price decreased by 3%
Jul 6, 2015
Source: Agent Provided
PriceChange
$364,900
Price decreased by 1%
Jun 23, 2015
Source: Agent Provided
PriceChange
$369,900
Price decreased by 1%

Market trends in Western Branch North

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$360K
$13.15KMoM
Sale-to-List Price
100.1%
Price per sq ft
$200
$0MoM
Available listings
110
22MoM

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

Frequently asked questions about 4319 Greenleaf Dr

  • What is 4319 Greenleaf Dr estimated to be worth?
    Trulia's estimated value for 4319 Greenleaf Dr in Chesapeake, VA is $717,500.
  • What is the price history for 4319 Greenleaf Dr?
    4319 Greenleaf Dr in Chesapeake, VA last sold for $300,000 in September 2015.
  • 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 $360K. That is down $13.15K from the prior month.
  • Does 4319 Greenleaf Dr have laundry facilities?
    Yes, 4319 Greenleaf Dr in Chesapeake, VA has in-unit laundry.
  • How big is the lot at 4319 Greenleaf Dr?
    The lot at 4319 Greenleaf Dr in Chesapeake, VA is about 0.83 acres (36,154 sq ft).

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