2020 Windy Road, Chesapeake, VA 23324
OFF MARKET

$376,500

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 1,681 sqft

2020 Windy Road, Chesapeake, VA 23324

Indian River
Est. Refi. Payment $2,355/mo*
Refinance Your Home
Currently Off Market - Sold May 2, 2025 for $357,000

Home Value

Trulia Estimate
$377K
Since last month
Increased$1K (+0.3%)
Since last year
Increased$13K (+3.6%)
Since last sale
Increased$20K (+5.5%)
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 +93% in the last 10 years
MonthEstimated value
2026
September 2026$377K
August 2026$376K
July 2026$375K
June 2026$375K
May 2026$376K
April 2026$375K
March 2026$373K
February 2026$367K
January 2026$366K
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
3020 Armentrout Ct, Chesapeake, VA
0.08
Single-Family Home
$404,900
02/10/26
4
2.5
1,937
2111 Stalham Rd, Chesapeake, VA
0.12
Single-Family Home
$380,000
01/16/26
4
2.5
1,826
2836 Parkside Dr, Chesapeake, VA
0.11
Single-Family Home
$360,000
10/22/25
3
2.5
1,746
2004 Windy Rd, Chesapeake, VA
0.06
Single-Family Home
$390,000
02/06/26
3
2.5
1,472
3017 Bill Reid Ct, Chesapeake, VA
0.06
Single-Family Home
$305,000
06/09/26
3
2.5
1,776
2915 Berkley Ave, Chesapeake, VA
0.17
Single-Family Home
$391,900
10/16/25
3
2.5
1,656
2932 Sunrise Ave, Chesapeake, VA
0.30
Single-Family Home
$358,000
02/11/26
4
2.5
1,940
328 Velva Dr, Chesapeake, VA
0.27
Single-Family Home
$342,500
07/17/26
4
2
1,421
610 Mooney Rd, Chesapeake, VA
0.28
Single-Family Home
$400,000
05/15/26
4
2.5
2,040
204 Velva Dr, Chesapeake, VA
0.17
Single-Family Home
$310,000
06/22/26
3
2
1,327

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
3020 Armentrout Ct, Chesapeake, VA 23324
0.08
$404,900
4
2.5
1,937
Recently Sold
3017 Bill Reid Ct, Chesapeake, VA 23324
0.06
$305,000
3
2.5
1,776
Recently Sold
2004 Windy Rd, Chesapeake, VA 23324
0.06
$390,000
3
2.5
1,472
Recently Sold
2836 Parkside Dr, Chesapeake, VA 23324
0.11
$372,800
3
2.5
1,746
Off Market
2111 Stalham Rd, Chesapeake, VA 23324
0.12
$380,000
4
2.5
1,826
Recently Sold
2918 Berkley Ave, Chesapeake, VA 23325
0.14
$249,000
3
2
1,305
For Sale
2916 Berkley Ave, Chesapeake, VA 23325
0.15
$235,000
3
1
950
Recently Sold
2923 Berkley Ave, Chesapeake, VA 23325
0.15
$300,000
3
2
1,155
Recently Sold
708 Stalham Rd, Chesapeake, VA 23325
0.16
$270,000
3
1
1,309
Recently Sold
2917 Berkley Ave, Chesapeake, VA 23325
0.16
$289,900
3
1
900
For Sale
1403 Algona Rd, Chesapeake, VA 23324
0.21
$290,000
4
1.5
1,430
For Sale

Local Information

  • Map ViewExplore the area around 2020 Windy Road.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2003
1,681 sqft
$224/sqft
Attached Garage

About this House

Come see 2020 Windy Rd today! This Home has been very well maintained! The Living Room is perfectly Cozy for Hanging Out and Entertaining and you can Bask in the Sunlight in the Kitchen and Dining Room area while you're making enjoying your favorite meal. With 4 Bedrooms 2.5 Baths, there will be enough room for everyone. Home is positioned on a lovely corner lot next to a cul-de-sac near the park! Home comes complete with SS Appliances, Custom Backsplash and Custom Hall Tree! Home is only 15 minutes from Shopping Dinning in The Greenbriar Area!
2020 Windy Road, Chesapeake, VA 23324 is a 4 bedroom, 1,681 sqft single-family home in Indian River, built in 2003. It last sold for the $357,000 asking price on May 2, 2025. More recently, it was listed as a rental in March 2015 with an asking price of $1,350 per month. That rental listing was removed on June 28, 2016. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $376,500, with a rent estimate of $2,451/month.
Last check for updates: about 4 hours ago
Listed by Joshua Chilton
EXP Realty LLC
Source: eXp Realty, MLS#10573951

Home Details for 2020 Windy Road

Interior Features

Heating & Cooling
Heating: Electric, Heat PumpAir ConditioningCooling System: Central Air, Heat PumpHeating Fuel: Electric
Levels, Entrance, & Accessibility
Stories: 2Floors: Carpet, Ceramic, Vinyl
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: AsphaltFoundation Type: Slab
Parking & Garage
GarageParking: Garage Att 1 Car Driveway Spc Street, Garage Attached

Property Information

Year Built
Year Built: 2003
Property Type / Style
Property Type: Single Family HomeArchitecture: Traditional, Transitional

Price and Tax history

DateEventPrice
May 2, 2025
Source: N/A
Sold
$357,000
Mar 28, 2025
Source: REIN Inc. #10573951
Contingent
$350,000
Mar 14, 2025
Source: REIN Inc. #10573951
Listed For Sale
$350,000
Feb 25, 2022
Source: N/A
Sold
$307,500
Feb 1, 2022
Source: REIN Inc. #10419589
PriceChange
$306,000
Price increased by 8%

Market trends in Indian River

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$324K
$13.33KMoM
Sale-to-List Price
100.2%
0.1%MoM
Price per sq ft
$219
$9MoM
Available listings
96
2MoM

Around this home

Neighborhood Overview

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

What Locals Say about Indian River

At least 259 Trulia users voted on each feature.

  • 87 % Say car is needed

  • 82 % Say it's dog friendly

  • 75 % Say parking is easy

  • 75 % Say kids play outside

  • 74 % Say yards are well-kept

  • 67 % Say there's holiday spirit

  • 64 % Say it's quiet

  • 55 % Say streets are well-lit

  • 54 % Say neighbors are friendly

  • 51 % Say people would walk alone at night

  • 47 % Say they plan to stay for at least 5 years

  • 46 % Say there are sidewalks

  • 41 % Say there's wildlife

  • 32 % Say it's walkable to restaurants

  • 32 % Say it's walkable to grocery stores

  • 20 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Evangalawton.agiwc
    "I have lived in this neighborhood for about 3 years and it’s friendly and open for the most part. Very few issues here."
    0
    Flag
  • Jyroaz06
    "I’ve lived here for two years. There plenty of things to do with your family. I love it here. I’ll will definitely recommend Chesapeake, VA to my family, and friends."
    0
    Flag
  • Jyroaz06
    "Easy to travel in the roads, no traffic jams. You barely hear any police activity in the neighborhood."
    0
    Flag
  • Karen
    "A lot of families in our neighborhood. No sidewalks and streets are skinny but alot of parents with kids on bikes and dog walkers. Great neighborhood. Love it. "
    0
    Flag
  • Karen
    "Lived here all my 63 years of life. Love it here. A lot of kids riding bikes. Families at the many parks. "
    0
    Flag
  • Tyreed777
    "i’ve loved in this neighborhood for about 20 years. i love this neighborhood, it’s relatively quiet and i love going on walks around the neighborhood. everyone is friendly!"
    0
    Flag
  • Trulia User
    "Everyone is very friendly. And everything that you may need, its right around the corner, including the interstate. Right in the middle of Chesapeake, the heart of Virginia. "
    1
    Flag
  • Trulia User
    "Some bark constantly due to being left outside often early morning and later evening but everywhere most pick up after their dog but you have the exception "
    5
    Flag
  • Trulia User
    "The neighborhood is very dog friendly and they also have breeders available to. Plenty of dog parks."
    0
    Flag
  • Trulia User
    "I don't live in that area, I live in Chesapeake, it's just gotten expensive to live here. I'm looking for a nice neighborhood in Norfolk, I like to look at the crime rate while I'm visiting this site. my neighborhood is safe, and friendly, with lots of dogs but folks take care of their pets"
    2
    Flag
  • N'kosi P.
    "Tons of trails to walk your dogs on and most have doggy bags attached to posts at the start of trails"
    2
    Flag
  • Trulia User
    "This a dog friendly neighborhood. Pups will love the doggie park along with the friendly owner. Clean neighborhood considering the amount of dogs whom live here. "
    2
    Flag
  • Helen B.
    "This is a very quiet kid freindly neighborhood , the schools are great.the neighborhood is mixed as far as race.Everyone would help if needed.From what I have heard the schools are great for this area.Propertys are well kept and I have seen people pick up after there animals when neccisary."
    8
    Flag
  • Shelby.appleman
    "I work at naval station Oceana and my drive is only about 20 minutes every morning. It is only approximately 20 minutes away from naval station Norfolk as well. "
    5
    Flag
  • Lorenzo W.
    "I was just visiting but the area looks fine the people an theirs pets was awesome The dogs wasn't to scary for my youngest children "
    1
    Flag
  • Jason P.
    "Block party a few times in summer. Trick or treat is awesome. Quiet neighborhood almost every day of the year. "
    2
    Flag
  • Kat3869
    "All the neighbors are very sweet. A lot of us get together on July 4th. There’s lot of children and all the kids play together. All around nice neighborhood. "
    1
    Flag
  • Arghpiratejen
    "I feel safe and happy here. I don’t know of much events though but being there is a pool and clubhouse I imagine there are things "
    0
    Flag
  • Nadia B.
    "I've lived in this neighborhood for 7 years. I think the neighbors are nice and if you need them they are there. The location is prime with all schools sk your child can go from Prek to graduating all in one area. "
    21
    Flag
  • Ejsuggs
    "The people are very friendly to their neighbors and surrounding. It is a very nice neighborhood to raise your family."
    0
    Flag
  • Jodywilliams.hokie
    "This is a transition neighborhood. Older homes, some in good shape, some not so good. new home being built but with very small yards."
    1
    Flag
  • Robert Pretlow
    "Ive lived in Norfolk Highlands my whole life. Love the area. Love the people around here. Convenience is great love the apartment and ready to move in"
    5
    Flag
  • Tanisha W. .
    "We are centrally located to the the major highways and public transportation. Great neighborhood, friendly neighbors and great shopping nearby. "
    0
    Flag
  • johnnycab23513
    "I just moved into the neighborhood December 29th. It is quiet and the streets are well lit. The neighbors seem nice, and I am looking forward to becoming acquainted when it warms up. The house I bought is great!"
    10
    Flag
  • Sandra M.
    "People walk their dogs all the time and any lost dogs get taken in by the neighbors and the community searches out the owners."
    1
    Flag
  • Real T.
    "nothing it is too close together, no sidewalks. I plan to move from here in the next 2 years. There is nothing special about this neighborhood. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 2020 Windy Road

  • What is 2020 Windy Road estimated to be worth?
    Trulia's estimated value for 2020 Windy Road in Chesapeake, VA is $376,500.
  • What is the price history for 2020 Windy Road?
    2020 Windy Road in Chesapeake, VA last sold for $357,000 in May 2025.
  • 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 $324K. That is up $13.33K from the prior month.
  • Does 2020 Windy Road have air conditioning?
    Yes, 2020 Windy Road in Chesapeake, VA has air conditioning.
  • Does 2020 Windy Road have laundry facilities?
    Yes, 2020 Windy Road in Chesapeake, VA has in-unit laundry.

Explore by feature - Pet Friendly

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Explore by feature - Outdoor Space

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Apartments for Rent

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Off Market Homes Near 2020 Windy Road

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