4501 Windward Dr, Chester, VA 23831
OFF MARKET

$350,700

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,755 sqft (on 0.43 acres)

4501 Windward Dr, Chester, VA 23831

Est. Refi. Payment $2,084/mo*
Refinance Your Home
Currently Off Market - Sold Nov 30, 2022 for $275,000

Home Value

Trulia Estimate
$351K
Since last month
Increased$600 (+0.2%)
Since last year
Increased$11K (+3.2%)
Since last sale
Increased$76K (+27.7%)
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 +92% in the last 10 years
MonthEstimated value
2026
August 2026$351K
August 2026$351K
July 2026$351K
June 2026$356K
May 2026$357K
April 2026$357K
March 2026$350K
February 2026$345K
January 2026$337K
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
4512 Greenbriar Dr, Chester, VA
0.09
Single-Family Home
$333,958
07/10/26
3
2
2,204
4603 Edenton Pl, Chester, VA
0.31
Single-Family Home
$280,001
04/20/26
3
2
1,881
4400 Treely Rd, Chester, VA
0.24
Single-Family Home
$310,000
08/20/26
3
1.5
1,643
15090 Horseshoe Bend Dr, Chester, VA
0.19
Single-Family Home
$359,000
09/12/25
3
2
1,332
4221 Whitebirch Dr, Chester, VA
0.23
Single-Family Home
$380,000
08/17/26
3
2
1,896
4401 Greenbriar Dr, Chester, VA
0.15
Single-Family Home
$389,900
02/02/26
4
2
1,924
15100 Horseshoe Bend Dr, Chester, VA
0.21
Single-Family Home
$157,150
09/15/25
3
2
1,914
4510 Edenton Pl, Chester, VA
0.34
Single-Family Home
$321,100
10/17/25
3
2.5
1,716
4608 Edenton Pl, Chester, VA
0.38
Single-Family Home
$400,000
05/07/26
3
2
2,121
15050 Horseshoe Bend Dr, Chester, VA
0.12
Single-Family Home
$377,775
01/29/26
5
3
2,536

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
4509 Windward Dr, Chester, VA 23831
0.04
$390,600
3
2
2,148
Off Market
4511 Greenbriar Dr, Chester, VA 23831
0.08
$415,700
5
2
2,391
Off Market
4515 Greenbriar Dr, Chester, VA 23831
0.09
$390,600
3
2
1,769
Off Market
4605 Greenbriar Dr, Chester, VA 23831
0.13
$367,900
3
2
1,200
Recently Sold
15050 Horseshoe Bend Dr, Chester, VA 23831
0.12
$377,775
5
3
2,536
Recently Sold
4612 Greenbriar Dr, Chester, VA 23831
0.16
$306,800
3
2
1,296
Off Market
4419 Overridge Dr, Chester, VA 23831
0.16
$337,900
3
1.5
1,494
Off Market
15060 Horseshoe Bend Dr, Chester, VA 23831
0.14
$414,000
4
3
3,024
Off Market
4401 Greenbriar Dr, Chester, VA 23831
0.15
$389,900
4
2
1,924
Recently Sold
15080 Horseshoe Bend Dr, Chester, VA 23831
0.17
$345,800
3
2
1,539
Off Market
4601 Overridge Dr, Chester, VA 23831
0.21
$340,100
4
2
1,808
Off Market
15090 Horseshoe Bend Dr, Chester, VA 23831
0.19
$371,800
3
2
1,332
Off Market

Local Information

  • Map ViewExplore the area around 4501 Windward Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1974
0.43 acre lot
1,755 sqft
$200/sqft

About this House

What a cutie! With 3 bedrooms, 2 FULL BATHROOMS JUST RECENTLY PAINTED, a screened in porch, big backyard with firepit AND carport on large lot, this home offers GREAT living space both inside and out! Both the roof and HVAC have been replaced, along with the fresh paint and carpet! With the bigger items taken care of, you can focus on adding your own creativity to making this cute rancher, your home!
4501 Windward Dr, Chester, VA 23831 is a 3 bedroom, 2 bathroom, 1,755 sqft single-family home built in 1974. It last sold for $275,000 on Nov 30, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $350,700, with a rent estimate of $2,447/month.

Home Details for 4501 Windward Dr

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Carpet
Interior Details
Number of Rooms: 7
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Composition, OtherDeckExterior: BrickPorch
Parking & Garage
Parking: Carport

Property Information

Year Built
Year Built: 1974
Property Type / Style
Property Type: Single Family HomeArchitecture: traditional

Community

Units in Building: 1

Lot Information

Lot Area: 0.43 acres

Price and Tax history

DateEventPrice
Nov 30, 2022
Source: CVRMLS #2223239
Sold
$275,000
Oct 25, 2022
Source: CVRMLS #2223239
Pending
$275,000
Sep 22, 2022
Source: CVRMLS #2223239
PriceChange
$275,000
Price decreased by 5%
Sep 8, 2022
Source: CVRMLS #2223239
PriceChange
$289,000
Price decreased by 3%
Aug 29, 2022
Source: CVRMLS #2223239
Listed For Sale
$297,000

Market trends in Chester

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$381K
$8KMoM
Sale-to-List Price
100.0%
Price per sq ft
$194
$0MoM
Available listings
167
16MoM

Around this home

What Locals Say about Chester

At least 304 Trulia users voted on each feature.

  • 90 % Say car is needed

  • 89 % Say it's dog friendly

  • 85 % Say parking is easy

  • 80 % Say there's holiday spirit

  • 80 % Say yards are well-kept

  • 73 % Say it's quiet

  • 68 % Say kids play outside

  • 60 % Say people would walk alone at night

  • 51 % Say neighbors are friendly

  • 49 % Say they plan to stay for at least 5 years

  • 44 % Say there's wildlife

  • 37 % Say there are sidewalks

  • 37 % Say streets are well-lit

  • 27 % Say it's walkable to restaurants

  • 26 % Say it's walkable to grocery stores

  • 24 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Emekaogbodo420
    "Chester is a safe place to raise children. "
    0
    Flag
  • Thinking N Growing
    "I was born into Chester back in the day (smile). Even back then I always felt safe and respected. While I left for many years, I returned to the same safe environment."
    0
    Flag
  • Omi Ouyang
    "its used have a lot of retired people lived here now are more middle age ppls moved to this area for kids education. Nice neighborhood. "
    0
    Flag
  • Ruby
    "Lots of people walking their dogs around and conveniente dog parks nearby that seem clean and well kept."
    0
    Flag
  • Harmonkaren1
    "Few children in this neighborhood mostly retired people. Safe in this area within the parameters of the neighborhood, occasionally police calls in the adjoining shopping area. "
    0
    Flag
  • Jonn1nsu
    "Everyone is pretty much friendly and everyone works together in some degree. Some people do wine night "
    0
    Flag
  • Deborah Cook
    "I live in this neighborhood. I like because it’s affordable and clean. It has a rural feel but only 20 minutes to the city "
    0
    Flag
  • James
    "That it’s a good place to meet other people and are nice people so you should move to Chester and that’s the truth let’s go Chester you cool place"
    0
    Flag
  • Stacey Murphy
    "Traffic is heavy at certain times during the day but it’s expected considering most military prefer to live in the area and the area is safe and has everything you need. It’s definitely a great place to raise a family. "
    0
    Flag
  • Karen.augustine4466
    "I am not at all engaged in the neighborhood activities. My work schedule is hectic and neighborhood activities are not posted centrally and often missed."
    0
    Flag
  • William L.
    "There are a lot of kids that live in this area (smaller ones) and the streets are narrow. It's is very important that we go slow and stay attentive while driving. "
    1
    Flag
  • William Larson
    "My commute is a bit longer than I should like it to be. I do mostly for my daughter to attend a better school. "
    0
    Flag
  • Trulia User
    "peace and safe area. Dog or pet friendly community. Good for middle age or young age couple to raise child from here. Got pre-k to high school fine"
    2
    Flag
  • Trulia User
    "They would like it but for us property owners we would appreciate people not letting their dogs go in our yards as it kills our grass, and flowers planted around the mailboxes and they should pick up after the dogs and not leave poop up in our yards. "
    2
    Flag
  • Trulia User
    "we have neighborhood potlucks and movie night and his real fight thank you very much this is really crazy"
    1
    Flag
  • Trulia User
    "Food trucks overall family oriented community ! The neighborhood is pretty much maintained keeping a near apperance. Amenities are pretty decent with local shopping nearby. restaurants and food shopping withing 4 to 5 miles. one of the best pools for residents as well as families. "
    0
    Flag
  • Doss
    "Very close to I-95. Can be in Richmond in 10-20 minutes depending on location. Takes about 30minutes to get to Midlothian. "
    3
    Flag
  • Sesmailka
    "We are fortunate to live and I diverse neighborhood with great schools, neighborly people, small town feel all with the accessibility of the city. We love our town."
    1
    Flag
  • Claudia G. C.
    "Dogs always are on their leash and they are well kept indoors so you can’t hear them barking too much"
    5
    Flag
  • Jonn1nsu
    "My commute to work is great and I love the restaurants that are near by. The area is kid friendly and safe "
    0
    Flag
  • Dorothy C.
    "I've lived in this neighborhood for going on 8 years and I love it hear.its nice and quite and I have always felt safe here."
    0
    Flag
  • Candace P.
    "I grew up in Chester and it is a wonderful place to grow up. The schools in Chesterfield are top notch and each high school has a certain specialty that any kid can apply to. The county is pretty diverse and I never felt unsafe growing up here. "
    0
    Flag
  • Tisu_chelu
    "The neighboring communities as well as Chester have multiple festivals, parades during Christmas and friendly for trick or treating. There are a few neighbors who are less than neighborly but mostly older retirees here."
    0
    Flag
  • Tommygunobx
    "I’ve lived here all my life. Same people for the most part which is nice to see familiar faces. Quiet and friendly. "
    0
    Flag
  • Zues5000
    "Neighbors looking out for each other. Neighnors walking and riding is done daily. Minimum to no crime reported in the neighborhood."
    0
    Flag
  • Joshua J.
    "Nice and homely place to live. Local parks and areas of j retest close but still the feeling of not being on top of each other or suppressed. "
    2
    Flag
  • Kamarimarrow123444
    "Great housing and nice schools for the kids and also the people are super nice and respectful and very clean"
    0
    Flag
  • Ummynina
    "This is a very nice and safe place to live, with a lot of up and coming new stores and great eateries"
    2
    Flag
  • Spencer P.
    "I grew up here. It is a small town but close to Richmond, Ft lee, and only 2hrs from DC. It is also a pretty good school system when I was here. Racism however is still alive. Just covert. "
    0
    Flag
  • Lisa.harrisonross
    "I lived here for 20 years. It is a great community and has lots for families. It is a nice area for meeting people."
    0
    Flag
  • Nikia P.
    "None , not sure ion any events. It’s pretty much a nice area but I have noticed more and more traffic. People need to learn to slow down around this area "
    0
    Flag
  • Katie C.
    "They would like the size of yards but would not like the lack of side walks. That makes it difficult to go on walks. "
    0
    Flag
  • Adjoa B.
    "My neighborhood is quite and safe for raising children. it also has to rated schools in Chesterfield! "
    0
    Flag
  • Emily G.
    "Most people need at least one car in the household to live in the area. I have not seen public transportation stops along the road here. However with modern conveniences it is getting easier and easier to get around. "
    0
    Flag
  • Savanahncummings
    "I drive my truck everywhere I go. Walking is plausible but I don’t do it much. No trains for travel and the airport is too far. No buses either. "
    2
    Flag
  • Morgen C.
    "Haloween is wonderful here as so many children from the neighborhood and surrounding area come out and have a night of fun here! Low traffic in the neighborhoods makes for a mich safer trick or treating spot than others"
    0
    Flag
  • Linda O.
    "Its quiet. We watch out for each other and our children and pets. Children and dogs are regularly out walking and playing. We have sweet kitties in the neighborhood too that love being petted."
    0
    Flag
  • Annie M
    "There are no sidewalks, no dog park or community common area readily accessible, and neighbors tend to drive fast on neighborhood roads"
    2
    Flag
  • Ashlynn C.
    "Lots of dog walkers in the neighborhood and everyone is friendly.. everyone picks up after their dogs "
    0
    Flag
  • B s. C.
    "The roads are very quiet and every street has plenty of wooded areas. Large neighborhood with minimal traffic. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 4501 Windward Dr

  • What is 4501 Windward Dr estimated to be worth?
    Trulia's estimated value for 4501 Windward Dr in Chester, VA is $350,700.
  • What is the price history for 4501 Windward Dr?
    4501 Windward Dr in Chester, VA last sold for $275,000 in November 2022.
  • Is Chester a buyer's or seller's market?
    Chester is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Chester?
    The median sale price in Chester is $381K. That is up $8K from the prior month.
  • Does 4501 Windward Dr have air conditioning?
    Yes, 4501 Windward Dr in Chester, VA has air conditioning.
  • How big is the lot at 4501 Windward Dr?
    The lot at 4501 Windward Dr in Chester, VA is about 0.44 acres (18,949 sq ft).

Explore by feature - Pet Friendly

34 pet-friendly rentals in Chester, VA

Explore by feature - Garage

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Explore by feature - Air Conditioning

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Explore by feature - Pool

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Explore by feature - Washer/dryer

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Explore by feature - Outdoor Space

6 rentals with an outdoor space in Chester, VA

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Off Market Homes Near 4501 Windward Dr

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