523 Windward Dr, Chesapeake, VA 23320
OFF MARKET

$461,900

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 1,916 sqft

523 Windward Dr, Chesapeake, VA 23320

Greenbrier East
Est. Refi. Payment $2,720/mo*
Refinance Your Home
Currently Off Market - Sold Jul 26, 2013 for $279,000

Home Value

Trulia Estimate
$462K
Since last month
Decreased$2K (-0.3%)
Since last year
Increased$3K (+0.7%)
Since last sale
Increased$184K (+65.8%)
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 +68% in the last 10 years
MonthEstimated value
2026
August 2026$463K
July 2026$464K
June 2026$468K
May 2026$471K
April 2026$470K
March 2026$462K
February 2026$458K
January 2026$452K
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
717 Gulfwind Rd, Chesapeake, VA
0.12
Single-Family Home
$452,500
12/12/25
4
2.5
2,162
520 Windward Dr, Chesapeake, VA
0.03
Single-Family Home
$405,000
05/18/26
3
2
1,665
903 Lee Shore Ct, Chesapeake, VA
0.09
Single-Family Home
$509,000
12/16/25
3
2.5
2,184
709 Gulfwind Rd, Chesapeake, VA
0.13
Single-Family Home
$470,000
09/12/25
3
2.5
2,108
929 Thatcher Way, Chesapeake, VA
0.44
Single-Family Home
$458,000
06/15/26
4
2.5
2,166
910 Brandon Quay, Chesapeake, VA
0.46
Single-Family Home
$412,000
09/03/25
4
3
2,256
828 Cranston Dr, Chesapeake, VA
0.26
Single-Family Home
$485,000
05/22/26
4
3
1,664
928 Wynngate Dr, Chesapeake, VA
0.26
Single-Family Home
$415,000
09/23/25
3
2.5
1,600
1103 Woodsmans Ct, Chesapeake, VA
0.51
Single-Family Home
$446,000
06/09/26
4
2.5
2,217
426 Blue Beech Way, Chesapeake, VA
0.46
Single-Family Home
$435,000
09/02/25
3
2.5
2,352

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
527 Windward Dr, Chesapeake, VA 23320
0.02
$498,000
4
2.5
2,100
For Sale
800 Broad Reach Rd, Chesapeake, VA 23320
0.05
$475,000
3
2.5
2,383
For Sale
519 Windward Dr, Chesapeake, VA 23320
0.02
$425,000
4
3.5
2,595
Recently Sold
526 Windward Dr, Chesapeake, VA 23320
0.04
$290,000
3
2.5
1,471
For Sale
903 Lee Shore Ct, Chesapeake, VA 23320
0.09
$509,000
3
2.5
2,184
Recently Sold
602 Windward Dr, Chesapeake, VA 23320
0.08
$475,000
4
2.5
2,100
For Sale
900 Lee Shore Ct, Chesapeake, VA 23320
0.11
$538,097
4
2.5
2,226
Recently Sold
717 Gulfwind Rd, Chesapeake, VA 23320
0.12
$452,500
4
2.5
2,162
Recently Sold
709 Gulfwind Rd, Chesapeake, VA 23320
0.13
$487,900
3
2.5
2,108
Off Market
500 Judah Way #124, Chesapeake, VA 23320
0.17
$277,500
2
2.5
1,563
Recently Sold
500 Judah Way #123, Chesapeake, VA 23320
0.17
$259,900
2
2
1,215
For Sale
140 Springer Ln #232, Chesapeake, VA 23320
0.17
$278,000
2
2.5
1,642
Recently Sold

Local Information

  • Map ViewExplore the area around 523 Windward Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1995
Living Area
1,916 sqft
Price/Sqft
$241
Parking
Garage

About this House

Freshly painted throughout * All new light fixtures * Stainless steel appliances in 2012 * Updated kitchen & baths * Fenced backyard * 9' ceilings on 1st floor * wired for surround sound in FR*Vaulted ceiling & 3 closets in mstr bdrm*Fun Forest Playground,dog walk,Ches. city, easy interstate access
523 Windward Dr, Chesapeake, VA 23320 is a 4 bedroom, 3 bathroom, 1,916 sqft single-family home in Greenbrier East, built in 1995. It last sold for $279,000 on Jul 26, 2013. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $461,900, with a rent estimate of $2,817/month.

Home Details for 523 Windward Dr

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet, Laminate
Interior Details
AtticNumber of Rooms: 8Ceiling Fan
Appliances & Utilities
Cable ReadyDishwasherDisposalMicrowave
Fireplace & Spa
Fireplace
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: VinylFoundation Type: SlabPatio
Parking & Garage
GarageParking Space: 1Parking: Garage Attached

Property Information

Year Built
Year Built: 1995
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 5227 sqft

Price and Tax history

DateEventPrice
Jul 26, 2013
Source: N/A
Sold
$279,000
Apr 23, 2013
Source: Agent Provided
Listed For Sale
$283,500
Nov 1, 2012
Source: N/A
Sold
$281,400
Mar 22, 2010
Source: Agent Provided
ListingRemoved
$269,000
Sep 19, 2009
Source: Agent Provided
PriceChange
$269,000
Price decreased by 4%

Market trends in Greenbrier East

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$403K
$2.08KMoM
Sale-to-List Price
100.1%
0.1%MoM
Price per sq ft
$223
$1MoM
Available listings
114
11MoM

Around this home

Neighborhood Overview

Greenbrier East
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Greenbrier East

At least 321 Trulia users voted on each feature.

  • 94 % Say it's dog friendly

  • 88 % Say car is needed

  • 88 % Say parking is easy

  • 78 % Say there are sidewalks

  • 74 % Say it's quiet

  • 73 % Say streets are well-lit

  • 73 % Say there's holiday spirit

  • 72 % Say people would walk alone at night

  • 70 % Say yards are well-kept

  • 68 % Say kids play outside

  • 56 % Say they plan to stay for at least 5 years

  • 53 % Say it's walkable to restaurants

  • 52 % Say neighbors are friendly

  • 49 % Say it's walkable to grocery stores

  • 40 % Say there's wildlife

  • 28 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Sophia.anne.molina
    "Some days there is bad traffic and others it’s smooth. I find that compared to other cities it’s decent. I would describe my commute as fair compared to living in Portsmouth or Norfolk or Virginia Beacb. My commute is anywhere from 5 minutes to 35 minutes from my place of residence. That’s all I would say. "
    0
    Flag
  • Shirley Belue
    " The is a family oriented community. There are schools and parks to get walks for health. Many neighbors have dogs and cats. There are no sidewalks, just a two lane road. "
    1
    Flag
  • stampwithsharon
    "Excellent book club! Neighbors are very friendly. Quiet neighbors,nice pool. Walkable to grocery, restaurants and library. "
    0
    Flag
  • M2jfr2k9vs
    "Motor vehicles are the ultimate way to travel, they’re so convenient! I highly recommend getting or having a vehicle!!!"
    1
    Flag
  • 94zw848pdw
    "Not too bad. I get to work within 20 minutes with minimal traffic. Not sure what else to say about it"
    2
    Flag
  • Kclynncarlisle
    "Pizza party’s, barbecues, trick or treating, thanksgiving potlucks, back porch hang outs, pool party’s. "
    0
    Flag
  • Colpotitoli
    "Nice safe clean friendly close to all shopping center urgent care and other hospitals are very close "
    1
    Flag
  • Trulia User
    "There are always dogs being walked and playing in the field by my apartment with their owners. It is a very dog friendly area and the owners are polite and kind and courteous of other dogs as well as people who live around here without dogs. "
    1
    Flag
  • Trulia User
    "Great community, Friendly , quiet , kid friendly. Lived here all of my life and have never had issues or problems. "
    0
    Flag
  • Trulia User
    "I've lived here and love it I would recommend everyone to live here .I'm so ready To live in this area again "
    2
    Flag
  • Trulia User
    "There are no events at our apartment complex or the 2 next to ours. The mall is dieing. I do love the craft fair at the park. I hope next year it is bigger with more information on what our city has to offer. I miss the pow wows the park had. it is a good reminder of the Native American heritage. "
    0
    Flag
  • Trulia User
    "They would definitely not like people not picking up after their dogs They’ll love walking their dog around the neighborhood "
    0
    Flag
  • Rachelrb
    "This neighborhood is the perfect place to raise a family.It’s beautiful, safe, and extremely fun for kids! "
    13
    Flag
  • Ken L.
    "Close to everything. Very friendly people, and nice area. Schools are great. I went to Oscar Smith for a year, and while there teachers truly pushed me."
    5
    Flag
  • Sharlene R.
    "As there many dog owners in the neighbor. A lot of dog lovers within the communities. Must be careful as Bishopstokes is a race trap "
    7
    Flag
  • Littlesugarmom
    "Great area to raise kids, family oriented area. Great parks and trails. Lots to do and close proximity to everything necessary "
    1
    Flag
  • Stephaniestout94
    "Quiet neighborhood. A lot of families. Close to everything. Food entertainment , shopping, dog parks. "
    2
    Flag
  • Katelyn W.
    "There’s plenty of areas to walk your dog. Sidewalks, parks, lots of trees. Most places have fences and yards or are pet friendly apartments. "
    0
    Flag
  • Carrie J.
    "it's nice and quite yet close to anything you could possibly need or want. I have lived here for 2 years and love the area."
    4
    Flag
  • Ashley D.
    "Quiet and safe. Right next to a school and a mall which is hard to find. The cops monitor the neighbor and make sure speeding is kept to a minimum."
    12
    Flag
  • Karena P.
    "It’s a great place to live, especially if you have a young family! Great schools, and great for pets! "
    0
    Flag
  • Ash M.
    "Great neighborhood with great restaurants and shopping within 5 miles radius. Very safe with sidewalks pretty much everywhere."
    3
    Flag
  • Ahagenbucher182
    "I love this area so much. It’s such a great place to raise of family!!! :) Greenbrier East is the best! "
    0
    Flag
  • A.brown2134
    "It’s a great place to raise your family. I would recommend this area to anyone looking for a nice, friendly, quiet atmosphere "
    1
    Flag
  • Rebecca B.
    "Although there are areas to play between our patios and the white sticks indicating the golf course property, children do not play back there. The only time I’ve ever seen children play in the area that is available and allowed is wintertime when snow is on the grounds."
    0
    Flag
  • Brittany B.
    "Been around this neighborhood for a while. Very family friendly. Love the area in general. Great place to raise a family."
    3
    Flag
  • Fw
    "I love it here! Neighborhood is nice and quiet. Streets are always clean, very convenient to shopping, I always feel safe here. "
    0
    Flag
  • Don7likeu
    "This is a great place to live. There are many shops nearby and great schools. I have been here for two years and don't plan on moving to a different area any time soon."
    0
    Flag
  • Lpierce4511
    "I've loved in this neighborhood for 4 years. It's close to shopping and interstates making it easy to travel. I've always felt very safe in this area. I love the lake and walking path!"
    4
    Flag
  • Rebekah MO
    "This is a wonderful neighborhood, everyone is so friendly and close to everything! I would highly recommend this area to anyone! "
    0
    Flag
  • Rosario36@yahoo.com
    "Cooks outs, sharing info, schools, friends, scenery, hospitality, clean, pool, fun, picnics, and parties "
    0
    Flag
  • Fabian O.
    "Great area to live in. Everything you could ever need is within 10 to 15 minutes driving would recommend to anyone"
    0
    Flag
  • Marlena S.
    "Dog owners would love that 4 Paws, PetSmart, Barker and open dog parks are literally down the street"
    0
    Flag
  • Amy B.
    "My neighborhood is 100% dog friendly. People are always out walking their dogs. There is also a dog park around the corner at Chesapeake City Park "
    0
    Flag
  • KC
    "I’ve lived here for six months now, the area is great for going on runs and walks, my neighbors are friendly and the area is clean. There’s a lake nearby and plenty of shopping for anything you need within minutes of your house."
    9
    Flag
  • Gellinabaez
    "Dogs in the Greenbrier area seem to be friendly and well-trained; I never hear loud, constant barking. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 523 Windward Dr

  • What is 523 Windward Dr estimated to be worth?
    Trulia's estimated value for 523 Windward Dr in Chesapeake, VA is $461,900.
  • What is the price history for 523 Windward Dr?
    523 Windward Dr in Chesapeake, VA last sold for $279,000 in July 2013.
  • 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 $403K. That is down $2.08K from the prior month.
  • Does 523 Windward Dr have air conditioning?
    Yes, 523 Windward Dr in Chesapeake, VA has air conditioning.
  • How big is the lot at 523 Windward Dr?
    The lot at 523 Windward Dr in Chesapeake, VA is about 0.12 acres (5,227 sq ft).

Explore by feature - Pet Friendly

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Off Market Homes Near 523 Windward Dr

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