534 Windward Dr, Chesapeake, VA 23320
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Property image
OFF MARKET

534 Windward Dr
Chesapeake, VA 23320

Greenbrier East
  • 4 Beds
  • 3 Baths
  • 2,026 sqft

$433,900

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $2,585/mo*
Refinance Your Home

$433,900

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $2,585/mo*
Refinance Your Home
4 Beds
3 Baths
2,026 sqft

Home Value

Trulia Estimate
$434K
Since last month
$200 (0%)
Since last year
Increased$6K (+1.4%)
Since last sale
Increased$136K (+45.5%)
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 +53% in the last 10 years
MonthEstimated value
2026
August 2026$434K
July 2026$433K
June 2026$440K
May 2026$443K
April 2026$439K
March 2026$435K
February 2026$433K
January 2026$428K
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
1605 Stone Moss Reach #A, Chesapeake, VA
2.34
Multi-Family Home
$206,000
04/21/26
2
2
978
1805 Rich Ct, Virginia Beach, VA
3.29
Multi-Family Home
$320,000
06/18/26
3
2
1,305
4112 Williamson St, Chesapeake, VA
3.53
Multi-Family Home
$210,000
08/13/26
5
3
2,409
340 Ewell Ln, Chesapeake, VA
3.61
Multi-Family Home
$340,000
01/30/26
4
2
1,920
2315 Smith Ave #B, Chesapeake, VA
3.74
Multi-Family Home
$260,000
08/28/25
4
2
1,538
4109 5th St, Chesapeake, VA
3.65
Multi-Family Home
$274,500
04/09/26
4
2
1,620
1518 Walnut Ave #A, Chesapeake, VA
4.49
Multi-Family Home
$260,000
11/18/25
4
2
1,593
1422 Oleander Ave #A, Chesapeake, VA
4.58
Multi-Family Home
$270,000
12/01/25
4
2
1,500
1421 Oleander Ave, Chesapeake, VA
4.61
Multi-Family Home
$250,000
11/18/25
4
2
1,749
1512 Chirnside Ct, Virginia Beach, VA
4.86
Multi-Family Home
$305,000
04/29/26
3
2
1,189

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
526 Windward Dr, Chesapeake, VA 23320
0.04
$290,000
3
2.5
1,471
For Sale
527 Windward Dr, Chesapeake, VA 23320
0.05
$498,000
4
2.5
2,100
For Sale
602 Windward Dr, Chesapeake, VA 23320
0.02
$489,900
4
2.5
2,100
For Sale
800 Broad Reach Rd, Chesapeake, VA 23320
0.06
$475,000
3
2.5
2,383
For Sale
519 Windward Dr, Chesapeake, VA 23320
0.08
$425,000
4
3.5
2,595
Recently Sold
903 Lee Shore Ct, Chesapeake, VA 23320
0.07
$509,000
3
2.5
2,184
Recently Sold
717 Gulfwind Rd, Chesapeake, VA 23320
0.07
$452,500
4
2.5
2,162
Recently Sold
900 Lee Shore Ct, Chesapeake, VA 23320
0.10
$538,097
4
2.5
2,226
Recently Sold
709 Gulfwind Rd, Chesapeake, VA 23320
0.10
$487,100
3
2.5
2,108
Off Market
1028 Austin Dr, Chesapeake, VA 23320
0.15
$497,000
4
2.5
2,339
Recently Sold
140 Springer Ln #232, Chesapeake, VA 23320
0.13
$278,000
2
2.5
1,642
Recently Sold
500 Judah Way #124, Chesapeake, VA 23320
0.14
$277,500
2
2.5
1,563
Recently Sold

Local Information

  • Map ViewExplore the area around 534 Windward Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Multi-Family
Year Built
1996
Living Area
2,026 sqft
Price/Sqft
$214
Parking
Garage

About this House

Great rent price for this 2026 sq ft single family home centrally located in the Greenbrier area of Chesapeake, VA close to the City Park, shopping, entertainment, and highways. Quiet neighborhood with one way in and out. Home features four bedrooms, two and a half baths, laminate flooring downstairs, wood burning fireplace, and three living areas: living, dining and family rooms, and a two car garage.
534 Windward Dr, Chesapeake, VA 23320 is a 4 bedroom, 3 bathroom, 2,026 sqft multi-family in Greenbrier East, built in 1996. It last sold for $298,000 on Nov 6, 2020. More recently, it was listed as a rental in October 2018 with an asking price of $1,750 per month. That rental listing was removed on October 24, 2018. It is currently off market. The Trulia Estimate is $433,900, with a rent estimate of $2,269/month.

Home Details for 534 Windward Dr

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Carpet, Laminate
Interior Details
Number of Rooms: 8Types of Rooms: Walk In Closet
Appliances & Utilities
DishwasherDisposalDryerRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: CompositionExterior: OtherFoundation Type: Slab
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1996
Property Type / Style
Property Type: Multi FamilyArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 5009 sqft

Price and Tax history

DateEventPrice
Nov 6, 2020
Source: N/A
Sold
$298,000
Oct 24, 2018
Source: Agent Provided
ListingRemoved
$1,750
Oct 2, 2018
Source: Agent Provided
Listed For Rent
$1,750
Apr 10, 2006
Source: N/A
Sold
$303,300

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 534 Windward Dr

  • What is 534 Windward Dr estimated to be worth?
    Trulia's estimated value for 534 Windward Dr in Chesapeake, VA is $433,900.
  • What is the price history for 534 Windward Dr?
    534 Windward Dr in Chesapeake, VA last sold for $298,000 in November 2020.
  • 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 534 Windward Dr have air conditioning?
    Yes, 534 Windward Dr in Chesapeake, VA has air conditioning.
  • Does 534 Windward Dr have laundry facilities?
    Yes, 534 Windward Dr in Chesapeake, VA has in-unit laundry.

Explore by feature - Pet Friendly

90 pet-friendly rentals in Chesapeake, VA

Explore by feature - Garage

64 rentals with a garage in Chesapeake, VA

Explore by feature - Air Conditioning

122 rentals with air conditioning in Chesapeake, VA

Explore by feature - Pool

57 rentals with a pool in Chesapeake, VA

Explore by feature - Washer/dryer

131 rentals with a washer/dryer in Chesapeake, VA

Explore by feature - Outdoor Space

47 rentals with an outdoor space in Chesapeake, VA

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Off Market Homes Near 534 Windward Dr

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