505 Windward Dr, Chesapeake, VA 23320
OFF MARKET

$489,100

Trulia Estimate
as of Aug 26, 2026
  • 4 Beds
  • 2.5 Baths
  • 2,630 sqft
  • 4 Beds
  • 2.5 Baths
  • 2,630 sqft

505 Windward Dr, Chesapeake, VA 23320

Greenbrier East

Home Highlights

Property Type
Single-Family Home
Living Area
2,630 sqft
Price/Sqft
$186

Local Information

  • Map ViewExplore the area around 505 Windward Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

This lovely, well-maintained home is in the heart of the Greenbrier, close to the Chesapeake city park. The shopping plaza and highway are conveniently located nearby. The featured home has a fenced-in backyard with a stone patio. Four bedrooms and 2.5 bathrooms. A contemporary home with lots of natural light, the family room, with a gas fireplace and built-in shelving, opens to the kitchen and dining room. The Master bedroom suite retreats with a walk-in closet, double sink vanity, and soaking tub.

Leasing Requirements:
- 3X Monthly Rent in verifiable income (paystubs, bank statements, or tax documents)
- Minimum credit score of 620
- No evictions of past-due housing balances
A security deposit is required at the signing of the lease.

Showings will be available only to renters who have applied on Zillow and are qualified.

Renter responsible for utilities. No smoke allowed. Small pets (up to 20lb) permitted with $250 (Non-refundable) per pet , large pets may need approval.
505 Windward Dr, Chesapeake, VA 23320 is a 4 bedroom, 3 bathroom, 2,630 sqft single-family home in Greenbrier East. It last sold for $290,000 on Oct 16, 2018 (10,075% above the $2,850 asking price). More recently, it was listed as a rental in August 2024 with an asking price of $2,850 per month. That rental listing was removed on September 11, 2024. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $489,100, with a rent estimate of $3,048/month.

Home Details for 505 Windward Dr

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Interior Features

Appliances & Utilities
Dishwasher
Heating & Cooling
Air ConditioningCooling System: Central Air
Levels, Entrance, & Accessibility
Floors: Hardwood

Exterior Features

Parking & Garage
Parking: Off Street Parking, On Site

Comparable Sales for 505 Windward Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
519 Windward Dr, Chesapeake, VA
0.04
Single-Family Home
$425,000
06/25/26
4
4
2,800 sqft
717 Gulfwind Rd, Chesapeake, VA
0.18
Single-Family Home
$452,500
12/12/25
4
2.5
2,162 sqft
1028 Austin Dr, Chesapeake, VA
0.18
Single-Family Home
$497,000
08/14/26
4
2.5
2,339 sqft
900 Lee Shore Ct, Chesapeake, VA
0.15
Single-Family Home
$538,097
04/14/26
4
2.5
2,226 sqft
520 Windward Dr, Chesapeake, VA
0.07
Single-Family Home
$405,000
05/18/26
3
2
1,665 sqft
533 Tennis Dr, Chesapeake, VA
0.29
Single-Family Home
$330,000
02/09/26
4
2
1,979 sqft
903 Lee Shore Ct, Chesapeake, VA
0.14
Single-Family Home
$509,000
12/16/25
3
2.5
2,184 sqft
709 Gulfwind Rd, Chesapeake, VA
0.18
Single-Family Home
$470,000
09/12/25
3
2.5
2,108 sqft
910 Brandon Quay, Chesapeake, VA
0.42
Single-Family Home
$412,000
09/03/25
4
3
2,256 sqft
1005 Fairway Dr, Chesapeake, VA
0.22
Single-Family Home
$565,000
09/12/25
5
2.5
3,000 sqft

Nearby homes

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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

Price and Tax history

DateEventPrice
Sep 11, 2024
Source: Zillow Rentals
ListingRemoved
$2,850
Aug 15, 2024
Source: Zillow Rentals
Listed For Rent
$2,850
Aug 3, 2023
Source: Zillow Rentals
ListingRemoved
Jul 3, 2023
Source: Zillow Rentals
Listed For Rent
$2,800
Oct 16, 2018
Source: N/A
Sold
$290,000

Frequently asked questions about 505 Windward Dr

  • What is 505 Windward Dr estimated to be worth?
    Trulia's estimated value for 505 Windward Dr in Chesapeake, VA is $489,100.
  • What is the price history for 505 Windward Dr?
    505 Windward Dr in Chesapeake, VA last sold for $290,000 in October 2018.
  • 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 505 Windward Dr have air conditioning?
    Yes, 505 Windward Dr in Chesapeake, VA has air conditioning.
  • Does 505 Windward Dr have parking?
    Yes, 505 Windward Dr in Chesapeake, VA has on-site parking.

Homes for rent near 505 Windward Dr

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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