527 Windward Dr, Chesapeake, VA 23320
OFF MARKET

527 Windward Dr
Chesapeake, VA 23320

Greenbrier East
  • 4 Beds
  • 2.5 Baths
  • 2,100 sqft

$474,600

Trulia Estimate
as of May 23, 2026
Est. Refi. Payment $2,793/mo*
Refinance Your Home

$474,600

Trulia Estimate
as of May 23, 2026
Est. Refi. Payment $2,793/mo*
Refinance Your Home
4 Beds
2.5 Baths
2,100 sqft

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Come check out this amazing well kept two story home in the heart of Greenbrier. Conveniently located to shopping, restaurants, parks, military bases and major interstates. Roof was replaced in 2015, HVAC in 016, gutter and vinyl wrap in 2017, master shower replaced in 2022. Home features a huge master bedroom sitting area along with 2 gorgeous fireplaces. Avoid regret and future disappointment by submitting an offer today. Original owners.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 527 Windward Dr

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
AtticNumber of Rooms: 8
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other, BrickFoundation Type: Slab
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1997Year Updated: 2019
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 5009 sqft

Price History for 527 Windward Dr

DatePriceEventSource
10/31/2022$399,900Sold
N/A
10/24/2022$399,900PendingRE/MAX International #10457311
10/24/2022$399,900ContingentREIN Inc. #10457311
09/26/2022$399,900PriceChange
REIN Inc. #10457311
09/17/2022$429,900Listed For SaleREIN Inc. #10457311
10/15/2002$172,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$4,251
Assessment$420,900
Home facts updated by county records

Comparable Sales for 527 Windward Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
717 Gulfwind Rd, Chesapeake, VA
0.10
Single-Family Home
$452,500
12/12/25
4
2.5
2,162
903 Lee Shore Ct, Chesapeake, VA
0.08
Single-Family Home
$509,000
12/16/25
3
2.5
2,184
709 Gulfwind Rd, Chesapeake, VA
0.11
Single-Family Home
$470,000
09/12/25
3
2.5
2,108
910 Brandon Quay, Chesapeake, VA
0.47
Single-Family Home
$412,000
09/03/25
4
3
2,256
1024 Austin Dr, Chesapeake, VA
0.16
Single-Family Home
$300,000
07/24/25
4
3
2,254
460 Blue Beech Way, Chesapeake, VA
0.48
Single-Family Home
$415,500
07/14/25
3
3
2,352
901 Angel Ct, Chesapeake, VA
0.38
Single-Family Home
$505,000
07/18/25
4
2.5
2,243
426 Blue Beech Way, Chesapeake, VA
0.46
Single-Family Home
$435,000
09/02/25
3
2.5
2,352
928 Wynngate Dr, Chesapeake, VA
0.24
Single-Family Home
$415,000
09/23/25
3
2.5
1,600
1025 Woodsmans Reach, Chesapeake, VA
0.61
Single-Family Home
$430,000
06/16/25
4
2.5
2,162

Nearby homes

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Assigned Schools

These are the assigned schools for 527 Windward Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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 people would walk alone at night

  • 73 % Say streets are well-lit

  • 73 % Say there's holiday spirit

  • 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

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527 Windward Dr, Chesapeake, VA 23320 is a 4 bedroom, 3 bathroom, 2,100 sqft single-family home built in 1997. 527 Windward Dr is located in Greenbrier East, Chesapeake. This property is not currently available for sale. 527 Windward Dr was last sold on Oct 31, 2022 for $399,900. The current Trulia Estimate for 527 Windward Dr is $474,600.