Is Greenbrier East, Chesapeake, VA dog-friendly?

As of early 2026, 94% of users say it's dog friendly

Is a car needed in Greenbrier East, Chesapeake, VA?

As of early 2026, 88% of users say car is needed

Is parking easy in Greenbrier East, Chesapeake, VA?

As of early 2026, 88% of users say parking is easy

Does Greenbrier East, Chesapeake, VA have sidewalks?

As of early 2026, 78% of users say there are sidewalks

Is Greenbrier East, Chesapeake, VA quiet?

As of early 2026, 74% of users say it's quiet

Are the streets well-lit in Greenbrier East, Chesapeake, VA?

As of early 2026, 73% of users say streets are well-lit

Does Greenbrier East, Chesapeake, VA show holiday spirit?

As of early 2026, 73% of users say there's holiday spirit

Would people walk alone at night in Greenbrier East, Chesapeake, VA?

As of early 2026, 72% of users say people would walk alone at night

Are yards well-kept in Greenbrier East, Chesapeake, VA?

As of early 2026, 70% of users say yards are well-kept

Do kids play outside in Greenbrier East, Chesapeake, VA?

As of early 2026, 68% of users say kids play outside

Do residents of Greenbrier East, Chesapeake, VA plan to stay at least 5 years?

As of early 2026, 56% of users say they plan to stay for at least 5 years

Is Greenbrier East, Chesapeake, VA walkable to restaurants?

As of early 2026, 53% of users say it's walkable to restaurants

Are neighbors friendly in Greenbrier East, Chesapeake, VA?

As of early 2026, 52% of users say neighbors are friendly

Is Greenbrier East, Chesapeake, VA walkable to grocery stores?

As of early 2026, 49% of users say it's walkable to grocery stores

Is there wildlife in Greenbrier East, Chesapeake, VA?

As of early 2026, 40% of users say there's wildlife

Are there community events in Greenbrier East, Chesapeake, VA?

As of early 2026, 28% of users say there are community events

FOR SALE

3D VIEW

527 Windward Dr
Chesapeake, VA 23320

Greenbrier East

4 Beds
2.5 Baths
2,100 sqft

$504,500

Est. Mortgage $2,929/mo*

Get Pre-Qualified

$504,500

Est. Mortgage $2,929/mo*

Get Pre-Qualified

4 Beds

2.5 Baths

2,100 sqft

Local Information

Map ViewExplore the area around 527 Windward Dr.
Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- 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 as a bonus complete with an additional fireplace! Outside folks will love the proximity to the Chesapeake City Park!Romantic gas fireplace in primary suite and more!

Home Highlights

Parking

1 Car Garage

Outdoor

Porch

A/C

Heating & Cooling

HOA

$23/Monthly

Price/Sqft

$240

Listed

10 days ago

Home Details for 527 Windward Dr

Interior Features
Interior Details Number of Rooms: 8Types of Rooms: Primary Bedroom, Bedroom, Full Bathroom, Dining Room, Family Room, Great Room, Kitchen, Living Room, Utility Room
Beds & Baths Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout Living Area: 2100 Square Feet
Appliances & Utilities Utilities: Cable HookupAppliances: 220 V Elec, Dishwasher, Disposal, Electric Range, Electric Water HeaterDishwasherDisposalLaundry: Dryer Hookup,Washer Hookup
Heating & Cooling Heating: Forced Air,Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa Number of Fireplaces: 2Fireplace: Fireplace Gas-naturalHas a Fireplace
Windows, Doors, Floors & Walls Window: Skylight(s)Flooring: Carpet, Ceramic Tile, Laminate/LVP
Levels, Entrance, & Accessibility Stories: 2Floors: Carpet, Ceramic Tile, Laminate LVP
View No View
Security Security: Security System

Exterior Features
Exterior Home Features Roof: CompositionPatio / Porch: PorchFencing: Back Yard, Rail, FencedExterior: Irrigation ControlFoundation: Slab
Parking & Garage Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 1Parking: Garage Att 1 Car,Multi Car,Off Street,On Street,Garage Door Opener
Pool Pool: None
Frontage Waterfront: Not WaterfrontNot on Waterfront
Water & Sewer Sewer: City/County
Farm & Range Not Allowed to Raise Horses

Days on Market
Days on Market: 10

Property Information
Year Built Year Built: 1997
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Traditional
Building Construction Materials: Brick, Vinyl SidingNot a New ConstructionNot Attached Property

Price & Status
Price List Price: $504,500Price Per Sqft: $240
Status Change & Dates Possession Timing: Negotiable

Active Status
MLS Status: Active

Location
Direction & Address City: ChesapeakeCommunity: Estates Of Greenbrier
School Information Elementary School: Greenbrier PrimaryJr High / Middle School: Greenbrier MiddleHigh School: Indian River

Agent Information
Listing Agent Listing ID: 10641660

HOA
Has an HOAHOA Fee: $23/Monthly

Listing Info
Special Conditions: VA Sale

Offer
Contingencies: Non Contingent

Miscellaneous
Mls Number: 10641660Attic: Pull Down Stairs

Additional Information
HOA Amenities: Landscaping

Last check for updates: about 3 hours ago

Listing courtesy of Janice Hollowell

World Class Realty, (757) 228-7773

Source: REIN Inc., MLS#10641660

Market trends in Greenbrier East

Last updated May 2026

Avg. sale price

$390K

$4.67KMoM

Sale-to-List Price

100.0%

Price per sq ft

$216

$4MoM

Available listings

102

3MoM

Similar Homes You May Like

Skip to last item

$460,000
4 bd
2.5 ba
2,233 sqft
1728 Parkview Ave,
Norfolk, VA 23503
$340,000
3 bd
2 ba
1,793 sqft
904 Culpepper St,
Norfolk, VA 23523
$353,800
3 bd
2.5 ba
1,707 sqft
1317 Eagles Trace Path #E,
Chesapeake, VA 23320
$524,900
4 bd
2.5 ba
2,301 sqft
2217 Arrowstone Ct,
Virginia Beach, VA 23456
$319,900
3 bd
2.5 ba
1,386 sqft
4619 Marlwood Way,
Virginia Beach, VA 23462
0.32 ACRES
$520,000
3 bd
2.5 ba
2,609 sqft
533 Broad Bend Cir,
Chesapeake, VA 23320
$355,000
3 bd
2.5 ba
1,633 sqft
3004 Big Bend Dr,
Chesapeake, VA 23321
$509,900
4 bd
2.5 ba
2,600 sqft
1515 Olde Mill Creek Dr,
Suffolk, VA 23434
0.29 ACRES
$640,000
5 bd
2.5 ba
2,628 sqft
3900 Orchard Spring Way,
Virginia Beach, VA 23456
$335,000
2 bd
2.5 ba
1,712 sqft
5236 Pirata Pl,
Virginia Beach, VA 23462
OPEN SAT, 11:30-2PM
$545,000
4 bd
2.5 ba
2,412 sqft
936 Saddleback Trail Rd,
Chesapeake, VA 23322
0.28 ACRES
$500,000
4 bd
2.5 ba
2,329 sqft
3614 Elkton Dr,
Chesapeake, VA 23321
$430,000
4 bd
3 ba
1,904 sqft
1904 Keeter Run,
Chesapeake, VA 23320
$390,000
3 bd
2.5 ba
1,700 sqft
3505 Farrier Cv,
Suffolk, VA 23435
$499,000
4 bd
2.5 ba
2,339 sqft
1028 Austin Dr,
Chesapeake, VA 23320
$674,900
4 bd
2.5 ba
2,475 sqft
2105 Buckboard Ct,
Virginia Beach, VA 23456
0.36 ACRES
$599,990
4 bd
2.5 ba
2,652 sqft
805 Dolph Cir,
Chesapeake, VA 23322
0.42 ACRES
$484,900
4 bd
2.5 ba
2,295 sqft
517 Three Oaks Dr,
Chesapeake, VA 23320
$344,777
3 bd
2.5 ba
2,307 sqft
3123 Sterling Way #12,
Portsmouth, VA 23703
$290,000
3 bd
2 ba
1,629 sqft
1623 Orchard Grove Dr,
Chesapeake, VA 23320
$377,900
3 bd
3.5 ba
1,764 sqft
5529 Taylors Walke Ln,
Virginia Beach, VA 23462
$489,000
3 bd
2.5 ba
1,950 sqft
1050 Collection Creek Way,
Virginia Beach, VA 23454
$400,000
3 bd
2 ba
1,438 sqft
1093 Elloree Ct,
Virginia Beach, VA 23464
$629,000
5 bd
3 ba
3,000 sqft
712 Creekwood Dr,
Chesapeake, VA 23323
$449,900
4 bd
2 ba
1,602 sqft
540 Aylesbury Dr,
Chesapeake, VA 23322
$493,000
4 bd
2.5 ba
2,509 sqft
1124 Kilby Dr,
Chesapeake, VA 23320
OPEN SUN, 2-4PM
$374,999
3 bd
2 ba
1,500 sqft
5440 Chatham Hall Dr,
Virginia Beach, VA 23464
0.27 ACRES
$559,900
5 bd
2.5 ba
2,700 sqft
3236 Bentham Ln,
Chesapeake, VA 23321
$320,000
3 bd
2.5 ba
1,632 sqft
1038 Bryce Ln,
Virginia Beach, VA 23464
$497,500
3 bd
2.5 ba
1,986 sqft
1277 Raynor Dr,
Virginia Beach, VA 23456
$425,000
3 bd
2.5 ba
1,900 sqft
3221 Twinflower Ln,
Virginia Beach, VA 23453
$590,000
3 bd
2.5 ba
2,250 sqft
5804 Woodstock Point,
Virginia Beach, VA 23464
0.25 ACRES
$400,000
3 bd
2.5 ba
1,888 sqft
301 Dixie Dr,
Norfolk, VA 23505
$594,500
5 bd
2.5 ba
2,500 sqft
2677 Alamance Cir,
Virginia Beach, VA 23456
$410,000
3 bd
2.5 ba
2,013 sqft
504 Crystal Bay Cir,
Suffolk, VA 23435
$350,000
2 bd
2 ba
1,502 sqft
904 Charnell Dr #303,
Virginia Beach, VA 23451
$435,000
4 bd
2.5 ba
2,230 sqft
3816 Davis St,
Norfolk, VA 23513
0.45 ACRES
$650,000
4 bd
2.5 ba
3,041 sqft
706 Tannahill Ct,
Chesapeake, VA 23322
$449,900
5 bd
3 ba
2,200 sqft
2040 Miller Ave,
Chesapeake, VA 23320
$585,000
5 bd
2.5 ba
2,850 sqft
4424 Revere Dr,
Virginia Beach, VA 23456
See more homes for sale in
Chesapeake
Take a look

Skip to first item

New Listings near 527 Windward Dr

Skip to last item

COMING SOON
$369,500
3 bd
2.5 ba
1,423 sqft
732 Fallcreek Run,
Chesapeake, VA 23322
$400,000
3 bd
2.5 ba
1,722 sqft
1001 Scarlet Oak Ct S,
Chesapeake, VA 23320
$275,000
4 bd
2.5 ba
1,860 sqft
224 Dexter St E,
Chesapeake, VA 23324
0.27 ACRES
$400,000
4 bd
2 ba
2,370 sqft
205 Fillmore Pl,
Chesapeake, VA 23325
1 ACRE
$419,900
4 bd
2 ba
1,794 sqft
1400 Fentress Rd,
Chesapeake, VA 23322
NEW - 14 HRS AGO
$300,000
4 bd
3 ba
1,460 sqft
1236 Damyien Arch,
Chesapeake, VA 23320
COMING SOON
0.28 ACRES
$425,000
4 bd
2 ba
2,148 sqft
500 N Hills Dr,
Chesapeake, VA 23320
0.46 ACRES
$394,000
3 bd
2 ba
1,288 sqft
216 Marion Dr,
Chesapeake, VA 23322
$750,000
4 bd
2.5 ba
2,649 sqft
609 Shasta Dr,
Chesapeake, VA 23320
$399,900
3 bd
2.5 ba
1,946 sqft
5329 Doon St,
Virginia Beach, VA 23464
0.31 ACRES
$425,000
4 bd
2.5 ba
2,488 sqft
371 Knells Ridge Dr,
Chesapeake, VA 23320
$295,900
2 bd
2.5 ba
1,500 sqft
813 Shenandoah River Rd,
Chesapeake, VA 23320
$487,500
4 bd
2.5 ba
2,400 sqft
1545 Drumheller Dr,
Virginia Beach, VA 23464
NEW - 1 DAY AGO
0.28 ACRES
$550,000
4 bd
2 ba
2,064 sqft
529 Royal Grant Dr,
Chesapeake, VA 23322
0.4 ACRES
$590,000
4 bd
2.5 ba
2,600 sqft
1045 Winchester Way,
Chesapeake, VA 23320
See more homes for sale in
Chesapeake
Take a look

Skip to first item

Property Tax and Assessment

Year	2025
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
900 Lee Shore Ct, Chesapeake, VA	0.10	Single-Family Home	$538,097	04/14/26	4	2.5	2,226
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
824 Cranston Dr, Chesapeake, VA	0.25	Single-Family Home	$450,000	01/02/26	4	2	1,711
828 Cranston Dr, Chesapeake, VA	0.26	Single-Family Home	$485,000	05/22/26	4	3	1,664
114 Greenbrier Rd, Chesapeake, VA	0.28	Single-Family Home	$400,000	12/18/25	4	2	1,736

Nearby homes

Get a sense of prices in the area by checking nearby homes.

Skip to last item

FOR SALE
$505,000
3 bd
2.5 ba
2,383 sqft
800 Broad Reach Rd,
Chesapeake, VA 23320
FOR SALE
$290,000
3 bd
2.5 ba
1,471 sqft
526 Windward Dr,
Chesapeake, VA 23320
SOLD
DEC 16, 2025
$509,000
3 bd
2.5 ba
2,184 sqft
903 Lee Shore Ct,
Chesapeake, VA 23320
SOLD
APR 14, 2026
$538,097
4 bd
2.5 ba
2,226 sqft
900 Lee Shore Ct,
Chesapeake, VA 23320
SOLD
DEC 12, 2025
$452,500
4 bd
2.5 ba
2,162 sqft
717 Gulfwind Rd,
Chesapeake, VA 23320
SOLD
SEP 12, 2025
$470,000
3 bd
2.5 ba
2,108 sqft
709 Gulfwind Rd,
Chesapeake, VA 23320
SOLD
MAY 8, 2026
$277,500
2 bd
2.5 ba
1,563 sqft
500 Judah Way #124,
Chesapeake, VA 23320
FOR SALE
$264,900
2 bd
2 ba
1,215 sqft
500 Judah Way #123,
Chesapeake, VA 23320
SOLD
JUN 12, 2026
$278,000
2 bd
2.5 ba
1,642 sqft
140 Springer Ln #232,
Chesapeake, VA 23320
FOR SALE
$499,000
4 bd
2.5 ba
2,339 sqft
1028 Austin Dr,
Chesapeake, VA 23320
SOLD
JAN 29, 2026
$315,000
2 bd
2.5 ba
1,870 sqft
612 Lacy Oak Dr,
Chesapeake, VA 23320

Skip to first item

Additional Cost

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

160 Homes For You
Buy: $210k - $1.25m

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
Resident
3mo ago
"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
Visitor
10mo ago
" 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
Resident
11mo ago
"Excellent book club! Neighbors are very friendly. Quiet neighbors,nice pool. Walkable to grocery, restaurants and library. "
0
Flag
M2jfr2k9vs
Resident
1y ago
"Motor vehicles are the ultimate way to travel, they’re so convenient! I highly recommend getting or having a vehicle!!!"
1
Flag
94zw848pdw
Resident
1y ago
"Not too bad. I get to work within 20 minutes with minimal traffic. Not sure what else to say about it"
2
Flag
Kclynncarlisle
Resident
1y ago
"Pizza party’s, barbecues, trick or treating, thanksgiving potlucks, back porch hang outs, pool party’s. "
0
Flag
Colpotitoli
Resident
2y ago
"Nice safe clean friendly close to all shopping center urgent care and other hospitals are very close "
1
Flag
Trulia User
Resident
3y ago
"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
Resident
3y ago
"Great community, Friendly , quiet , kid friendly. Lived here all of my life and have never had issues or problems. "
0
Flag
Trulia User
Prev. Resident
3y ago
"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
Resident
4y ago
"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
Visitor
5y ago
"They would definitely not like people not picking up after their dogs They’ll love walking their dog around the neighborhood "
0
Flag
Rachelrb
Resident
5y ago
"This neighborhood is the perfect place to raise a family.It’s beautiful, safe, and extremely fun for kids! "
13
Flag
Ken L.
Resident
5y ago
"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.
Resident
6y ago
"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
Resident
6y ago
"Great area to raise kids, family oriented area. Great parks and trails. Lots to do and close proximity to everything necessary "
1
Flag
Stephaniestout94
Resident
6y ago
"Quiet neighborhood. A lot of families. Close to everything. Food entertainment , shopping, dog parks. "
2
Flag
Katelyn W.
Resident
6y ago
"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.
Resident
6y ago
"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.
Resident
6y ago
"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.
Resident
6y ago
"It’s a great place to live, especially if you have a young family! Great schools, and great for pets! "
0
Flag
Ash M.
Resident
6y ago
"Great neighborhood with great restaurants and shopping within 5 miles radius. Very safe with sidewalks pretty much everywhere."
3
Flag
Ahagenbucher182
Resident
6y ago
"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
Resident
6y ago
"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.
Resident
6y ago
"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.
Visitor
6y ago
"Been around this neighborhood for a while. Very family friendly. Love the area in general. Great place to raise a family."
3
Flag
Fw
Resident
6y ago
"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
Resident
7y ago
"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
Resident
7y ago
"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
Resident
7y ago
"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
Resident
7y ago
"Cooks outs, sharing info, schools, friends, scenery, hospitality, clean, pool, fun, picnics, and parties "
0
Flag
Fabian O.
Resident
7y ago
"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.
Resident
7y ago
"Dog owners would love that 4 Paws, PetSmart, Barker and open dog parks are literally down the street"
0
Flag
Amy B.
Resident
7y ago
"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
Resident
7y ago
"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
Resident
7y ago
"Dogs in the Greenbrier area seem to be friendly and well-trained; I never hear loud, constant barking. "
0
Flag

LGBTQ Local Legal Protections

Janice Hollowell, World Class Realty, (757) 228-7773

The listings data displayed on this medium comes in part from the Real Estate Information Network, Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
Copyright 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW. REIN updates its listings on a daily basis. Data last updated: 2026-07-07 05:22:20 PDT.
Some listings may be duplicated in the search results due to the co-mingling of listings from more than one multiple listing service. Should there be different listing information between the duplicated listings; user is advised to verify the accuracy of the listing information before making any financial decisions.
This application does not include information on all of the properties available for sale at this time.

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 currently available for sale and was listed by REIN Inc. on Jun 26, 2026. The MLS # for this home is MLS# 10641660.

527 Windward Dr
Chesapeake, VA 23320

$504,500

$504,500

Local Information