527 Windward Dr, Chesapeake, VA 23320
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FOR SALE
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527 Windward Dr
Chesapeake, VA 23320

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

$498,000

Est. Mortgage $2,979/mo*
Get Pre-Qualified

$498,000

Est. Mortgage $2,979/mo*
Get Pre-Qualified
4 Beds
2.5 Baths
2,100 sqft

Home Highlights

Parking
1 Car Garage
Outdoor
Porch
HOA
$23/Monthly
Price/Sqft
$237
Climate Control
Forced Air, Natural Gas & Central Air
Listed
56 days ago

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

About this House

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!
Last check for updates: about 5 hours ago
Listing courtesy of Janice Hollowell
World Class Realty, (757) 228-7773
Source: REIN Inc., MLS#10641660

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: 56

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: $498,000Price Per Sqft: $237
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

Offer

Contingencies: Non Contingent

Miscellaneous

Mls Number: 10641660Attic: Pull Down Stairs

Additional Information

HOA Amenities: Landscaping

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

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

Home Value

Trulia Estimate
$498K
Since last month
Decreased$7K (-1.4%)
Since last year
Increased$41K (+9%)
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 +69% in the last 10 years
MonthEstimated value
2026
August 2026$498K
July 2026$505K
June 2026$510K
May 2026$476K
April 2026$473K
March 2026$466K
February 2026$463K
January 2026$457K
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
0.10
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
519 Windward Dr, Chesapeake, VA
0.04
Single-Family Home
$425,000
06/25/26
4
3.5
2,595
1028 Austin Dr, Chesapeake, VA
0.17
Single-Family Home
$497,000
08/14/26
4
2.5
2,339
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 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
800 Broad Reach Rd, Chesapeake, VA 23320
0.04
$475,000
3
2.5
2,383
For Sale
519 Windward Dr, Chesapeake, VA 23320
0.04
$425,000
4
3.5
2,595
Recently Sold
526 Windward Dr, Chesapeake, VA 23320
0.03
$290,000
3
2.5
1,471
For Sale
903 Lee Shore Ct, Chesapeake, VA 23320
0.08
$509,000
3
2.5
2,184
Recently Sold
602 Windward Dr, Chesapeake, VA 23320
0.07
$489,900
4
2.5
2,100
For Sale
900 Lee Shore Ct, Chesapeake, VA 23320
0.10
$538,097
4
2.5
2,226
Recently Sold
717 Gulfwind Rd, Chesapeake, VA 23320
0.10
$452,500
4
2.5
2,162
Recently Sold
709 Gulfwind Rd, Chesapeake, VA 23320
0.11
$487,100
3
2.5
2,108
Off Market
500 Judah Way #124, Chesapeake, VA 23320
0.15
$277,500
2
2.5
1,563
Recently Sold
500 Judah Way #123, Chesapeake, VA 23320
0.16
$259,900
2
2
1,215
For Sale
140 Springer Ln #232, Chesapeake, VA 23320
0.16
$278,000
2
2.5
1,642
Recently Sold

Price and Tax history

YearProperty taxTax assessment
2025
$4,251
$420,900
Home facts updated by county records

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. © 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: 2026-08-21 12:37:44 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.
Some or all of the listings (or Listing Data) represented in this application have been enhanced with information not provided by REIN. Such enhancements may include information obtained from Zillow Inc. and other third-party or publicly available sources and are not part of the Listing Data provided by REIN.

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Frequently asked questions about 527 Windward Dr

  • What is the estimated monthly payment for 527 Windward Dr?
    Based on a $498,000 list price with 20% down at today's rates, the estimated monthly payment for 527 Windward Dr in Chesapeake, VA is approximately $3,010 (about $2,591 principal & interest, $344 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 527 Windward Dr compare to homes in Chesapeake?
    527 Windward Dr in Chesapeake, VA is listed at $498,000, about 23% above the $403K median sale price in Chesapeake.
  • What do residents say about the Greenbrier East neighborhood?
    Residents describe the Greenbrier East neighborhood in Chesapeake, VA as dog-friendly, easy to park in, and pedestrian-friendly. See homes for sale in Greenbrier East, Chesapeake.
  • What are the closest schools to 527 Windward Dr?
    The closest schools to 527 Windward Dr in Chesapeake, VA are Greenbrier Intermediate School (Elementary, rated 6/10), Greenbrier Middle School (rated 7/10), Greenbrier Primary School (Pre-K, rated 6/10).
  • Does 527 Windward Dr have air conditioning?
    Yes, 527 Windward Dr in Chesapeake, VA has air conditioning.
  • Does 527 Windward Dr have laundry facilities?
    Yes, 527 Windward Dr in Chesapeake, VA has laundry facilities.
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.