526 Windward Dr, Chesapeake, VA 23320
Property image
Property image
FOR SALE

526 Windward Dr
Chesapeake, VA 23320

Greenbrier East
  • 3 Beds
  • 2.5 Baths
  • 1,471 sqft

$290,000

Est. Mortgage $1,776/mo*
Get Pre-Qualified

$290,000

Est. Mortgage $1,776/mo*
Get Pre-Qualified
3 Beds
2.5 Baths
1,471 sqft
We estimate this home will sell faster than 83% nearby.

Home Highlights

Parking
2 Car Garage
Outdoor
Patio, Deck
Climate Control
Heat Pump & Central Air
HOA
$23/Monthly
Price/Sqft
$197
Listed
89 days ago

Local Information

  • Map ViewExplore the area around 526 Windward Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Short sale — offer accepted and currently pending lender approval.
We estimate this home will sell faster than 83% nearby.

Home Details for 526 Windward Dr

Interior Features

Interior Details
Number of Rooms: 6Types of Rooms: Primary Bedroom, Bedroom, Full Bathroom, Dining Room, Family Room, Great Room, Kitchen, Living Room, Utility Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 1471 Square Feet
Appliances & Utilities
Utilities: Cable HookupAppliances: Dishwasher, Disposal, Dryer, Electric Range, Refrigerator, Washer, Gas Water HeaterDishwasherDisposalDryerLaundry: Dryer Hookup,Washer HookupRefrigeratorWasher
Heating & Cooling
Heating: Heat PumpHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Wood BurningHas a Fireplace
Windows, Doors, Floors & Walls
Flooring: Carpet, Ceramic Tile, Laminate/LVPCommon Walls: No Common Walls
Levels, Entrance, & Accessibility
Stories: 2Accessibility: LiftFloors: Carpet, Ceramic Tile, Laminate LVP
View
No View

Exterior Features

Exterior Home Features
Roof: Asphalt ShinglePatio / Porch: Deck, PatioFencing: Back Yard, Full, Wood, FencedFoundation: Slab
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Garage Att 2 Car,Driveway
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: 89

Property Information

Year Built
Year Built: 1996
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Contemp,Traditional
Building
Construction Materials: Vinyl SidingNot a New ConstructionNot Attached Property
Property Information
Condition: Fixer

Price & Status

Price
List Price: $290,000Price Per Sqft: $197
Status Change & Dates
Possession Timing: Settlement

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: 10636106

HOA

Has an HOAHOA Fee: $23/Monthly

Listing Info

Special Conditions: Short/Comp Sale

Offer

Contingencies: Third Party Approval, Contingent

Miscellaneous

Mls Number: 10636106Attic: Pull Down Stairs
Last check for updates: about 3 hours ago
Listing courtesy of Jonathan Mironchik
LPT Realty LLC, (877) 366-2213
Source: REIN Inc., MLS#10636106

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

Price and Tax history

YearProperty taxTax assessment
2025
$3,621
$358,500
Home facts updated by county records

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Home Value

Trulia Estimate
$297K
Since last month
Increased$5K (+1.7%)
Since last year
Decreased$86K (-22.4%)
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 +24% in the last 10 years
MonthEstimated value
2026
August 2026$297K
July 2026$292K
June 2026$295K
May 2026$300K
April 2026$392K
March 2026$386K
February 2026$382K
January 2026$382K
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
903 Lee Shore Ct, Chesapeake, VA
0.09
Single-Family Home
$509,000
12/16/25
3
2.5
2,184
709 Gulfwind Rd, Chesapeake, VA
0.12
Single-Family Home
$470,000
09/12/25
3
2.5
2,108
928 Wynngate Dr, Chesapeake, VA
0.22
Single-Family Home
$415,000
09/23/25
3
2.5
1,600
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
0.12
Single-Family Home
$538,097
04/14/26
4
2.5
2,226
828 Cranston Dr, Chesapeake, VA
0.23
Single-Family Home
$485,000
05/22/26
4
3
1,664
1028 Austin Dr, Chesapeake, VA
0.14
Single-Family Home
$497,000
08/14/26
4
2.5
2,339
824 Cranston Dr, Chesapeake, VA
0.22
Single-Family Home
$450,000
01/02/26
4
2
1,711
519 Windward Dr, Chesapeake, VA
0.05
Single-Family Home
$425,000
06/25/26
4
3.5
2,595

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
527 Windward Dr, Chesapeake, VA 23320
0.03
$498,000
4
2.5
2,100
For Sale
602 Windward Dr, Chesapeake, VA 23320
0.06
$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
0.05
$425,000
4
3.5
2,595
Recently Sold
903 Lee Shore Ct, Chesapeake, VA 23320
0.09
$509,000
3
2.5
2,184
Recently Sold
717 Gulfwind Rd, Chesapeake, VA 23320
0.10
$452,500
4
2.5
2,162
Recently Sold
900 Lee Shore Ct, Chesapeake, VA 23320
0.12
$538,097
4
2.5
2,226
Recently Sold
709 Gulfwind Rd, Chesapeake, VA 23320
0.12
$487,100
3
2.5
2,108
Off Market
1028 Austin Dr, Chesapeake, VA 23320
0.14
$497,000
4
2.5
2,339
Recently Sold
140 Springer Ln #232, Chesapeake, VA 23320
0.16
$278,000
2
2.5
1,642
Recently Sold
500 Judah Way #124, Chesapeake, VA 23320
0.16
$277,500
2
2.5
1,563
Recently Sold

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 526 Windward Dr

  • What is the estimated monthly payment for 526 Windward Dr?
    Based on a $290,000 list price with 20% down at today's rates, the estimated monthly payment for 526 Windward Dr in Chesapeake, VA is approximately $1,785 (about $1,509 principal & interest, $201 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 526 Windward Dr compare to homes in Chesapeake?
    526 Windward Dr in Chesapeake, VA is listed at $290,000, about 28% below 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 526 Windward Dr?
    The closest schools to 526 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 526 Windward Dr have air conditioning?
    Yes, 526 Windward Dr in Chesapeake, VA has air conditioning.
  • Does 526 Windward Dr have laundry facilities?
    Yes, 526 Windward Dr in Chesapeake, VA has in-unit laundry.
Jonathan Mironchik, LPT Realty LLC, (877) 366-2213
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526 Windward Dr, Chesapeake, VA 23320 is a 3 bedroom, 3 bathroom, 1,471 sqft single-family home built in 1996. 526 Windward Dr is located in Greenbrier East, Chesapeake. This property is currently available for sale and was listed by REIN Inc. on May 21, 2026. The MLS # for this home is MLS# 10636106.