$290,000
3 Beds
2.5 Baths
1,471 sqft
526 Windward Dr, Chesapeake, VA 23320
Est. Mortgage $1,818/mo*
Get Pre-QualifiedWe estimate this home will sell faster than 99% nearby.
Home Highlights
Single-Family Home
Built in 1996
$197/sqft
2 Car Garage
HOA $23/mo
Local Information
- Map ViewExplore the area around 526 Windward Dr.
- Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
- Shop & Eat
-- mins to
About this House
Short sale — offer accepted and currently pending lender approval.
Last check for updates: about 7 hours ago
Listing courtesy of Jonathan Mironchik
LPT Realty LLC, (877) 366-2213
Source: REIN Inc., MLS#10653125
We estimate this home will sell faster than 99% nearby.
Home Details for 526 Windward Dr
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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 |
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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 |
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Days on Market: 63 |
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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 |
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Price List Price: $290,000Price Per Sqft: $197 |
Status Change & Dates Off Market Date: Thu Sep 10 2026Possession Timing: Settlement |
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MLS Status: Under Contract |
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Direction & Address City: ChesapeakeCommunity: Estates Of Greenbrier |
School Information Elementary School: Greenbrier PrimaryJr High / Middle School: Greenbrier MiddleHigh School: Indian River |
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Listing Agent Listing ID: 10653125 |
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Has an HOAHOA Fee: $23/Monthly |
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Special Conditions: Short/Comp Sale |
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Contingencies: Home/EIFS Insp. Con., Third Party Approval, Contingent |
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Mls Number: 10653125Zillow Contingency Status: Under ContractAttic: Pull Down Stairs |
Price and Tax history
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | $3,621 | $358,500 |
Home facts updated by county records
Around this home
Neighborhood Overview
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.
Market trends in Greenbrier East
Last updated October 2026
Avg. sale price
$388K
$16.5KMoM
Sale-to-List Price
100.0%
0.1%MoM
Price per sq ft
$219
$2MoM
Available listings
100
10MoM
Sourced by Trulia Market Trends
Home Value
Trulia Estimate
$293KSince last month
Decreased$3K (-1.1%)Since last year
Decreased$89K (-23.4%)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
| Month | Estimated value |
|---|---|
2026 | |
| November 2026 | $293K |
| October 2026 | $292K |
| September 2026 | $296K |
| August 2026 | $291K |
| 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 |
|---|---|---|---|---|---|---|---|
0.06 | Single-Family Home | $475,000 | 09/21/26 | 3 | 2.5 | 2,383 | |
0.09 | Single-Family Home | $509,000 | 12/16/25 | 3 | 2.5 | 2,184 | |
0.06 | Single-Family Home | $455,000 | 10/01/26 | 4 | 2.5 | 2,100 | |
0.10 | Single-Family Home | $452,500 | 12/12/25 | 4 | 2.5 | 2,162 | |
0.12 | Single-Family Home | $538,097 | 04/14/26 | 4 | 2.5 | 2,226 | |
0.23 | Single-Family Home | $485,000 | 05/22/26 | 4 | 3 | 1,664 | |
0.14 | Single-Family Home | $497,000 | 08/14/26 | 4 | 2.5 | 2,339 | |
0.22 | Single-Family Home | $450,000 | 01/02/26 | 4 | 2 | 1,711 | |
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 |
|---|---|---|---|---|---|---|
0.01 | $408,200 | 3 | 2 | 1,588 | Off Market | |
0.01 | $405,800 | 3 | 2 | 1,505 | Off Market | |
0.02 | $480,800 | 4 | 3 | 2,498 | Off Market | |
0.02 | - | 4 | 3 | 2,200 | Off Market | |
0.03 | $426,000 | 4 | 3 | 1,901 | Off Market | |
0.03 | $405,000 | 3 | 2 | 1,665 | Recently Sold | |
0.03 | $494,800 | 4 | 2.5 | 2,100 | Off Market | |
0.03 | $449,900 | 4 | 3 | 2,091 | Off Market | |
0.03 | $467,400 | 3 | 3 | 2,400 | Off Market | |
0.03 | $486,800 | 4 | 3 | 2,382 | Off Market | |
0.04 | $454,700 | 4 | 3 | 1,916 | Off Market | |
0.04 | $425,300 | 4 | 3 | 2,026 | Off Market | |
0.04 | $474,700 | 4 | 2.5 | 2,091 | Off Market | |
0.04 | $463,900 | 3 | 2.5 | 2,300 | Off Market | |
0.04 | $388,800 | 3 | 2 | 1,500 | Off Market | |
0.05 | $499,100 | 4 | 2.5 | 2,413 | Off Market | |
0.05 | $432,100 | 4 | 3 | 2,066 | Off Market | |
0.05 | $463,200 | 3 | 2.5 | 2,257 | Off Market | |
0.05 | $466,700 | 3 | 3 | 2,272 | Off Market | |
0.05 | $425,000 | 4 | 3.5 | 2,595 | Recently Sold |
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Jonathan Mironchik, LPT Realty LLC, (877) 366-2213
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: 2026-11-12 22:07:19 PST
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.
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 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 $1,874 (about $1,598 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 25% below the $388K 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.
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 Sep 10, 2026. The MLS # for this home is MLS# 10653125.