1 days on market
$290,000
526 Windward Dr
Chesapeake, Virginia 23320
MLS# 10636106 · ESTATES OF GREENBRIER · Chesapeake VA
Updated 14 hours ago · Source: REIN MLS
Est. payment
$1,891/mo
Edit below
Price / sq ft
$197
1,471 sq ft
Days on market
1
New listing
HOA
None
Year built
1996
30 yrs old
Beds
3
Full Baths
2
Half Baths
1
Sq Ft
1,471
Garage
Yes
Schools
- ElementaryGreenbrier Primary School—
- MiddleGreenbrier Middle School6/10
- 3/10
Info provided by GreatSchools
About this home
Short sale — offer accepted and currently pending lender approval.
Listed by Jonathan Mironchik · LPT Realty LLC
VaHome Team property overview
526 Windward Drive is a 3-bedroom, 2.1-bath home in Chesapeake, Virginia, built in 1996 with 1,471 square feet. It sits steps from Chesapeake City Park, a dog park, and a walkable cluster of dining and everyday conveniences — all within a minute of the USCG Finance Center.
Read full property overview ↓Show less ↑
Why this home stands out
What sets 526 Windward Drive apart is the rare combination of urban walkability and genuine green space in a city not always known for either. Fun Forest Playground is two-tenths of a mile away, Chesapeake City Park and its dog park are a three-minute walk, and a full lineup of restaurants and a grocery store are all within half a mile. For a sub-1,500-square-foot home, the lifestyle footprint here is surprisingly large.
ESTATES OF GREENBRIER and the Chesapeake real estate market
Chesapeake is Virginia's second-largest city by land area, and the area around Windward Drive sits near the heart of the Great Bridge corridor — one of the city's most established and connected pockets. The streets here have a settled, mature feel: tree-lined, quiet on weekday mornings, and genuinely walkable by Chesapeake standards. Residents are close to the city's administrative core, which means good infrastructure, well-maintained parks, and easy access to major routes heading toward Norfolk or Virginia Beach. If you've been working with chesapeake real estate agents and wondering where everyday convenience meets neighborhood calm, this corridor tends to come up early in that conversation. Chesapeake offers no city property tax on vehicles, a lower cost of living than its coastal neighbors, and a lifestyle that trades beach-town hustle for something a little more grounded — without sacrificing access to everything Hampton Roads has to offer.
What's nearby
Daily errands are genuinely easy from Windward Drive. Walmart Neighborhood Market is 0.4 miles away for quick grocery runs, and Old World Provisions — a Dietz & Watson specialty market — is just a mile out for something more curated. When it's time to eat, Zeke's, Ang's Sushi Bistro, and Atlas Pizza are all within 0.3 miles. Morning coffee is covered by Zeke's, a 7-Eleven, and a Wawa, all within half a mile. Fitness options are equally close: Chesapeake Hot Yoga, Fit Fusion, and TEALL Transformation Yoga are all under 0.6 miles. Fun Forest Playground, Chesapeake City Park, and the City Park Dog Park round out the picture — all within a short walk.
For different buyers
For military families relocating
The USCG Finance Center Chesapeake is literally one minute away — as close as a commute gets. Norfolk Naval Shipyard is about 13 minutes by car, making this address a practical fit for dual-military households or anyone weighing a VA loan purchase who needs flexibility between two installations. The low-traffic location and walkable park access make the day-to-day feel manageable even on long-duty weeks.
For families upgrading
Three bedrooms, two and a half baths, and a location where the kids can walk to Fun Forest Playground or Chesapeake City Park without loading into the car — that's a meaningful quality-of-life upgrade. The 1996 build means the bones are solid without the maintenance surprises of older stock, and the surrounding neighborhood has the kind of settled, established character that tends to hold its appeal over time.
Frequently asked questions
How far is 526 Windward Drive from the USCG Finance Center Chesapeake?
The USCG Finance Center is approximately one minute from 526 Windward Drive — it's essentially a neighbor. This makes Windward Drive one of the closest residential streets to that installation in the city.
How far is 526 Windward Drive from Norfolk Naval Shipyard?
Norfolk Naval Shipyard is roughly 13 minutes by car from 526 Windward Drive, making it a realistic daily commute for shipyard personnel who want to live in Chesapeake.
Is 526 Windward Drive in a flood zone?
Flood zone information for this address is displayed in the FloodRisk tile on this page — check there for the current FEMA designation and any associated details.
What parks are near 526 Windward Drive?
Fun Forest Playground is just 0.2 miles away, and both Chesapeake City Park and the City Park Dog Park are about 0.3 miles from the front door — all walkable without a car.
Does the neighborhood near 526 Windward Drive have an HOA?
HOA status for this specific property is noted in the listing details above — if an HOA applies, it will be indicated there along with any relevant rules or community information.
Want to know more about 526 Windward Drive or explore similar homes in Chesapeake? Tom and Dariya Milan at LPT Realty are here to help — reach out and let's talk.
Summary generated by AI from public records and publicly available information.
Location & Neighborhood
Location & Street View
526 Windward DR, Chesapeake
Map and Street View imagery © Google. Imagery may not be current.
Map data ©Google. Click and drag inside the map to explore the surrounding area.
Flood Risk
Property Details
Bedrooms
3
Full Baths
2
Half Baths
1
Approx Sq Ft
1,471
Stories
2
Fireplaces
0
Flooring
Carpet, Ceramic, Laminate/LVP
Heating
Cooling
Laundry
Interior Features
N/A
Appliances
Dishwasher, Disposal, Dryer, Dryer Hookup, Elec Range, Refrigerator, Washer, Washer Hookup
Sale & Tax History
List Price
$290,000
Price / Sq Ft
$197
Annual Taxes
$3,621
Monthly Tax
$302
HOA
None
Tax Rate (effective)
1.25%
Sale Timeline (this listing)
| Event | Date | Price | Detail |
|---|---|---|---|
| Listed | May 21, 2026 | $290,000 | — |
| Currently listed | — | $290,000 | — |
Looking for multi-year tax assessments or prior sales? REIN MLS only ships data for the current listing. For full property history, check the city assessor record:
Tax data above from REIN public-records sync. Sale timeline tracked from this listing's first appearance in our feed forward; prior owner sales are not included.
Comparable Properties
Comps are selected by city, bed count, square footage and price proximity. Composite similarity score weights bed match, sqft variance, price variance, and straight-line distance.
About buying in Chesapeake
Homes for sale in Chesapeake, VA appeal to buyers who want suburban space, top-rated schools, and easy access to Virginia Beach and Norfolk. The city's geography splits roughly into five corridors: Greenbrier (23320) with newer construction and shopping near the mall; Great Bridge (23320, 23322) with the historic Battlefield district and excellent schools; Hickory (23322) with large-lot family homes and Hickory High; Western Branch (23321) near the Portsmouth border with mature trees and starter homes; and Deep Creek / South Norfolk (23323, 23324) with affordable inventory and waterfront access. Buyer demand is anchored by Chesapeake Public Schools — among the highest-rated in Hampton Roads — including Hickory High, Grassfield High, Great Bridge High, and Western Branch High. Median home prices range from $300K starter homes in Deep Creek to $600K+ Great Bridge family homes and $1M+ luxury estates in Hickory's gated communities. Chesapeake's commute is excellent for buyers working in Virginia Beach, Norfolk Naval Shipyard, or Newport News Shipbuilding via the I-664 and I-64 corridors. Below you'll find every active Chesapeake MLS listing pulled hourly from the REIN feed.
Military Commute
Drive times to nearest basesDrive times via Google Maps with current traffic patterns. Times are typical and may vary by time of day. Use the "Analyze" button up top to see live drive time to your saved base.
Estimate your monthly payment
$1,891/moPrincipal & interest
$1,505
Property tax
$302
Home insurance
$85
PMI
None
HOA
None
Estimate only. Insurance assumed at 0.35% of home value annually. Actual taxes, insurance, and rate will vary by lender, credit, and property. Contact a lender for a personalized quote.
Listed by LPT Realty LLC · MLS# 10636106
Data provided by REIN MLS. Information deemed reliable but not guaranteed.
$290,000
526 Windward DR, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
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