5 days on market
$400,000
519 Windward Dr
Chesapeake, Virginia 23320
MLS# 10636623 · ESTATES OF GREENBRIER · Chesapeake VA
Updated Jun 1, 2026 · Source: REIN MLS
Est. payment
$2,578/mo
Edit below
Price / sq ft
$154
2,595 sq ft
Days on market
5
New listing
HOA
None
Year built
1997
29 yrs old
Beds
4
Full Baths
3
Half Baths
1
Sq Ft
2,595
Garage
Yes
Schools
- ElementaryGreenbrier Intermediate School6/10
- MiddleGreenbrier Middle School6/10
- 3/10
Info provided by GreatSchools
About this home
Priced to Sell in Chesapeake! Don't miss this opportunity to own a spacious 4-bedroom, 3.5-bath home offering approximately 2,596 square feet of living space. Features include a 2-car garage, an eat-in kitchen, and a gas fireplace. This home needs some TLC and updating, but offers tremendous potential for buyers looking to build equity and make it their own. Located in an established neighborhood near shopping, dinin…
Listed by Patricia Lobo · KW Coastal Virginia Chesapeake
VaHome Team property overview
519 Windward Drive is a four-bedroom, three-and-a-half-bath home in Chesapeake, Virginia, built in 1997 with 2,595 square feet of living space. It sits steps from Chesapeake City Park and within a minute of the USCG Finance Center — a genuinely rare combination of green space and commute convenience.
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Why this home stands out
What sets 519 Windward Drive apart is the pairing of an unusually large footprint — nearly 2,600 square feet with four bedrooms and three full baths plus a half — with a location that puts a major city park, a dog park, a playground, grocery options, and a cluster of local restaurants all within a half-mile. You get the square footage of a suburban retreat without sacrificing walkable daily convenience.
ESTATES OF GREENBRIER and the Chesapeake real estate market
Chesapeake is one of the largest cities by land area on the East Coast, and the neighborhood around Windward Drive captures some of the best of what it offers: mature tree canopy, easy access to city amenities, and a genuine sense of community without the density of an urban core. The area sits in the heart of Chesapeake's established residential fabric — close enough to the action that errands are quick, far enough from the highway that the streets stay quiet. If you've been working with real estate agents in chesapeake va, you've likely heard this corridor come up as a perennial favorite for families and professionals alike. Chesapeake itself offers a city government that prioritizes parks and public infrastructure, and the neighborhood around Windward Drive is a direct beneficiary of that investment — Chesapeake City Park is practically in the backyard.
What's nearby
Fun Forest Playground and Chesapeake City Park are both just 0.2 miles away, making this address genuinely walkable for families with young kids or anyone who values green space. City Park Dog Park is 0.3 miles out. Groceries are covered by Walmart Neighborhood Market at 0.4 miles and Old World Provisions (Dietz & Watson) at 0.9 miles. For dining, Zeke's, Ang's Sushi Bistro, and Atlas Pizza are all within 0.4 miles. Morning coffee is easy — Zeke's, a 7-Eleven, and a Wawa are all under half a mile. Fitness options include Chesapeake Hot Yoga and Fit Fusion within 0.5 miles, plus TEALL Transformation Yoga at 0.7 miles.
For different buyers
For military families relocating
The USCG Finance Center Chesapeake is literally one minute away — it doesn't get more commute-friendly than that. Norfolk Naval Shipyard is a 13-minute drive, making this address a strong fit for dual-military households or anyone assigned to either installation. A VA loan can make a home this size more accessible than you might expect, and the location means you're spending less time in the car and more time at home.
For families upgrading
Four bedrooms and three and a half baths across 2,595 square feet gives a growing family real room to spread out — and the location backs that up. Fun Forest Playground and Chesapeake City Park are a two-minute walk, the dog park is three minutes away, and a cluster of restaurants and grocery options sits within half a mile. This is city of chesapeake real estate at a scale that actually fits family life.
Frequently asked questions
How far is 519 Windward Drive from the USCG Finance Center Chesapeake?
The USCG Finance Center Chesapeake is approximately one minute from 519 Windward Drive — one of the closest residential addresses you'll find to that installation. For active-duty Coast Guard members, the commute essentially disappears.
How far is 519 Windward Drive from Norfolk Naval Shipyard?
Norfolk Naval Shipyard is about 13 minutes by car from 519 Windward Drive, making this a practical address for personnel assigned to the shipyard who want to live on the Chesapeake side of the water.
What parks are near 519 Windward Drive?
Chesapeake City Park and Fun Forest Playground are both 0.2 miles away, and City Park Dog Park is 0.3 miles out — all walkable from the front door.
Is 519 Windward Drive in a flood zone?
Flood zone information for 519 Windward Drive is displayed in the FloodRisk tile on this page, which pulls current FEMA map data for the parcel. Check that section for the most accurate and up-to-date designation.
What is the square footage and layout of 519 Windward Drive?
The home offers 2,595 square feet of living space with four bedrooms, three full bathrooms, and one half-bath, built in 1997 — a layout that works well for larger households or anyone who wants dedicated guest or office space.
Want to know more about 519 Windward Drive or the surrounding Chesapeake market? Tom and Dariya Milan at LPT Realty are ready to walk you through everything — reach out anytime.
Summary generated by AI from public records and publicly available information.
Location & Neighborhood
Places within ~1 mile, ordered by distance from this property. Powered by Google Places.
Flood Risk
Property Details
Bedrooms
4
Full Baths
3
Half Baths
1
Approx Sq Ft
2,595
Stories
2
Fireplaces
0
Flooring
Laminate/LVP, Vinyl
Heating
Cooling
Laundry
Interior Features
N/A
Appliances
Dishwasher, Dryer Hookup, Microwave, Gas Range, Refrigerator, Washer Hookup
Sale & Tax History
List Price
$400,000
Price / Sq Ft
$154
Annual Taxes
$4,635
Monthly Tax
$386
HOA
None
Tax Rate (effective)
1.16%
Sale Timeline (this listing)
| Event | Date | Price | Detail |
|---|---|---|---|
| Listed | May 27, 2026 | $400,000 | — |
| Currently listed | — | $400,000 | — |
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 every 5 minutes 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
$2,578/moPrincipal & interest
$2,076
Property tax
$386
Home insurance
$117
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 KW Coastal Virginia Chesapeake · MLS# 10636623
Data provided by REIN MLS. Information deemed reliable but not guaranteed.
$400,000
519 Windward DR, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
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