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Chesapeake › ESTATES OF GREENBRIER › 519 Windward Dr✓ Source: REIN MLS #10636623 · record updated Jun 26, 2026 · synced every 5 min · your inquiry is never resold
519 Windward DR, CHESAPEAKE VA 23320 - Main photo
$425,000
$164 / sqft · est. $2,743/mo →
4beds
3.1baths
2,595sqft
5days on market

519 Windward Dr, Chesapeake, VA 23320

SoldResidential · built 1997 · ESTATES OF GREENBRIER

About this home

The listing, in the seller's words

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, dining, schools, and commuter routes. Property is being sold strictly as-is. Seller to make no repairs.

Listing courtesy of Patricia Lobo · KW Coastal Virginia Chesapeake · REIN MLS #10636623

VaHome team overview

Our read on this home

At a glance

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.

Read the full overview ↓

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.

More buyer 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.

Schools

Info provided by GreatSchools

Facts & features

The record, sourced

Type

Residential

Year built

1997

Price / sqft

$164

HOA fee

$28/mo

Taxes

$4,635/yr

County

Chesapeake VA

Waterfront

Yes

MLS #

10636623

HOA association includes

Ground Maint

$28/mo HOA fee · Estates of Greenbrier · per the REIN MLS listing record — confirm inclusions with the association.

Sources: REIN MLS record · null fields are suppressed, never faked

Flood & environment

The flood answer first — quantified, not buried

FEMA flood zone X · outside the high-risk area · FIRM 510034

Flood Risk

Looking up FEMA flood zone…

Hurricane Evacuation Zone

Not in a designated hurricane evacuation zone.

Source: Virginia Dept. of Emergency Management — Know Your Zone

Location intelligence

Minutes to real places, not a score

Location & Neighborhood

Places within ~1 mile, ordered by distance from this property. Powered by Google Places.

Military Commute

Drive times to nearest bases

Drive 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.

The numbers

Run the real carrying cost

Estimates only — taxes come from the public record; confirm rates with your lender. VA-eligible buyers: $0-down financing may apply.

Estimate your monthly payment

$2,743/mo

Principal & interest

$2,205

Property tax

$386

Home insurance

$124

PMI

None

HOA

$28

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.

Value & history

Judge value on real ground

Why we show no algorithmic estimate.

National AVMs misprice homes whose value drivers they can't see. Instead: the sourced assessment above, the carrying cost, real price history, and honest comparables below.

Price context — similar nearby homes

$485,000 – $700,000

The 6 most similar homes nearby (same city, within ~20% of this size, ~2.5 mi; 6 sold). Context for judging the asking price — not an appraisal or an estimate of this home's value.

813 Arcadia RD · 0.9 mi · 2,442 sqft$485,000 sold 2026-04
716 Firethorn RD · 1 mi · 2,800 sqft$630,000 sold 2026-06
407 Preservation RCH · 1.7 mi · 2,600 sqft$585,000 sold

Sale & Tax History

List Price

$425,000

Price / Sq Ft

$164

Annual Taxes

$4,635

Monthly Tax

$386

HOA fee

$28 / mo

Tax Rate (effective)

1.09%

Sale Timeline (this listing)

EventDatePriceDetail
ListedJun 21, 2026$425,000—
Price increasedJun 26, 2026$425,000+$25,000
SoldJun 25, 2026$425,000—

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:

Chesapeake Real Estate Assessor

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.

Questions buyers ask

Real questions, answered from the record

Is 519 Windward Dr in a good school zone?+
The assigned zones on the listing record are Greenbrier Intermediate (GreatSchools 6/10), Greenbrier Middle (GreatSchools 6/10), Indian River (GreatSchools 3/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 519 Windward Dr in a flood zone?+
FEMA maps this parcel in Zone X, outside the high-risk Special Flood Hazard Area. See the flood section on this page for details and sources.
Is there a gym near 519 Windward Dr?+
Yes — Chesapeake Hot Yoga is about 0.4 miles away, per the cached nearby-places record for this address.
Are there parks near 519 Windward Dr?+
Fun Forest Playground is about 0.2 miles away.
Where is the nearest grocery store to 519 Windward Dr?+
Walmart Neighborhood Market is about 0.4 miles away. The closest dining on record is Zeke's (0.4 mi).
Does 519 Windward Dr have an HOA?+
Yes — HOA dues are on record for this property (the current amount is shown in the facts section on this page). The association of record is Estates of Greenbrier. Association amenities on record include: Ground Maint.
When was 519 Windward Dr built?+
It was built in 1997, per the listing record.

Answers generated from the listing record, verified school zones, FEMA data, and cached nearby-places data — never invented.

The people

You'll talk to a person, not a lead queue

TD

Tom & Dariya Milan

LPT Realty · Hampton Roads · answer their own phone

✓ Your inquiry goes to Tom & Dariya — never sold to strangers

Listing courtesy of Patricia Lobo · KW Coastal Virginia Chesapeake · REIN MLS #10636623

Call or text (757) 777-7577

Ask Dariya — instant answers

Schools, flood, drive times, what it really costs to own — answered from this page's data, by chat or voice.

This home has sold

Curious what it means for your own plans? Ask about similar homes nearby, or what your home might sell for in this market.

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519 Windward Dr, Chesapeake, Virginia 23320 · MLS #10636623 · Source: REIN MLS + public record. Information deemed reliable but not guaranteed — verify independently. School zones subject to change; confirm with the local school division. All locations are described by neutral geographic fact. Equal Housing Opportunity.

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