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Chesapeake › ESTATES OF GREENBRIER › 526 Windward Drive Dr✓ Source: REIN MLS #10653125 · record updated Sep 18, 2026 · synced every 2 min · your inquiry is never resold
526 Windward Drive DR, CHESAPEAKE VA 23320 - Main photo
526 Windward Drive DR, CHESAPEAKE VA 23320 - Photo 2
526 Windward Drive DR, CHESAPEAKE VA 23320 - Photo 3
526 Windward Drive DR, CHESAPEAKE VA 23320 - Photo 4
3beds
2.1baths
1,471sqft
8days on market

526 Windward Drive Dr, Chesapeake, VA 23320

Under ContractResidential · built 1996 · ESTATES OF GREENBRIER

Facts & features

Type

Residential

Year built

1996

Price / sqft

$197

HOA fee

$23/mo

Taxes

$3,621/yr

County

Chesapeake VA

MLS #

10653125

Interior

Bedrooms
3
Full baths
2
Half baths
1
Approx. sqft
1,471
Stories
2
Flooring
Carpet, Ceramic, Laminate/LVP
Ensuite bedrooms
1
Total rooms
6
Other rooms
PBR with Bath
Appliances
Dishwasher, Disposal, Dryer, Dryer Hookup, Elec Range, Refrigerator, Washer, Washer Hookup
Equipment
Cable Hookup, Ceiling Fan
Accessibility
Lift

Construction & exterior

Style
Contemp, Traditional
Subtype
Detached
Foundation
Slab
Roof
Asphalt Shingle
Exterior
Vinyl
Pool
No Pool
Fencing
Back Fenced,Full,Wood Fence

Utilities & systems

Heating
Heat Pump
Cooling
Central Air
Water heater
Gas
Water
City/County
Sewer
City/County

Lot, parking & ownership

Subdivision
ESTATES OF GREENBRIER
Zoning
PUD
Ownership
Fee Simple
Garage
Yes
Parking
Garage Att 2 Car, Driveway Spc
Possession
SETTLEMENT
Miscellaneous
Fixer Upper
Disclosures
Common Interest Community, Short/Comp Sale

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

About this home

Short sale — offer accepted and currently pending lender approval.

Listing courtesy of Jonathan Mironchik · LPT Realty LLC · REIN MLS #10653125

Tom & Dariya's overview

Our read on this home

by Tom & Dariya Milan, REALTORS® · Brokered by LPT Realty

At a glance

Three-bedroom, two-bath home built in 1996 on Windward Drive in Chesapeake. Just over 1,400 square feet with solid bones and convenient access to shopping, dining, and recreation. A short commute to major employers and military installations.

Keep searching in Chesapeake

See all Chesapeake homes for sale, including homes for sale in 23320, homes for sale zoned for Indian River High School, and homes for sale zoned for Greenbrier Primary School. Browse every listing among homes for sale in Chesapeake — updated from the REIN MLS every few minutes. Nearby, look at Greenbrier homes for sale, Chesapeake waterfront homes for sale, Chesapeake condos and townhomes for sale, and new construction homes in Chesapeake.

Read the full overview ↓

Why this home stands out

This 1996-built home sits in a walkable pocket of Chesapeake where daily errands are quick and neighbors are close. You're steps from coffee shops, restaurants, and parks—Zeke's, Atlas Pizza, and Fun Forest Playground are all within a few blocks. The layout gives you three bedrooms and two full baths in a compact footprint, making it efficient to heat, cool, and maintain.

ESTATES OF GREENBRIER and the Chesapeake real estate market

Windward Drive is a quiet residential street in the heart of Chesapeake, where tree-lined blocks and modest homes create a stable, neighborly feel. The area is well-served by local commerce: grocery shopping at Walmart Neighborhood Market, dining at Zeke's or Ang's Sushi Bistro, and fitness options like Chesapeake Hot Yoga and TEALL Transformation Yoga are all within walking distance or a short drive. Chesapeake itself is Virginia's second-largest city by area, sprawling across the southeastern corner of Hampton Roads with a mix of waterfront communities, suburban neighborhoods, and commercial corridors. Getting around is straightforward on local roads; the city connects easily to Norfolk Naval Shipyard and other regional employment hubs. If you're comparing homes for sale in Chesapeake, note that this zip code, 23320, offers that rare combination of walkable errands and quick commutes. Parks like City Park Dog Park and Chesapeake City Park give you outdoor space without leaving the neighborhood.

What's nearby

You're surrounded by convenience. Zeke's coffee shop and Atlas Pizza sit just 0.4 miles away, perfect for quick mornings or casual dinners. Walmart Neighborhood Market is half a mile for groceries. Fitness is close too: Chesapeake Hot Yoga and TEALL Transformation Yoga are both within a short walk, and Fit Fusion is less than a mile away. Fun Forest Playground and City Park Dog Park offer green space for kids and pets, while Chesapeake City Park provides wider recreational grounds nearby.

For different buyers

Base commute and VA loan notes

About one minute to USCG Finance Center Chesapeake and thirteen minutes to Norfolk Naval Shipyard. VA loan financing is widely available in this area, and the home's straightforward layout and modest size mean fewer moving costs and faster closing timelines. You're close enough to base that daily commutes are painless.

Room to grow

Three bedrooms and two full baths give you room to spread out without excess space to maintain. The compact 1,471 square feet means lower utility costs and easier upkeep. A fenced yard and proximity to Fun Forest Playground and City Park Dog Park make outdoor time accessible. Storage is efficient, and the 1996 construction keeps the bones solid for your family's needs.

More buyer questions

How far is 526 Windward Drive from Norfolk Naval Shipyard?

About thirteen minutes by car. USCG Finance Center Chesapeake is even closer—roughly one minute away.

What schools are nearby?

The home falls within the attendance zones for homes for sale zoned for Greenbrier Primary School and homes for sale zoned for Indian River High School. Check Chesapeake Public Schools' website for current boundaries and school details.

Are there parks and playgrounds in the area?

Yes. Fun Forest Playground, City Park Dog Park, and Chesapeake City Park are all within half a mile, offering space for kids and pets.

What grocery and dining options are close by?

Walmart Neighborhood Market is 0.5 miles away for groceries. Zeke's, Atlas Pizza, and Ang's Sushi Bistro are all within 0.4 miles for dining.

Is the neighborhood walkable?

Yes. Coffee shops, restaurants, gyms, and parks are within walking distance or a short drive, making daily errands convenient.

Interested in 526 Windward Drive or other homes for sale in 23320? Contact Tom & Dariya Milan to schedule a tour today.

Summary generated by AI from public records and publicly available information.

Homes like this one sell fast — see the next one first

Chesapeake$245K – $335K3+ beds

By subscribing you agree to receive listing emails from Tom & Dariya Milan, Realtors, at most one a day. Unsubscribe anytime · Privacy PolicyBrokered by LPT Realty

Schools

VaHome School Score

Our own 1–10 rating, scored from Virginia Department of Education data.

VaHome School Score — calculated by VaHome.com from Virginia Department of Education assessment, progress, and attendance data. Attendance zones come from the MLS listing record; confirm the current zone with the school division before making an offer.

Flood & environment

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

Explore this neighborhood

Greenbrier

Greenbrier is a neighborhood in Chesapeake, Virginia. It has a suburban setting with streets lined with trees and well-kept homes. The area mixes single-family homes with settled properties.

$325K

Median sale · 12 mo

$229

Sold $/sq ft

14d

Days on market

20

For sale now

$88K

HH income

76.1%

Owner-occupied

REIN MLS closed sales, trailing 12 mo · U.S. Census ACS 2024 5-year

Explore Greenbrier →
Map of Greenbrier with neighborhood boundaryNeighborhood

Chesapeake homes for sale →

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

$1,891/mo

Principal & interest

$1,505

Property tax

$302

Home insurance

$85

PMI

None

HOA/Condo (paid separately)

$23

Estimate only. Association (HOA/condo) fees are paid separately and are not included in the payment above. 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

Price context — similar nearby homes

$287,500 – $385,000

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.

133 Mann DR · 2.3 mi · 1,483 sqft$385,000 sold 2026-06
7 Harbor Watch DR #221 · 2.1 mi · 1,668 sqft$315,000 sold 2026-09
149 Horse Run DR · 2.8 mi · 1,462 sqft$311,000 sold 2026-03

Own a home nearby? See what it is worth today — What's your Chesapeake home worth?

Sale & Tax History

List Price

$290,000

Price / Sq Ft

$197

Annual Taxes

$3,621

Monthly Tax

$302

HOA fee

$23 / mo

Tax Rate (effective)

1.25%

Sale Timeline (this listing)

EventDatePriceDetail
ListedSep 11, 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:

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

Is 526 Windward Drive Dr in a good school zone?+
The assigned zones on the listing record are Greenbrier Primary, Greenbrier Middle (VaHome School Score 7.2/10), Indian River (VaHome School Score 4.9/10). School attendance zones can change — always confirm enrollment with the local school division.
Is 526 Windward Drive 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.
Does 526 Windward Drive 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 NA.
When was 526 Windward Drive Dr built?+
It was built in 1996, 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

Brokered by LPT Realty · Hampton Roads · answer their own phone

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

Listing courtesy of Jonathan Mironchik · LPT Realty LLC · REIN MLS #10653125

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.

Schedule a private tour

Free, no obligation — your inquiry goes to Tom & Dariya, never resold.

526 Windward Drive Dr, Chesapeake — photo

See it in person — the record only says so much.

Call or text (757) 777-7577

526 Windward Drive Dr, Chesapeake, Virginia 23320 · MLS #10653125 · 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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