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Chesapeake › ESTATES OF GREENBRIER › 527 Windward Dr✓ Source: REIN MLS #10641660 · record updated Aug 5, 2026 · synced every 2 min · your inquiry is never resold
527 Windward DR, CHESAPEAKE VA 23320 - Main photo
527 Windward DR, CHESAPEAKE VA 23320 - Photo 2
527 Windward DR, CHESAPEAKE VA 23320 - Photo 3
527 Windward DR, CHESAPEAKE VA 23320 - Photo 4
527 Windward DR, CHESAPEAKE VA 23320 - Photo 5
4beds
2.1baths
2,100sqft
40days on market

527 Windward Dr, Chesapeake, VA 23320

ActiveResidential · built 1997 · ESTATES OF GREENBRIER

Facts & features

Type

Residential

Year built

1997

Price / sqft

$237

HOA fee

$23/mo

Taxes

$4,251/yr

County

Chesapeake VA

MLS #

10641660

HOA association includes

Ground Maint

$23/mo HOA fee · Estates of Greenbrier · per the REIN MLS listing record — confirm inclusions with the association.

Interior

Bedrooms
4
Full baths
2
Half baths
1
Approx. sqft
2,100
Stories
2
Flooring
Carpet, Ceramic, Laminate/LVP
Ensuite bedrooms
1
Total rooms
8
Other rooms
Attic, Breakfast Area, Foyer, PBR with Bath, Porch, Utility Closet
Appliances
220 V Elec, Dishwasher, Disposal, Dryer Hookup, Elec Range, Washer Hookup
Equipment
Cable Hookup, Ceiling Fan, Gar Door Opener, Security Sys

Construction & exterior

Style
Traditional
Subtype
Detached
Foundation
Slab
Roof
Composite
Exterior
Brick,Vinyl
Pool
No Pool
Fencing
Back Fenced,Rail

Utilities & systems

Heating
Forced Hot Air, Nat Gas
Cooling
Central Air
Water heater
Electric
Water
City/County
Sewer
City/County

Lot, parking & ownership

Subdivision
ESTATES OF GREENBRIER
Ownership
Fee Simple
Garage
Yes
Parking
Garage Att 1 Car, Multi Car, Off Street, Street
Possession
NEGOTIABLE
Disclosures
Disclosure Statement, Resale Certif Req

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

About this home

Come check out this amazing well kept two story home in the heart of Greenbrier. Conveniently located to shopping, restaurants, parks, military bases and major interstates. Roof was replaced in 2015, HVAC in 016, gutter and vinyl wrap in 2017, master shower replaced in 2022. Home features a huge master bedroom sitting area as a bonus complete with an additional fireplace! Outside folks will love the proximity to the Chesapeake City Park!Romantic gas fireplace in primary suite and more!

Listing courtesy of Janice Hollowell · World Class Realty · REIN MLS #10641660

Tom & Dariya's overview

Our read on this home

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

At a glance

Meet 527 Windward Drive—a four-bedroom, two-bath home built in 1997 with 2,100 square feet of living space. You're just minutes from USCG Finance Center Chesapeake and Norfolk Naval Shipyard. Daily life here centers on walkable dining, fitness, and parks.

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 1997-built home offers four bedrooms and over 2,100 square feet across a single-family floor plan. The lot sits in a Chesapeake neighborhood with quick access to coffee shops, restaurants, and gyms within a few blocks. You'll find homes for sale in Chesapeake in this price range often come with less convenient base proximity—this one's an exception. Nearby Fun Forest Playground and City Park Dog Park anchor the street's outdoor appeal.

ESTATES OF GREENBRIER and the Chesapeake real estate market

Windward Drive sits in an established Chesapeake neighborhood where single-family homes line quiet streets. The area balances residential calm with walkable convenience—groceries at Walmart Neighborhood Market are half a mile away, and dining options like Zeke's, Atlas Pizza, and Ang's Sushi Bistro cluster within a short walk. Chesapeake itself is Virginia's largest city by area, stretching from urban core to rural edges. You're in the closer-in portion, where commuting to Norfolk Naval Shipyard takes about 13 minutes. Anyone comparing homes for sale zoned for Indian River High School or homes for sale zoned for Greenbrier Primary School will find this address's location cuts commute time. The city's parks system is extensive—Chesapeake City Park and the dog park nearby give you outdoor options without leaving the neighborhood.

What's nearby

Daily errands are close. Walmart Neighborhood Market sits just half a mile away for groceries. Coffee and quick bites cluster within a few blocks: Zeke's (café and restaurant), 7-Eleven, Wawa, Atlas Pizza, and Ang's Sushi Bistro all sit under half a mile from your door. Fitness-focused? Chesapeake Hot Yoga, TEALL Transformation Yoga, and Fit Fusion are all nearby. Fun Forest Playground and City Park Dog Park offer outdoor recreation steps away.

For different buyers

Base commute and VA loan notes

USCG Finance Center Chesapeake is one minute away by car—nearly a commute-free posting. Norfolk Naval Shipyard runs about 13 minutes. VA loan financing is common in this area and price range. Four bedrooms and established utilities mean you can settle in quickly.

Room to grow

Four bedrooms give you space to grow—a primary suite plus three additional rooms for kids, a home office, or guest space. Over 2,100 square feet spreads across a single-family layout. The lot includes outdoor room for a yard and play space. A traditional floor plan means you can adapt rooms as your household changes.

More buyer questions

How far is 527 Windward Drive from USCG Finance Center Chesapeake?

About one minute by car. It's one of the closest commutes you'll find in the area.

What's the drive time to Norfolk Naval Shipyard?

Roughly 13 minutes, depending on traffic. It's a reasonable commute from this Chesapeake location.

Are there grocery stores and restaurants within walking distance?

Yes. Walmart Neighborhood Market is half a mile away, and dining options like Zeke's, Atlas Pizza, and Ang's Sushi Bistro sit within a few blocks.

What parks are near this address?

Fun Forest Playground and City Park Dog Park are both within a short walk. Chesapeake City Park is about half a mile away.

Does this home qualify for VA loan financing?

Yes. VA loans are widely used in this area and price range, and this single-family home meets standard lending criteria.

Ready to tour 527 Windward Drive? Contact Tom & Dariya Milan to schedule a showing and explore homes for sale in 23320.

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

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

Chesapeake$420K – $575K4+ beds

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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 (FEMA)

Source: FEMA National Flood Hazard Layer · FIRM 510034

Low / Moderate Risk

FEMA flood zone

X (low to moderate risk)

Base flood elevation

Not applicable in low-risk zones

Zone X is outside the Special Flood Hazard Area; FEMA doesn\u2019t define a BFE here.

Property elevation

20 ft above sea level

USGS 3DEP digital elevation model

Outside the high-risk Special Flood Hazard Area. Federal flood insurance is NOT required, though optional preferred-rate NFIP coverage is still worth considering in coastal Hampton Roads.

Data sources: Flood zone and base flood elevation come from FEMA\u2019s National Flood Hazard Layer. Property elevation is sampled from a single point on the parcel using the USGS National Map elevation service \u2014 actual elevations across a single property can vary by several feet higher or lower than the figure shown. Use these numbers as a starting reference and do your own due diligence (a professional survey or elevation certificate) before relying on them for any financial, insurance, or construction decision.

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.

$324K

Median sale · 12 mo

$227

Sold $/sq ft

14d

Days on market

16

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

browse Chesapeake listings →

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

$3,084/mo

Principal & interest

$2,584

Property tax

$354

Home insurance

$145

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

$375,000 – $546,000

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.

233 Downing DR · 2.4 mi · 2,046 sqft$546,000 sold 2026-08
173 Harbor Watch DR · 2.1 mi · 1,894 sqft$375,000 sold 2026-09
229 Kensington WAY · 2.6 mi · 2,078 sqft$503,000 sold 2026-07

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

Sale & Tax History

List Price

$498,000

Price / Sq Ft

$237

Annual Taxes

$4,251

Monthly Tax

$354

HOA fee

$23 / mo

Tax Rate (effective)

0.85%

Sale Timeline (this listing)

EventDatePriceDetail
ListedJun 26, 2026$498,000—
Price reducedAug 5, 2026$498,000−$6,500
Currently listed—$498,000—

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.

Market tempo

40 days on market — read it in context

Days on market reflects pricing, season, and inventory — compare it against similar nearby homes below before reading anything into it.

Questions buyers ask

Is 527 Windward 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 527 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 527 Windward Dr?+
Yes — Chesapeake Hot Yoga is about 0.3 miles away, per the cached nearby-places record for this address.
Are there parks near 527 Windward Dr?+
Fun Forest Playground is about 0.2 miles away.
Where is the nearest grocery store to 527 Windward Dr?+
Walmart Neighborhood Market is about 0.4 miles away. The closest dining on record is Zeke's (0.3 mi).
Does 527 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 527 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

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

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

Listing courtesy of Janice Hollowell · World Class Realty · REIN MLS #10641660

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.

527 Windward Dr, Chesapeake — photo

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

Call or text (757) 777-7577

527 Windward Dr, Chesapeake, Virginia 23320 · MLS #10641660 · 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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