527 Windward Dr was listed for sale on Jun 26, 2026. The last list price was $498,000. It came off the market on Oct 28, 2026. It is not listed for sale in the REIN MLS.
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
Facts & features
TypeResidential
Year built1997
Price / sqft$237
HOA fee$23/mo
Taxes$4,251/yr
CountyChesapeake 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
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.
How Far Is?
Driving distance by road and typical drive time via Google Maps, to the nearest location of each.
Also nearby
Distances are straight-line (as the crow flies) from this property, not driving miles. Places within ~1 mile, nearest first. Powered by Google Places.
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Military Commute
Drive times to nearest bases
🚢
USCG Finance Ctr
Coast Guard
3min·1mi
⚓
NNSY
Navy
25min·13.1mi
🚢
USCG Portsmouth
Coast Guard
24min·10.8mi
⚓
NMCP
Navy
28min·13.4mi
⚓
NAS Oceana
Navy
37min·16.5mi
Typical drive times from Google Maps, without live traffic. Rush hour and tunnel backups can add time.
Flood & environmentFlood risk (FEMA)
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’t 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’s National Flood Hazard Layer. Property elevation is sampled from a single point on the parcel using the USGS National Map elevation service — 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.
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.
$315KMedian sale · 12 mo
$226Sold $/sq ft
15dDays on market
17For sale now
$88KHH income
76.1%Owner-occupied
REIN MLS closed sales, trailing 12 mo · U.S. Census ACS 2024 5-year
Price context: similar nearby homes$324,000 – $529,900The 6 most similar homes nearby (same city, within ~20% of this size, ~2.5 mi; 6 sold). Context for the last list price, not an appraisal or an estimate of this home's value.
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.
CompareThis home next to what else is for sale nearby
Home
Price
Beds
Baths
Sqft
$ / sqft
527 Windward Drthis home, last list price
$498,000
4
2.1
2,100
$237
Loading nearby homes for sale…
Active comparables from the REIN MLS, the same homes shown under Comparable Properties. Context for judging the asking price, not an appraisal.
Questions about this home
Is 527 Windward Dr in a good school zone?
The assigned zones on the listing record are Greenbrier Primary, Greenbrier Middle (VaHome School Score 7.1/10), Indian River (VaHome School Score 4.3/10). 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.
Off the marketSee what this home is worth now
This home is not listed for sale in the REIN MLS. The home value tool estimates a current value from recent nearby sales.
Listing courtesy of Janice Hollowell · World Class Realty · REIN MLS #10641660
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.
