0 days on market
$504,500
527 Windward Dr
Chesapeake, Virginia 23320
MLS# 10641660 · ESTATES OF GREENBRIER · Chesapeake VA
Updated 2 days ago · Source: REIN MLS
Est. payment
$3,119/mo
Edit below
Price / sq ft
$240
2,100 sq ft
Days on market
0
New listing
HOA
None
Year built
1997
29 yrs old
Beds
4
Full Baths
2
Half Baths
1
Sq Ft
2,100
Garage
Yes
Schools
- ElementaryGreenbrier Primary School—
- MiddleGreenbrier Middle School6/10
- 3/10
Info provided by GreatSchools
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…
Listed by Janice Hollowell · World Class Realty
VaHome Team property overview
527 Windward Drive is a four-bedroom, two-and-a-half-bath single-family home in Chesapeake, Virginia, built in 1997 and offering 2,100 square feet of living space on a residential lot — a solid, well-proportioned home in one of Hampton Roads' most accessible cities.
Read full property overview ↓Show less ↑
Why this home stands out
What sets 527 Windward Drive apart is its rare proximity to the USCG Finance Center Chesapeake — literally a one-minute drive — making it one of the closest privately owned residential addresses to that installation in the area. Add a 13-minute commute to Norfolk Naval Shipyard, and you have a home that genuinely works for Coast Guard and Navy households without the usual trade-off of living far from work.
ESTATES OF GREENBRIER and the Chesapeake real estate market
Chesapeake is one of the largest cities by land area on the East Coast, and that scale translates into real variety for residents. The area around Windward Drive sits within the 23320 zip code — a well-established part of the city where mature tree lines, quiet streets, and a suburban pace define everyday life. Chesapeake consistently draws families and professionals who want space, reasonable commute corridors, and proximity to the full Hampton Roads metro without the density of Norfolk or Virginia Beach. Great Bridge, Deep Creek, and the broader South Chesapeake corridor are all within easy reach, giving you access to waterways, parks, and commercial districts that feel genuinely local rather than sprawling. The city's infrastructure is strong — roads are well-maintained, and the mix of older subdivisions and newer development gives the area a lived-in, community feel. For anyone weighing where to put down roots in Hampton Roads, Chesapeake delivers a compelling case.
What's nearby
Daily life is easy from Windward Drive. Grocery stores, pharmacies, and everyday retail are all within a short drive along the major corridors connecting this part of Chesapeake. The Great Bridge area offers a solid lineup of restaurants, coffee shops, and local services. Chesapeake City Park provides walking trails, athletic fields, and open green space within the city. The Chesapeake Expressway and Interstate 64 are accessible for regional travel, connecting you to Virginia Beach, Norfolk, and the broader Hampton Roads network without a long on-ramp hunt. It's a practical, well-connected location.
For different buyers
For military families relocating
If you're stationed at the USCG Finance Center Chesapeake, you'd be hard-pressed to find a closer private-residence option — the commute is genuinely one minute. Norfolk Naval Shipyard is 13 minutes away, which also works well for Navy households. A VA loan can make ownership here straightforward, and the four-bedroom layout gives growing military families the space they actually need.
For families upgrading
Four bedrooms and 2,100 square feet give a growing family real room to spread out — a dedicated space for a home office, a guest room, or that playroom you've been wanting. Built in 1997, the home sits in a mature neighborhood with the kind of quiet, established feel that makes it easy to picture long-term. Chesapeake's parks and green spaces are close by whenever you need to get outside.
Frequently asked questions
How far is 527 Windward Drive from the USCG Finance Center Chesapeake?
The USCG Finance Center Chesapeake is approximately one minute from 527 Windward Drive — it's essentially a neighbor. This makes the address one of the most conveniently located private residences relative to that installation in the city.
How far is 527 Windward Drive from Norfolk Naval Shipyard?
Norfolk Naval Shipyard is about 13 minutes away by car under normal traffic conditions, making it a realistic daily commute for Shipyard workers and personnel.
Is 527 Windward Drive in a flood zone?
Flood zone status for this address is detailed in the FloodRisk tile on this page — check that section for the current FEMA designation and what it means practically for this property.
What is the lot and property type at 527 Windward Drive?
527 Windward Drive is a single-family residential property built in 1997, offering four bedrooms, two and a half baths, and approximately 2,100 square feet of living space in Chesapeake, Virginia.
Does 527 Windward Drive have an HOA?
HOA status for this property can vary by listing period — confirm the current HOA status and any associated rules directly with the listing agent or through the current disclosure documents.
Want to know more about 527 Windward Drive or explore comparable homes in Chesapeake? Tom and Dariya Milan at LPT Realty are ready to walk you through everything — reach out today.
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
2
Half Baths
1
Approx Sq Ft
2,100
Stories
2
Fireplaces
0
Flooring
Carpet, Ceramic, Laminate/LVP
Heating
Cooling
Laundry
Interior Features
N/A
Appliances
220 V Elec, Dishwasher, Disposal, Dryer Hookup, Elec Range, Washer Hookup
Sale & Tax History
List Price
$504,500
Price / Sq Ft
$240
Annual Taxes
$4,251
Monthly Tax
$354
HOA
None
Tax Rate (effective)
0.84%
Sale Timeline (this listing)
| Event | Date | Price | Detail |
|---|---|---|---|
| Listed | Jun 26, 2026 | $504,500 | — |
| Currently listed | — | $504,500 | — |
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
$3,119/moPrincipal & interest
$2,618
Property tax
$354
Home insurance
$147
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 World Class Realty · MLS# 10641660
Data provided by REIN MLS. Information deemed reliable but not guaranteed.
$504,500
527 Windward DR, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
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