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.
More buyer 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.
