Why this home stands out
What sets 527 Windward Drive apart is its rare combination of suburban calm and genuine walkability in Chesapeake. Within a half-mile you have dining, yoga studios, a dog park, and a full grocery run — all without getting on a highway. Add a one-minute drive to USCG Finance Center Chesapeake and a 13-minute commute to Norfolk Naval Shipyard, and this address works hard for a wide range of buyers.
ESTATES OF GREENBRIER and the Chesapeake real estate market
Chesapeake is one of the largest cities by land area on the East Coast, and the 23320 zip code sits right in the heart of it — close to the Great Dismal Swamp, the Chesapeake City Park greenway, and a dense corridor of shops and services along Greenbrier Parkway. The area around Windward Drive has a settled, tree-lined feel that comes from neighborhoods built in the late 1990s and early 2000s, when Chesapeake was expanding rapidly and planners prioritized walkable blocks and green space. Families comparing Chesapeake homes for sale often zero in on this part of the city because it threads the needle between accessibility and neighborhood quiet. You're close enough to Interstate 64 and the Chesapeake Expressway to reach Virginia Beach, Norfolk, or Portsmouth in under 30 minutes, yet the street itself stays calm. It's the kind of location that makes daily logistics feel effortless.
What's nearby
Daily life is easy here. Walmart Neighborhood Market covers your grocery run in under a mile, and for a quick coffee fix you have Wawa, a 7-Eleven, and Zeke's all within 0.6 miles. Dinner options are equally close — Zeke's, Atlas Pizza, and Ang's Sushi Bistro are all within a short walk at 0.4 miles. If staying active is part of your routine, Chesapeake Hot Yoga, TEALL Transformation Yoga, and Fit Fusion give you three solid options nearby. Fun Forest Playground, City Park Dog Park, and Chesapeake City Park round out the outdoor picture, making this one of the more walkable pockets in the zip code.
For different buyers
For military families relocating
USCG Finance Center Chesapeake is literally one minute away, which is about as short a commute as you'll find anywhere in Hampton Roads. Norfolk Naval Shipyard is 13 minutes out, keeping options open if assignments shift. A VA loan can make the path to ownership here straightforward, and the neighborhood's stability means you're not gambling on a transitional block.
More buyer questions
How far is 527 Windward Drive from USCG Finance Center Chesapeake?
The drive is roughly one minute — about as close as you can get. If you're stationed or working at the Finance Center, this address essentially eliminates your commute.
How far is 527 Windward Drive from Norfolk Naval Shipyard?
Norfolk Naval Shipyard is approximately 13 minutes away under normal traffic conditions, making 527 Windward Drive a practical choice for Shipyard personnel who want to live in Chesapeake.
What grocery stores and restaurants are near 527 Windward Drive?
Walmart Neighborhood Market is 0.5 miles away for everyday grocery needs. Within 0.4 miles you'll also find Zeke's, Atlas Pizza, and Ang's Sushi Bistro — a solid mix for weeknight dinners or a casual weekend meal.
Is 527 Windward Drive in a flood zone?
Flood zone information for this address is covered in the FloodRisk tile on this page, which pulls current FEMA map data. Review that section for the most accurate and up-to-date designation.
Are there parks near 527 Windward Drive?
Yes — Fun Forest Playground, City Park Dog Park, and Chesapeake City Park are all within 0.5 miles, giving families and pet owners easy access to outdoor space without a drive.
Tom and Dariya Milan at LPT Realty know homes for sale in Chesapeake inside and out — reach out today to ask questions or schedule a walkthrough of 527 Windward Drive.
