Top Chesapeake VA Neighborhoods for Military Relocation

by Jason Edwards

Chesapeake continues to be one of Hampton Roads’ most popular destinations for military families — and for good reason. You get space, stability, strong commutes, and neighborhoods that feel genuinely family-friendly. As someone who spent 20 years in the Navy and now helps families relocate here every week, I know how important it is to find an area that fits your lifestyle and your timeline.

Whether you’re PCSing to Norfolk Naval Base, commuting to Portsmouth Naval Hospital, or heading to NAS Oceana, this guide breaks down the areas that consistently rise to the top for military and VA buyers.

Why Military Families Love Chesapeake

Chesapeake offers a unique mix of convenience and breathing room. You can still find larger homes (the average is over 2,200 square feet), bigger yards, and quieter streets — but you’re not way out in the country.

A few quick stats from our local MLS as of 2025:

Median home price: $411,750 (+3.7% YoY)
Median days on market: 20
Active inventory: 768 homes (+21.7% YoY)

Plus, you get:

Lower flood risk vs. coastal cities
Strong military presence and stable demand
New construction availability
Easy access to all major bases via I-64, Route 168, and the Jordan Bridge

For families who want balance, it hits the sweet spot.

Great Bridge — The Gold Standard for Families

If Chesapeake had a “classic family suburb” trophy, Great Bridge would win it every year. It’s one of the most established and stable sections of the city, known for wide streets, mature trees, and neighborhoods designed for day-to-day family life.

Homes typically fall in the low-to-mid $400Ks, and the area stays in demand because it just… works. Everything from parks to grocery stores is close by. Commutes to Norfolk Naval Base run around 25–30 minutes depending on traffic.

Local Tip: Great Bridge is a favorite for dual-military families or anyone who wants predictability and strong resale stability.

Grassfield — Newer, Spacious, and PCS-Friendly

Grassfield is one of Chesapeake’s fastest-growing areas thanks to its newer construction and open layouts. Most homes were built after 2015, which makes them VA-loan-friendly with minimal inspection surprises.

Expect high $300Ks to mid-$500Ks for most properties, with quick access to the 168 bypass — a major win for commutes to Portsmouth Naval Hospital or anywhere westbound.

If you want “turn-key and modern,” Grassfield belongs on your shortlist.

Hickory — Space, Schools, and Quiet Country Vibes

Hickory gives you the best of both worlds: suburban stability with a touch of rural calm. Homes on larger lots are common, and the area is known for peaceful evenings, starry skies, and a slower pace.

Prices usually start around the mid-$400Ks and go up. Commutes to Norfolk Naval Base run about 30–35 minutes — but you’ll likely enjoy that drive more than most. If you’re craving space after living on base or in a dense city, Hickory hits the mark.

Homeowner angle: Hickory properties tend to hold value well because a lot of families seek larger lots once they outgrow their first home.

Greenbrier — Convenience Meets Comfort

Greenbrier is the most “city-adjacent” part of Chesapeake. If you want everything within a 10-minute radius — shopping, restaurants, gyms, coffee, the whole nine — this is your spot.

Homes generally sit in the mid-$300Ks to low-$500Ks, and commute routes are extremely flexible, whether you’re heading to Norfolk, Portsmouth, or Virginia Beach.

For military families juggling deployment schedules, Greenbrier’s convenience can take a lot of pressure off everyday routines.

Deep Creek — Affordable and Underrated

Deep Creek doesn’t always show up on Top 10 lists, but it should. With homes in the low-to-mid $300Ks, it’s one of the most budget-friendly parts of Chesapeake without sacrificing access or amenities.

It’s also a quick shot to the Jordan Bridge — a major shortcut to Norfolk Naval Base or Portsmouth Naval Hospital.

If you’re a first-time VA buyer looking for value, this is one of the best places to start.

Western Branch — The Commuter Sweet Spot

Western Branch sits right on the edge of Portsmouth and gives families easy access to I-664 — one of the least chaotic commutes during rush hour. Homes typically stay in the low $400Ks and offer a great blend of value and convenience.

If you or your spouse work at both Norfolk Naval Base and Portsmouth Naval Hospital, this area can literally save hours a week.

South Norfolk — Historic Character and Revitalization

South Norfolk is one of Chesapeake’s oldest sections, featuring historic homes and redevelopment efforts that have been underway for several years. Home prices tend to fall in the mid-$200Ks to low-$300Ks, which makes it an appealing option for buyers looking for affordability and architectural character.

It’s also minutes from Downtown Norfolk via the Campostella Bridge.

Local Spotlight: Northwest River Park

Located just south of Hickory, Northwest River Park offers trails, kayaking, camping areas, and one of the best “reset spots” in the entire city. If you’re new to Chesapeake, it’s an easy way to get a feel for the area’s outdoor lifestyle.

Which Chesapeake Neighborhood Fits Your Move?

When choosing an area, military families should consider:

Commute realities (search at 7 a.m., not noon)
Lifestyle preferences (suburban vs. acreage vs. convenience)
Maintenance needs (newer build vs. established home)
Budget + resale potential
Proximity to childcare, activities, and daily routines

If you’re comparing neighborhoods or trying to match your VA loan budget to the right area, I’m happy to walk you through it.

Closing & CTAs

For buyers & relocators:
📺 Watch the full YouTube breakdown: https://youtu.be/sqLfDzaPiyw
📘 Download my free Buyer’s Guide: https://realtorjedwards.com/buyer-guide
📅 Book a quick discovery call: https://calendly.com/jedwrds/discovery-phone-call

For current homeowners:
Share this with a friend who’s PCSing or thinking about moving here — or hit reply and I’ll send you a quick, no-pressure home value update.