Best Neighborhoods in Chesapeake, VA

Chesapeake, Virginia, is one of several cities in the southern section of what is called Hampton Roads.

A large area that borders 4 other great cities. It is surrounded by many waterways that require bridges or tunnels to connect the cities. On one side of Chesapeake borders Virginia Beach and Norfolk, on the far side it borders Suffolk and Portsmouth.

Deep Creek

The Grassfield/Deep Creek area is a friendly neighborhood on the Intracoastal Waterway, where you can find homes of various styles, age, and even new construction. Residents enjoy the peaceful environment. Deep Creek also is a suburban community, which maintains some of its original rural character.

You'll find that Is divided into North and South areas. There's suburban commercial and residential areas in the northern portion and a vast area of undeveloped forests and wetlands along its southern perimeter. This area is also a neighbor to a large portion of the Great Dismal Swamp National Wildlife Refuge.

Homes for sale in Deep Creek area | Deep Creek high school homes

Great Bridge

Great Bridge is a centrally located neighborhood that features primarily made up of medium sized to large single-family homes, townhomes and waterfront condos with private boat slips. It is home to the Great Bridge middle and high schools and is also where the central library of Chesapeake is located.

Great Bridge was essentially a small town or crossroads until the late 1980s and 1990s, when it experienced significant growth. So it now contains large residential areas as well as many large shopping centers.

A 35 min drive to the VB Oceanfront, 26 minutes from the Norfolk International Airport, 20 minutes from the Greenbriar Area.

Houses For Sale in Great Bridge, Virginia


Hickory is along the southern edge of Chesapeake near the North Carolina-Virginia border. Most of Hickory is either rural farmland or wealthy suburban neighborhoods. This area has a highly ranked high school, Hickory High school.

Residents in Hickory enjoy a quiet, country setting that is also close to parks, shopping, dining, schools and more. You’ll find a family-friendly community with residents of all ages. Students living here will attend Hickory Elementary, Hickory Middle and Hickory High Schools. All the schools are in close proximity to each other, making it easier on parents with children in different grades.

The Hickory section of Chesapeake, Virginia is one of the fastest growing areas of Hampton Roads.

Houses For Sale in Hickory, VA

Western Branch

Western Branch is along the western part of Chesapeake near Suffolk, VA and offers many residential neighborhoods, shopping opportunities, waterfront neighborhoods, and affordable living for all lifestyles. This are is also the northernmost borough of Chesapeake. It got its name because the western branch of the Elizabeth River is its eastern border.

Western Branch is well established but not necessarily older. It's also a relatively small area. This area is very suburban with mostly single family homes and a few apartment complexes on the edge. All the schools are located in the same general neighborhood.

Very close to the highway for easy access to the rest of Hampton Roads. 5 Minutes from Chesapeake Square Mall, 15 minutes to Norfolk, VA.

Homes For Sale in Western Branch, Chesapeake


The community of Greenbrier is conveniently situated in the middle of Chesapeake’s main commercial area with popular restaurants, many shopping centers, movie theaters, and recreational activities to enjoy! While the City of Chesapeake is not located on the Chesapeake Bay, you are not too far away to enjoy it.

Just about 30 minutes to the Virginia Beach oceanfront and the Chesapeake Bay, about 90 minutes to the Outer Banks of North Carolina, and about 45 minutes to Williamsburg. Very convenient commute to the Highway too!

Homes For Sale in Greenbrier, Chesapeake, VA