Chesapeake, Virginia

A natural harbor makes for one of the best ports on the East Coast, and shipping and shipbuilding activity along with fishing and seaport-related commerce. With this level of access to all types of water (ocean, bays, Inter-coastal, rivers, swamp), it could turn any landlubber into a water-lover overnight. The military plays a huge part in life here – It is the number 2 destination in the county for military retiree’s. Many places claim to be “a family,” but Chesapeake might win the prize. Because of its maritime and military background – and location, generations run very deep in the area.

Being coastal is both amazing and, at times, frustrating – navigating the streets, roads, and highways in and around the area requires crossing several bridges and tunnels, and without a metro rail and limited mass transit, this makes for very unpredictable travel times. As the military decommission bases, the installations and surrounding neighborhoods in some situations have become neglected. Business opportunities are tilted heavily toward government and related business. This could also be seen as a good thing if you work for the government.

We highly recommend visiting Chesapeake and staying in the community in a VRBO rather than a hotel to get a feel for what it's like to live among the locals. You can receive discounted fares on travel via our partnership with Expedia as well.

Chesapeake is roughly divided into 4 area’s – in 3 of the four, Western Branch, Deep Creek and Greenbrier, single family homes, of varying lot sizes, dominate. Most have front and backyards which play a big part of living here.

The South Norfolk neighborhood (officially part of the city of Chesapeake) has been undergoing a transformation and is emerging as a more urban area featuring a mix of revitalized loft spaces, row houses and a few eclectic shops and cafés. This area is unique compared to other neighborhoods, which tend to have a feel of the suburbs. Most of the city retail zones are mall-like/big box. The restaurants are a mix of fast-casual, national or regional chains. With entertainment and dining options somewhat limited you may need to be prepared to make your own fun and dinner.

Compared to many East Coast seaside cities Chesapeake remains relatively undiscovered. It is easily possible to find great real estate value pockets on classic southern homes. The sense of community is apparent in every nook and cranny of the area. People here are very friendly. And if you strike up a conversation about boating or the Navy you may be in for a nice long chat. The pace is not brisk which suits the local’s just fine.