Chesapeake, Virginia

One Increasing Purpose



Sunny Days: 211
48100 Affordability
95100 Schools
45100 Diversity
79100 Safety

Ships, like men, do poorly when the wind is directly behind, pushing them sloppily on their way so that no care is required in steering or in the management of sails; the wind seems favorable, for it blows in the direction one is heading, but actually it is destructive because it induces a relaxation in tension and skill. - James Michener, Chesapeake

The Best Thing About Chesapeake?

Beach and coastal paradise.

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 actually win the prize. Because of its maritime and military background – and location, generations run very deep in the area.

The Worst Thing About Chesapeake?

Being coastal is both amazing and at times frustrating – navigating the streets, roads and highway 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 decommissions bases the installations and surrounding neighborhoods in some situations have become neglected.
Business opportunities are tilted heavily to government and related business. This could also be seen as a good thing if you like working for the government.

Lifestyle of Chesapeake

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.

Why You Should Move Here Now?


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.

Neighborhoods in Chesapeake

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Young Professionals

Historic South Norfolk is the closest thing to a young professional in Chesapeake. Redevelopment projects, those in the past and those planned make it an increasingly cool spot for youngsters as a result of newer loft apartments and condos, office and retail space, and planned commercial district. Chesapeake is largely suburban so this is your best bet if are looking for on area on the rise for youngsters.

  • Historic South Norfolk


Dock Landing is a riverfront neighborhood with beautiful old trees, great homes and yards, and an enclosed safe feeling due to the single entrance to the streets. Most of the homes have pools for relieving the heat in summer and giving the kiddos a cool place to play. Good schools and again, plenty of yards and greenery to outdoor activities. Western Branch is another great choice. Home to some of the most highly-ranked schools in the state and beautiful homes near the water. The area also has access to great shopping, making it easy for families to stay stocked up on a daily basis.
Dock Landing

  • Western Branch
  • Greenbrier
  • Forest Lakes
  • Summer Park


Chesapeake is a great spot for retiring as long as you don’t mind your primary commercial and social activities coming from neighboring Norfolk and Virginia Beach. Chesapeake is really a suburban city but one with beautiful green spaces, neighborhoods, and retirement communities. The planned communities that rise to the top include: Lighthouse Pointe and The Reserve at Greenbrier and a great neighborhood option in South Norfolk. In addition to luxury living options it also is home to an amazing medical complex in Sentara Norfolk General Hospital.

  • South Norfolk
  • Lighthouse Pointe
  • The Reserve