Chesapeake, Virginia

One Increasing Purpose

Looklyloo Score: 74

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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