Living in Chesapeake VA | Housing, Schools, Attractions | Long & Foster

Living in Chesapeake, VA

With a population of around 230,000, Chesapeake gives you that small-town feel and low-key lifestyle. As one of the Seven Cities that make up the Hampton Roads section of Virginia, Chesapeake offers the excellent schools, great shopping, and easy access to entertainment that Hampton Roads is known for. Boating enthusiasts will also love the access to the Intracoastal Waterway and rivers.

great bridge bridge chesapeake va

Things to Do in Chesapeake, Virginia

Southern hospitality and warm weather make living in Chesapeake pleasant and enjoyable. Chesapeake is full of outstanding parks like Oak Grove Lake Park or the Dismal Swamp Canal Trail. Go fishing at the Northwest River Park and Campground, or take a canoe up the Dismal Swamp Canal, where Edgar Allen Poe is rumored to have penned "The Raven." The bird watching along the canal is some of the best in area. Chesapeake is also home to forest land and protected wetlands, making it a great place to explore the outdoors and experience the native flora and fauna. Open from mid-June through mid-November, the Chesapeake Farmers' Market is also a prime attraction in the area. 

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Homes for Sale in Chesapeake

Chesapeake real estate runs the gamut from cozy starter homes to grand estates. You’ll find condos, townhomes, apartments, and single-family-home communities of all price ranges. If you are looking for a brand new home, Chesapeake offers many new construction communities. Chesapeake also has a large inventory of waterfront homes or houses with access to the water. If you desire more land, Chesapeake offers communities with acreage, as well as farms.

Some neighborhoods to keep an eye out for include Great Bridge/Hickory, a centrally located neighborhood that features waterfront condos with private boat slips. Grassfield/Deep Creek is a tight-knit neighborhood on the Intracoastal Waterway, where you can find homes of varying styles and age, in addition to new construction. Greenbrier is home to many fine restaurants, shopping centers, movie theaters, and recreation. Western Branch is located in the western part of the city and offers many residential neighborhoods, shopping opportunities, waterfront neighborhoods, and affordable living for all lifestyles.

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Chesapeake: Where Urban and Rural Lifestyles Co-Exist

Chesapeake is a city full of small, well-established neighborhoods. Easy access to all types of outdoor activities, an active music scene, and lots of cultural events are what give it a very welcoming feel. Where else could you find a bakery that has an attached petting zoo? At Bergey's Breadbasket, you can enjoy some strawberry pie and spend some time playing with a baby goat! Golfers will also feel right at home in Chesapeake, with its selection of golf courses and communities.

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Getting Around Chesapeake

While the City of Chesapeake is not located on the Chesapeake Bay, you are not too far away to enjoy it. It's just about 30 minutes from Chesapeake 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.

Chesapeake is home to the Naval Auxiliary Landing Field Fentress and the U.S. Coast Guard Base in the southern portion of the city. Chesapeake Regional Medical Center is centrally located within the city, and you have easy access to other medical facilities throughout Hampton Roads, including Naval Medical Center Portsmouth for active and retired military.


Getting There & Around


What Locals Love

Don't Miss It

  • Go boating, fishing, or bird watching at Dismal Swamp Canal, the oldest continuously operating man made canal in the United States where Edgar Allen Poe is rumored to have written “The Raven”.
  • A must-see is the Chesapeake Christmas parade. The week prior to the parade, many residents put out lawn chairs to reserve their curbside spot to have the best vantage point to enjoy the parade.
  • At Northwest River Park and Campground Camping, go boating, fishing, hiking, or enjoying a game of putt-putt, volleyball, or horse shoes.


Chesapeake Real Estate at a Glance

  • 951 Homes Sold*
  • 49 Avg. Days on Market*
  • $489,949 Median Price*

*over last 3 months

Find Your Home in Chesapeake

There Are 803 Properties Available in Chesapeake



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