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Chesapeake Real Estate

Chesapeake at a Glance

Welcome home to Chesapeake! As Virginia’s second most populous city, Chesapeake is a mix of rural and suburban living, located in Hampton Roads just south of the James River. The sections of Chesapeake are so distinctive, you will feel as if you’re in an entirely separate place in each of them yet all under one umbrella.

  • Hickory has a rural feel with subdivisions of large homes, as well as farmland and waterfront properties, while neighboring Great Bridge is near all the modern amenities.
  • Greenbrier is the most commercial part of Chesapeake with a mall, shops and restaurants.
  • Western Branch, a recreation-based community with parks, hiking trails and sports activities, borders Portsmouth.
  • South Norfolk located along the Elizabeth River’s southern branch has undergone revitalization with the additions of apartments, condominiums and retail space.
  • Magnificently manicured Riverwalk is inviting and in the Oscar Smith school zone, which boasts an International Baccalaureate Diploma Program at its high school.

Chesapeake was rated the 21st best city in the U.S. by Bloomberg Businessweek in 2011. Its  highly ranked schools serve more than 40,000 students. Outdoor parks and trail areas scattered all over the city provide the backdrop for picnics and daytime retreats. Established neighborhoods are filled with residents who take great pride in their yards. With lots of activities, light traffic, easy parking and access to major highways, Chesapeake is a great option to call home!


Abbitt Realty. Chesapeake City Park in Chesapeake, Virginia September 26, 2022.

Chesapeake’s central location means you’re a short drive away from the thriving arts scene in Norfolk and Virginia Beach that includes the Chrysler Museum of Art, Virginia Museum of Contemporary Art and dozens of festivals. The Monitor-Merrimac Bridge-Tunnel connects the Western Branch section of Chesapeake to the Peninsula, which opens up even more options.

Children’s Museum of Virginia in Portsmouth is less than a five-minute drive from the Western Branch section of Chesapeake.

Chesapeake City Park hosts the Chesapeake Jubilee every spring and a wine festival every fall

The city offers multiple create-your-own spaces, including AR Workshop Chesapeake and one of Hampton Roads’ most popular paint your own pottery places, Glazenfyre.


Abbitt Realty. Bergey’s Breadbasket in Chesapeake, Virginia September 26, 2022.

The Butcher’s Son Chop House serves antibiotic- and hormone-free beef, pork and poultry. Enjoy authentic Neapolitan pizza at Pizzeria Bella Vista. You’ll love the view of the Intercoastal Waterway at Amber Lantern Restaurant. Build your own steam pot at Wicker’s Crab Pot Seafood. Enjoy Jamaican jerk Barbecue at Cutlass Grille. Open since 1972, Mister Jim’s is the place to go for subs and pizza.

Craft breweries continue to emerge in Hampton Roads. You’re near them all in Chesapeake, which is home to The Garage Brewery, Big Ugly Brewing and Tap It Local Chesapeake.

Bakeries are also plentiful. Check out Bergey’s Bread Basket, Whole-ly Rollers, Crave Bakery & Coffee Bar, Sweet Kream Bakery and Storybook Bakery, which offers fairytale flavor cake and filling combinations.


Chesapeake Public Schools Schools are comprised of 45 schools, including seven high schools. Middle school students can apply to the International Baccalaureate program at Oscar Smith High, the Governor’s STEM Academy at Grassfield High or the Science and Medicine Academy at Deep Creek High.

Private schools include Stonebridge School, Greenbrier Christian Academy and Atlantic Shores Christian School.

Tidewater Community College has a campus in Chesapeake. Nearby colleges and universities include Old Dominion University, Norfolk State University, Regent University, Hampton University and Christopher Newport University.


Abbitt Realty. Chesapeake Regional Healthcare in Chesapeake, Virginia September 26, 2022.

Chesapeake Regional Medical Center is located in the Greenbrier section of the city. Bon Secours Maryview Medical Center in Portsmouth and Sentara Obici Hospital in Suffolk are nearby. Chesapeake residents have access to all the major medical centers throughout Hampton Roads.


Abbitt Realty. Western Branch Park in Chesapeake, Virginia September 26, 2022.

The City of Chesapeake has an active parks and rec park system, and maintains over 80 public parks, 31 miles of multi-use trails, campgrounds, water and concert venues:

Chesapeake City Park is a jewel spread over 60 acres with two dog parks; horseshoes, volleyball and basketball courts; a skate park; a playground and imagination center; a stage for outdoor concerts; and multiple walking trails.

Called Nature’s Classroom, the Chesapeake Arboretum promotes horticultural and environmental awareness and boasts one of Virginia’s finest trail systems. Its Pecan Grove area is the perfect venue for weddings and includes a gazebo.

Lovely Oak Grove Lake Park is a mix of hardwood forest and wetlands; fish the freshwater lake.

Great Bridge Lock Park along the Intracoastal Waterway is another world — a 19-acre park where multiple yachts dock during the fall and winter. Includes a kayak/canoe launch and fishing and crabbing areas.

Lakeside Park in South Norfolk features a scenic archway bridge; a fishing pier and Veterans’ Walk Memorial are attractions.

Canoe, fish, hike, boat, play mini golf or volleyball, all at Northwest River Park and Campground.

Great Dismal Swamp National Wildlife Refuge is a respite for hikers, birders, butterfly chasers and more. It includes more than 112,000 acres of forested wetlands covering about 170 square miles. Enjoy Lake Drummond, one of only two natural lakes in Virginia.

You’ll have your pick of golf courses and be close to the abundant number of courses in Portsmouth, Suffolk and Virginia Beach. Chesapeake Golf Club was the first course built in the city. Battlefield Golf Club gives discounts to seniors, military, police and fire fighters. Greenbrier County Club has hosted the LPGA Crestar Classic. Greenbrier Sports Park features eight lighted tennis courts and two lighted softball fields. Tennis courts are free, first come, first served.

Chilled Ponds Ice Sports Complex is open for youth and adult hockey and public skating.

You and your dog will have a blast learning agility at Family Dog Club.


Abbitt Realty. Greenbrier Mall in Chesapeake, Virginia September 26, 2022.

Major supermarket chains Kroger, Food Lion, Walmart and Harris Teeter have stores in Chesapeake. Bennett’s Creek Farm Market is a hidden gem with cut-to-order meats, homemade barbecue and the best banana pudding. Find your favorite retail stores at Greenbrier Mall.

Bergey’s Bread Basket attracts folks from all over Hampton Roads and North Carolina thanks to its reputation for homemade pies, ice cream from scratch and a petting zoo on site.

Chesapeake City Park hosts a Saturday farmer’s market; most neighborhoods also have smaller farmers markets on weekends.


Chesapeake’s ideal location make it an easy commute to all the employers in Hampton Roads. Employers in Chesapeake include Sentara Healthcare, Cox Communications, QVC Chesapeake, Dollar Tree (headquarters), Coast Guard Exchange and MEB General Contractors.

Chesapeake is directly off Interstates 64 and 664. Both Newport News/Williamsburg International Airport and Norfolk International Airport are roughly 40 minutes away, a farther commute if you’re in Hickory. Chesapeake’s Western Branch section is just 20 minutes from the Amtrak station in Newport News.

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