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One of the fastest growing cities in Hampton Roads for the past ten years, Chesapeake serves as a family-friendly refuge from the bustle of its surrounding cities.

Homes For Sale in the City of Chesapeake

Sort listings by:Price, Highest First

3812 Bruce Rd, Chesapeake, VA - $2,100,000

Residential, Detached
  • 7 Beds
  • 7 Baths
  • 9,713 SQFT
  • 394 DOM
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Fabulous 3 Acre Estate With 600' Of Prime Waterfront, 1500sf Boathouse Condo, Dock, 4 Boat/jetski Lifts, Boat Launch And 2000sf In-law Suite. Impressive Gated Entrance To The Property With And A Long And Lovely Driveway Of Pavers, Bridge, Pond And...

1513 Bankbury Way, Chesapeake, VA - $1,500,000

Residential, Detached
  • 4 Beds
  • 4 Baths
  • 6,000 SQFT
  • 28 DOM
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**3rd Seller Who Must Be Added To Purchase Offer Is Li Hsueh Lu.** This Dream Home Was The 2007 Home-a-rama Home Called "the Dynasty". Built With All Of The Builder Upgrades Imaginable. White Alba Brick, 13 Incredible Chandeliers, High & Dramatic...

3900 Oak Dr E, Chesapeake, VA - $1,299,000

Residential, Detached
  • 6 Beds
  • 8 Baths
  • 6,078 SQFT
  • 101 DOM
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Awe Inspiring Estate With Private Entry And Backyard Peninsula! All Brick Georgian With 3 Levels Of Space With Breathtaking Views Of Sterns Creek! Cook's Kitchen With Dual Ovens & Dishwashers. Sub Zero Fridge And Oversized Center Island. Game ...

517 Thistley Ln, Chesapeake, VA - $1,199,000

Residential, Detached
  • 6 Beds
  • 7 Baths
  • 7,600 SQFT
  • 35 DOM
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This Executive Home Offers Space For Your Family And Friends, As Well As An Elegant Retreat From The Hectic Pace Of A Busy Life. This Home Offers Over 7,000 Square Feet And A Full Mother In Law Suite, Or Guest Apartment; Complete With Additional K...

401 Meadowlark Ln, Chesapeake, VA - $1,102,937

Residential, Detached
  • 4 Beds
  • 4 Baths
  • 3,662 SQFT
  • 194 DOM
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This Is A Custom Home Being Built For A Specific Client's Needs. And Your New Home In '19 Could Be Next! Only 5 Lots Remain At Beaver Dam Estates. Choose One Of Our Plans Or Bring Us One Of Your! This Home Comes Complete With: All Brick, Single Le...

441 Centerville Tpke S, Chesapeake, VA - $1,000,000

Residential, Detached
  • 4 Beds
  • 3 Baths
  • 2,611 SQFT
  • 45 DOM
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Lots Of Potential! 3 Acres Zoned For Horses In The Heart Of Hickory. The Value Is In The Land! Great Opportunity For Possible Re-zoning For Commercial Use. The Home Is Not In Livable Condition.



What's My Home Worth?


Come home to Chesapeake and experience the big city feel in a small town setting. It’s all here: historically distinct communities, scenic farmlands, expansive woodlands, and pristine wetlands. Chesapeake is a part of “Coastal Virginia,” and is considered one of the top six recreational areas in the country. It’s also consistently ranked as one of the five safest cities of its size in the country.

Real Estate Statistics

Total Listings: 1,305
Average Price: $351,095
Highest Price: $2,100,000
Lowest Price: $39,999

More information about the City of Chesapeake

Recently named by Money Magazine as "One of the Best Cities in America" to raise a family, Chesapeake remains close enough so that its residents enjoy just a short drive to the culture and entertainment found in the area. Neighborhoods throughout Chesapeake have developed a strong sense of community by sponsoring their own events, festivals, and volunteer activities. .As it borders Norfolk, Portsmouth, and North Carolina, the City of Chesapeake is diverse with endless potential for outdoor activities as well as superb shopping and dining. 

Residents of Chesapeake enjoy the following benefits:

  • Waterfront property on the Atlantic Intracoastal Waterway
  • Several parks and recreational opportunities (Great Dismal Swamp Wildlife Refuge, Chesapeake City Park, Chesapeake Arboretum, Northwest River Park, Fun Forest, Oak Grove Lake Park, and many more!)
  • Chesapeake Planetarium
  • Locally-owned restaurants, including Rose Bay Seafood, Amber Lantern, and Passion
  • New Theatre of Chesapeake
  • Annual festivals and events (Chesapeake Jubilee, Chesapeake Wine Festival, American Indian Festival, Symphony Under the Stars)
  • A short drive to the dining, shopping, and cultural opportunities of Norfolk, Portsmouth, and Virginia Beach