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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

324 Scone Castle Loop, Chesapeake, VA - $2,395,000

Residential, Detached
  • 5 Beds
  • 6 Baths
  • 7,102 SQFT
  • 147 DOM
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This Is A Gorgeous, Unique Country French Home That You Must See To Appreciate!! The Exterior Walls Are Constructed Of Lime-stone And The Eco Roof Has A 50-year Life. All Of The Stair Railings And The Doors For The Wine Room Are Hand Custom-desi...

3812 Bruce Rd, Chesapeake, VA - $2,350,000

Residential, Detached
  • 7 Beds
  • 7 Baths
  • 9,713 SQFT
  • 97 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...

517 Thistley Ln, Chesapeake, VA - $1,250,000

Residential, Detached
  • 6 Beds
  • 7 Baths
  • 7,600 SQFT
  • 465 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...

404 Mill Stone Rd, Chesapeake, VA - $1,200,000

Residential, Detached
  • 4 Beds
  • 6 Baths
  • 11.5k SQFT
  • 22 DOM
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Spectacular Custom Built Home On 3 Acres In Hickory School District. Huge Wide-open Floor Plan With Updated Kitchen And Baths. Modern Gallery Entrance With Two Story Curved Staircase. Multiple Options For Room Usage With Third Floor Media Room, Fi...

1409 Paul Eason Dr, Chesapeake, VA - $1,100,000

Residential, Detached
  • 5 Beds
  • 6 Baths
  • 6,329 SQFT
  • 127 DOM
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Builder's Personal Home With No Expense Spared. Thermador Appliances, Cook Top, Double Oven. Full Outdoor Kitchen Overlooking The Pool. Pool House With A Full Bathroom And Separate Garage Area. Detached Garage Complete With An Upstairs Apartment, ...

1310 Prestwick Ct, Chesapeake, VA - $985,000

Residential, Detached
  • 5 Beds
  • 7 Baths
  • 6,173 SQFT
  • 112 DOM
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One Of A Kind Home Built By Don Borte. 5 Bedrooms, 5 Full Baths, 2 Half Baths, Lutron Lighting System. Home Audio System With Sono's In All Rooms. Whole House Generator. Security System With Cameras. Updated Led Lighting. Over 6,000 Sq Ft, Open Fl...



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: 1,401
Average Price: $336,178
Highest Price: $2,395,000
Lowest Price: $40,000

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