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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 - $2,199,000

Residential, Detached
  • 5 Beds
  • 7 Baths
  • 7,102 SQFT
  • 70 DOM
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Welcome To One Of Hampton Roads Most Artistic Homes. One Of A Kind Estate Built W/every Aspect Of Quality & Eclectic Mediterranean Decor. Situated On A Private Lake In The Heart Of Hickory, This World Class Home Offers 5 Bdrms, 4 Full & 2 Half Bat...

340 Scone Castle Loop, Chesapeake, VA - $1,975,000

Residential, Detached
  • 5 Beds
  • 6 Baths
  • 7,146 SQFT
  • 100 DOM
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Once In A Rare Opportunity Will A Truly Magnificent Home Of This Magnitude Be Available. Hand-picked Custom Builder Built Without Compromise, The Home Reflects Only The Very Best And Unbelievable Custom Features, From The Mahogany Wood Floors & St...

3812 Bruce Rd, Chesapeake, VA - $1,950,000

Residential, Detached
  • 7 Beds
  • 7 Baths
  • 9,713 SQFT
  • 13 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...

MLS Number 10290183 in the city of Chesapeake Homes for Sale by Whispering Pines S., the zipcode of 23322

909 Unicorn Trl, Chesapeake, VA - $1,500,000

Residential, Detached
  • 5 Beds
  • 4 Baths
  • 4,035 SQFT
  • 4 DOM
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Once In A Lifetime Opportunity To Own A Magnificent Cedar Log Home Resting On Over 23 Sprawling Acres Of Prime Real Estate In The Heart Of Great Bridge, Chesapeake. Total Seclusion And Privacy With Front Iron Security Gate, Video Security System,...

429 Head Of River Rd, Chesapeake, VA - $1,500,000

Residential, Detached
  • 4 Beds
  • 3 Baths
  • 3,202 SQFT
  • 16 DOM
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Welcome To The River Ranch Farm. This Home Is Being Sold As-is, This Home Is Move In Ready, It's Gorgeous! It Is The Wide Open Feel Like Wyoming, And The Welcoming Pastures Like Kentucky. You Are Greeted By The Large Foyer And Soaring Vaulted Ceil...

1337 Simon Dr, Chesapeake, VA - $1,499,900

Residential, Detached
  • 6 Beds
  • 8 Baths
  • 6,422 SQFT
  • 19 DOM
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Grand Plantation Style Home With All The Amenities! Lake Front Custom Built Home W/a Man Made Beach In Sought After Neighborhood Of Emerald Forest! 6 Bdrms, 6 Full Bths, 2 Half Bths, 3 Car Attached/1 Car Detached. Entertainer’s Dream Home: Kitchen...



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: 1,111
Average Price: $353,566
Highest Price: $2,199,000
Lowest Price: $25,990

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