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Homes For Sale in Chesapeake, VA

homes for sale in chesapeake VAIf you’re looking at homes for sale in Chesapeake, VA then you’re in for a treat. As an independent city in Norfolk County, Chesapeake came into existence in 1963. That being said, the area has a rich history that dates back to the mid 1600s.

The town is the second largest in Virginia in terms of land mass, which makes it home to a number of activities and attractions to draw you into its charms. Once you have the chance to browse through the town, you will see why so many people love to live here and call it home.

Read more to learn about events and attractions in Chesapeake, or browse the real estate listings below.

View Current Chesapeake Listings

All Listings Under $100,000 $100,000 - $200,000
$200,000 - $300,000 $300,000 - $400,000 $400,000 - $500,000
$500,000 - $600,000 $600,000 - $700,000 $700,000 - $800,000
$800,000 - $900,000 $900,000 - $1,000,000 Over $1,000,000
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3812 Bruce Rd, Chesapeake, VA - $2,500,000

Residential, Detached
  • 7 Beds
  • 7 Baths
  • 9,713 SQFT
  • 62 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...

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

Residential, Detached
  • 5 Beds
  • 6 Baths
  • 7,102 SQFT
  • 112 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...

717 School House Rd, Chesapeake, VA - $1,500,000

Residential, Detached
  • 4 Beds
  • 4 Baths
  • 4,425 SQFT
  • 97 DOM
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One Of A Kind Estate! Beautiful Custom Built 4 Bedroom 3.5 Bath Colonial Home Takes You Back In Time. Imagine The Possibilities Of This Gem Sitting On 3 Acres With An Additional 18.5 Acres Adjoining The Property. The Large Front Porch With Clas...

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

Residential, Detached
  • 6 Beds
  • 7 Baths
  • 7,600 SQFT
  • 430 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...

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

Residential, Detached
  • 5 Beds
  • 6 Baths
  • 6,329 SQFT
  • 92 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, ...

1331 Simon Dr, Chesapeake, VA - $999,900

Residential, Detached
  • 7 Beds
  • 7 Baths
  • 7,270 SQFT
  • 78 DOM
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Location, Location, Peace Of Mind And Central Location!!! This Stunning Home Comes With All The Bells And Whistles For Luxury Living At Its Finest That You Can't Find Anywhere Else For This Price. From The Gourmet Kitchen's Subzero Refrigerator/...

350 Scone Castle Loop, Chesapeake, VA - $995,000

Residential, Detached
  • 7 Beds
  • 8 Baths
  • 6,000 SQFT
  • 163 DOM
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Incredible Is The Only Way To Describe This Former Homerama Home In Hickory School District. With A Detached In-law Suite/guest House And The First Floor Master, It Is Fit For Multi-generational Living. All 6 Bedrooms In The Main House Have Dedi...

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

Residential, Detached
  • 5 Beds
  • 7 Baths
  • 6,173 SQFT
  • 77 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...

521 Woodards Ford Rd, Chesapeake, VA - $975,000

Residential, Detached
  • 6 Beds
  • 5 Baths
  • 7,261 SQFT
  • 28 DOM
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One Of A Kind 7300sf Home. Sitting On 3 Private Acres With Sought After Hickory Schools. Priced Below Tax Assessment. Main House Has 6 Bedrooms, 3 Full & 2 Half Baths. 4 Car Detached Garage Has 2 Apartments With Their Own Entrance. The Kitchen And...

314 Cawdor Xing, Chesapeake, VA - $949,000

Residential, Detached
  • 5 Beds
  • 4 Baths
  • 4,040 SQFT
  • 93 DOM
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“stunning” Describes This Homerama Home In The Hickory School District. On A Premium Water Lot With A Lighted Fountain And Loaded With Upgrades, This Semi-custom Home Is One Of A Kind. Automated Control 4 System Operates Security System, Outdoor L...

2830 Battlefield Blvd S, Chesapeake, VA - $949,000

Residential, Detached
  • 5 Beds
  • 5 Baths
  • 4,729 SQFT
  • 417 DOM
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Listed 25k Below Recent Appraisal! Looking For A Private Estate In The Country, But Proximate To City Living? This Is It. Call Agent To See This One-of-a-kind Property. New Carpet And Paint! Custom Built Brick Home 5br 5ba 4967 Sq Ft On 25.71 Acr...

177 Greengable Way, Chesapeake, VA - $900,000

Residential, Detached
  • 6 Beds
  • 5 Baths
  • 5,050 SQFT
  • 84 DOM
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Welcome Home To This Beautiful Authentic, Custom Built Home With Upgrades Galore And Filled With Rich Textures And Elegant Finishes! This Well Crafted, Transitional Home Boasts Over 5,000 Square Feet Of Exquisitely Designed Living Space. It Feat...

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Chesapeake Homes For Sale

Chesapeake homes for sale reflect the blend of historical styles in the area and include waterfront homes, traditional estates, and modern cottages. It’s not uncommon to see two-story homes with tall gabled roofs and sprawling front porches.

Recently ranked the 21st city to live in by Bloomberg Businessweek, this city is home to a population of warm, friendly, and diverse residents.

Living in Chesapeake Homes

There’s a wealth of events and attractions near Chesapeake homes. In addition to the many shopping, cultural and sightseeing opportunities in the city, you'll find that the area is also a great place for outdoor activities such as bird watching, golf, fishing, biking, hiking, kayaking and more!

One of our local favorites is a regular haunt on a hot summer day. Head over to Bergey's Breadbasket and enjoy some of the best ice cream around town. Regardless of how many times you go here, you will always find something new and exciting to tantalize your tastebuds and leave you wanting more.

Bergey's Breadbasket also features a farm with fresh produce and flowers, along with a sensational bakery - bring home fresh baked bread or a homemade pie for the whole family to enjoy.

Browse Chesapeake Neighborhoods

Start your home search today. Contact the PerfectHouse Team to start looking at Chesapeake real estate.

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Chesapeake

What's My Home Worth?

Overview

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: 2,067
Average Price: $338,222
Highest Price: $2,500,000
Lowest Price: $40,000