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Chesapeake

Chesapeake is a family-friendly city known for its beautiful parks, lakes, rivers, and culturally diverse events. Recognized as one of the six best places to live by Money Magazine, Chesapeake offers the best of both worlds: urban conveniences and rural charm. Parks and Outdoor Activities Chesapeake is full of green spaces and outdoor options for all interests. Great Bridge Locks Park: Learn about the historic lock system while enjoying scenic views of boats traveling between waterways.

Elizabeth River Park: Perfect for boating, fishing, and family fun with a kids’ play area and a boat ramp.Northwest River Park: Offers fishing, boating, camping, and even horseback riding for all ages. Oak Grove Park: Features a 1.5-mile trail around a scenic lake with exercise stations for walking, biking, and workouts. If you’re relocating to Hampton Roads, Chesapeake is one of the most desirable cities to live in. It combines family-oriented communities, outdoor recreation, and a vibrant lifestyle, making it ideal for anyone looking to call the area home.

Min. Price
Max. Price
Beds
Baths
2051 Charwood Drive Chesapeake, VA 23320
$798,910
4 Beds 3 | 1 Baths 3,555 Sqft Listing No. 10639901 Property Type: House camera Virtual Tour camera (24)
Details
1124 Kilby Drive Chesapeake, VA 23320
$493,000
4 Beds 2 | 1 Baths 2,509 Sqft Listing No. 10639866 Property Type: House camera (35)
Details
800 Broad Reach Road Chesapeake, VA 23320
$505,000
3 Beds 2 | 1 Baths 2,383 Sqft Listing No. 10639881 Property Type: House
Details
328 Big Pond Lane Chesapeake, VA 23323
$450,000
4 Beds 2 | 1 Baths 2,010 Sqft Listing No. 10639867 Property Type: House
Details
1453 Whittamore Road Chesapeake, VA 23322
$719,900
5 Beds 3 Baths 2,660 Sqft Listing No. 10639822 Property Type: House camera (20)
Details
1073 Scenic Boulevard Chesapeake, VA 23322
$399,900
3 Beds 1 Baths 1,188 Sqft Listing No. 10639800 Property Type: House camera (23)
Details
2312 Dapple Grey Court Chesapeake, VA 23322
$799,000
4 Beds 3 Baths 2,800 Sqft Listing No. 10639826 Property Type: House camera (50)
Details
237 Castleberry Drive Chesapeake, VA 23322
$779,900
6 Beds 3 Baths 3,414 Sqft Listing No. 10639770 Property Type: House
Details
316 Tudor Place Chesapeake, VA 23325
$430,000
5 Beds 3 | 1 Baths 2,710 Sqft Listing No. 10639654 Property Type: House camera (3)
Details
3611 Radford Circle Chesapeake, VA 23321
$235,000
2 Beds 1 | 1 Baths 1,254 Sqft Listing No. 10639739 Property Type: House camera Virtual Tour camera (26)
Details
627 Bartell Drive Chesapeake, VA 23322
$555,000
4 Beds 2 | 1 Baths 2,400 Sqft Listing No. 10639724 Property Type: House camera (48)
Details
2156 Edwin Drive Chesapeake, VA 23322
$573,740
3 Beds 3 Baths 2,642 Sqft Listing No. 10639726 Property Type: Condo camera (25)
Details
 2051 Charwood Drive, Chesapeake, VA 23320
New Listing
camera VIRTUAL TOUR camera (24)
price

$798,910

beds

4 4 Beds

baths

3 | 1 3 | 1 Baths

lot size

3,555 Sqft 3,555 Sqft

listing no.

10639901 Listing No. 10639901

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (24)

 1124 Kilby Drive, Chesapeake, VA 23320
New Listing
camera (35)
price

$493,000

beds

4 4 Beds

baths

2 | 1 2 | 1 Baths

lot size

2,509 Sqft 2,509 Sqft

listing no.

10639866 Listing No. 10639866

property type

House Property Type: House

gallery photos

camera (35)

 800 Broad Reach Road, Chesapeake, VA 23320
Coming Soon
price

$505,000

beds

3 3 Beds

baths

2 | 1 2 | 1 Baths

lot size

2,383 Sqft 2,383 Sqft

listing no.

10639881 Listing No. 10639881

property type

House Property Type: House

 328 Big Pond Lane, Chesapeake, VA 23323
New Listing
price

$450,000

beds

4 4 Beds

baths

2 | 1 2 | 1 Baths

lot size

2,010 Sqft 2,010 Sqft

listing no.

10639867 Listing No. 10639867

property type

House Property Type: House

 1453 Whittamore Road, Chesapeake, VA 23322
New Listing
camera (20)
price

$719,900

beds

5 5 Beds

baths

3 3 Baths

lot size

2,660 Sqft 2,660 Sqft

listing no.

10639822 Listing No. 10639822

property type

House Property Type: House

gallery photos

camera (20)

 1073 Scenic Boulevard, Chesapeake, VA 23322
New Listing
camera (23)
price

$399,900

beds

3 3 Beds

baths

1 1 Baths

lot size

1,188 Sqft 1,188 Sqft

listing no.

10639800 Listing No. 10639800

property type

House Property Type: House

gallery photos

camera (23)

 2312 Dapple Grey Court, Chesapeake, VA 23322
New Listing
camera (50)
price

$799,000

beds

4 4 Beds

baths

3 3 Baths

lot size

2,800 Sqft 2,800 Sqft

listing no.

10639826 Listing No. 10639826

property type

House Property Type: House

gallery photos

camera (50)

 237 Castleberry Drive, Chesapeake, VA 23322
Coming Soon
price

$779,900

beds

6 6 Beds

baths

3 3 Baths

lot size

3,414 Sqft 3,414 Sqft

listing no.

10639770 Listing No. 10639770

property type

House Property Type: House

 316 Tudor Place, Chesapeake, VA 23325
New Listing
camera (3)
price

$430,000

beds

5 5 Beds

baths

3 | 1 3 | 1 Baths

lot size

2,710 Sqft 2,710 Sqft

listing no.

10639654 Listing No. 10639654

property type

House Property Type: House

gallery photos

camera (3)

 3611 Radford Circle, Chesapeake, VA 23321
New Listing
camera VIRTUAL TOUR camera (26)
price

$235,000

beds

2 2 Beds

baths

1 | 1 1 | 1 Baths

lot size

1,254 Sqft 1,254 Sqft

listing no.

10639739 Listing No. 10639739

property type

House Property Type: House

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (26)

 627 Bartell Drive, Chesapeake, VA 23322
New Listing
camera (48)
price

$555,000

beds

4 4 Beds

baths

2 | 1 2 | 1 Baths

lot size

2,400 Sqft 2,400 Sqft

listing no.

10639724 Listing No. 10639724

property type

House Property Type: House

gallery photos

camera (48)

 2156 Edwin Drive, Chesapeake, VA 23322
New Listing
camera (25)
price

$573,740

beds

3 3 Beds

baths

3 3 Baths

lot size

2,642 Sqft 2,642 Sqft

listing no.

10639726 Listing No. 10639726

property type

Condo Property Type: Condo

gallery photos

camera (25)

The listings data displayed on this medium comes in part from the Real Estate Information Network, Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN, therefore, makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.

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This application does not include information on all of the properties available for sale at this time.

Some or all of the listings (or listings data) represented in this application have been enhanced with data not provided by REIN. The enhancements are as follows: Map (Source: Mapbox), Mortgage Calculator (Source: iHomefinder), Schools (Source: GreatSchools), and Walk Score (Source: Walk Score).

REIN updates its listings on a daily basis. Site provided by iHomefinder. Powered by iHomefinder.
REIN MLS data last updated at June 16, 2026, 10:30 AM ET
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