Chesapeake, Virginia is home to just over ¼ of a million residents, and is part of the vibrant Hampton Roads metropolitan area. Its proximity to major military installations, such as Naval Station Norfolk, is a big contributor to its stable economy. The presence of these military facilities stimulates the demand for housing from military personnel and civilian employees, making the city's real estate market consistent and resilient.
Neighborhoods like Great Bridge, Deep Creek, and Riverwalk cater to a variety of preferences and lifestyles, offering tremendous opportunity for real estate investors to tap into different segments of the market. Whether it's waterfront properties along the Intracoastal Waterway, suburban developments or rural acreages, the city's varied housing options are attractive to a range of potential buyers and renters.
Chesapeake’s commitment to urban development, like Scenic Heights and infrastructure projects such as the Triple Decker Bridge Rehabilitation, enhances its real estate potential. Ongoing initiatives to enhance public spaces and attract commercial developments contribute to the overall desirability of this gorgeous city as a place to both live and work. And, as it continues to grow, real estate investors may find opportunities for both short-term and long-term gains in a market that combines economic stability with a high quality of life.
Popular Streets in Chesapeake, Virginia
Bainbridge Blvd34332$293,53812,071 Sq.Ft.5/12/2025Ballahack Rd38032$613,4132,330 Sq.Ft.5/30/2025Battlefield Blvd59432$453,4517,617 Sq.Ft.5/30/2025Benefit Rd29132$596,4632,690 Sq.Ft.6/3/2025Cedar Rd33832$407,9246,596 Sq.Ft.5/13/2025Centerville Tpke31432$525,9683,538 Sq.Ft.5/27/2025George Washington Hwy31132$364,0383,864 Sq.Ft.5/30/2025Johnstown Rd31232$474,6132,460 Sq.Ft.4/25/2025Lake Cir30532$293,4601,462 Sq.Ft.5/29/2025Military Hwy44732$335,74311,197 Sq.Ft.5/30/2025All Streets in Chesapeake, Virginia
Marlow Ct843$526,8752,245 Sq.Ft.11/18/2022Marquis Ct343$510,0002,662 Sq.Ft.4/1/2023Marsh Island Dr2543$645,2273,371 Sq.Ft.11/12/2024Marsh Quay943$634,2503,371 Sq.Ft.6/17/2017Marshwood Ct1432$290,7861,246 Sq.Ft.7/11/2022Marsh Wren Ct822$290,8751,234 Sq.Ft.11/22/2021Marston Dr4542$514,2052,078 Sq.Ft.5/19/2025Marta Ln1743$479,4292,553 Sq.Ft.4/30/2024Martha Dr1632$290,2671,366 Sq.Ft.12/6/2022Martin Ave10932$299,4611,591 Sq.Ft.5/7/2025Martin Johnson Rd8232$481,9232,226 Sq.Ft.3/31/2025Martins Point Way3254$916,4403,391 Sq.Ft.5/16/2025Mary Ann Ct831$315,1251,377 Sq.Ft.11/25/2020Mary Ellen Ave1331$271,0001,324 Sq.Ft.6/7/2024Mary Lou Ln733$468,8572,283 Sq.Ft.4/29/2025Maryview Ave2132$273,8501,447 Sq.Ft.5/16/2025Mason Ct633$402,7502,225 Sq.Ft.5/5/2020Masters Ct954$989,7145,056 Sq.Ft.5/23/2018Masters Row4054$905,5384,300 Sq.Ft.6/5/2024Mast Head Way243$370,5002,191 Sq.Ft.11/23/2021Matheson Cir553$665,0002,792 Sq.Ft.3/4/2024Mathews Ct1043$453,3332,229 Sq.Ft.1/10/2020Mathews Dr1642$453,0632,084 Sq.Ft.12/19/2017Matilda Ct443$672,6672,694 Sq.Ft.4/27/2021Matt Chase542$410,3332,082 Sq.Ft.8/16/2022Mattox Dr3631$262,0001,098 Sq.Ft.4/22/2025Matty Trce353$763,0003,543 Sq.Ft.6/26/2017Maude St443$488,6672,486 Sq.Ft.9/14/2023Maulden St321N/A768 Sq.Ft.7/16/2018Maxim Ct653$572,5003,406 Sq.Ft.5/28/2021Maxwell St1542$423,0002,243 Sq.Ft.11/26/2024Mayapple Ct942$438,3752,170 Sq.Ft.5/22/2023Maycox Ln653$742,0003,148 Sq.Ft.5/2/2024Mayfair Ct342$452,5001,911 Sq.Ft.11/19/2021Mayfield Ave1021$256,7001,085 Sq.Ft.5/14/2025Mayon Dr6931$258,2791,097 Sq.Ft.3/25/2025Mayor Ward Way1N/AN/AN/AN/AN/AMaysiett St1031$156,500964 Sq.Ft.7/14/2023Maywood St2542$331,7921,669 Sq.Ft.5/7/2025Mccaan Quay1153$714,7143,998 Sq.Ft.10/15/2020Mccloud Rd16N/AN/AN/A19,386 Sq.Ft.3/26/2025Mccosh Ct332$350,0001,530 Sq.Ft.8/22/2002Mccosh Dr8932$345,8751,534 Sq.Ft.1/31/2025Mccoy Rd1044$758,7002,622 Sq.Ft.1/10/2025Mcdaniels Ave142$405,0001,932 Sq.Ft.5/1/2019Mcdunn St1N/AN/A$514,000N/A2/28/2020Mckenna Close1054$716,7783,839 Sq.Ft.8/16/2021Mckinley Ave2832$268,3461,429 Sq.Ft.5/16/2025Mckinzie Ct454$731,6673,648 Sq.Ft.11/20/2023Mclain St1732$293,7062,015 Sq.Ft.2/23/2024Mcneal Ave2542$377,3041,807 Sq.Ft.2/9/2024Mcrae Close644$680,5003,681 Sq.Ft.6/17/2022Mcrowland Ln453$701,0003,181 Sq.Ft.3/13/2025Mcrowland Way1243$720,1823,337 Sq.Ft.5/1/2025Mcsherry Ct1732$363,7331,485 Sq.Ft.4/14/2025Meadowbrook Ln3543$478,1432,544 Sq.Ft.5/15/2025Meadow Creek Ct432$370,2501,644 Sq.Ft.4/21/2023Meadow Creek Dr2432$360,5651,687 Sq.Ft.8/19/2022Meadow Ct432$416,2501,710 Sq.Ft.10/16/2006Meadow Dr6932$390,2841,747 Sq.Ft.3/3/2025Meadow Forest Ct532$363,0001,556 Sq.Ft.10/22/2007Meadow Forest Rd843$399,8751,964 Sq.Ft.8/25/2023Meadowgate Ct1042$417,8891,955 Sq.Ft.4/16/2021Meadowgreen Ct643$546,0002,579 Sq.Ft.6/24/2019Meadowhill Ct1543$527,0002,670 Sq.Ft.8/22/2024Meadowlark Ln1143$930,0003,644 Sq.Ft.12/29/2023Meadowridge Dr1332$399,5832,079 Sq.Ft.1/17/2025Meadows Lndg17222$246,4171,265 Sq.Ft.3/7/2025Meadows Way1N/AN/AN/A42,666 Sq.Ft.9/19/2011Meadow Trail Rd842$518,7501,937 Sq.Ft.9/29/2016Meadowview Rd1642$454,9382,190 Sq.Ft.7/16/2024Meadow Wood Ct1243$467,4552,684 Sq.Ft.8/16/2024Meadow Wood Dr9532$410,4352,061 Sq.Ft.4/22/2025Meads Ct10N/AN/AN/A7,340 Sq.Ft.11/4/2024Meaford St8N/AN/A$228,857100 Sq.Ft.N/AMeander Way1733$355,6001,855 Sq.Ft.7/31/2024Meanley Dr2943$539,6922,383 Sq.Ft.3/1/2025Medical Pkwy12N/A1$245,00019,569 Sq.Ft.11/22/2019Meggett Dr1643$684,0003,095 Sq.Ft.9/13/2024Meherrin River Ct1822$229,6671,077 Sq.Ft.6/2/2025Meiggs Rd3732$372,1891,742 Sq.Ft.5/14/2025Melonie Ct1442$455,9291,700 Sq.Ft.10/22/2021Melonie Dr2842$505,6302,172 Sq.Ft.6/21/2024Melton St1732$267,9331,312 Sq.Ft.12/11/2024Menands Dr2131$266,2381,142 Sq.Ft.5/15/2025Mendel Ct442$333,0001,832 Sq.Ft.1/12/2023Merano Ln2843$617,3202,610 Sq.Ft.12/10/2024Mercantile St543$498,6672,242 Sq.Ft.8/19/2021Mercer Ct342$549,3332,294 Sq.Ft.8/7/2021Merchantile St4N/AN/AN/AN/AN/AMerchants Way3N/AN/AN/A70,598 Sq.Ft.6/9/2016Meredith Dr553$673,0003,166 Sq.Ft.9/26/2024Merganser Ct9N/AN/AN/AN/AN/AMeridian Dr2043$565,5262,641 Sq.Ft.5/3/2021Merle Ct943$497,8892,213 Sq.Ft.7/7/2022Merlin Ct1132$328,9091,806 Sq.Ft.7/6/2020Merrimac Ct1043$423,0002,168 Sq.Ft.5/22/2023Merry Cat Ct443$690,3333,353 Sq.Ft.5/15/2024Meta Pointe Ct443$431,0002,184 Sq.Ft.6/13/2022Meta Pointe Dr1942$435,3332,122 Sq.Ft.9/12/20231235 Woods WayChesapeake, VA 23323
Estimated Value $366,000
Living Area 1,875 SqFt
Beds 3
Baths 2.5
Year Built 1999
Property Type Single Family
Ownership Type Related
APN 0343023001190
Neighborhood Deep Creek
School District Chesapeake City Public Schools
1972 Millville RdChesapeake, VA 23323
Estimated Value $624,000
Living Area 2,586 SqFt
Beds 4
Baths 3
Year Built 2007
Property Type Single Family
Ownership Type Related
APN 0344001000040
Neighborhood Deep Creek
School District Chesapeake City Public Schools
800 Rivanna River ReachChesapeake, VA 23320
Estimated Value $293,000
Living Area 1,434 SqFt
Beds 2
Baths 1.5
Year Built 1989
Property Type Condominium
Ownership Type Individual
APN 0367003000140
Neighborhood Rivercrest
School District Chesapeake City Public Schools
4119 Wake AveChesapeake, VA 23324
Estimated Value $282,000
Living Area 1,363 SqFt
Beds 3
Baths 2
Year Built 1965
Property Type Single Family
Ownership Type Individual
APN 1601001000670
Neighborhood South Norfolk
School District Chesapeake City Public Schools
428 Cobblewood ArchChesapeake, VA 23320
Estimated Value $255,000
Living Area 1,046 SqFt
Beds 3
Baths 2
Year Built 1987
Property Type Single Family
Ownership Type Individual
APN 0366006000230
Neighborhood Rivercrest
School District Chesapeake City Public Schools
305 Creek LnChesapeake, VA 23320
Estimated Value $536,000
Living Area 2,952 SqFt
Beds 4
Baths 2.5
Year Built 1989
Property Type Single Family
Ownership Type Related
APN 0369004000230
Neighborhood Rivercrest
School District Chesapeake City Public Schools
604 Pine BndChesapeake, VA 23320
Estimated Value $254,000
Living Area 1,273 SqFt
Beds 3
Baths 2.5
Year Built 1979
Property Type Townhouse
Ownership Type Individual
APN 0366001000280
Neighborhood Rivercrest
School District Chesapeake City Public Schools
113 Ford StChesapeake, VA 23323
Estimated Value $246,000
Living Area 1,040 SqFt
Beds 3
Baths 2
Year Built 2001
Property Type Single Family
Ownership Type Related
APN 0261002000700
Neighborhood Deep Creek
School District Chesapeake City Public Schools
1733 Faulk StChesapeake, VA 23323
Estimated Value $377,000
Living Area 2,264 SqFt
Beds 5
Baths 3
Year Built 2017
Property Type Single Family
Ownership Type Individual
APN 0261002000190
Neighborhood Deep Creek
School District Chesapeake City Public Schools
1333 Winslow AveChesapeake, VA 23323
Estimated Value $329,000
Living Area 1,500 SqFt
Beds 4
Baths 2
Year Built 1977
Property Type Single Family
Ownership Type Individual
APN 0255002000130
Neighborhood Deep Creek
School District Chesapeake City Public Schools
320 Esplanade PlChesapeake, VA 23320
Estimated Value $311,000
Living Area 1,352 SqFt
Beds 2
Baths 2.5
Year Built 1993
Property Type Townhouse
Ownership Type Related
APN 0367008000150
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1824 Warfield StChesapeake, VA 23324
Estimated Value $282,000
Living Area 1,476 SqFt
Beds 3
Baths 2.5
Year Built 2006
Property Type Single Family
Ownership Type Related
APN 1600000002671
Neighborhood South Norfolk
School District Chesapeake City Public Schools
2001 Coral AveChesapeake, VA 23324
Estimated Value $306,000
Living Area 2,328 SqFt
Beds 3
Baths 1
Year Built 1964
Property Type Single Family
Ownership Type Individual
APN 1600000003270
Neighborhood South Norfolk
School District Chesapeake City Public Schools
4116 Reid StChesapeake, VA 23324
Estimated Value $292,000
Living Area 1,404 SqFt
Beds 3
Baths 2.5
Year Built 2005
Property Type Single Family
Ownership Type Related
APN 1600000001651
Neighborhood South Norfolk
School District Chesapeake City Public Schools
705 Montrose CtChesapeake, VA 23320
Estimated Value $288,000
Living Area 1,516 SqFt
Beds 3
Baths 2.5
Year Built 1991
Property Type Townhouse
Ownership Type Individual
APN 0367002001510
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1008 Roxbury CtChesapeake, VA 23320
Estimated Value $468,000
Living Area 2,658 SqFt
Beds 4
Baths 3.5
Year Built 2007
Property Type Single Family
Ownership Type Individual
APN 0361015000260
Neighborhood Rivercrest
School District Chesapeake City Public Schools