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
Enterprise Cir4N/AN/AN/A24,406 Sq.Ft.4/21/2022Enterprise Ct3N/A1N/A15,442 Sq.Ft.7/31/2018Enviva Way1N/AN/AN/A28,253 Sq.Ft.1/19/2011Epping Ct542$491,8002,365 Sq.Ft.8/20/2019Equestrian Trl2N/AN/AN/AN/AN/AEquinox Lndg942$513,4442,187 Sq.Ft.7/8/2022Eric Ct5232$186,8241,127 Sq.Ft.1/13/2025Erie St4932$408,5101,759 Sq.Ft.5/9/2025Erik Paul Dr2942$482,9632,083 Sq.Ft.12/4/2024Erin Ln2242$495,3332,222 Sq.Ft.9/16/2024Ervin Ct343$563,5002,503 Sq.Ft.10/14/2021Esmont Ct642$548,5002,539 Sq.Ft.8/12/2024Esplanade Pl8733$360,3981,841 Sq.Ft.5/29/2025Essex Dr1532$392,6671,822 Sq.Ft.12/16/2024Estates Way2933$344,7081,974 Sq.Ft.5/17/2024Estella Dr622$295,0001,210 Sq.Ft.9/16/2021Estella Way2233$298,0001,405 Sq.Ft.3/14/2025Esterview Ln943$588,6672,497 Sq.Ft.4/25/2025Estes Rd643$683,2002,751 Sq.Ft.3/1/2023Estol St5N/AN/A$388,000N/A5/24/2007Estuary Ct953$674,8892,748 Sq.Ft.12/12/2024Ethel James Dr953$573,6253,539 Sq.Ft.9/1/2023Etheridge Ct532$474,6001,881 Sq.Ft.9/24/2017Etheridge Manor Blvd7N/AN/AN/AN/AN/AEtheridge Rd9842$488,8211,986 Sq.Ft.6/30/2024Eugenia Ave332$269,000951 Sq.Ft.4/17/2020Eunice Way343$608,0001,064 Sq.Ft.1/29/2008Eustis Ave1032$308,6001,361 Sq.Ft.11/22/2024Eva Blvd8632$337,7241,729 Sq.Ft.8/19/2024Eva Ct532$335,5001,494 Sq.Ft.12/2/2016Evans Ln454$1,237,0004,282 Sq.Ft.7/26/2018Evelyn Way2743$637,8822,580 Sq.Ft.2/22/2023Everett St4432$297,5911,557 Sq.Ft.4/15/2025Evergreen Ct1443$503,2142,693 Sq.Ft.11/10/2021Evers Ct1932$172,7221,469 Sq.Ft.9/16/2024Evick Way743$401,4292,013 Sq.Ft.9/13/2023Ewell Ln2842$403,7411,764 Sq.Ft.3/4/2024Excalibur Ct1742$370,9332,090 Sq.Ft.9/15/2022Excalibur St1832$347,3131,795 Sq.Ft.6/30/2023Executive Blvd841N/AN/A8,087 Sq.Ft.4/15/2025Executive Center Dr1N/AN/AN/A107,017 Sq.Ft.8/15/2012Executive Ct7N/AN/AN/A10,120 Sq.Ft.7/8/2022Exeter Cir1032$266,2001,418 Sq.Ft.4/28/2023Expressway6N/AN/A$384,000N/A10/23/2018Faire Chase8422$296,1671,353 Sq.Ft.4/7/2025Fairfax Ter2232$279,6361,513 Sq.Ft.5/1/2025Fairfield Dr4642$468,4882,019 Sq.Ft.5/10/2025Fairhaven Rd7543$532,6622,372 Sq.Ft.8/22/2024Fair Oak Dr3043$635,3792,885 Sq.Ft.3/26/2025Fairview St1N/AN/AN/A366,720 Sq.Ft.N/AFairway Ct943$589,4442,970 Sq.Ft.9/20/2023Fairway Dr12443$591,5792,859 Sq.Ft.4/24/2025Fairways Lookout2222$304,0001,374 Sq.Ft.4/15/2025Fairways Reach3N/AN/A$306,000N/AN/AFairwind Dr1N/AN/AN/A256,041 Sq.Ft.6/15/2023Falcon Ave931$276,0004,039 Sq.Ft.5/30/2024Fallcreek Run5533$345,0381,542 Sq.Ft.2/18/2025Fallen Leaf Ln1653$638,0002,688 Sq.Ft.7/25/2022Fallhaven Ct943$479,0002,158 Sq.Ft.1/30/2023Fall Ridge Ct843$619,6252,747 Sq.Ft.2/27/2020Fall Ridge Ln1643$626,9332,767 Sq.Ft.4/8/2022Falls Brook Run2054$1,229,7224,622 Sq.Ft.2/19/2025Falls Creek Ct1053$670,8753,161 Sq.Ft.9/20/2023Falls Creek Dr3853$783,3243,422 Sq.Ft.4/17/2024Falmouth Ct543$466,4002,161 Sq.Ft.5/18/2018Falmouth Dr2943$610,7243,097 Sq.Ft.11/29/2022False Creek Way1053$619,0003,183 Sq.Ft.7/25/2022Farange Dr543$546,4002,449 Sq.Ft.10/26/2022Fargo Ct843$673,4293,080 Sq.Ft.11/5/2020Farington Cir1632$263,0001,461 Sq.Ft.2/27/2025Farman Ct442$470,0001,595 Sq.Ft.3/12/2020Farmer Ln4N/AN/AN/A79,104 Sq.Ft.12/20/2021Farnsworth Dr3443$593,8482,862 Sq.Ft.3/13/2025Farringdon Way5033$309,9391,850 Sq.Ft.5/30/2025Faulkner Dr833$290,2501,314 Sq.Ft.2/13/2024Faulk St1732$285,0591,550 Sq.Ft.11/15/2024Fawn Lake Ct432$404,0001,727 Sq.Ft.8/11/2023Fawnwood Cmn1032$256,9001,179 Sq.Ft.2/18/2025Faye St152N/A2,176 Sq.Ft.N/AFeatherbed Ct543$453,8003,454 Sq.Ft.11/16/2016Featherbed Dr1743$441,7063,026 Sq.Ft.5/24/2023Feldspar Quay1043$535,0002,670 Sq.Ft.4/23/2025Felton St5N/AN/AN/AN/A12/13/2024Fenton Quay2443$446,6252,076 Sq.Ft.4/18/2025Fentress Airfield Rd3942$517,1792,277 Sq.Ft.4/22/2024Fentress Loop6N/AN/AN/A170 Sq.Ft.N/AFentress Rd8332$421,0002,057 Sq.Ft.12/17/2024Fenway Ave4332$336,2228,924 Sq.Ft.5/20/2025Ferebee Ave3732$298,0561,359 Sq.Ft.4/18/2025Ferguson Cv553$543,6003,286 Sq.Ft.9/30/2015Ferguson Loop7943$727,7042,848 Sq.Ft.5/12/2025Fernbridge Pl1343$488,1672,776 Sq.Ft.10/4/2023Ferncliff Ct1443$491,4172,658 Sq.Ft.10/26/2021Ferndale Rd3932$334,0511,728 Sq.Ft.5/20/2025Fern Dr942$445,1111,769 Sq.Ft.10/16/2020Fernham Ln3242$517,5002,113 Sq.Ft.9/16/2024Fern Mill Ct653$635,8003,436 Sq.Ft.3/20/2021Fern Mill Ln953$643,0003,553 Sq.Ft.9/14/2021Fern Quay453$641,7503,106 Sq.Ft.3/11/2022Fernwood Farms Ct642$426,6671,965 Sq.Ft.5/29/2020101 Ford StChesapeake, VA 23323
Estimated Value $244,000
Living Area 1,120 SqFt
Beds 3
Baths 1
Year Built 1962
Property Type Single Family
Ownership Type Individual
APN 0261002000790
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
4374 Pickney LnChesapeake, VA 23324
Estimated Value $327,000
Living Area 1,760 SqFt
Beds 3
Baths 2.5
Year Built 2016
Property Type Condominium
Ownership Type Individual
APN 1580001001170
Neighborhood South Norfolk
School District Chesapeake City Public Schools
1818 Aft WayChesapeake, VA 23323
Estimated Value $415,000
Living Area 2,036 SqFt
Beds 3
Baths 2.5
Year Built 2021
Property Type Condominium
Ownership Type Multiple
APN 0354003001890
Neighborhood Deep Creek
School District Chesapeake City Public Schools
704 Cordgrass CtChesapeake, VA 23320
Estimated Value $455,000
Living Area 2,189 SqFt
Beds 4
Baths 2.5
Year Built 1990
Property Type Single Family
Ownership Type Individual
APN 0369001000340
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1505 Waitsel Dr #206Chesapeake, VA 23320
Estimated Value $284,000
Living Area 1,327 SqFt
Beds 2
Baths 2
Year Built 2023
Property Type Condominium
Ownership Type Individual
APN 0273016000410
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1233 Marge DrChesapeake, VA 23320
Estimated Value $302,000
Living Area 1,336 SqFt
Beds 3
Baths 1.5
Year Built 1975
Property Type Single Family
Ownership Type Individual
APN 0272001000440
Neighborhood Rivercrest
School District Chesapeake City Public Schools
621 Pine BndChesapeake, VA 23320
Estimated Value $246,000
Living Area 1,273 SqFt
Beds 3
Baths 2.5
Year Built 1979
Property Type Townhouse
Ownership Type Individual
APN 0366001000150
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
736 Huntly DrChesapeake, VA 23320
Estimated Value $251,000
Living Area 1,240 SqFt
Beds 3
Baths 1.5
Year Built 1990
Property Type Townhouse
Ownership Type Corporate
APN 0367002000640
Neighborhood Rivercrest
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
1785 Shipyard RdChesapeake, VA 23323
Estimated Value $297,000
Living Area 1,100 SqFt
Beds 2
Baths 1.5
Year Built 1961
Property Type Single Family
Ownership Type Individual
APN 0350000000030
Neighborhood Deep Creek
School District Chesapeake City Public Schools
4125 3rd StChesapeake, VA 23324
Estimated Value $218,000
Living Area 924 SqFt
Beds 2
Baths 1
Year Built 1952
Property Type Single Family
Ownership Type Individual
APN 1590000003730
Neighborhood South Norfolk
School District Chesapeake City Public Schools
2028 Warfield StChesapeake, VA 23324
Estimated Value $255,000
Living Area 1,284 SqFt
Beds 3
Baths 2
Year Built 1987
Property Type Single Family
Ownership Type Individual
APN 1600000002830
Neighborhood South Norfolk
School District Chesapeake City Public Schools
708 Bulrush CtChesapeake, VA 23320
Estimated Value $471,000
Living Area 2,189 SqFt
Beds 4
Baths 2.5
Year Built 1991
Property Type Single Family
Ownership Type Individual
APN 0369001000470
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1301 Pinecroft LnChesapeake, VA 23323
Estimated Value $341,000
Living Area 1,543 SqFt
Beds 3
Baths 2
Year Built 1999
Property Type Single Family
Ownership Type Individual
APN 0343023000470
Neighborhood Deep Creek
School District Chesapeake City Public Schools