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
Curlew Ct1343$548,5452,645 Sq.Ft.3/7/2023Curling Ct1543$734,3572,845 Sq.Ft.9/16/2024Currie Ave1211$158,500392 Sq.Ft.12/20/2022Currituck Dr6142$518,7322,213 Sq.Ft.6/25/2024Curtis Saunders Ct13N/AN/AN/A55,609 Sq.Ft.7/1/2024Custis Ave1031$281,0001,191 Sq.Ft.2/27/2025Cuthrell Ln1132$342,9091,583 Sq.Ft.3/6/2020Cutspring Rd1942$518,1252,218 Sq.Ft.10/25/2024Cutspring Trce442$517,7502,147 Sq.Ft.6/4/2021Cutter Ct453$316,0001,962 Sq.Ft.12/4/2018Cypress Mill Ct454$1,087,0004,572 Sq.Ft.8/3/2021Cypress Mill Rd1354$890,9094,082 Sq.Ft.10/8/2020Cypress Pl5132$365,8331,515 Sq.Ft.4/7/2025Cypress Wood Cv443$428,2502,290 Sq.Ft.4/30/2019Cyprine Cv643$540,4002,682 Sq.Ft.12/19/2020Daffodil Ln1N/AN/AN/A743,121 Sq.Ft.N/ADaggerboard Dr1243$369,2732,133 Sq.Ft.4/22/2025Dahoon Ct842$449,4291,961 Sq.Ft.3/11/2025Dale St1231$366,4171,003 Sq.Ft.8/3/2016Dalmore Ct542$385,2502,184 Sq.Ft.2/22/2018Dalton Ct643$638,1672,484 Sq.Ft.6/13/2018Damsel Ct543$511,7502,106 Sq.Ft.8/10/2023Damyien Arch8032$270,8381,315 Sq.Ft.2/3/2025Dana Dr4332$342,5951,400 Sq.Ft.4/23/2025Danali Ct653$565,2002,605 Sq.Ft.7/25/2022Dandridge Way1N/AN/AN/A42,397 Sq.Ft.N/ADane St1232$343,7501,551 Sq.Ft.4/29/2024Danielle Ct2743$563,1202,804 Sq.Ft.10/2/2023Daniel Way1053$614,7782,943 Sq.Ft.10/3/2023Dapple Grey Ct843$893,0003,457 Sq.Ft.7/24/2017Darby Run Dr1053$861,6003,455 Sq.Ft.7/14/2021Darden St25032$461,9801,698 Sq.Ft.4/21/2025Darius Ct1632$330,0631,651 Sq.Ft.4/30/2025Darlene Ct554$736,5003,375 Sq.Ft.4/4/2019Darley Ln232$274,0001,369 Sq.Ft.11/7/2023Dartmoor Ct1222$207,4171,211 Sq.Ft.2/26/2025Daverlin Way1053$593,9002,984 Sq.Ft.9/9/2022David Ct754$316,5712,232 Sq.Ft.N/ADavids Mill Dr2442$495,2862,274 Sq.Ft.12/8/2022Davidson Cir1933$356,7061,824 Sq.Ft.7/10/2024Davis Ave4032$400,3331,824 Sq.Ft.5/8/2025Dawnee Brook Trl3843$418,1051,768 Sq.Ft.3/24/2025Dawson Cir3443$641,2502,714 Sq.Ft.1/28/2025Daylily Dr2323$248,6821,257 Sq.Ft.3/20/2025Daystone Arch1453$585,5003,413 Sq.Ft.6/27/2024Daytona Dr543$413,2002,189 Sq.Ft.11/6/2014Deal Dr942$399,37515,840 Sq.Ft.10/24/2022Deal Island Ct1332$305,3851,402 Sq.Ft.1/15/2024Deans Ct1243$522,3002,794 Sq.Ft.9/22/2022Deaton Ct632$304,1671,164 Sq.Ft.5/18/2023Deaton Dr832$300,0001,344 Sq.Ft.12/19/2024Debaun Ave7N/AN/AN/A17,302 Sq.Ft.8/15/2018Debaun Loop3N/AN/AN/A4,923 Sq.Ft.11/6/2020Debbs Ln8042$394,5601,679 Sq.Ft.5/9/2025Deborah Ct1N/AN/AN/A142,320 Sq.Ft.8/29/2024Debreck Way553$567,3332,640 Sq.Ft.1/22/2018Decatur St9732$274,5651,573 Sq.Ft.5/21/2025Deep Branch Way1133$253,5451,520 Sq.Ft.6/12/2023Deep Creek Blvd25332$314,5082,353 Sq.Ft.1/21/2025Deep Creek Cmn1623$251,0001,523 Sq.Ft.2/13/2025Deep Creek Run1333$253,8461,520 Sq.Ft.8/6/2024Deep Run Dr2043$558,7892,639 Sq.Ft.5/28/2024Deepspring Dr543$509,8002,889 Sq.Ft.7/31/2019Deepwater Dr1943$524,4712,257 Sq.Ft.5/30/2025Deerbrook Ct632$418,8331,637 Sq.Ft.1/17/2025Deerfield Cres6842$420,0772,022 Sq.Ft.2/12/2025Deerfield Ct343$445,3332,158 Sq.Ft.12/9/2015Deer Neck Arch543$540,2502,737 Sq.Ft.7/12/2023Deerneck Arch1N/AN/AN/AN/AN/ADeer Neck Dr943$542,4442,750 Sq.Ft.12/5/2023Deer Path643$488,5002,274 Sq.Ft.7/28/2014Deer Ridge Ct1642$523,7002,057 Sq.Ft.6/22/2023Deer Trl743$480,0002,721 Sq.Ft.1/15/2021Deerview Ct443$525,7502,566 Sq.Ft.9/4/2018Deerwood Ct643$454,5002,092 Sq.Ft.8/15/2024Deerwood Dr543$458,6002,020 Sq.Ft.7/23/2020Deer Xing943$462,1251,915 Sq.Ft.6/9/2022Defiance Dr3933$397,0561,890 Sq.Ft.5/29/2025Delancey St1033$380,6001,753 Sq.Ft.10/20/2021Deland Ct343$588,5002,477 Sq.Ft.4/29/2019Delaura Ct344$781,6673,633 Sq.Ft.11/15/2023Delegate Ln653$594,1672,614 Sq.Ft.3/13/2024Delia Dr1243$651,7502,631 Sq.Ft.4/27/2022Delta Ct343$424,0002,558 Sq.Ft.9/28/2022Delwood Rd3932$324,8921,596 Sq.Ft.12/17/2024Dena St732$297,8571,319 Sq.Ft.6/20/2024Denham Arch6953$688,0613,263 Sq.Ft.5/9/2025Denise Ct754$684,0003,319 Sq.Ft.5/3/2022Denning Ln1632$353,8671,723 Sq.Ft.5/14/2025Dent Pl643$415,6002,752 Sq.Ft.8/1/2006Denver Ave5142$430,7141,746 Sq.Ft.11/20/2023Derby Ct553$753,8003,604 Sq.Ft.7/12/2022Dermott St1732$320,4381,389 Sq.Ft.12/11/2024Derry Dr3132$438,1001,823 Sq.Ft.7/11/2024Desertmartin Way732$426,1671,733 Sq.Ft.9/9/2024Destiny Way1642$445,0831,750 Sq.Ft.5/16/2025Devon Dr3643$640,2943,296 Sq.Ft.2/27/2025Devonwood Cmn2332$251,7391,129 Sq.Ft.12/11/2024Dewald Rd1932$513,7892,020 Sq.Ft.12/4/2024Dewberry Dr1543$468,0712,430 Sq.Ft.2/28/20241359 E Eva BlvdChesapeake, VA 23320
Estimated Value $367,000
Living Area 1,844 SqFt
Beds 4
Baths 2.5
Year Built 2000
Property Type Single Family
Ownership Type Related
APN 0272007000090
Neighborhood Rivercrest
School District Chesapeake City Public Schools
963 Railroad AveChesapeake, VA 23324
Estimated Value $336,000
Living Area 1,911 SqFt
Beds 3
Baths 2.5
Year Built 2016
Property Type Single Family
Ownership Type Related
APN 1600000000750
Neighborhood South Norfolk
School District Chesapeake City Public Schools
824 Hardwood DrChesapeake, VA 23320
Estimated Value $452,000
Living Area 2,253 SqFt
Beds 4
Baths 2.5
Year Built 1990
Property Type Single Family
Ownership Type Related
APN 0369001000430
Neighborhood Rivercrest
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
1100 Railroad AveChesapeake, VA 23324
Estimated Value $328,000
Living Area 1,931 SqFt
Beds 3
Baths 2.5
Year Built 2003
Property Type Single Family
Ownership Type Individual
APN 1590000004042
Neighborhood South Norfolk
School District Chesapeake City Public Schools
4126 4th StChesapeake, VA 23324
Estimated Value $267,000
Living Area 1,586 SqFt
Beds 2
Baths 1.5
Year Built 1946
Property Type Single Family
Ownership Type Individual
APN 1600000000250
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
308 Esplanade PlChesapeake, VA 23320
Estimated Value $356,000
Living Area 1,849 SqFt
Beds 3
Baths 2.5
Year Built 1994
Property Type Townhouse
Ownership Type Multiple
APN 0367008000200
Neighborhood Rivercrest
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
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
954 Railroad AveChesapeake, VA 23324
Estimated Value $319,000
Living Area 1,888 SqFt
Beds 4
Baths 2.5
Year Built 2009
Property Type Single Family
Ownership Type Related
APN 1600000000940
Neighborhood South Norfolk
School District Chesapeake City Public Schools
500 Plainfield AveChesapeake, VA 23320
Estimated Value $279,000
Living Area 1,274 SqFt
Beds 3
Baths 1
Year Built 1940
Property Type Single Family
Ownership Type Individual
APN 0360000001170
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1855 Doubloon WayChesapeake, VA 23323
Estimated Value $407,000
Living Area 1,875 SqFt
Beds 3
Baths 2.5
Year Built 2018
Property Type Condominium
Ownership Type Related
APN 0354003001450
Neighborhood Deep Creek
School District Chesapeake City Public Schools
504 Rosewood TerChesapeake, VA 23320
Estimated Value $412,000
Living Area 1,629 SqFt
Beds 3
Baths 1.5
Year Built 1966
Property Type Single Family
Ownership Type Related
APN 0361008000890
Neighborhood Rivercrest
School District Chesapeake City Public Schools
3312 Country CirChesapeake, VA 23324
Estimated Value $390,000
Living Area 1,948 SqFt
Beds 4
Baths 2.5
Year Built 2004
Property Type Single Family
Ownership Type Individual
APN 1521002000090
Neighborhood South Norfolk
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