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
Septaria Quay743$542,0002,665 Sq.Ft.8/27/2020September Ln942$538,3752,213 Sq.Ft.7/6/2021Sequoia Pl533$421,2002,329 Sq.Ft.8/19/2024Seren Dr233$338,5001,435 Sq.Ft.11/16/2021Serf Ct1031$284,1001,150 Sq.Ft.12/16/2024Sero Ct732$357,4291,775 Sq.Ft.4/21/2017Settlement Ct1022$281,5001,765 Sq.Ft.4/22/2024Seven Eleven Rd5242$526,9782,097 Sq.Ft.11/20/2024Seville Dr1243$599,3333,044 Sq.Ft.8/31/2020Sextant St2232$296,8571,339 Sq.Ft.4/10/2025Shadowberry Crst2143$478,3162,238 Sq.Ft.5/16/2025Shadow Brooke Dr2553$672,6823,392 Sq.Ft.4/3/2025Shadowfield Ct1143$591,1822,771 Sq.Ft.4/29/2022Shadowlake Ct343$461,0002,665 Sq.Ft.7/10/2015Shadowlake Dr2343$474,1502,502 Sq.Ft.12/20/2024Shadowood Ln2742$459,7691,753 Sq.Ft.5/13/2022Shadwell Ter1243$531,7272,287 Sq.Ft.7/29/2021Shady Cove Ct1243$541,7272,522 Sq.Ft.10/7/2024Shady Ln1N/AN/AN/A80,176 Sq.Ft.12/20/2021Shadyside Ln2543$483,1202,565 Sq.Ft.4/17/2025Shady Tree Way1242$386,7271,779 Sq.Ft.9/20/2022Shannon St6N/AN/AN/A23,739 Sq.Ft.12/13/2024Sharon Dr8432$401,1201,544 Sq.Ft.4/23/2025Shasta Dr1643$707,7502,845 Sq.Ft.4/30/2024Shawnee Rd1632$392,3751,551 Sq.Ft.8/31/2023Shearwater Ct11N/AN/AN/AN/AN/ASheffield Ct1143$634,4443,285 Sq.Ft.3/15/2023Sheffield Dr1N/AN/AN/AN/AN/AShell Drake Ct14N/AN/AN/AN/AN/AShelley St932$302,1251,408 Sq.Ft.7/15/2024Shell Rd16442$349,6142,391 Sq.Ft.4/1/2025Shelter Rock Ln1053$705,0003,320 Sq.Ft.9/20/2024Shelview Cir2542$459,5201,914 Sq.Ft.11/14/2023Shenandoah Pkwy6643$630,1672,972 Sq.Ft.12/9/2024Shenandoah River Dr422$233,5001,042 Sq.Ft.5/9/2024Shenandoah River Rd1622$289,9381,370 Sq.Ft.1/15/2024Shepherds Ct942$412,6671,729 Sq.Ft.8/4/2023Shepherds Gate2333$409,8181,776 Sq.Ft.4/11/2022Sherando Ct1953$644,3893,037 Sq.Ft.4/24/2025Sherborn Trce943$536,0002,340 Sq.Ft.7/18/2022Sherbrooke Rd1132$312,8891,721 Sq.Ft.6/19/2019Sheridan Ave1N/AN/A$388,000N/AN/ASheriff Ct332$493,0001,777 Sq.Ft.5/28/2025Sherman Dr632$342,7501,646 Sq.Ft.2/27/2025Sherrard Ct653$681,0003,415 Sq.Ft.6/20/2012Sherringfield Ter1443$524,5002,290 Sq.Ft.7/21/2023Sherrington Dr3N/AN/AN/A15,460 Sq.Ft.1/26/2011Sherwood Dr743$626,1432,657 Sq.Ft.5/31/2024Sherwood Forest Rd2643$541,6192,560 Sq.Ft.1/9/2023Shetland Dr1932$441,3331,572 Sq.Ft.2/18/2025Shield Ln1142$375,5001,786 Sq.Ft.5/28/2024Shifford Ln542$451,6001,655 Sq.Ft.3/21/2025Shillelagh Rd23932$668,0842,222 Sq.Ft.1/27/2025Shipping Ln1043$688,8332,682 Sq.Ft.10/29/2021Ships Lndg242$395,5001,616 Sq.Ft.12/9/2013Ships Xing2843$478,3852,083 Sq.Ft.6/5/2025Shipton Ct1043$512,5562,581 Sq.Ft.2/21/2023Shipyard Rd15542$457,6883,310 Sq.Ft.3/28/2025Shire Ln1N/AN/AN/A42,985 Sq.Ft.7/29/2013Shoal Creek Trl19132$341,8381,658 Sq.Ft.5/2/2025Shoal Quay743$650,6003,534 Sq.Ft.11/30/2023Shoemaker Dr632$395,8332,215 Sq.Ft.8/16/2024Shorebird Ct943$427,5001,907 Sq.Ft.12/7/2023Shorebird Ln1542$431,4001,908 Sq.Ft.5/19/2025Shore Rd4032$301,4471,304 Sq.Ft.5/6/2024Shore Side Rd1432$397,2141,764 Sq.Ft.10/18/2024Shorewood Dr1732$361,8241,644 Sq.Ft.5/5/2020Shortleaf Ln4423$250,2271,258 Sq.Ft.4/30/2025Short Spoon Ct464$937,7504,705 Sq.Ft.3/3/2010Shoveller Ct9N/AN/AN/AN/AN/ASidley Ct532$382,2001,580 Sq.Ft.3/8/2005Sidley Rd1132$399,3001,714 Sq.Ft.4/6/2020Sierra Dr2532$440,7922,084 Sq.Ft.8/14/2024Sigmon Dr19N/AN/A$360,882N/A9/9/2019Signal Quay554$871,4004,163 Sq.Ft.3/3/2020Sign Pine Rd6443$676,9582,867 Sq.Ft.3/6/2025Sikeston Ln2033$428,2501,927 Sq.Ft.6/13/2024Silk Tree Ln1333$418,7502,221 Sq.Ft.1/7/2025Silver Fox Trce2153$582,3162,862 Sq.Ft.9/5/2024Silver Maple Dr1453$703,0003,464 Sq.Ft.5/15/2023Silver Queen Ln1N/AN/AN/AN/AN/ASilver Rail Ln1243$489,4002,264 Sq.Ft.10/28/2021Silverthorne Ct543$491,0002,441 Sq.Ft.2/14/2024Silverton Way2743$721,8463,089 Sq.Ft.4/11/2024Silvertown Ave1231$591,2861,640 Sq.Ft.5/14/2025Silverwood Blvd1442$418,5002,075 Sq.Ft.12/18/2024Simms Arch543$687,4003,092 Sq.Ft.6/10/2022Simon Dr6454$947,8734,088 Sq.Ft.4/22/2025Simons Ln2N/AN/A$459,000N/A2/15/2023Simpson Ln1133$509,2732,106 Sq.Ft.5/19/2023Sinclair Ln1753$774,1543,530 Sq.Ft.8/13/2020Sippel Dr3232$431,6561,842 Sq.Ft.9/5/2024Sir Francis Drake Dr3132$276,1111,403 Sq.Ft.5/27/2025Sir Galahad Dr3532$322,8181,563 Sq.Ft.2/8/2022Sir Gawaine Dr3732$315,6251,480 Sq.Ft.3/21/2025Sir Kay Ct732$337,0001,557 Sq.Ft.3/11/2024Sir Kay Dr3632$314,9351,555 Sq.Ft.11/4/2024Sir Knight Ct553$533,8002,500 Sq.Ft.11/5/2010Sir Lance Dr2132$368,6501,895 Sq.Ft.9/9/2022Sir Lancelot Ct532$333,0001,677 Sq.Ft.11/17/20231100 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
613 Consolvo PlChesapeake, VA 23324
Estimated Value $362,000
Living Area 2,120 SqFt
Beds 3
Baths 3
Year Built 2017
Property Type Condominium
Ownership Type Related
APN 1580001001730
Neighborhood South Norfolk
School District Chesapeake City Public Schools
858 Creekside CresChesapeake, VA 23320
Estimated Value $257,000
Living Area 1,348 SqFt
Beds 2
Baths 2.5
Year Built 1990
Property Type Townhouse
Ownership Type Individual
APN 0367006000220
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1649 Shipyard RdChesapeake, VA 23323
Estimated Value $421,000
Living Area 1,716 SqFt
Beds 4
Baths 2.5
Year Built 2010
Property Type Single Family
Ownership Type Individual
APN 0350000000210
Neighborhood Deep Creek
School District Chesapeake City Public Schools
1702 Willow Point ArchChesapeake, VA 23320
Estimated Value $241,000
Living Area 1,244 SqFt
Beds 2
Baths 2
Year Built 2000
Property Type Condominium
Ownership Type Related
APN 0367013000720
Neighborhood Rivercrest
School District Chesapeake City Public Schools
904 Robert Welch CtChesapeake, VA 23320
Estimated Value $574,000
Living Area 3,351 SqFt
Beds 5
Baths 3
Year Built 2006
Property Type Single Family
Ownership Type Multiple
APN 0361016000230
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1408 Portlock RdChesapeake, VA 23324
Estimated Value $290,000
Living Area 2,005 SqFt
Beds 4
Baths 2
Year Built 1936
Property Type Single Family
Ownership Type Related
APN 1590000002550
Neighborhood South Norfolk
School District Chesapeake City Public Schools
609 Tuskegee AveChesapeake, VA 23320
Estimated Value $384,000
Living Area 2,058 SqFt
Beds 3
Baths 2.5
Year Built 2002
Property Type Single Family
Ownership Type Individual
APN 0351004002130
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1648 Shipyard RdChesapeake, VA 23323
Estimated Value $1,031,000
Living Area 4,796 SqFt
Beds 5
Baths 4.5
Year Built 2013
Property Type Single Family
Ownership Type Multiple
APN 0350000000430
Neighborhood Deep Creek
School District Chesapeake City Public Schools
4309 Pickney LnChesapeake, VA 23324
Estimated Value $324,000
Living Area 1,720 SqFt
Beds 3
Baths 2.5
Year Built 2018
Property Type Condominium
Ownership Type Multiple
APN 1580001000780
Neighborhood South Norfolk
School District Chesapeake City Public Schools
312 Outlaw StChesapeake, VA 23320
Estimated Value $410,000
Living Area 2,501 SqFt
Beds 4
Baths 2.5
Year Built 2002
Property Type Single Family
Ownership Type Individual
APN 0351004001130
Neighborhood Rivercrest
School District Chesapeake City Public Schools
928 Wickford DrChesapeake, VA 23320
Estimated Value $224,000
Living Area 1,040 SqFt
Beds 3
Baths 2
Year Built 1986
Property Type Townhouse
Ownership Type Related
APN 0367001000530
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1119 Railroad AveChesapeake, VA 23324
Estimated Value $239,000
Living Area 1,197 SqFt
Beds 3
Baths 2
Year Built 1960
Property Type Single Family
Ownership Type Individual
APN 1660000000060
Neighborhood South Norfolk
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
1404 Earle AveChesapeake, VA 23324
Estimated Value $287,000
Living Area 1,828 SqFt
Beds 3
Baths 2
Year Built 1948
Property Type Single Family
Ownership Type Individual
APN 1590000003460
Neighborhood South Norfolk
School District Chesapeake City Public Schools
4109 Everett StChesapeake, VA 23324
Estimated Value $332,000
Living Area 1,672 SqFt
Beds 4
Baths 2.5
Year Built 2017
Property Type Single Family
Ownership Type Individual
APN 1600000001731
Neighborhood South Norfolk
School District Chesapeake City Public Schools