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
Duxbury Rd1343$534,0002,586 Sq.Ft.9/23/2022Dyanax St1232$272,2501,280 Sq.Ft.7/22/2024Dyer St1243$594,1113,022 Sq.Ft.4/23/2025Eagle Dr1543$514,3082,370 Sq.Ft.2/24/2025Eagle Glen Dr933$460,0002,211 Sq.Ft.6/14/2022Eagle Hill Dr2742$459,0772,201 Sq.Ft.1/19/2023Eagle Pointe Way9733$469,3332,260 Sq.Ft.5/30/2025Eagles Nest843$340,3752,292 Sq.Ft.N/AEaglestone Arch1853$693,1433,183 Sq.Ft.8/21/2023Eagles Trace Path2922$303,7591,411 Sq.Ft.12/11/2024Eaglet Pkwy1N/AN/AN/AN/AN/AEarhart St1132$382,0001,847 Sq.Ft.5/3/2023Earle Ave3232$300,6771,632 Sq.Ft.5/20/2025Earley St843$361,5001,943 Sq.Ft.5/14/2024Eason Rd4642$554,9602,350 Sq.Ft.4/12/2023Eastern Way543$619,5003,222 Sq.Ft.4/1/2024Easton Ct442$511,0002,039 Sq.Ft.6/3/2024East Rd1732$370,8332,124 Sq.Ft.5/26/2021Eastwood Ave1631$270,2671,201 Sq.Ft.12/2/2024Eaton Way142N/A1,392 Sq.Ft.N/AEddington Ct753$673,8573,196 Sq.Ft.4/28/2023Eddystone Dr1253$579,6003,406 Sq.Ft.1/3/2022Edenbridge Dr1843$653,3752,710 Sq.Ft.2/5/2025Eden Sq10N/AN/AN/A1,120 Sq.Ft.9/9/2019Eden Way61N/AN/AN/A18,801 Sq.Ft.3/17/2025Edgerton Rd1132$304,8181,288 Sq.Ft.4/22/2025Edgeware Ct1043$606,5562,824 Sq.Ft.3/31/2023Edgewood Arch2543$597,4782,780 Sq.Ft.5/31/2024Edgewood Ave7531$287,0421,448 Sq.Ft.4/23/2025Edgewood Ct431$266,5001,132 Sq.Ft.7/28/2020Edinburg Ave4232$273,8151,587 Sq.Ft.5/8/2023Edinburgh Ln4N/AN/AN/A35,743 Sq.Ft.11/21/2022Edinburgh Pkwy3253$723,8753,065 Sq.Ft.3/28/2025Edinburg Pkwy2N/AN/A$473,000N/AN/AEdna St1322$259,0003,912 Sq.Ft.4/26/2024Edwards Ct332$380,0001,636 Sq.Ft.10/14/2015Edwin Dr1243$618,10013,636 Sq.Ft.1/30/2025Egret Ct11N/AN/AN/AN/AN/AEight Star Ct553$535,6672,889 Sq.Ft.8/25/2023Eight Star Way5543$520,3262,781 Sq.Ft.7/25/2024Ekaterina Ct1343$720,9093,504 Sq.Ft.2/13/2025Elaina Way543$503,8002,691 Sq.Ft.7/25/2024Elberon Ct442$458,0001,875 Sq.Ft.3/8/2024Elbow Lndg553$708,7503,102 Sq.Ft.10/6/2021Elbow Rd8932$499,6952,706 Sq.Ft.4/10/2025Elbyrne Ct531$253,2501,281 Sq.Ft.6/6/2012Elbyrne Dr4931$262,1841,114 Sq.Ft.8/5/2024Elco St832$292,5712,113 Sq.Ft.10/26/2021Elder Ave13132$328,5321,731 Sq.Ft.5/30/2025Elderberry Ct1643$574,7333,156 Sq.Ft.11/7/2024Elderwood Cmn1432$255,2861,155 Sq.Ft.4/18/2025Eldon Ct353$670,0002,647 Sq.Ft.5/21/2025Eldridge Ln4133$454,4172,244 Sq.Ft.7/18/2024Eleni Ct1153$656,0002,975 Sq.Ft.7/12/2021Eleven Rd72N/A$388,500873 Sq.Ft.N/AEley St331$199,333928 Sq.Ft.3/27/2025Elgin Ct1632$277,0631,474 Sq.Ft.2/14/2024Elias Ct653$695,8333,219 Sq.Ft.5/15/2024Elijah St643$532,6002,353 Sq.Ft.8/28/2019Elindra Ct543$480,4002,097 Sq.Ft.11/21/2018Elisha Sanders Ln2053$634,2502,724 Sq.Ft.8/23/2024Elizabeth Ave1843$357,3131,904 Sq.Ft.2/17/2023Elizabeth Harbor Dr8832$355,0262,049 Sq.Ft.12/31/2024Elizabeth River Way2N/AN/AN/A129,726 Sq.Ft.9/9/2009Elkhart St732$658,5715,386 Sq.Ft.8/14/2023Elkton Ct553$497,2002,726 Sq.Ft.10/22/2020Elkton Dr4543$481,4052,477 Sq.Ft.5/14/2025Ella Ct653$772,5003,155 Sq.Ft.7/30/2024Ellen Ln1032$379,4001,574 Sq.Ft.4/29/2024Elliston Way743$709,3333,226 Sq.Ft.5/14/2025Ellsworth Ave1N/AN/AN/AN/AN/AElm Ave6932$309,7351,463 Sq.Ft.4/3/2025Elm Forest Ct1353$701,1673,325 Sq.Ft.11/12/2024Elmhurst Ave2042$545,4122,336 Sq.Ft.5/25/2023Elmsford Pl332$412,6672,319 Sq.Ft.3/27/2025Eloise Ln543$558,0002,405 Sq.Ft.4/18/2025Elon Ct543$610,4002,696 Sq.Ft.8/28/2024Elverton Ct742$500,1672,279 Sq.Ft.4/18/2022Elysian Pl1N/AN/AN/A22,845 Sq.Ft.6/20/2011Emberhill Ct632$383,2001,664 Sq.Ft.11/5/2024Emberhill Ln1732$432,2941,939 Sq.Ft.8/3/2023Emerald Ct2042$489,9502,209 Sq.Ft.6/7/2024Emerald Sea Dr4142$469,7222,117 Sq.Ft.11/8/2024Emerald Woods Dr1143$605,1433,009 Sq.Ft.3/14/2024Emilee Ct353$680,3333,323 Sq.Ft.5/1/2019Emma St1N/AN/A$368,000N/AN/AEmmbrook Ct642$446,2001,964 Sq.Ft.12/5/2022Emmerson St432$287,5001,282 Sq.Ft.2/6/2015Emmett Dr1332$354,0771,766 Sq.Ft.5/29/2025Emmham Ct453$636,3332,937 Sq.Ft.11/15/2021Emory Pl1N/AN/A$407,000N/AN/AEmporia Ave2831$293,1431,283 Sq.Ft.4/17/2025Emporia Ct1031$289,0001,312 Sq.Ft.4/24/2025Emsworth Dr2433$338,0871,870 Sq.Ft.6/14/2024Enchantment Trl2N/AN/AN/AN/AN/AEnergy Dr1N/AN/AN/AN/A3/25/2025Enfield Ct453$573,2502,680 Sq.Ft.7/15/2020Engle Ave10132$331,5221,604 Sq.Ft.10/3/2024Englewood Dr2432$402,6091,822 Sq.Ft.4/30/2024English Ave9732$349,8591,714 Sq.Ft.5/5/20251648 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
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
103 Ford StChesapeake, VA 23323
Estimated Value $348,000
Living Area 1,972 SqFt
Beds 4
Baths 3
Year Built 2018
Property Type Single Family
Ownership Type Multiple
APN 0261002000780
Neighborhood Deep Creek
School District Chesapeake City Public Schools
709 Helmsdale WayChesapeake, VA 23320
Estimated Value $388,000
Living Area 1,552 SqFt
Beds 3
Baths 2
Year Built 1987
Property Type Single Family
Ownership Type Related
APN 0368001000690
Neighborhood Rivercrest
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
1048 Livingston AveChesapeake, VA 23324
Estimated Value $318,000
Living Area 1,623 SqFt
Beds 3
Baths 2.5
Year Built 2006
Property Type Single Family
Ownership Type Trust
APN 1510000001190
Neighborhood South Norfolk
School District Chesapeake City Public Schools
817 Englewood DrChesapeake, VA 23320
Estimated Value $360,000
Living Area 1,649 SqFt
Beds 3
Baths 2
Year Built 1966
Property Type Single Family
Ownership Type Individual
APN 0361008000960
Neighborhood Rivercrest
School District Chesapeake City Public Schools
205 Dunn StChesapeake, VA 23320
Estimated Value $465,000
Living Area 3,027 SqFt
Beds 5
Baths 3.5
Year Built 2003
Property Type Single Family
Ownership Type Multiple
APN 0351008000030
Neighborhood Rivercrest
School District Chesapeake City Public Schools
875 Rivanna River ReachChesapeake, VA 23320
Estimated Value $280,000
Living Area 1,434 SqFt
Beds 2
Baths 1.5
Year Built 1990
Property Type Condominium
Ownership Type Individual
APN 0367003000600
Neighborhood Rivercrest
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
4100 Dyanax StChesapeake, VA 23324
Estimated Value $225,000
Living Area 1,188 SqFt
Beds 3
Baths 1
Year Built 1942
Property Type Single Family
Ownership Type Individual
APN 1590000001440
Neighborhood South Norfolk
School District Chesapeake City Public Schools
400 Harbour North DrChesapeake, VA 23320
Estimated Value $196,000
Living Area 1,216 SqFt
Beds 3
Baths 1.5
Year Built 1978
Property Type Townhouse
Ownership Type Individual
APN 0364003000260
Neighborhood Rivercrest
School District Chesapeake City Public Schools
568 Marc Smiley RdChesapeake, VA 23324
Estimated Value $318,000
Living Area 1,720 SqFt
Beds 3
Baths 2.5
Year Built 2017
Property Type Condominium
Ownership Type Individual
APN 1580001001270
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
4123 Everett St #BChesapeake, VA 23324
Estimated Value $377,000
Living Area 2,164 SqFt
Beds 5
Baths 3
Year Built 2017
Property Type Single Family
Ownership Type Related
APN 1600000001761
Neighborhood South Norfolk
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