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
Cayce Cir631$242,200961 Sq.Ft.7/29/2023Cayce Ct731$230,667944 Sq.Ft.4/24/2020Cayce Dr1932$271,9471,244 Sq.Ft.8/7/2024Cayland Ct643$599,1672,317 Sq.Ft.12/2/2015Caymon Ct653$511,6672,907 Sq.Ft.1/28/2021Caymus Rd1N/AN/AN/A240,547 Sq.Ft.10/30/2019Cecilia Ct642$442,6671,898 Sq.Ft.7/14/2022Cecilia Ter3442$475,7352,184 Sq.Ft.4/29/2022Cedar Chase1N/AN/AN/A100 Sq.Ft.N/ACedar Cmns2133$402,1111,973 Sq.Ft.5/21/2025Cedar Cove Ln2842$404,2691,780 Sq.Ft.8/26/2024Cedar Craft Ln932$383,7781,783 Sq.Ft.5/30/2025Cedar Creek Ter1722$290,2941,252 Sq.Ft.4/23/2025Cedar Grove Cres3642$377,8572,196 Sq.Ft.4/22/2025Cedar Lakes Dr6N/AN/AN/A8,004 Sq.Ft.3/15/2019Cedarlane Ct843$558,6252,561 Sq.Ft.2/1/2024Cedar Ln2142$520,5502,475 Sq.Ft.4/26/2023Cedar Mill Sq4822$276,6041,242 Sq.Ft.11/6/2024Cedar Pointe Ct353$505,5002,518 Sq.Ft.5/10/2018Cedar Pointe Ln2442$470,3642,111 Sq.Ft.2/24/2023Cedar Rd33832$407,9246,596 Sq.Ft.5/13/2025Cedarville Rd9743$747,8002,592 Sq.Ft.12/13/2024Cedarwood Ct1443$569,2312,681 Sq.Ft.6/2/2023Cedarwood Ln1642$514,8752,238 Sq.Ft.7/8/2022Cedarwood Trce443$530,2502,306 Sq.Ft.1/11/2023Center Mast Crst1643$376,8132,271 Sq.Ft.3/10/2023Centerville Tpke31432$525,9683,538 Sq.Ft.5/27/2025Centurion Cir1433$427,8462,005 Sq.Ft.6/13/2024Chablis St153$454,0002,697 Sq.Ft.1/26/2010Chadswyck Rd1632$374,0001,614 Sq.Ft.4/25/2023Chaffins Ct553$762,4003,496 Sq.Ft.12/28/2021Chalbourne Ct343$525,0002,433 Sq.Ft.3/7/2019Chalbourne Dr4643$544,3262,297 Sq.Ft.12/20/2024Challis Ct532$310,0001,270 Sq.Ft.12/2/2021Challis Dr1032$293,3001,075 Sq.Ft.1/15/2024Champion Ct743$568,7142,823 Sq.Ft.7/30/2024Chancery Ln2522$229,3601,347 Sq.Ft.11/6/2024Chandler Dr2343$612,6672,798 Sq.Ft.10/11/2024Chandon Dr843$544,3752,647 Sq.Ft.5/18/2023Channel Pl1N/AN/AN/A82,416 Sq.Ft.N/AChanning Arch743$536,1432,409 Sq.Ft.1/9/2025Channing Way543$563,8002,566 Sq.Ft.8/28/2020Chantilly Ln1943$635,9382,990 Sq.Ft.8/22/2022Chapel Ave1442$317,4172,185 Sq.Ft.11/14/2024Chapel Hill Dr1253$657,3002,819 Sq.Ft.5/28/2025Chaplin Rd1N/AN/AN/AN/AN/ACharca Ct442$515,7502,066 Sq.Ft.7/23/2019Charing Cross743$577,3332,632 Sq.Ft.9/30/2021Charisse Ct542$398,2501,520 Sq.Ft.7/3/2023Charles St1243$394,8182,254 Sq.Ft.10/13/2023Charleston St1333$458,9002,179 Sq.Ft.6/12/2024Charlotte Ann Ct1153$659,2223,467 Sq.Ft.10/10/2019Charlotte St1942$386,0002,157 Sq.Ft.5/22/2025Charlton Ct1931$294,4441,210 Sq.Ft.10/3/2024Charlton Dr5132$454,9351,855 Sq.Ft.4/25/2025Chasebury Pl1N/AN/AN/AN/AN/AChateau Cir954$738,5713,592 Sq.Ft.4/28/2025Chatham Ln2333$382,3181,776 Sq.Ft.9/23/2024Chattanooga St6032$407,4921,631 Sq.Ft.4/23/2025Chaz Ct1044$671,7503,442 Sq.Ft.9/12/2022Checkerspot Way3253$674,5773,008 Sq.Ft.4/24/2025Chelbrook Rd2043$506,8502,124 Sq.Ft.7/12/2023Chelsea Ln953$740,8003,428 Sq.Ft.7/17/2023Cheltingham Ct1932$476,2631,919 Sq.Ft.5/10/2023Cherie Ct343$508,0002,189 Sq.Ft.N/ACherry Forest Ct943$668,7782,954 Sq.Ft.5/9/2024Cherryhill Ln1042$396,2222,207 Sq.Ft.12/21/2023Cherry Ln2032$329,1581,558 Sq.Ft.5/15/2023Cherrytree Ln4243$530,3592,573 Sq.Ft.10/24/2024Chesapeake Ave21042$310,4262,080 Sq.Ft.4/30/2025Chesapeake Cir831$296,3751,258 Sq.Ft.8/27/2021Chesapeake Ct631$289,8331,196 Sq.Ft.11/15/2024Chesapeake Dr3632$337,9703,162 Sq.Ft.4/25/2025Chesapeake Expy1N/AN/A$472,000N/AN/AChesapeake Square Blvd5N/AN/AN/A8,779 Sq.Ft.12/10/2019Chesapeake Square Ring Rd11N/AN/AN/A70,482 Sq.Ft.6/5/2024Cheshire Forest Dr3943$617,1942,914 Sq.Ft.10/11/2024Cheslie Arch2053$692,4712,949 Sq.Ft.8/30/2023Cheslie Ct543$740,0003,138 Sq.Ft.4/3/2019Chessie Ct532$435,6001,660 Sq.Ft.11/20/2020Chessire Ct642$468,1671,772 Sq.Ft.6/30/2009Chesslawn Cir2332$400,1821,805 Sq.Ft.4/4/2025Chesterfield Loop6253$595,7782,989 Sq.Ft.5/28/2025Chesterfield Ter1743$459,5632,124 Sq.Ft.7/9/2021Chestnut Ave6642$333,3751,657 Sq.Ft.3/3/2025Chipada Ct1443$484,1542,616 Sq.Ft.3/31/2025Chowan Ave1532$416,5711,877 Sq.Ft.1/28/2022Chris Ct1243$661,9092,951 Sq.Ft.4/27/2022Christa Dr1442$441,5002,007 Sq.Ft.5/27/2022Christian Ave3032$259,1671,480 Sq.Ft.5/21/2025Christie Ct3N/AN/A$361,667N/AN/AChristie Ter12N/AN/A$361,667N/A2/27/2018Christopher Dr2732$413,6921,840 Sq.Ft.12/9/2024Churchill Dr1453$729,8333,705 Sq.Ft.8/24/2021Churchland Blvd2442$257,00011,134 Sq.Ft.12/13/2024Cicero Ct2154$776,9003,655 Sq.Ft.11/8/2024Cinnamon Ct2022$219,8001,315 Sq.Ft.4/25/2025Cistern Cir643$489,5002,135 Sq.Ft.6/14/2024Citizen Cir1142$390,4442,134 Sq.Ft.5/28/2025Clara Dr1043$565,5712,900 Sq.Ft.8/2/2021449 Cobblewood BndChesapeake, VA 23320
Estimated Value $233,000
Living Area 1,060 SqFt
Beds 3
Baths 1
Year Built 1986
Property Type Single Family
Ownership Type Individual
APN 0366007000100
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1216 Destiny WayChesapeake, VA 23320
Estimated Value $434,000
Living Area 1,559 SqFt
Beds 4
Baths 2.5
Year Built 2010
Property Type Single Family
Ownership Type Related
APN 0353001000120
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1208 Earle AveChesapeake, VA 23324
Estimated Value $326,000
Living Area 1,118 SqFt
Beds 3
Baths 1.5
Year Built 1940
Property Type Single Family
Ownership Type Individual
APN 1590000001650
Neighborhood South Norfolk
School District Chesapeake City Public Schools
510 Sloane StChesapeake, VA 23324
Estimated Value $307,000
Living Area 1,464 SqFt
Beds 2
Baths 2.5
Year Built 2016
Property Type Condominium
Ownership Type Individual
APN 1580001001430
Neighborhood South Norfolk
School District Chesapeake City Public Schools
4104 3rd StChesapeake, VA 23324
Estimated Value $396,000
Living Area 2,207 SqFt
Beds 5
Baths 3
Year Built 2010
Property Type Single Family
Ownership Type Individual
APN 1590000003330
Neighborhood South Norfolk
School District Chesapeake City Public Schools
703 Durham AveChesapeake, VA 23320
Estimated Value $408,000
Living Area 2,501 SqFt
Beds 4
Baths 2.5
Year Built 2002
Property Type Single Family
Ownership Type Related
APN 0351004003070
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1813 Hazelwood RdChesapeake, VA 23323
Estimated Value $744,000
Living Area 3,531 SqFt
Beds 5
Baths 3.5
Year Built 2012
Property Type Single Family
Ownership Type Related
APN 0344002003360
Neighborhood Deep Creek
School District Chesapeake City Public Schools
1040 Campostella RdChesapeake, VA 23320
Estimated Value $226,000
Living Area 917 SqFt
Beds 3
Baths 1
Year Built 1955
Property Type Single Family
Ownership Type Individual
APN 0362001001450
Neighborhood Rivercrest
School District Chesapeake City Public Schools
4101 Dyanax StChesapeake, VA 23324
Estimated Value $182,000
Living Area 896 SqFt
Beds 2
Baths 1
Year Built 1940
Property Type Single Family
Ownership Type Individual
APN 1590000001430
Neighborhood South Norfolk
School District Chesapeake City Public Schools
4152 Williamson StChesapeake, VA 23324
Estimated Value $368,000
Living Area 3,274 SqFt
Beds 5
Baths 3
Year Built 1959
Property Type Single Family
Ownership Type Multiple
APN 1600000002510
Neighborhood South Norfolk
School District Chesapeake City Public Schools
832 Wickford DrChesapeake, VA 23320
Estimated Value $186,000
Living Area 860 SqFt
Beds 2
Baths 1
Year Built 1985
Property Type Townhouse
Ownership Type Individual
APN 0367001000330
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
209 Outlaw StChesapeake, VA 23320
Estimated Value $399,000
Living Area 2,236 SqFt
Beds 4
Baths 2.5
Year Built 2003
Property Type Single Family
Ownership Type Multiple
APN 0351004001500
Neighborhood Rivercrest
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
1727 Faulk StChesapeake, VA 23323
Estimated Value $281,000
Living Area 1,424 SqFt
Beds 3
Baths 2.5
Year Built 2004
Property Type Single Family
Ownership Type Individual
APN 0261002000150
Neighborhood Deep Creek
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