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
Rockwood Dr8343$528,6572,681 Sq.Ft.11/15/2024Rocky Point Run2822$203,929922 Sq.Ft.7/9/2024Rodanthe Ct553$621,2003,399 Sq.Ft.9/23/2024Rodgers St17032$302,1913,310 Sq.Ft.5/16/2025Rohan Way9N/AN/A$703,500N/AN/ARokeby Ave8932$340,2501,755 Sq.Ft.4/19/2025Rollesby Way9333$332,5401,841 Sq.Ft.1/15/2025Rollie Way1033$410,4291,920 Sq.Ft.10/23/2023Rollingswood Ct331$261,0001,000 Sq.Ft.N/ARollingswood Rd1332$331,7691,498 Sq.Ft.12/17/2024Rollis Rd1232$367,0831,619 Sq.Ft.5/5/2025Romaron St1332$348,0001,605 Sq.Ft.11/27/2024Romsey Cir1232$263,3641,231 Sq.Ft.1/29/2025Romulus Pl653$773,1673,675 Sq.Ft.4/17/2024Ronald Ct553$624,4002,982 Sq.Ft.5/20/2024Ronlynn Rd242$500,0001,916 Sq.Ft.8/14/2024Roosevelt Ave2N/AN/AN/AN/AN/ARosana Ct543$612,7502,534 Sq.Ft.7/24/2020Rose Ash Way1342$438,0911,761 Sq.Ft.5/29/2024Rosebud Ln1453$639,8333,017 Sq.Ft.10/8/2020Rose Garden Ln1843$441,2672,184 Sq.Ft.1/21/2025Rosegate St253$691,5002,717 Sq.Ft.5/30/2025Rosehill Dr1433$460,8332,140 Sq.Ft.2/25/2025Rosemarie Way1454$695,6363,314 Sq.Ft.3/31/2023Rosemary Ln2632$387,3461,848 Sq.Ft.7/24/2024Rosemont Ave3832$266,7672,926 Sq.Ft.12/22/2023Rose St6N/AN/A$255,333N/A6/21/2019Rosewell Ave3032$348,5671,596 Sq.Ft.9/19/2024Rosewind Arch853$560,5002,958 Sq.Ft.1/26/2024Rose Wind Ct653$673,1673,459 Sq.Ft.10/3/2012Rosewood Ter1132$375,0001,637 Sq.Ft.5/19/2023Rotan Ct532$263,8001,213 Sq.Ft.5/24/2021Rotunda Ave1243$537,2503,067 Sq.Ft.5/14/2025Roundtable Ct2432$224,5001,432 Sq.Ft.8/22/2022Roundtable Dr2932$308,5771,485 Sq.Ft.7/30/2024Roundtree Cir4832$389,2131,846 Sq.Ft.5/28/2025Rountree Ct643$522,0002,369 Sq.Ft.5/1/2024Rountree Dr1142$508,7002,232 Sq.Ft.8/23/2021Rowland Ave3632$338,9701,877 Sq.Ft.4/8/2025Rowling Way823$288,0001,314 Sq.Ft.4/8/2024Rowlock Ct631$268,8331,201 Sq.Ft.6/28/2023Rowlock Rd2431$266,1301,158 Sq.Ft.3/14/2025Roxbury Ct543$497,0002,735 Sq.Ft.12/12/2023Royal Ct343$491,3332,832 Sq.Ft.6/20/2007Royal Grant Dr4142$538,7112,137 Sq.Ft.5/2/2025Royal Grove Ct4733$345,2671,922 Sq.Ft.2/28/2025Royal Oak Dr1442$500,4292,254 Sq.Ft.2/12/2019Royal Tern Ct2443$538,9572,515 Sq.Ft.9/7/2022Royce Dr4331$366,3491,403 Sq.Ft.5/15/2025Roy Ct654$752,5003,351 Sq.Ft.2/11/2022Ruby Ct1343$516,3082,497 Sq.Ft.12/12/2024Ruddy Ct9N/AN/AN/AN/AN/ARue Marseille9222$216,2611,048 Sq.Ft.3/25/2025Rue Saint La Rogue2022$216,7501,044 Sq.Ft.3/27/2024Ruffin Ricks St1N/AN/AN/AN/AN/ARumford Ct742$527,8572,147 Sq.Ft.1/25/2023Running Stone Way943$518,3752,466 Sq.Ft.9/27/2022Ruritan Blvd11N/AN/AN/A9,423 Sq.Ft.10/18/2024Russell Ln133$391,0002,212 Sq.Ft.5/26/2005Rutgers Ave3842$356,5262,014 Sq.Ft.9/23/2024Rutherford Cir342$468,5002,034 Sq.Ft.1/9/2019Rutherford Ct432$432,5001,600 Sq.Ft.N/ARutherford Dr3832$462,6221,798 Sq.Ft.3/17/2025Ruth St243$347,0001,816 Sq.Ft.9/5/2013Rutledge Rd3631$286,0561,227 Sq.Ft.7/11/2024Rutter Rd2N/AN/A$361,000N/A9/19/2023Ruxton Ct843$540,3752,091 Sq.Ft.4/14/2022Rystrom Run1443$517,5832,531 Sq.Ft.10/2/2023Sabal Palm Ln1N/AN/AN/A286,936 Sq.Ft.3/29/2012Sabbath Ln1343$663,3852,916 Sq.Ft.5/17/2023Saber Dr1943$503,3532,260 Sq.Ft.7/8/2024Saddleback Lndg1032$347,6671,421 Sq.Ft.9/25/2023Saddleback Trail Ct342$510,0001,880 Sq.Ft.11/18/2024Saddleback Trail Rd6042$531,4002,107 Sq.Ft.4/16/2025Saddle Ct2142$439,3892,032 Sq.Ft.12/4/2024Saddlehorn Dr6432$518,1362,072 Sq.Ft.1/23/2025Sagebrook Run2043$375,7781,775 Sq.Ft.3/13/2024Sage Ct1433$444,7502,126 Sq.Ft.8/26/2024Sagen Arch1543$564,6433,125 Sq.Ft.12/23/2024Sail Ct1N/AN/A$2,278,00030,800 Sq.Ft.10/4/2018Sail Fish Quay3823$264,6321,564 Sq.Ft.4/7/2025Saint Andrews Reach8422$219,2861,126 Sq.Ft.6/2/2025Saint Andrews Way5222$218,1761,119 Sq.Ft.11/11/2024Saint Brides Rd23742$636,8552,479 Sq.Ft.5/22/2025Saint Clair Ct432$302,2501,326 Sq.Ft.9/6/2017Saint Clair Dr2442$327,7921,442 Sq.Ft.8/7/2024Saint Julian Dr5631$309,8461,403 Sq.Ft.12/19/2024Saint Kitts Way1453$647,5003,044 Sq.Ft.12/15/2021Saint Lawrence Dr2032$381,6001,868 Sq.Ft.4/16/2020Saint Lukes Church Rd942$362,8004,607 Sq.Ft.3/29/2023Saint Michaels Ct442$544,3332,166 Sq.Ft.1/10/2020Salem St1N/AN/AN/AN/A6/29/2011Salt Marsh Ln1333$333,1671,870 Sq.Ft.6/24/2024Salton Dr3432$288,5761,304 Sq.Ft.5/30/2025Saltwood Ct432$440,2501,702 Sq.Ft.8/12/2015Samantha Ln953$743,1253,378 Sq.Ft.8/4/2023Sampson Creek Rd2432$492,37511,628 Sq.Ft.9/18/2023Sams Cir19N/AN/AN/A44,159 Sq.Ft.3/22/2024Sams Dr3N/AN/AN/A23,507 Sq.Ft.3/30/2015Sandal Arch543$630,4002,858 Sq.Ft.7/8/20234116 Reid StChesapeake, VA 23324
Estimated Value $292,000
Living Area 1,404 SqFt
Beds 3
Baths 2.5
Year Built 2005
Property Type Single Family
Ownership Type Related
APN 1600000001651
Neighborhood South Norfolk
School District Chesapeake City Public Schools
1923 Linster StChesapeake, VA 23324
Estimated Value $323,000
Living Area 1,934 SqFt
Beds 4
Baths 2
Year Built 2016
Property Type Single Family
Ownership Type Multiple
APN 1600000000890
Neighborhood South Norfolk
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
4139 1st StChesapeake, VA 23324
Estimated Value $299,000
Living Area 1,008 SqFt
Beds 2
Baths 1
Year Built 2005
Property Type Single Family
Ownership Type Related
APN 1590000002910
Neighborhood South Norfolk
School District Chesapeake City Public Schools
713 Rue MarseilleChesapeake, VA 23320
Estimated Value $204,000
Living Area 919 SqFt
Beds 2
Baths 2
Year Built 1996
Property Type Condominium
Ownership Type Individual
APN 0367009000670
Neighborhood Rivercrest
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
1741 Fortune TerChesapeake, VA 23323
Estimated Value $418,000
Living Area 2,036 SqFt
Beds 3
Baths 2.5
Year Built 2022
Property Type Condominium
Ownership Type Related
APN 0354003003750
Neighborhood Deep Creek
School District Chesapeake City Public Schools
557 River Creek RdChesapeake, VA 23320
Estimated Value $311,000
Living Area 1,353 SqFt
Beds 3
Baths 2
Year Built 1955
Property Type Single Family
Ownership Type Related
APN 0362001002010
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1712 Foremast LoopChesapeake, VA 23323
Estimated Value $419,000
Living Area 2,120 SqFt
Beds 3
Baths 2.5
Year Built 2020
Property Type Condominium
Ownership Type Individual
APN 0354003004140
Neighborhood Deep Creek
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
527 Twine LnChesapeake, VA 23324
Estimated Value $306,000
Living Area 1,442 SqFt
Beds 2
Baths 2.5
Year Built 2015
Property Type Condominium
Ownership Type Individual
APN 1580001000890
Neighborhood South Norfolk
School District Chesapeake City Public Schools
1512 Shell RdChesapeake, VA 23323
Estimated Value $276,000
Living Area 1,344 SqFt
Beds 3
Baths 2.5
Year Built 1960
Property Type Single Family
Ownership Type Corporate
APN 0261001000010
Neighborhood Deep Creek
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
708 Wyfold CtChesapeake, VA 23320
Estimated Value $469,000
Living Area 2,225 SqFt
Beds 4
Baths 2.5
Year Built 1999
Property Type Single Family
Ownership Type Related
APN 0364009000580
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
1207 Basswood CtChesapeake, VA 23320
Estimated Value $273,000
Living Area 1,264 SqFt
Beds 3
Baths 2.5
Year Built 1987
Property Type Townhouse
Ownership Type Individual
APN 0366008000410
Neighborhood Rivercrest
School District Chesapeake City Public Schools