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.7/8/20231129 Cherrytree LnChesapeake, VA 23320
Estimated Value $425,000
Living Area 1,606 SqFt
Beds 4
Baths 2
Year Built 1992
Property Type Single Family
Ownership Type Related
APN 0363007001370
Neighborhood Rivercrest
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
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
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
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
101 Ford StChesapeake, VA 23323
Estimated Value $244,000
Living Area 1,120 SqFt
Beds 3
Baths 1
Year Built 1962
Property Type Single Family
Ownership Type Individual
APN 0261002000790
Neighborhood Deep Creek
School District Chesapeake City Public Schools
704 Rapidan River Ct #BChesapeake, VA 23320
Estimated Value $214,000
Living Area 908 SqFt
Beds 2
Baths 2
Year Built 1991
Property Type Condominium
Ownership Type Corporate
APN 0367004001000
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
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
1125 Lady Ashley DrChesapeake, VA 23320
Estimated Value $402,000
Living Area 2,152 SqFt
Beds 3
Baths 2.5
Year Built 2000
Property Type Condominium
Ownership Type Multiple
APN 0363011000170
Neighborhood Rivercrest
School District Chesapeake City Public Schools
4125 3rd StChesapeake, VA 23324
Estimated Value $218,000
Living Area 924 SqFt
Beds 2
Baths 1
Year Built 1952
Property Type Single Family
Ownership Type Individual
APN 1590000003730
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
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
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
449 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
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