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
Corbin Dr343$927,3333,586 Sq.Ft.1/13/2015Corby Cir2032$265,2001,409 Sq.Ft.1/10/2025Corby Glen Ave3743$643,8892,439 Sq.Ft.2/12/2025Corcormant Ln1643$587,5002,982 Sq.Ft.1/19/2024Corden Ave932$282,7781,614 Sq.Ft.10/31/2024Cordgrass Ct843$469,3332,150 Sq.Ft.4/25/2025Cordova Ct243$553,5002,632 Sq.Ft.12/20/2016Corkwood Cir5232$262,5881,257 Sq.Ft.10/24/2023Corlew Ct843$531,7142,567 Sq.Ft.7/14/2021Corner Lot Cor12N/AN/A$218,000N/A10/31/2023Cornet St3742$418,4721,934 Sq.Ft.8/9/2024Cornick Ave1832$323,5001,544 Sq.Ft.11/14/2024Cornland Rd5743$716,0712,477 Sq.Ft.8/9/2024Corolla Dr1443$590,3002,717 Sq.Ft.6/14/2024Corona Ln2053$655,8952,948 Sq.Ft.6/13/2023Corporate Ln12N/AN/AN/A14,435 Sq.Ft.2/25/2021Corwood Ct543$803,0003,306 Sq.Ft.12/14/2020Cory Ln2143$482,8572,158 Sq.Ft.1/22/2025Costa Ave932$336,3331,771 Sq.Ft.2/2/2021Cottage Pl543$508,2002,193 Sq.Ft.3/4/2022Cotton Mill Ct932$370,6671,629 Sq.Ft.1/14/2025Cottonwood Ln1132$401,8181,837 Sq.Ft.4/18/2023Country Cir2043$392,8332,095 Sq.Ft.10/14/2022Country Club Blvd9143$644,3573,006 Sq.Ft.2/5/2025Country Club Ct1354$690,3083,848 Sq.Ft.9/6/2023Country Mill Ct343$723,0002,804 Sq.Ft.7/17/2020Country Mill Run2043$619,7502,869 Sq.Ft.11/21/2023Country Rd2442$325,8331,881 Sq.Ft.2/24/2025Country Trail Ct443$534,0002,044 Sq.Ft.4/26/2022Country Trail Rd242$524,5002,035 Sq.Ft.N/ACove Cir743$467,5712,389 Sq.Ft.6/29/2017Covenant Way1253$651,3332,803 Sq.Ft.4/14/2022Coventry Close2N/AN/AN/A72,464 Sq.Ft.12/2/2024Coveside Ln1N/AN/AN/A439,870 Sq.Ft.4/3/2012Covey Ct743$496,4292,260 Sq.Ft.3/30/2022Covington Ct2033$392,9412,051 Sq.Ft.4/30/2025Covington Dr643$384,6671,995 Sq.Ft.12/3/2021Cowpens Ct953$627,6252,581 Sq.Ft.3/4/2022Cox Ave2332$292,0431,474 Sq.Ft.6/4/2025Cozy Cor1N/AN/AN/A30,232 Sq.Ft.11/9/2021Crabtree Ct1042$376,1001,794 Sq.Ft.4/19/2013Cranberry Dr2933$526,7862,515 Sq.Ft.3/13/2024Cranham Rd143$612,0002,485 Sq.Ft.N/ACranston Dr3342$428,0311,821 Sq.Ft.5/21/2024Crayton Way1243$718,4172,746 Sq.Ft.4/17/2023Creef Ln632$362,4001,768 Sq.Ft.10/26/2020Creek Ct643$683,1673,066 Sq.Ft.12/13/2011Creek Dr2742$374,3752,051 Sq.Ft.4/9/2025Creek Ln243$586,5003,152 Sq.Ft.6/15/2021Creeks Edge Ct842$479,6252,089 Sq.Ft.6/20/2019Creekside Cres10132$270,3881,336 Sq.Ft.11/4/2024Creekside Ct3632$280,2001,430 Sq.Ft.1/30/2025Creekview Ct442$495,3332,262 Sq.Ft.10/14/2022Creekview Dr2943$499,7312,344 Sq.Ft.5/20/2024Creekwood Dr8142$467,5691,991 Sq.Ft.5/14/2025Crescent Trce1843$522,7652,658 Sq.Ft.3/5/2023Crescentwood Arch1143$519,2002,632 Sq.Ft.4/22/2019Creston Ct1153$629,8752,916 Sq.Ft.8/19/2024Crestwood Ln1N/AN/AN/A196,800 Sq.Ft.8/19/2010Crestwynd Cir643$611,1672,525 Sq.Ft.5/14/2018Crestwynd Dr1343$619,8332,577 Sq.Ft.5/23/2023Cricket Ct743$615,8573,049 Sq.Ft.11/7/2022Cricket Hollow Ln5332$283,8271,559 Sq.Ft.3/24/2025Cricket Ln2322$280,5001,575 Sq.Ft.5/4/2023Crimson Ivy Ln1242$485,9092,327 Sq.Ft.4/17/2025Cristfield Rd3743$459,4062,213 Sq.Ft.4/11/2025Crittenden Ct443$470,2502,112 Sq.Ft.7/13/2023Croatan Ct942$521,5002,187 Sq.Ft.11/12/2021Croft Xing954$753,1253,813 Sq.Ft.4/1/2024Cromwell Ave2931$293,2761,174 Sq.Ft.2/24/2025Cromwell Ct632$294,2501,380 Sq.Ft.4/24/2025Cronin Ct643$528,5002,274 Sq.Ft.12/21/2020Crooked Stick Xing2122$330,5501,485 Sq.Ft.8/31/2023Crossbow Ct543$583,7503,143 Sq.Ft.5/29/2019Cross Creek Quay2N/AN/AN/A168 Sq.Ft.N/ACrossings Ct943$547,8892,983 Sq.Ft.7/14/2021Crossings Dr6843$538,6672,837 Sq.Ft.7/26/2024Crossland Dr1843$519,9442,529 Sq.Ft.4/17/2025Cross Quay1153$644,5453,380 Sq.Ft.3/22/2024Cross St1832$318,5001,492 Sq.Ft.7/19/2024Crosstie Ct343$484,3332,096 Sq.Ft.7/11/2024Crosstie Ln1343$497,2732,224 Sq.Ft.2/18/2025Crossways Blvd29N/AN/AN/A89,573 Sq.Ft.12/12/2024Crosswinds Dr1N/AN/AN/A1,921 Sq.Ft.N/ACrosswood Ct743$654,2862,851 Sq.Ft.5/2/2024Crosswood Ln1543$618,5332,553 Sq.Ft.6/19/2024Crowell Ave2831$270,6001,920 Sq.Ft.3/20/2025Crowley Cir732$300,1431,268 Sq.Ft.11/21/2023Crown Cres4342$371,9511,970 Sq.Ft.4/27/2023Crown Ct832$365,5001,911 Sq.Ft.9/4/2019Crystal Ave3831$254,5911,348 Sq.Ft.5/13/2024Crystalwood Cir3643$467,6472,324 Sq.Ft.5/30/2025Cuddy Ct642$532,0002,684 Sq.Ft.6/6/2024Cuervo Ct3443$606,3232,785 Sq.Ft.12/17/2024Cuffee Rd1042$415,8751,947 Sq.Ft.8/31/2020Cuffeytown St2N/AN/AN/AN/A5/29/2018Cullen Ave4442$305,9521,744 Sq.Ft.8/5/2024Cully St332$421,5001,843 Sq.Ft.12/18/2021Culpepper Ave2042$336,6501,529 Sq.Ft.6/26/2024Cumberland Ct3553$662,8243,092 Sq.Ft.4/5/20241818 Aft WayChesapeake, VA 23323
Estimated Value $415,000
Living Area 2,036 SqFt
Beds 3
Baths 2.5
Year Built 2021
Property Type Condominium
Ownership Type Multiple
APN 0354003001890
Neighborhood Deep Creek
School District Chesapeake City Public Schools
1724 2nd StChesapeake, VA 23324
Estimated Value $363,000
Living Area 1,488 SqFt
Beds 3
Baths 2
Year Built 1966
Property Type Single Family
Ownership Type Related
APN 1520000005120
Neighborhood South Norfolk
School District Chesapeake City Public Schools
704 Kirkwall CtChesapeake, VA 23320
Estimated Value $460,000
Living Area 1,996 SqFt
Beds 3
Baths 2.5
Year Built 1988
Property Type Single Family
Ownership Type Related
APN 0368001000950
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
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
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
1709 Foremast LoopChesapeake, VA 23323
Estimated Value $379,000
Living Area 1,720 SqFt
Beds 3
Baths 2.5
Year Built 2020
Property Type Condominium
Ownership Type Related
APN 0354003002410
Neighborhood Deep Creek
School District Chesapeake City Public Schools
705 Montrose CtChesapeake, VA 23320
Estimated Value $288,000
Living Area 1,516 SqFt
Beds 3
Baths 2.5
Year Built 1991
Property Type Townhouse
Ownership Type Individual
APN 0367002001510
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
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
704 Cordgrass CtChesapeake, VA 23320
Estimated Value $455,000
Living Area 2,189 SqFt
Beds 4
Baths 2.5
Year Built 1990
Property Type Single Family
Ownership Type Individual
APN 0369001000340
Neighborhood Rivercrest
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
1202 Basswood CtChesapeake, VA 23320
Estimated Value $266,000
Living Area 1,260 SqFt
Beds 3
Baths 2.5
Year Built 1987
Property Type Townhouse
Ownership Type Related
APN 0366008000450
Neighborhood Rivercrest
School District Chesapeake City Public Schools
308 Esplanade PlChesapeake, VA 23320
Estimated Value $356,000
Living Area 1,849 SqFt
Beds 3
Baths 2.5
Year Built 1994
Property Type Townhouse
Ownership Type Multiple
APN 0367008000200
Neighborhood Rivercrest
School District Chesapeake City Public Schools
117 Gibson DrChesapeake, VA 23320
Estimated Value $452,000
Living Area 2,142 SqFt
Beds 4
Baths 2
Year Built 1974
Property Type Single Family
Ownership Type Related
APN 0361005000200
Neighborhood Rivercrest
School District Chesapeake City Public Schools