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
Claremont Ct554$792,0003,423 Sq.Ft.3/10/2022Clarendon Cir543$611,6003,193 Sq.Ft.8/8/2001Clarion Ln2143$481,2782,465 Sq.Ft.4/29/2025Clark Ct1132$314,3001,495 Sq.Ft.4/2/2021Clarks Cir1853$669,8333,567 Sq.Ft.7/22/2021Clay Ave1031$281,6671,251 Sq.Ft.2/10/2025Clayton Ct1332$344,3331,489 Sq.Ft.10/17/2023Claytor Ct1443$649,5833,195 Sq.Ft.11/12/2024Clearfield Ave6142$451,8332,342 Sq.Ft.1/22/2024Clear Springs Ct743$454,4292,166 Sq.Ft.11/14/2022Clearwater Ln8343$666,6162,982 Sq.Ft.5/13/2025Clemson Ave2432$348,8331,914 Sq.Ft.4/2/2025Cleona Dr2831$259,3571,156 Sq.Ft.11/14/2023Clifton St4542$386,7182,034 Sq.Ft.3/26/2025Clipperton St232$259,0001,043 Sq.Ft.4/21/2017Cloud Nine Ct642$411,0001,676 Sq.Ft.11/15/2024Clove Ct832$271,3751,642 Sq.Ft.12/1/2021Clover Dr2031$367,5501,299 Sq.Ft.12/22/2021Clover Hill Ct1253$732,8333,575 Sq.Ft.8/30/2023Clover Meadow Rd1N/AN/A$2,961,00030,045 Sq.Ft.4/1/2024Clover Meadows Dr17322$161,118999 Sq.Ft.3/26/2025Clover Rd5722$192,6911,062 Sq.Ft.4/15/2025Club House Dr3854$773,5433,612 Sq.Ft.1/27/2024Club Pines Ct453$581,2502,883 Sq.Ft.6/29/2016Club Point Rd1933$379,6671,611 Sq.Ft.3/4/2024Clydes Way1053$706,4293,225 Sq.Ft.10/10/2023Coachman Dr2442$407,7622,323 Sq.Ft.12/19/2024Coastal Ln1N/AN/AN/A2,336 Sq.Ft.10/29/2020Coastal Way6N/AN/A$367,0001,977 Sq.Ft.4/22/2016Cobb Ave531$268,0001,252 Sq.Ft.1/26/2021Cobb Island Ct1532$305,3571,451 Sq.Ft.10/4/2021Cobble Scott Way1343$995,0003,908 Sq.Ft.5/14/2025Cobblestone Ct642$419,0002,506 Sq.Ft.5/30/2007Cobblewood Arch6732$262,7761,155 Sq.Ft.2/19/2025Cobblewood Bnd5632$248,9821,130 Sq.Ft.6/4/2025Codorus St1833$459,4122,228 Sq.Ft.12/9/2024Coffman Blvd6332$361,6211,581 Sq.Ft.3/20/2025Cogliandro Ct332$412,0001,745 Sq.Ft.1/25/2012Cogliandro Dr6032$437,2241,825 Sq.Ft.1/28/2025Coinbrook Ln1154$730,0003,646 Sq.Ft.2/2/2022Coker Pl353$609,0003,030 Sq.Ft.6/27/2023Colby St3N/AN/A$228,500N/A7/19/2016Cole Dr1832$339,7651,818 Sq.Ft.3/15/2024Coleshill Ln2343$551,7502,932 Sq.Ft.8/12/2024Colindale Rd6622$226,3691,345 Sq.Ft.5/27/2025Collington Dr1132$394,6361,483 Sq.Ft.9/3/2024Collingwood Ave1032$258,4001,216 Sq.Ft.2/4/2025Collins Blvd3831$313,8331,438 Sq.Ft.12/18/2024Collins Ct332$311,3331,507 Sq.Ft.10/23/2013Colonel Byrd St5643$572,3812,571 Sq.Ft.11/3/2024Colonial Vw1942$521,2781,927 Sq.Ft.12/5/2022Colonial Way7432$249,7671,231 Sq.Ft.5/15/2025Colony Dr2532$402,9201,397 Sq.Ft.8/12/2021Colony Manor Rd3632$359,8821,661 Sq.Ft.3/21/2025Colony Pointe Dr1843$608,8753,208 Sq.Ft.9/13/2024Colt Arch454$480,5002,241 Sq.Ft.1/5/2000Colton Ct643$553,0002,410 Sq.Ft.8/19/2024Columbo Ave2342$440,3912,018 Sq.Ft.4/29/2022Columbus Ave1643$374,1252,230 Sq.Ft.9/11/2024Combs Ln1543$511,8182,625 Sq.Ft.5/22/2024Commerce Ave10332$277,2021,557 Sq.Ft.4/10/2025Commish Ln554$740,2003,825 Sq.Ft.8/3/2022Common Ln1N/AN/AN/A5,930 Sq.Ft.4/29/1999Commonwealth Ave2432$355,2731,600 Sq.Ft.8/23/2024Compaz Rd1932$353,5561,742 Sq.Ft.9/10/2020Condor Ct543$540,4002,934 Sq.Ft.11/8/2021Condor Dr4643$549,3562,478 Sq.Ft.5/14/2025Condor Lndg442$547,0002,627 Sq.Ft.6/15/2016Conference Center Dr2N/AN/AN/A46,204 Sq.Ft.4/7/2016Connie Ln742$455,5711,803 Sq.Ft.5/12/2023Conquest Dr1N/AN/AN/A141,461 Sq.Ft.N/AConrad Ave3522$251,7141,621 Sq.Ft.5/27/2025Conservancy Dr6743$512,8932,354 Sq.Ft.4/4/2025Conservancy Way1N/AN/AN/A148,905 Sq.Ft.12/28/2023Conservation Ct843$623,7502,865 Sq.Ft.11/27/2023Conservation Xing2954$709,4293,488 Sq.Ft.5/27/2025Consolvo Pl1533$341,5711,939 Sq.Ft.2/13/2025Constable Dr843$631,8572,603 Sq.Ft.6/26/2024Constance Dr1343$519,7692,844 Sq.Ft.4/9/2024Contrell Ct1332$339,7691,527 Sq.Ft.12/16/2021Conway Rd1242$439,5001,522 Sq.Ft.11/6/2020Cook Blvd33N/AN/AN/A45,048 Sq.Ft.4/10/2025Cookes Mill Rd1133$664,6672,340 Sq.Ft.5/28/2020Cookham Arch1453$674,1823,288 Sq.Ft.9/3/2024Cool Brook Trl2332$352,3181,501 Sq.Ft.10/27/2023Cooper Ln1143$576,9092,332 Sq.Ft.11/19/2024Copeland Ct332$499,6672,131 Sq.Ft.12/5/2023Copeland Dr843$487,5712,342 Sq.Ft.12/7/2016Copley Ct1043$462,2222,049 Sq.Ft.5/24/2024Copperfield Dr1242$457,9172,160 Sq.Ft.3/20/2025Copper Knoll Ln3553$636,5522,670 Sq.Ft.5/19/2025Copper Stone Cir18342$540,5772,503 Sq.Ft.4/23/2025Copper Stone Ct942$488,6252,151 Sq.Ft.7/18/2023Copper Way143$639,0002,428 Sq.Ft.1/29/2018Coral Ave1332$283,0771,403 Sq.Ft.2/1/2024Coral Ivy Ct742$485,0002,276 Sq.Ft.9/22/2020Coral Ivy Ln2242$478,2502,054 Sq.Ft.2/20/2024Coral Water Ct343$747,3333,155 Sq.Ft.5/8/2023Corapeake Dr8342$480,2661,990 Sq.Ft.3/28/2025Cora St2N/A1N/A1,409 Sq.Ft.4/15/20161824 Warfield StChesapeake, VA 23324
Estimated Value $282,000
Living Area 1,476 SqFt
Beds 3
Baths 2.5
Year Built 2006
Property Type Single Family
Ownership Type Related
APN 1600000002671
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
1708 Kinser CtChesapeake, VA 23324
Estimated Value $422,000
Living Area 2,432 SqFt
Beds 4
Baths 2.5
Year Built 2003
Property Type Single Family
Ownership Type Individual
APN 1521001000080
Neighborhood South Norfolk
School District Chesapeake City Public Schools
1702 Foremast LoopChesapeake, VA 23323
Estimated Value $384,000
Living Area 1,760 SqFt
Beds 3
Baths 2.5
Year Built 2020
Property Type Condominium
Ownership Type Individual
APN 0354003002320
Neighborhood Deep Creek
School District Chesapeake City Public Schools
1024 Calloway AveChesapeake, VA 23324
Estimated Value $219,000
Living Area 912 SqFt
Beds 3
Baths 1.5
Year Built 1972
Property Type Single Family
Ownership Type Individual
APN 1520000001640
Neighborhood South Norfolk
School District Chesapeake City Public Schools
604 Pine BndChesapeake, VA 23320
Estimated Value $254,000
Living Area 1,273 SqFt
Beds 3
Baths 2.5
Year Built 1979
Property Type Townhouse
Ownership Type Individual
APN 0366001000280
Neighborhood Rivercrest
School District Chesapeake City Public Schools
4309 Pickney LnChesapeake, VA 23324
Estimated Value $324,000
Living Area 1,720 SqFt
Beds 3
Baths 2.5
Year Built 2018
Property Type Condominium
Ownership Type Multiple
APN 1580001000780
Neighborhood South Norfolk
School District Chesapeake City Public Schools
1456 Culpepper AveChesapeake, VA 23323
Estimated Value $369,000
Living Area 2,268 SqFt
Beds 4
Baths 2.5
Year Built 1978
Property Type Single Family
Ownership Type Multiple
APN 0255001002350
Neighborhood Deep Creek
School District Chesapeake City Public Schools
1359 E Eva BlvdChesapeake, VA 23320
Estimated Value $367,000
Living Area 1,844 SqFt
Beds 4
Baths 2.5
Year Built 2000
Property Type Single Family
Ownership Type Related
APN 0272007000090
Neighborhood Rivercrest
School District Chesapeake City Public Schools
928 Wickford DrChesapeake, VA 23320
Estimated Value $224,000
Living Area 1,040 SqFt
Beds 3
Baths 2
Year Built 1986
Property Type Townhouse
Ownership Type Related
APN 0367001000530
Neighborhood Rivercrest
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
4201 1st StChesapeake, VA 23324
Estimated Value $213,000
Living Area 889 SqFt
Beds 3
Baths 1
Year Built 1940
Property Type Single Family
Ownership Type Corporate
APN 1590000002990
Neighborhood South Norfolk
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
614 Reunion StChesapeake, VA 23324
Estimated Value $317,000
Living Area 1,570 SqFt
Beds 2
Baths 2.5
Year Built 2014
Property Type Condominium
Ownership Type Individual
APN 1580001000080
Neighborhood South Norfolk
School District Chesapeake City Public Schools
1300 Lucas AveChesapeake, VA 23324
Estimated Value $218,000
Living Area 1,000 SqFt
Beds 3
Baths 1.5
Year Built 1987
Property Type Single Family
Ownership Type Individual
APN 1590000002490
Neighborhood South Norfolk
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