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
Angora Ct742$391,4292,025 Sq.Ft.7/27/2021Angora Dr2032$363,5001,895 Sq.Ft.10/7/2024Angus Rd2142$474,6842,125 Sq.Ft.7/28/2023Anita Cir2643$491,1922,711 Sq.Ft.5/30/2024Annabranch Trce1643$540,0713,152 Sq.Ft.3/28/2023Anna Joy Ct743$652,4293,125 Sq.Ft.12/3/2024Annaka Loop2343$452,0502,259 Sq.Ft.2/27/2025Anna Maria Way542$360,2001,939 Sq.Ft.7/2/2021Annandale Dr1343$484,0002,438 Sq.Ft.2/23/2024Annapolis Dr3142$596,4523,031 Sq.Ft.5/22/2025Anne Ave7331$259,1671,070 Sq.Ft.10/31/2024Annette St4442$262,9321,569 Sq.Ft.4/7/2023Annias Way453$770,3333,713 Sq.Ft.3/10/2016Annie Cir3843$520,6392,626 Sq.Ft.5/28/2025Annie Olah Cres3354$691,0003,251 Sq.Ft.12/26/2024Anointed Aly634$465,8332,221 Sq.Ft.7/10/2024Ansell Rd832$704,3331,315 Sq.Ft.10/27/2021Anthony Dr1932$328,1251,605 Sq.Ft.12/17/2024Appalachian Blvd163$720,0003,196 Sq.Ft.11/3/2014Appalachian Ct4253$635,0312,877 Sq.Ft.1/31/2025Appaloosa Trl10442$406,5051,711 Sq.Ft.1/11/2025April Ct433$787,6672,395 Sq.Ft.6/1/2021Arabian Arch453$721,0003,424 Sq.Ft.7/23/2012Arbor Ct432$292,0001,390 Sq.Ft.8/2/2021Arboretum Trl2553$614,9473,076 Sq.Ft.3/18/2024Arbuckle St4043$590,0003,079 Sq.Ft.1/7/2025Arbutus Cir1632$388,1882,212 Sq.Ft.3/17/2023Arcadia Rd3342$476,5362,193 Sq.Ft.7/11/2024Arce Ct642$555,5002,233 Sq.Ft.2/21/2017Archer Ct543$612,0002,784 Sq.Ft.8/10/2021Archer Dr1142$586,6252,421 Sq.Ft.3/21/2024Archer Pl1443$598,7142,658 Sq.Ft.4/28/2022Archery Ct442$318,5001,707 Sq.Ft.9/15/2015Archery Dr942$327,1251,936 Sq.Ft.11/29/2021Arch Rd1543$521,5712,477 Sq.Ft.7/8/2024Ardmore Ave6042$325,5711,591 Sq.Ft.7/12/2024Ardmore Cir842$329,3751,471 Sq.Ft.5/16/2023Arena Ct1443$570,1432,866 Sq.Ft.8/30/2023Argyll St2042$458,7066,127 Sq.Ft.6/16/2023Ark Royal Rd1533$416,4672,139 Sq.Ft.11/18/2024Arlean Dr1042$442,5002,177 Sq.Ft.12/19/2017Arlington Ave342$286,3331,450 Sq.Ft.7/5/2022Arlo Ct1043$531,8892,882 Sq.Ft.6/15/2020Armada Ct653$533,0002,889 Sq.Ft.11/10/2021Armada Dr5232$425,9602,102 Sq.Ft.4/8/2025Armentrout Ct1132$341,3641,554 Sq.Ft.7/15/2021Armor Ln1232$350,5451,763 Sq.Ft.8/8/2016Armstrong Dr1N/AN/AN/AN/A2/28/2025Armstrong Ln2N/AN/AN/A7,682 Sq.Ft.2/28/2025Arnold Ct343$566,6672,627 Sq.Ft.1/11/2019Arondale Cres2932$393,6671,520 Sq.Ft.5/16/2025Arondale Ct732$372,5711,419 Sq.Ft.3/28/2022Arrowhead Ct653$591,0002,924 Sq.Ft.9/14/2022Arrowleaf Ct943$669,3332,852 Sq.Ft.5/13/2025Arrowleaf Way2053$672,4383,059 Sq.Ft.5/16/2025Arthurs Ct6231$433,1771,275 Sq.Ft.9/11/2024Artisan Ave4153$595,0322,834 Sq.Ft.6/26/2024Artis Ave12N/A2$341,9001,344 Sq.Ft.4/29/2022Arundel Ln1532$247,9331,590 Sq.Ft.1/16/2025Asbury Ct543$634,0002,697 Sq.Ft.6/4/2025Ashburn Ct943$627,5562,712 Sq.Ft.9/27/2023Ashforth Way2543$621,9572,816 Sq.Ft.5/16/2025Ash Hill Ct343$516,0002,464 Sq.Ft.9/23/2014Ash Hill Lndg1742$482,3132,201 Sq.Ft.6/27/2024Ashland Dr2532$344,2001,732 Sq.Ft.8/5/2024Ashlar Ln2043$701,5293,116 Sq.Ft.2/28/2025Ashley Caroline Ct642$403,2001,760 Sq.Ft.9/9/2022Ashley Rd2632$450,9601,931 Sq.Ft.4/7/2025Ash Pine Cv432$345,5001,362 Sq.Ft.8/7/2024Ashton St1132$291,8181,622 Sq.Ft.5/31/2024Ashwell Way453$674,5002,719 Sq.Ft.6/8/2023Ashwood Dr1843$503,0562,617 Sq.Ft.7/26/2024Askew Rd1232$387,0001,592 Sq.Ft.1/11/2024Aspen Arch442$510,5002,351 Sq.Ft.11/6/2024Aspen Forest Ct454$694,5003,206 Sq.Ft.5/19/2023Aspinock St742$539,0002,345 Sq.Ft.6/29/2015Aston Pl843$586,5712,711 Sq.Ft.6/21/2023Astor Way432$309,7501,778 Sq.Ft.3/8/2021Astra Ln1133$297,4001,379 Sq.Ft.6/23/2023Asuza St3533$459,1822,125 Sq.Ft.5/14/2025Atamasco St2423$290,2171,464 Sq.Ft.5/22/2025Athens Ct1342$368,7271,773 Sq.Ft.5/2/2022Atkinson Mews333$380,6671,800 Sq.Ft.11/3/2023Atlantic Ave14032$314,0092,641 Sq.Ft.12/31/2024Attwick Ct1423$235,0711,254 Sq.Ft.12/9/2024Aubrey Ct443$622,0002,705 Sq.Ft.12/23/2022Auburn Hill Ct153$717,0002,895 Sq.Ft.12/8/2022Auburn Hill Dr6653$645,6382,672 Sq.Ft.4/14/2025Audubon Cir654$795,5003,826 Sq.Ft.8/28/2024Aundre Ct632$327,3331,129 Sq.Ft.8/6/2021Austenwood Ct1242$557,7272,481 Sq.Ft.8/30/2021Austin Dr3842$480,2862,158 Sq.Ft.5/8/2025Autumn Green Ln1433$381,1541,970 Sq.Ft.4/28/2025Autumn Oaks Dr842$509,0001,946 Sq.Ft.3/1/2019Ava Ct553$645,6673,092 Sq.Ft.11/22/2021Avalon Ave2231$269,4551,153 Sq.Ft.4/14/2025Avast Way1333$418,6672,016 Sq.Ft.3/25/2024Avebury Way842$429,4291,833 Sq.Ft.4/16/2025Averill Dr3143$603,9236,429 Sq.Ft.6/3/2024Avery Ct843$531,7502,412 Sq.Ft.4/10/2024904 Stern WayChesapeake, VA 23323
Estimated Value $445,000
Living Area 2,432 SqFt
Beds 3
Baths 3.5
Year Built 2020
Property Type Condominium
Ownership Type Multiple
APN 0354003001980
Neighborhood Deep Creek
School District Chesapeake City Public Schools
1129 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
926 Avast WayChesapeake, VA 23323
Estimated Value $377,000
Living Area 1,720 SqFt
Beds 3
Baths 2.5
Year Built 2018
Property Type Condominium
Ownership Type Individual
APN 0354003000600
Neighborhood Deep Creek
School District Chesapeake City Public Schools
1649 Shipyard RdChesapeake, VA 23323
Estimated Value $421,000
Living Area 1,716 SqFt
Beds 4
Baths 2.5
Year Built 2010
Property Type Single Family
Ownership Type Individual
APN 0350000000210
Neighborhood Deep Creek
School District Chesapeake City Public Schools
1620 Burson DrChesapeake, VA 23323
Estimated Value $772,000
Living Area 3,381 SqFt
Beds 3
Baths 3
Year Built 2015
Property Type Single Family
Ownership Type Related
APN 0344002003961
Neighborhood Deep Creek
School District Chesapeake City Public Schools
4126 4th StChesapeake, VA 23324
Estimated Value $267,000
Living Area 1,586 SqFt
Beds 2
Baths 1.5
Year Built 1946
Property Type Single Family
Ownership Type Individual
APN 1600000000250
Neighborhood South Norfolk
School District Chesapeake City Public Schools
807 Shenandoah River RdChesapeake, VA 23320
Estimated Value $279,000
Living Area 1,350 SqFt
Beds 2
Baths 2
Year Built 1990
Property Type Condominium
Ownership Type Individual
APN 0367003000790
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1205 Bramblewood CtChesapeake, VA 23323
Estimated Value $334,000
Living Area 425 SqFt
Beds 1
Baths 1
Year Built 1980
Property Type Single Family
Ownership Type Individual
APN 0343013000100
Neighborhood Deep Creek
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
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
1008 Roxbury CtChesapeake, VA 23320
Estimated Value $468,000
Living Area 2,658 SqFt
Beds 4
Baths 3.5
Year Built 2007
Property Type Single Family
Ownership Type Individual
APN 0361015000260
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
1002 Godwin AveChesapeake, VA 23324
Estimated Value $364,000
Living Area 1,924 SqFt
Beds 4
Baths 2.5
Year Built 2013
Property Type Single Family
Ownership Type Individual
APN 1520000002620
Neighborhood South Norfolk
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
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
4177 Williamson StChesapeake, VA 23324
Estimated Value $310,000
Living Area 1,680 SqFt
Beds 4
Baths 2.5
Year Built 2013
Property Type Single Family
Ownership Type Individual
APN 1600000002351
Neighborhood South Norfolk
School District Chesapeake City Public Schools