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
Bridle Ct842$447,3752,089 Sq.Ft.9/27/2024Brier Cliff Cres2543$535,1302,479 Sq.Ft.4/28/2025Brigade Dr1442$471,0001,864 Sq.Ft.7/9/2024Brigantine Ct3932$256,0791,139 Sq.Ft.3/6/2025Brightleaf Pl2343$463,1762,069 Sq.Ft.4/16/2025Brighton Ln2332$271,3481,662 Sq.Ft.6/3/2024Bright Red Run3033$404,7861,794 Sq.Ft.5/2/2023Brinn Quay243$559,0002,308 Sq.Ft.12/11/2017Brinsmayd Arch453$717,2503,747 Sq.Ft.7/14/2022Brisa Ct5822$294,2681,416 Sq.Ft.8/2/2023Brisa Dr7432$302,6941,435 Sq.Ft.3/28/2025Bristlewood Ct332$409,3331,620 Sq.Ft.4/19/2021Bristol Cir1432$265,1431,456 Sq.Ft.12/9/2024British Oak Ct532$392,7501,851 Sq.Ft.9/20/2021Briton Ln2243$652,6842,600 Sq.Ft.5/20/2025Brittany Way2443$472,9582,594 Sq.Ft.5/29/2025Britwell Dr1732$438,7501,932 Sq.Ft.5/30/2025Broad Bend Cir4433$467,8782,260 Sq.Ft.3/5/2025Broadleaf Xing1143$454,1002,083 Sq.Ft.4/15/2025Broadmoor Ave3232$329,2632,730 Sq.Ft.5/10/2024Broadmoor Way1031$320,7001,250 Sq.Ft.3/31/2022Broadnax Cir3542$399,2501,682 Sq.Ft.5/29/2025Broadnax Dr1142$410,0001,785 Sq.Ft.4/15/2025Broad Reach Rd732$440,8572,020 Sq.Ft.8/2/2021Broad St2031$277,4126,072 Sq.Ft.6/29/2021Broadwater Ct442$458,6671,839 Sq.Ft.8/14/2023Broadwater Dr1932$425,8751,715 Sq.Ft.10/4/2024Broadwinsor Cres3243$583,0772,619 Sq.Ft.1/13/2025Brock Ct343$643,0002,610 Sq.Ft.9/3/2021Brockenbraugh Rd1842$447,6672,066 Sq.Ft.9/25/2024Bromay St1333$392,00040,578 Sq.Ft.8/24/2023Brookcrest Arch943$526,4442,647 Sq.Ft.2/18/2025Brookedale Ct1142$549,1002,241 Sq.Ft.2/11/2022Brookfield Ln1N/AN/AN/A1,684 Sq.Ft.10/14/2010Brookhaven Ct444$802,0003,955 Sq.Ft.1/4/2023Brookland Dr1N/AN/AN/A142,656 Sq.Ft.N/ABrookmont Ln1443$768,6673,751 Sq.Ft.12/31/2022Brookrun Chase1123$345,4551,493 Sq.Ft.10/16/2023Brookshire Dr1N/AN/AN/A2,434 Sq.Ft.N/ABrookside Arch1243$706,7503,284 Sq.Ft.6/24/2024Brookside Ct453$722,0003,530 Sq.Ft.5/22/2023Brookside Lndg2132$362,5291,607 Sq.Ft.5/12/2025Brook Stone Dr2442$420,6251,934 Sq.Ft.6/26/2024Brougham Ct943$564,4442,522 Sq.Ft.6/21/2024Broward Way1253$686,4173,314 Sq.Ft.5/3/2024Browning Cir1043$467,9002,436 Sq.Ft.10/21/2024Brown Rd1832$402,2351,865 Sq.Ft.3/14/2021Bruce Rd3343$668,31611,468 Sq.Ft.3/11/2025Bruce Sta3943$716,0793,504 Sq.Ft.1/14/2025Bruce Station Ct543$691,0002,995 Sq.Ft.4/18/2024Bruin Dr8032$334,7301,803 Sq.Ft.12/18/2024Bruin Pl1N/AN/AN/A285,162 Sq.Ft.N/ABruno Dr3932$324,2221,601 Sq.Ft.9/12/2024Brunswick Ct1142$469,2732,198 Sq.Ft.3/11/2022Bruton Ct14N/AN/AN/A5,620 Sq.Ft.1/15/2024Bryan Ct633$411,0002,228 Sq.Ft.7/24/2023Bryant Dr242$480,0001,990 Sq.Ft.6/29/2021Bryson Arch1353$623,0913,117 Sq.Ft.5/26/2021B St7242$260,0732,282 Sq.Ft.3/28/2025Buchanan St732$251,0001,288 Sq.Ft.3/17/2023Buckingham Dr1543$461,2862,245 Sq.Ft.7/6/2022Buckland St532$325,4002,205 Sq.Ft.3/21/2025Buck St232$333,5001,610 Sq.Ft.4/20/2001Buckthorn Ct842$402,7501,859 Sq.Ft.11/17/2022Bud Dr432N/A7,135 Sq.Ft.7/13/2007Buddy Ct442$495,5002,115 Sq.Ft.7/13/2023Buell St13N/AN/AN/A92,149 Sq.Ft.10/15/2020Bufflehead Dr1N/AN/AN/A100 Sq.Ft.N/ABuff St432$292,0001,236 Sq.Ft.8/1/2022Buford Ct1532$378,2311,381 Sq.Ft.4/29/2025Bugle Dr11032$367,2291,870 Sq.Ft.5/27/2025Bulldog Dr2N/AN/AN/A20,810 Sq.Ft.5/1/2024Bulrush Ct1042$464,9002,109 Sq.Ft.2/21/2023Bunch Walnuts Rd9133$678,7742,557 Sq.Ft.4/30/2025Bunker Ridge Arch2122$300,2861,449 Sq.Ft.11/21/2024Burdett St1543$718,4292,868 Sq.Ft.9/26/2024Burfoot St932$306,2221,685 Sq.Ft.3/18/2025Burford Ln1333$338,1541,771 Sq.Ft.7/16/2024Burgess Ct1043$645,3332,725 Sq.Ft.7/29/2024Burkett Ct742$490,8571,917 Sq.Ft.10/17/2018Burns Ct532$331,0001,446 Sq.Ft.4/13/2023Burnside Pl1142$420,7002,497 Sq.Ft.2/28/2024Burns St1842$338,6432,346 Sq.Ft.10/26/2023Burr Ct432$345,0001,717 Sq.Ft.9/8/2020Burrow Ave2631$243,0001,666 Sq.Ft.9/27/2024Burrowin Dr1854$699,3333,829 Sq.Ft.1/25/2023Burson Dr12143$535,2042,455 Sq.Ft.3/6/2025Burson Rd1N/AN/AN/AN/AN/ABurton Ct443$524,5002,179 Sq.Ft.11/14/2023Burton Pl943$560,0002,482 Sq.Ft.10/24/2024Business Center Dr21N/AN/AN/A29,388 Sq.Ft.6/21/2024Business Park Dr11N/AN/AN/A6,434 Sq.Ft.8/25/2023Buskey Rd2943$719,8262,495 Sq.Ft.8/30/2024Bute St1842$382,3332,033 Sq.Ft.6/7/2023Butler St39N/A1N/A2,854 Sq.Ft.4/15/2024Butrico Rd1532$306,4001,323 Sq.Ft.8/20/2024Butterfly Dr5143$567,6882,525 Sq.Ft.1/29/2025Butterwick Ct2223$231,6361,254 Sq.Ft.2/12/2024Butts Station Rd7532$439,8311,927 Sq.Ft.8/13/2024Butt St1132$248,3001,336 Sq.Ft.9/3/20241404 Earle AveChesapeake, VA 23324
Estimated Value $287,000
Living Area 1,828 SqFt
Beds 3
Baths 2
Year Built 1948
Property Type Single Family
Ownership Type Individual
APN 1590000003460
Neighborhood South Norfolk
School District Chesapeake City Public Schools
504 Rosewood TerChesapeake, VA 23320
Estimated Value $412,000
Living Area 1,629 SqFt
Beds 3
Baths 1.5
Year Built 1966
Property Type Single Family
Ownership Type Related
APN 0361008000890
Neighborhood Rivercrest
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
320 Esplanade PlChesapeake, VA 23320
Estimated Value $311,000
Living Area 1,352 SqFt
Beds 2
Baths 2.5
Year Built 1993
Property Type Townhouse
Ownership Type Related
APN 0367008000150
Neighborhood Rivercrest
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
4162 Reid StChesapeake, VA 23324
Estimated Value $282,000
Living Area 1,330 SqFt
Beds 3
Baths 2
Year Built 1955
Property Type Single Family
Ownership Type Individual
APN 1600000001510
Neighborhood South Norfolk
School District Chesapeake City Public Schools
4136 2nd StChesapeake, VA 23324
Estimated Value $238,000
Living Area 1,040 SqFt
Beds 3
Baths 2
Year Built 1991
Property Type Single Family
Ownership Type Corporate
APN 1590000002800
Neighborhood South Norfolk
School District Chesapeake City Public Schools
4305 Pickney LnChesapeake, VA 23324
Estimated Value $321,000
Living Area 1,720 SqFt
Beds 3
Baths 2.5
Year Built 2018
Property Type Condominium
Ownership Type Related
APN 1580001000710
Neighborhood South Norfolk
School District Chesapeake City Public Schools
817 Englewood DrChesapeake, VA 23320
Estimated Value $360,000
Living Area 1,649 SqFt
Beds 3
Baths 2
Year Built 1966
Property Type Single Family
Ownership Type Individual
APN 0361008000960
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1233 Marge DrChesapeake, VA 23320
Estimated Value $302,000
Living Area 1,336 SqFt
Beds 3
Baths 1.5
Year Built 1975
Property Type Single Family
Ownership Type Individual
APN 0272001000440
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1048 Livingston AveChesapeake, VA 23324
Estimated Value $318,000
Living Area 1,623 SqFt
Beds 3
Baths 2.5
Year Built 2006
Property Type Single Family
Ownership Type Trust
APN 1510000001190
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
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
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
1337 Dominion Lakes BlvdChesapeake, VA 23320
Estimated Value $625,000
Living Area 3,028 SqFt
Beds 5
Baths 2.5
Year Built 2002
Property Type Single Family
Ownership Type Related
APN 0352001000250
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1616 Woodbriar LnChesapeake, VA 23323
Estimated Value $303,000
Living Area 1,400 SqFt
Beds 4
Baths 2
Year Built 1983
Property Type Single Family
Ownership Type Multiple
APN 0343017000220
Neighborhood Deep Creek
School District Chesapeake City Public Schools