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
Avery Trce442$518,7502,043 Sq.Ft.4/15/2021Avondale Ct1242$368,0002,119 Sq.Ft.12/2/2022Avonlea Ct964$848,2864,431 Sq.Ft.10/4/2022Avonlea Dr1754$794,4123,747 Sq.Ft.7/20/2022Avonlea Pointe1354$849,6364,254 Sq.Ft.3/18/2024Avon Rd1542$426,7331,716 Sq.Ft.5/31/2018Aylesbury Dr1942$457,1051,718 Sq.Ft.4/22/2020Ayrshire Ct443$614,2502,816 Sq.Ft.3/18/2025Azalea Ct343$535,6672,499 Sq.Ft.8/18/2022Back Rd1942$523,6672,305 Sq.Ft.2/28/2024Backwoods Rd2632$602,0002,281 Sq.Ft.3/19/2022Baffy Loop4954$898,0434,099 Sq.Ft.3/19/2025Bahama Way1953$667,1113,268 Sq.Ft.1/7/2025Bailey Ln432$392,7501,461 Sq.Ft.4/30/2025Bainbridge Blvd34332$293,53812,071 Sq.Ft.5/12/2025Bainbridge Pt3N/AN/AN/AN/A12/15/1998Bakerloo Ct343$589,3332,661 Sq.Ft.7/18/2018Baker Loop2843$641,5602,765 Sq.Ft.4/5/2024Balboa Cres1043$463,4442,192 Sq.Ft.6/20/2024Bald Cypress Ct843$613,7503,254 Sq.Ft.4/29/2022Baldwin Dr5633$296,7171,314 Sq.Ft.4/7/2025Balford Ln1532$352,2141,452 Sq.Ft.9/15/2022Balladeer Ct643$623,0002,824 Sq.Ft.10/28/2020Ballahack Rd38032$613,4132,330 Sq.Ft.5/30/2025Ballance Ct453$493,7502,782 Sq.Ft.9/26/2022Ballast Ct853$657,8573,655 Sq.Ft.6/12/2023Ballast Ln1153$646,2003,494 Sq.Ft.8/10/2018Ballentine Rd7N/AN/AN/AN/AN/ABall St642$320,6671,616 Sq.Ft.1/3/2020Balmoral Ln545$1,674,2504,801 Sq.Ft.8/19/2024Bancroft Rd4753$761,7563,358 Sq.Ft.5/5/2025Baneberry Way1753$656,6672,917 Sq.Ft.7/29/2024Banff Ct2753$656,1433,066 Sq.Ft.6/6/2024Bangor Cres8032$228,7381,373 Sq.Ft.3/25/2025Bangor Ct932$254,4441,202 Sq.Ft.4/25/2025Bangor Dr3032$308,4001,310 Sq.Ft.2/18/2025Bankbury Way1945$1,738,7785,372 Sq.Ft.10/4/2024Banks St1131N/A1,186 Sq.Ft.1/22/2021Bannister St2431$254,0001,420 Sq.Ft.4/23/2018Barbara Ct1943$612,2782,526 Sq.Ft.12/16/2024Barbury Arch942$441,2221,854 Sq.Ft.12/15/2020Barcelona Cir342$522,0002,273 Sq.Ft.10/31/2022Barcelona Ct443$541,0002,427 Sq.Ft.1/3/2017Barcelona Dr4243$553,3752,419 Sq.Ft.9/19/2024Barger St1632$319,8751,343 Sq.Ft.5/26/2023Bar Harbor Ct543$406,2002,165 Sq.Ft.5/28/2025Barkadeer Cv3933$426,8822,136 Sq.Ft.9/20/2024Barksdale Rd1242$414,7501,882 Sq.Ft.2/24/2025Barlingame Pl1N/AN/AN/A163,344 Sq.Ft.N/ABarnes Rd12N/AN/AN/A64,390 Sq.Ft.4/28/2010Barn Owl Ln1053$624,8893,096 Sq.Ft.10/29/2018Barn Swallow Ct443$562,2502,664 Sq.Ft.6/4/2024Barn Swallow Dr3943$563,2822,823 Sq.Ft.3/20/2024Barn Way3342$396,5481,911 Sq.Ft.1/4/2025Barnwell Ln642$412,3331,960 Sq.Ft.10/28/2024Baron Ct1031$282,0001,157 Sq.Ft.4/3/2023Barque Pl1133$399,5561,850 Sq.Ft.11/18/2024Barred Owl Ln2023$289,7001,464 Sq.Ft.12/10/2024Barrington Ct1042$518,3332,142 Sq.Ft.11/11/2024Bartell Ct442$436,2501,886 Sq.Ft.N/ABartell Dr7543$496,1112,271 Sq.Ft.9/17/2024Bartlett Dr533$503,6002,452 Sq.Ft.3/28/2019Barwick Ct1623$235,8751,254 Sq.Ft.3/14/2025Basing Ct443$527,7502,334 Sq.Ft.4/4/2022Basin Rd3N/AN/AN/A69,241 Sq.Ft.12/16/2024Basnight Ct1422$303,9291,526 Sq.Ft.12/23/2024Bassett St931$294,6671,276 Sq.Ft.12/1/2021Bass Ln1N/AN/AN/AN/AN/ABasswood Ct4432$263,2271,246 Sq.Ft.3/27/2025Bastian Ct742$497,0002,189 Sq.Ft.8/25/2021Bateau Lndg2453$694,1253,625 Sq.Ft.6/17/2022Battery Cir332$459,6672,128 Sq.Ft.4/15/2025Battery Park Rd6832$336,8771,689 Sq.Ft.2/11/2025Battlefield Blvd59432$453,4517,617 Sq.Ft.5/30/2025Battlefield Cmns1N/AN/AN/AN/AN/ABattlefield Woods Ct1N/AN/AN/A1,508 Sq.Ft.10/28/2010Battle St246N/AN/A$453,959N/A2/17/2025Batton Door Pl743$521,7142,587 Sq.Ft.10/28/2021Baugher Ave3331$257,5331,196 Sq.Ft.10/17/2024Baum Rd2543$677,7082,647 Sq.Ft.2/21/2024Bayberry Ct2742$452,2222,222 Sq.Ft.8/5/2024Bayberry Pl2142$457,6672,265 Sq.Ft.5/24/2022Bay Cres1843$333,9442,113 Sq.Ft.1/25/2025Baydon Ln5742$549,0182,273 Sq.Ft.1/27/2025Bayford Ct643$555,3333,060 Sq.Ft.8/23/2017Bayhaven Ct442$424,0001,771 Sq.Ft.5/12/2025Bay Laurel Ct543$575,5002,932 Sq.Ft.5/24/2021Baylor Ct1242$343,8003,766 Sq.Ft.2/13/2024Bay Oak Ct932$381,2221,766 Sq.Ft.8/7/2024Bay Oak Dr2242$385,9001,732 Sq.Ft.2/21/2025Baywater Ct342$581,3332,404 Sq.Ft.4/2/2018Baywood Trl3742$384,2701,701 Sq.Ft.3/18/2025B Chandler Dr132$308,0001,356 Sq.Ft.4/1/2022Beachstone Quay1053$691,4442,975 Sq.Ft.5/25/2023Beacon Hill Pl543$704,2502,791 Sq.Ft.4/14/2022Beacon Hill Rd1043$701,6673,448 Sq.Ft.7/14/2022Beacon Key Ct243$712,5002,392 Sq.Ft.8/26/2015Beagle Gap Ct653$635,6672,662 Sq.Ft.11/3/2023Bear Creek Ln2363$562,0533,242 Sq.Ft.4/6/2023Beardsly Ct543$635,8002,850 Sq.Ft.3/19/2019309 Paperbark TrlChesapeake, VA 23323
Estimated Value $369,000
Living Area 1,610 SqFt
Beds 3
Baths 2
Year Built 1998
Property Type Single Family
Ownership Type Multiple
APN 0343023000480
Neighborhood Deep Creek
School District Chesapeake City Public Schools
1727 Faulk StChesapeake, VA 23323
Estimated Value $281,000
Living Area 1,424 SqFt
Beds 3
Baths 2.5
Year Built 2004
Property Type Single Family
Ownership Type Individual
APN 0261002000150
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
800 Rivanna River ReachChesapeake, VA 23320
Estimated Value $293,000
Living Area 1,434 SqFt
Beds 2
Baths 1.5
Year Built 1989
Property Type Condominium
Ownership Type Individual
APN 0367003000140
Neighborhood Rivercrest
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
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
838 Rivanna River ReachChesapeake, VA 23320
Estimated Value $283,000
Living Area 1,350 SqFt
Beds 2
Baths 2
Year Built 1989
Property Type Condominium
Ownership Type Individual
APN 0367003000190
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1042 Livingston AveChesapeake, VA 23324
Estimated Value $468,000
Living Area 2,945 SqFt
Beds 4
Baths 2.5
Year Built 2006
Property Type Single Family
Ownership Type Corporate
APN 1510000001170
Neighborhood South Norfolk
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
1119 Railroad AveChesapeake, VA 23324
Estimated Value $239,000
Living Area 1,197 SqFt
Beds 3
Baths 2
Year Built 1960
Property Type Single Family
Ownership Type Individual
APN 1660000000060
Neighborhood South Norfolk
School District Chesapeake City Public Schools
1207 Basswood CtChesapeake, VA 23320
Estimated Value $273,000
Living Area 1,264 SqFt
Beds 3
Baths 2.5
Year Built 1987
Property Type Townhouse
Ownership Type Individual
APN 0366008000410
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1210 Freeman AveChesapeake, VA 23324
Estimated Value $231,000
Living Area 968 SqFt
Beds 2
Baths 1
Year Built 1940
Property Type Single Family
Ownership Type Corporate
APN 1590000001790
Neighborhood South Norfolk
School District Chesapeake City Public Schools
4123 Everett St #BChesapeake, VA 23324
Estimated Value $377,000
Living Area 2,164 SqFt
Beds 5
Baths 3
Year Built 2017
Property Type Single Family
Ownership Type Related
APN 1600000001761
Neighborhood South Norfolk
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
573 Marc Smiley RdChesapeake, VA 23324
Estimated Value $300,000
Living Area 1,442 SqFt
Beds 2
Baths 2.5
Year Built 2016
Property Type Condominium
Ownership Type Individual
APN 1580001001350
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