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
Golfview Dr453$540,3332,265 Sq.Ft.7/14/2017Goodman St2032$336,3161,687 Sq.Ft.9/18/2024Goose Creek Ct543$526,0002,507 Sq.Ft.8/17/2020Goose Creek Flyway1853$583,2733,435 Sq.Ft.8/20/2024Goshawk Dr942$538,6672,468 Sq.Ft.5/10/2023Gould Ave832$330,3331,810 Sq.Ft.4/23/2025Grace St1242$435,6001,759 Sq.Ft.7/26/2024Gracie Rd3232$304,3441,439 Sq.Ft.6/12/2024Grady Cres2N/AN/AN/A32,580 Sq.Ft.N/AGrady St2N/AN/AN/A5,251 Sq.Ft.N/AGrain Way1742$410,1431,869 Sq.Ft.5/20/2022Granada Dr3943$575,2892,710 Sq.Ft.3/6/2025Grand Isle Dr7043$519,6532,780 Sq.Ft.1/7/2025Grandy Ct2032$382,8951,465 Sq.Ft.1/4/2023Grandy Dr1942$485,7221,994 Sq.Ft.9/20/2024Grandy Rd532$356,7501,115 Sq.Ft.1/3/2024Grant Ct543$521,6002,955 Sq.Ft.12/20/2024Grantham Ln4243$567,0732,378 Sq.Ft.5/22/2025Granton Ter3033$414,2001,881 Sq.Ft.4/29/2025Grant St3342$367,1151,920 Sq.Ft.5/15/2025Grape Ln743$530,4292,665 Sq.Ft.5/29/2024Graphite Trl4053$720,5483,081 Sq.Ft.1/16/2025Grassfield Pkwy11N/AN/AN/A35,775 Sq.Ft.3/25/2025Grassfield Rd331$341,0001,578 Sq.Ft.11/30/2021Gratton St1632$313,3131,246 Sq.Ft.2/18/2025Graver Ln2053$647,2502,869 Sq.Ft.5/12/2025Gray Rock Rd1544$1,057,3574,254 Sq.Ft.1/7/2022Grayson Way643$517,2002,545 Sq.Ft.9/7/2021Great Bridge Blvd15332$337,2345,967 Sq.Ft.6/3/2025Great Heron Ct943$621,4442,788 Sq.Ft.6/8/2017Great Marsh Ave4943$517,2682,504 Sq.Ft.5/14/2025Great Marsh Cir443$641,0003,057 Sq.Ft.4/12/2021Great Oak Ct642$353,5001,619 Sq.Ft.5/19/2025Grebe Ct9N/AN/AN/AN/A3/5/1999Greenbrier Cir45N/A1N/A18,871 Sq.Ft.2/6/2025Greenbrier Pkwy49N/AN/AN/A26,930 Sq.Ft.7/18/2023Greenbrier Rd532$367,6671,332 Sq.Ft.5/28/2020Greendell Rd4732$343,0221,473 Sq.Ft.2/18/2025Greenfield Ln4354$805,5003,511 Sq.Ft.7/19/2024Greengable Way4154$823,9744,089 Sq.Ft.1/17/2025Greenleaf Dr1642$448,9382,284 Sq.Ft.2/9/2021Green Meadow Dr1333$387,4621,983 Sq.Ft.8/20/2024Greenmoor Ct253$793,0002,842 Sq.Ft.9/18/2017Green Oaks Ct243$561,0002,138 Sq.Ft.1/17/2020Green Point Dr132$353,0001,451 Sq.Ft.5/29/2025Green Sea Trl4243$577,5952,713 Sq.Ft.4/16/2024Greens Edge Ct364$850,3334,464 Sq.Ft.8/28/2023Greens Edge Dr2954$848,2593,982 Sq.Ft.2/13/2025Greenspring Ct742$490,1431,930 Sq.Ft.9/3/2021Green Tree Cir1N/AN/AN/A190,194 Sq.Ft.12/15/2021Green Tree Rd932$329,00023,410 Sq.Ft.3/27/2019Greenview Rd2642$466,7602,275 Sq.Ft.10/1/2024Greenway Dr2332$454,4291,753 Sq.Ft.4/15/2024Greenwell Ln533$376,6001,752 Sq.Ft.10/22/2021Greenwing Ct1043$541,5563,255 Sq.Ft.6/3/2021Greenwing Dr2843$488,8802,807 Sq.Ft.10/31/2024Greenwood Rd2332$432,5222,102 Sq.Ft.3/26/2025Greer St1432$279,8331,509 Sq.Ft.5/29/2025Gregg St4442$362,5251,935 Sq.Ft.5/23/2025Grenadier Ct842$481,0001,893 Sq.Ft.11/24/2021Grenadier Dr1242$469,1671,868 Sq.Ft.1/31/2025Gresham Way953$626,4293,258 Sq.Ft.6/1/2023Gress Arch1043$725,8752,843 Sq.Ft.4/4/2024Gretna Ct243$517,5002,600 Sq.Ft.5/29/2025Grey Fox Ct842$412,0001,815 Sq.Ft.5/23/2025Greystone Ln2253$808,5504,064 Sq.Ft.5/15/2024Grimes Way533$343,8001,963 Sq.Ft.5/6/2024Grizzly Way1N/AN/AN/A338,400 Sq.Ft.11/26/2003Grover Ct954$761,5714,030 Sq.Ft.2/14/2022Gruen St2242$365,0001,721 Sq.Ft.4/6/2023Guadal Ct10N/AN/AN/AN/AN/AGuenevere Ct942$328,3331,858 Sq.Ft.8/18/2023Guenevere Dr6742$329,2261,773 Sq.Ft.4/17/2025Guerriere St363$314,00012,880 Sq.Ft.N/AGuildford Mews623$314,1671,624 Sq.Ft.5/18/2022Guisborne Ct543$587,2002,483 Sq.Ft.3/11/2022Gulfwind Rd1543$456,6432,188 Sq.Ft.2/14/2022Gum Ct853$434,3334,392 Sq.Ft.4/26/2023Gum Rd6242$484,8956,892 Sq.Ft.5/2/2025Gum Tree Ct332$258,5002,143 Sq.Ft.2/23/2024Gunston Bridge Ct1032$431,5561,884 Sq.Ft.1/27/2025Gunston Ct864$874,2504,443 Sq.Ft.6/30/2016Gust Ln4242$345,2812,448 Sq.Ft.5/28/2025Guynn Ave2531$307,2501,396 Sq.Ft.3/13/2025Gwaltney Ct954$666,7783,374 Sq.Ft.9/4/2024Habitat Xing2344$718,5003,148 Sq.Ft.4/9/2024Hadleybrook Dr4223$279,2751,352 Sq.Ft.4/15/2024Hadley Ct743$536,1432,924 Sq.Ft.11/29/2022Hagenspring Rd2143$516,9472,470 Sq.Ft.3/24/2025Hailey Ct1132$330,9091,546 Sq.Ft.4/27/2012Hails Ln643$588,8332,645 Sq.Ft.5/18/2022Haledon Rd6632$323,4221,377 Sq.Ft.6/21/2023Half Hitch St343$369,5002,301 Sq.Ft.7/13/2021Halifax Ln4N/AN/AN/A372,850 Sq.Ft.1/28/2025Hallbridge Dr1332$435,0001,794 Sq.Ft.12/30/2024Hall Dr3532$423,3431,859 Sq.Ft.11/27/2024Hallmark Way4543$781,0003,330 Sq.Ft.3/31/2025Halsey St4031$271,6001,296 Sq.Ft.3/10/2025Halstead Rd2N/AN/A$430,000N/A4/28/2008Halter Arch543$486,6002,750 Sq.Ft.1/16/2007312 Outlaw StChesapeake, VA 23320
Estimated Value $410,000
Living Area 2,501 SqFt
Beds 4
Baths 2.5
Year Built 2002
Property Type Single Family
Ownership Type Individual
APN 0351004001130
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
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
2308 Willow Point ArchChesapeake, VA 23320
Estimated Value $239,000
Living Area 1,171 SqFt
Beds 2
Baths 2
Year Built 1999
Property Type Condominium
Ownership Type Individual
APN 0367013000040
Neighborhood Rivercrest
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
103 Ford StChesapeake, VA 23323
Estimated Value $348,000
Living Area 1,972 SqFt
Beds 4
Baths 3
Year Built 2018
Property Type Single Family
Ownership Type Multiple
APN 0261002000780
Neighborhood Deep Creek
School District Chesapeake City Public Schools
1401 Glendale AveChesapeake, VA 23323
Estimated Value $311,000
Living Area 1,360 SqFt
Beds 3
Baths 2
Year Built 1977
Property Type Single Family
Ownership Type Individual
APN 0255001002870
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
428 Cobblewood ArchChesapeake, VA 23320
Estimated Value $255,000
Living Area 1,046 SqFt
Beds 3
Baths 2
Year Built 1987
Property Type Single Family
Ownership Type Individual
APN 0366006000230
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1235 Woods WayChesapeake, VA 23323
Estimated Value $366,000
Living Area 1,875 SqFt
Beds 3
Baths 2.5
Year Built 1999
Property Type Single Family
Ownership Type Related
APN 0343023001190
Neighborhood Deep Creek
School District Chesapeake City Public Schools
1204 Corden AveChesapeake, VA 23324
Estimated Value $243,000
Living Area 1,645 SqFt
Beds 3
Baths 1
Year Built 1948
Property Type Single Family
Ownership Type Individual
APN 1590000001070
Neighborhood South Norfolk
School District Chesapeake City Public Schools
4374 Pickney LnChesapeake, VA 23324
Estimated Value $327,000
Living Area 1,760 SqFt
Beds 3
Baths 2.5
Year Built 2016
Property Type Condominium
Ownership Type Individual
APN 1580001001170
Neighborhood South Norfolk
School District Chesapeake City Public Schools
1819 Sunsprite LoopChesapeake, VA 23323
Estimated Value $612,000
Living Area 2,924 SqFt
Beds 4
Baths 2.5
Year Built 2007
Property Type Single Family
Ownership Type Related
APN 0354001000110
Neighborhood Deep Creek
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
1412 Anthony DrChesapeake, VA 23320
Estimated Value $333,000
Living Area 1,500 SqFt
Beds 3
Baths 2.5
Year Built 1984
Property Type Single Family
Ownership Type Individual
APN 0272001001390
Neighborhood Rivercrest
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