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
Frost Flower Ct1242$409,4171,724 Sq.Ft.4/17/2023Frosty Rd2032$319,7001,391 Sq.Ft.4/22/2024Fryar Pl643$652,8333,284 Sq.Ft.7/6/2018Fulcrum Ct653$576,0003,558 Sq.Ft.12/18/2019Fulton Ln553$642,0002,839 Sq.Ft.3/16/2023Furnace Rd2132$312,9051,485 Sq.Ft.3/13/2024Gabion Way5833$437,8112,248 Sq.Ft.5/21/2025Gable Way943$553,3332,564 Sq.Ft.6/29/2022Gadwall Ct11N/AN/AN/AN/AN/AGaff Rd1232$296,7501,295 Sq.Ft.3/24/2023Gainsborough Cir2N/AN/AN/A11,275 Sq.Ft.10/10/2022Gainsborough Ct1N/AN/AN/A13,284 Sq.Ft.N/AGainsborough Sq5122$247,0005,930 Sq.Ft.8/5/2024Galberry Rd11242$415,7742,388 Sq.Ft.5/28/2024Gale Ave5932$296,6721,412 Sq.Ft.5/19/2025Galies Pointe Ln2133$502,4002,401 Sq.Ft.8/15/2023Gallbush Rd8032$555,3282,229 Sq.Ft.4/16/2025Gallenway Ter3142$499,2862,027 Sq.Ft.11/28/2023Galleon Dr2432$299,4581,375 Sq.Ft.7/7/2021Gallop Ave543$367,0006,115 Sq.Ft.7/8/2021Galston Ct943$530,6672,657 Sq.Ft.2/27/2019Gammon Trl1243$536,1672,043 Sq.Ft.5/17/2022Gangway Trce633$427,6672,137 Sq.Ft.9/7/2023Gannet Ct9N/AN/AN/AN/A8/3/2001Garden Tree Rd543$629,8002,900 Sq.Ft.7/21/2022Garland Dr1463$599,5833,639 Sq.Ft.10/10/2023Garnes Ave1442$346,8181,647 Sq.Ft.8/14/2023Garrett St932$320,2221,807 Sq.Ft.4/29/2025Garth Way643$468,5001,937 Sq.Ft.5/19/2025Garwood Ln943$618,1112,638 Sq.Ft.9/4/2024Gaskin Ct563$591,5003,695 Sq.Ft.4/5/2022Gaston Ct632$321,3331,589 Sq.Ft.2/28/2025Gaston Dr2132$307,8501,501 Sq.Ft.12/6/2022Gatefield Ln432$469,5002,087 Sq.Ft.6/15/2021Gates Lndg232$343,5001,168 Sq.Ft.9/1/2017Gateway Ct28322$256,5181,141 Sq.Ft.N/AGatewood Ct1943$412,9471,794 Sq.Ft.2/28/2024Gatling St12N/AN/A$385,167N/A4/11/2019Gauntlet Ct1042$336,8001,609 Sq.Ft.4/30/2025Gauntlet Dr1732$315,8241,609 Sq.Ft.12/4/2020Gavin Rd2532$311,0421,794 Sq.Ft.4/8/2025Gemstone Ln1453$630,7142,967 Sq.Ft.5/5/2023Gendron St433$339,7501,934 Sq.Ft.7/12/2024Gene Cres3732$304,3611,394 Sq.Ft.1/17/2023Geneva Ave2032$342,0596,966 Sq.Ft.4/29/2025Genoa Cres1132$377,0001,617 Sq.Ft.6/5/2024Genovese Reach854$793,7143,855 Sq.Ft.8/29/2024George Dr1632$288,7501,314 Sq.Ft.9/13/2023George Olah Dr1643$708,3333,291 Sq.Ft.9/17/2024Georgetown Blvd3642$408,3132,364 Sq.Ft.6/11/2024George Washington Hwy31132$364,0383,864 Sq.Ft.5/30/2025Georgia Rd2032$373,3681,727 Sq.Ft.11/4/2024Georgie Ct853$553,2503,213 Sq.Ft.4/16/2021Gerrey Dr1332$341,4621,558 Sq.Ft.11/29/2023Gibraltar Ln1053$718,4443,306 Sq.Ft.7/10/2024Gibson Dr1932$398,0561,863 Sq.Ft.3/1/2024Gideon Cres1332$284,0001,459 Sq.Ft.9/24/2024Gilbert Ct532$325,6001,092 Sq.Ft.5/11/2020Gilbys Ct743$523,1432,754 Sq.Ft.7/20/2022Gilchrist Ct1043$792,7783,750 Sq.Ft.7/19/2024Giles Dr1732$399,8241,601 Sq.Ft.5/18/2022Gillette Ct554$856,8004,418 Sq.Ft.5/10/2018Gilmerton Rd6642$332,5452,933 Sq.Ft.1/30/2025Ginger Ct1132$345,3331,491 Sq.Ft.1/14/2025Girard Ave1442$309,0711,595 Sq.Ft.3/10/2025Glades Ct563$679,2003,655 Sq.Ft.8/2/2023Gladesdale Dr2742$470,4231,808 Sq.Ft.3/6/2024Glasgow St2143$566,5712,445 Sq.Ft.6/5/2025Glemmings Ct443$514,6672,670 Sq.Ft.4/15/2022Glenco Ct1N/AN/AN/AN/AN/AGlencoe Ct1654$1,060,5003,835 Sq.Ft.4/29/2025Glencoe St253$656,0002,513 Sq.Ft.2/23/2022Glenco St1N/AN/AN/A600 Sq.Ft.N/AGlen Ct332$449,3332,295 Sq.Ft.7/15/1999Glenda Cres1343$491,9232,207 Sq.Ft.9/23/2022Glendale Ave5632$321,3151,391 Sq.Ft.5/2/2025Gleneagle Ct642$514,5001,968 Sq.Ft.4/13/2016Glen Lndg753$511,3332,606 Sq.Ft.9/22/2023Glenmar St532$357,7501,262 Sq.Ft.5/2/2025Glen Oak Cv632$362,6671,563 Sq.Ft.10/12/2018Glen Oak Xing532$347,2001,429 Sq.Ft.3/2/2017Glenrose Ct543$581,6002,594 Sq.Ft.6/27/2023Glenview Rd1042$395,0001,753 Sq.Ft.3/6/2024Glenwood Dr1242$491,5002,067 Sq.Ft.10/16/2020Global Cir842$458,5711,835 Sq.Ft.1/13/2025Gloria Ct343$535,0002,982 Sq.Ft.8/29/2022Gloria Dr6942$485,5291,875 Sq.Ft.4/28/2025Gloss St1632$419,9331,555 Sq.Ft.3/27/2024Glouchester Cir1232$270,1671,436 Sq.Ft.11/26/2024Glovers Ct632$376,3331,520 Sq.Ft.4/15/2024Godwin Ave4432$309,2422,200 Sq.Ft.2/13/2025Goldbell Ct953$690,1253,055 Sq.Ft.7/26/2024Goldcrest Dr3832$364,6221,747 Sq.Ft.1/24/2024Golden Ct1142$508,8892,258 Sq.Ft.8/9/2022Golden Cypress Ct1632$367,3751,528 Sq.Ft.9/1/2023Golden Hind Ct253$566,0003,111 Sq.Ft.8/18/2022Golden Hind Rd2143$543,0482,711 Sq.Ft.10/21/2024Golden Maple Dr3243$735,6563,464 Sq.Ft.3/28/2025Golden Oaks Ln4832$215,5221,237 Sq.Ft.4/1/2025Gold Finch Ct343$380,0001,969 Sq.Ft.2/5/2022817 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
954 Railroad AveChesapeake, VA 23324
Estimated Value $319,000
Living Area 1,888 SqFt
Beds 4
Baths 2.5
Year Built 2009
Property Type Single Family
Ownership Type Related
APN 1600000000940
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
510 Sloane StChesapeake, VA 23324
Estimated Value $307,000
Living Area 1,464 SqFt
Beds 2
Baths 2.5
Year Built 2016
Property Type Condominium
Ownership Type Individual
APN 1580001001430
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
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
4109 Everett StChesapeake, VA 23324
Estimated Value $332,000
Living Area 1,672 SqFt
Beds 4
Baths 2.5
Year Built 2017
Property Type Single Family
Ownership Type Individual
APN 1600000001731
Neighborhood South Norfolk
School District Chesapeake City Public Schools
209 Outlaw StChesapeake, VA 23320
Estimated Value $399,000
Living Area 2,236 SqFt
Beds 4
Baths 2.5
Year Built 2003
Property Type Single Family
Ownership Type Multiple
APN 0351004001500
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1855 Doubloon WayChesapeake, VA 23323
Estimated Value $407,000
Living Area 1,875 SqFt
Beds 3
Baths 2.5
Year Built 2018
Property Type Condominium
Ownership Type Related
APN 0354003001450
Neighborhood Deep Creek
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
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
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
703 Durham AveChesapeake, VA 23320
Estimated Value $408,000
Living Area 2,501 SqFt
Beds 4
Baths 2.5
Year Built 2002
Property Type Single Family
Ownership Type Related
APN 0351004003070
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
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
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