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
Heron Bay Ln1253$696,2503,123 Sq.Ft.4/1/2024Herring Ditch Rd2432$572,6521,999 Sq.Ft.11/26/2024Herrington Ln943$462,6672,495 Sq.Ft.8/30/2022Herron Dr1542$438,4171,972 Sq.Ft.9/14/2021Hertz Rd1031$380,2501,683 Sq.Ft.6/28/2019Hessian Loop2154$984,3893,800 Sq.Ft.3/12/2025Heydon Ct353$597,5002,873 Sq.Ft.6/3/2019Hibben Rd1532$343,8671,605 Sq.Ft.7/13/2023Hickory Forest Dr2454$1,008,4004,344 Sq.Ft.10/4/2024Hickory Hinge Way1042$509,0002,427 Sq.Ft.2/8/2022Hickory Hollow Ct1043$536,7002,437 Sq.Ft.3/12/2025Hickory Rd4242$609,8532,409 Sq.Ft.6/12/2024Hickory Ridge Ct1N/AN/AN/A425 Sq.Ft.N/AHickory Ridge Rd2432$463,0001,963 Sq.Ft.12/1/2023Hickory Station Dr633$1,081,6003,106 Sq.Ft.6/28/2023Hickory Woods Ct1732$430,0001,875 Sq.Ft.10/22/2024Hidden Falls Ct643$538,1672,937 Sq.Ft.8/9/2021Hidden Falls Ln5243$576,8002,918 Sq.Ft.2/7/2025Hidden Harbor Ct1743$581,5003,045 Sq.Ft.1/11/2024Higgins Ave1132$286,6001,348 Sq.Ft.1/25/2022Higgins Ct832$292,2501,618 Sq.Ft.2/21/2020Higgins St1032$299,2001,528 Sq.Ft.1/20/2025Highgate Ct744$814,7503,653 Sq.Ft.9/29/2023Highland Ave1N/AN/A$437,000N/A1/29/1999Highlands Ct843$564,7502,695 Sq.Ft.9/30/2022Highmark Rd1N/AN/AN/AN/AN/AHigh Point Cir842$471,5001,701 Sq.Ft.11/19/2020High Point Ln1642$481,1881,859 Sq.Ft.3/28/2025High Point Pl342$487,6671,939 Sq.Ft.N/AHigh Ridge Ct553$637,8002,877 Sq.Ft.3/31/2015High Rock Ct253$679,5003,268 Sq.Ft.2/22/2024High Tide Way1043$370,2002,108 Sq.Ft.10/23/2023Highway 172N/AN/AN/AN/AN/AHighway Hwy4N/AN/AN/AN/AN/AHilda Pine Dr2832$409,5001,473 Sq.Ft.3/7/2022Hillard St242$369,0001,614 Sq.Ft.10/24/2019Hillburn Dr1532$319,9331,223 Sq.Ft.12/2/2024Hillcrest Pkwy18N/AN/AN/A21,759 Sq.Ft.8/20/2021Hillingdon Bnd8822$234,5751,366 Sq.Ft.4/25/2025Hill Ln7122$296,9001,486 Sq.Ft.1/2/2025Hill Point Ct1042$515,5002,095 Sq.Ft.3/19/2025Hills Dr1242$462,2731,967 Sq.Ft.4/8/2025Hillside Ave4842$510,6672,189 Sq.Ft.3/9/2025Hillside Ct443$496,5001,956 Sq.Ft.6/29/2020Hillside Trce1043$521,4442,419 Sq.Ft.8/2/2020Hill St7532$320,65817,184 Sq.Ft.8/12/2024Hillston Arch1043$714,4003,331 Sq.Ft.3/30/2023Hillston Ct454$729,2503,569 Sq.Ft.7/22/2015Hilltop Ct642$541,0002,242 Sq.Ft.6/7/2022Hilltop Dr2142$545,8502,324 Sq.Ft.7/15/2024Hillwell Ct533$491,0002,278 Sq.Ft.12/11/2024Hillwell Rd16242$486,5722,109 Sq.Ft.5/19/2025Hilton Ave1432$315,2141,694 Sq.Ft.3/31/2025Hilton Ct342$322,0001,824 Sq.Ft.1/23/2023Hines Ave12N/AN/AN/AN/A6/9/2018Hines St332N/A1,350 Sq.Ft.N/AHinksley Ct342$467,6671,736 Sq.Ft.8/30/2013Hinton Ave3432$318,2731,474 Sq.Ft.4/17/2025Historic Way2N/AN/AN/A8,626 Sq.Ft.N/AHodges Rd1142$403,3641,921 Sq.Ft.1/19/2024Hoffman Ave1632$345,5711,504 Sq.Ft.5/21/2025Holbrook Trce843$532,3752,491 Sq.Ft.6/15/2023Holland Blvd30N/AN/AN/A24,497 Sq.Ft.3/14/2022Holland Dr3N/AN/AN/A5,699 Sq.Ft.N/AHollins Ct2632$359,3601,849 Sq.Ft.12/2/2022Hollow Ct543$479,4002,157 Sq.Ft.5/19/2018Hollowell Ln1N/AN/AN/A21,126 Sq.Ft.N/AHolly Ave4042$284,8003,179 Sq.Ft.4/18/2025Holly Berry Ln7533$330,5071,676 Sq.Ft.5/15/2025Holly Cove Dr6932$163,5371,383 Sq.Ft.2/18/2025Hollygate Ln1543$608,2862,868 Sq.Ft.6/6/2025Holly Glen Dr1533$328,6001,683 Sq.Ft.10/27/2022Holly Ridge Ct1142$416,2731,919 Sq.Ft.4/28/2023Holly Ridge Dr3642$410,0291,757 Sq.Ft.8/19/2024Hollywood Dr3942$406,7501,930 Sq.Ft.3/18/2025Holmes Trl743$700,4292,914 Sq.Ft.3/6/2023Holston River Ct1822$227,2941,035 Sq.Ft.7/24/2024Holt Dr2N/AN/AN/A240 Sq.Ft.N/AHolyoke Ln6723$276,5151,352 Sq.Ft.2/24/2025Homecrest Blvd1N/AN/AN/A3,316 Sq.Ft.N/AHomestead Rd3532$405,4331,834 Sq.Ft.1/18/2022Hondo Ct353$638,0002,996 Sq.Ft.4/21/2023Honeybee Ct654$656,0003,112 Sq.Ft.10/13/2020Honey Flower Ct643$494,6672,598 Sq.Ft.2/12/2025Honey Locust Way2743$523,1302,658 Sq.Ft.8/30/2024Honey Milk Rd2443$531,7272,376 Sq.Ft.4/3/2025Hook St332$300,6671,692 Sq.Ft.9/26/2016Hoover Ave11232$274,4501,525 Sq.Ft.4/11/2025Hopewell Dr3132$371,1291,814 Sq.Ft.11/11/2024Hornsea Ct332$323,0001,630 Sq.Ft.5/25/2012Hornsea Rd5132$327,0781,609 Sq.Ft.5/27/2025Hornswaggle Way1333$401,7271,866 Sq.Ft.8/22/2024Hornswood Ct342$502,5001,882 Sq.Ft.3/24/2022Horseback Run2N/AN/AN/AN/AN/AHorse Camp Ln1743$565,5002,561 Sq.Ft.3/13/2025Horse Run Dr5133$320,1631,645 Sq.Ft.5/27/2025Horseshoe Dr3132$467,4521,888 Sq.Ft.7/9/2024Horton Way2253$622,3333,059 Sq.Ft.6/2/2025Hot Mill Ct453$559,2503,305 Sq.Ft.12/21/2017Howard Rd932$319,0001,503 Sq.Ft.5/2/20251923 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
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
614 Reunion StChesapeake, VA 23324
Estimated Value $317,000
Living Area 1,570 SqFt
Beds 2
Baths 2.5
Year Built 2014
Property Type Condominium
Ownership Type Individual
APN 1580001000080
Neighborhood South Norfolk
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
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
446 Supplejack CtChesapeake, VA 23320
Estimated Value $467,000
Living Area 2,293 SqFt
Beds 4
Baths 2.5
Year Built 1990
Property Type Single Family
Ownership Type Related
APN 0369003000120
Neighborhood Rivercrest
School District Chesapeake City Public Schools
847 Creekside CresChesapeake, VA 23320
Estimated Value $264,000
Living Area 1,348 SqFt
Beds 2
Baths 2.5
Year Built 1990
Property Type Townhouse
Ownership Type Corporate
APN 0367006000310
Neighborhood Rivercrest
School District Chesapeake City Public Schools
904 Robert Welch CtChesapeake, VA 23320
Estimated Value $574,000
Living Area 3,351 SqFt
Beds 5
Baths 3
Year Built 2006
Property Type Single Family
Ownership Type Multiple
APN 0361016000230
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
1317 Great Bridge BlvdChesapeake, VA 23320
Estimated Value $276,000
Living Area 1,657 SqFt
Beds 3
Baths 2
Year Built 1955
Property Type Single Family
Ownership Type Related
APN 0362001000640
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
736 Huntly DrChesapeake, VA 23320
Estimated Value $251,000
Living Area 1,240 SqFt
Beds 3
Baths 1.5
Year Built 1990
Property Type Townhouse
Ownership Type Corporate
APN 0367002000640
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
1216 Destiny WayChesapeake, VA 23320
Estimated Value $434,000
Living Area 1,559 SqFt
Beds 4
Baths 2.5
Year Built 2010
Property Type Single Family
Ownership Type Related
APN 0353001000120
Neighborhood Rivercrest
School District Chesapeake City Public Schools
600 Muddy Creek RdChesapeake, VA 23324
Estimated Value $335,000
Living Area 1,774 SqFt
Beds 3
Baths 2.5
Year Built 2017
Property Type Condominium
Ownership Type Individual
APN 1580001000240
Neighborhood South Norfolk
School District Chesapeake City Public Schools
4315 Salt Marsh LnChesapeake, VA 23324
Estimated Value $327,000
Living Area 1,960 SqFt
Beds 3
Baths 2.5
Year Built 2015
Property Type Condominium
Ownership Type Individual
APN 1580001002050
Neighborhood South Norfolk
School District Chesapeake City Public Schools