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
Howelsen Ct743$640,0002,674 Sq.Ft.8/27/2021Hoyt Dr832$328,5001,513 Sq.Ft.4/22/2024Hubard Dr1232$328,7271,567 Sq.Ft.3/27/2023Hudson St432$263,0002,284 Sq.Ft.10/16/2018Hughes Ave2932$264,9641,295 Sq.Ft.11/19/2024Hugh Ln1153$634,8002,889 Sq.Ft.4/28/2022Hulen Dr1643$444,3752,310 Sq.Ft.6/21/2024Hull St6932$237,6271,317 Sq.Ft.10/28/2024Hummingbird St1432$276,3851,667 Sq.Ft.N/AHumphries Ln531$361,5001,164 Sq.Ft.9/16/2022Hungarian Rd1943$692,0672,513 Sq.Ft.6/15/2023Hunningdon Lakes Blvd142$483,0002,031 Sq.Ft.8/4/2015Hunningdon Woods Blvd5243$548,0852,604 Sq.Ft.5/22/2024Hunt Club Ln1043$750,4443,029 Sq.Ft.11/27/2018Hunter Green Ct543$519,2002,214 Sq.Ft.10/27/2022Huntersbow Ct343$575,5003,112 Sq.Ft.2/23/2024Hunters Bridge Dr1N/AN/AN/A129,138 Sq.Ft.10/27/2020Hunters Glen Ct2042$408,4211,831 Sq.Ft.2/25/2025Hunters Quay7932$263,8461,464 Sq.Ft.4/22/2025Hunter St8N/AN/A$270,000N/A5/16/2017Hunthaven Ct252$797,0003,904 Sq.Ft.1/3/2017Hunting Wood Rd1543$361,7861,713 Sq.Ft.10/2/2024Huntly Ct2132$248,2381,281 Sq.Ft.9/4/2024Huntly Dr5532$260,9621,350 Sq.Ft.12/9/2024Hunt Trl632$254,0001,398 Sq.Ft.10/23/2014Hurdle Dr7132$381,2811,639 Sq.Ft.9/16/2024Huxley Dr433$302,7501,314 Sq.Ft.12/30/2020Hydenwood Cres2242$471,9442,310 Sq.Ft.3/31/2025Hydrangea Ct543$691,0002,569 Sq.Ft.7/18/2024Hywood Ct843$603,6252,580 Sq.Ft.6/29/2022Ians Way2053$685,4123,105 Sq.Ft.9/12/2023Ibis Rd2053$769,4503,242 Sq.Ft.4/17/2025Ida St542$276,0001,299 Sq.Ft.7/30/2024Ike St1N/AN/AN/A100 Sq.Ft.N/AIlex St1432$332,6151,406 Sq.Ft.11/19/2024Ilkly Cir1332$265,6671,525 Sq.Ft.9/17/2024Illuminare Way753$673,5002,889 Sq.Ft.9/28/2020Independence Pkwy48N/AN/AN/A26,129 Sq.Ft.2/6/2025Indiana Ave2932$326,3641,593 Sq.Ft.3/20/2025Indian Cedar Dr4142$469,5882,156 Sq.Ft.12/12/2024Indian Creek Rd13932$623,6602,305 Sq.Ft.5/15/2024Indianola Ct732$404,8331,790 Sq.Ft.10/5/2016Indian River Rd10032$336,26110,520 Sq.Ft.3/26/2025Indigo Rd2732$326,5771,603 Sq.Ft.2/18/2025Industrial Ave20N/AN/AN/A6,368 Sq.Ft.11/21/2022Inez Ln1532$384,8671,626 Sq.Ft.12/11/2023Inkwell Ct932$484,5562,058 Sq.Ft.12/27/2023Inland Rd1443$737,0002,720 Sq.Ft.11/21/2024Inlet Quay11122$246,9441,355 Sq.Ft.5/29/2025Innovation Dr50N/A1N/A4,749 Sq.Ft.10/23/2024International Plz7N/AN/AN/A32,213 Sq.Ft.11/2/2016Interstate2N/AN/AN/AN/AN/AIowa St7232$315,6001,776 Sq.Ft.2/11/2025Iron Bridge Ln943$483,7502,088 Sq.Ft.1/13/2022Iron Clad Ct743$434,3332,341 Sq.Ft.6/25/2020Isabel Ct454$868,0003,902 Sq.Ft.11/12/2020Isabella Dr1732$405,4121,861 Sq.Ft.8/16/2024Ivanhoe Ct843$610,7142,604 Sq.Ft.2/13/2021Iverness Ct432$382,7501,797 Sq.Ft.12/11/2007Ivy Brg1N/AN/AN/A145,522 Sq.Ft.N/AIvy Cres2343$432,1502,857 Sq.Ft.8/30/2024Ivy Ct443$425,6672,717 Sq.Ft.1/25/2016Ivystone Sq1N/AN/AN/A115,568 Sq.Ft.1/23/2015Jackie Dr1631$282,3131,204 Sq.Ft.6/2/2023Jackson Ave10732$278,9491,716 Sq.Ft.4/3/2025Jacob Ct1442$380,7002,024 Sq.Ft.4/14/2023Jadens Way3533$383,9391,816 Sq.Ft.2/13/2025Jake Ln1543$472,6922,250 Sq.Ft.8/16/2023Jamaica Ave1553$677,9233,164 Sq.Ft.9/4/2024James Earl Dr1442$524,1672,271 Sq.Ft.11/29/2021James Lndg1243$611,4293,416 Sq.Ft.10/14/2022James St2143$339,1431,670 Sq.Ft.7/3/2024Jana Ct432$412,0001,502 Sq.Ft.12/8/2023Janell Ct653$363,6672,277 Sq.Ft.9/14/2018Janes Way1043$661,4443,405 Sq.Ft.11/17/2021Janice Lynn Ct4832$189,0001,040 Sq.Ft.9/12/2024Janson Dr2032$405,6672,100 Sq.Ft.5/23/2024Jardin Cv643$547,6002,800 Sq.Ft.9/10/2024Jarman Rd1N/AN/AN/A40,417 Sq.Ft.N/AJarvis Rd1942$383,0531,802 Sq.Ft.8/22/2024Jasmine Ct1143$538,0002,425 Sq.Ft.2/20/2023Jaye Cir1232$385,0911,489 Sq.Ft.4/17/2024Jean Ct742$399,1671,965 Sq.Ft.4/22/2025Jean Shackelford Dr843$621,2503,231 Sq.Ft.5/20/2014Jefferson St4032$270,0591,574 Sq.Ft.5/16/2025Jenna Ct543$494,8002,428 Sq.Ft.7/28/2021Jennell Ct743$496,0002,642 Sq.Ft.11/29/2021Jennings Ln4N/AN/A$300,500N/AN/AJeremy Way1043$668,3002,986 Sq.Ft.6/2/2025Jerome St831$296,1251,348 Sq.Ft.5/26/2022Jerry Locker St332$352,0001,448 Sq.Ft.4/17/2025Jerryville St1643$632,3852,729 Sq.Ft.1/25/2023Jersey Cir1232$270,1671,474 Sq.Ft.2/21/2024Jester Ct432$363,2501,592 Sq.Ft.3/7/2006Joan Ct453$622,0002,676 Sq.Ft.7/17/2024Jo Anne Cir3742$486,7431,887 Sq.Ft.5/29/2025Jockey Ct653$763,4003,573 Sq.Ft.5/27/2022Jodi Lynn Trl2343$682,2003,117 Sq.Ft.10/10/2023John Anthony Ct643$550,8332,590 Sq.Ft.3/28/2022John Etheridge Rd3043$707,3332,842 Sq.Ft.8/22/2024304 Primrose LnChesapeake, VA 23320
Estimated Value $224,000
Living Area 1,053 SqFt
Beds 2
Baths 2
Year Built 1994
Property Type Condominium
Ownership Type Individual
APN 0367010000030
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
4139 1st StChesapeake, VA 23324
Estimated Value $299,000
Living Area 1,008 SqFt
Beds 2
Baths 1
Year Built 2005
Property Type Single Family
Ownership Type Related
APN 1590000002910
Neighborhood South Norfolk
School District Chesapeake City Public Schools
305 Creek LnChesapeake, VA 23320
Estimated Value $536,000
Living Area 2,952 SqFt
Beds 4
Baths 2.5
Year Built 1989
Property Type Single Family
Ownership Type Related
APN 0369004000230
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
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
511 Sloane StChesapeake, VA 23324
Estimated Value $298,000
Living Area 1,570 SqFt
Beds 2
Baths 2.5
Year Built 2017
Property Type Condominium
Ownership Type Individual
APN 1580001001510
Neighborhood South Norfolk
School District Chesapeake City Public Schools
817 Royal Grove CtChesapeake, VA 23320
Estimated Value $349,000
Living Area 2,041 SqFt
Beds 3
Baths 2.5
Year Built 1997
Property Type Townhouse
Ownership Type Multiple
APN 0368002000140
Neighborhood Rivercrest
School District Chesapeake City Public Schools
928 Wickford DrChesapeake, VA 23320
Estimated Value $224,000
Living Area 1,040 SqFt
Beds 3
Baths 2
Year Built 1986
Property Type Townhouse
Ownership Type Related
APN 0367001000530
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1100 Railroad AveChesapeake, VA 23324
Estimated Value $328,000
Living Area 1,931 SqFt
Beds 3
Baths 2.5
Year Built 2003
Property Type Single Family
Ownership Type Individual
APN 1590000004042
Neighborhood South Norfolk
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
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
708 Bulrush CtChesapeake, VA 23320
Estimated Value $471,000
Living Area 2,189 SqFt
Beds 4
Baths 2.5
Year Built 1991
Property Type Single Family
Ownership Type Individual
APN 0369001000470
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
4149 Everett StChesapeake, VA 23324
Estimated Value $306,000
Living Area 1,590 SqFt
Beds 3
Baths 2.5
Year Built 2005
Property Type Single Family
Ownership Type Multiple
APN 1600000001861
Neighborhood South Norfolk
School District Chesapeake City Public Schools
400 Harbour North DrChesapeake, VA 23320
Estimated Value $196,000
Living Area 1,216 SqFt
Beds 3
Baths 1.5
Year Built 1978
Property Type Townhouse
Ownership Type Individual
APN 0364003000260
Neighborhood Rivercrest
School District Chesapeake City Public Schools