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
Oak Gate Dr2542$357,9091,719 Sq.Ft.4/7/2025Oak Grove Rd5842$479,2143,165 Sq.Ft.2/7/2024Oak Grove Run532$337,2001,490 Sq.Ft.4/23/2024Oak Hill Way1442$360,1431,734 Sq.Ft.7/14/2024Oak Knoll Ln542$369,3331,866 Sq.Ft.11/7/2022Oak Lake Dr242$359,5001,745 Sq.Ft.12/1/2021Oak Lake Run1832$337,5561,506 Sq.Ft.1/31/2025Oak Lake Run Ct1N/AN/AN/A175,028 Sq.Ft.1/31/2023Oak Lake Ter3132$357,2581,715 Sq.Ft.10/10/2024Oak Leaf Ct1N/AN/AN/A72,010 Sq.Ft.N/AOaklette Ave1642$528,5632,624 Sq.Ft.9/13/2022Oaklette Dr7632$357,9862,045 Sq.Ft.5/9/2025Oak Manor Dr2142$415,9002,013 Sq.Ft.9/11/2024Oak Mears Cv1232$343,4171,285 Sq.Ft.9/26/2024Oak Moss Ct5522$254,0931,352 Sq.Ft.11/5/2024Oak Ridge Dr1442$569,6922,229 Sq.Ft.7/26/2024Oak Ridge Ln633$358,1671,789 Sq.Ft.8/29/2023Oakstone Trl1223$282,0001,353 Sq.Ft.6/26/2020Oakwell Ct542$482,4001,908 Sq.Ft.3/28/2023Oakwood Rd1043$506,5002,480 Sq.Ft.4/28/2023Obsidian Ct754$709,8003,259 Sq.Ft.4/14/2022Obsidian Way553$720,8003,131 Sq.Ft.7/17/2023Odman Dr1943$640,4713,752 Sq.Ft.3/10/2025Ohio St4142$275,3891,805 Sq.Ft.10/18/2024Oil Bird Ln542$518,0002,149 Sq.Ft.5/21/2025Oklahoma Dr5232$304,0851,670 Sq.Ft.9/23/2024Old Atlantic Ave3432$264,2591,652 Sq.Ft.2/4/2025Old Barnes Rd164$464,0004,541 Sq.Ft.8/9/2000Old Battlefield Blvd3432$453,7732,053 Sq.Ft.3/31/2025Old Bridge Ln1754$792,2144,064 Sq.Ft.7/8/2020Old Butts Station Rd243$452,5001,988 Sq.Ft.5/21/2018Old Centerville Tpke1632$455,7271,632 Sq.Ft.8/7/2023Old Coach Rd2553$706,9603,548 Sq.Ft.1/10/2024Old Deep Creek Blvd943$288,2863,526 Sq.Ft.8/19/2019Old Dock Landing Rd1442$469,5002,452 Sq.Ft.11/12/2021Old Dr6132$457,6322,128 Sq.Ft.11/26/2024Olde Stone Way2832$244,2961,352 Sq.Ft.10/24/2024Old Farm Ave343$740,0001,900 Sq.Ft.5/3/2001Old Fields Arch3743$591,0003,125 Sq.Ft.4/26/2024Old Fox Trl2832$257,3211,507 Sq.Ft.5/4/2023Old Galberry Rd3142$361,4331,694 Sq.Ft.5/21/2025Old George Washington Hwy1531$279,6675,407 Sq.Ft.8/8/2016Old Grandad Ln2343$528,4212,828 Sq.Ft.4/23/2024Old Greenbrier Rd14822$226,5812,754 Sq.Ft.4/19/2025Old Gum Rd532$328,6001,341 Sq.Ft.1/28/2025Old Jolliff Rd832$413,4001,879 Sq.Ft.7/27/2021Old Manor Rd1432$325,9291,563 Sq.Ft.10/24/2024Old Mill Rd9532$400,3132,084 Sq.Ft.4/15/2025Old Oak Grove Rd453$559,5003,433 Sq.Ft.10/4/2018Old Oaks Cir443$545,5002,576 Sq.Ft.6/27/2018Old Oaks Ter1143$556,3642,743 Sq.Ft.5/8/2021Old Pughsville Rd3732$316,3061,603 Sq.Ft.4/28/2025Old Rock St1143$641,3333,443 Sq.Ft.6/14/2021Old Soldier Rd1N/AN/A$375,000N/AN/AOld Spice Ct1132$278,5451,704 Sq.Ft.7/29/2022Old State Rd431$318,3331,634 Sq.Ft.6/28/2021Old Taylor Rd3N/AN/AN/A39,665 Sq.Ft.1/15/2004Old Vintage Rd2954$751,1923,622 Sq.Ft.3/14/2022Old Virginia Rd5143$431,1822,623 Sq.Ft.4/23/2025Old Woodland Dr2843$570,1152,857 Sq.Ft.4/24/2025Old Woodmont Dr222$499,0001,331 Sq.Ft.10/25/2002Oldwood St3432$289,6191,575 Sq.Ft.12/28/2022Oleander Ave9032$332,9761,608 Sq.Ft.10/28/2024Oliver Ave9532$288,8911,555 Sq.Ft.2/12/2025Olmstead St9843$573,9472,762 Sq.Ft.5/1/2025Omar St5532$273,1851,163 Sq.Ft.5/13/2025Onawa Ln1331$284,6671,273 Sq.Ft.5/14/2024Oneal Ln1N/AN/A$415,000N/AN/AOneford Pl5032$281,2241,739 Sq.Ft.12/31/2024Ontario Ave632$334,0001,495 Sq.Ft.8/15/2024Opal St3N/AN/A$227,333N/A7/19/2016Opoho Cres842$306,2861,176 Sq.Ft.4/24/2025Opoho Ct542$306,8001,182 Sq.Ft.7/19/2022Orange Root Dr953$692,2863,154 Sq.Ft.10/21/2021Orangewood Rd2743$623,9172,851 Sq.Ft.7/19/2024Orchard Grove Dr11622$268,8961,386 Sq.Ft.5/13/2025Orchard Trail Rd742$533,2862,041 Sq.Ft.1/19/2023Orchard Way2422$271,8261,383 Sq.Ft.11/22/2024Oregon Xing1443$516,0002,228 Sq.Ft.8/25/2023Orford Cir1232$263,1671,240 Sq.Ft.9/23/2022Oriole Dr4943$591,0233,057 Sq.Ft.10/25/2024Orkney Ct1543$602,0712,706 Sq.Ft.10/2/2024Ormer Rd5132$327,5101,539 Sq.Ft.4/24/2025Orville Ave4232$289,6501,554 Sq.Ft.7/15/2024Osborn Ave4032$312,1031,448 Sq.Ft.2/28/2025Osprey Ct3242$225,0311,467 Sq.Ft.N/AOtterbourne Cir6533$363,4841,769 Sq.Ft.4/16/2025Otterbourne Ct833$369,7501,804 Sq.Ft.5/11/2023Otterbourne Quay433$362,7501,771 Sq.Ft.6/15/2021Outlaw St4743$394,4633,354 Sq.Ft.11/19/2024Overbrook Ave932$334,1671,398 Sq.Ft.4/27/2023Overlook Pl1143$603,7782,969 Sq.Ft.8/21/2020Overshot Arch1043$515,5002,520 Sq.Ft.9/22/2020Owens Ter1043$439,4002,527 Sq.Ft.7/18/2018Oxbow Ct553$701,3333,458 Sq.Ft.1/23/2020Pacels Way2653$671,6153,082 Sq.Ft.8/26/2024Packard St1N/AN/A$460,000N/A2/28/2020Paddington Ct542$554,7502,423 Sq.Ft.4/16/2024Page Ct1031$268,1001,076 Sq.Ft.11/18/2021Page St10N/AN/AN/A3,930 Sq.Ft.7/30/20184109 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
1512 Shell RdChesapeake, VA 23323
Estimated Value $276,000
Living Area 1,344 SqFt
Beds 3
Baths 2.5
Year Built 1960
Property Type Single Family
Ownership Type Corporate
APN 0261001000010
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
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
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
568 Marc Smiley RdChesapeake, VA 23324
Estimated Value $318,000
Living Area 1,720 SqFt
Beds 3
Baths 2.5
Year Built 2017
Property Type Condominium
Ownership Type Individual
APN 1580001001270
Neighborhood South Norfolk
School District Chesapeake City Public Schools
1741 Fortune TerChesapeake, VA 23323
Estimated Value $418,000
Living Area 2,036 SqFt
Beds 3
Baths 2.5
Year Built 2022
Property Type Condominium
Ownership Type Related
APN 0354003003750
Neighborhood Deep Creek
School District Chesapeake City Public Schools
4102 Wake AveChesapeake, VA 23324
Estimated Value $297,000
Living Area 1,555 SqFt
Beds 3
Baths 2
Year Built 1967
Property Type Single Family
Ownership Type Individual
APN 1601001000500
Neighborhood South Norfolk
School District Chesapeake City Public Schools
4162 Reid StChesapeake, VA 23324
Estimated Value $282,000
Living Area 1,330 SqFt
Beds 3
Baths 2
Year Built 1955
Property Type Single Family
Ownership Type Individual
APN 1600000001510
Neighborhood South Norfolk
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
713 Rue MarseilleChesapeake, VA 23320
Estimated Value $204,000
Living Area 919 SqFt
Beds 2
Baths 2
Year Built 1996
Property Type Condominium
Ownership Type Individual
APN 0367009000670
Neighborhood Rivercrest
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
1408 Portlock RdChesapeake, VA 23324
Estimated Value $290,000
Living Area 2,005 SqFt
Beds 4
Baths 2
Year Built 1936
Property Type Single Family
Ownership Type Related
APN 1590000002550
Neighborhood South Norfolk
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
875 Rivanna River ReachChesapeake, VA 23320
Estimated Value $280,000
Living Area 1,434 SqFt
Beds 2
Baths 1.5
Year Built 1990
Property Type Condominium
Ownership Type Individual
APN 0367003000600
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1233 Marge DrChesapeake, VA 23320
Estimated Value $302,000
Living Area 1,336 SqFt
Beds 3
Baths 1.5
Year Built 1975
Property Type Single Family
Ownership Type Individual
APN 0272001000440
Neighborhood Rivercrest
School District Chesapeake City Public Schools