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
Lord Byron Ct1143$388,4552,093 Sq.Ft.5/10/2024Lord Nelson Ct1343$387,3332,085 Sq.Ft.10/6/2020Lords Landing Ct543$606,2002,643 Sq.Ft.5/21/2004Loretta Ln942$498,7782,123 Sq.Ft.6/26/2024Lorton Ct453$793,5003,585 Sq.Ft.2/18/2010Lottie Rd1N/AN/A$393,000N/AN/ALouis Dr1932$329,1111,654 Sq.Ft.4/14/2023Louise James Ct653$558,6003,321 Sq.Ft.11/15/2022Loutro Ct1353$728,0003,104 Sq.Ft.4/9/2025Lovegrove Ave1732$339,8241,573 Sq.Ft.8/23/2024Loxdell Ct442$482,7502,019 Sq.Ft.11/2/2018Loxley Ct343$583,0002,625 Sq.Ft.9/17/2024Lucas Ave542$297,5001,629 Sq.Ft.8/31/2022Lucy Ln1N/AN/AN/A118,308 Sq.Ft.12/17/2014Ludgate Ct532$404,6001,756 Sq.Ft.6/23/2023Ludgate Dr1442$435,0002,045 Sq.Ft.11/1/2018Luid Dr1043$720,5562,863 Sq.Ft.3/17/2025Luray St1142$412,1671,891 Sq.Ft.5/13/2025Luray Ter2942$451,8151,787 Sq.Ft.3/3/2025Lusk St1831$308,6471,485 Sq.Ft.7/23/2024Luther St4332$376,6761,646 Sq.Ft.4/30/2025Luxenbay Ln643$571,8332,515 Sq.Ft.4/5/2019Luxford Ct1143$463,9092,245 Sq.Ft.9/27/2019Luxor Ave742$332,5001,766 Sq.Ft.7/17/2024Lydney Cir1232$265,5451,443 Sq.Ft.10/21/2024Lynchs Ln2N/AN/AN/AN/AN/ALynn Dr7N/AN/A$362,571N/AN/ALynnfield Ct943$472,0002,033 Sq.Ft.9/16/2022Lynnfield Rd2643$469,6192,092 Sq.Ft.7/12/2024Lynnhurst Blvd6943$496,3443,328 Sq.Ft.5/23/2025Lynnwood Gold Ct632$478,4001,961 Sq.Ft.8/17/2023Lyons Ave542$281,0001,665 Sq.Ft.5/6/2020Mabry Mill Pl4022$274,6501,235 Sq.Ft.4/23/2025Macdonald Rd1031$311,62515,480 Sq.Ft.11/17/2023Mactaggert Ave1N/AN/AN/AN/AN/AMadeline Ryan Way3743$663,9412,839 Sq.Ft.1/17/2024Madera Ct343$567,0002,408 Sq.Ft.11/30/2020Madera Rd4242$549,4632,310 Sq.Ft.7/23/2024Madison Garden Ct953$668,4292,960 Sq.Ft.2/24/2021Madison Lynn Way3443$668,7672,913 Sq.Ft.6/2/2023Madison Plz8N/AN/AN/A6,081 Sq.Ft.10/20/2015Madrid Pl632$409,6001,704 Sq.Ft.10/25/2021Magdolna Dr2043$685,6673,192 Sq.Ft.7/1/2024Magnolia Dr1N/AN/A$151,000N/AN/AMagnum Rd643$566,1672,874 Sq.Ft.9/19/2022Mahogany Run943$494,1252,685 Sq.Ft.3/21/2024Maiden Ln743$427,2862,637 Sq.Ft.1/12/2024Maid Marion Cir632$515,6001,793 Sq.Ft.6/13/2024Mainsail Ln343N/A2,133 Sq.Ft.2/28/2025Mains Creek Rd8032$323,1831,561 Sq.Ft.5/22/2025Main St3N/AN/A$308,667N/A3/30/2006Majestic Ct1754$863,0593,073 Sq.Ft.4/28/2025Malbon Dr932$345,0001,762 Sq.Ft.11/10/2023Malcolm Ct1931$189,6841,407 Sq.Ft.5/24/2024Mallard Ct9N/AN/AN/AN/AN/AMallet Way1353$546,2732,934 Sq.Ft.5/19/2023Mallow Ct743$545,6672,802 Sq.Ft.8/22/2019Manchester Ln2132$271,0481,570 Sq.Ft.9/17/2024Mandarin Ln2443$595,5653,118 Sq.Ft.3/20/2023Mandolin Ct2153$567,7372,942 Sq.Ft.10/25/2024Mangrove Dr733$389,8332,158 Sq.Ft.12/22/2009Mann Dr3832$423,8392,172 Sq.Ft.5/22/2025Manning Ct1632$395,1881,647 Sq.Ft.4/5/2023Manor View Ct742$508,8332,327 Sq.Ft.7/27/2017Manteo Ct1142$479,7001,951 Sq.Ft.7/10/2024Maori Ct832$310,3751,328 Sq.Ft.8/11/2021Maori Dr4732$320,8841,413 Sq.Ft.5/7/2024Maple Dr5532$382,3021,739 Sq.Ft.10/24/2024Maple Forest Ct943$636,6672,748 Sq.Ft.5/17/2024Mapleshore Dr2532$429,1502,191 Sq.Ft.4/25/2025Maple St3N/AN/AN/A4,256 Sq.Ft.N/AMapleton Cres2843$456,5362,377 Sq.Ft.1/28/2025Maplewood Ln131$382,0001,352 Sq.Ft.3/5/2004Marble Arch1742$551,6252,299 Sq.Ft.2/21/2023Marcia Ct543$594,4002,631 Sq.Ft.8/21/2015Marco Dr932$367,4441,765 Sq.Ft.12/28/2009Marc Smiley Rd2823$320,3931,683 Sq.Ft.4/17/2025Marcus Ct532$300,6001,293 Sq.Ft.4/13/2015Marcus St5432$282,1851,267 Sq.Ft.3/27/2025Mardean Dr4943$506,2332,845 Sq.Ft.4/21/2023Margaret Ann Ct1243$617,7503,108 Sq.Ft.4/12/2019Margaret Booker Dr1243$314,33342,240 Sq.Ft.10/15/2024Margaret Ct433$512,0002,451 Sq.Ft.1/25/2018Margaret Dr7243$607,5072,907 Sq.Ft.5/13/2025Marge Dr1532$324,8571,539 Sq.Ft.10/17/2023Marie Olson Dr4N/AN/AN/AN/AN/AMarilla Ln754$782,8003,810 Sq.Ft.11/28/2022Marina Ct733$457,8002,453 Sq.Ft.10/28/2021Marina Reach5343$529,4552,845 Sq.Ft.3/5/2025Mariner Dr1132$447,8182,169 Sq.Ft.12/12/2023Marin Ln1133$373,4551,808 Sq.Ft.3/20/2025Marion Dr3732$393,2221,705 Sq.Ft.11/25/2024Marjorie Ln843$684,6673,085 Sq.Ft.5/9/2022Market Pl4N/AN/A$637,00053,200 Sq.Ft.10/6/2014Markland Dr1342$387,9172,008 Sq.Ft.12/2/2024Mark St5531$255,5961,125 Sq.Ft.5/15/2025Marla Ct953$595,4003,451 Sq.Ft.10/26/2023Marlbank Ct843$631,8573,010 Sq.Ft.7/13/2023Marlboro St542$380,5002,790 Sq.Ft.5/30/2024Marlin Ct543$491,0002,219 Sq.Ft.5/8/20251245 Corkwood CirChesapeake, VA 23320
Estimated Value $271,000
Living Area 1,340 SqFt
Beds 3
Baths 2.5
Year Built 1989
Property Type Townhouse
Ownership Type Corporate
APN 0366008000790
Neighborhood Rivercrest
School District Chesapeake City Public Schools
4119 Wake AveChesapeake, VA 23324
Estimated Value $282,000
Living Area 1,363 SqFt
Beds 3
Baths 2
Year Built 1965
Property Type Single Family
Ownership Type Individual
APN 1601001000670
Neighborhood South Norfolk
School District Chesapeake City Public Schools
1712 Foremast LoopChesapeake, VA 23323
Estimated Value $419,000
Living Area 2,120 SqFt
Beds 3
Baths 2.5
Year Built 2020
Property Type Condominium
Ownership Type Individual
APN 0354003004140
Neighborhood Deep Creek
School District Chesapeake City Public Schools
1818 Aft WayChesapeake, VA 23323
Estimated Value $415,000
Living Area 2,036 SqFt
Beds 3
Baths 2.5
Year Built 2021
Property Type Condominium
Ownership Type Multiple
APN 0354003001890
Neighborhood Deep Creek
School District Chesapeake City Public Schools
1125 Lady Ashley DrChesapeake, VA 23320
Estimated Value $402,000
Living Area 2,152 SqFt
Beds 3
Baths 2.5
Year Built 2000
Property Type Condominium
Ownership Type Multiple
APN 0363011000170
Neighborhood Rivercrest
School District Chesapeake City Public Schools
705 Montrose CtChesapeake, VA 23320
Estimated Value $288,000
Living Area 1,516 SqFt
Beds 3
Baths 2.5
Year Built 1991
Property Type Townhouse
Ownership Type Individual
APN 0367002001510
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1231 Woods WayChesapeake, VA 23323
Estimated Value $393,000
Living Area 2,094 SqFt
Beds 4
Baths 2.5
Year Built 2000
Property Type Single Family
Ownership Type Individual
APN 0343023001180
Neighborhood Deep Creek
School District Chesapeake City Public Schools
709 Helmsdale WayChesapeake, VA 23320
Estimated Value $388,000
Living Area 1,552 SqFt
Beds 3
Baths 2
Year Built 1987
Property Type Single Family
Ownership Type Related
APN 0368001000690
Neighborhood Rivercrest
School District Chesapeake City Public Schools
704 Kirkwall CtChesapeake, VA 23320
Estimated Value $460,000
Living Area 1,996 SqFt
Beds 3
Baths 2.5
Year Built 1988
Property Type Single Family
Ownership Type Related
APN 0368001000950
Neighborhood Rivercrest
School District Chesapeake City Public Schools
312 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
4309 Pickney LnChesapeake, VA 23324
Estimated Value $324,000
Living Area 1,720 SqFt
Beds 3
Baths 2.5
Year Built 2018
Property Type Condominium
Ownership Type Multiple
APN 1580001000780
Neighborhood South Norfolk
School District Chesapeake City Public Schools
807 Shenandoah River RdChesapeake, VA 23320
Estimated Value $279,000
Living Area 1,350 SqFt
Beds 2
Baths 2
Year Built 1990
Property Type Condominium
Ownership Type Individual
APN 0367003000790
Neighborhood Rivercrest
School District Chesapeake City Public Schools
858 Creekside CresChesapeake, VA 23320
Estimated Value $257,000
Living Area 1,348 SqFt
Beds 2
Baths 2.5
Year Built 1990
Property Type Townhouse
Ownership Type Individual
APN 0367006000220
Neighborhood Rivercrest
School District Chesapeake City Public Schools
4128 1st StChesapeake, VA 23324
Estimated Value $371,000
Living Area 1,972 SqFt
Beds 4
Baths 3
Year Built 2009
Property Type Single Family
Ownership Type Related
APN 1590000002342
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
308 Esplanade PlChesapeake, VA 23320
Estimated Value $356,000
Living Area 1,849 SqFt
Beds 3
Baths 2.5
Year Built 1994
Property Type Townhouse
Ownership Type Multiple
APN 0367008000200
Neighborhood Rivercrest
School District Chesapeake City Public Schools