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
Lee Shore Ct2032$446,7222,015 Sq.Ft.5/13/2025Leeward Ct343$516,6672,788 Sq.Ft.1/6/2023Leeward Dr3943$445,5282,184 Sq.Ft.5/6/2025Lehman Pines Rd233$683,0003,076 Sq.Ft.N/ALehman Rd531$640,6671,218 Sq.Ft.3/25/2014Leicester Ct853$720,6003,493 Sq.Ft.11/29/2021Lela Ln732$460,5711,875 Sq.Ft.5/13/2022Leleon Ct643$634,8002,725 Sq.Ft.3/25/2024Lemonwood Rd3243$580,2592,722 Sq.Ft.8/8/2023Lena Ct453$653,3332,901 Sq.Ft.12/6/2018Lenore Trl2832$384,3701,903 Sq.Ft.2/14/2025Lenox Ct543$518,5002,322 Sq.Ft.9/14/2023Lenox Trce542$519,2002,261 Sq.Ft.8/14/2024Lenwil Dr743$551,1433,310 Sq.Ft.4/7/2023Leonard Ave5732$257,3751,439 Sq.Ft.10/2/2024Leshea Ct1443$738,8573,121 Sq.Ft.11/14/2024Lester St342$305,3331,592 Sq.Ft.3/20/2018Letcher Ct553$555,6673,245 Sq.Ft.11/4/2020Levee Ct642$386,5001,840 Sq.Ft.8/2/2021Levee Ln1432$378,7141,646 Sq.Ft.4/24/2024Lewis Ln143$517,0002,282 Sq.Ft.2/12/2025Leyland Ct554$783,4003,531 Sq.Ft.8/1/2022Leyte Ave2432$291,8701,474 Sq.Ft.2/1/2021Leytonstone Dr16532$296,9111,782 Sq.Ft.4/22/2025Liam Close1543$664,1543,565 Sq.Ft.3/14/2025Liberton Ct932$312,7781,323 Sq.Ft.11/19/2021Liberty St4132$283,7276,316 Sq.Ft.9/8/2023Libertyville Rd1932$287,1671,354 Sq.Ft.4/23/2024Lido Ct643$562,5002,734 Sq.Ft.7/26/2019Life Tree Trl1534$473,4622,082 Sq.Ft.5/6/2024Lilac Ave12832$350,0421,746 Sq.Ft.3/28/2025Lilley Cove Dr3143$585,8062,912 Sq.Ft.3/8/2023Lil Walnut Ln433$513,0002,488 Sq.Ft.8/2/2024Lima Ct453$647,7503,222 Sq.Ft.8/15/2023Limestone Ct643$653,1672,772 Sq.Ft.7/20/2017Linbay Ct643$490,1672,192 Sq.Ft.8/19/2022Lincoln Ct832$319,7501,374 Sq.Ft.7/17/2023Lincoln Rd1043$366,8002,067 Sq.Ft.11/22/2022Lincolnshire Ct843$619,6252,746 Sq.Ft.3/31/2025Lincoln St1N/AN/A$139,000N/AN/ALindale Dr4332$343,1563,454 Sq.Ft.5/30/2024Lindale Ln1N/AN/AN/AN/AN/ALindbergh Ave2032$368,3681,709 Sq.Ft.4/2/2025Linden Ave9032$296,9771,405 Sq.Ft.5/15/2025Lindenbrook Ln732$476,8571,881 Sq.Ft.8/22/2023Lindenwood Dr2242$458,8502,296 Sq.Ft.4/3/2023Lindsey Ave1932$329,5561,510 Sq.Ft.12/16/2024Lingale Arch943$718,8893,550 Sq.Ft.3/8/2022Lingale Ct354$707,0003,219 Sq.Ft.1/23/2024Linkenborough Dr3642$468,6181,896 Sq.Ft.12/11/2024Links Ct854$895,6254,373 Sq.Ft.9/27/2021Linster St742$309,8005,819 Sq.Ft.2/15/2024Linton Cir1433$497,6922,459 Sq.Ft.7/12/2022Lisas Cove Way1543$528,5002,690 Sq.Ft.3/9/2022Lisbon Rd4932$399,9791,776 Sq.Ft.11/4/2024Little Beaver Rd1332$364,0911,335 Sq.Ft.6/8/2022Little John Trl343$546,6672,650 Sq.Ft.7/12/2024Little Marsh Ln443$614,5002,709 Sq.Ft.5/4/2020Live Oak Dr16N/AN/AN/A29,592 Sq.Ft.1/10/2023Liverpool Ct1743$601,8132,700 Sq.Ft.6/27/2023Livesay Rd4831$250,5741,030 Sq.Ft.5/23/2025Livingston Ave2232$270,6361,336 Sq.Ft.4/18/2025Lloyd Dr7342$408,0002,389 Sq.Ft.7/30/2024Lobdell Ct453$621,5002,903 Sq.Ft.4/14/2021Loblolly Ct1742$469,0001,734 Sq.Ft.10/15/2021Loch Island Dr2043$649,8133,165 Sq.Ft.8/29/2022Lockard Ave11032$328,9231,540 Sq.Ft.5/13/2025Lockhaven St343$384,0001,984 Sq.Ft.5/27/2021Lockheed Ave1032$326,1251,622 Sq.Ft.3/27/2025Locksdale Ct542$489,2501,926 Sq.Ft.7/14/2021Locks Landing Cres2142$390,6191,558 Sq.Ft.11/22/2024Locks Ln332$296,0002,544 Sq.Ft.8/16/2022Locks Lndg5032$395,4261,609 Sq.Ft.3/31/2025Lockspar Ct431$271,0001,124 Sq.Ft.4/29/2024Locks Rd2N/AN/AN/AN/AN/ALodge Cv742$495,0002,242 Sq.Ft.3/16/2023Lofurno Rd5731$255,0741,099 Sq.Ft.5/5/2025Logans Mill Trl4543$415,4751,774 Sq.Ft.3/19/2025Log Fern Ln643$564,4003,028 Sq.Ft.6/30/2023Lola B Ct442$503,7502,253 Sq.Ft.5/22/2023Lolly Pine Ct542$434,2001,804 Sq.Ft.6/20/2023Lombard St6533$362,0181,752 Sq.Ft.4/10/2025Lomond Loop3533$498,2732,726 Sq.Ft.4/24/2025London Plane Crst2432$388,3331,915 Sq.Ft.12/27/2023Long Ave1132$401,8181,521 Sq.Ft.4/3/2025Long Beeches Ave4243$548,1002,666 Sq.Ft.12/5/2023Long Brooke Ct743$530,0002,439 Sq.Ft.6/27/2019Longdale Cres10242$391,0422,184 Sq.Ft.5/5/2025Longdale Ct542$407,6001,941 Sq.Ft.10/16/2024Longhill Arch5153$590,3412,890 Sq.Ft.7/25/2024Longhill Ct753$586,0002,823 Sq.Ft.4/9/2025Longleaf Pl2943$498,9632,645 Sq.Ft.8/9/2024Long Meadow Ln753$644,7142,997 Sq.Ft.8/17/2021Long Parish Way1N/AN/AN/AN/A6/2/2009Longparish Way4633$367,4771,773 Sq.Ft.3/31/2025Long Pt2332$312,1361,560 Sq.Ft.12/16/2024Long Ridge Rd13932$613,3222,349 Sq.Ft.5/28/2025Lookout Ct643$665,0003,098 Sq.Ft.12/21/2023Loose Strife Pl3022$230,7331,148 Sq.Ft.6/24/2024Lord Bradford Ct1143$471,5452,594 Sq.Ft.6/3/20244201 1st StChesapeake, VA 23324
Estimated Value $213,000
Living Area 889 SqFt
Beds 3
Baths 1
Year Built 1940
Property Type Single Family
Ownership Type Corporate
APN 1590000002990
Neighborhood South Norfolk
School District Chesapeake City Public Schools
1235 Woods WayChesapeake, VA 23323
Estimated Value $366,000
Living Area 1,875 SqFt
Beds 3
Baths 2.5
Year Built 1999
Property Type Single Family
Ownership Type Related
APN 0343023001190
Neighborhood Deep Creek
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
4116 Reid StChesapeake, VA 23324
Estimated Value $292,000
Living Area 1,404 SqFt
Beds 3
Baths 2.5
Year Built 2005
Property Type Single Family
Ownership Type Related
APN 1600000001651
Neighborhood South Norfolk
School District Chesapeake City Public Schools
4125 3rd StChesapeake, VA 23324
Estimated Value $218,000
Living Area 924 SqFt
Beds 2
Baths 1
Year Built 1952
Property Type Single Family
Ownership Type Individual
APN 1590000003730
Neighborhood South Norfolk
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
817 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
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
4305 Pickney LnChesapeake, VA 23324
Estimated Value $321,000
Living Area 1,720 SqFt
Beds 3
Baths 2.5
Year Built 2018
Property Type Condominium
Ownership Type Related
APN 1580001000710
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
809 Harbour North DrChesapeake, VA 23320
Estimated Value $192,000
Living Area 1,227 SqFt
Beds 3
Baths 1.5
Year Built 1971
Property Type Townhouse
Ownership Type Corporate
APN 0364003000720
Neighborhood Rivercrest
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
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
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
1824 Warfield StChesapeake, VA 23324
Estimated Value $282,000
Living Area 1,476 SqFt
Beds 3
Baths 2.5
Year Built 2006
Property Type Single Family
Ownership Type Related
APN 1600000002671
Neighborhood South Norfolk
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