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
Whitlock Ct642$336,1671,719 Sq.Ft.5/18/2017Whitman St4123$293,2821,314 Sq.Ft.5/30/2025Whitney Ct543$514,4002,076 Sq.Ft.4/28/2005Whittamore Rd6632$393,0961,657 Sq.Ft.12/16/2024Wickford Ct4421$207,6141,021 Sq.Ft.1/2/2025Wickford Dr9121$207,1891,007 Sq.Ft.4/11/2025Wickwood Ct643$599,8333,030 Sq.Ft.5/8/2024Wickwood Dr7443$601,3152,823 Sq.Ft.5/10/2024Widgeon Ct9N/AN/AN/AN/AN/AWilbur Ave4631$283,5781,472 Sq.Ft.3/3/2025Wilcox St13N/A2$210,0003,549 Sq.Ft.5/12/2017Wild Cherry Ct942$486,2501,844 Sq.Ft.7/8/2022Wild Duck Cir443$553,2502,756 Sq.Ft.12/7/2022Wild Duck Xing4443$554,2732,649 Sq.Ft.8/28/2024Wild Horse Rdg1942$655,3752,404 Sq.Ft.8/17/2023Wildlife Trce3243$639,6452,900 Sq.Ft.9/27/2024Wild Turkey Ct553$684,0002,846 Sq.Ft.11/9/2022Wildwood Rd3332$312,0311,549 Sq.Ft.8/30/2024Wilkins Ln1N/AN/AN/AN/A11/27/2012Willa Mae Ct454$625,6673,327 Sq.Ft.4/17/2024Willard Dr4032$416,5001,673 Sq.Ft.11/19/2024William Clarke Ct1132$348,3641,509 Sq.Ft.7/30/2024William Crst643$526,3332,571 Sq.Ft.1/9/2023William Hall Way3353$641,7782,788 Sq.Ft.4/28/2023Williams Ave1232$293,5001,337 Sq.Ft.1/24/2025Williamsburg Dr532$305,5007,556 Sq.Ft.7/25/2024Williamsburg Sq1N/AN/AN/A20,620 Sq.Ft.N/AWilliamson St5132$292,7551,567 Sq.Ft.4/17/2025Willis St2532$285,2272,627 Sq.Ft.5/3/2024Willow Arch543$465,7502,032 Sq.Ft.10/5/2022Willow Ave12932$315,9761,600 Sq.Ft.1/24/2025Willow Bend Ct1142$414,2731,890 Sq.Ft.6/20/2023Willow Bend Dr12642$406,0681,809 Sq.Ft.4/9/2025Willow Brook Ct643$535,2002,658 Sq.Ft.4/11/2024Willow Brook Rd4043$521,0812,577 Sq.Ft.9/14/2023Willow Brook Way1443$523,9232,406 Sq.Ft.9/23/2021Willow Creek Ct743$519,1432,625 Sq.Ft.10/26/2021Willow Green Ct4122$228,9511,148 Sq.Ft.5/22/2025Willow Lake Rd4042$483,9062,048 Sq.Ft.1/24/2025Willow Lakes Ct743$563,0002,380 Sq.Ft.9/27/2024Willow Oak Dr4942$481,9361,866 Sq.Ft.12/19/2024Willow Point Arch9222$236,5511,207 Sq.Ft.1/24/2025Willows Arch832$370,5001,787 Sq.Ft.4/22/2021Willow Spire Arch1153$680,1003,533 Sq.Ft.6/2/2020Willowstone Arch1042$482,0002,281 Sq.Ft.12/19/2024Willowstone Ct442$475,0002,166 Sq.Ft.5/24/2022Willowwood Ct331$301,6671,330 Sq.Ft.N/AWillowwood Dr2332$319,0001,344 Sq.Ft.9/24/2024Will Scarlet Way443$525,0002,675 Sq.Ft.4/14/2025Wilmington Ave28N/AN/A$499,429N/AN/AWilrose Trce1042$519,0002,218 Sq.Ft.3/10/2025Wilshire St1033$361,1001,750 Sq.Ft.11/15/2024Wilson Dr2442$446,5652,183 Sq.Ft.5/13/2024Wilson Rd1331$256,00015,547 Sq.Ft.3/29/2021Wilson Spruce Ct532$374,2501,776 Sq.Ft.4/30/2021Wilton St1932$242,5561,274 Sq.Ft.5/28/2025Wimbledon Chase7122$198,3711,036 Sq.Ft.3/31/2025Wimbledon Sq15N/AN/AN/A3,204 Sq.Ft.1/4/2023Wimbley Ln1143$517,5452,363 Sq.Ft.5/24/2022Winchester Way2843$652,9232,960 Sq.Ft.6/22/2021Windlesham Dr1543$576,2862,492 Sq.Ft.3/21/2025Windmill Pt1733$329,3531,722 Sq.Ft.7/26/2022Windom Blvd633$406,0002,225 Sq.Ft.9/11/2023Windsong Ct533$453,2502,747 Sq.Ft.4/18/2023Windsor Pt1043$601,4002,941 Sq.Ft.2/27/2024Windsor Rd1432$405,3851,452 Sq.Ft.12/17/2021Windswept Cir6642$499,3502,337 Sq.Ft.8/14/2024Windward Dr4742$450,6592,034 Sq.Ft.1/24/2025Windy Oak Run742$356,7141,721 Sq.Ft.6/23/2020Windy Pine Ln133$582,0003,244 Sq.Ft.6/23/2016Windy Rd1832$309,5292,999 Sq.Ft.4/23/2025Winery Dr2743$398,1601,912 Sq.Ft.5/26/2023Winfall Dr3542$498,5452,066 Sq.Ft.4/1/2024Winged Foot Ct3322$318,2191,499 Sq.Ft.4/3/2025Wingfield Ave14832$293,4861,455 Sq.Ft.5/28/2025Winnie Dr1353$545,6002,924 Sq.Ft.2/21/2023Winscott Ct1042$480,9001,882 Sq.Ft.4/21/2025Winsford Ln2533$383,1201,776 Sq.Ft.5/14/2025Winslow Ave5232$327,8601,421 Sq.Ft.7/31/2024Winston Ter642$408,3332,024 Sq.Ft.8/27/2019Winterberry Ct542$526,2502,012 Sq.Ft.9/9/2021Wintercress Way1N/AN/AN/A264,213 Sq.Ft.3/16/2021Wintergreen Dr2932$309,6431,494 Sq.Ft.4/14/2025Winterhawk Ct1432$390,0001,520 Sq.Ft.9/20/2023Winter Jasmine Ct443$486,5002,292 Sq.Ft.7/20/2021Winter King Ct843$477,8751,973 Sq.Ft.2/10/2023Winter Stone Ct643$514,3332,626 Sq.Ft.4/29/2021Winterwater Ct1143$525,9092,653 Sq.Ft.10/6/2023Winterwood Ct743$500,8572,388 Sq.Ft.2/19/2025Winter Wren Ln3032$277,5671,802 Sq.Ft.N/AWinwood Dr2032$395,7001,751 Sq.Ft.9/27/2024Wisdom Path13843$670,7022,914 Sq.Ft.5/8/2025Wisecamp Ct932$390,7781,637 Sq.Ft.10/19/2023Wise St432$344,7501,542 Sq.Ft.1/7/2021Wisteria Ct543$469,4002,421 Sq.Ft.2/19/2024Witt Ct633$406,5002,227 Sq.Ft.5/31/2023Wittington Dr4143$530,7572,257 Sq.Ft.5/30/2025W Lake Cir1N/AN/AN/A1,614 Sq.Ft.N/AWoodards Ford Rd5644$1,025,0194,631 Sq.Ft.4/23/2024Wood Ave4432$313,2331,629 Sq.Ft.9/19/20241855 Doubloon WayChesapeake, VA 23323
Estimated Value $407,000
Living Area 1,875 SqFt
Beds 3
Baths 2.5
Year Built 2018
Property Type Condominium
Ownership Type Related
APN 0354003001450
Neighborhood Deep Creek
School District Chesapeake City Public Schools
1002 Godwin AveChesapeake, VA 23324
Estimated Value $364,000
Living Area 1,924 SqFt
Beds 4
Baths 2.5
Year Built 2013
Property Type Single Family
Ownership Type Individual
APN 1520000002620
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
504 Rosewood TerChesapeake, VA 23320
Estimated Value $412,000
Living Area 1,629 SqFt
Beds 3
Baths 1.5
Year Built 1966
Property Type Single Family
Ownership Type Related
APN 0361008000890
Neighborhood Rivercrest
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
1204 Corden AveChesapeake, VA 23324
Estimated Value $243,000
Living Area 1,645 SqFt
Beds 3
Baths 1
Year Built 1948
Property Type Single Family
Ownership Type Individual
APN 1590000001070
Neighborhood South Norfolk
School District Chesapeake City Public Schools
1819 Sunsprite LoopChesapeake, VA 23323
Estimated Value $612,000
Living Area 2,924 SqFt
Beds 4
Baths 2.5
Year Built 2007
Property Type Single Family
Ownership Type Related
APN 0354001000110
Neighborhood Deep Creek
School District Chesapeake City Public Schools
1337 Dominion Lakes BlvdChesapeake, VA 23320
Estimated Value $625,000
Living Area 3,028 SqFt
Beds 5
Baths 2.5
Year Built 2002
Property Type Single Family
Ownership Type Related
APN 0352001000250
Neighborhood Rivercrest
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
1119 Railroad AveChesapeake, VA 23324
Estimated Value $239,000
Living Area 1,197 SqFt
Beds 3
Baths 2
Year Built 1960
Property Type Single Family
Ownership Type Individual
APN 1660000000060
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
320 Esplanade PlChesapeake, VA 23320
Estimated Value $311,000
Living Area 1,352 SqFt
Beds 2
Baths 2.5
Year Built 1993
Property Type Townhouse
Ownership Type Related
APN 0367008000150
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
1708 Kinser CtChesapeake, VA 23324
Estimated Value $422,000
Living Area 2,432 SqFt
Beds 4
Baths 2.5
Year Built 2003
Property Type Single Family
Ownership Type Individual
APN 1521001000080
Neighborhood South Norfolk
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
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