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
Unity Ct443$665,2502,796 Sq.Ft.6/9/2017Unser Ct242$460,0001,831 Sq.Ft.5/25/2022Unser Dr2442$472,8751,911 Sq.Ft.7/22/2024Upperville Ct943$619,7783,503 Sq.Ft.4/22/2022Upton Cir1432$260,0711,259 Sq.Ft.8/27/2024Urben Way1N/AN/A$470,000N/A1/14/2005Urquhart St631$239,2501,031 Sq.Ft.9/21/2004Vail Ct1043$571,0002,588 Sq.Ft.4/29/2021Valencia Rd4342$412,5371,831 Sq.Ft.4/28/2025Valera Ct953$552,3333,045 Sq.Ft.9/10/2020Valleyjo Pl1532$313,4671,444 Sq.Ft.12/20/2024Valley Point Cres2043$335,6472,102 Sq.Ft.2/19/2025Valley Stream Rd1232$355,6361,669 Sq.Ft.4/21/2025Valmire Dr3932$376,1081,537 Sq.Ft.5/20/2025Valor Ct1743$529,7062,060 Sq.Ft.5/20/2025Van Buren Ct654$888,5004,236 Sq.Ft.4/23/2021Vance Cir4653$729,9763,390 Sq.Ft.11/6/2024Vanderploeg Dr3832$383,5951,449 Sq.Ft.7/16/2024Vanette Dr3942$491,3682,004 Sq.Ft.10/17/2024Van Luik Ct1233$594,0832,814 Sq.Ft.2/15/2023Varsity Ct943$402,5002,272 Sq.Ft.5/30/2023Varsity Dr1032$310,00011,866 Sq.Ft.7/7/2023Veery St733$372,7141,618 Sq.Ft.5/26/2023Vellen St543$393,6001,740 Sq.Ft.8/29/2006Vellines Ave1831$283,2941,277 Sq.Ft.5/15/2025Velva Dr3531$265,4001,078 Sq.Ft.1/29/2025Venetian Way754$858,0003,833 Sq.Ft.3/10/2021Ventosa Dr2942$547,0002,238 Sq.Ft.4/28/2025Ventures Way17N/AN/AN/A9,718 Sq.Ft.3/27/2025Vepco St3N/AN/AN/A6,771 Sq.Ft.N/AVeranda Way7543$586,8132,557 Sq.Ft.4/16/2025Vera St7N/AN/AN/AN/A6/29/2009Verjac Ter17N/AN/A$361,647N/A12/8/2017Vernon Ct332$266,6671,309 Sq.Ft.10/12/2012Vernon Mills Ct553$532,4002,985 Sq.Ft.2/28/2025Vero St843$388,1251,710 Sq.Ft.3/24/2022Vespasian Cir4353$782,5003,414 Sq.Ft.5/19/2025Vicker Ave3142$328,6922,902 Sq.Ft.5/27/2025Vicksdell Cres1632$440,0632,043 Sq.Ft.3/5/2024Vico Dr1532$374,5331,591 Sq.Ft.6/6/2024Victoria Dr332$417,3331,809 Sq.Ft.2/1/2024Victory Blvd4N/AN/AN/A25,158 Sq.Ft.3/2/2022Vikingfield Ter1042$487,4441,884 Sq.Ft.7/15/2022Villa Ct343$517,3332,227 Sq.Ft.12/24/2024Villa Dr1843$540,5292,434 Sq.Ft.10/19/2023Village Ave2732$373,2001,557 Sq.Ft.10/11/2024Villanova Ave2532$343,0001,729 Sq.Ft.2/10/2025Vinca Ct443$673,7502,518 Sq.Ft.7/2/2024Vincek Way431$334,0003,329 Sq.Ft.10/25/2022Vincent St632$323,3331,594 Sq.Ft.4/28/2025Vine St843$550,1432,665 Sq.Ft.5/4/2023Vineyard Ct854$772,5713,615 Sq.Ft.7/12/2023Vineyard Dr2342$512,9132,072 Sq.Ft.12/2/2024Vinsa Ct643$590,2002,798 Sq.Ft.1/9/2023Vinton Cir653$581,1672,541 Sq.Ft.7/3/2023Violet St6N/AN/A$222,0001,100 Sq.Ft.10/11/2018Virginia Ave5932$315,1901,581 Sq.Ft.3/31/2025Volunteer Trl154$692,0003,691 Sq.Ft.9/30/2011Volvo Penta Dr2N/AN/AN/A52,271 Sq.Ft.N/AVolvo Pkwy17323$331,5407,867 Sq.Ft.5/20/2025Voyager Ct943$587,2223,170 Sq.Ft.4/29/2025Waddell Woods Dr454$704,2503,509 Sq.Ft.9/16/2024Wadena Rd4832$315,8131,450 Sq.Ft.4/11/2025Wade St133$288,0001,442 Sq.Ft.9/9/2021Waitsel Dr7322$308,6341,370 Sq.Ft.3/17/2025Wake Ave4032$283,3421,353 Sq.Ft.3/28/2025Wakedale Arch1143$743,0913,471 Sq.Ft.4/11/2025Walbury Ct542$498,2002,177 Sq.Ft.8/23/2002Walden St3031$270,8621,263 Sq.Ft.9/26/2023Walkers Bend Dr1443$705,0003,426 Sq.Ft.5/30/2017Wallace Ln1621$342,067823 Sq.Ft.6/28/2024Wallboard Dr2N/AN/AN/A11,156 Sq.Ft.11/16/2020Walnut Ave6032$335,6501,574 Sq.Ft.12/4/2024Walnut Forest Ct1353$716,7693,220 Sq.Ft.7/3/2024Walnut Neck Ave2543$681,4403,222 Sq.Ft.4/1/2025Walnut Neck Cir554$746,5003,827 Sq.Ft.7/14/2023Walston Ln3N/AN/AN/AN/AN/AWalston Way1N/AN/AN/AN/AN/AWalton Rd621$335,4001,012 Sq.Ft.2/27/2025Walts Ln1633$402,5001,778 Sq.Ft.4/24/2023Wampler Pl543$465,4002,244 Sq.Ft.11/28/2007Wanchese Ct1242$493,9002,027 Sq.Ft.10/18/2024Warbler Ct2642$231,2311,544 Sq.Ft.N/AWard Rd1N/AN/AN/A4,300 Sq.Ft.12/8/2015Warfield St2333$303,6191,571 Sq.Ft.5/23/2025Warhawks Rd3432$429,4121,815 Sq.Ft.5/28/2025Warren Ave2732$440,5191,760 Sq.Ft.5/12/2025Warrick Rd5643$569,2242,595 Sq.Ft.5/5/2025Warrington Blvd3523$329,5311,739 Sq.Ft.3/19/2025Warwick Cir1032$251,6001,188 Sq.Ft.5/12/2021Washington Dr17442$506,9292,162 Sq.Ft.2/10/2025Watch Island Reach2654$825,0874,232 Sq.Ft.7/28/2022Water Birch Ct442$402,5002,001 Sq.Ft.6/4/2021Watercrest Pl1N/AN/AN/AN/AN/AWater Elm Ct1933$470,2632,288 Sq.Ft.7/19/2023Waterfall Way3153$728,3703,384 Sq.Ft.4/16/2025Waterfern Cv843$549,7502,770 Sq.Ft.5/27/2022Waterfield Ave932$324,4441,445 Sq.Ft.3/14/2023Waterford Ct943$520,1432,291 Sq.Ft.3/8/2023Waterford Dr1242$494,9172,115 Sq.Ft.6/27/20244305 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
4126 4th StChesapeake, VA 23324
Estimated Value $267,000
Living Area 1,586 SqFt
Beds 2
Baths 1.5
Year Built 1946
Property Type Single Family
Ownership Type Individual
APN 1600000000250
Neighborhood South Norfolk
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
1649 Shipyard RdChesapeake, VA 23323
Estimated Value $421,000
Living Area 1,716 SqFt
Beds 4
Baths 2.5
Year Built 2010
Property Type Single Family
Ownership Type Individual
APN 0350000000210
Neighborhood Deep Creek
School District Chesapeake City Public Schools
527 Twine LnChesapeake, VA 23324
Estimated Value $306,000
Living Area 1,442 SqFt
Beds 2
Baths 2.5
Year Built 2015
Property Type Condominium
Ownership Type Individual
APN 1580001000890
Neighborhood South Norfolk
School District Chesapeake City Public Schools
1404 Earle AveChesapeake, VA 23324
Estimated Value $287,000
Living Area 1,828 SqFt
Beds 3
Baths 2
Year Built 1948
Property Type Single Family
Ownership Type Individual
APN 1590000003460
Neighborhood South Norfolk
School District Chesapeake City Public Schools
4136 2nd StChesapeake, VA 23324
Estimated Value $238,000
Living Area 1,040 SqFt
Beds 3
Baths 2
Year Built 1991
Property Type Single Family
Ownership Type Corporate
APN 1590000002800
Neighborhood South Norfolk
School District Chesapeake City Public Schools
923 Gene CresChesapeake, VA 23320
Estimated Value $289,000
Living Area 1,224 SqFt
Beds 3
Baths 1
Year Built 1958
Property Type Single Family
Ownership Type Individual
APN 0271002000430
Neighborhood Rivercrest
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
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
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
1333 Winslow AveChesapeake, VA 23323
Estimated Value $329,000
Living Area 1,500 SqFt
Beds 4
Baths 2
Year Built 1977
Property Type Single Family
Ownership Type Individual
APN 0255002000130
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
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
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
824 Hardwood DrChesapeake, VA 23320
Estimated Value $452,000
Living Area 2,253 SqFt
Beds 4
Baths 2.5
Year Built 1990
Property Type Single Family
Ownership Type Related
APN 0369001000430
Neighborhood Rivercrest
School District Chesapeake City Public Schools