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
Regina Way222$272,0001,650 Sq.Ft.9/23/2015Reid St4632$271,3724,159 Sq.Ft.3/27/2025Rellen Ct642$545,8332,616 Sq.Ft.3/18/2022Rellen St2442$509,3482,287 Sq.Ft.4/24/2025Remington Ct543$511,0002,178 Sq.Ft.8/19/2020Remington Dr2843$523,8152,290 Sq.Ft.10/26/2024Renaissance Ct532$436,8001,949 Sq.Ft.10/23/2018Renan Arch653$689,3333,271 Sq.Ft.4/24/2025Renee Ln1053$707,0003,172 Sq.Ft.1/25/2022Renwood Ct543$770,8003,242 Sq.Ft.6/11/2019Repose Ln3833$490,7112,190 Sq.Ft.10/18/2024Republic Rd5N/AN/AN/A4,209 Sq.Ft.8/11/2004Research Dr8N/AN/AN/A7,226 Sq.Ft.3/5/2015Reservation Rd3N/AN/AN/A5,206 Sq.Ft.N/AReserve Trl1643$634,5003,097 Sq.Ft.5/22/2025Resh Ct542$462,2001,887 Sq.Ft.3/15/2022Resource Row4N/AN/AN/A92,861 Sq.Ft.12/20/2018Reunion St2633$323,0431,676 Sq.Ft.2/4/2025Revella Arch753$772,1433,606 Sq.Ft.4/8/2025Revenge Way933$396,4441,754 Sq.Ft.4/21/2025Rex Cir6222$266,3101,497 Sq.Ft.4/28/2025Rhema Rd1243$507,2222,428 Sq.Ft.4/10/2024Rhodes St2632$276,6801,351 Sq.Ft.3/25/2025Ricardo Ct343$940,6673,971 Sq.Ft.6/27/2024Rice St432$271,6671,321 Sq.Ft.2/7/2024Richmond Ave722$234,8571,044 Sq.Ft.1/8/2025Richwood Ave2143$419,0002,255 Sq.Ft.5/16/2025Ricka Ct1042$463,9001,925 Sq.Ft.4/3/2023Rick Fletcher Ct954$703,2223,756 Sq.Ft.5/5/2020Ricks Ct544$407,7502,592 Sq.Ft.11/27/2023Riddick St1232$309,1821,649 Sq.Ft.3/13/2024Riddlehurst Ave1643$652,9333,143 Sq.Ft.9/9/2024Ridgeboard Pl1353$525,5382,749 Sq.Ft.4/18/2025Ridge Cir11523$235,6751,254 Sq.Ft.1/15/2025Ridgeline Pt643$460,3332,582 Sq.Ft.9/22/2020Ridgeway Ave832$391,6002,128 Sq.Ft.9/20/2022Ridgewood Ct1532$343,3571,615 Sq.Ft.10/14/2024Ridgewood Rd3742$309,5951,338 Sq.Ft.2/24/2025Riding Path Way1043$595,6672,901 Sq.Ft.8/3/2020Riley Dr1653$729,2503,381 Sq.Ft.4/14/2025Ring Rd7N/AN/AN/A99,054 Sq.Ft.3/31/2025Ringtail Ct743$618,7142,681 Sq.Ft.5/16/2025Rio Dr3942$528,2942,308 Sq.Ft.5/13/2024Rio Mar Ct243$555,0002,435 Sq.Ft.6/26/2023Ripley St632$390,0001,784 Sq.Ft.3/25/2019Riston Ct643$589,0002,705 Sq.Ft.5/24/2024Rivanna River Reach7622$293,0391,385 Sq.Ft.5/27/2025River Arch Ct532$449,5001,954 Sq.Ft.3/7/2018River Arch Dr3232$448,0001,960 Sq.Ft.3/13/2024River Birch Ct2232$298,0001,533 Sq.Ft.8/11/2023River Birch Run6732$266,8393,563 Sq.Ft.2/20/2024River Breeze Cir11043$337,1412,120 Sq.Ft.5/20/2025River Creek Rd5732$287,2461,283 Sq.Ft.11/25/2024Rivercrest Pl433$372,0002,033 Sq.Ft.3/29/2023Rivercrest Way933$337,0002,033 Sq.Ft.4/25/2023River Dr3932$397,1051,882 Sq.Ft.3/26/2025River Gate Ct543$688,8003,145 Sq.Ft.7/31/2017River Gate Rd5343$722,9413,289 Sq.Ft.5/24/2024River Hollow Ct1043$567,1432,610 Sq.Ft.3/4/2023River Oaks Dr6342$431,5932,177 Sq.Ft.8/20/2024River Pearl Way5643$543,4262,644 Sq.Ft.8/2/2024River Rock Reach653$729,1673,723 Sq.Ft.3/4/2025Rivers Edge Cv353$552,3333,618 Sq.Ft.10/21/2022Rivers Edge Trce3153$534,5933,069 Sq.Ft.4/28/2025Riverside Dr1433$352,6671,938 Sq.Ft.9/9/2024Riverstone Way1243$494,3332,808 Sq.Ft.8/16/2019River Strand3954$762,2973,698 Sq.Ft.4/30/2024River Strnd1N/AN/AN/AN/AN/ARiverton Ct643$524,6002,508 Sq.Ft.4/21/2025Riverton Way743$522,0002,458 Sq.Ft.6/29/2021River Walk Pkwy10N/AN/A$156,00017,146 Sq.Ft.7/24/2019Riverwood Cres3543$696,9382,807 Sq.Ft.1/31/2025Riviara Pl3453$764,1383,456 Sq.Ft.1/12/2024Rixtown Ct543$552,2002,454 Sq.Ft.7/23/2021Roanoke Arch1942$519,5262,176 Sq.Ft.4/24/2025Roanoke Ct443$514,7502,122 Sq.Ft.2/22/2022Robert Ct343$547,0002,548 Sq.Ft.9/30/2010Robert Frost Rd2643$546,5792,497 Sq.Ft.4/18/2024Robert Hall Blvd6N/AN/A$2,246,00067,615 Sq.Ft.3/31/2021Robert Hall Ct2N/AN/AN/A25,670 Sq.Ft.N/ARobertson Blvd1721$177,0001,958 Sq.Ft.5/28/2021Robert St1532$483,1542,029 Sq.Ft.12/27/2024Robert Welch Ct653$550,2003,114 Sq.Ft.12/5/2017Robert Welch Ln2843$530,7692,854 Sq.Ft.9/26/2023Robin Ct442$477,0002,067 Sq.Ft.8/8/2023Robinhood Rd1843$555,6112,611 Sq.Ft.8/28/2024Robinold Ct542$475,0001,826 Sq.Ft.2/3/2020Roble Ct642$532,0002,224 Sq.Ft.1/9/2025Rochelle Ct743$498,1432,567 Sq.Ft.1/25/2023Rockbridge Ct642$445,0002,133 Sq.Ft.11/26/2024Rock Bridge Mews5322$204,080954 Sq.Ft.12/19/2024Rock Cliff Reach1622$199,750920 Sq.Ft.4/28/2025Rock Creek Ct443$411,0002,587 Sq.Ft.N/ARock Creek Dr9043$407,0892,428 Sq.Ft.11/4/2024Rock Dr4732$366,4091,788 Sq.Ft.10/22/2024Rockglen Cir954$759,4443,625 Sq.Ft.3/2/2022Rockglen Ct853$804,5713,838 Sq.Ft.2/24/2023Rockies Ct1353$634,1672,877 Sq.Ft.8/27/2024Rockland Ct943$528,3332,380 Sq.Ft.9/17/2021Rockland Ter943$536,4442,492 Sq.Ft.5/1/2017954 Railroad AveChesapeake, VA 23324
Estimated Value $319,000
Living Area 1,888 SqFt
Beds 4
Baths 2.5
Year Built 2009
Property Type Single Family
Ownership Type Related
APN 1600000000940
Neighborhood South Norfolk
School District Chesapeake City Public Schools
4374 Pickney LnChesapeake, VA 23324
Estimated Value $327,000
Living Area 1,760 SqFt
Beds 3
Baths 2.5
Year Built 2016
Property Type Condominium
Ownership Type Individual
APN 1580001001170
Neighborhood South Norfolk
School District Chesapeake City Public Schools
832 Wickford DrChesapeake, VA 23320
Estimated Value $186,000
Living Area 860 SqFt
Beds 2
Baths 1
Year Built 1985
Property Type Townhouse
Ownership Type Individual
APN 0367001000330
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
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
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
113 Ford StChesapeake, VA 23323
Estimated Value $246,000
Living Area 1,040 SqFt
Beds 3
Baths 2
Year Built 2001
Property Type Single Family
Ownership Type Related
APN 0261002000700
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
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
1301 Pinecroft LnChesapeake, VA 23323
Estimated Value $341,000
Living Area 1,543 SqFt
Beds 3
Baths 2
Year Built 1999
Property Type Single Family
Ownership Type Individual
APN 0343023000470
Neighborhood Deep Creek
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
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
1855 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
838 Rivanna River ReachChesapeake, VA 23320
Estimated Value $283,000
Living Area 1,350 SqFt
Beds 2
Baths 2
Year Built 1989
Property Type Condominium
Ownership Type Individual
APN 0367003000190
Neighborhood Rivercrest
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
906 Parley PlChesapeake, VA 23323
Estimated Value $417,000
Living Area 2,036 SqFt
Beds 3
Baths 2.5
Year Built 2018
Property Type Condominium
Ownership Type Individual
APN 0354003000120
Neighborhood Deep Creek
School District Chesapeake City Public Schools