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
Pine Grove Ln5943$612,2933,207 Sq.Ft.3/4/2025Pine Grove Lndg1643$540,1332,329 Sq.Ft.10/13/2021Pine Hill Cres2432$305,3751,362 Sq.Ft.3/20/2024Pinehurst Dr1132$388,2731,837 Sq.Ft.5/30/2025Pine Island Quay1453$631,3083,407 Sq.Ft.10/18/2023Pine Level Ln1532$441,8671,547 Sq.Ft.10/26/2021Pineridge Ct633$434,6672,332 Sq.Ft.6/17/2023Pineridge Dr2642$450,6002,305 Sq.Ft.2/13/2025Pines Ct743$449,7142,093 Sq.Ft.3/31/2023Pines Of Warrick Dr1043$510,6672,432 Sq.Ft.2/19/2023Pine Valley Run1N/AN/AN/A104,312 Sq.Ft.10/27/2020Pine View Ct1332$270,7691,418 Sq.Ft.8/20/2024Pine View Ln2131$250,2861,133 Sq.Ft.7/24/2024Pine Wood Ct1033$271,8001,454 Sq.Ft.3/13/2025Pine Wood Run131$236,000N/A11/9/2020Pinmaul Arch643$541,3332,601 Sq.Ft.6/6/2023Pin Oak Pl1142$480,2731,912 Sq.Ft.12/12/2024Pino Ct743$548,0002,398 Sq.Ft.7/28/2023Pinta Dr2532$375,0801,541 Sq.Ft.11/27/2024Pintail Ln3342$402,4241,898 Sq.Ft.5/8/2024Pioneer Ln1642$468,3082,015 Sq.Ft.9/5/2024Piping Rock Dr2153$637,8953,000 Sq.Ft.11/18/2024Pitchback Ln1143$557,3332,953 Sq.Ft.10/10/2023Pitt Saw Ln1743$488,3852,207 Sq.Ft.6/23/2022Pittway Ct843$500,0002,349 Sq.Ft.9/1/2020Placid Ct1243$568,8182,701 Sq.Ft.9/23/2024Placid Way3242$521,3672,451 Sq.Ft.8/28/2024Plainfield Ave2732$383,5001,671 Sq.Ft.6/20/2023Plane Tree Mews433$413,0002,195 Sq.Ft.9/25/2017Plank Rd2N/AN/AN/AN/AN/APlantation Dr3131$312,4831,390 Sq.Ft.9/29/2023Plantation Lakes Cir18243$552,2392,709 Sq.Ft.10/18/2024Plantation Woods Way2143$573,1672,913 Sq.Ft.7/11/2024Plantation Xing1N/AN/AN/AN/AN/APleasant Ridge Ct743$688,6672,937 Sq.Ft.3/17/2023Pleasant Ridge Dr3543$711,3332,949 Sq.Ft.4/29/2025Pleasant Way2943$549,5932,210 Sq.Ft.7/7/2023Pleasure St1332$260,3751,265 Sq.Ft.5/10/2017Plover Ct442$544,0002,621 Sq.Ft.12/16/2024Plow Ln1242$245,4171,624 Sq.Ft.8/18/2021Plumlee Dr2232$287,0001,445 Sq.Ft.4/15/2025Plum Ln943$480,5002,567 Sq.Ft.7/20/2022Plummer Dr5232$356,8401,540 Sq.Ft.10/17/2024Pocahontas Ave231$176,5001,239 Sq.Ft.2/11/2013Pocaty Creek Ln733$740,7142,690 Sq.Ft.1/22/2025Pocaty Rd6542$532,2441,998 Sq.Ft.11/14/2024Pods Way2N/AN/AN/A30,321 Sq.Ft.5/28/2013Poindexter St8221$209,8333,820 Sq.Ft.10/21/2024Point Ct432$368,2501,605 Sq.Ft.12/14/2023Point Dr7632$388,5001,679 Sq.Ft.6/3/2025Point Elizabeth Ct332$366,3331,572 Sq.Ft.7/22/2012Point Elizabeth Dr6543$490,0002,350 Sq.Ft.10/4/2024Pointers Trl543$524,4002,740 Sq.Ft.12/9/2022Point Harbor Ct842$409,2501,943 Sq.Ft.9/10/2020Point Reel Rd1332$328,0771,569 Sq.Ft.8/8/2024Pompano Arch1153$671,7002,947 Sq.Ft.9/7/2021Ponce Ct543$721,0003,333 Sq.Ft.12/21/2021Pond Ln2242$256,8501,399 Sq.Ft.5/7/2025Poplar Ave2842$336,9131,878 Sq.Ft.10/5/2022Poplar Forest Ct1853$760,4443,757 Sq.Ft.6/11/2021Poplar Hill Ct653$548,0002,781 Sq.Ft.7/29/2022Poplar Hill Rd5443$523,5244,703 Sq.Ft.5/8/2025Poplar Ridge Ct342$483,0002,018 Sq.Ft.2/28/2024Poplar Ridge Dr2442$482,3912,026 Sq.Ft.1/16/2024Poquoson Cir544$731,8003,652 Sq.Ft.8/20/2021Poquoson Xing4343$696,1863,458 Sq.Ft.3/27/2025Portal Rd1332$296,7691,532 Sq.Ft.8/9/2023Port Chambers Ct432$317,0001,336 Sq.Ft.2/27/2024Porte Crayon St1443$555,6672,487 Sq.Ft.5/20/2022Porter St2732$264,9571,428 Sq.Ft.11/20/2024Portland St2932$289,5361,537 Sq.Ft.11/16/2023Portlock Rd8932$284,5951,670 Sq.Ft.5/19/2025Portobello Ct442$296,0001,176 Sq.Ft.4/27/2018Port Rd4532$300,4651,319 Sq.Ft.2/18/2025Port Side Way1533$428,4672,124 Sq.Ft.6/28/2022Ports Lndg742$422,8571,852 Sq.Ft.3/9/2022Portsmouth Blvd10631$348,79433,734 Sq.Ft.3/11/2025Post Ave2332$329,5002,106 Sq.Ft.3/12/2024Potter Rd2832$311,4811,391 Sq.Ft.10/30/2024Powell Cir3332$298,0001,439 Sq.Ft.4/24/2024Powhatan Sq343$417,0001,983 Sq.Ft.4/22/2024Pratt St6N/AN/AN/A127,500 Sq.Ft.11/28/2016Precon Dr10N/AN/AN/A35,974 Sq.Ft.4/28/2022Prentiss Dr1432$502,6432,131 Sq.Ft.2/26/2021Prescott Cir2232$345,1821,523 Sq.Ft.3/8/2024Preservation Loop743$638,1433,006 Sq.Ft.11/6/2023Preservation Reach5843$646,5272,905 Sq.Ft.5/22/2025Preston Arch1142$459,0002,148 Sq.Ft.7/22/2024Prestwick Ct854$987,1434,314 Sq.Ft.11/9/2020Price Ct632$377,1671,591 Sq.Ft.11/30/2010Primrose Ln6022$233,1531,162 Sq.Ft.6/3/2025Prince Andrew Ct1143$400,6252,180 Sq.Ft.3/11/2025Prince Charles Dr543$633,4002,684 Sq.Ft.5/6/2022Prince Edward Dr1943$625,7782,599 Sq.Ft.12/19/2023Prince George Ct943$381,0002,095 Sq.Ft.3/12/2024Prince John Ct943$401,2222,190 Sq.Ft.5/7/2019Prince Michael Ct933$386,1672,088 Sq.Ft.4/30/2024Prince Of Wales Ct453$522,5002,774 Sq.Ft.11/20/2024Prince Of Wales Dr1942$477,7222,602 Sq.Ft.6/6/2024Prince Phillip Ct943$397,8892,227 Sq.Ft.6/11/20211100 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
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
1741 Fortune TerChesapeake, VA 23323
Estimated Value $418,000
Living Area 2,036 SqFt
Beds 3
Baths 2.5
Year Built 2022
Property Type Condominium
Ownership Type Related
APN 0354003003750
Neighborhood Deep Creek
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
1412 Anthony DrChesapeake, VA 23320
Estimated Value $333,000
Living Area 1,500 SqFt
Beds 3
Baths 2.5
Year Built 1984
Property Type Single Family
Ownership Type Individual
APN 0272001001390
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1205 Bramblewood CtChesapeake, VA 23323
Estimated Value $334,000
Living Area 425 SqFt
Beds 1
Baths 1
Year Built 1980
Property Type Single Family
Ownership Type Individual
APN 0343013000100
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
902 Godwin AveChesapeake, VA 23324
Estimated Value $364,000
Living Area 1,972 SqFt
Beds 4
Baths 3
Year Built 2018
Property Type Single Family
Ownership Type Related
APN 1510000000720
Neighborhood South Norfolk
School District Chesapeake City Public Schools
708 Bulrush CtChesapeake, VA 23320
Estimated Value $471,000
Living Area 2,189 SqFt
Beds 4
Baths 2.5
Year Built 1991
Property Type Single Family
Ownership Type Individual
APN 0369001000470
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1245 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
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
304 Primrose LnChesapeake, VA 23320
Estimated Value $224,000
Living Area 1,053 SqFt
Beds 2
Baths 2
Year Built 1994
Property Type Condominium
Ownership Type Individual
APN 0367010000030
Neighborhood Rivercrest
School District Chesapeake City Public Schools
703 Durham AveChesapeake, VA 23320
Estimated Value $408,000
Living Area 2,501 SqFt
Beds 4
Baths 2.5
Year Built 2002
Property Type Single Family
Ownership Type Related
APN 0351004003070
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1401 Glendale AveChesapeake, VA 23323
Estimated Value $311,000
Living Area 1,360 SqFt
Beds 3
Baths 2
Year Built 1977
Property Type Single Family
Ownership Type Individual
APN 0255001002870
Neighborhood Deep Creek
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
1317 Great Bridge BlvdChesapeake, VA 23320
Estimated Value $276,000
Living Area 1,657 SqFt
Beds 3
Baths 2
Year Built 1955
Property Type Single Family
Ownership Type Related
APN 0362001000640
Neighborhood Rivercrest
School District Chesapeake City Public Schools