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
Painted Lady Pl3153$677,9093,060 Sq.Ft.3/25/2025Palladium Ave1N/AN/AN/AN/AN/APalomino Ct553$738,0003,555 Sq.Ft.12/20/2024Pamela Ct2N/AN/AN/A24,739 Sq.Ft.12/5/2022Pamlico Blvd4442$442,8601,833 Sq.Ft.5/16/2025Pamona St11N/AN/A$237,750100 Sq.Ft.2/3/2025Pamunkey River Ct422$223,0001,042 Sq.Ft.9/10/2021Papaya Pl1N/AN/AN/AN/AN/APaperbark Trl1042$386,1001,853 Sq.Ft.11/1/2024Paradisio Way754$787,8573,873 Sq.Ft.5/10/2022Paramont Ave3632$327,0673,490 Sq.Ft.4/10/2025Parapet Ct1242$339,7501,812 Sq.Ft.7/9/2021Parapet Rd2842$336,3931,799 Sq.Ft.8/27/2024Park Ave6032$271,7063,255 Sq.Ft.10/3/2024Park Ct16N/AN/AN/A5,650 Sq.Ft.11/15/2021Parkdale St754$754,8573,106 Sq.Ft.2/24/2025Parker Rd11542$512,7432,219 Sq.Ft.6/20/2024Parkerson Ln631$386,5001,603 Sq.Ft.5/2/2018Parklawn Ave1N/AN/A$373,000N/A11/11/2020Parkley Dr2633$382,7501,870 Sq.Ft.2/13/2025Park Row1741$262,0001,321 Sq.Ft.10/18/2021Parkside Dr1032$467,50012,920 Sq.Ft.5/6/2022Parkview Dr2N/AN/AN/A42,573 Sq.Ft.6/2/2021Parkway Rd833$489,3752,372 Sq.Ft.7/27/2024Parley Pl1633$441,4672,297 Sq.Ft.9/26/2023Parr Ln3542$443,6572,003 Sq.Ft.5/21/2025Partridge Ave6232$239,4751,171 Sq.Ft.4/21/2025Pasture Pl334$469,6672,254 Sq.Ft.3/27/2025Patrick Henry Dr4843$513,9252,393 Sq.Ft.5/21/2025Patrick St963$226,6673,674 Sq.Ft.4/6/2022Patriot Ln842$391,0002,127 Sq.Ft.2/6/2008Pattie Ln2032$379,1001,653 Sq.Ft.10/13/2023Patton Pl832$356,1251,657 Sq.Ft.11/26/2019Paula Dr1032$622,1252,723 Sq.Ft.10/2/2024Paul Eason Dr1545$1,485,8465,140 Sq.Ft.9/15/2023Pavilion Dr2N/AN/AN/A5,728 Sq.Ft.11/10/2020Pawnee Hwy1N/AN/A$204,000N/AN/APawnee St2N/AN/A$236,500N/A6/10/2021Paw Paw Pl35N/AN/A$451,882N/A10/23/2024Paxson Ave1931$289,6321,505 Sq.Ft.11/13/2024Payne Rd3531$253,9141,113 Sq.Ft.4/18/2024Peaceful Rd2843$772,3753,014 Sq.Ft.8/26/2024Peach Rd1432$516,2002,104 Sq.Ft.4/30/2022Peachtree Dr1742$491,7061,913 Sq.Ft.9/23/2024Pearl St1743$332,5712,107 Sq.Ft.2/17/2025Pebble Quay543$656,7503,279 Sq.Ft.1/10/2022Pebble Rock Ct743$554,5002,531 Sq.Ft.6/21/2021Pecan Forest Ct754$723,8333,603 Sq.Ft.2/17/2025Pecan Point Ct553$529,4002,589 Sq.Ft.3/9/2021Pecks Arch843$654,3332,804 Sq.Ft.3/24/2023Peek Trl1432$382,00016,559 Sq.Ft.4/26/2023Pelham St2031$280,7001,319 Sq.Ft.8/5/2024Pelican Cir942$541,0002,242 Sq.Ft.8/22/2024Pendragon Ct1232$352,5001,784 Sq.Ft.7/6/2023Penhook Ct532$473,8002,142 Sq.Ft.4/11/2025Pennsylvania Ave1N/AN/AN/AN/AN/APenny Ln1132$507,0002,102 Sq.Ft.10/22/2021Penrose Ln1543$570,7692,104 Sq.Ft.8/9/2023Penryth Ct753$633,7503,191 Sq.Ft.5/17/2024Penton Mews3433$362,0911,786 Sq.Ft.3/7/2025Penzance Cir1232$263,9171,242 Sq.Ft.8/18/2023Peoples Rd1232$636,1002,501 Sq.Ft.3/18/2022Pepper Cir543$662,0002,947 Sq.Ft.8/6/2015Peppercorn Dr1343$517,7002,516 Sq.Ft.8/25/2021Peppercorn Way5732$278,8931,671 Sq.Ft.2/24/2025Pepper Ridge Ct3032$240,3791,488 Sq.Ft.2/18/2025Pepper Tree Ln244$708,0003,259 Sq.Ft.N/APepperwood Dr343$458,3332,073 Sq.Ft.1/21/2021Percheron Ct932$471,2221,872 Sq.Ft.12/19/2022Perdue Ln1032$348,2001,740 Sq.Ft.3/29/2017Peren Ave932$407,7501,457 Sq.Ft.5/15/2023Pernell Ln1243$619,1002,600 Sq.Ft.2/24/2025Perry St6531$251,9641,360 Sq.Ft.5/30/2025Pershing Ct743$496,5712,761 Sq.Ft.1/7/2022Pescado Ct254$668,0003,960 Sq.Ft.1/22/2018Petre Rd832$298,0001,207 Sq.Ft.8/21/2023Peyton Ln1554$1,039,2864,577 Sq.Ft.10/17/2024Phalarope St1043$494,6002,517 Sq.Ft.2/28/2024Pheasant Way653$499,2002,563 Sq.Ft.4/25/2025Philadelphia St543$345,6001,738 Sq.Ft.9/11/2024Phillips St1N/AN/AN/AN/AN/APhilmont Ave4132$321,0001,530 Sq.Ft.10/21/2024Phoenix Dr1743$532,2502,468 Sq.Ft.6/2/2025Phyllis Dr2532$341,7501,702 Sq.Ft.4/28/2025Picadilly Ct342$565,6672,420 Sq.Ft.3/27/2023Pickney Ln3233$325,4671,759 Sq.Ft.5/12/2025Piedmont Arch1743$590,4002,881 Sq.Ft.3/7/2024Pierce Ln2232$320,3811,425 Sq.Ft.4/22/2025Pierside Lndg454$701,5003,617 Sq.Ft.5/12/2022Piers Lndg1042$393,4441,600 Sq.Ft.7/19/2021Pile Ave2643$397,5002,151 Sq.Ft.11/8/2023Pine Bark Dr1443$744,6152,955 Sq.Ft.6/24/2022Pine Bluff Ct842$494,2502,571 Sq.Ft.2/2/2023Pine Bnd3532$264,9121,375 Sq.Ft.4/14/2025Pinecliffe Ct333$564,0002,473 Sq.Ft.12/2/2016Pinecliffe Dr1943$568,1112,516 Sq.Ft.5/10/2024Pinecroft Ln1632$390,2501,871 Sq.Ft.1/9/2025Pinedale Ln1953$647,2353,029 Sq.Ft.5/6/2025Pine Forest Ln1943$699,0562,530 Sq.Ft.12/15/2020Pine Grove Cir454$726,2503,405 Sq.Ft.5/29/20254104 3rd StChesapeake, VA 23324
Estimated Value $396,000
Living Area 2,207 SqFt
Beds 5
Baths 3
Year Built 2010
Property Type Single Family
Ownership Type Individual
APN 1590000003330
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
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
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
1203 Cedar Craft LnChesapeake, VA 23323
Estimated Value $416,000
Living Area 2,179 SqFt
Beds 4
Baths 2.5
Year Built 2000
Property Type Single Family
Ownership Type Related
APN 0343023000920
Neighborhood Deep Creek
School District Chesapeake City Public Schools
904 Robert Welch CtChesapeake, VA 23320
Estimated Value $574,000
Living Area 3,351 SqFt
Beds 5
Baths 3
Year Built 2006
Property Type Single Family
Ownership Type Multiple
APN 0361016000230
Neighborhood Rivercrest
School District Chesapeake City Public Schools
847 Creekside CresChesapeake, VA 23320
Estimated Value $264,000
Living Area 1,348 SqFt
Beds 2
Baths 2.5
Year Built 1990
Property Type Townhouse
Ownership Type Corporate
APN 0367006000310
Neighborhood Rivercrest
School District Chesapeake City Public Schools
963 Railroad AveChesapeake, VA 23324
Estimated Value $336,000
Living Area 1,911 SqFt
Beds 3
Baths 2.5
Year Built 2016
Property Type Single Family
Ownership Type Related
APN 1600000000750
Neighborhood South Norfolk
School District Chesapeake City Public Schools
1648 Shipyard RdChesapeake, VA 23323
Estimated Value $1,031,000
Living Area 4,796 SqFt
Beds 5
Baths 4.5
Year Built 2013
Property Type Single Family
Ownership Type Multiple
APN 0350000000430
Neighborhood Deep Creek
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
1129 Cherrytree LnChesapeake, VA 23320
Estimated Value $425,000
Living Area 1,606 SqFt
Beds 4
Baths 2
Year Built 1992
Property Type Single Family
Ownership Type Related
APN 0363007001370
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1727 Faulk StChesapeake, VA 23323
Estimated Value $281,000
Living Area 1,424 SqFt
Beds 3
Baths 2.5
Year Built 2004
Property Type Single Family
Ownership Type Individual
APN 0261002000150
Neighborhood Deep Creek
School District Chesapeake City Public Schools
4102 Dyanax StChesapeake, VA 23324
Estimated Value $319,000
Living Area 388 SqFt
Beds 3
Baths 2
Year Built 2021
Property Type Single Family
Ownership Type Individual
APN 1590000001390
Neighborhood South Norfolk
School District Chesapeake City Public Schools
1300 Lucas AveChesapeake, VA 23324
Estimated Value $218,000
Living Area 1,000 SqFt
Beds 3
Baths 1.5
Year Built 1987
Property Type Single Family
Ownership Type Individual
APN 1590000002490
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
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