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
Princess Anne Cres5042$455,3602,394 Sq.Ft.5/5/2025Princess Anne Ct442$428,0001,937 Sq.Ft.7/15/2021Princeton Ave1632$292,2671,262 Sq.Ft.1/10/2025Principal Ct3N/AN/AN/A33,651 Sq.Ft.11/25/2014Principal Ln3N/AN/AN/A16,298 Sq.Ft.9/27/2016Prindle Ct1N/AN/AN/A121,200 Sq.Ft.N/APringle Dr2131$275,4501,200 Sq.Ft.2/8/2024Printers Pl943$428,2502,735 Sq.Ft.12/9/2020Priority Ln37N/AN/A$240,00045,449 Sq.Ft.10/2/2020Priscilla Ln11042$476,1382,002 Sq.Ft.3/20/2025Professional Pl88N/A20N/A5,518 Sq.Ft.4/8/2025Profit Way3N/AN/AN/A27,843 Sq.Ft.11/1/2021Progress Ct532$418,6671,343 Sq.Ft.4/27/2018Progress Dr2342$438,4172,054 Sq.Ft.1/26/2023Progressive Dr2N/AN/AN/A31,390 Sq.Ft.12/17/2020Prospect Ct642$549,3332,474 Sq.Ft.2/11/2021Prospect Dr4342$546,1282,337 Sq.Ft.8/21/2024Prospect Trce542$548,6002,299 Sq.Ft.6/25/2024Prosperity Way33N/AN/AN/A1,530 Sq.Ft.3/14/2025Providence Rd13332$357,9366,219 Sq.Ft.11/6/2024Prudden Trce1443$467,0002,003 Sq.Ft.8/9/2024Prudence Pl1333$400,0911,811 Sq.Ft.4/17/2023Pryor Ct1342$361,0771,670 Sq.Ft.6/17/2022Pucknall Dr1033$337,1111,870 Sq.Ft.12/23/2024Pughsville Rd1643$360,8462,161 Sq.Ft.5/24/2024Pummis Ln1443$663,2222,718 Sq.Ft.7/31/2024Quail Ave5531$240,4051,113 Sq.Ft.1/24/2025Quail Creek Holw1522$291,2671,285 Sq.Ft.10/31/2024Quail Meadow Dr1842$410,7501,806 Sq.Ft.4/10/2025Quail Ridge Ct1532$448,4672,282 Sq.Ft.9/19/2023Quailshire Arch643$548,8332,922 Sq.Ft.7/31/2017Quailshire Ct1953$587,2002,961 Sq.Ft.6/12/2024Quailshire Ln2153$519,3682,792 Sq.Ft.2/20/2024Quaker Pl1043$415,3002,510 Sq.Ft.1/4/2024Quarter Path Trl2832$352,9631,457 Sq.Ft.3/31/2025Quartz Trl1343$722,1673,411 Sq.Ft.5/30/2025Queen City Rd3N/AN/AN/A8,125 Sq.Ft.10/25/2021Queensbury Dr1053$690,0002,906 Sq.Ft.2/28/2024Queens Gate1943$399,5292,176 Sq.Ft.8/14/2023Queens Grv343$663,3333,649 Sq.Ft.4/2/2024Queens Gtwy1N/AN/AN/AN/AN/AQueen St2442$274,3641,743 Sq.Ft.8/8/2024Queenswood Ter3242$531,3132,188 Sq.Ft.4/8/2025Quinby Ct832$327,0001,285 Sq.Ft.5/23/2024Quince Pl3N/AN/AN/A4,404 Sq.Ft.N/AQuivers Keep2853$587,5003,020 Sq.Ft.8/31/2023Rabbit Run1243$501,3332,354 Sq.Ft.12/6/2021Radcliffe Ln10432$278,9301,548 Sq.Ft.10/29/2024Radford Cir10522$210,9621,218 Sq.Ft.4/27/2025Raeside Ave1643$446,1002,187 Sq.Ft.11/13/2024Raewick Ct543$538,6002,787 Sq.Ft.5/30/2024Ragged Island Rd811$162,000420 Sq.Ft.3/29/2024Railroad Ave7732$277,9151,536 Sq.Ft.5/22/2025Railway Ct1133$298,9091,478 Sq.Ft.3/27/2025Rainbow Run2642$484,3852,213 Sq.Ft.8/16/2024Raintree Ct2422$242,0001,230 Sq.Ft.5/5/2025Raintree Rd3N/AN/AN/A20,556 Sq.Ft.2/21/2023Raleigh Ct543$628,6003,793 Sq.Ft.5/12/2023Raleigh Rd3342$448,2502,260 Sq.Ft.10/31/2024Ramblewood Ct354$781,6673,514 Sq.Ft.10/28/2015Ramsgate Ln1442$489,7691,955 Sq.Ft.2/15/2024Randy Ct243$487,5002,420 Sq.Ft.11/15/2018Ranger Rd22N/AN/A$802,000N/A5/13/2010Ransom Ct243$550,5003,088 Sq.Ft.N/ARapidan River Ct6522$226,4921,052 Sq.Ft.6/3/2025Rapid Run3N/AN/A$265,667N/A6/25/2024Rathwell Ct1942$469,1581,732 Sq.Ft.4/11/2025Raton Ct1243$480,6362,096 Sq.Ft.3/28/2025Ravenna Arch463$775,6673,631 Sq.Ft.6/29/2018Ravenna Crse3153$779,0423,433 Sq.Ft.7/24/2023Ravenstone Ct342$446,5001,659 Sq.Ft.10/9/2018Ravenstone Dr3642$489,8862,073 Sq.Ft.7/18/2024Ravenwoods Dr2143$890,3813,638 Sq.Ft.2/13/2025Ray Ave2543$397,6672,143 Sq.Ft.2/27/2024Raytee Dr1553$573,1543,468 Sq.Ft.9/6/2024Reardon Ct453$607,0003,086 Sq.Ft.11/10/2016Rebecca Dr1643$580,8572,324 Sq.Ft.9/27/2024Rebel Rd3832$444,9731,915 Sq.Ft.4/25/2025Red Bay Cir442$480,2501,954 Sq.Ft.9/30/2020Red Bay Ln5942$493,9651,946 Sq.Ft.12/2/2024Redbrick Ct442$381,5002,056 Sq.Ft.2/28/2013Redbrick Dr3242$392,6452,144 Sq.Ft.9/1/2022Red Cedar Ct322N/A50,238 Sq.Ft.9/12/2018Redcoat Chase653$565,6003,433 Sq.Ft.3/12/2024Redding Ct453$684,7503,399 Sq.Ft.5/5/2023Redfern Ln1342$395,7502,128 Sq.Ft.7/1/2024Red Head Ct9N/AN/AN/AN/AN/ARedleafe Cir6453$790,9073,953 Sq.Ft.10/10/2024Red Maple Rd1731$262,7501,192 Sq.Ft.6/9/2021Redmere Ct632$429,2001,881 Sq.Ft.6/30/2022Red Oak Trl1632$393,9381,764 Sq.Ft.7/5/2022Red Rider Ln1243$479,0912,138 Sq.Ft.7/27/2024Redstart Ave3531$266,5431,203 Sq.Ft.4/24/2025Redwing Arc2933$388,8971,765 Sq.Ft.1/29/2025Redwood Dr742$436,2862,160 Sq.Ft.2/6/2006Reef Knot Ct1143$603,3333,110 Sq.Ft.4/27/2022Reefwood Rd3543$598,6672,500 Sq.Ft.5/23/2025Refuge Xing754$700,6003,554 Sq.Ft.11/4/2019Regal Ct1143$541,7002,465 Sq.Ft.9/29/2021Regency St2153$672,8953,287 Sq.Ft.4/28/20254101 Dyanax StChesapeake, VA 23324
Estimated Value $182,000
Living Area 896 SqFt
Beds 2
Baths 1
Year Built 1940
Property Type Single Family
Ownership Type Individual
APN 1590000001430
Neighborhood South Norfolk
School District Chesapeake City Public Schools
4201 1st StChesapeake, VA 23324
Estimated Value $213,000
Living Area 889 SqFt
Beds 3
Baths 1
Year Built 1940
Property Type Single Family
Ownership Type Corporate
APN 1590000002990
Neighborhood South Norfolk
School District Chesapeake City Public Schools
1202 Basswood CtChesapeake, VA 23320
Estimated Value $266,000
Living Area 1,260 SqFt
Beds 3
Baths 2.5
Year Built 1987
Property Type Townhouse
Ownership Type Related
APN 0366008000450
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1512 Shell RdChesapeake, VA 23323
Estimated Value $276,000
Living Area 1,344 SqFt
Beds 3
Baths 2.5
Year Built 1960
Property Type Single Family
Ownership Type Corporate
APN 0261001000010
Neighborhood Deep Creek
School District Chesapeake City Public Schools
1712 Foremast LoopChesapeake, VA 23323
Estimated Value $419,000
Living Area 2,120 SqFt
Beds 3
Baths 2.5
Year Built 2020
Property Type Condominium
Ownership Type Individual
APN 0354003004140
Neighborhood Deep Creek
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
117 Gibson DrChesapeake, VA 23320
Estimated Value $452,000
Living Area 2,142 SqFt
Beds 4
Baths 2
Year Built 1974
Property Type Single Family
Ownership Type Related
APN 0361005000200
Neighborhood Rivercrest
School District Chesapeake City Public Schools
4309 Pickney LnChesapeake, VA 23324
Estimated Value $324,000
Living Area 1,720 SqFt
Beds 3
Baths 2.5
Year Built 2018
Property Type Condominium
Ownership Type Multiple
APN 1580001000780
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
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
309 Paperbark TrlChesapeake, VA 23323
Estimated Value $369,000
Living Area 1,610 SqFt
Beds 3
Baths 2
Year Built 1998
Property Type Single Family
Ownership Type Multiple
APN 0343023000480
Neighborhood Deep Creek
School District Chesapeake City Public Schools
1024 Calloway AveChesapeake, VA 23324
Estimated Value $219,000
Living Area 912 SqFt
Beds 3
Baths 1.5
Year Built 1972
Property Type Single Family
Ownership Type Individual
APN 1520000001640
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
1923 Linster StChesapeake, VA 23324
Estimated Value $323,000
Living Area 1,934 SqFt
Beds 4
Baths 2
Year Built 2016
Property Type Single Family
Ownership Type Multiple
APN 1600000000890
Neighborhood South Norfolk
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
1207 Basswood CtChesapeake, VA 23320
Estimated Value $273,000
Living Area 1,264 SqFt
Beds 3
Baths 2.5
Year Built 1987
Property Type Townhouse
Ownership Type Individual
APN 0366008000410
Neighborhood Rivercrest
School District Chesapeake City Public Schools