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
Tiller Ln1532$295,2311,406 Sq.Ft.2/27/2025Tillman Arch1253$675,8003,074 Sq.Ft.2/14/2025Timberlake Ct1732$360,3751,558 Sq.Ft.4/6/2023Timberline Ct453$776,0003,703 Sq.Ft.3/13/2015Timber Ln1242$249,6671,624 Sq.Ft.N/ATimber Neck Close253$727,5003,321 Sq.Ft.12/17/2021Timber Neck Mall1753$747,6673,757 Sq.Ft.6/27/2024Timber Quay543$615,0003,120 Sq.Ft.10/6/2022Timber Ridge Ct343$567,6672,596 Sq.Ft.4/28/2022Timber Ridge Rd1343$552,0002,547 Sq.Ft.5/9/2024Timmons Ct1253$637,9093,062 Sq.Ft.3/15/2024Tintern Ct5N/AN/AN/A9,523 Sq.Ft.6/13/2018Tintern St8N/AN/A$155,00038,507 Sq.Ft.5/1/2024Tisbury Dr942$446,0001,889 Sq.Ft.8/18/2022Tiswood Ct753$593,2863,164 Sq.Ft.10/19/2010Titchfield Dr5523$282,0561,350 Sq.Ft.5/22/2025Tiverton Pl642$421,5001,783 Sq.Ft.2/10/2023Tluchak Ln13N/AN/AN/A11,107 Sq.Ft.8/8/2024Todd Ln153N/A3,006 Sq.Ft.12/13/2017Toll Plaza Rd643$733,2003,251 Sq.Ft.8/11/2016Topsail Lndg1854$682,4713,874 Sq.Ft.8/25/2022Torre Pine Ct554$853,2003,847 Sq.Ft.7/17/2024Touchstone Ter1N/AN/AN/A170,092 Sq.Ft.12/10/2013Tournament Dr6132$320,2761,612 Sq.Ft.5/29/2025Towanda Ct832$285,0001,229 Sq.Ft.2/3/2025Towanda Rd2932$309,0371,275 Sq.Ft.9/20/2024Towering Oak Ct542$342,8001,567 Sq.Ft.10/3/2019Towhee Ln743$396,5711,740 Sq.Ft.1/28/2020Towne Point Rd2N/AN/AN/AN/A12/9/2019Townhouse Ln331$238,50029,831 Sq.Ft.12/11/2018Traciene Dr155$1,308,0005,106 Sq.Ft.9/1/2015Tracker Ln1432$259,6921,573 Sq.Ft.2/7/2022Track Xing4233$300,5951,576 Sq.Ft.11/5/2024Trademark Crst254$736,0003,452 Sq.Ft.6/30/2009Trade St8N/AN/AN/A57,809 Sq.Ft.11/7/2022Trafalgar Ct353$605,0002,609 Sq.Ft.3/29/2024Trafton Pl3033$390,4291,892 Sq.Ft.1/23/2025Trail Bend Dr1533$355,6431,702 Sq.Ft.12/30/2024Trajan Reach454$790,7503,589 Sq.Ft.4/21/2021Tranquility Trce6143$695,5862,705 Sq.Ft.3/3/2025Transylvania Ave3042$305,4072,230 Sq.Ft.4/14/2025Trappers Run2032$259,3001,472 Sq.Ft.4/30/2025Trapshoot Ct832$266,2501,595 Sq.Ft.12/6/2024Travelers Way543$559,8002,762 Sq.Ft.1/27/2011Travertine Way2053$715,8673,108 Sq.Ft.4/30/2024Travis Ct442$503,7501,822 Sq.Ft.5/1/2025Treasure Way653$673,6003,200 Sq.Ft.8/25/2015Tree Duck Ct9N/AN/AN/AN/A5/25/2022Tree Fern Dr1743$644,2503,092 Sq.Ft.9/29/2023Treeland Ter742$524,7142,112 Sq.Ft.4/13/2019Treemont Ct1632$377,1251,699 Sq.Ft.4/10/2025Treetop Ln1143$490,5562,614 Sq.Ft.8/1/2023Trellis Trl1433$341,8571,858 Sq.Ft.11/9/2022Trent Ave3131$315,1671,345 Sq.Ft.4/23/2025Trescott Way354$604,5002,703 Sq.Ft.8/15/2024Trestle Way2533$319,0481,443 Sq.Ft.5/14/2025Trevor Ct343$620,5002,522 Sq.Ft.9/4/2019Trey Ln454$939,0003,940 Sq.Ft.9/30/2024Trilby Ct942$437,8751,764 Sq.Ft.7/24/2024Trinkle St27944$431,9572,544 Sq.Ft.3/19/2025Tristan Rd1653$759,2143,234 Sq.Ft.11/28/2023Triton Trce1242$460,0001,907 Sq.Ft.12/13/2022Trolley Xing2033$303,3001,547 Sq.Ft.5/12/2025Trotters Ln1953$740,6323,478 Sq.Ft.11/24/2024Troy Ln2732$329,4231,229 Sq.Ft.2/19/2025Truitt Rd3832$386,0611,982 Sq.Ft.8/2/2024Trumpet Ct1243$743,2003,202 Sq.Ft.7/15/2020Trumpet Rd2942$386,6901,798 Sq.Ft.11/8/2024Truxton St14N/A2N/A3,918 Sq.Ft.1/20/2023Tuckaway Reach1632$303,9381,451 Sq.Ft.4/29/2025Tuck St23732$459,8311,276 Sq.Ft.4/25/2025Tudor Pl1532$395,0672,155 Sq.Ft.10/21/2024Tufton Ct343$643,5002,545 Sq.Ft.1/25/2023Tulip Dr742$489,4292,138 Sq.Ft.10/7/2020Tundrah Ct843$736,5713,205 Sq.Ft.7/16/2021Tunnel Ct1233$300,0831,540 Sq.Ft.3/25/2024Tupelo Xing2343$615,6843,247 Sq.Ft.9/8/2023Turin Ct643$536,0002,558 Sq.Ft.1/25/2017Turnberry Ct1054$925,4294,221 Sq.Ft.8/2/2024Turnbuckle Ct1343$567,6672,738 Sq.Ft.7/18/2024Turning Leaf Ln833$524,7502,572 Sq.Ft.11/14/2024Turtle Dove Ct1543$383,4291,959 Sq.Ft.10/21/2024Turtle Rock Trce4032$353,3891,441 Sq.Ft.5/21/2025Tuskegee Ave3643$394,6252,140 Sq.Ft.10/16/2023Tuttle St141$326,0001,940 Sq.Ft.8/26/2003Twelve Oaks Ct1443$610,3083,003 Sq.Ft.9/6/2022Twilight Arch1053$629,5003,035 Sq.Ft.10/17/2024Twin Cedar Trl3542$481,6862,068 Sq.Ft.8/15/2023Twine Ln1423$313,9231,511 Sq.Ft.11/12/2024Twin Oaks Ct1042$354,3001,663 Sq.Ft.7/20/2022Twin Peak Ct943$606,5002,959 Sq.Ft.10/10/2024Two Gates Cir1744$1,049,2353,917 Sq.Ft.11/10/2023Tybee Loop3143$527,8182,607 Sq.Ft.6/21/2022Tybourne Ct1242$473,8181,713 Sq.Ft.11/17/2017Tyler Way3353$636,3332,887 Sq.Ft.8/29/2024Tyre Neck Rd10532$416,0492,184 Sq.Ft.1/3/2025Uffington Ct443$512,7502,566 Sq.Ft.10/30/2020Undershot Ct553$584,6673,095 Sq.Ft.3/18/2020Unicorn Trl1044$762,2003,636 Sq.Ft.6/12/2024Union Forge Ln1943$534,0002,315 Sq.Ft.5/9/2025809 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
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
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
609 Tuskegee AveChesapeake, VA 23320
Estimated Value $384,000
Living Area 2,058 SqFt
Beds 3
Baths 2.5
Year Built 2002
Property Type Single Family
Ownership Type Individual
APN 0351004002130
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
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
1709 Foremast LoopChesapeake, VA 23323
Estimated Value $379,000
Living Area 1,720 SqFt
Beds 3
Baths 2.5
Year Built 2020
Property Type Condominium
Ownership Type Related
APN 0354003002410
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
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
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
4139 1st StChesapeake, VA 23324
Estimated Value $299,000
Living Area 1,008 SqFt
Beds 2
Baths 1
Year Built 2005
Property Type Single Family
Ownership Type Related
APN 1590000002910
Neighborhood South Norfolk
School District Chesapeake City Public Schools
1040 Campostella RdChesapeake, VA 23320
Estimated Value $226,000
Living Area 917 SqFt
Beds 3
Baths 1
Year Built 1955
Property Type Single Family
Ownership Type Individual
APN 0362001001450
Neighborhood Rivercrest
School District Chesapeake City Public Schools
209 Outlaw StChesapeake, VA 23320
Estimated Value $399,000
Living Area 2,236 SqFt
Beds 4
Baths 2.5
Year Built 2003
Property Type Single Family
Ownership Type Multiple
APN 0351004001500
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1620 Burson DrChesapeake, VA 23323
Estimated Value $772,000
Living Area 3,381 SqFt
Beds 3
Baths 3
Year Built 2015
Property Type Single Family
Ownership Type Related
APN 0344002003961
Neighborhood Deep Creek
School District Chesapeake City Public Schools
4149 Everett StChesapeake, VA 23324
Estimated Value $306,000
Living Area 1,590 SqFt
Beds 3
Baths 2.5
Year Built 2005
Property Type Single Family
Ownership Type Multiple
APN 1600000001861
Neighborhood South Norfolk
School District Chesapeake City Public Schools
1210 Freeman AveChesapeake, VA 23324
Estimated Value $231,000
Living Area 968 SqFt
Beds 2
Baths 1
Year Built 1940
Property Type Single Family
Ownership Type Corporate
APN 1590000001790
Neighborhood South Norfolk
School District Chesapeake City Public Schools