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
Swindell St233$279,0001,316 Sq.Ft.6/5/2008Swinson Lndg532$384,7501,633 Sq.Ft.6/21/2023Sword Dr1532$318,5001,527 Sq.Ft.9/5/2024Sybilla St2943$584,5772,880 Sq.Ft.2/15/2024Sycamore Ln1542$492,6002,029 Sq.Ft.4/23/2025Sydenham Blvd5343$606,6382,552 Sq.Ft.2/3/2023Sydney Ct543$490,6002,117 Sq.Ft.9/16/2023Sykes Dr2253$664,6323,032 Sq.Ft.9/9/2022Sylvia Ct555$1,432,8005,604 Sq.Ft.5/7/2025Tafton Way754$749,4293,720 Sq.Ft.12/20/2016Taft Rd12543$831,4953,032 Sq.Ft.4/25/2025Tallahassee Dr2042$555,4502,464 Sq.Ft.7/26/2023Tall Oak Ct642$348,6671,585 Sq.Ft.2/12/2016Tall Pine Dr2253$658,4212,770 Sq.Ft.10/1/2024Tallwood Cir2933$361,0691,810 Sq.Ft.3/31/2025Tamer Ave531$304,4001,143 Sq.Ft.10/10/2024Tampa Dr443$427,2502,507 Sq.Ft.12/22/2003Tanager Xing1742$528,6882,239 Sq.Ft.5/6/2024Tanglewood Trl3532$439,0291,891 Sq.Ft.3/31/2023Tannahill Ct333$603,3332,713 Sq.Ft.5/19/2014Tanners Green Ct433$373,0001,979 Sq.Ft.5/2/2022Tapestry Park Dr1N/AN/AN/A277,846 Sq.Ft.6/1/2009Tapgallant Quay1054$689,5003,751 Sq.Ft.9/25/2024Tapscott Ave1842$350,2941,930 Sq.Ft.11/21/2024Tara Cir943$574,3752,713 Sq.Ft.7/14/2020Taralynn Ln633$377,0001,894 Sq.Ft.7/9/2024Tarkington Ct1443$637,2142,618 Sq.Ft.6/29/2022Tarneywood Ct532$454,2001,869 Sq.Ft.7/28/2021Tarneywood Dr1443$461,7862,039 Sq.Ft.6/25/2024Tartan Arch1144$648,0003,524 Sq.Ft.5/26/2023Taryn Ct653$636,6002,731 Sq.Ft.6/27/2024Tasley Cir643$611,8002,646 Sq.Ft.5/15/2018Tasman Ct932$322,3331,398 Sq.Ft.5/26/2021Tatemstown Rd3232$293,6901,978 Sq.Ft.5/20/2025Tattenhall Ln653$598,0003,083 Sq.Ft.3/11/2024Tattinger Trl1443$564,0002,788 Sq.Ft.9/11/2024Taughtline Loop3743$368,4842,157 Sq.Ft.2/11/2025Tawnyberry Ln2433$329,2731,746 Sq.Ft.6/22/2022Taxus St1632$333,6671,774 Sq.Ft.8/15/2023Taylor1N/AN/AN/AN/A10/27/2023Taylor Acres Ct543$490,0002,532 Sq.Ft.4/27/2023Taylor Ct832$406,4002,110 Sq.Ft.1/27/2025Taylor Point Dr2554$705,8333,807 Sq.Ft.4/8/2024Taylor Rd13432$353,7845,794 Sq.Ft.3/12/2025Taylorwood Blvd1532$370,5001,628 Sq.Ft.4/15/2025Taylorwood Ct632$352,3331,541 Sq.Ft.3/11/2022Teakwood Ct454$756,7503,685 Sq.Ft.7/15/2024Teal Ct9N/AN/AN/AN/AN/ATealwood Ln1433$359,2141,829 Sq.Ft.4/14/2025Tea Rose Ln2N/AN/A$607,000N/A10/12/2017Technology Dr10N/AN/AN/A6,728 Sq.Ft.5/11/2018Tejo Ln1N/AN/AN/A12,872 Sq.Ft.7/11/2017Tekoa Rd2931$254,9661,034 Sq.Ft.1/31/2025Telfon Cir853$746,3753,455 Sq.Ft.1/29/2025Telfyan Dr653$577,0003,036 Sq.Ft.5/14/2021Tennessee Dr3532$320,4241,438 Sq.Ft.4/29/2025Tennis Dr732$427,2861,772 Sq.Ft.6/3/2025Tennyson St1032$348,4291,670 Sq.Ft.8/21/2024Teresa Dr1832$488,1112,134 Sq.Ft.6/30/2021Tern Ct343$554,6672,629 Sq.Ft.2/28/2025Terra Vista Dr1N/AN/AN/AN/A1/2/2025Terry Dr4632$338,5711,756 Sq.Ft.5/5/2025Terwillinger Rd2443$486,9472,119 Sq.Ft.5/30/2024Tether Wood Ct753$606,0003,127 Sq.Ft.8/15/2019Teton Ct4743$651,3002,786 Sq.Ft.4/28/2025Texas Ave1N/AN/AN/AN/AN/ATexas St1432$338,1431,781 Sq.Ft.12/13/2024Thaddeus Ct653$696,6003,383 Sq.Ft.9/19/2023Thames Cir1232$264,5831,218 Sq.Ft.8/8/2024Thatcher Way3343$450,8752,154 Sq.Ft.4/12/2025Theodora Ct553$777,7503,720 Sq.Ft.6/13/2014Thistle Ct443$503,0001,875 Sq.Ft.2/5/2018Thistlewood Ct633$486,5002,362 Sq.Ft.11/21/2024Thistlewood Ln3432$438,9031,996 Sq.Ft.4/17/2025Thistley Ln4354$1,105,0004,313 Sq.Ft.2/24/2025Thomas Ln1432$249,6431,371 Sq.Ft.2/7/2025Thomason Trl2233$379,6001,912 Sq.Ft.7/27/2023Thomas St1342$344,2311,660 Sq.Ft.4/25/2025Thorngate Ct354$790,3333,757 Sq.Ft.10/11/2024Thornloe Ln532$413,7501,785 Sq.Ft.7/13/2022Thorn Rose Ct632$469,5002,015 Sq.Ft.8/22/2019Thornton Cir933$493,0002,309 Sq.Ft.2/29/2024Thornwood Ln1033$490,1002,622 Sq.Ft.4/29/2025Thoroughgood Way2422$244,3331,243 Sq.Ft.9/3/2024Thrasher Lndg1953$737,8243,236 Sq.Ft.8/7/2024Thrasher Rd2732$390,2311,814 Sq.Ft.7/26/2024Three Oaks Dr1242$459,1671,965 Sq.Ft.9/26/2023Threshold Ct1N/AN/AN/AN/A2/28/2023Thrive Pl1N/AN/AN/A102,750 Sq.Ft.9/15/2015Thrower St131$244,0001,176 Sq.Ft.7/23/2021Thrush Ct432$418,7501,655 Sq.Ft.7/8/2021Thurman St1N/AN/AN/AN/AN/AThyme Trl2543$492,0832,477 Sq.Ft.7/23/2024Tidal Island Way743$640,3333,263 Sq.Ft.12/15/2023Tidewater Chemical Rd1N/AN/AN/A5,625 Sq.Ft.N/ATiffany Green Ct2033$377,4741,989 Sq.Ft.3/26/2024Tiger Dr2N/AN/AN/A149,939 Sq.Ft.N/ATigertail Dr423$249,0001,262 Sq.Ft.10/12/2022Tiki Way1553$884,5713,754 Sq.Ft.10/25/2024Tilden Ave16N/AN/AN/A5,409 Sq.Ft.3/27/2025858 Creekside CresChesapeake, VA 23320
Estimated Value $257,000
Living Area 1,348 SqFt
Beds 2
Baths 2.5
Year Built 1990
Property Type Townhouse
Ownership Type Individual
APN 0367006000220
Neighborhood Rivercrest
School District Chesapeake City Public Schools
807 Shenandoah River RdChesapeake, VA 23320
Estimated Value $279,000
Living Area 1,350 SqFt
Beds 2
Baths 2
Year Built 1990
Property Type Condominium
Ownership Type Individual
APN 0367003000790
Neighborhood Rivercrest
School District Chesapeake City Public Schools
305 Creek LnChesapeake, VA 23320
Estimated Value $536,000
Living Area 2,952 SqFt
Beds 4
Baths 2.5
Year Built 1989
Property Type Single Family
Ownership Type Related
APN 0369004000230
Neighborhood Rivercrest
School District Chesapeake City Public Schools
568 Marc Smiley RdChesapeake, VA 23324
Estimated Value $318,000
Living Area 1,720 SqFt
Beds 3
Baths 2.5
Year Built 2017
Property Type Condominium
Ownership Type Individual
APN 1580001001270
Neighborhood South Norfolk
School District Chesapeake City Public Schools
103 Ford StChesapeake, VA 23323
Estimated Value $348,000
Living Area 1,972 SqFt
Beds 4
Baths 3
Year Built 2018
Property Type Single Family
Ownership Type Multiple
APN 0261002000780
Neighborhood Deep Creek
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
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
510 Sloane StChesapeake, VA 23324
Estimated Value $307,000
Living Area 1,464 SqFt
Beds 2
Baths 2.5
Year Built 2016
Property Type Condominium
Ownership Type Individual
APN 1580001001430
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
1824 Warfield StChesapeake, VA 23324
Estimated Value $282,000
Living Area 1,476 SqFt
Beds 3
Baths 2.5
Year Built 2006
Property Type Single Family
Ownership Type Related
APN 1600000002671
Neighborhood South Norfolk
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
1505 Waitsel Dr #206Chesapeake, VA 23320
Estimated Value $284,000
Living Area 1,327 SqFt
Beds 2
Baths 2
Year Built 2023
Property Type Condominium
Ownership Type Individual
APN 0273016000410
Neighborhood Rivercrest
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
1235 Woods WayChesapeake, VA 23323
Estimated Value $366,000
Living Area 1,875 SqFt
Beds 3
Baths 2.5
Year Built 1999
Property Type Single Family
Ownership Type Related
APN 0343023001190
Neighborhood Deep Creek
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
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