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
Buxton Dr1332$423,0771,749 Sq.Ft.4/24/2025Byrd Ave1431$291,2861,649 Sq.Ft.9/26/2024Byrd Ct1733$279,3751,560 Sq.Ft.10/13/2023Byron St2832$298,9094,176 Sq.Ft.12/2/2024Bywood Ave1431$325,2861,625 Sq.Ft.5/19/2023Caboose Ct933$301,8891,551 Sq.Ft.6/27/2024Caddie St16N/AN/A$466,500N/A5/2/2025Caden Ln1023$284,1002,275 Sq.Ft.10/6/2023Cahoon Pkwy5N/AN/A$1,129,00028,644 Sq.Ft.1/24/2022Cairns Rd3353$740,1602,959 Sq.Ft.7/19/2024Calabria Dr453$709,3333,386 Sq.Ft.8/26/2024Caleb Dr1842$496,4442,194 Sq.Ft.8/12/2024Calico Ct453$758,7503,624 Sq.Ft.5/20/2024Calisha Ct743$449,6672,596 Sq.Ft.12/18/2023Calista Dr2243$624,6822,562 Sq.Ft.11/21/2023Callery Ct543$448,4002,082 Sq.Ft.3/5/2024Callison Dr443$363,2502,066 Sq.Ft.6/8/2023Calloway Ave2842$332,0401,721 Sq.Ft.12/11/2024Calm Wood Way1143$448,0912,084 Sq.Ft.12/9/2019Calonia Arch1342$489,3642,352 Sq.Ft.5/15/2023Calumet St1153$753,8003,587 Sq.Ft.4/12/2024Calvert Ct633$410,6672,225 Sq.Ft.3/21/2024Calverton Ct743$491,6672,456 Sq.Ft.5/8/2023Calverton Way4443$492,0952,489 Sq.Ft.3/13/2025Camberley Way4022$199,3001,051 Sq.Ft.8/16/2024Camberly Ct543$541,2502,607 Sq.Ft.12/5/2022Cambridge Ct443$579,2502,926 Sq.Ft.8/8/2024Cambridge Way1943$556,5792,633 Sq.Ft.11/20/2024Camden Pl343$474,6672,028 Sq.Ft.5/28/2024Camellia Ct342$472,6671,886 Sq.Ft.3/25/2025Camelot Blvd11032$333,9181,938 Sq.Ft.3/6/2025Camelot Ct932$337,7501,717 Sq.Ft.6/15/2023Cameo Ter2032$423,0001,969 Sq.Ft.3/18/2024Campbell Rd2742$613,6472,096 Sq.Ft.10/16/2023Campostella Rd17632$286,6465,885 Sq.Ft.5/20/2025Camp St943$584,0002,613 Sq.Ft.2/21/2023Canadian Dr1N/AN/AN/AN/AN/ACanal Dr7532$326,5114,016 Sq.Ft.10/9/2024Canary Ct543$585,5002,900 Sq.Ft.4/17/2025Candlelight Dr12633$254,2101,374 Sq.Ft.5/14/2025Candlewood Cir5332$300,0751,497 Sq.Ft.12/31/2024Candlewood Ct532$324,0001,720 Sq.Ft.1/3/2025Candy Ln1532$386,1331,738 Sq.Ft.7/20/2022Canning Pl7833$439,3191,771 Sq.Ft.5/29/2025Cannongate Ter2133$432,9501,740 Sq.Ft.5/23/2025Cannon Point Dr5032$403,2131,730 Sq.Ft.1/9/2025Canoe St3443$597,4292,885 Sq.Ft.11/10/2024Canterbury Rd632$381,8001,565 Sq.Ft.5/24/2022Canton Ave1632$311,5631,321 Sq.Ft.2/2/2024Cantor St2342$511,9572,299 Sq.Ft.5/31/2023Canvasback Ct8N/AN/AN/AN/AN/ACape May Loop2443$531,5562,568 Sq.Ft.5/1/2023Capital Ave942$340,5561,847 Sq.Ft.5/25/2022Capri Cir3232$354,5311,481 Sq.Ft.3/6/2024Capstan Way533$389,6001,904 Sq.Ft.8/21/2023Captain Carter Cir2043$496,1582,273 Sq.Ft.2/27/2025Captain Cooke Way2243$560,7732,465 Sq.Ft.5/8/2024Captains Ct2222$256,0911,088 Sq.Ft.4/28/2025Captiva Ln5343$503,7552,523 Sq.Ft.6/6/2025Caravelle Ct842$461,6251,731 Sq.Ft.12/9/2020Caravelle Dr3332$465,8711,802 Sq.Ft.8/1/2024Carawan Ln4032$418,2781,822 Sq.Ft.1/3/2025Cardiff Ln2422$273,3751,523 Sq.Ft.1/4/2024Cardigan St2332$298,0911,506 Sq.Ft.5/9/2025Cardinal St1533$274,8001,786 Sq.Ft.N/ACardover Ave3532$312,6061,546 Sq.Ft.5/7/2025Carey Ct753$691,0003,225 Sq.Ft.2/25/2005Carissa Way733$392,6671,683 Sq.Ft.3/10/2025Carley Ct7N/AN/A$1,227,000N/A7/27/2022Carlisle Rd832$518,6672,221 Sq.Ft.11/17/2023Carmichael Way14N/AN/AN/A20,753 Sq.Ft.11/12/2024Caroga Ct442$496,2501,882 Sq.Ft.7/20/2017Carol Dr1421$694,5381,080 Sq.Ft.6/5/2025Carolina Rd8643$710,6762,660 Sq.Ft.3/4/2025Carolyn Dr2132$312,9521,445 Sq.Ft.7/19/2023Carr Ave3N/AN/A$371,667N/A12/29/2017Carrera Rdg2343$718,6823,025 Sq.Ft.6/11/2024Carriage Ct1043$552,1252,295 Sq.Ft.6/10/2022Carrick Ct1053$618,1113,205 Sq.Ft.6/28/2024Carrington Ave221$323,0001,262 Sq.Ft.N/ACarrollwood Cmn2322$258,4781,197 Sq.Ft.6/20/2024Carrolton Way6733$463,6092,249 Sq.Ft.2/26/2025Carter Rd632$453,6672,226 Sq.Ft.3/16/2022Carver St2143$407,6672,227 Sq.Ft.9/19/2023Cascade Blvd4832$288,4471,665 Sq.Ft.4/11/2025Casey Martin Ct833$514,1432,535 Sq.Ft.7/13/2018Cassway Arch2242$457,5501,938 Sq.Ft.5/15/2025Castaway Ct453$712,7503,839 Sq.Ft.10/2/2020Castleberry Dr1653$670,2502,935 Sq.Ft.3/6/2024Castle Ct2432$201,9171,422 Sq.Ft.10/3/2023Castle Forbes Way244$1,913,5005,337 Sq.Ft.5/2/2022Catalina Ct354$869,0004,272 Sq.Ft.11/19/2015Catamount Ct1153$816,7273,563 Sq.Ft.11/26/2024Catbird Ln2133$489,0532,353 Sq.Ft.8/18/2022Catherine Ave1N/AN/A$380,000N/AN/ACatrina Ln3343$599,0002,736 Sq.Ft.5/27/2025Causeway Dr1632$422,1431,664 Sq.Ft.12/9/2024Cavalier Blvd31N/AN/AN/A44,475 Sq.Ft.4/23/2025Cavendish Way1743$639,0632,492 Sq.Ft.9/9/2024Cawdor Xing2054$1,399,8004,351 Sq.Ft.5/30/20241855 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
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
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
4136 2nd StChesapeake, VA 23324
Estimated Value $238,000
Living Area 1,040 SqFt
Beds 3
Baths 2
Year Built 1991
Property Type Single Family
Ownership Type Corporate
APN 1590000002800
Neighborhood South Norfolk
School District Chesapeake City Public Schools
573 Marc Smiley RdChesapeake, VA 23324
Estimated Value $300,000
Living Area 1,442 SqFt
Beds 2
Baths 2.5
Year Built 2016
Property Type Condominium
Ownership Type Individual
APN 1580001001350
Neighborhood South Norfolk
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
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
1042 Livingston AveChesapeake, VA 23324
Estimated Value $468,000
Living Area 2,945 SqFt
Beds 4
Baths 2.5
Year Built 2006
Property Type Single Family
Ownership Type Corporate
APN 1510000001170
Neighborhood South Norfolk
School District Chesapeake City Public Schools
101 Ford StChesapeake, VA 23323
Estimated Value $244,000
Living Area 1,120 SqFt
Beds 3
Baths 1
Year Built 1962
Property Type Single Family
Ownership Type Individual
APN 0261002000790
Neighborhood Deep Creek
School District Chesapeake City Public Schools
1048 Livingston AveChesapeake, VA 23324
Estimated Value $318,000
Living Area 1,623 SqFt
Beds 3
Baths 2.5
Year Built 2006
Property Type Single Family
Ownership Type Trust
APN 1510000001190
Neighborhood South Norfolk
School District Chesapeake City Public Schools
400 Harbour North DrChesapeake, VA 23320
Estimated Value $196,000
Living Area 1,216 SqFt
Beds 3
Baths 1.5
Year Built 1978
Property Type Townhouse
Ownership Type Individual
APN 0364003000260
Neighborhood Rivercrest
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
1231 Woods WayChesapeake, VA 23323
Estimated Value $393,000
Living Area 2,094 SqFt
Beds 4
Baths 2.5
Year Built 2000
Property Type Single Family
Ownership Type Individual
APN 0343023001180
Neighborhood Deep Creek
School District Chesapeake City Public Schools
4126 4th StChesapeake, VA 23324
Estimated Value $267,000
Living Area 1,586 SqFt
Beds 2
Baths 1.5
Year Built 1946
Property Type Single Family
Ownership Type Individual
APN 1600000000250
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