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
Blackwater Rd7732$498,0692,065 Sq.Ft.2/25/2025Blade Ct443$630,0003,761 Sq.Ft.10/15/2020Blair Ct1043$524,6252,164 Sq.Ft.3/20/2025Blairwood Ln2132$482,0532,035 Sq.Ft.3/27/2025Blake St2N/AN/AN/A3,444 Sq.Ft.N/ABlanche Ct442$345,7501,797 Sq.Ft.7/19/2023Blanche Dr3432$321,7061,448 Sq.Ft.5/20/2025Blaywicke Ct342$452,0001,731 Sq.Ft.3/28/2024Bleecker St1N/AN/AN/AN/A6/28/2013Bloom Ave2632$334,2801,548 Sq.Ft.4/28/2025Blossom Arch1442$492,3332,602 Sq.Ft.3/11/2024Blue Beech Way5533$414,0002,219 Sq.Ft.7/1/2024Blue Bell St1N/AN/AN/A43,800 Sq.Ft.12/28/2023Blue Bill Ct11N/AN/AN/AN/A10/8/2015Bluebird Dr832$400,2501,382 Sq.Ft.10/15/2020Bluecastle Way843$586,4292,541 Sq.Ft.10/21/2020Blue Goose Ct943$620,4293,225 Sq.Ft.1/26/2022Bluegrass Way1N/AN/AN/A359,146 Sq.Ft.N/ABlue Heron Ct543$543,0002,680 Sq.Ft.3/6/2024Blue Jay Ct543$557,2502,836 Sq.Ft.8/13/2020Blue Moon Cres554$759,6673,591 Sq.Ft.11/22/2013Blue Ridge Rd2543$523,6152,845 Sq.Ft.3/29/2024Blue Spruce Cir242$485,5001,962 Sq.Ft.7/16/2021Bluestem Ct443$600,0002,736 Sq.Ft.11/7/2024Bluewater Ct753$637,1673,334 Sq.Ft.12/10/2021Bluewing Ln843$513,2002,462 Sq.Ft.7/28/2021Bobby Ln2N/AN/A$375,0001,080 Sq.Ft.7/19/2024Bobby Ryan Way742$750,8572,615 Sq.Ft.4/30/2019Bobolink Cir353$562,0003,191 Sq.Ft.5/5/2025Bodine Ct443$542,0002,372 Sq.Ft.10/7/2021Bolton Cir343$597,0002,694 Sq.Ft.9/19/2001Bomar Dr2732$316,2401,376 Sq.Ft.12/4/2024Bond Ave332$341,6671,539 Sq.Ft.11/7/2022Bonnie View Arc554$677,6672,981 Sq.Ft.5/5/2022Bonsack Ct732$513,8572,481 Sq.Ft.1/5/2021Booker St2532$316,5711,624 Sq.Ft.6/5/2023Booth Ct643$629,8332,792 Sq.Ft.7/17/2006Bordeaux St633$372,0001,784 Sq.Ft.3/3/2023Border Ct731$241,5711,032 Sq.Ft.9/24/2024Border Rd2131$252,2676,083 Sq.Ft.3/20/2025Boston Ave3632$400,0571,551 Sq.Ft.3/24/2025Bosun Dr2031$252,1581,044 Sq.Ft.3/2/2022Boswell Dr543$474,0002,210 Sq.Ft.7/25/2017Bottom Quay1053$647,1003,149 Sq.Ft.8/25/2021Boundary St1N/AN/AN/A22,500 Sq.Ft.N/ABoundry St3N/AN/A$213,00037,450 Sq.Ft.N/ABounds Ave1231$268,7501,162 Sq.Ft.4/8/2025Bounty Reach1033$401,7781,816 Sq.Ft.4/24/2023Bourbon Ct853$698,3753,309 Sq.Ft.8/30/2021Bow Ct531$303,2001,082 Sq.Ft.4/23/2014Bowden Ave2631$261,8401,031 Sq.Ft.6/3/2025Bowling Green Ct842$414,8751,798 Sq.Ft.3/25/2024Bowling Green Trl6432$404,9841,612 Sq.Ft.5/27/2025Bow St1331$315,3331,312 Sq.Ft.8/2/2024Boxelder Ln423$248,7501,253 Sq.Ft.9/30/2020Boxwood Dr7032$320,2651,509 Sq.Ft.1/17/2025Boyette Ct932$326,8891,208 Sq.Ft.2/21/2024Boyle Ct633$403,4002,225 Sq.Ft.7/21/2020Bracey Way1043$829,0003,598 Sq.Ft.1/26/2015Bracknell Arch3022$195,8671,047 Sq.Ft.8/21/2024Braddock Landing Rd2154$608,3503,879 Sq.Ft.7/9/2021Bradford Ct243$622,5002,885 Sq.Ft.10/31/2007Bradwell Reach1143$556,2002,554 Sq.Ft.2/29/2024Bragg St1N/AN/AN/A1,600 Sq.Ft.N/ABraishfield Ct2033$335,2501,870 Sq.Ft.6/11/2024Bramblewood Ct1632$327,8131,382 Sq.Ft.10/28/2024Branch Dr2732$488,5602,239 Sq.Ft.7/10/2023Branchview Way1232$443,5002,021 Sq.Ft.3/19/2025Brandermill Ct542$480,2001,962 Sq.Ft.6/15/2000Brandermill Dr4742$494,6171,973 Sq.Ft.12/16/2024Brandon Ct1143$444,0002,002 Sq.Ft.7/14/2023Brandon Quay4843$448,5422,115 Sq.Ft.6/2/2025Brandon Way4042$465,8722,040 Sq.Ft.4/25/2025Brandy Ct543$519,4002,343 Sq.Ft.5/18/2022Brandywine Dr5042$312,1331,411 Sq.Ft.1/28/2025Brant Ct9N/AN/AN/AN/AN/ABrassie Ct1454$994,1434,872 Sq.Ft.7/16/2024Braves Trl1N/AN/AN/A287,268 Sq.Ft.N/ABreckenridge Ct842$468,5001,855 Sq.Ft.4/26/2024Breeze Ave2532$351,6001,630 Sq.Ft.3/27/2025Breeze Hill Cres1742$516,7501,958 Sq.Ft.7/10/2023Breeze Port Arch1743$333,5712,088 Sq.Ft.10/22/2024Breezy Pines Ct1032$336,6001,494 Sq.Ft.11/22/2024Breezy Pt1833$339,2781,755 Sq.Ft.10/18/2023Brennhaven Trl1843$573,8462,588 Sq.Ft.6/25/2019Brentford Ln2143$572,2782,493 Sq.Ft.3/13/2025Brentwood Arch743$772,8333,877 Sq.Ft.1/20/2021Brentwood Ct444$790,2503,682 Sq.Ft.8/29/2022Brians Way3443$550,5522,689 Sq.Ft.3/12/2025Briarcliff Pl442$363,7501,943 Sq.Ft.2/18/2025Briarfield Dr4932$449,1251,886 Sq.Ft.1/16/2025Briars Lndg743$515,5002,513 Sq.Ft.9/24/2021Briarwood Ct543$594,2002,762 Sq.Ft.1/4/2021Briarwood Dr2143$562,5262,456 Sq.Ft.1/5/2023Brice Ct1253$614,0003,225 Sq.Ft.3/3/2025Brickell Chase1333$342,2311,922 Sq.Ft.3/26/2024Bridge Dr1333$380,6671,635 Sq.Ft.5/22/2025Bridgefield Blvd1432$434,1542,061 Sq.Ft.3/4/2025Bridgeview Cir4443$497,5712,394 Sq.Ft.2/14/2023Bridgewood Way1054$806,6674,201 Sq.Ft.11/24/20201048 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
4305 Pickney LnChesapeake, VA 23324
Estimated Value $321,000
Living Area 1,720 SqFt
Beds 3
Baths 2.5
Year Built 2018
Property Type Condominium
Ownership Type Related
APN 1580001000710
Neighborhood South Norfolk
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
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
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
709 Helmsdale WayChesapeake, VA 23320
Estimated Value $388,000
Living Area 1,552 SqFt
Beds 3
Baths 2
Year Built 1987
Property Type Single Family
Ownership Type Related
APN 0368001000690
Neighborhood Rivercrest
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
4152 Williamson StChesapeake, VA 23324
Estimated Value $368,000
Living Area 3,274 SqFt
Beds 5
Baths 3
Year Built 1959
Property Type Single Family
Ownership Type Multiple
APN 1600000002510
Neighborhood South Norfolk
School District Chesapeake City Public Schools
704 Cordgrass CtChesapeake, VA 23320
Estimated Value $455,000
Living Area 2,189 SqFt
Beds 4
Baths 2.5
Year Built 1990
Property Type Single Family
Ownership Type Individual
APN 0369001000340
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1404 Earle AveChesapeake, VA 23324
Estimated Value $287,000
Living Area 1,828 SqFt
Beds 3
Baths 2
Year Built 1948
Property Type Single Family
Ownership Type Individual
APN 1590000003460
Neighborhood South Norfolk
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
809 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
1337 Dominion Lakes BlvdChesapeake, VA 23320
Estimated Value $625,000
Living Area 3,028 SqFt
Beds 5
Baths 2.5
Year Built 2002
Property Type Single Family
Ownership Type Related
APN 0352001000250
Neighborhood Rivercrest
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
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
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