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
Waterfront Dr1032$471,7781,805 Sq.Ft.10/8/2024Water Hickory Ct1033$477,1002,311 Sq.Ft.1/24/2025Waterlawn Ave2632$330,9581,400 Sq.Ft.10/21/2024Watermill Grv2343$495,5912,782 Sq.Ft.7/21/2023Water Oak Ct1343$965,8463,981 Sq.Ft.11/6/2024Watershed Ct3643$655,3232,577 Sq.Ft.12/12/2024Waterside Dr6843$491,8622,492 Sq.Ft.6/4/2025Waters Rd15242$506,8782,332 Sq.Ft.6/3/2025Waterstock Ct1442$484,6152,018 Sq.Ft.6/10/2024Waterstone Ct743$475,4002,210 Sq.Ft.8/3/2020Waterstone Cv542$543,2502,751 Sq.Ft.4/23/2021Waterstone Way743$547,7142,793 Sq.Ft.4/14/2021Water View Cir1754$1,389,4674,836 Sq.Ft.3/29/2022Waterway Cir5342$494,8602,121 Sq.Ft.8/1/2024Waterway Ct832$466,7141,895 Sq.Ft.9/22/2023Waterwheel Rd1854$1,072,6884,383 Sq.Ft.9/3/2024Watson Rd1N/AN/AN/A13,083 Sq.Ft.12/20/2023Watsons Glen Ct543$630,0003,264 Sq.Ft.3/19/2021Watsons Glen Rd443$593,0003,343 Sq.Ft.7/28/2021Watson Way642$515,1672,404 Sq.Ft.3/5/2024Watts Brothers Ln2N/AN/A$190,000702 Sq.Ft.5/2/2025Waxwing Ct343$600,3333,276 Sq.Ft.3/15/2017Waycroft Reach1543$589,0832,328 Sq.Ft.1/10/2025Way Ct743$512,0002,432 Sq.Ft.11/1/2024Waylen Loop832$444,3751,988 Sq.Ft.2/23/2023Wayne Ave1N/AN/AN/A656 Sq.Ft.2/3/2005Weatherby Ct1142$471,0911,952 Sq.Ft.4/9/2025Weathley Ave10N/AN/A$226,000N/AN/AWeaver Ln2N/AN/AN/A213,758 Sq.Ft.7/28/2021Weaver St1N/AN/AN/A162,404 Sq.Ft.N/AWeber Ave9932$324,9001,546 Sq.Ft.6/26/2024Webster Ave932$308,8751,371 Sq.Ft.6/5/2024Wecht Ct643$541,8002,281 Sq.Ft.12/22/2019Wedgewood Cir1132$372,2731,666 Sq.Ft.9/12/2024Wedgewood Dr1232$433,8182,273 Sq.Ft.8/1/2024Weeping Cedar Ct542$443,4001,974 Sq.Ft.3/31/2023Weeping Cedar Trl3142$445,8152,095 Sq.Ft.3/12/2025Weeping Willow Dr7342$481,7941,852 Sq.Ft.12/2/2024Weiss Ln3432$440,8571,763 Sq.Ft.4/21/2025Welch Ln4032$316,3611,744 Sq.Ft.10/21/2024Welcome Rd1N/AN/AN/A147,882 Sq.Ft.4/23/2025Welles Ct2332$364,9091,525 Sq.Ft.4/30/2025Wellington Ave832$268,0001,237 Sq.Ft.N/AWendover Ct632$424,6002,022 Sq.Ft.11/18/2020Wenger Rd1342$489,4622,269 Sq.Ft.12/16/2024Wentworth Dr744$733,1673,380 Sq.Ft.12/4/2020Werdna Ln1544$754,9293,149 Sq.Ft.7/1/2024Wesley Rd3342$376,6332,030 Sq.Ft.1/14/2025Wessex Dr1433$519,9292,430 Sq.Ft.3/5/2025Westborough Dr1943$402,7892,225 Sq.Ft.12/14/2022Westbrook Ln533$371,2001,752 Sq.Ft.4/1/2021Westcove Ln1443$488,1002,662 Sq.Ft.5/14/2024Westerly Ct553$636,6002,962 Sq.Ft.5/23/2023Western Branch Blvd59N/AN/AN/A18,102 Sq.Ft.4/24/2025Westfield Ct342$469,0002,224 Sq.Ft.9/20/2023Westgate Ct931$229,556980 Sq.Ft.4/25/2025Westgate St1631$242,4441,001 Sq.Ft.12/9/2024Westmoreland Ct1042$456,3332,371 Sq.Ft.3/10/2023Weston Arch1243$465,0002,762 Sq.Ft.9/1/2021Westonia Rd5842$382,9271,725 Sq.Ft.5/2/2025West Rd19932$553,9122,541 Sq.Ft.5/19/2025Westwood Ave532$286,0001,447 Sq.Ft.12/21/2021Wexford Ct653$710,0003,556 Sq.Ft.3/15/2023Wharfs Lndg442$397,2501,616 Sq.Ft.4/1/2022Wheatfield Way642$521,1672,657 Sq.Ft.6/18/2024Wheeling Ave321$359,3331,426 Sq.Ft.7/22/2020Whelp Way2133$440,7502,215 Sq.Ft.5/27/2025Whimbrel Ave1433$269,3571,767 Sq.Ft.N/AWhippoorwill Trce853$640,5002,818 Sq.Ft.5/14/2025Whisper Hollow Dr4942$534,6812,008 Sq.Ft.6/24/2024Whispering Oak Cir1742$363,5631,780 Sq.Ft.4/4/2022Whisper Walk6843$416,6001,930 Sq.Ft.6/2/2023Whistle Town Ct543$549,6002,477 Sq.Ft.10/29/2014Whistle Town Rd1443$529,5002,294 Sq.Ft.6/14/2024Whistling Rd2433$445,2272,114 Sq.Ft.4/15/2025Whitburn Ter4133$477,9762,227 Sq.Ft.5/13/2025Whitebark Rd423$252,2501,262 Sq.Ft.7/25/2024White Cap Crst3443$374,2502,168 Sq.Ft.2/3/2025White Cedar Dr2242$409,4501,785 Sq.Ft.8/23/2024Whitechapel Arch10632$276,3851,473 Sq.Ft.4/24/2025White Dogwood Dr3843$703,2353,461 Sq.Ft.9/20/2024White Egret Cv753$674,1432,858 Sq.Ft.7/27/2023Whitehall Ct442$580,2502,384 Sq.Ft.4/26/2021Whitehaven Cres3942$370,9742,005 Sq.Ft.3/27/2025Whitehaven Ct1142$373,9001,778 Sq.Ft.3/19/2018White Head Ct9N/AN/AN/AN/AN/AWhite Heron Run844$747,2864,815 Sq.Ft.9/9/2024Whitehurst Lndg1053$711,0003,216 Sq.Ft.5/13/2022Whitehurst Rd1532$435,9232,021 Sq.Ft.4/28/2023White Oak Ct3132$355,7931,502 Sq.Ft.9/30/2024White Oak Xing4N/AN/AN/AN/AN/AWhite Owl Cres1143$559,9092,748 Sq.Ft.1/17/2024White Pine Dr2931$269,9641,241 Sq.Ft.2/20/2024White Rock Bnd1443$417,1541,794 Sq.Ft.4/29/2025Whites Landing Ct243$630,0002,383 Sq.Ft.11/30/2020Whites Lndg1943$690,5713,058 Sq.Ft.1/29/2025Whitestone Ave1632$289,1431,376 Sq.Ft.12/19/2024White Swallow Way1242$553,7272,804 Sq.Ft.1/4/2022White Tail Ct1343$435,7782,191 Sq.Ft.5/1/2024Whitfield Ln2533$343,3182,020 Sq.Ft.4/28/20251702 Foremast LoopChesapeake, VA 23323
Estimated Value $384,000
Living Area 1,760 SqFt
Beds 3
Baths 2.5
Year Built 2020
Property Type Condominium
Ownership Type Individual
APN 0354003002320
Neighborhood Deep Creek
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
557 River Creek RdChesapeake, VA 23320
Estimated Value $311,000
Living Area 1,353 SqFt
Beds 3
Baths 2
Year Built 1955
Property Type Single Family
Ownership Type Related
APN 0362001002010
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
446 Supplejack CtChesapeake, VA 23320
Estimated Value $467,000
Living Area 2,293 SqFt
Beds 4
Baths 2.5
Year Built 1990
Property Type Single Family
Ownership Type Related
APN 0369003000120
Neighborhood Rivercrest
School District Chesapeake City Public Schools
621 Pine BndChesapeake, VA 23320
Estimated Value $246,000
Living Area 1,273 SqFt
Beds 3
Baths 2.5
Year Built 1979
Property Type Townhouse
Ownership Type Individual
APN 0366001000150
Neighborhood Rivercrest
School District Chesapeake City Public Schools
736 Huntly DrChesapeake, VA 23320
Estimated Value $251,000
Living Area 1,240 SqFt
Beds 3
Baths 1.5
Year Built 1990
Property Type Townhouse
Ownership Type Corporate
APN 0367002000640
Neighborhood Rivercrest
School District Chesapeake City Public Schools
108 Duffield PlChesapeake, VA 23320
Estimated Value $349,000
Living Area 1,530 SqFt
Beds 3
Baths 1.5
Year Built 1965
Property Type Single Family
Ownership Type Individual
APN 0271009000280
Neighborhood Rivercrest
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
1785 Shipyard RdChesapeake, VA 23323
Estimated Value $297,000
Living Area 1,100 SqFt
Beds 2
Baths 1.5
Year Built 1961
Property Type Single Family
Ownership Type Individual
APN 0350000000030
Neighborhood Deep Creek
School District Chesapeake City Public Schools
504 Rosewood TerChesapeake, VA 23320
Estimated Value $412,000
Living Area 1,629 SqFt
Beds 3
Baths 1.5
Year Built 1966
Property Type Single Family
Ownership Type Related
APN 0361008000890
Neighborhood Rivercrest
School District Chesapeake City Public Schools
902 Godwin AveChesapeake, VA 23324
Estimated Value $364,000
Living Area 1,972 SqFt
Beds 4
Baths 3
Year Built 2018
Property Type Single Family
Ownership Type Related
APN 1510000000720
Neighborhood South Norfolk
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
1702 Willow Point ArchChesapeake, VA 23320
Estimated Value $241,000
Living Area 1,244 SqFt
Beds 2
Baths 2
Year Built 2000
Property Type Condominium
Ownership Type Related
APN 0367013000720
Neighborhood Rivercrest
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
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