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
Sand Bunker Arch1822$299,9441,435 Sq.Ft.5/8/2025Sandcastle Ct642$497,6002,503 Sq.Ft.7/28/2022Sandcastle Way1343$509,5832,637 Sq.Ft.1/14/2022Sandchip Ter2132$503,2502,116 Sq.Ft.2/28/2025Sand Drift Ct942$513,1112,046 Sq.Ft.12/3/2020Sanderson Rd17543$781,0082,888 Sq.Ft.5/21/2025Sandhurst Ct542$448,2001,847 Sq.Ft.6/27/2023Sandlewood Ln1342$498,0772,151 Sq.Ft.7/22/2024Sandown Crst853$616,5003,119 Sq.Ft.7/25/2013Sand Pebble Ct1222$199,600926 Sq.Ft.1/31/2025Sandpiper Ln1343$722,2503,406 Sq.Ft.7/7/2024Sandstone Ct543$728,5003,173 Sq.Ft.10/17/2022Sand Trap Ct354$947,0004,751 Sq.Ft.10/17/1998Sand Wedge Ct843$539,0002,407 Sq.Ft.4/17/2025Sand Willow Ct643$551,5002,439 Sq.Ft.8/5/2021Sand Willow Dr2443$580,5502,994 Sq.Ft.9/30/2022Sandy Hill Way1342$536,0002,236 Sq.Ft.5/27/2021Sandy Pines Ct642$328,0001,412 Sq.Ft.4/29/2025Sandy Pines Way2032$332,1581,492 Sq.Ft.5/1/2025Sandy Point Ln1332$305,9171,767 Sq.Ft.4/1/2024Sandy Rd233$371,0001,630 Sq.Ft.6/27/2024Sanibel Ln5543$542,0192,621 Sq.Ft.5/16/2025Sanjo Farms Dr2743$650,6522,969 Sq.Ft.6/4/2025San Juan Dr343$531,0002,263 Sq.Ft.4/30/2019San Pedro Dr6043$609,9822,775 Sq.Ft.4/10/2025San Roman Ct2622$292,2001,219 Sq.Ft.3/11/2025San Roman Dr10622$293,3651,240 Sq.Ft.11/6/2024San Salvador Dr3632$367,4291,651 Sq.Ft.2/25/2025Santa Maria Dr2732$370,0381,587 Sq.Ft.8/30/2024Santeetlah Ave3631$299,8331,326 Sq.Ft.4/4/2024Santiago Ct843$545,6672,605 Sq.Ft.1/13/2025Sapient Ter643$671,2002,843 Sq.Ft.5/13/2025Sapphire Rd854$709,5002,938 Sq.Ft.3/8/2024Sara Dr1N/AN/AN/AN/AN/ASarasota Arch1353$687,8333,190 Sq.Ft.7/14/2024Sarvin Ct443$573,5002,644 Sq.Ft.10/25/2017Sasparilla Ct643$591,4002,918 Sq.Ft.12/16/2021Satinwood Ct1453$641,1543,012 Sq.Ft.10/7/2024Saul Ct532$310,0001,227 Sq.Ft.6/10/2021Saul Dr2332$335,5001,587 Sq.Ft.6/22/2023Saunders Ln333N/A1,306 Sq.Ft.N/ASavannah Dr1654$930,1544,235 Sq.Ft.12/18/2023Savory Cres2043$480,0002,331 Sq.Ft.5/14/2024Sawblade Cir742$530,7142,531 Sq.Ft.11/5/2024Sawmark Ct543$567,5002,738 Sq.Ft.8/11/2021Sawmill Arch1043$475,7002,026 Sq.Ft.2/7/2025Saw Mill Ct1232$322,1821,431 Sq.Ft.7/20/2023Sawtooth Cir743$535,3332,652 Sq.Ft.11/9/2022Sawyers Arch2142$500,4292,293 Sq.Ft.6/25/2024Sawyers Mill Xing5743$538,8302,701 Sq.Ft.8/6/2024Saxe Ct343$533,3332,793 Sq.Ft.6/26/2019Saxon Ct642$318,0001,741 Sq.Ft.7/24/2018Scaleboard Cir1053$543,8892,634 Sq.Ft.1/23/2025Scarborough Dr3632$441,5632,168 Sq.Ft.10/18/2024Scarlet Oak Ct2832$367,0361,538 Sq.Ft.6/30/2023Scarlett Dr2332$463,7732,052 Sq.Ft.6/30/2023Scaup Ct9N/AN/AN/AN/AN/AScenic Blvd4842$486,5002,092 Sq.Ft.3/28/2025Scenic Pkwy16N/AN/AN/A12,146 Sq.Ft.12/3/2024Schaefer Ave3943$480,9662,450 Sq.Ft.2/4/2025Schiemann Ct444$630,2503,029 Sq.Ft.3/4/2022Scholastic Way1N/AN/AN/A16,360 Sq.Ft.N/ASchool House Rd5943$632,0362,898 Sq.Ft.6/3/2025Schooner Trl11732$208,9051,448 Sq.Ft.4/17/2025Scone Castle Loop4055$1,643,6495,396 Sq.Ft.4/30/2025Scoonie Pointe Dr7332$427,3942,045 Sq.Ft.6/4/2025Scoter Ct9N/AN/AN/AN/AN/AScotfield Dr4142$430,8651,950 Sq.Ft.8/9/2024Scotia Dr6031$267,4741,211 Sq.Ft.5/28/2025Scotland Ln454$767,0004,355 Sq.Ft.11/30/2010Scotsman Run1243$652,9003,443 Sq.Ft.9/28/2020Scott Ave421$264,0001,006 Sq.Ft.7/31/2006Scotties Ln1N/AN/A$269,000858 Sq.Ft.6/18/2021Screech Ct554$702,8003,782 Sq.Ft.5/16/2014Seaboard Ave14932$266,3132,233 Sq.Ft.5/6/2025Seaboard Ct1N/AN/AN/A3,742 Sq.Ft.N/ASeaborn Way543$630,0002,615 Sq.Ft.4/15/2022Seabreeze Ct3622$251,1431,028 Sq.Ft.5/13/2025Seabrooke Ln742$517,0002,228 Sq.Ft.7/24/2023Seabrooke Pt843$524,3752,423 Sq.Ft.10/11/2022Sea Cliff Rd1432$323,0711,513 Sq.Ft.1/9/2024Seaforth Rd942$451,6672,162 Sq.Ft.9/29/2020Seagrass Reach1943$660,6673,649 Sq.Ft.7/25/2022Seagull Ct653$666,6673,042 Sq.Ft.9/30/2020Seahorse Run8123$270,6631,572 Sq.Ft.4/24/2025Sean Dr2832$320,7201,527 Sq.Ft.5/21/2025Sea Palling Ln943$433,2502,256 Sq.Ft.4/25/2025Seastone Trce4443$546,7072,667 Sq.Ft.2/24/2025Seaton Cir1232$270,7501,321 Sq.Ft.12/12/2023Secretariat Way654$767,6673,756 Sq.Ft.1/11/2021Seddon Ct642$466,5001,693 Sq.Ft.2/26/2024Sedgefield Ct3333$293,7811,442 Sq.Ft.5/15/2025Sedgewood Ct843$470,8572,102 Sq.Ft.4/19/2024Seever St1N/AN/A$237,000N/A11/16/2020Selborne Pl1N/AN/A$367,000N/A6/19/2014Seldon Rd532$337,0001,508 Sq.Ft.5/19/2025Sendero Ct4322$292,6431,419 Sq.Ft.3/12/2025Seneca Ave642$363,8331,536 Sq.Ft.N/ASentinel Dr12N/AN/AN/A33,198 Sq.Ft.2/20/2025Sentry Dr1N/AN/AN/A7,134 Sq.Ft.N/A1616 Woodbriar LnChesapeake, VA 23323
Estimated Value $303,000
Living Area 1,400 SqFt
Beds 4
Baths 2
Year Built 1983
Property Type Single Family
Ownership Type Multiple
APN 0343017000220
Neighborhood Deep Creek
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
2028 Warfield StChesapeake, VA 23324
Estimated Value $255,000
Living Area 1,284 SqFt
Beds 3
Baths 2
Year Built 1987
Property Type Single Family
Ownership Type Individual
APN 1600000002830
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
4315 Salt Marsh LnChesapeake, VA 23324
Estimated Value $327,000
Living Area 1,960 SqFt
Beds 3
Baths 2.5
Year Built 2015
Property Type Condominium
Ownership Type Individual
APN 1580001002050
Neighborhood South Norfolk
School District Chesapeake City Public Schools
308 Esplanade PlChesapeake, VA 23320
Estimated Value $356,000
Living Area 1,849 SqFt
Beds 3
Baths 2.5
Year Built 1994
Property Type Townhouse
Ownership Type Multiple
APN 0367008000200
Neighborhood Rivercrest
School District Chesapeake City Public Schools
4125 3rd StChesapeake, VA 23324
Estimated Value $218,000
Living Area 924 SqFt
Beds 2
Baths 1
Year Built 1952
Property Type Single Family
Ownership Type Individual
APN 1590000003730
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
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
926 Avast WayChesapeake, VA 23323
Estimated Value $377,000
Living Area 1,720 SqFt
Beds 3
Baths 2.5
Year Built 2018
Property Type Condominium
Ownership Type Individual
APN 0354003000600
Neighborhood Deep Creek
School District Chesapeake City Public Schools
1333 Winslow AveChesapeake, VA 23323
Estimated Value $329,000
Living Area 1,500 SqFt
Beds 4
Baths 2
Year Built 1977
Property Type Single Family
Ownership Type Individual
APN 0255002000130
Neighborhood Deep Creek
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
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
4128 1st StChesapeake, VA 23324
Estimated Value $371,000
Living Area 1,972 SqFt
Beds 4
Baths 3
Year Built 2009
Property Type Single Family
Ownership Type Related
APN 1590000002342
Neighborhood South Norfolk
School District Chesapeake City Public Schools
1233 Marge DrChesapeake, VA 23320
Estimated Value $302,000
Living Area 1,336 SqFt
Beds 3
Baths 1.5
Year Built 1975
Property Type Single Family
Ownership Type Individual
APN 0272001000440
Neighborhood Rivercrest
School District Chesapeake City Public Schools
708 Bulrush CtChesapeake, VA 23320
Estimated Value $471,000
Living Area 2,189 SqFt
Beds 4
Baths 2.5
Year Built 1991
Property Type Single Family
Ownership Type Individual
APN 0369001000470
Neighborhood Rivercrest
School District Chesapeake City Public Schools