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
Sir Lancelot Dr6742$325,3971,726 Sq.Ft.3/12/2025Sir Meliot Ct1342$325,5451,576 Sq.Ft.11/7/2023Sir Meliot Dr8542$328,8991,722 Sq.Ft.4/15/2025Sir Raleigh Dr143$628,0003,150 Sq.Ft.11/10/2014Sir Thomas Ct453$506,0002,708 Sq.Ft.6/3/2022Sir Thomas Dr1553$516,8462,685 Sq.Ft.3/14/2024Sir Tristram Ct832$312,0001,575 Sq.Ft.4/2/2024Sir Walter Cres3342$428,1522,003 Sq.Ft.5/27/2025Sir Walter Ct242$485,5002,579 Sq.Ft.8/25/2003Sis Ct654$752,6673,343 Sq.Ft.3/18/2025Sitka Spruce Rd1823$248,7781,254 Sq.Ft.1/14/2025Sivills Lndg332$406,6671,631 Sq.Ft.6/8/2020Skicoat St843$575,6672,621 Sq.Ft.5/9/2022Skipjack Ln1442$419,0771,834 Sq.Ft.10/15/2021Skipperlin Way753$683,0002,870 Sq.Ft.5/28/2024Skylark Ct1143$554,0912,624 Sq.Ft.8/22/2023Skyline Cir1243$652,0833,007 Sq.Ft.5/31/2023Slate St2842$496,9622,169 Sq.Ft.2/12/2025Sloane St1822$304,5561,518 Sq.Ft.3/21/2024Sloop Trl5132$160,9391,349 Sq.Ft.2/5/2025Sluice Ct742$509,1672,272 Sq.Ft.2/11/2025Small St1N/AN/A$237,000N/AN/ASmith Ave3332$337,0954,598 Sq.Ft.11/5/2024Smith Douglas Rd2N/AN/AN/A9,885 Sq.Ft.N/ASmithson Dr1832$413,8241,486 Sq.Ft.6/4/2025Smokestack Ln843$539,1252,743 Sq.Ft.9/17/2024Smokey Mountain Ct543$630,2002,999 Sq.Ft.8/12/2021Smokey Mountain Trl6943$650,1213,094 Sq.Ft.5/19/2025Snowberry Ln1932$365,3331,674 Sq.Ft.8/21/2024Snowden St3N/AN/A$1,035,0001,282 Sq.Ft.10/4/2024Snow Goose Dr1N/AN/AN/A168 Sq.Ft.N/ASoft Pine Ct453$735,0003,093 Sq.Ft.1/24/2025Solomon St1932$281,4212,827 Sq.Ft.12/19/2024Sol Thorpe Ln1243$434,4172,603 Sq.Ft.5/14/2025Somb Moore Ways1443$422,9291,958 Sq.Ft.4/10/2024Somerton Ln842$509,7502,055 Sq.Ft.5/16/2019Sommerton Way3133$508,9352,471 Sq.Ft.4/28/2025Sommerville Cres4232$268,2501,364 Sq.Ft.12/15/2023Sondej Ave4532$389,4231,831 Sq.Ft.5/9/2023Songbird Ln1533$391,4671,779 Sq.Ft.8/28/2023Sorrento Dr2942$434,7241,939 Sq.Ft.12/23/2020Sound Ct654$780,0003,563 Sq.Ft.4/26/2023Southall Ct1332$334,2311,375 Sq.Ft.3/26/2025Southampton Ct643$438,2002,196 Sq.Ft.8/27/2021Southern Oaks Dr1343$562,5002,595 Sq.Ft.4/1/2022Southern Pines Dr6142$382,2201,788 Sq.Ft.5/29/2025Southfield Dr1643$477,9382,144 Sq.Ft.6/5/2024Southport Ave4332$290,4651,306 Sq.Ft.5/2/2024South Rd1032$397,5001,690 Sq.Ft.2/13/2025Southway St132$385,0002,421 Sq.Ft.8/23/2010Southwood Ct753$730,4293,494 Sq.Ft.7/19/2021Southwood Dr643$631,5002,722 Sq.Ft.5/31/2019Spadina Ave3532$260,8001,359 Sq.Ft.5/29/2025Spanish Moss Dr3N/AN/AN/A192 Sq.Ft.N/ASpar Ct431$267,7501,116 Sq.Ft.9/19/2024S Park Ct1N/AN/AN/AN/AN/ASparks Trce1453$694,6923,058 Sq.Ft.10/23/2023Sparrow Ct332$434,3332,126 Sq.Ft.6/17/2022Sparrow Ln431$331,2501,478 Sq.Ft.5/2/2019Sparrow Rd27332$357,3352,328 Sq.Ft.5/30/2025Spar St3231$268,5671,194 Sq.Ft.11/1/2024Speedy Ave5232$333,5311,805 Sq.Ft.3/22/2023Speight Lyons Loop4843$545,8512,752 Sq.Ft.5/28/2025Spellbound Pt643$650,6672,826 Sq.Ft.5/15/2025Spencer Ln1N/AN/AN/AN/AN/ASpice Bush Ct2843$527,8462,667 Sq.Ft.10/28/2024Spice Quay753$605,8002,971 Sq.Ft.7/31/2023Spincaster Ln1543$549,8462,702 Sq.Ft.3/13/2024Spinnaker Ct3622$261,5001,117 Sq.Ft.4/18/2024Spinners Way1532$336,2001,627 Sq.Ft.12/16/2024Spoonbill Ct9N/AN/AN/AN/AN/ASpringbrook Ln1443$471,3852,189 Sq.Ft.11/21/2023Springdale Rd1832$313,6671,546 Sq.Ft.4/29/2025Springer Ln1322$285,5451,613 Sq.Ft.4/23/2025Springfield Ave1932$321,1671,450 Sq.Ft.5/19/2023Spring Maple Ct1343$531,9232,618 Sq.Ft.5/15/2024Spring Meadow Cres5542$377,2312,005 Sq.Ft.4/28/2025Spring Rd1042$362,7782,245 Sq.Ft.11/21/2024Spruce Forest Ct943$713,5563,450 Sq.Ft.6/29/2022Spruce Ln2443$568,2863,082 Sq.Ft.5/22/2025Spurlane Cir4842$487,9091,830 Sq.Ft.11/4/2024Spurlock Ct943$562,4442,629 Sq.Ft.2/3/2022Spurlock Way1843$568,9412,718 Sq.Ft.12/11/2024Squire Ct1242$338,6361,821 Sq.Ft.4/17/2024Squirrel Run1053$474,4442,819 Sq.Ft.5/11/2021Stacey Pl333$467,3331,780 Sq.Ft.N/AStadium Dr1343$509,7274,740 Sq.Ft.8/7/2024Stafford Dr5322$205,6981,194 Sq.Ft.1/17/2025Staffordshire Ct553$556,2002,709 Sq.Ft.7/20/2020Staley Crest Way1242$482,5832,205 Sq.Ft.6/12/2023Stalham Rd6832$291,9233,210 Sq.Ft.11/21/2024Stanhope Close842$634,2862,642 Sq.Ft.8/2/2024Stanhope Gdns2743$475,2862,477 Sq.Ft.11/7/2024Stanley Dr2031$317,8001,177 Sq.Ft.4/8/2025Stanmore Ct542$464,6001,877 Sq.Ft.11/1/2019Starboard Rd5332$301,5801,353 Sq.Ft.5/23/2025Star Ct854$731,5003,463 Sq.Ft.12/16/2024Stardale Cir343$552,3332,602 Sq.Ft.9/27/2024Stardale Dr4143$527,4632,235 Sq.Ft.1/3/2024Starina Ct342$427,0002,153 Sq.Ft.5/8/20131709 Foremast LoopChesapeake, VA 23323
Estimated Value $379,000
Living Area 1,720 SqFt
Beds 3
Baths 2.5
Year Built 2020
Property Type Condominium
Ownership Type Related
APN 0354003002410
Neighborhood Deep Creek
School District Chesapeake City Public Schools
1207 Basswood CtChesapeake, VA 23320
Estimated Value $273,000
Living Area 1,264 SqFt
Beds 3
Baths 2.5
Year Built 1987
Property Type Townhouse
Ownership Type Individual
APN 0366008000410
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
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
832 Wickford DrChesapeake, VA 23320
Estimated Value $186,000
Living Area 860 SqFt
Beds 2
Baths 1
Year Built 1985
Property Type Townhouse
Ownership Type Individual
APN 0367001000330
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
1100 Railroad AveChesapeake, VA 23324
Estimated Value $328,000
Living Area 1,931 SqFt
Beds 3
Baths 2.5
Year Built 2003
Property Type Single Family
Ownership Type Individual
APN 1590000004042
Neighborhood South Norfolk
School District Chesapeake City Public Schools
1819 Sunsprite LoopChesapeake, VA 23323
Estimated Value $612,000
Living Area 2,924 SqFt
Beds 4
Baths 2.5
Year Built 2007
Property Type Single Family
Ownership Type Related
APN 0354001000110
Neighborhood Deep Creek
School District Chesapeake City Public Schools
4003 4th StChesapeake, VA 23324
Estimated Value $249,000
Living Area 1,164 SqFt
Beds 3
Baths 1
Year Built 1958
Property Type Single Family
Ownership Type Related
APN 1600000000080
Neighborhood South Norfolk
School District Chesapeake City Public Schools
705 Montrose CtChesapeake, VA 23320
Estimated Value $288,000
Living Area 1,516 SqFt
Beds 3
Baths 2.5
Year Built 1991
Property Type Townhouse
Ownership Type Individual
APN 0367002001510
Neighborhood Rivercrest
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
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
500 Plainfield AveChesapeake, VA 23320
Estimated Value $279,000
Living Area 1,274 SqFt
Beds 3
Baths 1
Year Built 1940
Property Type Single Family
Ownership Type Individual
APN 0360000001170
Neighborhood Rivercrest
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
1972 Millville RdChesapeake, VA 23323
Estimated Value $624,000
Living Area 2,586 SqFt
Beds 4
Baths 3
Year Built 2007
Property Type Single Family
Ownership Type Related
APN 0344001000040
Neighborhood Deep Creek
School District Chesapeake City Public Schools
1002 Godwin AveChesapeake, VA 23324
Estimated Value $364,000
Living Area 1,924 SqFt
Beds 4
Baths 2.5
Year Built 2013
Property Type Single Family
Ownership Type Individual
APN 1520000002620
Neighborhood South Norfolk
School District Chesapeake City Public Schools