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
Woodbaugh Dr9932$322,0421,450 Sq.Ft.2/26/2025Woodberry Dr2843$490,5192,356 Sq.Ft.5/20/2025Wood Bird Ct542$473,8001,988 Sq.Ft.N/AWoodbriar Ln1532$308,0671,224 Sq.Ft.10/22/2024Woodbridge Ct242$493,5002,408 Sq.Ft.N/AWoodbridge Dr5742$493,5932,124 Sq.Ft.4/30/2025Woodcliff Arch454$743,3334,058 Sq.Ft.10/29/2024Woodcott Dr6442$543,7632,185 Sq.Ft.6/3/2025Woodcroft Ln1442$445,9292,575 Sq.Ft.4/29/2022Wooddale Ct1642$366,0671,576 Sq.Ft.12/13/2024Wood Duck Ct433$405,5002,230 Sq.Ft.11/9/2016Wood Duck Ln2942$454,5932,100 Sq.Ft.2/1/2023Wooded Hill Arch1153$597,5002,818 Sq.Ft.7/25/2022Woodford Dr2432$460,0432,009 Sq.Ft.6/28/2023Woodgate Arch10222$255,8701,173 Sq.Ft.3/24/2025Woodglen Dr2742$505,2502,150 Sq.Ft.9/20/2023Woodgrove St1533$358,2141,804 Sq.Ft.3/13/2025Woodhurst Ln1843$705,8893,306 Sq.Ft.5/2/2022Woodlake Cir12N/AN/AN/A106,816 Sq.Ft.11/7/2022Woodlake Dr33N/AN/A$683,00056,142 Sq.Ft.8/22/2024Woodland Dr7542$450,5082,202 Sq.Ft.12/9/2024Woodland Terrace Dr3431$260,2121,126 Sq.Ft.1/6/2025Woodmark Trl2432$253,8751,474 Sq.Ft.6/13/2024Woodmill St4133$358,1031,801 Sq.Ft.1/20/2023Woodmont Dr333$515,0001,887 Sq.Ft.12/15/2021Woodmoor Ct843$547,0002,811 Sq.Ft.3/13/2019Wood Nymph Ln5453$659,0432,864 Sq.Ft.5/29/2025Woodrow Ct2542$465,2401,892 Sq.Ft.6/9/2023Woods Edge Ct442$469,0001,985 Sq.Ft.3/16/2023Woodside Ct3942$445,7892,036 Sq.Ft.5/29/2025Woodsmans Ct943$451,2222,072 Sq.Ft.4/25/2024Woodsmans Reach3043$452,9292,147 Sq.Ft.8/15/2024Woodsmere Rd254$969,5004,111 Sq.Ft.4/15/2019Woodspring Arch743$510,4292,408 Sq.Ft.4/12/2017Woodstock Ct1833$359,7221,803 Sq.Ft.9/20/2024Wood Stork Dr653$571,6672,822 Sq.Ft.9/16/2021Woodstream Ct1842$540,8892,083 Sq.Ft.3/19/2024Woodstream Way2642$538,6802,031 Sq.Ft.6/16/2023Woods Way2432$380,2921,785 Sq.Ft.5/16/2025Woodview Lair943$619,0003,146 Sq.Ft.5/26/2023Woodwind Way1543$611,0002,710 Sq.Ft.7/25/2023Woodworkers Ct433$520,50034,800 Sq.Ft.6/25/2007Woody Ridge Ct743$829,7143,346 Sq.Ft.8/19/2014Wooten Ln532$308,2001,310 Sq.Ft.5/30/2025Wormington Dr2642$472,2401,780 Sq.Ft.4/25/2023Wortham Ct1442$379,7861,653 Sq.Ft.11/15/2024Worthing Ln1432$223,3571,334 Sq.Ft.2/11/2020Wright Ave3732$275,9441,487 Sq.Ft.1/31/2025Wyant Ct643$378,6002,256 Sq.Ft.1/6/2024Wye Oak Way1442$409,5002,084 Sq.Ft.2/28/2024Wyfold Ct843$518,8752,635 Sq.Ft.9/2/2022Wymers Ct2042$545,4712,308 Sq.Ft.4/24/2024Wynngate Ct542$434,0001,928 Sq.Ft.6/14/2024Wynngate Dr4232$424,3501,725 Sq.Ft.2/29/2024Yacht Dr3N/AN/AN/A124,786 Sq.Ft.8/5/2016Yadkin Rd3242$255,60015,291 Sq.Ft.12/10/2024Yager Ct531$259,0002,965 Sq.Ft.N/AYakima Rd1031$266,2001,084 Sq.Ft.7/10/2024Yancy Ct1443$570,0772,628 Sq.Ft.3/17/2023Yardarm Way533$415,0001,984 Sq.Ft.2/14/2019Yateley Ct443$545,3332,498 Sq.Ft.2/25/2009Yates Cir543$475,2002,142 Sq.Ft.6/17/2021Yeadon Rd3631$252,7141,161 Sq.Ft.3/12/2025Yellow Pine Cres2022$200,5001,020 Sq.Ft.9/13/2024York Dr1043$457,8002,152 Sq.Ft.1/10/2022Yorkshire Ct753$614,8333,042 Sq.Ft.2/3/2022Yorkshire Dr1543$622,7862,913 Sq.Ft.2/1/2024Yorkshire Trl4743$627,0232,881 Sq.Ft.11/3/2023York St642$357,1671,974 Sq.Ft.12/30/2021Youngman Rd3231$254,0651,063 Sq.Ft.5/27/2025Youngstown Ct1254$799,3643,823 Sq.Ft.3/25/2025Yuban St753$636,6673,489 Sq.Ft.9/20/2024Yupo Ct6N/AN/AN/A14,707 Sq.Ft.6/8/2023Zari Run1N/AN/AN/AN/AN/AZephyr Way1833$439,6671,837 Sq.Ft.2/4/2025Zion St2N/AN/AN/AN/AN/A1129 Cherrytree LnChesapeake, VA 23320
Estimated Value $425,000
Living Area 1,606 SqFt
Beds 4
Baths 2
Year Built 1992
Property Type Single Family
Ownership Type Related
APN 0363007001370
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1125 Lady Ashley DrChesapeake, VA 23320
Estimated Value $402,000
Living Area 2,152 SqFt
Beds 3
Baths 2.5
Year Built 2000
Property Type Condominium
Ownership Type Multiple
APN 0363011000170
Neighborhood Rivercrest
School District Chesapeake City Public Schools
1709 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
1208 Earle AveChesapeake, VA 23324
Estimated Value $326,000
Living Area 1,118 SqFt
Beds 3
Baths 1.5
Year Built 1940
Property Type Single Family
Ownership Type Individual
APN 1590000001650
Neighborhood South Norfolk
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
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
4104 3rd StChesapeake, VA 23324
Estimated Value $396,000
Living Area 2,207 SqFt
Beds 5
Baths 3
Year Built 2010
Property Type Single Family
Ownership Type Individual
APN 1590000003330
Neighborhood South Norfolk
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
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
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
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
449 Cobblewood BndChesapeake, VA 23320
Estimated Value $233,000
Living Area 1,060 SqFt
Beds 3
Baths 1
Year Built 1986
Property Type Single Family
Ownership Type Individual
APN 0366007000100
Neighborhood Rivercrest
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
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
1205 Bramblewood CtChesapeake, VA 23323
Estimated Value $334,000
Living Area 425 SqFt
Beds 1
Baths 1
Year Built 1980
Property Type Single Family
Ownership Type Individual
APN 0343013000100
Neighborhood Deep Creek
School District Chesapeake City Public Schools
1813 Hazelwood RdChesapeake, VA 23323
Estimated Value $744,000
Living Area 3,531 SqFt
Beds 5
Baths 3.5
Year Built 2012
Property Type Single Family
Ownership Type Related
APN 0344002003360
Neighborhood Deep Creek
School District Chesapeake City Public Schools