Homes for Sale in Hampton Roads
Chesapeake is Virginia's second-largest city by area and offers a mix of suburban subdivisions, rural acreage, and waterfront properties along the Intracoastal Waterway. Western Branch, Greenbrier, and Great Bridge are among the most sought-after neighborhoods, with top-rated public schools and easy access to I-64 and the Chesapeake Expressway. Chesapeake is known for its lower property taxes and larger lot sizes compared to neighboring cities, making it attractive to families looking for more space. Newer construction is common in areas like Edinburgh and Cahoon Plantation, while established neighborhoods like Hickory and Indian River offer more mature settings. The VaHome team has deep experience guiding buyers through Chesapeake's varied submarkets.
View Chesapeake's dedicated homes-for-sale page — neighborhoods, market notes, FAQs and more →
$399,999
3861 Ahoy DR, CHESAPEAKE VA 23321
Chesapeake, Virginia 23321
Under Contract$399,900
Lot C Buskey RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$389,900
2418 Fieldsway DR, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$386,500
1233 Parkley DR, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$365,000
708 Tiffany Green CT, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$358,900
2712 Fenway AVE, CHESAPEAKE VA 23323
Chesapeake, Virginia 23323
$335,000
602 Lacy Oak DR, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
Under Contract$334,000
1301 Tuckaway RCH #D, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$325,000
820 Henry AVE, CHESAPEAKE VA 23323
Chesapeake, Virginia 23323
$320,000
4376 Pickney LN, CHESAPEAKE VA 23324
Chesapeake, Virginia 23324
$320,000
1440 Rollesby WAY, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$310,500
585 Marc Smiley RD, CHESAPEAKE VA 23324
Chesapeake, Virginia 23324
Under Contract$309,000
2644 Leytonstone DR, CHESAPEAKE VA 23321
Chesapeake, Virginia 23321
Under Contract$305,000
2664 Leytonstone Drive NONE, CHESAPEAKE VA 23321
Chesapeake, Virginia 23321
Under Contract$294,999
2703 Cayce DR, CHESAPEAKE VA 23324
Chesapeake, Virginia 23324
$265,000
915 Mckinley AVE, CHESAPEAKE VA 23324
Chesapeake, Virginia 23324
$230,000
2424 Chancery LN #105, CHESAPEAKE VA 23321
Chesapeake, Virginia 23321
$229,500
2469 Leytonstone DR #106, CHESAPEAKE VA 23321
Chesapeake, Virginia 23321
$200,000
1317 Yeadon RD, CHESAPEAKE VA 23324
Chesapeake, Virginia 23324
$185,000
1405 Perry ST, CHESAPEAKE VA 23324
Chesapeake, Virginia 23324
$179,900
4061 Holly Cove DR, CHESAPEAKE VA 23321
Chesapeake, Virginia 23321
Under Contract$150,000
4440 S Military HWY, CHESAPEAKE VA 23321
Chesapeake, Virginia 23321
$4,850
1137 Kingsbury DR, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$4,200
312 Maycox LN, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$3,200
1248 Madeline Ryan WAY, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$2,600
606 Muddy Creek RD, CHESAPEAKE VA 23324
Chesapeake, Virginia 23324
$2,400
511 Marc Smiley RD, CHESAPEAKE VA 23324
Chesapeake, Virginia 23324
$2,300
7 Mosely CIR, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$2,200
2206 Berkley AVE, CHESAPEAKE VA 23324
Chesapeake, Virginia 23324
$2,175
20 Corby CIR, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$2,145
701 Nottaway DR, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$1,995
4516 S Military HWY, CHESAPEAKE VA 23321
Chesapeake, Virginia 23321
$1,350
1201 Transylvania AVE, CHESAPEAKE VA 23324
Chesapeake, Virginia 23324
About the Hampton Roads Real Estate Market
Hampton Roads is one of the most dynamic real estate markets on the East Coast, anchored by the largest naval complex in the world at Naval Station Norfolk and home to roughly 120,000 active-duty, reserve, and civilian Department of Defense personnel. The region spans seven cities — Virginia Beach, Norfolk, Chesapeake, Suffolk, Portsmouth, Hampton, and Newport News — plus the Peninsula communities of Williamsburg, Yorktown, and Poquoson, with each market carrying its own personality, school district, and price profile.
Buying or selling here means thinking about more than just a house. Tidewater geography means flood zones, hurricane preparation, and waterfront premiums matter. Military presence means BAH affordability, PCS season inventory crunches (May through August), and VA loan eligibility are top of mind for a meaningful share of every neighborhood. School quality varies block by block, especially across the seven independent city school divisions, and is often the deciding factor for relocating families.
Why Buyers and Sellers Choose VaHome
The VaHome Team — Tom and Dariya Milan with LPT Realty — focuses on the Hampton Roads region with deep expertise in military relocation, VA financing, and the trade-offs that local buyers actually face. From listing strategy that gets your home in front of the right relocating buyer to buyer representation that respects your BAH cap and PCS timeline, the team treats every transaction as a long-term relationship. The site is built to make decisions clearer: BAH-aware search, drive-time mapping to every major installation, neighborhood guides written by people who live here, and a calculator that shows real monthly cost — taxes, insurance, HOA, and PMI included — instead of a teaser headline number.
Plan Your Next Move
Whether you are buying your first home with a VA loan, moving up while your kids transition between school districts, or selling a Hampton Roads property to relocate to your next duty station, the resources on this site are organized around the questions you are actually asking. Browse listings filtered by base proximity, paygrade-aware BAH cap, and commute time. Read neighborhood guides for Virginia Beach, Norfolk, Chesapeake, Suffolk, Hampton, Newport News, Williamsburg, and the Peninsula communities. Use the mortgage calculator to compare conventional, FHA, VA, USDA, and jumbo loan scenarios side by side. When you are ready to talk, the contact form goes directly to a specialist who knows the area, the lenders, and the timing.