Homes for Sale in Chesapeake
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 →
$5,625,000
824 Post AVE, CHESAPEAKE VA 23324
Chesapeake, Virginia 23324
$4,000,000
4653 Battlefield BLVD, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
Under Contract$3,537,900
Lots Moses Grandy ( Par.B,C,D) Trail, Chesapeake VA 23323
Chesapeake, Virginia 23323
$2,500,000
7.88ac Peaceful Road, Chesapeake VA 23322
Chesapeake, Virginia 23322
$2,000,000
168 AC St Brides RD W, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$1,704,000
556 B Gallbush RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$1,700,000
10+AC Yadkin Property I-64 Express Way Road, Chesapeake VA 23323
Chesapeake, Virginia 23323
$1,599,000
641 Ravenwoods DR, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$1,395,000
1149 Waters RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$1,300,000
1301 Simon DR, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$1,300,000
521 Woodards Ford RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$1,299,000
2700 Ballahack RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$1,278,786
1533 Cedarville CT, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$1,275,000
413 Centerville Turnpike N, Chesapeake VA 23320
Chesapeake, Virginia 23320
$1,257,400
2832 Martins Point WAY, CHESAPEAKE VA 23321
Chesapeake, Virginia 23321
Under Contract$1,250,000
1317 Baffy LOOP, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$1,250,000
4443 Old Battlefield BLVD S, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
Under Contract$1,200,000
313 Scone Castle LOOP, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$1,195,000
536 Thistley LN, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$1,100,000
2325 Woodhurst LN, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$1,089,000
2624 Ballahack RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$999,900
MM Carley (THE GRASSFIELD) CT, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$990,000
304 Mistral PL, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$985,769
1429 Taft RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$982,800
1928 Moses Grandy Trail, Chesapeake VA 23323
Chesapeake, Virginia 23323
$978,602
1361 Jury RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$975,000
212 Carmichael WAY, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$969,900
1149 Beaver Dam RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$959,999
2417 Baum RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$959,900
1137 Kingsbury DR, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$950,000
1421 Saint Brides RD W, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$949,000
3016 Cedarville Road, Chesapeake VA 23322
Chesapeake, Virginia 23322
$949,000
3016 Cedarville Road, Chesapeake VA 23322
Chesapeake, Virginia 23322
Under Contract$938,197
1432 Taft RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$925,000
2412 Benefit RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$900,000
920 Beaver Dam RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$899,900
MM Carley (THE BALLAHACK) CT, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$899,900
501 Shadow Brooke DR, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$899,900
1301 Sanderson RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$898,000
1024 Pleasant Ridge DR, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$894,525
208 Kwanzan CT, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$885,000
604 Stoneleigh CT, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$883,500
MM Sanderson (Ambler Parcel 11 Homesite 5 ) RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$880,265
1440 TAFT RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$877,500
2116 Sanderson RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$874,900
1124 Saint Brides RD W, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$866,900
MM Racoon (Kentland Parcel 21 Homesite 2 ) TRL, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$859,900
MM Carley (The Albemarle) CT, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$851,282
1525 Cedarville CT, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$850,000
4901 Ballahack RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$850,000
3315 Tyre Neck RD, CHESAPEAKE VA 23321
Chesapeake, Virginia 23321
$849,900
3722 Carley CT, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$846,900
1924 Hungarian RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$840,000
4500 Backwoods RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$840,000
436 Stoney Mist WAY, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$838,740
1220 Kidbrooke ST, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$838,152
1490 Cedarville CT, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$837,740
1248 Kidbrooke ST, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$837,740
1256 Kidbrooke ST, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$825,000
423 Battlefield Boulevard N, Chesapeake VA 23320
Chesapeake, Virginia 23320
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.