Chesapeake Homes for Sale
Homes for sale in Chesapeake, VA appeal to buyers who want suburban space, top-rated schools, and easy access to Virginia Beach and Norfolk. The city's geography splits roughly into five corridors: Greenbrier (23320) with newer construction and shopping near the mall; Great Bridge (23320, 23322) with the historic Battlefield district and excellent schools; Hickory (23322) with large-lot family homes and Hickory High; Western Branch (23321) near the Portsmouth border with mature trees and starter homes; and Deep Creek / South Norfolk (23323, 23324) with affordable inventory and waterfront access. Buyer demand is anchored by Chesapeake Public Schools — among the highest-rated in Hampton Roads — including Hickory High, Grassfield High, Great Bridge High, and Western Branch High. Median home prices range from $300K starter homes in Deep Creek to $600K+ Great Bridge family homes and $1M+ luxury estates in Hickory's gated communities. Chesapeake's commute is excellent for buyers working in Virginia Beach, Norfolk Naval Shipyard, or Newport News Shipbuilding via the I-664 and I-64 corridors. Below you'll find every active Chesapeake MLS listing pulled hourly from the REIN feed.
628 homes for sale in Chesapeake right now.(+544 under contract)
$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
$2,990,000
4112 Mingo TRL, CHESAPEAKE VA 23325
Chesapeake, Virginia 23325
$2,500,000
7.88ac Peaceful Road, Chesapeake VA 23322
Chesapeake, Virginia 23322
$2,425,000
25+AC S Military HWY, CHESAPEAKE VA 23321
Chesapeake, Virginia 23321
Under Contract$2,298,777
1601 Water View CIR, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$2,000,000
168 AC St Brides RD W, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$1,800,000
86.15A Taft Road, Chesapeake VA 23322
Chesapeake, Virginia 23322
New Listing$1,750,000
1436 Paul Eason DR, 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
Under Contract$1,600,000
135ac St. Brides Road, Chesapeake VA 23322
Chesapeake, Virginia 23322
$1,599,000
641 Ravenwoods DR, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$1,325,000
1149 Waters RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$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
$1,295,000
516 Peaceful RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$1,279,900
1501 Sanderson 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$1,257,023
704 Washington DR, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$1,250,000
4443 Old Battlefield BLVD S, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
Under Contract$1,250,000
1317 Baffy LOOP, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$1,250,000
1301 Simon DR, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
Under Contract$1,200,000
1512 Gray Rock RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$1,200,000
313 Scone Castle LOOP, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$1,195,795
4030 Tucker LN, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$1,175,000
521 Thistley LN, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$1,149,000
536 Thistley LN, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$1,100,000
304 Jule DR, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$1,100,000
2325 Woodhurst LN, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$1,099,000
187 Hessian LOOP, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$1,089,000
2624 Ballahack RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$1,070,872
1425 TAFT RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
New Listing$1,049,900
1904 Ballahack RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$1,025,000
238 Hessian LOOP, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$999,900
MM Carley (THE GRASSFIELD) CT, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$999,000
1923 Hungarian RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$995,260
1560 Sanderson RD, 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
$959,900
1137 Kingsbury DR, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$958,999
2417 Baum RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
New Listing$950,000
4249 Taylor RD, CHESAPEAKE VA 23321
Chesapeake, Virginia 23321
$950,000
3600 Fluridy RD, 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
$945,170
733 Beaver Dam RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$938,197
1432 Taft RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$929,223
2868 Raccoon TRL, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
New Listing$928,000
2408 Johnstown RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$927,510
1258 Solitude Trl, Chesapeake, VA 23322, USA
Chesapeake, Virginia 23322
$916,038
741 Beaver Dam RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Refine by price, bedrooms, square footage, and more on the full search page.
Neighborhoods to know in Chesapeake
Chesapeake's neighborhoods divide roughly into north-of-the-canal (more developed, closer to I-64 and Norfolk) and south-of-the-canal (more rural and waterfront). Greenbrier and Edinburgh are popular newer subdivisions with strong school zones. Great Bridge has small-town feel with historic charm and good schools. Western Branch offers established single-family neighborhoods convenient to Portsmouth and the shipyard. Cahoon Plantation is a planned golf-course community. South Norfolk is the city's older, walkable urban district. For waterfront buyers, neighborhoods along the Intracoastal Waterway and the Elizabeth River branches offer dock-out access; deep-water neighborhoods are particularly popular with boating families.
Chesapeake market snapshot
Chesapeake's median home prices are typically in the middle of the regional range, but lot sizes are larger and property taxes lower than most neighboring cities — so the dollar-per-square-foot or dollar-per-acre value is often better than Virginia Beach or Norfolk. Newer construction is common in northern Chesapeake (Edinburgh, Cahoon, Bells Mill area), while established neighborhoods like Hickory and Indian River offer more mature settings. Buyers shopping Chesapeake often weigh it against Suffolk for more land and lower price-per-square-foot.
Common questions about Chesapeake real estate
Where can I find Chesapeake homes for sale right now?
The listings grid above shows current Chesapeake inventory from the REIN MLS, refreshed continuously. Click into any listing for full details. Use /listings/?city=Chesapeake to refine by price, bedrooms, or property type.
What is real estate like in Chesapeake, VA?
Chesapeake real estate is suburban-leaning, with newer subdivisions in northern areas, established single-family neighborhoods in the middle, and rural/waterfront acreage in the south. Property taxes are among the most favorable in the region, and lot sizes tend to be larger than in Virginia Beach or Norfolk — making Chesapeake a popular choice for families wanting more space without leaving the metro area.
Are houses for sale in Chesapeake good for families?
Chesapeake Public Schools are consistently among the highest-rated in Hampton Roads, and the city has invested heavily in parks, libraries, and recreation centers. Greenbrier, Western Branch, and Great Bridge are particularly popular family neighborhoods. A VaHome agent can help you align school zone preferences with current inventory.
Does Chesapeake have waterfront homes?
Yes — Chesapeake has substantial waterfront inventory along the Intracoastal Waterway, the Elizabeth River branches, and assorted creeks. Dock-out and deep-water properties trade at premium prices and are popular with boating buyers. Use the search to filter for waterfront-adjacent neighborhoods.
Neighborhoods in Chesapeake
Browse Chesapeake homes by neighborhood — every neighborhood page shows live REIN MLS listings filtered to that area.
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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.