Chesapeake Homes for Sale
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. The city is known for lower property taxes and larger lot sizes compared to neighboring Virginia Beach and Norfolk, which makes it especially attractive to families looking for more space.
93 homes for sale in Chesapeake right now.
Under Contract$3,537,900
Lots Moses Grandy ( Par.B,C,D) Trail, Chesapeake VA 23323
Chesapeake, Virginia 23323
$1,700,000
10+AC Yadkin Property I-64 Express Way Road, Chesapeake VA 23323
Chesapeake, Virginia 23323
Under Contract$1,200,000
1512 Gray Rock RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$1,195,000
536 Thistley LN, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$999,900
MM Carley (THE GRASSFIELD) CT, 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
$959,900
1137 Kingsbury DR, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$899,900
MM Carley (THE BALLAHACK) CT, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$875,000
3341 Country Mill RN, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$859,900
MM Carley (The Albemarle) CT, 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
$840,000
436 Stoney Mist WAY, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$825,000
309 Sweetbay DR, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$759,990
312 Maycox Lane NONE, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$759,900
3710 Carley CT, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$750,000
7.4 AC Moses Grandy TRL, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$750,000
1942 Bexley LN, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$725,000
2128 Shipyard RD, CHESAPEAKE VA 23323
Chesapeake, Virginia 23323
$720,000
1125 Sutherlyn CT, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$700,000
1920 Crayton WAY, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$699,700
1904 McCoy Rd NONE, CHESAPEAKE VA 23323
Chesapeake, Virginia 23323
$699,000
3932 Colony Pointe DR, CHESAPEAKE VA 23321
Chesapeake, Virginia 23321
$695,900
1906 McCoy Rd NONE, CHESAPEAKE VA 23323
Chesapeake, Virginia 23323
$694,990
MM Intracoastal(The Hadley ) WAY, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$640,000
712 Country Club BLVD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$610,900
MM Legacy (Augusta Cottage 2700 Sf) NONE, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$609,900
MM Myrtle II NONE, CHESAPEAKE VA 23321
Chesapeake, Virginia 23321
Under Contract$599,900
3320 Daystone ARCH, CHESAPEAKE VA 23323
Chesapeake, Virginia 23323
$595,900
MM Legacy (Augusta Cottage 2500 Sf) NONE, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$569,900
1121 Kinderly LN, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$565,900
122 Lenas Way NONE, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$565,000
2256 Shipyard RD, CHESAPEAKE VA 23323
Chesapeake, Virginia 23323
$559,900
909 Douglas Eley LN, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$550,000
1837 Honey Milk RD, CHESAPEAKE VA 23323
Chesapeake, Virginia 23323
Under Contract$549,900
1815 Honey Milk RD, CHESAPEAKE VA 23323
Chesapeake, Virginia 23323
$545,900
5025 Duxbury RD, CHESAPEAKE VA 23321
Chesapeake, Virginia 23321
$545,000
3245 Conservancy DR, CHESAPEAKE VA 23323
Chesapeake, Virginia 23323
$539,900
449 Sawyers Mill XING, CHESAPEAKE VA 23323
Chesapeake, Virginia 23323
$539,900
MM Myrtle NONE, CHESAPEAKE VA 23321
Chesapeake, Virginia 23321
$537,900
124 Lenas Way NONE, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$535,900
126 Lenas Way NONE, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$529,900
MM Bayberry , Chesapeake VA 23321
Chesapeake, Virginia 23321
$529,000
730 Beckley LN, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$525,900
128 Lenas Way NONE, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$509,900
1601 Mary Lou LN, CHESAPEAKE VA 23323
Chesapeake, Virginia 23323
Under Contract$499,900
821 STACEY PL, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$498,575
4719 Mahogany RN, CHESAPEAKE VA 23321
Chesapeake, Virginia 23321
$489,500
4743 Mahogany RN, CHESAPEAKE VA 23321
Chesapeake, Virginia 23321
$465,000
1803 Honey Milk RD, CHESAPEAKE VA 23323
Chesapeake, Virginia 23323
$454,900
4725 Mahogany RN, CHESAPEAKE VA 23321
Chesapeake, Virginia 23321
Under Contract$450,000
2224 Lloyd DR, CHESAPEAKE VA 23325
Chesapeake, Virginia 23325
$448,000
1715 Ark Royal RD, CHESAPEAKE VA 23323
Chesapeake, Virginia 23323
$439,900
Lot D Buskey RD, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
$428,000
1216 Destiny WAY, CHESAPEAKE VA 23320
Chesapeake, Virginia 23320
$424,999
708 Colony DR, CHESAPEAKE VA 23322
Chesapeake, Virginia 23322
Under Contract$419,900
2220 Battery Park Rd NONE, CHESAPEAKE VA 23323
Chesapeake, Virginia 23323
$400,000
1011 Holly AVE, CHESAPEAKE VA 23324
Chesapeake, Virginia 23324
Under Contract$400,000
3340 Country CIR, CHESAPEAKE VA 23324
Chesapeake, Virginia 23324
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.
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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.