95,763

Chesapeake County, VA Homes

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  • /50

    $449,500

    Under Contract
    • 3 Beds
    • 3.5 Baths
    • 2,140 Sq Ft

    433 Asuza St, Chesapeake, VA 23323

    Welcome to this stunning, like-new home in the highly sought-after Grassfield area of Chesapeake! Built in 2021, this beautifully maintained 3-bedroom, 3.5-bath home offers 2,140 sqft of thoughtfully designed living space filled with natural light. Step inside to charming hall tree built-ins, soaring cathedral ceilings, and an open-concept layout perfect for everyday living and entertaining. The

    Agent Photo

    Imani Overton-Santos

    Iron Valley Real Estate Prestige

    433 Asuza St, Chesapeake, VA 23323
  • /19

    $2,550

    Total Monthly Price

    • 3 Beds
    • 2.5 Baths
    • 1,788 Sq Ft
    • House for Rent

    1001 Shoal Creek Trail, Chesapeake, VA 23320

    FANTASTIC TOWN HOME LOCATED ON GREENBRIER GOLF COURSE IN CHESAPEAKE! KITCHEN HAS NEWER STAINLESS STEEL APPLIANCES, PANTRY AND BREAKFAST NOOK. MASTER BEDROOM W/ BATH, GOOD SIZED BEDROOMS ALL ON UPSTAIRS LEVEL. ATTACHED ONE CAR GARAGE. CLOSE TO SHOPPING & INTERSTATE.

    1001 Shoal Creek Trail, Chesapeake, VA 23320
  • 854 Jo Anne Cir, Chesapeake, VA 23322

    $560,000

    Sold Oct 20, 2025

    854 Jo Anne Cir, Chesapeake, VA 23322

    • 4 Beds
    • 3 Baths
    • 2,450 Sq Ft
    • Built 1980

    Last Sold Summary

    • $229/SF
    • 10 Days On Market

    Current Estimated Value $573,161

    Last Listing Agent Diane Pearman The Real Estate Group

    854 Jo Anne Cir, Chesapeake, VA 23322
    • 151 Hessian Loop, Chesapeake, VA 23322

      Not Listed For Sale

      151 Hessian Loop, Chesapeake, VA 23322

      • 6 Beds
      • 5 Baths
      • 3,874 Sq Ft
      • Built 2025
      151 Hessian Loop, Chesapeake, VA 23322

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Judy Duke Wainwright Real Estate

  • /19

    $514,000

    $29K PRICE INCREASE
    • 4 Beds
    • 2.5 Baths
    • 2,342 Sq Ft

    420 Brandon Way, Chesapeake, VA 23320

    BACK ON MARKET — another opportunity to make 420 Brandon Way yours! Located in desirable Clearfield Estates in the Greenbrier area of Chesapeake, this spacious 4-bedroom, 2.5-bath home offers approximately 2,342 sq ft, no HOA and Flood Zone X. The sellers have already completed significant updates and repairs, including a brand-new HVAC system, deck repairs, masonry repairs, an encapsulated

    Agent Photo

    Becky Lyons

    Coastal Real Estate & Auction Group LLC

    420 Brandon Way, Chesapeake, VA 23320
  • /19

    $3,300 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,415 Sq Ft
    • House for Rent

    303 Middleton Way, Chesapeake, VA 23322

    Bright like new Single Family condo in the Hickory School District ready to move into now. Space galore with three bedrooms, two and a half baths and great room open to kitchen. Great floor plan! Great kitchen for folks that love cooking. Kitchen includes a gas range and Granite countertops. All appliances included. Beautiful backyard patio, Neighborhood offers a playground, clubhouse w/fitness

    Shraddha Shah Small-Shah Residential RE Adv.

    303 Middleton Way, Chesapeake, VA 23322
  • 4309 Hillingdon Bend Unit 303, Chesapeake, VA 23321

    $218,000

    Sold Mar 12, 2026

    4309 Hillingdon Bend Unit 303, Chesapeake, VA 23321

    • 2 Beds
    • 2 Baths
    • 1,367 Sq Ft
    • Built 2017

    Last Sold Summary

    • 5% Below List Price
    • $159/SF
    • 18 Days On Market

    Current Estimated Value $218,401

    Last Listing Agent Judy Reed Judy Reed Realty

    4309 Hillingdon Bend Unit 303, Chesapeake, VA 23321
    • /2

      Not Listed For Sale

      1948 Bexley Ln, Chesapeake, VA 23322

      • 4 Beds
      • 3 Baths
      • 2,445 Sq Ft
      • Built 2025
      1948 Bexley Ln, Chesapeake, VA 23322

  • /46

    $599,900

    Open Sun 12PM - 3PM
    • 4 Beds
    • 2.5 Baths
    • 2,434 Sq Ft

    841 Woodstream Way, Chesapeake, VA 23322

    Beautifully maintained, thoughtfully updated, and a backyard you'll want to spend all of your time in! Step inside to a welcoming foyer filled with natural light and discover this inviting 4 bedroom, 2.5 bathroom home in a sought-after neighborhood within the Hickory School District. Updates include Brazilian hardwood, upgraded pet protect carpet padding, PEX plumbing, electrical, solar power,

    Agent Photo

    Robyn Slocum

    Iron Valley Real Estate HR

    841 Woodstream Way, Chesapeake, VA 23322
  • /13

    $1,150

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 700 Sq Ft
    • Condo for Rent

    4149-4151 2nd St Unit 41492ND-1, Chesapeake, VA 23324

    Remodeled 2BR 1BA duplex. Hardwood floors in LR, well laid out kitchen with washer and dryer hookups. Freshly painted throughout. Apartment has a lot of space and is very comfortable.Window AC & BB heat. All electric, no gas.

    4149-4151 2nd St Unit 41492ND-1, Chesapeake, VA 23324
  • 929 Thatcher Way, Chesapeake, VA 23320

    $458,000

    Sold Jun 15, 2026

    929 Thatcher Way, Chesapeake, VA 23320

    • 4 Beds
    • 2.5 Baths
    • 2,166 Sq Ft
    • Built 1992

    Last Sold Summary

    • 2% Above List Price
    • $211/SF
    • 11 Days On Market

    Current Estimated Value $459,103

    Last Listing Agent Jonathan Melvin Benham Real Estate LLC

    929 Thatcher Way, Chesapeake, VA 23320
    • /2

      Not Listed For Sale

      1950 Bexley Ln, Chesapeake, VA 23322

      • 4 Beds
      • 3 Baths
      • 2,518 Sq Ft
      • Built 2025
      1950 Bexley Ln, Chesapeake, VA 23322

  • /44

    $284,900

    $14K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,244 Sq Ft

    1346 River Birch Run S, Chesapeake, VA 23320

    Move in ready-well maintained Townhouse in desirable Greenbrier. LVT/Vinyl flooring throughout, carpet upstairs. Open floor plan with Large Livingroom, Kitchen, and Dining Area. Fenced in back yard and storage shed. Do not miss this move in ready home.

    Agent Photo

    Eric Hovik

    RE/MAX Alliance

    1346 River Birch Run S, Chesapeake, VA 23320
  • /46

    $3,500 Per Month

    • 4 Beds
    • 2.5 Baths
    • 1,932 Sq Ft
    • House for Rent

    1901 Kelly Run, Chesapeake, VA 23320

    All kitchen appliances stay, bring your own washer and dryer. Carpets will be professionally cleaned prior to move-in. Fireplace and dryer vent have been professionally cleaned and inspected August 2026. Huge fenced yard overlooking the water. Reverse osmosis and re-mineralizer on kitchen faucet. 4 bedrooms are great size, one is smaller but adequate. Great closet space throughout. Owners are

    Tina Bradley Flexible Real Estate

    1901 Kelly Run, Chesapeake, VA 23320
  • 2014 Millville Rd, Chesapeake, VA 23323

    $745,000

    Sold Apr 24, 2026

    2014 Millville Rd, Chesapeake, VA 23323

    • 5 Beds
    • 4 Baths
    • 2,700 Sq Ft
    • Built 2023

    Last Sold Summary

    • $276/SF
    • 179 Days On Market

    Last Listing Agent David Drogus G Daniels & Company

    2014 Millville Rd, Chesapeake, VA 23323
    • /2

      Est $330,061

      Not Listed For Sale

      921 Taft Rd, Chesapeake, VA 23322

      • Studio
      921 Taft Rd, Chesapeake, VA 23322

  • /32

    $265,000

    Under Contract
    • 3 Beds
    • 1.5 Baths
    • 1,092 Sq Ft

    638 Milby Dr, Chesapeake, VA 23325

    Make this your first stop! This well-maintained 3-bedroom, 1.5-bath ranch in Norfolk Highlands offers the convenience of single-level living and the peace of mind that comes with major recent updates. The kitchen was remodeled in 2024, both bathrooms were remodeled in 2025, the HVAC system was replaced in 2024, and the gutters were upgraded in 2025. Pride of ownership is evident throughout,

    Agent Photo

    Matthew Salway

    Iron Valley Real Estate HR

    638 Milby Dr, Chesapeake, VA 23325
  • /11

    $3,300

    Total Monthly Price

    • 3 Beds
    • 2.5 Baths
    • 2,415 Sq Ft
    • House for Rent

    303 Middleton Way, Chesapeake, VA 23322

    Bright like new Single Family condo in the Hickory School District ready to move into now. Space galore with three bedrooms, two and a half baths and great room open to kitchen. Great floor plan! Great kitchen for folks that love cooking. Kitchen includes a gas range and Granite countertops. All appliances included. Beautiful backyard patio, Neighborhood offers a playground, clubhouse w/fitness

    303 Middleton Way, Chesapeake, VA 23322
  • 1444 Culpepper Ave, Chesapeake, VA 23323

    $364,000

    Sold Nov 12, 2025

    1444 Culpepper Ave, Chesapeake, VA 23323

    • 3 Beds
    • 2 Baths
    • 1,360 Sq Ft
    • Built 1978

    Last Sold Summary

    • $268/SF
    • 108 Days On Market

    Current Estimated Value $362,482

    Last Listing Agent Jay Kotchka BHHS RW Towne Realty

    1444 Culpepper Ave, Chesapeake, VA 23323
    • /26

      Est $535,733

      Not Listed For Sale

      3354 Patrick Henry Dr, Chesapeake, VA 23323

      • 3 Beds
      • 2.5 Baths
      • 2,200 Sq Ft
      • Built 2017
      3354 Patrick Henry Dr, Chesapeake, VA 23323

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Sidney James HHHunt Realty Inc

  • /24

    $220,000

    • 2 Beds
    • 1 Bath
    • 825 Sq Ft

    901 Stewart St, Chesapeake, VA 23324

    Welcome to 901 Stewart Street! This charming 2-bedroom, 1-bath ranch offers comfortable single-level living in the South Norfolk area of Chesapeake. With approximately 825 square feet, the home features a functional layout with plenty of opportunity to make the space your own. Enjoy a spacious yard with room for outdoor entertaining, gardening, or creating your own outdoor retreat. Conveniently

    Agent Photo

    Leslie Brennan

    Aweigh Real Estate

    901 Stewart St, Chesapeake, VA 23324
  • /12

    $1,995 Per Month

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • House for Rent

    2436 Shillelagh Rd, Chesapeake, VA 23323

    ADORABLE 3 BEDROOM 2 BATH SINGLE FAMILY HOME ON HUGE LOT IN SHILLELAGH FARMS. HOME FEATURES OPEN SPACIOUS KITCHEN, WITH ALL APPLIANCES, ATTACHED GARAGE W/FULL SIZE WASHER, DRYER, HOME HAS BEEN FRESHLY PIAINTED, NEW LVP FLOORING, AND CARPET. AGAIN, THIS HOME IS ON A HUGE LOT AND TENANTS ARE RESPONSIBILE FOR THE LAWN MAINTENANCE. THERE IS ALSO A GARDEN IN THE VERY BACK OF THE PROPERTY THAT THE

    Tina Simmons The Real Estate Group

    2436 Shillelagh Rd, Chesapeake, VA 23323
  • 805 Calvert Ct, Chesapeake, VA 23320

    $399,000

    Sold Dec 11, 2025

    805 Calvert Ct, Chesapeake, VA 23320

    • 3 Beds
    • 2.5 Baths
    • 2,225 Sq Ft
    • Built 2004

    Last Sold Summary

    • $179/SF
    • 41 Days On Market

    Current Estimated Value $413,251

    Last Listing Agent Taylor Lennox Keller Williams Town Center

    805 Calvert Ct, Chesapeake, VA 23320
    • /2

      Est $593,134

      Not Listed For Sale

      3316 Conservancy Dr, Chesapeake, VA 23323

      • 4 Beds
      • 4 Baths
      • 2,600 Sq Ft
      • Built 2017
      3316 Conservancy Dr, Chesapeake, VA 23323

  • /46

    $619,000

    Open Sat 12PM - 2PM
    • 4 Beds
    • 2.5 Baths
    • 3,086 Sq Ft

    228 Country Club Blvd, Chesapeake, VA 23322

    Fantastic location close to shopping, major hwys primary and secondary schools and so much more! The already large/oversized primary suite has a large additional private flex room for office or nursery, workout room or whatever your heart desires. Complete with private bath and large walk in closet. For additional privacy the ancillary bedrooms are on the opposite side of the home. This home is a

    Agent Photo

    Janice Myers-Hollowell

    World Class Realty

    228 Country Club Blvd, Chesapeake, VA 23322
  • /40

    $3,075

    Total Monthly Price

    • 4 Beds
    • 2.5 Baths
    • 2,400 Sq Ft
    • House for Rent

    910 Cantor St, Chesapeake, VA 23322

    Better than NEW! Situated on a massive fenced lot on a quiet cul-de-sac in sought-after Stonegate! A pet-friendly 4-bedroom, 2 1/2 bath home with attached garage and 2,400 square feet of well-appointed living space available now*!!.This fully-updated home features open airy rooms with tall ceilings and lots of fabulous natural light and a combination of custom purple heart and cherry wood

    910 Cantor St, Chesapeake, VA 23322
  • 776 Big Bear Ln, Chesapeake, VA 23323

    $580,000

    Sold Sep 01, 2026

    776 Big Bear Ln, Chesapeake, VA 23323

    • 4 Beds
    • 2.5 Baths
    • 2,780 Sq Ft
    • Built 2022

    Last Sold Summary

    • 2% Below List Price
    • $209/SF
    • 55 Days On Market

    Current Estimated Value $592,835

    Last Listing Agent Maritza Brandon The Real Estate Group

    776 Big Bear Ln, Chesapeake, VA 23323
    • /16

      Est $296,211

      Not Listed For Sale

      356 Holyoke Ln, Chesapeake, VA 23320

      • 2 Beds
      • 2.5 Baths
      • 1,352 Sq Ft
      • Built 2011
      356 Holyoke Ln, Chesapeake, VA 23320

      Last Sold Summary

      • 36 Days On Market

      Last Listing Agent Susan Jenkins Better Homes and Gardens Native American Group

  • /49

    $630,000

    Under Contract
    • 5 Beds
    • 3 Baths
    • 3,000 Sq Ft

    404 Clara Dr, Chesapeake, VA 23320

    BUY THIS AWESOME HOME, WE'LL BUY YOURS!* Welcome to 404 Clara Drive, where space, comfort, and style come together! Tucked away on a quiet cul-de-sac, this beautifully maintained home features 5 spacious bedrooms and 3 full bathrooms, providing plenty of room for everyone. Step inside to a dramatic two-story foyer that opens to formal living and dining rooms for entertaining. The eat-in kitchen

    Agent Photo

    Kelvin Reed

    Reeds Real Estate LLC

    404 Clara Dr, Chesapeake, VA 23320
  • /2

    $1,900 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,352 Sq Ft
    • Condo for Rent

    347 Holyoke Ln, Chesapeake, VA 23320

    Welcome home to this beautiful Town-home-style condo, featuring two spacious master suites, each with its own walk-in closet and private full bathroom. The open-concept main level offers a comfortable living room, dining area, and galley-style kitchen with pantry and stainless steel appliances. The home also features a lovely private patio with an outdoor storage shed, perfect for relaxing or

    Delwyn Cosby RE/MAX Alliance

    347 Holyoke Ln, Chesapeake, VA 23320
  • 4141 Belvedere Dr, Chesapeake, VA 23321

    $685,000

    Sold Jun 01, 2026

    4141 Belvedere Dr, Chesapeake, VA 23321

    • 4 Beds
    • 3 Baths
    • 3,825 Sq Ft
    • Built 1971

    Last Sold Summary

    • $179/SF
    • 17 Days On Market

    Current Estimated Value $684,511

    Last Listing Agent Kathy Worthen BHHS RW Towne Realty

    4141 Belvedere Dr, Chesapeake, VA 23321
    • /2

      Est $271,371

      Not Listed For Sale

      1614 Higgins Ave, Chesapeake, VA 23324

      • 3 Beds
      • 3 Baths
      • 1,528 Sq Ft
      • Built 2010
      1614 Higgins Ave, Chesapeake, VA 23324

  • /44

    $624,900

    • 4 Beds
    • 2.5 Baths
    • 2,772 Sq Ft

    316 Janes Way, Chesapeake, VA 23320

    Welcome home to this spacious, beautiful 4-bedroom, 2.5-bath home in sought-after Peyton Estates, offering nearly 2,800 square feet of comfortable living space on a generously sized lot. Inside, you’ll find plenty of room to spread out, including inviting living spaces and a cozy fireplace. A whole-house water filtration system adds an extra level of everyday comfort and convenience. The attached

    Agent Photo

    Stacy Potts

    Focus Realty LLC

    316 Janes Way, Chesapeake, VA 23320
  • /7

    $3,200

    Total Monthly Price

    • 4 Beds
    • 3 Baths
    • 2,600 Sq Ft
    • House for Rent

    137 Hurdle Dr, Chesapeake, VA 23322

    This spacious 2,600 sq. ft. home offers a perfect blend of comfort and style, featuring four generously sized bedrooms and three well-appointed bathrooms. As you step inside, you'll be greeted by an inviting open floor plan that seamlessly connects the living, dining, and kitchen areas, ideal for entertaining or simply relaxing. The modern kitchen boasts sleek countertops, ample

    137 Hurdle Dr, Chesapeake, VA 23322
  • 240 Hurdle Dr, Chesapeake, VA 23322

    $565,000

    Sold Aug 26, 2026

    240 Hurdle Dr, Chesapeake, VA 23322

    • 4 Beds
    • 2.5 Baths
    • 2,200 Sq Ft
    • Built 2021

    Last Sold Summary

    • 2% Below List Price
    • $257/SF
    • 34 Days On Market

    Current Estimated Value $571,274

    Last Listing Agent Carol Hall BHHS RW Towne Realty

    240 Hurdle Dr, Chesapeake, VA 23322
    • /45

      Not Listed For Sale

      1310 Sparrow Rd, Chesapeake, VA 23325

      • 2 Beds
      • 1.5 Baths
      • 1,050 Sq Ft
      • Built 1974
      1310 Sparrow Rd, Chesapeake, VA 23325

  • /7

    $750,000

    • Land
    • 41,817 Sq Ft
    • $781,250 per Acre

    1148 Sunlight Dr, Chesapeake, VA 23322

    AMAZING OPPORTUNITY TO BUILD NEW CONSTRUCTION HOMES IN A PEACEFUL SETTING, YET CONVENIENTLY LOCATED AND CLOSE TO SHOPPING, SCHOOLS AND INTERSTATE. TO BE SOLD TOGETHER WITH 1136 SUNLIGHT DR, THIS ALLOWS FOR 3 BUILDABLE LOTS AT 0.64 AC EACH. ALL THE WORK IS DONE, YOU JUST NEED TO BUILD!

    Agent Photo

    Tyler Broker/Owner

    Prodigy Realty

    1148 Sunlight Dr, Chesapeake, VA 23322
  • /15

    $3,500 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,430 Sq Ft
    • House for Rent

    756 Yorkshire Trail, Chesapeake, VA 23322

    Home Occupied but Easy to show. Fully renovated Kitchen and Brand new Primary Bathroom and Full Bathroom.Home Ready for Lease 11/01/2026. Spacious 4 BR 2.5 BTH Granite counter tops, corner lot & Deck with Vinyl fencing. Clubhouse & Pool access with HOA approval. $150 monthly HOA FEE Due with rent. Landlord requires Rental Insurance.

    Teneka Boone Fit Realty

    756 Yorkshire Trail, Chesapeake, VA 23322
  • 516 Whistle Town Rd, Chesapeake, VA 23322

    $595,000

    Sold May 20, 2026

    516 Whistle Town Rd, Chesapeake, VA 23322

    • 4 Beds
    • 2.5 Baths
    • 2,191 Sq Ft
    • Built 1994

    Last Sold Summary

    • 3% Above List Price
    • $272/SF
    • 20 Days On Market

    Current Estimated Value $582,615

    Last Listing Agent Catherine Gorman Howard Hanna Real Estate Svcs.

    516 Whistle Town Rd, Chesapeake, VA 23322
    • /43

      Est $314,923

      Not Listed For Sale

      114 Alice St, Chesapeake, VA 23323

      • 3 Beds
      • 2.5 Baths
      • 1,416 Sq Ft
      • Built 2009
      114 Alice St, Chesapeake, VA 23323

      Last Sold Summary

      • 57 Days On Market

      Last Listing Agent William J. Barnes Gracious Living Realty, Inc.

Showing Results 321 - 360, Page 9 of 18

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