95,765

Chesapeake County, VA Homes

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  • /40

    $579,000

    $6K PRICE DROP Pending
    • 4 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    1045 Winchester Way, Chesapeake, VA 23320

    Beautifully updated and impeccably maintained, this exceptional 4BR/2.5BA home offers thoughtfully designed living space in the highly sought-after Kemp Woods neighborhood of Chesapeake. Nestled on a quiet, tree-lined street, this move-in ready home perfectly blends timeless elegance, quality craftsmanship, & modern updates. Step inside to an inviting floor plan filled with natural light, with

    Agent Photo

    Val Milan

    Own Real Estate LLC

    1045 Winchester Way, Chesapeake, VA 23320
  • /47

    $3,400 Per Month

    • 3 Beds
    • 3.5 Baths
    • 2,100 Sq Ft
    • Condo for Rent

    900 Billy Obrien Ln, Chesapeake, VA 23322

    Experience luxury living in Legacy, a beautifully designed townhome community in the heart of Historic Great Bridge. This spacious residence features three bedrooms, each with its own private ensuite bathroom, sophisticated mid-century coastal finishes, 10-foot ceilings on the main level, and extensive hardwood flooring. The stunning custom kitchen offers a 10-foot shiplap island, custom range

    Agent Photo

    Andy Nelson

    Iron Valley Real Estate HR

    900 Billy Obrien Ln, Chesapeake, VA 23322
  • 1715 Woodmill St, Chesapeake, VA 23320

    $400,000

    Sold Sep 18, 2026

    1715 Woodmill St, Chesapeake, VA 23320

    • 3 Beds
    • 2.5 Baths
    • 1,800 Sq Ft
    • Built 2002

    Last Sold Summary

    • $222/SF
    • 18 Days On Market

    Current Estimated Value $398,322

    Last Listing Agent Debbie Childs RE/MAX Elevate

    1715 Woodmill St, Chesapeake, VA 23320
    • /5

      Not Listed For Sale

      707 Arthurs Ct, Chesapeake, VA 23322

      707 Arthurs Ct, Chesapeake, VA 23322

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Joel Hinckley PlatLabs, LLC

  • /22

    $327,000

    • 4 Beds
    • 1 Bath
    • 1,264 Sq Ft

    1505 Sparrow Rd, Chesapeake, VA 23325

    Corner-lot 3–4 bedroom home on 0.25 acres featuring a horseshoe driveway plus a paved drive leading to an oversized detached garage. Flexible bonus room; office, playroom, or guest space. Recent updates include newer windows, 2025 roof, 2024 flooring, and 2025 HVAC service. Open floor plan connecting the kitchen, dining area, breakfast bar, and living room. Large dedicated laundry room

    Agent Photo

    Mary Jackowell

    Family First Realty Inc

    1505 Sparrow Rd, Chesapeake, VA 23325
  • /42

    Starting at $1,718

    Total Monthly Price

    • 1 - 3 Beds

    150 Coveside Ln, Chesapeake, VA 23320

    Welcome home to Hideaway at Greenbrier Luxury Apartment Homes, perfectly located in the prestigious Greenbrier area of Chesapeake, Virginia. Hideaway at Greenbrier offers one, two, and three-bedroom apartments, each well-appointed with a breakfast bar, den/study area and spectacular views. The apartment home also comes with either a sunroom or patio/balcony, plus and hardwood flooring in

    Hideaway at Greenbrier

    150 Coveside Ln, Chesapeake, VA 23320
  • 3016 Aaron Dr, Chesapeake, VA 23323

    $375,000

    Sold Sep 16, 2026

    3016 Aaron Dr, Chesapeake, VA 23323

    • 4 Beds
    • 2.5 Baths
    • 1,550 Sq Ft
    • Built 1971

    Last Sold Summary

    • $242/SF
    • 14 Days On Market

    Current Estimated Value $358,883

    Last Listing Agent Andy Nelson Iron Valley Real Estate HR

    3016 Aaron Dr, Chesapeake, VA 23323
    • /31

      Est $686,072

      Not Listed For Sale

      2133 Summer Breeze Rd, Chesapeake, VA 23323

      • 6 Beds
      • 3.5 Baths
      • 2,929 Sq Ft
      • Built 2018
      2133 Summer Breeze Rd, Chesapeake, VA 23323

      Last Sold Summary

      • 131 Days On Market

      Last Listing Agent Wendy Saunders Keller Williams Williamsburg

  • /16

    $283,500

    $2K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft

    1128 Wright Ave, Chesapeake, VA 23324

    Come Fall In Love with this Absolutely Gorgeous Like New Professionally Renovated Home! Stunning All New Kitchen with Granite counters and Soft close cabinets. All New Stainless Steel Appliances. Enjoy Entertaining in the Open living space. Beautiful All New Bathroom. All New HVAC and Ducting, New Roof, siding, windows, water heater and even all new insulation. Every light fixture and socket is

    Agent Photo

    Jim Leland

    LPT Realty LLC

    1128 Wright Ave, Chesapeake, VA 23324
  • /41

    $2,900 Per Month

    • 4 Beds
    • 3.5 Baths
    • 2,120 Sq Ft
    • Condo for Rent

    1712 Defiance Dr, Chesapeake, VA 23323

    WELCOME TO 1712 DEFIANCE DRIVE, NESTLED IN THE RESORT STYLE WATERFRONT COMMUNITY ON BRYAN'S COVE IN CHESAPEAKE'S DEEP CREEK SOUTH AREA. BUILT IN 2022, THIS LIKE NEW STRAUSS MODEL CONDO OFFERS A BEAUTIFUL BLEND OF MODERN FINISHES AND THOUGHTFUL DESIGN. 4 SPACIOUS BEDROOMS & 3 1/2 BATHROOMS WITH A 1ST FLOOR BEDROOM AND FULL BATH, IDEAL FOR GUESTS, IN-LAWS, OR A PRIVATE HOMES OFFICE. GENEROUS 2,084

    Agent Photo

    Dan Lawson

    Atlantic Sothebys Int'l Realty

    1712 Defiance Dr, Chesapeake, VA 23323
  • 1050 Wingfield Ave, Chesapeake, VA 23325

    $365,000

    Sold Sep 09, 2026

    1050 Wingfield Ave, Chesapeake, VA 23325

    • 4 Beds
    • 2 Baths
    • 1,722 Sq Ft
    • Built 1942

    Last Sold Summary

    • 2% Above List Price
    • $212/SF
    • 15 Days On Market

    Current Estimated Value $305,240

    Last Listing Agent Rashida Mahoney ONYX Realty Professionals LLC

    1050 Wingfield Ave, Chesapeake, VA 23325
    • /4

      Not Listed For Sale

      Lot 39 Trinkle St, Chesapeake, VA 23322

      Lot 39 Trinkle St, Chesapeake, VA 23322

      Last Sold Summary

      • 31 Days On Market

      Last Listing Agent Derek Greene The Greene Realty Group

  • /29

    $469,900

    Open Sat 10AM - 1PM
    • 5 Beds
    • 2 Baths
    • 1,800 Sq Ft

    1441 Whittamore Rd, Chesapeake, VA 23322

    Welcome to a rare opportunity in Chesapeake's sought-after Hickory school district! Set on a full acre, this beautifully transformed 5-bedroom, 2-bath home offers the space and setting to enjoy a touch of country living while staying near the conveniences of the city. The renovation goes far beyond cosmetics, with a new roof, siding, windows, HVAC, flooring, carpet, plumbing, septic tank,

    Agent Photo

    Alex Currie

    Long & Foster Real Estate Inc.

    1441 Whittamore Rd, Chesapeake, VA 23322
  • /35

    Starting at $1,254

    Total Monthly Price

    • 1 - 3 Beds

    3537 Towne Pointe Rd, Chesapeake, VA 23321

    Welcome to Chesapeake Pointe Apartments in Chesapeake, VA. Our pet-friendly one, two, and three-bedroom apartment homes are well-designed and offer access to two resort pools – AION SPLASH. This sprawling park-like community is located in both Chesapeake, VA and Portsmouth, VA. Chesapeake Pointe is minutes to I-664, I-64, Downtown Norfolk, Old Dominion University, and less than 13 miles to the

    Chesapeake Pointe

    3537 Towne Pointe Rd, Chesapeake, VA 23321
  • 1605 Stone Moss Reach Unit D, Chesapeake, VA 23320

    $205,000

    Sold Mar 03, 2026

    1605 Stone Moss Reach Unit D, Chesapeake, VA 23320

    • 2 Beds
    • 2 Baths
    • 978 Sq Ft
    • Built 1986

    Last Sold Summary

    • 2% Above List Price
    • $210/SF
    • 26 Days On Market

    Last Listing Agent Celia Romaine Keller Williams Coastal Virginia Chesapeake

    1605 Stone Moss Reach Unit D, Chesapeake, VA 23320
    • /49

      Est $484,710

      Not Listed For Sale

      1213 Eagle Pointe Way, Chesapeake, VA 23322

      • 3 Beds
      • 2.5 Baths
      • 2,397 Sq Ft
      • Built 2008
      1213 Eagle Pointe Way, Chesapeake, VA 23322

      Last Sold Summary

      • 83 Days On Market

      Last Listing Agent Sharon Baker BHHS RW Towne Realty LLC

  • /35

    $314,000

    $66K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 2,354 Sq Ft

    1417 Gust Ln, Chesapeake, VA 23323

    This unique property offers a main home and a separate second residence, creating flexibility that's hard to find. Whether you're looking for multigenerational living, a private in-law suite, rental income, guest accommodations, or space to run a home-based business (where permitted), this property adapts to your lifestyle. The main home features 3 bedrooms and 2.5 baths, while the second home

    Agent Photo

    Candice Myers

    BHHS RW Towne Realty

    1417 Gust Ln, Chesapeake, VA 23323
  • /19

    $1,600 Per Month

    • 1 Bed
    • 1 Bath
    • 750 Sq Ft
    • House for Rent

    802 Decatur St, Chesapeake, VA 23324

    Charming 1-bedroom carriage house apartment nestled in the heart of historic South Norfolk. This private and cozy space offers the perfect blend of character, convenience, and affordability. Enjoy easy access to major interstates, shopping, dining, entertainment, and all that Hampton Roads has to offer. The home features a functional layout, abundant natural light, and a comfortable living

    Agent Photo

    Debbie Childs

    RE/MAX Elevate

    802 Decatur St, Chesapeake, VA 23324
  • 4331 Oneford Place, Chesapeake, VA 23321

    $293,000

    Sold Feb 09, 2026

    4331 Oneford Place, Chesapeake, VA 23321

    • 2 Beds
    • 2.5 Baths
    • 1,875 Sq Ft
    • Built 2006

    Last Sold Summary

    • 1% Below List Price
    • $156/SF
    • 30 Days On Market

    Current Estimated Value $300,063

    Last Listing Agent Juanita Alexander EXIT Realty Central

    4331 Oneford Place, Chesapeake, VA 23321
    • /46

      Est $629,842

      Not Listed For Sale

      718 Firethorn Rd, Chesapeake, VA 23320

      • 4 Beds
      • 2.5 Baths
      • 2,956 Sq Ft
      • Built 1996
      718 Firethorn Rd, Chesapeake, VA 23320

      Last Sold Summary

      • 50 Days On Market

      Last Listing Agent Alison Mazzuca RE/MAX Capital

  • /50

    $589,900

    Open Sat 1PM - 3PM $35K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,963 Sq Ft

    705 Turnbuckle Ct, Chesapeake, VA 23322

    OPEN HOUSE SAT from 1 to 3 PM ~ BACK ON MARKET, NO FAULT OF SELLER ~ WATERFRONT LIVING IN GREAT BRIDGE! Welcome to “The Lake House,” a waterfront retreat tucked away on a quiet cul-de-sac in the sought-after Great Bridge school district. Offering nearly 3,000 square feet, 4 bedrooms and 2.5 baths, this home was made for enjoying life on the water—with peaceful views from many of the rooms

    Agent Photo

    Christine Cahoon

    Real Broker LLC

    705 Turnbuckle Ct, Chesapeake, VA 23322
  • /36

    Starting at $1,725

    Total Monthly Price

    • 1 - 3 Beds

    1314 Kingston Way, Chesapeake, VA 23320

    Offering 1, 2, and 3 bedrooms floorplans to suit every lifestyle and perfectly located in Chesapeake, Greenbrier Woods on the Lake is steps away from a variety of dining and shopping options and easy interstate access. Gorgeously appointed floorplans amid graceful landscaping blends the convenience of this prime location with the scenic views of a park setting. Community amenities include a

    Greenbrier Woods Apartments

    1314 Kingston Way, Chesapeake, VA 23320
  • 1316 Head of River Rd, Chesapeake, VA 23322

    $580,000

    Sold Jun 05, 2026

    1316 Head of River Rd, Chesapeake, VA 23322

    • 3 Beds
    • 2 Baths
    • 2,626 Sq Ft
    • Built 1962

    Last Sold Summary

    • 1% Above List Price
    • $221/SF
    • 19 Days On Market

    Current Estimated Value $591,730

    Last Listing Agent James Williams Atlantic Connection Real Estate

    1316 Head of River Rd, Chesapeake, VA 23322
    • /16

      Est $387,857

      Not Listed For Sale

      1210 Macdonald Rd, Chesapeake, VA 23325

      • 3 Beds
      • 1 Bath
      • 1,729 Sq Ft
      • Built 1958
      1210 Macdonald Rd, Chesapeake, VA 23325

      Last Sold Summary

      • 189 Days On Market

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

  • /47

    $489,000

    $11K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,225 Sq Ft

    539 Schaefer Ave, Chesapeake, VA 23321

    This beautifully maintained home that offers the look and feel of new construction. . . without the wait! Thoughtfully upgraded with custom finishes throughout, this home perfectly blends modern style with everyday comfort.Step inside to discover an open, light-filled floor plan featuring a stunning custom accent wall that adds warmth and character to the main living space. The spacious

    Agent Photo

    Kristen Boyd

    Next Chapter VA Realty Inc

    539 Schaefer Ave, Chesapeake, VA 23321
  • /17

    $1,100 Per Month

    • 2 Beds
    • 1 Bath
    • Apartment for Rent

    803 Ohio St, Chesapeake, VA 23324

    Available immediately. Call today to set up a showing.

    Agent Photo

    Dan Lawson

    Atlantic Sothebys Int'l Realty

    803 Ohio St, Chesapeake, VA 23324
  • 1308 Fairhaven Rd, Chesapeake, VA 23322

    $530,000

    Sold Apr 10, 2026

    1308 Fairhaven Rd, Chesapeake, VA 23322

    • 4 Beds
    • 2.5 Baths
    • 2,233 Sq Ft
    • Built 1995

    Last Sold Summary

    • 1% Below List Price
    • $237/SF
    • 16 Days On Market

    Current Estimated Value $537,737

    Last Listing Agent Michael Morisi Better Homes & Gdns Ntv Am Grp

    1308 Fairhaven Rd, Chesapeake, VA 23322
    • /16

      Est $278,552

      Not Listed For Sale

      619 Pine Bend, Chesapeake, VA 23320

      • 3 Beds
      • 1.5 Baths
      • 1,220 Sq Ft
      • Built 1979
      619 Pine Bend, Chesapeake, VA 23320

      Last Sold Summary

      • 84 Days On Market

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

  • /47

    $849,800

    • 6 Beds
    • 4.5 Baths
    • 3,251 Sq Ft

    2537 Number Ten Ln, Chesapeake, VA 23323

    RARE FIND IN CHESAPEAKE! Nearly 3 acres of space, privacy, and endless possibilities surround this stunning home. Inside, a bright open layout and show-stopping kitchen with an oversized island, granite countertops, stainless steel appliances, and double ovens create the perfect setting for everyday living and entertaining. Step outside to a screened porch, above-ground pool, and expansive

    Agent Photo

    Delia Longoria

    1st Class Real Estate Allianz

    2537 Number Ten Ln, Chesapeake, VA 23323
  • /43

    Starting at $1,505 Plus Fees

    • 1 - 2 Beds

    200 Red Cedar Ct, Chesapeake, VA 23320

    Welcome to The Cedars at Greenbrier. Our convenient location puts you exactly where you want to be. We offer our residents the finest in modern amenities, including a luxury pool, fitness center, playground with picnic areas, clubhouse, and waterfront living! Our location offers you living in the city, but away from the hustle and bustle of everyday life. With several floor plans, The Cedars at

    The Cedars at Greenbrier

    200 Red Cedar Ct, Chesapeake, VA 23320
  • 4044 Devon Dr, Chesapeake, VA 23321

    $625,000

    Sold Jan 30, 2026

    4044 Devon Dr, Chesapeake, VA 23321

    • 4 Beds
    • 2.5 Baths
    • 3,072 Sq Ft
    • Built 1994

    Last Sold Summary

    • $203/SF
    • 21 Days On Market

    Current Estimated Value $640,780

    Last Listing Agent Debbie Gutekunst Iron Valley Real Estate HR

    4044 Devon Dr, Chesapeake, VA 23321
    • /11

      Est $334,784

      Not Listed For Sale

      3404 Port Chambers Ct, Chesapeake, VA 23321

      • 3 Beds
      • 1.5 Baths
      • 1,442 Sq Ft
      • Built 1969
      3404 Port Chambers Ct, Chesapeake, VA 23321

      Last Sold Summary

      • 42 Days On Market

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

  • /26

    $275,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,544 Sq Ft

    1602 Shell Rd, Chesapeake, VA 23323

    Welcome to this 3 Bed, 2.5 bath home in Chesapeake! Offering a functional layout with plenty of space throughout, this home provides flexibility for everyday living and entertaining. Enjoy comfortable living areas, well-sized bedrooms, and the convenience of two full baths plus a half bath and an attached 1 car garage. Conveniently located with access to shopping, dining, and major roadways. Some

    Agent Photo

    Jacob Bronk

    Own Real Estate LLC

    1602 Shell Rd, Chesapeake, VA 23323
  • /16

    $2,100 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,254 Sq Ft
    • Condo for Rent

    624 Ridge Cir, Chesapeake, VA 23320

    Step into this beautifully maintained 2-bedroom, 2.1-bathroom condo offering a spacious and inviting layout perfect for comfortable living. Move-in ready and thoughtfully designed, this home features everything you need to settle in with ease. Conveniently located just minutes from shopping centers, restaurants, and everyday amenities. Immediate occupancy available. Schedule your private showing

    Agent Photo

    Marie DePedro

    World Class Realty & Prop Mgmt

    624 Ridge Cir, Chesapeake, VA 23320
  • 1101 Fairway Dr, Chesapeake, VA 23320

    $703,000

    Sold Apr 22, 2026

    1101 Fairway Dr, Chesapeake, VA 23320

    • 4 Beds
    • 4 Baths
    • 3,630 Sq Ft
    • Built 1989

    Last Sold Summary

    • 5% Above List Price
    • $194/SF
    • 23 Days On Market

    Current Estimated Value $703,515

    Last Listing Agent Gayle Upchurch BHHS RW Towne Realty

    1101 Fairway Dr, Chesapeake, VA 23320
    • /39

      Est $883,165

      Not Listed For Sale

      326 Greens Edge Dr, Chesapeake, VA 23322

      • 5 Beds
      • 3.5 Baths
      • 3,994 Sq Ft
      • Built 2003
      326 Greens Edge Dr, Chesapeake, VA 23322

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Kathie David Howard Hanna William E. Wood

  • /46

    $899,999

    Pending
    • 4 Beds
    • 3.5 Baths
    • 3,381 Sq Ft

    2917 Buskey Rd, Chesapeake, VA 23322

    Picture yourself on this idyllic front porch with your favorite rocking chairs! This gorgeous Cape Cod home sits on a peaceful 3.12-acre lot with picturesque curb appeal. At 3,381 square feet, this turnkey home is clean with fresh updates! The backyard is a total dream with a sparkling inground pool, fenced backyard + barn/workshop with a lean-to. Striking open concept features vaulted ceilings,

    Agent Photo

    Amy Camasso

    The Real Estate Group

    2917 Buskey Rd, Chesapeake, VA 23322
  • /88

    Starting at $1,725 Plus Fees

    • 1 - 3 Beds

    2540 Holly Point Blvd, Chesapeake, VA 23325

    Visit Us Today!Holly Point Apartments in Chesapeake, Virginia was planned for inspired living. Every effort has been made to provide you with the best: the best environment, the best amenities the best in all things that make life more pleasurable.Seize your chance to live in one of the premier apartment communities in Chesapeake, VA. Picture coming home every day to the warm embrace of

    Holly Point

    2540 Holly Point Blvd, Chesapeake, VA 23325
  • 209 Rose Ash Way, Chesapeake, VA 23320

    $410,000

    Sold Aug 21, 2026

    209 Rose Ash Way, Chesapeake, VA 23320

    • 3 Beds
    • 2 Baths
    • 1,455 Sq Ft
    • Built 1998

    Last Sold Summary

    • $282/SF
    • 18 Days On Market

    Current Estimated Value $400,685

    Last Listing Agent Christopher O'Brien Howard Hanna Real Estate Svcs.

    209 Rose Ash Way, Chesapeake, VA 23320
    • /27

      Est $243,123

      Not Listed For Sale

      1800 Westgate St, Chesapeake, VA 23324

      • 4 Beds
      • 1 Bath
      • 1,308 Sq Ft
      • Built 1952
      1800 Westgate St, Chesapeake, VA 23324

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Kelly Henson RE/MAX Supercenter

Showing Results 1 - 40, Page 1 of 18

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