Chesapeake, VA Homes

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  /29

  $469,900

  • 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,

  

  Alex Currie

  Long & Foster Real Estate Inc.

  1441 Whittamore Rd, Chesapeake, VA 23322
• Explore Chesapeake

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  /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

  

  Andy Nelson

  Iron Valley Real Estate HR

  900 Billy Obrien Ln, Chesapeake, VA 23322
• 

  $190,000

  Sold Sep 09, 2026

  2201 Rock Cliff Reach Unit A, Chesapeake, VA 23320

  • 2 Beds
  • 2 Baths
  • 978 Sq Ft
  • Built 1987

  Last Sold Summary

  • 10% Below List Price
  • $194/SF
  • 25 Days On Market

  Last Listing Agent Keisha Rorie Shipmate Real Estate +JPAR

  2201 Rock Cliff Reach Unit A, Chesapeake, VA 23320
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  /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
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  /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

  

  Candice Myers

  BHHS RW Towne Realty

  1417 Gust Ln, Chesapeake, VA 23323
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  /42

  Starting at $1,641

  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
• 

  $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
• 

  

  /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
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  /50

  $600,000

  $25K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,963 Sq Ft

  705 Turnbuckle Ct, Chesapeake, VA 23322

  BACK ON MARKET, SUBJECT TO RELEASE, 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 throughout the

  

  Christine Cahoon

  Real Broker LLC

  705 Turnbuckle Ct, Chesapeake, VA 23322
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  /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

  

  Dan Lawson

  Atlantic Sothebys Int'l Realty

  1712 Defiance Dr, Chesapeake, VA 23323
• 

  $330,000

  Sold Aug 31, 2026

  312 Esplanade Place, Chesapeake, VA 23320

  • 2 Beds
  • 2.5 Baths
  • 1,568 Sq Ft
  • Built 1994

  Last Sold Summary

  • $210/SF
  • 7 Days On Market

  Current Estimated Value $346,358

  Last Listing Agent Melinda Swager NextHome Tidewater Realty

  312 Esplanade Place, Chesapeake, VA 23320
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  /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
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  /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

  

  Kristen Boyd

  Next Chapter VA Realty Inc

  539 Schaefer Ave, Chesapeake, VA 23321
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  /35

  Starting at $1,219

  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
• 

  $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
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  /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
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  /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

  

  Delia Longoria

  1st Class Real Estate Allianz

  2537 Number Ten Ln, Chesapeake, VA 23323
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  /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

  

  Debbie Childs

  RE/MAX Elevate

  802 Decatur St, Chesapeake, VA 23324
• 

  $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
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  /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
• 

  

  /26

  $275,000

  Under Contract

  • 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

  

  Jacob Bronk

  Own Real Estate LLC

  1602 Shell Rd, Chesapeake, VA 23323
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  /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
• 

  $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
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  /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,

  

  Amy Camasso

  The Real Estate Group

  2917 Buskey Rd, Chesapeake, VA 23322
• 

  

  /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.

  

  Dan Lawson

  Atlantic Sothebys Int'l Realty

  803 Ohio St, Chesapeake, VA 23324
• 

  $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
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  /45

  $399,800

  • 4 Beds
  • 2 Baths
  • 2,460 Sq Ft

  624 Rock Dr, Chesapeake, VA 23323

  Make this your first stop! This beautifully updated brick ranch in the desirable Oak Manor neighborhood was fully remodeled in 2022 and offers the perfect combination of style, space, and functionality. Featuring 4 spacious bedrooms, 2 full bathrooms, and an attached garage, this move-in-ready home has room for everyone. The thoughtful renovation included updated flooring, paint, lighting, and

  

  Matthew Salway

  Iron Valley Real Estate HR

  624 Rock Dr, Chesapeake, VA 23323
• 

  

  /88

  Starting at $1,685 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
• 

  $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
• 

  

  /43

  $415,000

  • 3 Beds
  • 2 Baths
  • 1,610 Sq Ft

  2924 Taylor Rd, Chesapeake, VA 23321

  Pride of ownership shows throughout this move-in-ready brick ranch in the sought-after Western Branch school district. Fully renovated in 2021, this 3-bedroom, 2.5-bath home features updated flooring, appliances, and cabinetry, along with a sunken family room and attached 1-car garage. Enjoy the screened-in back porch overlooking a spacious backyard with wooded views. The property includes two

  

  Maritza Brandon

  The Real Estate Group

  2924 Taylor Rd, Chesapeake, VA 23321
• 

  

  /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

  

  Marie DePedro

  World Class Realty & Prop Mgmt

  624 Ridge Cir, Chesapeake, VA 23320
• 

  $532,500

  Sold Sep 24, 2025

  904 Will Scarlet Way, Chesapeake, VA 23322

  • 4 Beds
  • 2.5 Baths
  • 2,200 Sq Ft
  • Built 1996

  Last Sold Summary

  • $242/SF
  • 33 Days On Market

  Current Estimated Value $533,549

  Last Listing Agent Brian Wurst A Better Way Realty Inc.

  904 Will Scarlet Way, Chesapeake, VA 23322
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  /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
• 

  

  /41

  $329,500

  Pending

  • 4 Beds
  • 1.5 Baths
  • 1,580 Sq Ft

  1217 Oleander Ave, Chesapeake, VA 23325

  Bring your vision and unlock the potential of this all-brick ranch! Featuring 4 bedrooms, 1.5 bathrooms, an excellent spot to add another, this house offers endless possibilities. With fresh paint, solid bones, and a great backyard, this home is ready for someone to add their personal touch and build instant sweat equity. The converted garage, with an easy opportunity to add an additional full

  

  Katie Prescott

  Long & Foster Real Estate Inc.

  1217 Oleander Ave, Chesapeake, VA 23325
• 

  

  /31

  Starting at $2,017 Plus Fees

  • 1 - 3 Beds

  111 Gateway Ct, Chesapeake, VA 23320

  Dream big with a stylishly modern apartment home at the The Morgan. Here, you'll find resort-inspired amenities that beg you to rest and relax and interiors that create easy, everyday joys. Surrounded by everything you love to do in Chesapeake, Virginia, near Greenbrier Mall, you'll feel inspired to keep life colorful. Lean into luxury and choose from a variety of pet-friendly 1, 2 & 3 bedroom

  The Morgan

  

  111 Gateway Ct, 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
• 

  

  /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

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