Chesapeake, VA Homes for Sale under $400,000

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  /14

  $305,000 Open Sun 1PM - 3PM

  • 2 Beds
  • 2.5 Baths
  • 1,330 Sq Ft

  303 Middle Oaks Dr, Chesapeake, VA 23322

  Nicely appointed townhome, great location, close to amenities. No HOA, POA or condo fees. Come see this home before it's gone. All upgrades are approx. 7 yrs old. HVAC was replaced 2019, New fence in 2025

  Merrill Getto Keffer Realty

  303 Middle Oaks Dr, Chesapeake, VA 23322
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  /21

  $340,000

  • 3 Beds
  • 2.5 Baths
  • 1,603 Sq Ft

  1440 Otterbourne Cir, Chesapeake, VA 23320

  Well maintained 3-bedroom, 2.5-bath home nestled in the heart of Greenbrier! Features an open-concept layout with a bright living area, spacious kitchen with stainless appliances, ample cabinetry, and a cozy dining space. The primary suite offers a walk-in closet and private bath for relaxation. Enjoy a fully fenced backyard that's great for entertaining. Located on a quiet neighborhood with easy

  Whitney Mikel Keller Williams Coastal Virginia Chesapeake

  1440 Otterbourne Cir, Chesapeake, VA 23320
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  /50

  $365,000

  • 3 Beds
  • 2.5 Baths
  • 2,151 Sq Ft

  179 Harbor Watch Dr, Chesapeake, VA 23320

  Welcome to this beautifully upgraded 3-bedroom, 2.5-bath condo nestled in the highly sought-after Great Bridge area. This stunning property offers the perfect blend of comfort, style, and waterfront lifestyle—with breathtaking water views and a private boat slip just steps from your door. Inside, you'll find a spacious and thoughtfully designed layout with tons of storage and closet space

  Jessica Downes RE/MAX Allegiance

  179 Harbor Watch Dr, Chesapeake, VA 23320
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  /21

  $399,900

  • 3 Beds
  • 2.5 Baths
  • 1,902 Sq Ft

  5029 Pughsville Rd, Chesapeake, VA 23321

  Dont miss this opportunity to buy here in Western Branch. Well maintained home new paint throughout home. New carpet upstairs, large Primary with onsuite bath with double sinks. Easy access to all of Hampton Roads and peninsula via 664. Western branch schools. Solar panels make utilities a breeze. New Counters in Kitchen sink and disposal.

  Timothy Hayes Swell Realty Co

  5029 Pughsville Rd, Chesapeake, VA 23321
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  /29

  $324,500

  • 4 Beds
  • 2 Baths
  • 1,742 Sq Ft

  1546 Jackson Ave, Chesapeake, VA 23324

  Newly renovated bungalow home featuring 4 bedrooms and 2 bathrooms, including a first floor bedroom and full bathroom, a gorgeous kitchen with all new stainless steel appliances, granite countertops, and white shaker cabinetry, and much more! All new LVP flooring throughout and ceramic bathroom floors. Spacious backyard space and cozy front porch. Come tour today!

  Joshua Britt Prodigy Realty

  1546 Jackson Ave, Chesapeake, VA 23324
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  /2

  $375,000

  • Land
  • 3.77 Acres
  • $99,575 per Acre

  743 Bedford St, Chesapeake, VA 23322

  This is a 3+ acre lot zoned A1 for agriculture use and barns. Build your own barn for your personal equipment or animals. Potential for commercial office/warehouse use with a conditional use variance from the Chesapeake City Council and Navy. Septic and well approvals are available. This lot cannot be used for a residential building site and air rights have been sold off. Owner will consider

  Robert Wadsworth Pungo Realty LLC

  743 Bedford St, Chesapeake, VA 23322
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  /31

  $339,900

  • 3 Beds
  • 2 Baths
  • 1,571 Sq Ft

  2021 Christopher Dr, Chesapeake, VA 23321

  Classic 3 bdrm 2 ba brick ranch in highly sought-after area. This solid home is situated on a corner lot in well-established neighborhood with easy commute to interstate, shopping & shipyards. It offers a spacious layout with open concept kitchen, primary bdrm with en suite & generous sized closet, an inviting living room filled with natural light, wood burning fireplace & hardwood floors. Recent

  Jennifer Franklin Fit Realty

  2021 Christopher Dr, Chesapeake, VA 23321
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  /21

  $320,000

  • 3 Beds
  • 2 Baths
  • 1,431 Sq Ft

  2916 Doris Ave, Chesapeake, VA 23324

  Welcome to 2916 Doris Avenue, a well-maintained all-brick ranch in the vibrant Sunrise Hills community. This charming 3-bedroom, 1-1/2 bath home offers approx. 1,431 sqft of single-level living on a deep 8,233 sqft fenced lot—suited for outdoor enjoyment. Inside, discover inviting laminate flooring and a bright, open layout. Recent updates (2022) include a new roof, fresh paint, new windows, and

  Anna Paduhovich EXP Commercial LLC

  2916 Doris Ave, Chesapeake, VA 23324
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  /48

  $306,000

  • 3 Beds
  • 2.5 Baths
  • 1,492 Sq Ft

  2042 Berkley Ave, Chesapeake, VA 23324

  Step into this charming gem! Completely remodeled! This beautifully maintained home offers timeless character blended with thoughtful updates – making it move-in ready and full of potential. Plenty of natural light and updated light fixtures! Enjoy the HUGE private balcony from the primary bedroom on the 2nd floor. Custom tile work with granite countertops, and all new stainless-steel appliances.

  Angela Kennedy 1st Class Real Estate Integrity

  2042 Berkley Ave, Chesapeake, VA 23324
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  /30

  $359,900

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  3128 Biscayne Dr, Chesapeake, VA 23321

  Move-in ready brick ranch in sought-after Taylorwood Estates neighborhood of Western Branch! This well-maintained home features 3 bedrooms, 2 baths, and attached 2-car garage. Enjoy the welcoming entry foyer, dining room, and open living/family room with a cozy gas fireplace. The kitchen boasts Corian countertops and gas range, great for entertaining. Relax in the spacious primary bedroom with

  Catherine LeFante BHHS RW Towne Realty

  3128 Biscayne Dr, Chesapeake, VA 23321
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  /39

  $310,000

  • 4 Beds
  • 2 Baths
  • 1,275 Sq Ft

  3931 Port Rd, Chesapeake, VA 23321

  Step into this beautifully refreshed, 4 bedroom 2 full bath all brick, home featuring an open-concept layout that’s perfect for modern living. The spacious kitchen is complete with a natural gas stove, ample cabinetry, and a large bar that seamlessly connects to the living area—ideal for entertaining or enjoying everyday life. Tucked away in an established neighborhood with convenient access to

  Daniel Jones A Better Way Realty Inc.

  3931 Port Rd, Chesapeake, VA 23321
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  /20

  $379,900

  • 3 Beds
  • 2.5 Baths
  • 1,871 Sq Ft

  218 Gregg St, Chesapeake, VA 23320

  Been waiting for the perfect opportunity and want to get the kids settled before the school year starts? Here's yourchance! This beauty just needs a little TLC to make her your own! Enjoy the convenient 1st floor primary w/ walkin closet, two additional bedrooms upstairs, and a spacious loft, stainless steel appliances and several modernfixtures have been updated, with just a few more

  Juanita Alexander EXIT Realty Central

  218 Gregg St, Chesapeake, VA 23320
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  /30

  $380,000

  • 4 Beds
  • 2.5 Baths
  • 2,235 Sq Ft

  4308 Center Mast Crest, Chesapeake, VA 23321

  Sitting on one of the largest lots in the community, this home offers a backyard perfect for entertaining or relaxing. Conveniently close to military bases, shopping, and expressway access just a short drive to Virginia Beach and Newport News. Inside, you’ll find a 4-bedroom, 2.5-bath open floor plan with fresh paint. The eat-in kitchen with island flows into a cozy family room with fireplace,

  Stephen Simmons Creed Realty

  4308 Center Mast Crest, Chesapeake, VA 23321
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  /40

  $300,000 Open Sat 11AM - 1PM

  • 2 Beds
  • 2.5 Baths
  • 1,327 Sq Ft

  631 Sedgefield Ct, Chesapeake, VA 23322

  Cute as a Button, this updated and spacious brick front Townhome is Move in Ready! Located in the Cedar Mill neighborhood and attends all Great Bridge Schools. This lovely and impressive Gem offers a brand new HVAC system with programmable thermostat, new electric water heater, new wide plank LVP flooring on the first floor, new carpeting on stairs and 2nd floor, and freshly painted interior

  Rachael Kraft Turner GreenTree Realty Inc.

  631 Sedgefield Ct, Chesapeake, VA 23322
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  /42

  $369,900

  • 4 Beds
  • 2 Baths
  • 2,030 Sq Ft

  3114 Tournament Dr, Chesapeake, VA 23323

  REMODELED, NEW TILE IN BATHROOM, NEW BATHROOM VANITIES, NEW GRANITE KITCHEN COUNTER TOPS, NEW FLOORS, NEW FIXTURE LIGHTS AND MUCH MORE.

  Nelson Vedia World Class Realty

  3114 Tournament Dr, Chesapeake, VA 23323
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  /34

  $389,567

  • 3 Beds
  • 2.5 Baths
  • 1,920 Sq Ft

  5148 Winery Dr, Chesapeake, VA 23321

  This beautiful 2-story home is not in an association with everything you need for your family with 3 spacious bedrooms, 2.5 baths, 2 living room areas, a dining room, and a fully fenced backyard for children, pets, or simply enjoying being outside. New HVAC & mini spilt June ’25. Efficient layout features bright, airy living spaces with great natural light. The inviting living room for relaxing

  Jessica Fitzwilliam The Real Estate Group

  5148 Winery Dr, Chesapeake, VA 23321
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  /32

  $325,000

  • 4 Beds
  • 3 Baths
  • 1,696 Sq Ft

  900 Avalon Ave, Chesapeake, VA 23324

  Welcome to 900 Avalon Avenue, a delightful 4-bedroom, 3-bathroom residence nestled on a spacious corner lot in Chesapeake. This 1,696 sq. ft. home blends comfort and convenience, featuring carpet and LVP flooring, stainless steel appliances, and a movable kitchen island. The deck out back is perfect for entertaining or relaxing. This home is located near the shipyard, BAE Systems, and the

  Genesis Juarez ONYX Realty Professionals LLC

  900 Avalon Ave, Chesapeake, VA 23324
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  /26

  $395,000

  • 4 Beds
  • 3.5 Baths
  • 2,136 Sq Ft

  4227 Meander Way, Chesapeake, VA 23321

  Why wait for new construction when you can move right into this nearly new 3-story townhome in Fairview Towns, a gated community in Chesapeake's sought-after Western Branch area? Only one year old and thoughtfully upgraded with modern kitchen hardware and custom touches, this home blends the feel of new with benefits of immediate move-in. Enjoy low-maintenance living with easy access to shopping,

  Helen Tucker Tucker Professional Services LLC

  4227 Meander Way, Chesapeake, VA 23321
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  /19

  $339,000 Open Sat 11AM - 1PM

  • 4 Beds
  • 2 Baths
  • 1,747 Sq Ft

  2929 Hilton Ave, Chesapeake, VA 23324

  Great spacious 4-bedroom, 2-bath ranch featuring large bedrooms; large primary suite complete with wireless speaker for ultimate relaxation; enjoy cooking in the updated kitchen complete with granite counter tops and cabinets and updated bathrooms. This home offers 8 yr old double-hung windows; new hot water heater and the option to reveal hardwood flooring throughout. Features a newly

  Stephanie Lane Keller Williams Realty Town Center

  2929 Hilton Ave, Chesapeake, VA 23324
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  /48

  $365,000 Open Sun 12PM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 2,062 Sq Ft

  4195 Taughtline Loop, Chesapeake, VA 23321

  Welcome to this beautiful 3-bedroom, 2.5-bath condo in Goose Creek Estates, located in the sought-after Western Branch area. With nearly 2,100 square feet of living space and an attached 1-car garage, this home offers comfort, space, and convenience.The spacious primary suite features a custom walk-in closet, while an additional flex room could be a home office, playroom, or guest space. The open

  Karly Diggs Real Broker LLC

  4195 Taughtline Loop, Chesapeake, VA 23321
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  /25

  $309,900

  • 4 Beds
  • 2 Baths
  • 1,440 Sq Ft

  1214 Hull St, Chesapeake, VA 23324

  Don't miss your chance to have all the perks of a new construction home without the price tag! This historic home has been lovingly updated throughout- you will feel like you are stepping into a brand new home! This home features new flooring throughout the entire home with new LVP floors on the first floor and brand new carpet on the second floor. All of the bathrooms boast new vanities,

  Marquis Bynum A Better Way Realty Inc.

  1214 Hull St, Chesapeake, VA 23324
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  /24

  $309,900

  • 2 Beds
  • 2.5 Baths
  • 1,434 Sq Ft

  864 Rivanna River Reach, Chesapeake, VA 23320

  Welcome to this charming condo, located in the desirable Kingsford section of the Riverwalk community. This well-maintained, move-in ready home features 2 bedrooms, 2.5 bathrooms, and a spacious open-concept floor plan with fresh interior paint.The main level offers a bright great room with cathedral ceilings and a fireplace, seamlessly connected to the enclosed patio, prime for

  Calvin Robinson Realty Specialists

  864 Rivanna River Reach, Chesapeake, VA 23320
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  /12

  $304,000

  • 3 Beds
  • 1.5 Baths
  • 950 Sq Ft

  3006 Menands Dr, Chesapeake, VA 23325

  New new new! Everything in the home has been remodeled brand new. This is a must come and see. Bring us an offer on your new home. Closing costs are negotiable.

  Jai Johnson EXIT Realty Central

  3006 Menands Dr, Chesapeake, VA 23325
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  /39

  $369,900

  • 3 Beds
  • 2.5 Baths
  • 1,835 Sq Ft

  1428 Otterbourne Cir, Chesapeake, VA 23320

  Enjoy the benefits of a low-maintenance lifestyle while savoring the comforts of a thoughtfully maintained home. Whether unwinding in the spacious living area, or enjoying a gourmet meal in your large dining room, or hosting friends for a summer barbecue on the private patio, this home is designed to elevate everyday living. The community itself offers a welcoming atmosphere and amenities that

  Kevin Carr EXP Realty LLC

  1428 Otterbourne Cir, Chesapeake, VA 23320
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  /25

  $379,000

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

  1444 Culpepper Ave, Chesapeake, VA 23323

  Pictures don't do this justice. Old Ranch turned into 2025 Open Floor plan just like TV. All new appliances & hot water heater. New Roof, Windows and siding. All new inside, doors, floors and ceiling fans & lights. Bathrooms New too. Kitchen, Kitchen, Kitchen. Cabinets to ceilings, Central island for entertaining huge great room. Did you need that "extra room" converted garage will suffice.

  Jay Kotchka BHHS RW Towne Realty

  1444 Culpepper Ave, Chesapeake, VA 23323
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  /11

  $389,000

  • 3 Beds
  • 2.5 Baths
  • 1,855 Sq Ft

  2565 Fieldsway Dr, Chesapeake, VA 23320

  Welcome to this stunning luxury townhome offering the perfect blend of style, comfort, and convenience. Step inside to a spacious open floorplan designed for modern living. The kitchen is a dream, featuring granite countertops, stainless steel appliances, and a large island that flows seamlessly into the expansive living and dining areas. Enjoy beautiful LVP flooring throughout the first floor,

  Geoffrey Whiteside Keller Williams Town Center

  2565 Fieldsway Dr, Chesapeake, VA 23320
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  /50

  $370,000

  • 4 Beds
  • 2.5 Baths
  • 2,014 Sq Ft

  5029 John St, Chesapeake, VA 23321

  Spacious 4 bedroom, 2.5 bath two story home near highways, shopping and bases. Formal LR and DR near the front entry. Continue back to a large Family Room, Breakfast area and open Kitchen. Powder room is opposite the laundry leading to a single car attached garage. Relax on the elevated deck overlooking the cozy backyard sloping down to a wooded area with a creek. Owners' suite with walk-in

  Jim Martin RE/MAX Allegiance

  5029 John St, Chesapeake, VA 23321
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  /20

  $315,000

  • 4 Beds
  • 2 Baths
  • 1,385 Sq Ft

  402 Stalham Rd Unit A, Chesapeake, VA 23325

  Well maintained Ranch on a LARGE lot with a shaded front porch for sitting! The property has an open space to the left of the house for your vision. Open concept with reasonably sized bedrooms. Kitchen includes stainless steel appliances with lots of cabinet space. Fireplace in a large living room. Workshop/shed at rear is 12×24 but as-is. Plenty of driveway space. Nearby library and easy

  Drew Miller 1st Class Real Estate Mid-Atlantic

  402 Stalham Rd Unit A, Chesapeake, VA 23325
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  /19

  $359,900

  • 4 Beds
  • 2 Baths
  • 1,968 Sq Ft

  2932 Sunrise Ave, Chesapeake, VA 23324

  Beautiful and spacious renovated home in established Sunrise Hills community featuring 4 bedrooms, 2 full baths, and a half bath that boasts original gleaming hardwood floors, formal dining room, and many upgrades including new roof, Two new HVAC units, recently installed vinyl siding, windows, carpet and backyard deck. Updates kitchen with new stainless steel appliances.

  Ralph Harvey ListWithFreedom.com Inc

  2932 Sunrise Ave, Chesapeake, VA 23324
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  /5

  $300,000

  • Land
  • 0.34 Acre
  • $882,353 per Acre

  917 Brice Ct, Chesapeake, VA 23322

  Build your dream home on this spacious vacant lot located in a quiet, family-friendly subdivision. Situated on a level parcel with utility connections available at the street (water, sewer, electricity), this lot offers the perfect blend of privacy and community. Enjoy well-maintained surroundings, paved roads, and close proximity to schools, shopping centers, parks, and major highways. Whether

  Patty Cohen RE/MAX Allegiance

  917 Brice Ct, Chesapeake, VA 23322
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  /23

  $315,000

  • 3 Beds
  • 2 Baths
  • 1,252 Sq Ft

  1736 Lockard Ave, Chesapeake, VA 23320

  Welcome to this charming 3-bedroom, 2-bath ranch located in the heart of Chesapeake. With 1,252 square feet of living space, this well-maintained home offers fresh new flooring in both the living room and eat-in kitchen. Enjoy meals in the cozy breakfast/dining area. Please note that the chandelier does not convey and will be replaced before closing. The home also features newer appliances, a

  Frank Filippone BHHS RW Towne Realty

  1736 Lockard Ave, Chesapeake, VA 23320
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  /40

  $399,000

  • 4 Beds
  • 2.5 Baths
  • 1,578 Sq Ft

  1708 Bounty Reach, Chesapeake, VA 23323

  Stunning 3-story home in a beautiful community! Built in 2021 with modern upgrades, natural light filling every corner and sleek recessed lighting that makes for an open airy environment. The ground level "rec room" has been converted to a 4th bedroom which can be used as either a home office, gym, or playroom. Upstairs, enjoy open-concept living & kitchen with an oversized island, granite

  Brittany Morgan Iron Valley Real Estate Prestige

  1708 Bounty Reach, Chesapeake, VA 23323
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  /25

  $309,777

  • 2 Beds
  • 2.5 Baths
  • 1,341 Sq Ft

  1821 Volvo Pkwy, Chesapeake, VA 23320

  Welcome to this beautiful lakeside townhome in the heart of Greenbrier! With a low-maintenance lifestyle, a great view & open floor plan, this 1,341 sqft home has two large master suites each containing their own full baths. Bulkhead (2013), Enjoy the view from your large custom deck overlooking private lake suitable for swimming, paddle boarding, canoeing and boating. This Plantation Lakes

  Jessica Fitzwilliam The Real Estate Group

  1821 Volvo Pkwy, Chesapeake, VA 23320
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  /11

  $369,000

  • Land
  • 14.91 Acres
  • $24,748 per Acre

  LOT 2 Shillelagh Rd, Chesapeake, VA 23323

  Fantastic opportunity to purchase 14.91 acres in the Grassfield area of Chesapeake. Buyer to do all necessary due diligence. Sellers do not have a survey or any additional information about the parcel. Numerous possibilities with this much land!

  Wanda Adams RE/MAX Alliance

  LOT 2 Shillelagh Rd, Chesapeake, VA 23323
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  /3

  $395,000

  • Land
  • 10 Acres
  • $39,500 per Acre

  10 AC Millville Rd, Chesapeake, VA 23323

  10 ACRES, THAT CAN BE SUBDIVIDED, SOME WETLAND ( CALL FOR WETLAND MAP) 15-S POSSIBLE TO DEVELOP 10-15 or 52 TOWNHOUSES THE DEEP CREEK AREA OF CHESAPEAKE WITH CITY WATER SEWAGE, LAND IS LOCATED JUST PAST THE INTERSECTION OF MILLVILLE RD AND ROCKWOOD DR. ADJACENT SUMMER PARK DIVISION..

  Lenay Wilson Coldwell Banker Premier

  10 AC Millville Rd, Chesapeake, VA 23323
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  /7

  $349,000

  • Land
  • 11.45 Acres
  • $30,480 per Acre

  8 Shillelagh Rd, Chesapeake, VA 23323

  Beautiful 11.453 acres of wooded lot in the heart of chesapeake located in the Grassfield area. If you are quiet you may get lucky and see some deer or even a wild turkey. Enjoy peaceful country living w nearby conveniences of schools, shopping, restaurants and access to the interstate. Check with the city of Chesapeake for building and other questions.

  Debbie Esposito Howard Hanna Real Estate Services

  8 Shillelagh Rd, Chesapeake, VA 23323
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  /6

  $350,000

  • Land
  • 38.8 Acres
  • $9,021 per Acre

  2057 Burson Dr, Chesapeake, VA 23323

  Ideal wooded +/- 38-acre building site with city sewer and water available. Boundary survey and environmental reports are available. Builder packages if interested or build your own home. Call agent for additional information.

  Robert Wadsworth Pungo Realty LLC

  2057 Burson Dr, Chesapeake, VA 23323
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  /2

  $365,000

  • 4 Beds
  • 2 Baths
  • 1,973 Sq Ft

  601 Wooddale Ct, Chesapeake, VA 23323

  Jordan L. Williams Keller Williams Coastal Virginia Chesapeake

  601 Wooddale Ct, Chesapeake, VA 23323
• 

  

  /19

  $384,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,642 Sq Ft

  4909 Apricot Way, Chesapeake, VA 23321

  Welcome to Breck Grove, an exquisite townhome community in Western Branch, Chesapeake, where fine finishes & quality construction meet modern living. This 2-level Laurel plan beautifully showcases an open floorplan w/ luxurious upgrades & a single car garage. The kitchen stuns guests w/ upgraded quartz countertops, subway tile backsplash, soft-close drawers & under cabinet lighting. Easily

  Angela McCaskill Corinth Realty LLC

  4909 Apricot Way, Chesapeake, VA 23321
• 

  

  /19

  $376,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,642 Sq Ft

  4903 Apricot Way, Chesapeake, VA 23321

  Welcome to Breck Grove, an exquisite townhome community in Western Branch, Chesapeake, where fine finishes & quality construction meet modern living. This Laurel plan beautifully showcases an open floorplan w/ luxurious upgrades & a single car garage. The kitchen stuns guests w/ soft-close cabinetry & drawers, granite countertops, tile backsplash, & under cabinet lighting. Easily maintained &

  Angela McCaskill Corinth Realty LLC

  4903 Apricot Way, Chesapeake, VA 23321

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