Deep Creek-Portsmouth Homes for Sale

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  $430,000 Open Mon 5PM - 7PM

  • 3 Beds
  • 2.5 Baths
  • 1,975 Sq Ft

  1830 Whelp Way, Chesapeake, VA 23323

  Live easy in this beautifully updated 3-bedroom, 2.5-bath end-unit townhome in Chesapeake’s sought-after Grassfield district! With 1,975 sq ft of space, this home features brand new carpet, fresh paint, and a bright open layout great for everyday living or entertaining. The kitchen shines with white cabinetry, stainless steel appliances, and great flow into the living and dining areas. Enjoy

  Betsy Thompson The Agency

  1830 Whelp Way, Chesapeake, VA 23323
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  $299,900

  • 4 Beds
  • 1 Bath
  • 1,587 Sq Ft

  185 George Washington Hwy S, Chesapeake, VA 23323

  Waterfront ranch home on almost half an acre of land! This home has been newly renovated with all new paint, lighting, fixtures, flooring, appliances, carpet and more! Open kitchen with granite countertops and stainless steel appliances. Beautifully remodeled bathroom. Spacious, finished attic serves as a bedroom. Big windows for great natural light. Backyard with covered porch and stone path.

  Joshua Britt Prodigy Realty

  185 George Washington Hwy S, Chesapeake, VA 23323
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  $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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  $365,000

  • 3 Beds
  • 2.5 Baths
  • 1,577 Sq Ft

  1717 Defiance Dr, Chesapeake, VA 23323

  The Beethoven isn’t your typical townhome—it feels like a single-family home! Walk in through your private 1-car garage to a flexible space great for a rec room, office, or gym, plus a big storage area. Upstairs, the main level has an open layout with a bright living room and a kitchen that checks all the boxes: granite or quartz countertops, island, pantry, and a balcony for your morning coffee.

  Julian Rivera Iron Valley Real Estate Norfolk

  1717 Defiance Dr, Chesapeake, VA 23323
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  $280,000

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

  3108 Aaron Dr, Chesapeake, VA 23323

  The seller offers a $600.00 credit towards the buyer's choice of dishwasher.This ranch-style home was fully remodeled in 2013 with quality upgrades throughout. Featuring a newer roof, windows, and siding updated in 2013. Step inside to find ceramic flooring, a stylish kitchen with granite countertops, modern cabinets, and stainless steel appliances.Both bathrooms were updated in 2013 with

  Darrell Moore CENTURY 21 Top Producers

  3108 Aaron Dr, Chesapeake, VA 23323
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  $415,000

  • 4 Beds
  • 3.5 Baths
  • 2,120 Sq Ft

  1712 Defiance Dr, Chesapeake, VA 23323

  WELCOME TO 1712 DEFIANCE DRIVE, NESTLED IN THE RESORT STYLE WATERFRONT COMMUNITY ON BRYAN'S COVE IN CHESAPEAKES 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 HOME OFFICE. GENEROUS

  Dan Lawson GreenTree Realty Inc.

  1712 Defiance Dr, Chesapeake, VA 23323
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  $460,000

  • 3 Beds
  • 2.5 Baths
  • 2,573 Sq Ft

  907 Adventure Way, Chesapeake, VA 23323

  Located in the heart of Grassfield, this like-new Chesapeake townhome is a must see! Situated on a desirable corner lot, this beautifully maintained home features an open-concept design with a spacious living room, dining area and gourmet kitchen. The kitchen boasts granite countertops, a stylish backsplash, gas cooking, stainless steel appliances and a walk-in pantry. Enjoy the ease of a

  Tammy Busche Long & Foster Real Estate Inc.

  907 Adventure Way, Chesapeake, VA 23323
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  $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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  $199,700

  • Land
  • 5 Acres
  • $39,940 per Acre

  4729 Sunray Ave, Chesapeake, VA 23321

  Perfect opportunity to own 5 acres in the Western Branch zone of Chesapeake. 2 Acres in front are cleared and 3 acres in back are partially wooded. Property is zoned A1 - check with City of Chesapeake for endless possibilities for this property. Take a ride around the neighborhood, and you will find new country chic farm homes, horses, farm equipment, crops....lots of ways to be close to city

  LeAnn Amory BHHS RW Towne Realty

  4729 Sunray Ave, Chesapeake, VA 23321
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  $285,000

  • 4 Beds
  • 1.5 Baths
  • 1,145 Sq Ft

  2404 Livesay Rd, Chesapeake, VA 23323

  Great starter home, just for you. Convenient to interstate, main roads, shopping and schools. Open conceit floor plan. All appliances convey as is. Separate in-law suite or work out room/office. Go see this one first. Don't hesitate

  Tamara Lawrence Vision Real Estate Group LLC

  2404 Livesay Rd, Chesapeake, VA 23323
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  $615,000

  • 4 Beds
  • 2.5 Baths
  • 2,849 Sq Ft

  2000 Kelsey Bay Ct, Chesapeake, VA 23323

  Welcome to the Mill Creek Harbor neighborhood! This MOVE-IN ready home is located in the highly sought-after Grassfield section of Chesapeake, zoned for Grassfield schools. This nice sized corner lot is in a cul-de-sac with a beautifully maintained landscape offering a welcoming curb appeal. As you step inside, this home immediately shows off its' nice sized square footage with high ceilings and

  Richard Febus Next Chapter VA Realty Inc

  2000 Kelsey Bay Ct, Chesapeake, VA 23323
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  $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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  $675,000

  • 4 Beds
  • 2 Baths
  • 1,860 Sq Ft

  253 George Washington Hwy S, Chesapeake, VA 23323

  Bring your horses and your dreams to this rare 6+ acre oasis in Grassfield high school district of Chesapeake! Fully equipped for equestrian living, the property features a 10-stall barn with tack room, feed room, storage, and half bath, plus a lighted riding ring and two sheds—including one to be installed. Zoned for horses, boarding stables and riding academy and just minutes from major roads

  Kimberly Denton BHHS RW Towne Realty

  253 George Washington Hwy S, Chesapeake, VA 23323
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  $480,000

  • 5 Beds
  • 3.5 Baths
  • 2,354 Sq Ft

  1415 Gust Ln, Chesapeake, VA 23323

  Explore the many possibilities of this unique property. It is comprised of 2 houses, 2 garages, 2 sheds, 2 electric meters, a deck, a patio & plenty of parking. House #1 has 3 bedrooms and 2.1 baths. House #2 has 2 bedrooms and 1 bath. Qualified buyers call to make an appointment for a private showing.

  Sandy Nance BHHS RW Towne Realty

  1415 Gust Ln, Chesapeake, VA 23323
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  $489,900

  • 3 Beds
  • 2.5 Baths
  • 2,000 Sq Ft

  2505 Calonia Arch, Chesapeake, VA 23323

  Welcome to this charming 3-bedroom, 2.5-bath home in Deep Creek! A versatile FROG can serve as a 4th bedroom, office, or man cave. The roof is just 5 years old, and a new water heater (2024) adds modern efficiency. Enjoy a peaceful pond view in the backyard and relax. Inside, the home offers a bright, spacious layout with cozy living areas. Conveniently located within minutes of shopping, dining,

  Ken Capps World Class Realty

  2505 Calonia Arch, Chesapeake, VA 23323
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  $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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  $6,000

  • Land
  • 0.18 Acre
  • $33,149 per Acre

  .181AC Shipyard Rd, Chesapeake, VA 23323

  An exceptional opportunity awaits with this 7,884 sqft parcel of prime land is perfect for expanding existing property coverage or creating additional development potential. Situated in a highly desirable location, this spacious lot offers flexibility for various residential applications. Whether you are looking to increase property value or enhance your investment portfolio, this land provides

  Tarane Parker BHHS RW Towne Realty

  .181AC Shipyard Rd, Chesapeake, VA 23323
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  $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
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  $100,000

  • Land
  • 0.42 Acre
  • $238,095 per Acre

  910 Willis St, Chesapeake, VA 23323

  Tyler Keffer Keffer Realty

  910 Willis St, Chesapeake, VA 23323
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  $100,000

  • Land
  • 0.19 Acre
  • $526,316 per Acre

  912 Willis St, Chesapeake, VA 23323

  Tyler Keffer Keffer Realty

  912 Willis St, Chesapeake, VA 23323
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  $533,750 New Construction

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

  2821 Margaret Booker Dr, Chesapeake, VA 23323

  Gorgeous new (ready to move in) new construction by local builder with more than 5000 units built. Granite/LVP/Luxury tiled shower/WIC's/open floorplan/2-car garage/covered porch/SS fridge-range-microwave-dishwasher/garage door opener...all included. Walk to schools all the way from 1st grade to 12th grade graduation within three blocks! 2 blocks from recreation center w/tennis courts/BBall, gym,

  Jimmy Reece The Real Estate Group

  2821 Margaret Booker Dr, Chesapeake, VA 23323
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  $669,900 New Construction

  • 5 Beds
  • 3 Baths
  • 2,350 Sq Ft

  2116 Cedar Rd, Chesapeake, VA 23323

  Rare find on Cedar Road! This 5-bedroom, 3-bath home offers over 2,300 sq ft on 2.5 acres with a wooded backyard for a true mini wilderness escape. Features include LVP flooring, first-floor bedroom with full bath, quartz counters, tile backsplash, pendant lighting, and a two-car garage. The primary suite boasts a garden tub and tile shower. Modern finishes and private acreage—this home will not

  Marcus Anderson Iron Valley Real Estate Norfolk

  2116 Cedar Rd, Chesapeake, VA 23323
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  $474,900 New Construction

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

  2152 Millville Rd, Chesapeake, VA 23323

  READY TO IMPRESS! This modern 4 bedroom, 2.5 bathroom home offers 2,200 sqft of open, thoughtfully designed living. Enjoy durable luxury vinyl plank floors and a bright, airy layout that's ideal for both everyday comfort and chic entertaining. The chef-inspired kitchen boasts sleek cabinetry, gleaming granite countertops, and an oversized center island that flows into the dining and living zones.

  Shynara Manley ONYX Realty Professionals LLC

  2152 Millville Rd, Chesapeake, VA 23323
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  $179,000

  • Land
  • 0.73 Acre
  • $245,205 per Acre

  2702 Cedar Rd, Chesapeake, VA 23323

  Fantastic opportunity to build your dream home, wooded lot just under 3/4 acre in Deep Creek section of Chesapeake. Access to city water and sewer. Call Today!

  Bob Glasgow RE/MAX Allegiance

  2702 Cedar Rd, Chesapeake, VA 23323
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  $324,700

  • 4 Beds
  • 2 Baths
  • 2,222 Sq Ft

  3201 Jean Ct, Chesapeake, VA 23323

  Charming 4 bedroom 2 bath brick ranch . This 2,222-sqft home sits on over a half acre corner lot. Home offers office, dining and living room, large family room, large screened in deck and so much more . Come see take a look!

  Katrina Ellis CENTURY 21 Nachman Realty

  3201 Jean Ct, Chesapeake, VA 23323

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