Chesapeake, VA Homes for Sale

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  /33

  $565,000

  • 3 Beds
  • 2.5 Baths
  • 2,347 Sq Ft

  2621 Smithson Dr, Chesapeake, VA 23322

  Meticulously maintained ranch home with an inviting open-concept floor plan! Features a large living room with fireplace, formal dining room, and a spacious kitchen with granite counters, stainless steel appliances, and a generous eat-in area. The primary suite offers an ensuite bath with double vanity, jacuzzi tub, separate shower, and walk-in closet. A finished room over the garage includes a

  

  Diana Brink

  A Better Way Realty Inc.

  (757) 960-3364

  2621 Smithson Dr, Chesapeake, VA 23322
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  /36

  $398,000

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

  800 Monroe Ct, Chesapeake, VA 23320

  Nestled in the heart of Greenbrier, this end-unit condo sits on a tranquil cul-de-sac with upgraded interior trim, to include crown molding and expansive base molding. The inviting home is further offers custom paint, a spacious living room, formal dining area with glass french doors, and seamlessly integrated family room showcase the epitome of comfort, leading to an inviting kitchen. The

  

  Chris Faircloth

  Swell Realty Co

  (757) 384-5756

  800 Monroe Ct, Chesapeake, VA 23320
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  /46

  $434,999

  • 3 Beds
  • 2.5 Baths
  • 1,932 Sq Ft

  417 Heartfield Dr, Chesapeake, VA 23322

  Modern living meets everyday comfort! This stunning 3-bed, 2.5-bath townhouse-style condo was built in 2019 and still feels brand new. Enjoy a first-floor primary suite, open-concept layout, and a finished bonus room over the garage—perfect for an office, gym, or man cave! The kitchen offers bar seating, stainless appliances, and plenty of storage, including a pantry and walk-in attic. Relax in

  

  Dycallon James

  Keller Williams Town Center

  (757) 654-1107

  417 Heartfield Dr, Chesapeake, VA 23322
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  /33

  $399,999

  • 4 Beds
  • 2 Baths
  • 1,877 Sq Ft

  3032 Barn Way, Chesapeake, VA 23323

  This cape cod home is stylish, serene and spacious! Tucked away on a quiet dead end street with a cul-de-sac, 3032 Barn Way welcomes you home. The flexible layout offers the option of a first-floor primary suite with full bath or a private retreat upstairs. The main level features an open kitchen with all appliances conveying and a formal dining room with French doors. It's great for gatherings

  

  Jackie Feagin

  BHHS RW Towne Realty

  (757) 290-1211

  3032 Barn Way, Chesapeake, VA 23323
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  /46

  $419,000

  • 3 Beds
  • 2.5 Baths
  • 2,036 Sq Ft

  1808 Aft Way, Chesapeake, VA 23323

  Welcome home to the beautiful Mendelssohn model home in Bryan's Cove that features a 2-car garage & massive rec room w/ access to private back yard on the first level. The main living level kitchen includes granite, an island, a dining area, a pantry & access to an 8'x18' deck. The kitchen opens to a generous & bright living room with a conveniently placed powder room. Upstairs are 2 bedrooms w/

  

  Kara Evalenko

  Real Broker LLC

  (757) 697-8390

  1808 Aft Way, Chesapeake, VA 23323
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  /28

  $248,000

  • 2 Beds
  • 2 Baths
  • 1,169 Sq Ft

  1016 Thoroughgood Way Unit 100, Chesapeake, VA 23324

  Welcome to this spacious condo located in a well-maintained traditional-style building with secured entrance, elevator access, and an intercom system for added peace of mind. This beautifully designed unit features two oversized bedrooms and two generously sized bathrooms, offering both comfort and convenience. The open-concept kitchen includes a large breakfast bar with seating for 4–6, Great

  

  Michele Salyer

  A Better Way Realty Inc.

  (757) 290-8046

  1016 Thoroughgood Way Unit 100, Chesapeake, VA 23324
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  /50

  $1,349,000

  • 5 Beds
  • 6 Baths
  • 4,387 Sq Ft

  516 Peaceful Rd, Chesapeake, VA 23322

  Tucked away on 3 private acres in Caroon Farms, this stunning all-brick estate is a rare blend of elegance, comfort, and nature. This 5 bedroom, 4 full and 2 half bath home offers a private guest, student, or in-law suite, a chef's kitchen, spa-inspired baths, and an oversized flex space. Outdoor living is unmatched-framed by lush blooms, the 15,000 gallon, two tier koi pond with a tranquil

  

  Janice Myers-Hollowell

  BHHS RW Towne Realty

  (757) 697-7481

  516 Peaceful Rd, Chesapeake, VA 23322
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  /18

  $248,900

  • 2 Beds
  • 2 Baths
  • 1,169 Sq Ft

  1016 Thoroughgood Way Unit 201, Chesapeake, VA 23324

  Make this your first stop! Beautifully maintained, low maintenance, open concept, second floor condo! Building is secured with intercom and fob access. This two bedroom, two bathroom unit will immediately feel like your new home. The bedrooms have dormers to bring in extra light and open up the space. Primary bedroom has a spacious walk-in closet and en-suite bathroom with a walk-in shower.

  

  Matthew Salway

  Iron Valley Real Estate Hampton Roads

  (757) 367-8488

  1016 Thoroughgood Way Unit 201, Chesapeake, VA 23324
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  /49

  $2,400,000

  • 3 Beds
  • 2 Baths
  • 1,070 Sq Ft

  1924 Sanderson Rd, Chesapeake, VA 23322

  Bridlewood Farm, a premier equestrian estate located in the Hickory School District of Chesapeake, VA, blends elegance and functionality. Morton-built barns overlook lush pastures, a 2-acre pond with bass and catfish, and top-tier riding facilities for all levels. The turn-key property features 42 stalls with 12x12s, mats, auto-waterers, and wash stalls with hot/cold water. A 100’x200’ indoor

  

  Caleb Hooker

  Mossy Oak Properties/Land and Farms Realty

  (757) 505-7439

  1924 Sanderson Rd, Chesapeake, VA 23322
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  /43

  $430,000

  • 4 Beds
  • 2.5 Baths
  • 2,483 Sq Ft

  1244 Bell Tower Arch, Chesapeake, VA 23324

  Come view this great 4 bedroom traditional home in Chesapeake located at the end of a large cul-de-sac. This home has large living areas; great for entertaining with floor plan that is open between living room, kitchen, and eat-in area. The back door leads out to a spacious yard with privacy fence and good space on either side of the home. The primary bedroom is large and offers a large walk-in

  

  Jerome Caddell

  KFinCo Realty

  (757) 654-1738

  1244 Bell Tower Arch, Chesapeake, VA 23324
• 

  /2

  $100,000

  • Land
  • 0.11 Acre
  • $934,579 per Acre

  813 Mullen Rd, Chesapeake, VA 23320

  43' x 108' buildable lot. Convenient to shopping and mass transit. Mostly cleared, one small bush or two..

  

  Cindy Caskey

  BHHS RW Towne Realty

  (757) 982-9465

  813 Mullen Rd, Chesapeake, VA 23320
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  /42

  $495,000

  • 4 Beds
  • 2 Baths
  • 1,948 Sq Ft

  3154 Martin Johnson Rd, Chesapeake, VA 23323

  Welcome to your California-style dream home on nearly an acre of private paradise! This beautifully upgraded home blends high-end finishes with timeless comfort—and is loaded with jaw-dropping features inside and out. Features & Highlights: • Built-in surround sound system throughout the home—perfect for entertaining or relaxing • Built-in tilting TV that seamlessly swivels for

  

  Sarah Romero

  Real Broker LLC

  (757) 294-8201

  3154 Martin Johnson Rd, Chesapeake, VA 23323
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  /47

  $650,000

  • 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

  (757) 786-8081

  253 George Washington Hwy S, Chesapeake, VA 23323
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  /48

  $419,900

  • 5 Beds
  • 3 Baths
  • 2,433 Sq Ft

  948 Hollywood Dr, Chesapeake, VA 23320

  This five bedroom, three full bath brick ranch with covered front porch sits on a little over half an acre. There is a separate In-laws suite with two bedrooms, living room and full bath with walk-in shower. There is also a separate exterior entrance through a set of French doors. Hardwood floors through out the house along with the In-laws suite. Primary bedroom in main house has its own

  

  David Cacace

  BHHS RW Towne Realty

  (757) 378-0799

  948 Hollywood Dr, Chesapeake, VA 23320
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  /14

  $160,000

  • Land
  • 0.56 Acre
  • $287,253 per Acre

  Par B George Washington Hwy S, Chesapeake, VA 23323

  Commercial Building Lot priced below Chesapeake Assessment value! Located on the Dismal Swamp Canal & George Washington Hwy across street from Shopping Center. Property is on navigable Dismal Swamp Canal. Property Zoning is B-1 with over 250 feet of road frontage.

  

  John Horton

  Samson Properties

  (757) 296-1605

  Par B George Washington Hwy S, Chesapeake, VA 23323
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  /25

  $274,900

  • 3 Beds
  • 2 Baths
  • 1,235 Sq Ft

  308 Taft Dr, Portsmouth, VA 23701

  Renovated Brick Ranch Home- so many beautiful new features to include New Roof, HVAC, Kitchen, Bathrooms and more. Enter this fresh home into the living room which is open to the dining and kitchen. Kitchen boasts all new cabinets, granite countertops and new SS appliances. The Hallway leads you to the bedrooms where you will find bedroom 2 & 3 and the hall bathroom. The primary suite is large -

  

  Rachel Beasley

  Own Real Estate LLC

  (757) 530-7306

  308 Taft Dr, Portsmouth, VA 23701
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  /25

  $269,900

  • 3 Beds
  • 1.5 Baths
  • 1,400 Sq Ft

  511 Appomattox St, Norfolk, VA 23523

  This renovated home is move-in-ready and absolutely adorable! New LVP flooring in living spaces, new carpet in bedrooms and tile in the bathrooms. Stunning kitchen with new cabinets, granite countertops and new Stainless-Steel appliances. All new lighting and plumbing fixtures, new siding, new roof, new HVAC. Lovely front porch and a great back yard. Make this lovely home yours before ethe

  

  Rachel Beasley

  Own Real Estate LLC

  (757) 863-6645

  511 Appomattox St, Norfolk, VA 23523
• 

  $579,900 New Construction

  • 5 Beds
  • 2.5 Baths
  • 2,522 Sq Ft

  Swan Plan, Chesapeake, VA

  

  Classic Design Builders

  Builder

  0 Shell Place St Unit 37905457, Chesapeake, VA
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  /37

  $637,755 Open Sat 1PM - 4PM

  • 3 Beds
  • 3.5 Baths
  • 2,500 Sq Ft

  909 Calhoun Way, Chesapeake, VA 23322

  To Be Built- Under Construction w/ January Delivery! Custom arches to soaring 10' ceilings and stunning hardwood floors. The open-concept effortlessly blends the Dining and Great Rooms, with two sets of French doors leading to your own private courtyard and patio, your personal oasis for outdoor living. Chef's kitchen is a showstopper w/oversized island, and sleek Quartz counters. Generous First

  

  Monique Darling

  BHHS RW Towne Realty

  (757) 908-6767

  909 Calhoun Way, Chesapeake, VA 23322
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  /42

  $774,900 New Construction

  • 5 Beds
  • 3.5 Baths
  • 3,000 Sq Ft

  343 Ewell Ln, Chesapeake, VA 23322

  Welcome to Hickory! Experience this exquisite custom home, crafted by the esteemed Overholt Contracting, a reputable builder with 40+ yrs of expertise. This modern design caters perfectly to today’s family lifestyle, featuring 2 spacious primary suites and three additional lg bedrooms, alongside a convenient first-floor home office. The exterior boasts durable James Hardie fiber cement siding, an

  

  Denise Hawkins

  Triumph Realty

  (757) 891-5226

  343 Ewell Ln, Chesapeake, VA 23322
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  /50

  $749,900 New Construction

  • 5 Beds
  • 3.5 Baths
  • 3,000 Sq Ft

  345 Ewell Ln, Chesapeake, VA 23322

  Welcome to Hickory! Experience this exquisite custom home, crafted by the esteemed Overholt Contracting, a reputable builder with 40+ yrs of expertise. This modern design caters perfectly to today’s family lifestyle, featuring 2 spacious primary suites and 3 additional lg bedrooms, alongside a convenient first-floor home office. The exterior boasts durable James Hardie fiber cement siding, an

  

  Denise Hawkins

  Triumph Realty

  (757) 367-8323

  345 Ewell Ln, Chesapeake, VA 23322
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  /12

  $640,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,522 Sq Ft

  Pelican Plan, Chesapeake, VA 23323

  

  Classic Design Builders

  Builder

  805 Shell Rd Unit 37905445, Chesapeake, VA 23323
• 

  

  /10

  $545,000 New Construction

  • 5 Beds
  • 2 Baths
  • 2,496 Sq Ft

  Gannett Plan, Chesapeake, VA 23323

  

  Classic Design Builders

  Builder

  805 Shell Rd Unit 37905421, Chesapeake, VA 23323
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  /50

  $251,000

  • 2 Beds
  • 2 Baths
  • 1,545 Sq Ft

  3826 Whitechapel Arch, Chesapeake, VA 23321

  Opportunity meets location in this Western Branch end unit townhouse. This home is ready for a refresh and offers the chance to shape your own space. With 2 bedrooms, 2 full baths, attached garage and large drive way, this house gives you the freedom to design it your way. All of this, set in one of Chesapeake’s most desirable areas, near parks, shopping, schools, and easy interstate access. HUD

  Susan Jenkins Better Homes&Gardens R.E. Native American Grp

  3826 Whitechapel Arch, Chesapeake, VA 23321
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  /50

  $1,349,000

  • 5 Beds
  • 5 Baths
  • 4,200 Sq Ft

  306 Scone Castle Loop, Chesapeake, VA 23322

  Former HOMEARAMA Custom Showcase Home in the desirable Edinburgh community! Designed with whole-home organization by Closet Factory, this home is packed with built-ins and thoughtful details throughout — including a custom pantry, master closet, mudroom, window seats, theater room, and office/library. The downstairs master suite is a true retreat, featuring a private sitting area, a luxurious

  Jessica Downes RE/MAX Allegiance

  306 Scone Castle Loop, Chesapeake, VA 23322
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  /29

  $360,000

  • 4 Beds
  • 2.5 Baths
  • 2,350 Sq Ft

  4004 River Breeze Cir, Chesapeake, VA 23321

  Open House 10/24 5-7, 10/25 11-1, 10/26 1-3! Welcome to this beautiful home in the desirable River Breeze Community! This open-concept sanctuary offers effortless entertaining with rooms that seamlessly flow together. Bright, freshly painted interior & professionally cleaned carpets provide a clean canvas for you to personalize, & columns in the living room that add a unique charm. Cozy up to the

  MarQuita Holloway KW Coastal Chesapeake Virginia LLC

  4004 River Breeze Cir, Chesapeake, VA 23321
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  /50

  $185,000

  • 3 Beds
  • 2.5 Baths
  • 1,432 Sq Ft

  2046 Christian Ave, Chesapeake, VA 23324

  Great opportunity for investors or buyers looking to add value. Fix & Flip or fix and hold opportunity!This home offers solid bones and great potential. With some updating, it could provide steady rentalincome or strong resale value. Minutes from major highways, shopping, and local amenities.

  Candice West Better Homes&Gardens R.E. Native American Grp

  2046 Christian Ave, Chesapeake, VA 23324
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  /34

  $370,000

  • 4 Beds
  • 3 Baths
  • 1,987 Sq Ft

  1425 Seaboard Ave, Chesapeake, VA 23324

  Welcome home to an inviting foyer that opens to a true first-floor bedroom or study and a full bath on the main level offers flexible living. Luxury Vinyl Plank flooring carries through the downstairs into a spacious, open-concept layout. The family room centers around a clean-lined fireplace and flows into a well-appointed kitchen featuring soft-close 42" white shaker cabinetry, granite

  Craig Houston AtCoastal Realty

  1425 Seaboard Ave, Chesapeake, VA 23324
• 

  

  /45

  $579,000

  • 4 Beds
  • 2.5 Baths
  • 2,396 Sq Ft

  1000 Fox Ridge Ct, Chesapeake, VA 23322

  This updated brick beauty combines charm, comfort, and convenience in the highly sought-after Grassfield school district with no HOA. Nestled on a peaceful cul-de-sac, the home welcomes you with stunning curb appeal and warm hardwood floors. Entertain in the formal living and dining rooms or gather in the bright kitchen with island and breakfast nook overlooking private wooded views. The family

  Allen Boone Redfin Corporation

  1000 Fox Ridge Ct, Chesapeake, VA 23322
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  /17

  $229,000

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

  4309 Hillingdon Bend Unit 303, Chesapeake, VA 23321

  Welcome to Unit 303 at Kings Pointe, a perfect blend of comfort and convenience! Located just off I-64, Exit 11B in Western Branch, this newer community offers easy access to dining, shopping, and local amenities. The 2-bedroom, 2-bathroom condo sits on the top floor, providing stunning, unobstructed views. Enjoy the luxury of a clubhouse, pool, trails, grills, firepits, and plenty of guest

  Judy Reed Judy Reed Realty

  4309 Hillingdon Bend Unit 303, Chesapeake, VA 23321
• 

  

  /34

  $629,900

  • 3 Beds
  • 3 Baths
  • 2,146 Sq Ft

  2207 Carolina Rd, Chesapeake, VA 23322

  Welcome to 2207 Carolina Rd—a place where comfort meets functionality in the heart of Chesapeake. Imagine mornings with your favorite music playing through the built-in Bose speakers in the kitchen, evenings unwinding on the deck, and pets enjoying the amazing view. This home offers peace of mind with a new roof, dual-zone HVAC systems with Ecobee smart thermostats, and a vapor barrier with

  Natalie Carrier Redfin Corporation

  2207 Carolina Rd, Chesapeake, VA 23322
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  /30

  $369,000

  • 2 Beds
  • 2.5 Baths
  • 1,712 Sq Ft

  333 Sikeston Ln, Chesapeake, VA 23322

  Welcome to 333 Sikeston Lane — a beautifully appointed 2-bed, 3-bath home featuring sparkling granite-style countertops, stainless steel appliances, and an open-concept design that seamlessly connects the kitchen, dining, and living areas. Step outside to your private deck off the kitchen—an ideal spot for al fresco dining or morning coffee. Located just a few miles from excellent amenities:

  Annie Speckhart Redfin Corporation

  333 Sikeston Ln, Chesapeake, VA 23322
• 

  

  /29

  $439,900

  • 4 Beds
  • 2 Baths
  • 1,794 Sq Ft

  1400 Fentress Rd, Chesapeake, VA 23322

  Step into a timeless sanctuary nestled on a serene 1-acre lot, this charming 4-bedroom, 2-bathroom home offers the perfect blend of tranquility and convenience. Enjoy the privacy and peace of country living while still being within easy reach of city amenities. Step inside to find spacious interiors filled with natural light and cozy ambiance. Originally built circa 1898, this property exudes

  David Perry David Perry Realty LLC

  1400 Fentress Rd, Chesapeake, VA 23322
• 

  

  /45

  $765,740 New Construction

  • 5 Beds
  • 4 Baths
  • 3,537 Sq Ft

  1236 Kidbrooke St, Chesapeake, VA 23322

  Welcome to the 3,537 sq ft Hadley model, featuring a modern open-concept living space designed for ultimate comfort and versatility. The main level boasts a spacious great room, a bright sunroom, and a generous casual dining area. The kitchen is perfect for any home chef, complete with a large center island, walk-in pantry, and plenty of counter space for all your culinary needs. The flex room

  D.R. Horton Builder

  1236 Kidbrooke St, Chesapeake, VA 23322
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  /35

  $574,990 New Construction

  • 2 Beds
  • 3 Baths
  • 1,685 Sq Ft

  2144 Edwin Dr, Chesapeake, VA 23322

  Welcome to The Charleston, one of our beautifully designed quad-style homes, offering 2,314 square feet of living space. This home features a covered front porch, three spacious bedrooms, and three full bathrooms, along with a two-car garage for added convenience. At the heart of the home, the open great room with vaulted ceilings and a cozy corner fireplace creates the perfect space for both

  D.R. Horton Builder

  2144 Edwin Dr, Chesapeake, VA 23322
• 

  

  /46

  $697,740 New Construction

  • 4 Beds
  • 3 Baths
  • 2,761 Sq Ft

  100 Agave Ct, Chesapeake, VA 23322

  Welcome to the 2,761 sq ft Hadley model, featuring a modern open-concept living space designed for ultimate comfort and versatility. The main level boasts a spacious great room, a bright sunroom, and a generous casual dining area. The kitchen is perfect for any home chef, complete with a large center island, walk-in pantry, and plenty of counter space for all your culinary needs. The flex room

  D.R. Horton Builder

  100 Agave Ct, Chesapeake, VA 23322
• 

  

  /23

  $583,740 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,631 Sq Ft

  2008 Munro Ln, Chesapeake, VA 23322

  Welcome to the Shenandoah, a beautifully designed 2,631 sq ft home offering a modern open-concept living space that is perfect for both entertaining and family living. The main level features a spacious family room, a kitchen with luxury finishes, a home office, laundry room, mud room, and an additional open living space, creating an ideal flow for daily activities. The first-floor primary suite

  D.R. Horton Builder

  2008 Munro Ln, Chesapeake, VA 23322
• 

  

  /35

  $733,740 New Construction

  • 5 Beds
  • 4 Baths
  • 3,165 Sq Ft

  1239 Kidbrooke St, Chesapeake, VA 23322

  The Summit floorplan offers a generous 3,165 sq ft of living space across two floors, providing ample room for families of all sizes. The main level features a first-floor bedroom and full bathroom, an office or formal dining room, and a beautiful kitchen that opens to the great room, filled with natural light. The gourmet kitchen is a standout with a large kitchen island, quartz countertops,

  D.R. Horton Builder

  1239 Kidbrooke St, Chesapeake, VA 23322
• 

  

  /23

  $584,990 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,433 Sq Ft

  2021 Barton Ln, Chesapeake, VA 23322

  Welcome to the Shenandoah, a beautifully designed 2,433 sq ft home offering a modern open-concept living space that is perfect for both entertaining and family living. The main level features a spacious family room, a kitchen with luxury finishes, a home office, laundry room, mud room, and an additional open living space, creating an ideal flow for daily activities. The first-floor primary suite

  D.R. Horton Builder

  2021 Barton Ln, Chesapeake, VA 23322
• 

  

  /23

  $584,990 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,433 Sq Ft

  2013 Barton Ln, Chesapeake, VA 23322

  Welcome to the Shenandoah, a beautifully designed 2,433 sq ft home offering a modern open-concept living space that is perfect for both entertaining and family living. The main level features a spacious family room, a kitchen with luxury finishes, a home office, laundry room, mud room, and an additional open living space, creating an ideal flow for daily activities. The first-floor primary suite

  D.R. Horton Builder

  2013 Barton Ln, Chesapeake, VA 23322

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