Chesapeake, VA Homes for Sale with Acreage

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  /28

  $725,000

  • 4 Beds
  • 2.5 Baths
  • 2,384 Sq Ft

  1517 Lookout Ct, Chesapeake, VA 23323

  Welcome to this beautifully maintained 5-acre property in Chesapeake's desirable Grassfield area. Built in 2020, this 4-bedroom, 2.5-bath home features freshly painted interiors, an open floor plan, and electric fireplaces with custom mantels. The spacious eat-in kitchen offers marble countertops and ample storage. Zoned for horses, the open acreage is ideal for equestrian use, recreation, or

  

  Barbora Jerabek

  BHHS RW Towne Realty

  (757) 330-1922

  1517 Lookout Ct, Chesapeake, VA 23323
• Explore Chesapeake

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  /49

  $2,390,000

  • 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

  MOP Land and Farms Realty

  (757) 505-7439

  1924 Sanderson Rd, Chesapeake, VA 23322
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  /2

  $250,000

  • Land
  • 1.17 Acres
  • $213,675 per Acre

  1+ac Wilton St, Chesapeake, VA 23324

  Left side of lot has new 2 car garage with an apartment above. Built in 2017 and never lived in. New AC unit. 30ft high ceilings in garage.

  Paul Dadaian Swell Realty Co

  1+ac Wilton St, Chesapeake, VA 23324
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  /50

  $693,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,600 Sq Ft

  2430 Ballahack Rd, Chesapeake, VA 23322

  UNDER CONSTRUCTION! 2 story Transitional Home boasting an open floorplan and situated on a 1 acre parcel in Southern Chesapeake. 4 Bedrooms and 3.5 baths. TWO PRIMARY SUITES: one UP and one DOWN! BOTH SUITES include a walk in closet and full bath with tile flooring and comfort height vanity with double bowls and granite counters. Large EAT IN KITCHEN opens to GREAT ROOM and features quartz

  Rachael Kraft Turner GreenTree Realty Inc

  2430 Ballahack Rd, Chesapeake, VA 23322
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  /50

  $1,185,000 Open Sun 1PM - 3PM

  • 5 Beds
  • 3 Baths
  • 3,661 Sq Ft

  2100 Saint Brides Rd W, Chesapeake, VA 23322

  Welcome to this stunning custom-built home set on 3.5 acres in a sought-after Chesapeake location. Offering 5 bedrooms and 3 bathrooms across 3,661 square feet, this home features two spacious living levels designed for both everyday comfort and entertaining. The open layout includes generous counter space, a well-appointed kitchen, surround sound in the main living area, and seamless flow into

  Betsy Thompson The Agency

  2100 Saint Brides Rd W, Chesapeake, VA 23322
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  /21

  $272,900

  • 4 Beds
  • 1 Bath
  • 1,856 Sq Ft

  1213 Fentress Rd, Chesapeake, VA 23322

  Bring your imagination! This 4 bedroom, 1 bathroom home in Chesapeake is waiting for your vision! With over 1,800 square feet, this home has a ton of space to create something special! Situated on a spacious lot! Wonderful opportunity for an investor or buyer looking to build equity! Call today for more information and to schedule your tour!

  Jonathan Melvin Benham Real Estate LLC

  1213 Fentress Rd, Chesapeake, VA 23322
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  /16

  $804,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,606 Sq Ft

  2100 Sanderson Rd, Chesapeake, VA 23322

  The Henderson by Kirbor Homes is a timeless favorite. As you cross the threshold, the light-filled layout invites you into a spacious great room that seamlessly connects to a chef-inspired kitchen. Soak in mornings filled with the aroma of breakfast, as the expansive island becomes a hub for conversations, laughter & the sweet anticipation of shared meals. The thoughtful design extends to the

  Deana Renn AtCoastal Realty

  2100 Sanderson Rd, Chesapeake, VA 23322
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  /15

  $840,000

  • Land
  • 21 Acres
  • $40,000 per Acre

  4500 Backwoods Rd, Chesapeake, VA 23322

  Property is priced to reflect the updates needed and is being sold as-is, including all buildings. The property features a pond, a dwelling and acreage. Ideal opportunity for investors or developers seeking future upside, potential tax advantages with the City of Chesapeake, or a private estate setting. Conveniently located just minutes from Grassfield High School, shopping, I-64, and easy access

  Ashley McDougal Howard Hanna Real Estate Svcs.

  4500 Backwoods Rd, Chesapeake, VA 23322
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  /20

  $846,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 3,057 Sq Ft

  1924 Hungarian Rd, Chesapeake, VA 23322

  The Ambler by Kirbor Homes Highlights; Mudroom, large breakfast area adjacent to spacious kitchen. Great room big enough for multiple couches! Flex room down has options for office or bedroom deisgn. Second floor showcases HUGE primary bedroom that has not one but two walk in closets! The laundry is conveniently connected from the primary and the hallway. 3 additional bedrooms plus a loft that

  Deana Renn AtCoastal Realty

  1924 Hungarian Rd, Chesapeake, VA 23322
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  /3

  $279,900

  • Land
  • 3.79 Acres
  • $73,950 per Acre

  737 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

  737 Bedford St, Chesapeake, VA 23322
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  $999,900 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,424 Sq Ft

  MM Kh at Hungarian (Holden) Rd, Chesapeake, VA 23322

  Experience refined living with KH Signature—where elevated features come standard. This stunning home offers no HOA restrictions & is zoned A-1 for ultimate flexibility. The spacious primary suite is conveniently located on the first floor, complemented by a luxurious tile shower and stylish tile floors in all baths. Enjoy the charm of a wrapped porch & the durability of fiber cement siding

  Deana Renn AtCoastal Realty

  MM Kh at Hungarian (Holden) Rd, Chesapeake, VA 23322
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  /5

  $399,900

  • Land
  • 21.52 Acres
  • $18,584 per Acre

  15+AC Taft Rd, Chesapeake, VA 23322

  Your going to want to see this listing! Available acreage in the highly sought after Hickory and Grassfield school districts. This recently platted 21.581 acres of raw farm land is a rare find in southern Chesapeake. The property is not currently leased, but can be an option if desired. Property line adjustment of less than 1 acre to be done before closing. Buyer to do their due diligence on

  Gilbert Falk III EXP Realty LLC

  15+AC Taft Rd, Chesapeake, VA 23322
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  /24

  $1,100,000

  • 6 Beds
  • 3.5 Baths
  • 5,533 Sq Ft

  2325 Woodhurst Ln, Chesapeake, VA 23322

  Stunning all white brick custom-built colonial on 3.3 acres picturesque in sought after West Landing Estates. Circular driveway. Huge 5533 sqft of living space; hardwood floors;6 bedrooms;3 full and 1 half baths;2-car attached side entry garage;upgraded kitchen with granite countertop, wall ovens and stainless steel appliances. 3 zones heating/air conditioning heat pumps (5 years young). 3-car

  Norman Domingo XRealty.NET LLC

  2325 Woodhurst Ln, Chesapeake, VA 23322
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  /13

  $719,900 New Construction

  • 3 Beds
  • 2 Baths
  • 2,134 Sq Ft

  MM Fields at Taft (Squire Parcel A - 4) Rd, Chesapeake, VA 23322

  This sprawling ranch design by Kirbor Homes that seamlessly blends modern sophistication w/ the timeless appeal of single-level living. As sunlight streams through expansive windows, the open-air great room beckons—providing the a backdrop for lively game nights, cozy movie marathons or casual gatherings around the impressive 8-foot kitchen island. A well-appointed daily pantry and a separate

  Deana Renn AtCoastal Realty

  MM Fields at Taft (Squire Parcel A - 4) Rd, Chesapeake, VA 23322
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  /3

  $1,114,900 New Construction

  • 5 Beds
  • 3.5 Baths
  • 3,647 Sq Ft

  MM Kh at Hungarian (Caroline Design) Rd, Chesapeake, VA 23322

  Discover a home that truly has it all - The Caroline by KH Signature! Featuring a true wrap-around porch and the biggest primary closet you’ve ever seen, this home is designed for both style and function. The first-floor primary suite offers convenience and luxury, while top-of-the-line finishes elevate every detail. With construction-to-perm financing incentives, making your dream home a reality

  Deana Renn AtCoastal Realty

  MM Kh at Hungarian (Caroline Design) Rd, Chesapeake, VA 23322
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  /16

  $295,000

  • Land
  • 4.87 Acres
  • $60,575 per Acre

  3725 Cornland Rd, Chesapeake, VA 23322

  Centrally located...QUIET, SECLUDED LIVING on 4.87 ACRES IN THE COUNTRY PART OF CHESAPEAKE.Located off RT 17 near the “NORTH CAROLINA” line in a growing area. Less than 10 minutes to GREAT BRIDGE and minutes from I-64 for access to all S Hampton Roads and the Peninsula. PRIVACY, SPACE & LOCATION.*THE CITY OF CHESAPEAKE TAX RECORDS DOCUMENT LAND USE AS RESIDENTIAL ACREAGE. THIS IS A GOOD

  Ronda Galko Howard Hanna Real Estate Svcs.

  3725 Cornland Rd, Chesapeake, VA 23322
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  /50

  $1,650,000

  • 5 Beds
  • 4.5 Baths
  • 6,848 Sq Ft

  641 Ravenwoods Dr, Chesapeake, VA 23322

  Stunning property situated in the heart of Great Bridge on 3 acres! Brand new gourmet kitchen with 6 burner Cosmo range, additional prep sink, new top of the line appliances and custom cabinetry. All new paint, flooring and completely renovated baths and stairwells on first two primary living levels. Bonus third floor complete with full bath! HUGE primary suite complete with fireplace, fantastic

  Kelly Dipasquale Aweigh Real Estate

  641 Ravenwoods Dr, Chesapeake, VA 23322
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  /16

  $726,791 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,630 Sq Ft

  MM Fields at Taft (Kentland) Rd, Chesapeake, VA 23322

  Waking up in The Kentland every morning is an experience homeowners can cherish. The first rays of sunlight gently filter through the large windows, casting a warm glow across the spacious primary suite. The high ceilings create an airy atmosphere, allowing the day to begin with a sense of openness and tranquility. As you step into the luxurious open-concept great room, the carefully curated

  Deana Renn AtCoastal Realty

  MM Fields at Taft (Kentland) Rd, Chesapeake, VA 23322
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  /2

  $776,450 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,630 Sq Ft

  MM Sanderson Estates (Kentland Ph 26) Ct, Chesapeake, VA 23322

  Waking up in The Kentland every morning is an experience homeowners can cherish. As you step into the luxurious open-concept living area, the carefully curated interior design elements come to life, seamlessly blending modern aesthetics w/ timeless elegance. In the heart of the home lies the bustling kitchen—centered around the breakfast nook & the great room. The Kentland’s layout prioritizes

  Deana Renn AtCoastal Realty

  MM Sanderson Estates (Kentland Ph 26) Ct, Chesapeake, VA 23322
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  /35

  $450,000

  • Land
  • 5.95 Acres
  • $75,656 per Acre

  2212 Carolina Rd, Chesapeake, VA 23322

  HORSE FENCE IS ELECTRIC AND TURNED ON. We offer 5.948 acres to build your new home, enjoy your horses, spend time on your hobbies! There is a 50' x 100' metal warehouse which has a partial concrete pad, power and well. Easy to show. REIN lockbox on side door of warehouse. Feel that country breeze, smell that country air!

  Juanita Harris Waterway Realty

  2212 Carolina Rd, Chesapeake, VA 23322
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  /23

  $911,016 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,424 Sq Ft

  1517 Cedarville Rd, Chesapeake, VA 23322

  New Construction – Holden Model with a new front elevation on 1 Acre! Ready early 2026. This thoughtfully designed home features a main-level vaulted primary suite, @ 7 x 5 luxury tile shower in primary bath, chef’s kitchen with quartz countertops featuring a 36" cooktop, built in microwave, wall oven, and dishwasher, upgraded two tone cabinetry, butler’s pantry with open shelving, backsplash,

  Deana Renn AtCoastal Realty

  1517 Cedarville Rd, Chesapeake, VA 23322
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  /21

  $761,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 3,057 Sq Ft

  MM Fields at Taft (Ambler Parcel A-4) Rd, Chesapeake, VA 23322

  Wake up to expansive views! At the heart of the Ambler, you’ll find the kitchen, which curates a culinary haven where creativity knows no bounds. Picture this: a lazy Sunday morning, sunlight streams through the windows. As you sip on your morning coffee, the kids eagerly gather around the expansive center island, ready to lend a hand in preparing a delightful brunch. In the cozy great room,

  Deana Renn AtCoastal Realty

  MM Fields at Taft (Ambler Parcel A-4) Rd, Chesapeake, VA 23322
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  /3

  $877,500 New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,585 Sq Ft

  2116 Sanderson Rd, Chesapeake, VA 23322

  NEW DESIGN by Kirbor Homes. You have asked and we have answered! The Miles offers all the spaces in just the right places! Office and dining on first floor. Dining could be second office! Bedroom and full bath on the first floor. Mudroom with optional cubbies available. Powder room off garage for the quick break from running around this open 3 acres. Second floor has 3 secondary bedrooms. Two of

  Deana Renn AtCoastal Realty

  2116 Sanderson Rd, Chesapeake, VA 23322
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  /14

  $982,800

  • Land
  • 12.29 Acres
  • $80,000 per Acre

  1928 Moses Grandy Trail, Chesapeake, VA 23323

  Parcel A- residential lot on the waterway. Condemned home & small cemetery on premises. 12.285 ac in the heart of grassfield, perfect for building a home on a 15,000 sq foot lot and have privacy all around you. Parcels B,C & D are also available

  Carmon Pizzanello BHHS RW Towne Realty

  1928 Moses Grandy Trail, Chesapeake, VA 23323
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  /22

  $475,000

  • 3 Beds
  • 2.5 Baths
  • 1,873 Sq Ft

  501 Fernwood Farms Rd, Chesapeake, VA 23320

  Elegantly updated 3-bedroom, 2 1/2-bath residence spanning 1,873 sq ft of refined living space. The gourmet kitchen boasts brand-new cabinetry, gleaming granite countertops, and premium appliances including dishwasher, range, microwave, and disposal. Luxurious bathrooms feature new countertops, while the home showcases new floors, doors, windows, siding, and a modern water heater, all enhanced by

  Kris Weaver Atlantic Sothebys Int'l Realty

  501 Fernwood Farms Rd, Chesapeake, VA 23320
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  /26

  $1,156,900 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,936 Sq Ft

  MM Kh at Hungarian (Freemont On Lot 1) Rd, Chesapeake, VA 23322

  From the moment you step into The Freemont, sophistication greets you at every turn. A stately office welcomes you, while an elegant dining room sets the tone for memorable gatherings & celebrations. A breathtaking two-story great room provides natural light & open energy. The kitchen is a true showpiece, designed for both beauty & function. A wall of windows frames the kitchen sink ,while the

  Deana Renn AtCoastal Realty

  MM Kh at Hungarian (Freemont On Lot 1) Rd, Chesapeake, VA 23322
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  /2

  $190,000

  • Land
  • 1.38 Acres
  • $137,681 per Acre

  2701 Seven Eleven Rd, Chesapeake, VA 23322

  This is a wooded 1.38 acre lot along a lightly traveled road that's being gradually redeveloped. Survey in hand as well as a wetlands delineation report done in 2025 showing about 0.88 Acre of wetlands and about 0.50 Acre of non-wetlands towards the back of the lot.

  Craig Brinn Wainwright Real Estate

  2701 Seven Eleven Rd, Chesapeake, VA 23322
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  /15

  $290,000

  • Land
  • 7.4 Acres
  • $39,189 per Acre

  1813 Shillelagh Rd, Chesapeake, VA 23323

  Great opportunity to own approx 7.4 acres in Hickory! This city-approved building site has already been cleared and is ready for your dream home. All preliminary site work and necessary approvals are complete, to including surveying, engineered septic system with a successful perc test, wetlands mitigation, and full compliance with Corps of Engineers requirements. Bring the builder of your choice!

  Marco Rivas 757 Realty

  1813 Shillelagh 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 Svcs.

  8 Shillelagh Rd, Chesapeake, VA 23323
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  /4

  $399,900

  • Land
  • 20.05 Acres
  • $19,941 per Acre

  Lot C Buskey Rd, Chesapeake, VA 23322

  Your going to want to see this listing! Available acreage in the highly sought after Hickory and Grassfield school districts. This recently platted 20.054 acres of raw farm land is a rare find in southern Chesapeake. The property is not currently leased, but can be an option if desired. This parcel sits in the middle of two similar tracts of farm land on its southern and northern borders. Buyer

  Gilbert Falk III EXP Realty LLC

  Lot C Buskey Rd, Chesapeake, VA 23322
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  /21

  $125,000

  • Land
  • 2.5 Acres
  • $50,000 per Acre

  2.5 Ac Dismal Swamp Canal Trail, Chesapeake, VA 23322

  Seller would prefer to sell adjacent lot- (In MLS) together. Great opportunity to build 2 homes one on each lot.Very Private but easily accessible, as property is surrounded by protected land and unbuildable for long term security. Property is adjacent to the biking path on The Great Dismal Swamp. Great Hunting and outdoors enthusiast dream in your backyard, property backs to Dismal Swamp Tract

  Alexandra Serrano The Real Estate Group

  2.5 Ac Dismal Swamp Canal Trail, Chesapeake, VA 23322
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  /2

  $260,000

  • Land
  • 5.33 Acres
  • $48,808 per Acre

  B Taft Rd, Chesapeake, VA 23322

  Vacant cleared lot, road access via access easement via lot 1 adjacent to Taft road

  Tom Thrasher Greenbrier Real Estate & Appr.

  B Taft Rd, Chesapeake, VA 23322
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  /50

  $1,299,000

  • 6 Beds
  • 5 Baths
  • 4,726 Sq Ft

  2700 Ballahack Rd, Chesapeake, VA 23322

  Welcome to this stunning 6-bedroom, 5-bath, 4,726 sq ft brick estate set on nearly 6 acres of serene countryside. This two-story residence offers an amazing blend of luxury, comfort, and functionality. Inside, you’ll find expansive living spaces, a well-appointed kitchen, and generously sized bedrooms designed for both privacy and togetherness. The home is ideal for entertaining, featuring an

  Eric Edwards Iron Valley Real Est. Prestige

  2700 Ballahack Rd, Chesapeake, VA 23322
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  /4

  $699,000

  • Land
  • 97.9 Acres
  • $7,140 per Acre

  2237 Shillelagh Rd, Chesapeake, VA 23323

  Vacant land on Shillelagh Rd in a country setting that spans over 97.9 acres. Build a home and enjoy the wildlife and foliage. Great location and School District. Quick access to Dominion Blvd to the I-64 to Downtown Norfolk, NPN, Hampton and the MM-Tunnel and Military Bases. Go south to Benefit Rd and a short drive to the Outer Banks to NC and 40 minutes to the Virginia Beach Oceanfront or the

  Corinne Zedd The Real Estate Group

  2237 Shillelagh Rd, Chesapeake, VA 23323
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  /6

  $399,900

  • Land
  • 18.9 Acres
  • $21,156 per Acre

  Lot B Buskey Rd, Chesapeake, VA 23322

  Your going to want to see this listing! Available acreage in the highly sought after Hickory and Grassfield school districts. This recently platted 18.902 acres of raw farm and timber land is a rare find in southern Chesapeake. The property is not currently leased, but can be an option if desired. This parcel has two small ponds and a small amount of bottom lands on it's southern border. Buyer to

  Gilbert Falk III EXP Realty LLC

  Lot B Buskey Rd, Chesapeake, VA 23322
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  /3

  $279,900

  • Land
  • 3.77 Acres
  • $74,323 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
• 

  

  /48

  $874,900

  • 5 Beds
  • 3 Baths
  • 2,880 Sq Ft

  2532 Wild Horse Ridge, Chesapeake, VA 23322

  Private, end-of-cul-de-sac 46.43-acre retreat in the sought-after Grassfield HS district, mix of timber & open fields with room for horses, ATVs, hunting & more. Surrounding trails, deer & wild turkey make this a true sportsman’s paradise and shopping. Built in 2021, the bright ranch offers an open Kitchen/Living/Dining plan, large bedrooms, generous closets, big utility/mud room, and a primary

  Jose Hernandez Keller Williams Realty Twn Ctr

  2532 Wild Horse Ridge, Chesapeake, VA 23322
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  /50

  $3,950,000

  • 5 Beds
  • 7.5 Baths
  • 8,000 Sq Ft

  4112 Mingo Trail, Chesapeake, VA 23325

  A deep-water luxury retreat, privately gated and designed for those who value privacy,quality and exceptional waterfront living. This remarkable estate offers quick bay accesswith three high-speed boat lifts, water views, and manicured groundsaccented by extensive paver hardscapes. Thoughtfully constructed with intention anddurability, the home features a grand living room with

  Debbie Rountree BHHS RW Towne Realty

  4112 Mingo Trail, Chesapeake, VA 23325
• 

  /2

  $851,282 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,141 Sq Ft

  1525 Cedarville Rd, Chesapeake, VA 23322

  The Lee floor plan redefines the concept of versatile living. An expansive formal entryway sets the stage for formal living in a relaxed environment. The large living areas invite you to create memories w/ your loved ones. Imagine starting your day in the stunning primary bedroom on the first level as the sun slowly rises, casting a warm glow across the room. The morning routine becomes a serene

  Deana Renn AtCoastal Realty

  1525 Cedarville Rd, Chesapeake, VA 23322
• 

  

  /3

  $279,900

  • Land
  • 4.05 Acres
  • $69,077 per Acre

  749 Bedford St, Chesapeake, VA 23322

  This is a 4 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 Build

  Robert Wadsworth Pungo Realty LLC

  749 Bedford St, Chesapeake, VA 23322

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