Chesapeake, VA Homes for Sale with Acreage

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  $739,000

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

  1517 Lookout Ct, Chesapeake, VA 23323

  Nestled on a peaceful 5-acre lot in the desirable Grassfield area, this beautiful 4-bedroom, 2.5-bath home offers the perfect mix of luxury, comfort, and outdoor space. Inside, you'll find a gorgeous eat-in kitchen with shiny marble countertops, an 8-foot island, and a high-quality double oven gas range, ideal for both everyday meals and entertaining. The two living areas are improved by

  

  Barbora Jerabek

  BHHS RW Towne Realty

  (757) 863-4250

  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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  /3

  $734,500

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

  MM Cedarville (Kentland Phase 25) Rd, 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 Cedarville (Kentland Phase 25) Rd, Chesapeake, VA 23322
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  $693,000 New Construction

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

  2430 Ballahack Rd, Chesapeake, VA 23322

  NEW CONSTRUCTION TO BE BUILT! 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

  Rachael Kraft Turner GreenTree Realty Inc

  2430 Ballahack Rd, Chesapeake, VA 23322
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  /35

  $756,350

  • 4 Beds
  • 3.5 Baths
  • 3,004 Sq Ft

  MM Cedarville (Lee Phase 25) Ct, Chesapeake, VA 23322

  Discover over an acres of possibilities! The popular Lee model by Kirbor Homes offers modern comfort with endless customization—choose your colors, layout, and finishes to design a home that fits your lifestyle. Add a 3rd car garage, oversized walk-in pantry, covered porch or sunroom, extended primary suite, walk-out attic, or even a second primary suite. Additional bedrooms and baths available

  Deana Renn AtCoastal Realty

  MM Cedarville (Lee Phase 25) Ct, Chesapeake, VA 23322
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  $287,000

  • 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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  /2

  $289,900

  • Land
  • 3.77 Acres
  • $76,978 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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  /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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  $689,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,053 Sq Ft

  MM Cedarville (Litton Parcel 25) Ct, Chesapeake, VA 23322

  One acre homesites on a culdesac are now recorded & selling! The Litton by Kirbor Homes is the epitome of cozy living. Each day, wake up slowly in the primary bedroom—sanctuary of comfort for homeowners where rest & rejuvenation await. When you’re ready, enjoy your cup of coffee & breakfast in the large open-concept living area where morning conversations w/ your loved ones prepare you for the

  Deana Renn AtCoastal Realty

  MM Cedarville (Litton Parcel 25) Ct, Chesapeake, VA 23322
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  $700,000

  • 6 Beds
  • 3.5 Baths
  • 2,802 Sq Ft

  3504 Old Mill Rd, Chesapeake, VA 23323

  Near-NEW construction! From the foundation on up, this one-of-a-kind ranch is as new construction as can be without obtaining the label. Multi-Generational Living possible with TWO bedrooms having ensuite baths -- the Large Primary features double sinks in the bath, a 60 SqFt walk-in closet, and direct access to the deck. Spacious kitchen with plenty of cabinets & countertop space; open living

  Angela Kennedy 1st Class RealEstate Integrity

  3504 Old Mill Rd, Chesapeake, VA 23323
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  /3

  $289,900

  • Land
  • 3.79 Acres
  • $76,592 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 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 Hungarian (Holden) Rd, Chesapeake, VA 23322
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  /13

  $719,900 New Construction

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

  MM 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 Taft (Squire Parcel A - 4) Rd, Chesapeake, VA 23322
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  $461,999

  • 4 Beds
  • 2.5 Baths
  • 2,353 Sq Ft

  4944 Clifton St, Chesapeake, VA 23321

  Located in desirable Chesapeake, Virginia, this spacious 4 bedroom, 2.5 bath home offers comfort, style, and convenience. Situated on a generous 1.4-acre corner lot with quick access to the highway, the property features a two-car garage plus an additional garage/shed in the backyard for extra storage or workspace. Inside, enjoy granite countertops, durable LVP flooring, and two inviting

  Cole Landry Creed Realty

  4944 Clifton St, Chesapeake, VA 23321
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  $1,595,000

  • 6 Beds
  • 5.5 Baths
  • 6,400 Sq Ft

  2652 Benefit Rd, Chesapeake, VA 23322

  Nestled in the heart of Hickory, this one-of-a-kind equestrian estate offers the perfect fusion of historic charm and modern luxury. The fully renovated main home features structural upgrades, 2017 roof, updated electrical (2025), plumbing, HVAC, insulation, and energy-efficient windows. Enjoy marble bathrooms, custom kitchen with Wolf range, Cafe; appliances, marble counters, and brand new white

  Andrew Christie Atlantic Sothebys Int'l Realty

  2652 Benefit Rd, Chesapeake, VA 23322
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  /3

  $1,114,900 New Construction

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

  MM 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 Hungarian (Caroline Design) Rd, Chesapeake, VA 23322
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  $934,900 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,553 Sq Ft

  1648 Sanderson Rd, Chesapeake, VA 23322

  MOVE IN READY! Looking for a inlaw suite that's set up like an apartment with its own entrance?? This is it!! No inlaw? No worries! This space can be used for a first floor guest bedroom, office, rec room, second entertaining room, or a gym! But can we talk about the size of the primary suite on the second floor? SPACIOUS is an understament. Dual vanities, large shower, free-standing soaking tub,

  Deana Renn AtCoastal Realty

  1648 Sanderson Rd, Chesapeake, VA 23322
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  $799,900

  • 3 Beds
  • 2.5 Baths
  • 2,367 Sq Ft

  1641 Shillelagh Rd, Chesapeake, VA 23323

  Incredible opportunity for 17+ acre Horse Farm. 2 barns, indoor riding arena, 2 outdoor rings, 3 pastures. Out buildings have separate electricity and wells. Total 28 stalls with 8 stalls near the home. Unique farmhouse with 3 generous bedrooms and large sunroom. The property is beautiful with the back acres predominantly wooded. Sold "as is". Make an appointment to see this horse lover's dream!

  Carol Hall BHHS RW Towne Realty

  1641 Shillelagh Rd, Chesapeake, VA 23323
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  $595,000 Open Thu 11AM - 1PM

  • 4 Beds
  • 2.5 Baths
  • 2,016 Sq Ft

  2841 Bunch Walnuts Rd, Chesapeake, VA 23322

  Welcome to this charming farmhouse style home featuring 4 bedrooms, 2.5 baths and just under 2100 square feet with modern updates, fresh paint, and professionally cleaned. Major systems and appliances were updated in 2019, including the roof, water heater, HVAC system, water softener, and remaining appliances, offering long-term reliability and reduced future expenses. Additional recent

  Rachael Norman COVA Home Realty

  2841 Bunch Walnuts 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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  $599,000

  • 3 Beds
  • 2 Baths
  • 1,703 Sq Ft

  381 Etheridge Rd, Chesapeake, VA 23322

  Home is 1 family owned. All brick ranch. Very well maintained. Roof recently replaced. Has a complete crawl space and termite inspection report with absolutely no issues to report. Approx. 4-1/2 ac. of very well maintained usable property. So beautiful and so much potential for the ability to add onto primary home, add extra garages and storage bldgs. and still have gardening and play area for

  Porter Young Wainwright Real Estate

  381 Etheridge Rd, Chesapeake, VA 23322
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  $669,000 New Construction

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

  2116 Cedar Rd, Chesapeake, VA 23323

  Rare find on Cedar Road! This new construction, multi-generational 5-bed, 3-bath home features two primary bedrooms, one conveniently located downstairs and a larger one upstairs great for extended family, aging parents, guests, or flexible living needs. Designed with an Open Living Format, the kitchen, dining, and great room flow seamlessly together, creating an effortless entertaining space.

  Marc Hrisko EXP Realty LLC

  2116 Cedar Rd, Chesapeake, VA 23323
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  /17

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,728 Sq Ft

  5533 Willow Lake Rd, Chesapeake, VA 23321

  Unique Opportunity in Western Branch, Chesapeake, Discover a rare opportunity to own a piece of land in the tranquil setting of Western Branch, Chesapeake. Nestled on a quiet dead-end street, this property is surrounded by beautiful wildlife, providing a serene atmosphere for nature lovers. The lot features a detached garage next to the house and a spacious barn in the back, complete with large

  Kelly Ayers Keller Williams Realty Twn Ctr

  5533 Willow Lake Rd, Chesapeake, VA 23321
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  /16

  $726,791 New Construction

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

  MM 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 Taft (Kentland) Rd, Chesapeake, VA 23322
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  /6

  $999,000

  • 3 Beds
  • 1 Bath

  3016 Cedarville Rd, Chesapeake, VA 23322

  Two parcels of cleared land Zoned A-1 totaling over 37 acres with 604.83 feet on Cedarville Road in the Hickory area of Chesapeake. The front lot with 21.67 acres. The back lot with 15.87 acres. Listing Agent is the managing partner of the ownership LLC. Must request appointment to see the property and provide a 24-hour notice. Contact the Listing Agent to schedule your appointment.

  Cindy Beall Harbor Associates Real Estate

  3016 Cedarville Rd, Chesapeake, VA 23322
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  /2

  $776,450

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

  MM Cedarville (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 Cedarville (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 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 Taft (Ambler Parcel A-4) Rd, Chesapeake, VA 23322
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  $849,900 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,098 Sq Ft

  1248 Jolliff Rd, Chesapeake, VA 23321

  BE HOME FOR THE HOLIDAYS! 5% INTEREST RATE AVAILABLE! MOVE-IN READY & PACKED WITH UPGRADES! Beloved Lee sits on 2.9 acres & is loaded with extensive list of included features that stand far above the standard. Highlights You’ll Love: 3-Car Garage with rear access door, 1st-Floor Primary Suite w/ cozy sitting room, large walk-in closet, spa-style bath w/ freestanding tub & oversized walk-in

  Deana Renn AtCoastal Realty

  1248 Jolliff Rd, Chesapeake, VA 23321
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  $1,400,000

  • 6 Beds
  • 5.5 Baths
  • 5,948 Sq Ft

  1445 Paul Eason Dr, Chesapeake, VA 23322

  Welcome to this stunning new listing in Hunters Ridge South! Located at 1445 Paul Eason Drive in Chesapeake, this elegant 6-bedroom, 5.5-bath home offers nearly 6,000 sq ft of luxury living in top-rated school districts. Step into a grand 2-story center hall that sets the tone for the home’s sophistication. Enjoy spacious living areas, dramatic tray and cathedral ceilings, dual-entry bath, gas

  Betsy Thompson The Agency

  1445 Paul Eason Dr, Chesapeake, VA 23322
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  $893,182 New Construction

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

  1501 Cedarville Rd, Chesapeake, VA 23322

  NOW INCLUDES NEW "D" ELEVATION! Live in a Lee model by Kirbor Homes on a rare 1-acre cul-de-sac homesite! Stunning home includes 1st flr primary suite with freestanding tub, luxurious tile walls with niche over fiberglass pan in primary bath, water closet, & huge walk-in + sitting room extension! Open concept perfect for cozy nights or entertaining guests. Upstairs features loft, 3 bedrooms (one

  Deana Renn AtCoastal Realty

  1501 Cedarville 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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  $1,156,900 New Construction

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

  MM 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 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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  /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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  /2

  $875,000

  • Land
  • 55 Acres
  • $15,909 per Acre

  55+AC Benefit Rd, Chesapeake, VA 23322

  Stunning property with mature trees and a lake. Pole barn as is. Survey available upon request.

  Elizabeth Stuart The Real Estate Group

  55+AC Benefit Rd, 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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  /43

  $1,375,000

  • 6 Beds
  • 5.5 Baths
  • 5,619 Sq Ft

  307 Hickory Station Dr, Chesapeake, VA 23322

  Welcome to your private oasis in Hickory! This single-owner property spans over 5500sqft between the main home and the detached addition and sits on a massive 3-acre lot. Beautiful crepe myrtles line the driveway as you enter and the exquisite landscaping guides you into the home's warm and inviting landscapes. Expert craftsmanship is apparent in the details as soon as you walk through the front

  Garrett Williams The Real Estate Group

  307 Hickory Station Dr, Chesapeake, VA 23322

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