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$2,425,000
10634546 MLS
Escape the ordinary with this expansive 25.84-acre parcel located in the highly sought-after Western Branch area of Chesapeake. This rare offering provides a unique blend of privacy, natural beauty, and strategic location, making it an ideal canvas for a private estate, a boutique residential development, or a long-term land investment. Subject to local zoning, the size and location of this tract present significant opportunities for residential growth in a high-demand corridor. Nestled in the heart of Western Branch, known for its strong community feel, excellent school districts, and convenient access to the Hampton Roads region.

25+AC S Military Highway, Central Chesapeake
$7,334
10632409 MLS
Exciting investment opportunity in the Hillcrest neighborhood. One of the largest assemblages of lots in the neighborhood touting 15 parcels total with one being a double that can be resubdivided. Lots range from .22-.46 acres per tax records combined totaling 3.68ac +/- . Lots are located between Binford, Trinkle, and Caddie streets with only two located on the other side of Caddie on the corner. 400 feet from the end of the paved section of Trinkle street you will hit the first lot to the assemblage on your left. The paper street section of Trinkle is accessible and has ditches on both sides. Come take a walk through the massive oaks located on the property, nice open woods, truly a beautiful collection of lots to make your own, hold for an investment, urban archery hunt, or buy and re sell in parts for cash flow. All 15 parcels to be sold together.

19-20 Caddie Street, South Chesapeake
$7,334
10632400 MLS
Exciting investment opportunity in the Hillcrest neighborhood. One of the largest assemblages of lots in the neighborhood touting 15 parcels total with one being a double that can be resubdivided. Lots range from .22-.46 acres per tax records combined totaling 3.68ac +/- . Lots are located between Binford, Trinkle, and Caddie streets with only two located on the other side of Caddie on the corner. 400 feet from the end of the paved section of Trinkle street you will hit the first lot to the assemblage on your left. The paper street section of Trinkle is accessible and has ditches on both sides. Come take a walk through the massive oaks located on the property, nice open woods, truly a beautiful collection of lots to make your own, hold for an investment, urban archery hunt, or buy and re sell in parts for cash flow. All 15 parcels to be sold together.

Lot 38 Trinkle Street, South Chesapeake
$7,334
10632393 MLS
Exciting investment opportunity in the Hillcrest neighborhood. One of the largest assemblages of lots in the neighborhood touting 15 parcels total with one being a double that can be resubdivided. Lots range from .22-.46 acres per tax records combined totaling 3.68ac +/- . Lots are located between Binford, Trinkle, and Caddie streets with only two located on the other side of Caddie on the corner. 400 feet from the end of the paved section of Trinkle street you will hit the first lot to the assemblage on your left. The paper street section of Trinkle is accessible and has ditches on both sides. Come take a walk through the massive oaks located on the property, nice open woods, truly a beautiful collection of lots to make your own, hold for an investment, urban archery hunt, or buy and re sell in parts for cash flow. All 15 parcels to be sold together.

39 Trinkle Street, South Chesapeake
$7,334
10632385 MLS
Exciting investment opportunity in the Hillcrest neighborhood. One of the largest assemblages of lots in the neighborhood touting 15 parcels total with one being a double that can be resubdivided. Lots range from .22-.46 acres per tax records combined totaling 3.68ac +/- . Lots are located between Binford, Trinkle, and Caddie streets with only two located on the other side of Caddie on the corner. 400 feet from the end of the paved section of Trinkle street you will hit the first lot to the assemblage on your left. The paper street section of Trinkle is accessible and has ditches on both sides. Come take a walk through the massive oaks located on the property, nice open woods, truly a beautiful collection of lots to make your own, hold for an investment, urban archery hunt, or buy and re sell in parts for cash flow. All 15 parcels to be sold together.

Lot 37 Trinkle Street, South Chesapeake
$7,334
10632384 MLS
Exciting investment opportunity in the Hillcrest neighborhood. One of the largest assemblages of lots in the neighborhood touting 15 parcels total with one being a double that can be resubdivided. Lots range from .22-.46 acres per tax records combined totaling 3.68ac +/- . Lots are located between Binford, Trinkle, and Caddie streets with only two located on the other side of Caddie on the corner. 400 feet from the end of the paved section of Trinkle street you will hit the first lot to the assemblage on your left. The paper street section of Trinkle is accessible and has ditches on both sides. Come take a walk through the massive oaks located on the property, nice open woods, truly a beautiful collection of lots to make your own, hold for an investment, urban archery hunt, or buy and re sell in parts for cash flow. All 15 parcels to be sold together.

36 Trinkle Street, South Chesapeake
$7,334
10632383 MLS
Exciting investment opportunity in the Hillcrest neighborhood. One of the largest assemblages of lots in the neighborhood touting 15 parcels total with one being a double that can be resubdivided. Lots range from .22-.46 acres per tax records combined totaling 3.68ac +/- . Lots are located between Binford, Trinkle, and Caddie streets with only two located on the other side of Caddie on the corner. 400 feet from the end of the paved section of Trinkle street you will hit the first lot to the assemblage on your left. The paper street section of Trinkle is accessible and has ditches on both sides. Come take a walk through the massive oaks located on the property, nice open woods, truly a beautiful collection of lots to make your own, hold for an investment, urban archery hunt, or buy and re sell in parts for cash flow. All 15 parcels to be sold together.

15 Binford Street, South Chesapeake
$7,334
10632374 MLS
Exciting investment opportunity in the Hillcrest neighborhood. One of the largest assemblages of lots in the neighborhood touting 15 parcels total with one being a double that can be resubdivided. Lots range from .22-.46 acres per tax records combined totaling 3.68ac +/- . Lots are located between Binford, Trinkle, and Caddie streets with only two located on the other side of Caddie on the corner. 400 feet from the end of the paved section of Trinkle street you will hit the first lot to the assemblage on your left. The paper street section of Trinkle is accessible and has ditches on both sides. Come take a walk through the massive oaks located on the property, nice open woods, truly a beautiful collection of lots to make your own, hold for an investment, urban archery hunt, or buy and re sell in parts for cash flow. All 15 parcels to be sold together.

34 Trinkle Street, South Chesapeake
$7,334
10632328 MLS
Exciting investment opportunity in the Hillcrest neighborhood. One of the largest assemblages of lots in the neighborhood touting 15 parcels total with one being a double that can be resubdivided. Lots range from .22-.46 acres per tax records combined totaling 3.68ac +/- . Lots are located between Binford, Trinkle, and Caddie streets with only two located on the other side of Caddie on the corner. 400 feet from the end of the paved section of Trinkle street you will hit the first lot to the assemblage on your left. The paper street section of Trinkle is accessible and has ditches on both sides. Come take a walk through the massive oaks located on the property, nice open woods, truly a beautiful collection of lots to make your own, hold for an investment, urban archery hunt, or buy and re sell in parts for cash flow. All 15 parcels to be sold together.

Lot 33 Trinkle Street, South Chesapeake
$7,334
10632319 MLS
Exciting investment opportunity in the Hillcrest neighborhood. One of the largest assemblages of lots in the neighborhood touting 15 parcels total with one being a double that can be resubdivided. Lots range from .22-.46 acres per tax records combined totaling 3.68ac +/- . Lots are located between Binford, Trinkle, and Caddie streets with only two located on the other side of Caddie on the corner. 400 feet from the end of the paved section of Trinkle street you will hit the first lot to the assemblage on your left. The paper street section of Trinkle is accessible and has ditches on both sides. Come take a walk through the massive oaks located on the property, nice open woods, truly a beautiful collection of lots to make your own, hold for an investment, urban archery hunt, or buy and re sell in parts for cash flow. All 15 parcels to be sold together.

Lot 40 Caddie Street, South Chesapeake
$7,334
10632316 MLS
Exciting investment opportunity in the Hillcrest neighborhood. One of the largest assemblages of lots in the neighborhood touting 15 parcels total with one being a double that can be resubdivided. Lots range from .22-.46 acres per tax records combined totaling 3.68ac +/- . Lots are located between Binford, Trinkle, and Caddie streets with only two located on the other side of Caddie on the corner. 400 feet from the end of the paved section of Trinkle street you will hit the first lot to the assemblage on your left. The paper street section of Trinkle is accessible and has ditches on both sides. Come take a walk through the massive oaks located on the property, nice open woods, truly a beautiful collection of lots to make your own, hold for an investment, urban archery hunt, or buy and re sell in parts for cash flow. All 15 parcels to be sold together.

Lot 35 Trinkle Street, South Chesapeake
$7,334
10632289 MLS
Exciting investment opportunity in the Hillcrest neighborhood. One of the largest assemblages of lots in the neighborhood touting 15 parcels total with one being a double that can be resubdivided. Lots range from .22-.46 acres per tax records combined totaling 3.68ac +/- . Lots are located between Binford, Trinkle, and Caddie streets with only two located on the other side of Caddie on the corner. 400 feet from the end of the paved section of Trinkle street you will hit the first lot to the assemblage on your left. The paper street section of Trinkle is accessible and has ditches on both sides. Come take a walk through the massive oaks located on the property, nice open woods, truly a beautiful collection of lots to make your own, hold for an investment, urban archery hunt, or buy and re sell in parts for cash flow. All 15 parcels to be sold together.

Lot 18 Binford Street, South Chesapeake
$7,334
10632283 MLS
Exciting investment opportunity in the Hillcrest neighborhood. One of the largest assemblages of lots in the neighborhood touting 15 parcels total with one being a double that can be resubdivided. Lots range from .22-.46 acres per tax records combined totaling 3.68ac +/- . Lots are located between Binford, Trinkle, and Caddie streets with only two located on the other side of Caddie on the corner. 400 feet from the end of the paved section of Trinkle street you will hit the first lot to the assemblage on your left. The paper street section of Trinkle is accessible and has ditches on both sides. Come take a walk through the massive oaks located on the property, nice open woods, truly a beautiful collection of lots to make your own, hold for an investment, urban archery hunt, or buy and re sell in parts for cash flow. All 15 parcels to be sold together.

Lot 17 Binford Street, South Chesapeake
$7,334
10632275 MLS
Exciting investment opportunity in the Hillcrest neighborhood. One of the largest assemblages of lots in the neighborhood touting 15 parcels total with one being a double that can be resubdivided. Lots range from .22-.46 acres per tax records combined totaling 3.68ac +/- . Lots are located between Binford, Trinkle, and Caddie streets with only two located on the other side of Caddie on the corner. 400 feet from the end of the paved section of Trinkle street you will hit the first lot to the assemblage on your left. The paper street section of Trinkle is accessible and has ditches on both sides. Come take a walk through the massive oaks located on the property, nice open woods, truly a beautiful collection of lots to make your own, hold for an investment, urban archery hunt, or buy and re sell in parts for cash flow. All 15 parcels to be sold together.

Lot 16 Binford Street, South Chesapeake
$70,000
10628741 MLS
Prime opportunity in Chesapeake’s South Norfolk/Money Point area! This vacant parcel is zoned M-2 (Heavy Industrial), offering excellent potential for a wide range of commercial or industrial uses. The lot is approx. 3,920 sq ft and ideally positioned with convenient access to major thoroughfares, interstates, and the Port of Virginia.The value here is in the land and its flexible zoning, making it a strong fit for investors, business owners, or developers looking for a strategic location with room to grow. Whether for storage, contractor use, or future development, this property presents multiple paths to maximize value.Opportunities like this in a well-connected industrial corridor are limited—don’t miss your chance to secure a versatile piece of land in a high-demand area.

435 Freeman Avenue, Central Chesapeake
$250,000
10628255 MLS
Excellent building opportunity. Great location. Surrounded by several custom built homes. Very private and priced below market.

2716 Seven Eleven Road, South Chesapeake
$2,200,000
10625643 MLS
Exceptional 118 acre investment opportunity in southern Chesapeake, offering approximately 91 acres of open, cleared land and nearly 2,000 feet of frontage along West Rd. This is a rare assemblage of five contiguous tracts all ranging from 23–24 acres. It presents outstanding development and long term investment potential. A scenic blend of productive cropland and mature timber provides natural beauty, privacy, and abundant wildlife. Located in sought after school districts, the property delivers a peaceful country setting with the convenience of easy access to all of Hampton Roads.

118Ac West Road, South Chesapeake
$75,000
10624642 MLS
This is a great opportunity to build on lots in Chesapeake's South Norfolk. The two lots are side by side with residential homes beside them. Both lots are zoned B1 and the area lot is 5,576 square feet. Lots require rezoning at buyers cost to possibly build one residential home or a duplex. Dimensions are 124 X 40 X 123 X 40.

1427 Atlantic Avenue, Central Chesapeake
$275,000
10623777 MLS
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, SECLUDED LOCATION. THE CITY OF CHESAPEAKE TAX RECORDS DOCUMENT LAND USE AS RESIDENTIAL ACREAGE. THIS IS A GOOD TIME TO PURCHASE AND BUILD.

3725 Cornland Road, South Chesapeake
$1,704,000
10621427 MLS
An amazing investment opportunity awaits. Beautiful and pristine country property nestled in the heart of Chesapeake. Located just minutes from the Chesapeake Municipal Center and the Chesapeake Expressway. Aforementioned property has a easy access to the Beaches of the Outer Banks along with shopping and fine dining in surrounding cities. This farm has approximately 40 acres of hardwoods and pines along with nearly 105 acres of cultivated agriculture fields. The entrance on the farm is 100' feet wide and 431' deep. Imagine watching the pristine sunsets over beautifully fenced horse pastures or the endless amounts of wild turkeys and deer traversing the landscape. The possibilities for this farm are vast and endless. Wonderful opportunity to design your own family compound, develop a gentleman's farm or equestrian facility. This property is also with in minutes of Bobs Fishing Hole Marina for a quick commute to Tulls Bay, Currituck Sound and the Intra Coastal Waterway.

556 B Gallbush Road, South Chesapeake
$669,900
10621269 MLS
Vacant Land on Shillelagh Rd in a country setting that spans over 97.9 acres. Building on the property is used for the Hunt Club. 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 Virginia Beach Oceanfront or the Chesapeake Bay. Access to the property through the locked front gate. Call for access.

2237 Shillelagh Road, South Chesapeake
$750,000
10620473 MLS
SURVEYED, BUILDABLE BOTH PROPERTIES TO BE SOLD TOGETHER, TOTAL 7.4 AC+OR- RECENTLY SURVEYED BUIDABLE LEGAL DESCRIPTION FOR EACH PROPERTY NECK ROAD 4.352 AC, NECK ROAD 2.85 AC CHECK WITH CITY IF THINKING OF HAVING REZONED TO COMMERCIAL, ONE PROPERTY ON NORTH SIDE OF MOSSES GRANDY TRAIL OTHER ON SOUTH SIDE OF MOSES GRANDY TRAIL, BOTH DIRECTLY ACROSS FROM EACH OTHER, SURVEY IN DOCUMENTS

7.4 AC Moses Grandy Trail, South Chesapeake
$434,900
10620048 MLS
Your going to want to see this listing! Available acreage in the highly sought after Hickory and Grassfield school districts. This recently platted 27.232 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 is the largest of four and is Lot D on the plat. Buyer to do their due diligence on well, septic, and building permit. Call the listing agent for a showing today!

Lot D Buskey Road, South Chesapeake
$239,900
10619809 MLS
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 Build to Suit lease package deals also. Call/text agent for more information.

743 Bedford Street, South Chesapeake
$295,000
10618662 MLS
LIST PRICE SIGNIFICANTLY UNDER TAX VALUE-Imagine owning a little over 22 acres of beautifully wooded agricultural land where privacy, nature, and possibility come together. This expansive parcel offers an ideal backdrop for creating your own homestead, with plenty of room for a homesite, gardens, animals, or a self sufficient lifestyle. Mature trees provide natural beauty and seclusion, making this property feel like a true retreat. Whether you dream of homesteading, farming, recreation, or holding land for the future, this is a rare opportunity to own a sizable piece of peaceful countryside right on the VA/NC border.

15.+AC Johnson Lane, South Chesapeake
$125,000
10617958 MLS
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 of Cavalier Wildlife Management Area. Each lot is ~2.5 acres. Drive by to view. Wetlands study and Topo Survey in Docs. City confirmed both lots buildable and legally accessible. Also, good opportunity for tree farm lease and harvesting, never logged before. Utilities are starting to go in on new road in front of property. These properties do not come up for sale often. Call for more information and a private showing! Take George Washington HWY to Cornland Rd, Cornland dead ends to Dismal Swamp Trail, turn right and lots are on the right hand side.

2.5 Ac Dismal Swamp Canal Trail, South Chesapeake
$125,000
10617956 MLS
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 of Cavalier Wildlife Management Area. Each lot is ~2.5 acres. Drive by to view. Wetlands study and Topo Survey in Docs. City confirmed both lots buildable and legally accessible. Also, good opportunity for tree farm lease and harvesting, never logged before. Utilities are starting to go in on new road in front of property. These properties do not come up for sale often. Call for more information and a private showing! Take George Washington HWY to Cornland Rd, Cornland dead ends to Dismal Swamp Trail, turn right and lots are on the right hand side.

2.5 Ac Dismal Swamp Canal Trail, South Chesapeake
$840,000
10614351 MLS
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 to Moyock, NC.

4500 Backwoods Road, South Chesapeake
$240,000
10608068 MLS
Vacant cleared lot, road access via access easement via lot 1 adjacent to Taft road

B Taft Road, South Chesapeake
$95,000
10607003 MLS
Prime opportunity in Chesapeake’s South Norfolk/Money Point area! This property is zoned M-2 (Heavy Industrial), offering excellent potential for commercial or industrial use. The parcel is approx. 3,572 sq ft and well-situated with convenient access to major thoroughfares, ports, and interstates.Onsite is a 2-bedroom, 1-bath home (approx. 1,016 sq ft) that can provide immediate rental income, office space, or temporary use while future plans are developed. The structure is a bonus, but the true value lies in the land and its versatile zoning, making this a rare find for investors, business owners, or developers seeking expansion opportunities.Capitalize on a location with strong growth, flexible uses, and multiple options for maximizing value.

427 Freeman Avenue, Central Chesapeake

Some listings may be duplicated in the search results due to the co-mingling of listings from more than one multiple listing service. Should there be different listing information between the duplicated listings; user is advised to verify the accuracy of the listing information before making any financial decisions.