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$1,325,000
5 Beds ⋅ 3.1 Baths ⋅ 10620633 MLS
Two homes. Endless possibilities. Tucked away on a 1.5-acre lot in the heart of Great Bridge, this rare property offers 5,633 SF across two beautifully updated homes great for multigenerational living, extended family, a home business, or potential rental income. The main home features 5 bedrooms, 3.5 baths, and a stunning kitchen with GE Café appliances, slate countertops, hand-painted cabinetry, reclaimed wood accents, and a custom bourbon bar great for entertaining. The detached guest house lives like its own residence with 2 bedrooms, 2 baths, an office, and a 2-car garage. Enjoy a backyard retreat with a 35,000-gallon saltwater pool, new decking, screened porch, and lush landscaping. Tankless water heaters and a whole-house generator add peace of mind. Located in the sought-after Great Bridge school district.

1149 Waters Road, 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, Chesapeake
$5,625,000
10620196 MLS
Sunnybrook Apartments (824 Post Ave and 2127 Chesapeake Drive, Chesapeake, VA) is a 48-unit multifamily community in the Hampton Roads metro, positioned for cash flow and upside. The property offers an attractive unit mix of forty-four (44) 2BR/1BA and four (4) 1BR/1BA apartments, supporting broad renter demand. Offered at a $5,625,000 list price, buyers may benefit from assumable financing of approximately $3.5M at 5.7% interest (subject to lender approval), helping reduce interest-rate uncertainty and enhance leverage. The Chesapeake location provides convenient access to retail, dining and commuter routes. A compelling value-add story exists through rent optimization, interior upgrades and operational efficiencies as units turn. Ideal for 1031 exchange or portfolio expansion. Contact broker for offering memorandum, rent roll and financials. Tours by appointment only - please do not disturb residents.

824 Post Avenue, 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, 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, Chesapeake
$239,900
10619801 MLS
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 to Suit lease package deals also. Call/text agent for more information.

Lot 4 Bedford Street, Chesapeake
$1,100,000
6 Beds ⋅ 3.1 Baths ⋅ 10618884 MLS
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 detached garage with above office space and its own heating/cooling. Swimming pool. Dramatic two-story foyer with curved staircase. Huge ground level master bedroom with master bath. Huge deck with all brick cook-out. Well maintained and move in condition.

2325 Woodhurst Lane, Chesapeake
$866,319
54 Beds ⋅ 4.1 Baths ⋅ 10619381 MLS
The Miles offers a layout designed to grow with you—while still feeling intentional and welcoming at every turn. Featuring 4 beds, 4.5 baths, & 3,585 square feet, this thoughtfully designed home delivers space, flexibility, & timeless appeal for modern living. Enter into a grand foyer that immediately sets the tone. To your left, a private home office offers the a retreat for remote work, quiet study, or creative pursuits. To the right, a formal dining room invites everything from holiday gatherings to weeknight dinners filled with conversation & connection. As you move forward, the home opens into a stunning great room, seamlessly flowing into the breakfast area / kitchen—creating the heart of home where life naturally comes together. Kitchen is designed with both beauty & practicality in mind, featuring a generous pantry —ideal for effortless entertaining & everyday organization. Just beyond breakfast area, you’ll find a half bath & direct access to the garage, making comings / goings easy & efficient. Tucked just off the great room, a versatile flex room with adjacent full bath & closet offers endless possibilities—whether you envision a guest suite, playroom, fitness space, or secondary living area. Upstairs continues to impress with spacious loft that serves as a natural gathering space—perfect for movie nights, homework sessions, or a cozy lounge. 3 additional beds provide comfort & privacy for family /guests, with Bed 2 & 3 connected by a Jack-and-Jill bathroom, blending convenience with thoughtful design. Primary suite is a true retreat, offering a peaceful escape complete with luxurious bath & expansive walk-in closet. Just outside the suite, the upstairs laundry room adds everyday ease—no hauling baskets up & down stairs, just smart living done right. Every corner has been carefully considered to support the rhythms of daily life while offering moments of comfort, connection, calm. Flexible living spaces to generous storage & intuitive layout, this home is more than a floorplan—it’s a place where memories are made!

2100 Sanderson Road, Chesapeake
$349,000
10619323 MLS
COMMERCIAL PROPERTY FOR SALE (FORMER TIRE SHOP) | B-2 ZONING | CORNER LOT | HIGH-VISIBILITY FRONTAGE | FULLY RENOVATED. Freestanding fully renovated commercial building on a high-visibility corner lot at Bainbridge Blvd & Jefferson St in Chesapeake. Zoned B-2 allowing a wide range of retail, office, and service uses. Property has been previously advertised/operated for automotive-related services. Features 825 SF, one-story building on 0.182-acre lot with large paved area (7,041 SF), providing excellent parking and flexibility. Recently REMODELED: New roof, flooring, doors, updated walls, modern kitchen, fully renovated bathroom w/ tankless water heater, new vanities, new recessed lighting, and 2 brand-new high-efficiency split HVAC systems. Buyer shall perform all due diligence and confirm zoning, use approval, and permitting requirements with the City of Chesapeake prior to making an offer.

1234 Bainbridge Boulevard, Chesapeake
$249,999
4 Beds ⋅ 2 Baths ⋅ 10618970 MLS
Beautiful property offering both investment and owner-occupant potential. Located in a desirable area. Sold As-Is. Seller will not make repairs . 4bedrooms 2full baths.

604 Amick Road, Chesapeake
$639,777
4 Beds ⋅ 3 Baths ⋅ 10618968 MLS
Stunning new construction ranch home by an experienced, award-winning builder! The popular Sandpiper model offers an open-concept main level designed for comfortable living and entertaining. The great room flows into the gourmet kitchen, featuring custom cabinetry, a large granite island, & stainless steel appliances. The primary suite is a private retreat with a generous walk-in closet & spa-inspired bath with LVT flooring, tub, tiled shower, double vanity, and private water closet. Two additional large bedrooms and a full hall bath are conveniently located on the main level. A fourth room situated over the garage includes its own full bath, making it ideal for guests, a home office, or bonus living space. Other features include a large utility room located just off the two-car garage, 9-foot ceilings, upscale LVT and carpet flooring, and an electronic fireplace with mantle. Large 1.7-acre lot close to interstates, schools and shopping.

2500 Deal's Creek Court, 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, Chesapeake
$1,250,000
10618613 MLS
Unique mixed-use investment in sought-after Hickory! Set on a rural parcel yet conveniently near major highways, 4443 Old Battlefield Blvd offers a versatile income-producing layout with multiple revenue streams. The property includes a duplex and a triplex for residential rental demand, plus two commercial spaces suited for neighborhood service, office, or small business use. Served by well and septic, this setup can help keep operating costs manageable (buyer to verify capacity, usage, and any expansion potential). Enjoy the appeal of country surroundings with commuter-friendly access—an attractive combination for tenants and business operators alike. Excellent opportunity to hold for steady cash flow, improve and reposition, or add value through rent optimization and targeted updates. Offered at $1,250,000. Buyer to verify zoning, permitted uses, and all property details.

4443 Old Battlefield Boulevard S, Chesapeake
$289,900
5 Beds ⋅ 3 Baths ⋅ 10618187 MLS
BEAUTIFULLY RENOVATED Victorian-style home blending timeless charm with modern updates! This spacious 5-bedroom, 3-bath home features a grand foyer, open floor plan, and abundant natural light throughout. The updated kitchen offers stainless steel appliances, granite countertops, 42” cabinetry, breakfast nook, and large island—perfect for entertaining. Formal dining room and bright living room with bay window. First-floor primary suite with ensuite bath. New flooring (carpet & LVP), fresh paint, updated fixtures, and baths. Major 2022 upgrades include roof, windows, doors, water heater, and high-efficiency 2-zone electric furnace with updated ductwork. Enjoy a large fenced yard, 425 sq ft front porch, and 4-car driveway. Centrally located near bases, beaches, shopping & interstates. Short sale sold as-is.

1129 Rodgers Street, 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, 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, Chesapeake
$4,000,000
10617270 MLS
Exceptional commercial opportunity featuring multiple buildings totaling nearly 30,000 sq ft of space, including multiple office suites, a dedicated showroom and tons of warehouse space for almost any need. Warehouses offer 18+ ft clear-span ceilings, multiple bay doors, and no interior posts, maximizing usable space. Property includes onsite bathrooms, well & septic, and two separate meters with 3 phase on site. Situated on almost 14 acres, offering room for future expansion and strong rental income potential possibilities could be endless. A main access cut-through from the 4-lane road provides excellent visibility and direct ingress for any size vehicle. Ideal for contractors, industrial users, distribution, multi-tenant investment or what ever you can think of this is something you don't want to miss.

4653 Battlefield Boulevard, Chesapeake
$95,000
2 Beds ⋅ 1 Baths ⋅ 10616828 MLS
Value is in the land. Property being sold as-is. Home is not in livable condition.

2053 Iowa Street, Chesapeake
$420,000
3 Beds ⋅ 2 Baths ⋅ 10616350 MLS
Welcome home to this move in ready, updated brick ranch situated on a spacious 2/3-acre lot in the heart of Chesapeake. Offering classic curb appeal and room to breathe, this home also boasts new paint & flooring throughout, all new kitchen cabinets, granite & appliances with breakfast bar. Large family room w loads of natural sunlight add to the functional, single-level layout designed for comfortable everyday living. The generous yard provides endless possibilities—ideal for outdoor entertaining, gardening, play, or future expansion. Mature surroundings and ample space create a peaceful setting while still being just minutes from shopping, dining, schools, and major roadways.This home offers a rare opportunity to enjoy privacy, space, and convenience all in one. Properties with this much land in such a desirable location don’t come along often—don’t miss it.

937 Mount Pleasant Road, Chesapeake
$449,990
4 Beds ⋅ 3 Baths ⋅ 10616106 MLS
Welcome home to this luxurious 4-bed, 3 full bath home located in the highly sought-after Great Bridge school district. The open floorplan is enhanced by 9-foot ceilings on both levels, recessed lighting, and plenty of natural light. The kitchen serves as the heart of the home, offering a large island, quartz countertops, and stainless-steel appliances— for both entertaining and everyday living. Upstairs, enjoy freshly installed carpet throughout, convenient upstairs laundry room, and a spacious primary suite that features both a generous walk-in closet and spa-like bathroom complete with a soaking tub, oversized shower, and double vanity. Additional highlights include a covered porch, relaxing back patio, and attached garage with extra driveway parking. Conveniently situated near interstates, shopping, schools, and military bases, this home combines modern style with low-maintenance living—an ideal opportunity to own in one of Chesapeake’s most desirable communities!

301 Sikeston Lane, Chesapeake
$400,000
5 Beds ⋅ 2 Baths ⋅ 10615520 MLS
Beautifully updated 3,333 sq ft. home featuring 5 spacious bedrooms and 2 modern bathrooms. The kitchen offers granite countertops, dark cabinetry, and updated appliances, making it both stylish and functional. Enjoy outdoor living on the private deck, perfect for relaxing or entertaining. This move-in ready home features elegant upgrades throughout and plenty of space for comfortable living. Don’t miss this opportunity—schedule your showing today!

3861 Ahoy Drive, Chesapeake
$449,900
4 Beds ⋅ 3 Baths ⋅ 10614629 MLS
Welcome to easy living in this beautifully upgraded, better than new condo in a vibrant 55+ community! This home is packed with upgrades and thoughtful touches throughout featuring custom Closet Factory closets, built in bookcases, high end appliances, and decorative molding. Bright open concept layout with a gourmet kitchen, oversized island, upgraded cabinetry and upgraded lighting. Spacious living and dining area for hosting or relaxing. Enjoy the convenience of first floor laundry, an abundance of storage space, and a bonus loft for hobbies, reading or watching the game. Step outside to your private screened-in porch, your personal retreat for morning coffee or evening conversations. Community amenities include a pool, exercise room, clubhouse and a full calendar of social activities and gatherings to help stay connected and moving. Best of all, this is low maintenance living, giving you more time to enjoy the things that matter most. You don't want to miss it! Welcome HOME!

4646 Longleaf Place, 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, Chesapeake
$599,900
4 Beds ⋅ 2.1 Baths ⋅ 10613272 MLS
Start building your custom dream home today! Exceptional new construction opportunity on a spacious half-acre lot in the heart of Western Branch. Design your own floor plan to match your lifestyle or choose from one of the builder's stunning models. This featured plan offers a modern open-concept layout. The chef's kitchen features granite countertops, custom cabinetry, stainless steel appliances, and designer lighting. A formal dining room can easily serve as a home office. Enjoy luxury vinyl plank flooring throughout the first floor and baths, plus a covered front porch and rear patio for outdoor living. Experience quality craftsmanship, thoughtful design, and the freedom to create the home you've always imagined. Ready in Spring 2026. Contact us today to start designing your custom dream home!

1530 Jolliff Road, Chesapeake
$1,250,000
6 Beds ⋅ 5 Baths ⋅ 10611669 MLS
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 in-ground heated pool for year-round enjoyment. A land-mounted solar system adds modern efficiency, keeping energy costs low while supporting sustainable living. With plenty of room to spread out, both indoors and out, this property is a rare opportunity to enjoy refined living on a private, spacious retreat.

2700 Ballahack Road, Chesapeake
$425,000
4 Beds ⋅ 2 Baths ⋅ 10611385 MLS
Fully remodeled in 2018. This contemporary open floor plan has 2 large living areas and 2677 square feet! Kitchen has tons of cabinets. lots of counter space and opens to a large living area. Huge first floor primary bedroom with walk in closet and extra large master bath. Stainless appliances,recessed lighting, lvp flooring, heat pump 2018, walk in attic, oversized living area with contemporary ELECTRIC fireplace, large pantry with barn doors, circular driveway and lots of curb appeal. Move in ready! Lots of room to unpack and relax!!

2218 Vicker Avenue, Chesapeake
$539,900
4 Beds ⋅ 2 Baths ⋅ 10609828 MLS
A versatile floor plan built with space for EVERYONE! Our Myrtle model offers ranch style living with 4 bedrooms including a large finished room over the garage. From the front porch to the Family Room also open to the Kitchen and Breakfast Area. The Estates at Jolliff Landing is a charming neighborhood boasting single family homes with covered porches, tree-lined sidewalks, lush gathering spaces, an assortment of yard games, community playground, water features, a sports field, bike paths, and a community clubhouse with a resort-style in-ground swimming pool. A plethora of outdoor activities right at your door step in an exciting new homes community! Builder is offering partial CCA & $15,000 buyer incentive (See listing agent for details as restrictions may apply) when using one of our preferred lenders. Model home open daily 12-5pm at 5023 Annapolis Drive.

MM Myrtle, Chesapeake
$609,900
6 Beds ⋅ 3 Baths ⋅ 10609830 MLS
A versatile floor plan built with space for EVERYONE! Our Myrtle model offers ranch style living with 6 bedrooms including a large finished room over the garage. Family Room opens to the Kitchen and Breakfast Area. The Estates at Jolliff Landing is a charming neighborhood boasting single family homes with covered porches, tree-lined sidewalks, lush gathering spaces, an assortment of yard games, community playground, water features, a sports field, bike paths, and a community clubhouse with a resort-style in-ground swimming pool. A plethora of outdoor activities right at your door step in an exciting new homes community! Builder is offering partial CCA & $15,000 buyer incentive (See listing agent for details as restrictions may apply) when using one of our preferred lenders. Model home open daily 12-5:00 pm at 5023 Annapolis Drive.

MM Myrtle Ii, Chesapeake
$938,197
4 Beds ⋅ 3.1 Baths ⋅ 10609126 MLS
Discover just the right blend of comfort & functionality in this exceptional property, featuring two primary bedrooms - one on each level! Situated on a sprawling 3-acre lot, this home offers ample space for a hobby farm & enjoying stunning sunsets. The kitchen boasts a walk-in pantry, extensive cabinetry, as well as an 8ft island. A versatile loft offers storage & flexible living areas for those needing a play room or office space. The formal dining room offers flexibility to suit your needs, whether you prefer an elegant dining space or home office. Outdoor enthusiasts will appreciate the expansive covered rear porch and large front porch, great for relaxation, entertaining, and morning coffee! Trusted lender incentives available! PRESOLD & TO BE BUILT. OTHER HOMESITES AVAILABLE. BUILD TIME 7-10 MONTHS. INCENTIVES AVAILABLE WITH TRUSTED LENDER.

1432 Taft Road, Chesapeake
$240,000
10608068 MLS
Vacant cleared lot, road access via access easement via lot 1 adjacent to Taft road

B Taft Road, 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.