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$736,105
4 Beds ⋅ 3.1 Baths ⋅ 10623295 MLS
Experience the perfect blend of comfort and functionality in this versatile ranch home. The heart of the residence features an expansive open-concept living area, overlooking the kitchen with oversized island. Retreat to the spacious owner’s suite, a private sanctuary complete with a generous walk-in closet & a spa-like ensuite featuring a soaking tub & separate walk-in shower. Two additional bedrooms offer flexibility for guests or a home office. A large finished room over garage adds a 4th bedroom & full bath, included in list price, plus attic storage. Seller to pay up to $10,000 in closing cost assistance when using preferred lender, see agent for details. Buyer must register agent on or before first visit or first communication w/ listing agent & Agent must accompany Buyer on 1st visit, see Listing agent for details. Photos & Video are of previously built homes, finishes vary.

729 Crestfield Drive, South Chesapeake
$485,000
4 Beds ⋅ 2.1 Baths ⋅ 10623213 MLS
Beautiful Colonial-style home situated on a spacious 0.41 acre corner lot w/ deep water access, dock and bulkhead. Offering approx. 2100 sq.ft. Of living space, this 4 bed 2.5 bth home blends classic charm w/ comfy living. Enjoy cozy evenings by the fireplace and take advantage of the expansive backyard-perfect for entertaining, outdoor activities, or future enhancements. The large corner lot provides added privacy and curb appeal, while the storage shed and attached garage offers lots of extra space for tools and equipment. A rare opportunity to own a waterfront property w/ room to spread out, both inside and out.

824 Heritage Point, South Chesapeake
$775,500
3 Beds ⋅ 2 Baths ⋅ 10623022 MLS
Discover the Whitehurst, a stunning new ranch-style design situated on a premier 1.2-acre homesite. This exceptional property offers a serene lifestyle w/ both water & wooded views, complemented by community walking trails. Home Highlights: Enjoy the outdoors year-round with an included rear covered porch. This floor plan is designed for flexibility. Need more space? An entire second floor can be customized to create: Dual Primary Suites or a bonus room, as well as a 5-bedroom layout. Abundant Storage: Includes a convenient walk-out attic. Personalization: Meet to tailor the finishes and options to your specific needs and lifestyle. Low-Maintenance HOA: The Homeowners Association covers common ground maintenance only, keeping your overhead low while protecting community aesthetics. Don't just imagine it—experience it! This floor plan is currently available to tour in a nearby community so you can see the quality firsthand.

MM Racoon (Whitehurst - Homesite 16-1) Trail, 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
$289,900
10620680 MLS
"Turnkey Commercial Property with Income producing opportunity!! Zoned B-3, this versatile property supports a wide range of commercial uses. Currently operating as a fitness studio, the space can easily be adapted to accommodate various business types. Extensively renovated and upgraded in 2024, this property standsout having a valid Certificate of Occupancy and is ADA compliant. Excellent road frontage provides strong visibility and is close to major highways for easy access to all of Hampton Roads. Features include front and rear entrances and ample paved off-street parking in both the front and rear of the building. Detached oversized garage with electricity offers additional storage or workspace. Garage conveys As Is. Month to month tenants in place, Rent rolls available upon request. Shown by appointment only."

4208 Bainbridge Boulevard, Central Chesapeake
$400,000
3 Beds ⋅ 2.1 Baths ⋅ 10620994 MLS
Welcome to 949 Gabion Way, with comfort and style, the first-floor family room is perfectly suited for a home theater or media retreat, while upstairs features plush, sound-dampening carpet that creates a warm and cozy atmosphere year-round. The kitchen and bathrooms showcase luxury tile finishes, complemented by upscale lighting that elevates every space. A living room bump-out provides flexible room for a home office, playroom, or sitting area. The garage includes custom shelving for added storage, and the backyard is built for entertaining with beautiful pavers and a firepit. Located in a sought-after waterfront community, you’ll enjoy resort-style amenities including a pool, fitness center, clubhouse, private beach access, dog park, and even a boat dock. With a low HOA, no flood insurance required, and zoning for highly desirable Grassfield schools, this home truly checks every box. Opportunities like this don’t come around often.

949 Gabion Way, 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
$849,900
4 Beds ⋅ 3.1 Baths ⋅ 10621227 MLS
Start building your custom dream home today on a 3-acre cul-de-sac lot! This exceptional new construction opportunity allows you to design a floor plan that fits your lifestyle or select from one of the builder's beautifully crafted models. The featured plan showcases a modern open-concept layout with 4 bedrooms plus a first-floor flex room with a private bath great for guests or a home office. The chef's kitchen includes quartz countertops, custom cabinetry, stainless steel appliances, and recessed lighting. Luxury vinyl flooring runs throughout the first floor and all bathrooms. Relax on the covered front porch or rear patio. Enjoy quality craftsmanship, thoughtful design, and the freedom to create a home that's truly yours. Contact us to begin designing today!

3722 Carley Court, South Chesapeake
$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, 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
$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, Central 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
$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, South 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, South 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, South 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, Central 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, Central 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, 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
$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, South 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, Central 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
$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, South 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, South 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, South 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, South 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, West 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, West 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.