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$883,500
4 Beds ⋅ 2.1 Baths ⋅ 10624904 MLS
NO HOA! 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, movie marathons & social gatherings await, creating memories that will last a lifetime. When the day winds down, retreat to the sanctuary of the primary suite. Open the elegant doors to reveal a spa-like bath, inviting you to unwind in luxury. But that's not all—not one, but two walk-in closets await, offering a beautiful space for your wardrobe & a touch of indulgence. Beyond these sought-after features, The Ambler boasts practical features such as a generous mudroom & closets galore, ensuring that every belonging finds its place. Pictures from past build. May show options for inspiration.

MM Sanderson (Ambler Parcel 11 Homesite 5 ) Road, South Chesapeake
$643,265
4 Beds ⋅ 2.1 Baths ⋅ 10624520 MLS
This beautiful Wells plan will be move-in ready in September and is backing a mature tree line, featuring 4 spacious upstairs bedrooms, including an owner’s suite with a tiled shower and quartz double vanity. The bright, open kitchen boasts a large island, quartz countertops, stainless steel appliances, and a generous pantry. Enjoy an inviting front porch, a welcoming foyer with ample storage, and a fenced backyard. Additional highlights include a 2-car garage and custom wood shelving in large closets. Seller to pay up to $10k in closing cost assistance when using preferred lender, see agent for details. Buyer must register agent on or before first visit or first substantial communication with listing agent and Agent must accompany Buyer on 1st visit, see Listing Agent for details. Photos & video are of previously completed home, finishes and upgrades vary.

709 Crestfield Drive, South Chesapeake
$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
$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
$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
$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
$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
$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
$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
$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
$275,000
2 Beds ⋅ 2 Baths ⋅ 10615675 MLS
Move-in ready and one-level living! This spacious 2-bedroom, 2-bath home offers 1,304 sq ft with large living areas and a massive primary suite featuring a walk-in closet and full bath. Enjoy an outdoor patio with an exterior storage closet and the ease of low-maintenance living. The home features many thoughtful upgrades throughout that you don't want to miss out on. Schedule a showing today! Closing Cost Assistance available through the Listing Edge Program.

712 Inlet Quay Unit A, 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
$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
$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, South 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, 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
$1,278,786
4 Beds ⋅ 3.1 Baths ⋅ 10606247 MLS
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 sprawling island remains clear for entertaining, prepping, or gathering. A spacious walk-in pantry & a stylish butler’s pantry just off the kitchen, ensure that everything you need is w/in reach, yet artfully tucked away. Upstairs, the primary suite becomes your personal sanctuary. W/ two walk in closets & a lavish ensuite - this will be your own hidden gem. the second floor wouldn't be complete without a bonus room, jack and jill bedrooms/bath, plus an additional bed and bath. But the feature not to miss - OPT second floor balcony! Photos from past build & some virtually staged for inspiration.

1533 Cedarville Court, South Chesapeake
$774,500
3 Beds ⋅ 2 Baths ⋅ 10606118 MLS
Discover the perfect blend of luxury, comfort, and convenience in this beautifully designed home located in one of the most highly sought-after 55+ communities in the area. Nestled in a prime location, this neighborhood offers both tranquility and accessibility, with shopping, dining, healthcare, and recreation just minutes away. What truly sets this community apart is the fully customizable home-building experience. From floor plan layouts to finishes, fixtures, and features—you have the unique opportunity to create a home that reflects your personal style and needs. Whether you want an open-concept kitchen, a spa-inspired bathroom, or energy-efficient upgrades, you design it your way. Don't miss your chance to build the home you've always dreamed of in a location you'll love. The Cottages at Edinburgh!

1513 Caden Lane Unit 29, South Chesapeake
$985,769
4 Beds ⋅ 3.1 Baths ⋅ 10604315 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.

1429 Taft Road, South Chesapeake
$460,500
4 Beds ⋅ 2 Baths ⋅ 10601728 MLS
Welcome to your new home! This beautifully maintained 4-bedroom, 2-bathroom house offers a perfect blend of comfort and style. This home includes Newly installed Roof and water heater for year-round comfort and efficiency. Kitchen is cozy and Fully equipped with all-new stainless steel appliances, granite counter-tops, stylish fixtures, and ample counter space, great for cooking and entertaining. Enjoy a bright and airy living room featuring large windows and new flooring that enhances the welcoming atmosphere. Bedrooms have fresh paint, new windows and new fixtures. Located in the heart of Great Bridge this home is near school, parks, and shopping

557 Waters Road, South Chesapeake
$677,000
4 Beds ⋅ 2.1 Baths ⋅ 10596855 MLS
Nestled in an established and sought after neighborhood, this meticulously maintained home offers a perfect blend of comfort and elegance. Boasting 4 spacious bedrooms, 2.5 baths, this residence features mature landscaping and beautiful updates throughout. The kitchen is a chef's dream with quartz countertops, updated cabinetry and stylish backsplash. Enjoy the sunroom year-round, equipped with electric baseboard heat. Includes walk in pantry and ample storage in the utility room. Hardwood floors grace the living room and dining areas, while the new LVT floors enhance the foyer and kitchen. Freshly painted den with fireplace and updated LVT. Primary ensuite is a retreat with two walk-in closets, trey ceiling, updated cabinetry with quartz counters, double vanity sinks, with double shower heads and additional hand wand. One of the 2nd floor bedrooms features walk out balcony. Additional highlights include solar panel system, freshly stained pergola, a 12x12 shed, gutter guard system.

1609 Burton Place, South 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.