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801 Keeling Drive Drive, South Chesapeake
$695,000
4 Beds ⋅ 3.1 Baths ⋅ 10656163 MLS
Your own private retreat in the heart of Cheshire Forest! This beautifully maintained 4 bedroom, 3.5 bath home offers over 3,100 sq ft with a floor plan made for everyday living and entertaining. Inside, enjoy gorgeous oak floors, an updated open concept kitchen, formal living and dining rooms, a sun-filled family room with fireplace, and a spacious primary suite with its own fireplace. Outside is where this home truly shines; take a dip in the heated in-ground pool, relax on the deck, or unwind in your private, fully fenced backyard. An impressive list of improvements includes a new pool liner (2025), upstairs A/C (2024), refinished hardwood floors, updated roof, gutters, garage door, HVAC, water heater and more. Two-car garage plus Cheshire Forest amenities including a clubhouse, community pool, playground and tennis courts. A rare combination of space, updates and resort-style living in Great Bridge!

801 Keeling Drive Drive, South Chesapeake

317 George Washington Highway S, South Chesapeake
$524,900
3 Beds ⋅ 2 Baths ⋅ 10655769 MLS
Five acres. A powered detached workshop. Room to breathe, space to make your own. This updated Cape Cod offers the flexibility of acreage living in Chesapeake’s Grassfield area. The home features 3 bedrooms, 2 full baths and a first-floor bedroom and full bath. MLS square footage reflects 1,869 sq. ft. per tax records; a recent appraisal measured approximately 2,067 sq. ft.Updates include a renovated kitchen and baths, replacement windows, updated electrical and plumbing, a 2023 heat pump, 2024 whole-house paint and newer flooring. Beautiful hardwood floors, a fireplace, and generous mud/laundry space add function and character. The approx. 736 sq. ft. powered detached garage/workshop offers room for tools, projects, and storage. Gorgeous outdoors boast a fenced yard area, wooded acreage, mature fruit and fig trees, enclosed porch, deck and patio. City water/sewer add convenience. Recent appraisal at $600,000! Existing VA loan may be assumable, reach out to listing agent for more details.

317 George Washington Highway S, South Chesapeake

109 Causeway Drive, South Chesapeake
$429,900
3 Beds ⋅ 2 Baths ⋅ 10655782 MLS
Welcome to 109 Causeway Dr, a charming home nestled on a quiet street in the highly desirable Great Bridge area of Chesapeake! Enjoy major peace of mind with recent big-ticket upgrades, including a newly updated HVAC system, new water heaters, flooring throughout, and the electrical panel in the garage updated within the last 2 years. One of the standout features of this property is the HUGE backyard—providing an abundance of open space for entertaining, gardening, or play. Plus, there is ample parking and side access with more than enough space to park your large RV, boat, trailer, or multiple vehicles. Location is everything! Situated just off Battlefield Blvd, you are minutes away from top-rated Chesapeake public schools, local parks, waterways, and the Intracoastal Waterway. You'll love the convenience of quick access to everyday shopping, dining, medical facilities, and major highways for an easy commute throughout Hampton Roads.

109 Causeway Drive, South Chesapeake

1145 Sunlight Drive, South Chesapeake
$475,000
4 Beds ⋅ 2 Baths ⋅ 10655999 MLS
Escape to your own private waterfront retreat on nearly 1/2 acre in the sought-after Inland Colony community, where peaceful wooded surroundings and serene water views create the perfect connection to nature. This 2,494 sq. ft. home offers 4 bedrooms, 2 baths, a first-floor primary suite, detached ADU, 1-car garage, and private dock with access to the Intracoastal Waterway on the Elizabeth River. Enjoy the expansive deck overlooking the backyard and water or unwind on the screened porch off the primary suite. Fresh paint and new carpet enhance the bedrooms, while the spacious kitchen features granite countertops, stainless steel appliances, abundant cabinetry, and generous prep space. French doors open from the dining room to the living area, creating an ideal layout for entertaining. The FROG with new carpet and large walk-in attic provide excellent flexibility and storage. Some photos may be virtually staged. Conveniently located near shopping, dining, top-rated schools, and interstate access while offering a true waterfront escape.

1145 Sunlight Drive, South Chesapeake

241 Sign Pine Road, South Chesapeake
$950,000
4 Beds ⋅ 3.1 Baths ⋅ 10655919 MLS
Your dream home awaits!! Craftsman bones, a custom remodel, and a horse barn out back: acreage living with refined character. Every inch of this home was designed by the sellers who were contractors with love over the years. Inside, coffered ceilings meet warm cedar and wood-plank ceilings, giving every room a crafted, finished feel, and Brazilian cherry hardwoods run underfoot toward a stone gas-log fireplace that anchors the living space. Floor-to-ceiling windows and skylights flood the home with light, while custom barn doors and Restoration Hardware fixtures make even the transitions between rooms feel intentional. The kitchen is built to gather around. An oversized honed granite island with a built-in microwave takes center stage, backed by custom cabinetry, an etched tile backsplash, a built-in pantry, newer appliances, and purified water at the sink. Next door, color-changing upper lighting lets the dining room shift from weeknight dinner to late-night celebration at the flip of a switch. The first-floor and second story primary suite comes with its own bath, the bathrooms have been updated throughout, and a sun room, bar and mudroom with drop zone give the layout room to breathe. Then step outside, where the property really shows off. A 40,000-gallon saltwater pool, 8 feet deep with a diving board and fountain, sits beside a koi pond and gazebo linked by brick walkways. Made for a party or a wedding. Beyond it, a fenced acre of pasture leads to a barn with two stalls, a wash stall, a brick-paved breezeway, tack room, and horses are allowed. Wrapped in Hardie plank and stone, heated and cooled by geothermal, and tucked into a wooded setting of nearly five acres neighboring Greenbrier Farms in the Hickory school zone. Morning coffee in the sun room, afternoons at the barn, evenings by the pool: this home makes every part of the day worth staying for. And let's talk privacy.

241 Sign Pine Road, South Chesapeake

1103 Madison Lynn Way, South Chesapeake
$640,000
5 Beds ⋅ 2.1 Baths ⋅ 10655665 MLS
Welcome home to 1103 Madison Lynn Way in Chesapeake! Located in the sought-after Hanbury Manor community and Great Bridge School District, this spacious 5-bedroom, 2.5-bath home offers approximately 2,557 square feet with a bright, open layout designed for everyday living and entertaining. The main level features an inviting living area, dedicated dining space, and a first-floor bedroom ideal for guests, a home office, or flex space. The updated kitchen features quartz countertops, stainless steel appliances, ample cabinetry, and LVP flooring. Upstairs, you’ll find four additional bedrooms, including a spacious primary suite with cathedral ceilings, a walk-in closet, and ensuite bath with a soaking tub and separate walk-in shower, along with a dedicated laundry room with a utility sink. Outside, enjoy a fully fenced backyard with a patio and storage shed, plus an attached two-car garage. With no HOA and a convenient location near Great Bridge schools, shopping, dining, and interstate access, this home offers the space, updates, and location you’ve been looking for!

1103 Madison Lynn Way, South Chesapeake

200 Traditions Way, South Chesapeake
$655,000
3 Beds ⋅ 3.1 Baths ⋅ 10655918 MLS
This SHOWCASE home can be yours - MOVE IN READY! Award-winning builder blends elegance and easy living w/all grounds maintained! Exceptional details - Custom lighting throughout, Designer wallpaper, Culinary bar, White oak beams and more, and Matte White GE Cafe appliances w/Brushed Brass. French doors open to custom 12x30 paver w/fenced yard. HW throughout first floor, first floor BR with full bath, tiled shower, first-floor laundry (and full laundry up). Upstairs HW flooring in Up Hall, Loft and Primary BR. Loft with custom bar for relaxing evenings. Stunning primary BR with 10'x13' custom walk-in closet and 2 finished closets 10'x5' finished storage closets. Spa-inspired bath with 9' vanity, WOW shower, free-standing tub, champagne ready. Professionally managed community.

200 Traditions Way, South Chesapeake

1153 Edinburgh Parkway, South Chesapeake
$725,000
5 Beds ⋅ 3 Baths ⋅ 10655913 MLS
Cottage charm on the outside, showstopper on the inside, and Stephen Alexander craftsmanship in every detail! This Caramel Cottage in Great Bridge delivers the builder's signature molding and trim, soaring 10-foot ceilings, and rich hardwood floors from the moment you step into the foyer. The highly flexible floor plan features a sought-after first-floor bedroom and full bath, or a dedicated office/study and a formal dining area ready for holiday dinners and special occasions. The living room is anchored by a gas fireplace framed in custom built-ins, creating a warm and inviting gathering space that flows easily into the heart of the home. The kitchen is the true showpiece, with 42" white cabinetry that rises to meet those tall ceilings, an oversized island with plenty of room to gather, a gas range, stainless appliances, and a walk-in pantry for effortless organization. The breakfast area adds a relaxed spot for everyday meals, making cooking and entertaining easy. Upstairs, the primary suite is a private retreat with a tiled shower, jetted soaking tub, dual vanities, and a spacious walk-in closet. A finished room over the garage offers even more flexibility as a media room, hobby space, or bonus room, and brand-new carpet is already in place! And then there's the porch! The three-season Eze-Breeze enclosure is one of the home's best features, with sliding vinyl panels that open wide to let the breeze in and close up to keep rain, wind, and bugs out, so porch season doesn't end when summer does. From there, step down to the large paver patio in a privacy-fenced backyard, a relaxing setting for morning coffee, evening gatherings, or simply unwinding outdoors. Thoughtful details continue throughout, including zoned heating and cooling, fiber cement siding, a walk-in attic for extra storage, a utility room, and an attached two-car garage with additional driveway parking. From the curb to the craftsmanship, every inch of this home was built with intention. This is Great Living in Great Bridge!

1153 Edinburgh Parkway, South Chesapeake

1204 Lingale Court, South Chesapeake
$749,000
5 Beds ⋅ 3 Baths ⋅ 10655942 MLS
Welcome to this beautifully updated 5-bedroom, 3-bath brick ranch tucked away on a quiet cul-de-sac in sought-after Emerald Lakes. Offering approximately 3,200 square feet, this home features a bright open-concept design with soaring cathedral ceilings, Brazilian walnut floors, custom trim, wainscoting, wood ceiling beams, and extensive upgrades throughout. The remodeled kitchen boasts quartz countertops, custom range hood, newer appliances, subway tile backsplash, and overlooks the spacious living area with gas fireplace and striking wood accent wall. The first-floor primary suite offers private patio access, a cedar-lined walk-in closet, jetted tub, separate shower, and dual vanities. The finished FROG with full bath is ideal as a guest suite, media room, or fifth bedroom. Additional highlights include a 3-year-old HVAC, 2018 water heater, rebuilt rear stairs (2026), irrigation system, custom landscaping, in-wall surround sound, oversized driveway, no HOA, and a private fenced backyard.

1204 Lingale Court, South Chesapeake

1011 Cedar Tree Court, South Chesapeake
$684,824
4 Beds ⋅ 2.1 Baths ⋅ 10655903 MLS
Welcome to the popular Campbell model by Kirbor Homes, where thoughtfully designed spaces meet modern luxury. This home features a magnificent primary suite complete with a spacious walk-in closet, a spa-like ensuite featuring a freestanding tub, and a large bedroom designed for ultimate relaxation. The main level offers a dedicated home office, a cozy fireplace, and beautiful LVP flooring flowing throughout all main living areas. At the heart of the home, the extended kitchen provides ample counter space and storage, making entertaining effortless. Practical details like built-in mudroom cubbies keep daily life organized, while the rear covered porch offers the perfect outdoor retreat to unwind. Contact us today to learn more and explore options for your new home!

1011 Cedar Tree Court, South Chesapeake

141 Marion Drive, South Chesapeake
$475,000
3 Beds ⋅ 2 Baths ⋅ 10655827 MLS
Turn-key & ready to enjoy! Backyard gatherings, room to spread out, & a place to call your own! This 3 bedroom, 2 bath home in Great Bridge has a lot to offer, inside & out. Situated on just shy of 1/2 acre, it features an open floor plan, office space, LVP flooring, brand new bedroom carpet, fresh paint throughout (even in the garage), remodeled baths, granite countertops & high-efficiency HVAC. The fenced backyard shines with a new wood privacy fence, above-ground pool, hot tub, fire pit & covered patio, making it a great spot to entertain or unwind. A front deck adds another place to relax. The detached metal building, approx. 1,000 sq. ft. with 2 roll-up doors, offers room for hobbies, projects, storage or a workspace. An attached 1-car garage & storage shed round out the package. Looking for a home with room to entertain, space for your hobbies & a backyard you'll actually use? This is the one!

141 Marion Drive, South Chesapeake

1108 Kathleen Lane, South Chesapeake
$1,195,000
5 Beds ⋅ 4.1 Baths ⋅ 10655222 MLS
This home truly has it all! Meticulously maintained & beautifully updated, this custom home sits on 3 acres offering space, privacy & versatility. Hardwood floors span the 1st & 2nd floors, complemented by plantation shutters. With 5 bedrooms, PLUS a finished room over the garage, there is room for everyone, including 3 bedrooms with ensuites .The 1st floor primary features a clawfoot tub & separate shower. A gorgeous kitchen with updated appliances & pot filler opens to the family room & bright sunroom with wood stove overlooking the saltwater pool. Outside, enjoy a low maintenance deck, attached 2-car garage, detached 2-car garage with unfinished 2nd floor & extra parking for a boat or RV. Brand new roof, updated HVAC ,remodeled bath & numerous additional improvements make this home truly move-in ready. Assumable 2.25% VA loan. This one is a must see!

1108 Kathleen Lane, South Chesapeake

2410 Centerville Turnpike, South Chesapeake
$879,000
3 Beds ⋅ 2 Baths ⋅ 10655763 MLS
If these walls could talk, they would tell you 176 years of stories. Rare pre-Civil War farmhouse charm meets modern comfort in this private retreat that feels like a vacation every day. This 2-story home is filled with character, featuring 4 fireplaces, gorgeous original hardwood floors, 10-foot ceilings, hand-sawed original moldings, intricate ceiling details, and antique lighting. The living room offers a cozy wood-burning stove, while the family room showcases coffered ceilings and original hardwood floors. The spacious primary suite stands out with a beautiful fireplace and a wall of built-in cabinetry offering storage rarely found in modern homes. Enjoy two laundry areas, including one in the ADU over the detached tandem 4-car garage, plus a flexible space for an office or mudroom off the back of the main house. Outside, unwind and entertain by the pool oasis, or sit on the 250 sqft covered porch. There is a huge new chicken coop (26), and 2 dog runs for that farm life as well as a shed (as is). The brick walkways are the original bricks from the chimney repurposed. Updates include painted kitchen cabinets/walls (26), sealed and painted metal roof with 20 year paint (26), new pool liner (25), encapsulated crawlspace with dehumidifier/support beams (25), 50-gallon hot water heater (25), HVAC, and ductwork (23), new steps and railing out to the pool (26), breaker upgrade to house (25) 2 solar systems one to the main house and one to the ADU/garage (23). More updates listed in agent remarks. Near Hickory schools, shopping, Bypass, and OBX. Come own a piece of history in Hickory!

2410 Centerville Turnpike, South Chesapeake

3145 Codorus Street, South Chesapeake
$500,000
4 Beds ⋅ 2.1 Baths ⋅ 10655704 MLS
Seller is offering $3,000 to be used at buyers discretion!!! Beautifully updated and move-in ready, this home offers the perfect blend of comfort, style, and community. Recent improvements include luxury vinyl plank flooring throughout, a beautifully renovated primary bath with a spacious walk-in shower, and the addition of a fourth bedroom for added flexibility. Outside, the large backyard is framed by mature weeping willow trees, creating a peaceful retreat on a quiet side street. Beyond your front door, enjoy a lifestyle that’s hard to find—golf cart rides to the clubhouse, afternoons at the resort-style pool, workouts in the fitness center, visits to the dog parks and playgrounds, and a calendar full of neighborhood events including community picnics, book club, cigar & bourbon nights, festive holiday celebrations, and the beloved Christmas golf cart parade. Experience everything this vibrant, close-knit community has to offer in sought-after Culpepper Landing.

3145 Codorus Street, South Chesapeake

220 Marion Drive, South Chesapeake
$435,000
3 Beds ⋅ 2 Baths ⋅ 10655721 MLS
Location, Location, Location, Welcome to the desirable Great Bridge area of Chesapeake! This beautifully updated 3-bedroom, 2-bath home offers approximately 1,700 square feet of comfortable living space, with many of the major projects already completed. Inside, enjoy an inviting layout featuring a remodeled kitchen, refreshed bathrooms, new dishwasher 2026, 2019 AC system, and new 2025 evaporator coil. The cozy fireplace and chimney have also been professionally maintained, ready to enjoy. Outside, your private backyard retreat awaits! The inground pool is great for relaxing and entertaining, while the detached workshop offers versatile space for hobbies, projects, storage, or gatherings. The fully fenced yard provides privacy and plenty of room to enjoy. The home has been thoughtfully maintained, including 6-inch commercial gutters and professionally leveled and graded ground for proper drainage. The major mature trees around the home have been removed, reducing the potential for damage from falling limbs during severe weather. Additional improvements include a 2014 roof on all structures, plus a vapor barrier and dehumidifier installed in the crawlspace in 2019. The major work has been done—just unpack and enjoy! Come see everything this well-maintained Great Bridge home has to offer and schedule your private tour today.

220 Marion Drive, South Chesapeake

804 Brookside Arch, South Chesapeake
$737,000
4 Beds ⋅ 3 Baths ⋅ 10655495 MLS
Welcome to this beautifully updated all-brick ranch home in sought-after Emerald Lakes in southern Chesapeake, Virginia. This 2,777-square-foot home offers 4 bedrooms, 3 full baths, one-level living & a 2-car side-load garage on a 1/2-acre cul-de-sac lot. The gourmet kitchen features quartz countertops, a 5-burner gas cooktop, GE Profile stainless appliances, double oven & butler’s pantry, with both an eat-in kitchen & formal dining room. Primary suite w/private bath plus separate en-suite bedroom—ideal for multigenerational living—and two additional bedrooms. Cathedral ceilings, hardwood floors, a gas fireplace & flexible office/library space. The saltwater inground pool, stone patio, gazebo & large outdoor fireplace create an exceptional private entertaining space. New pool salt cell with Wi-Fi controls, encapsulated crawl space with dehumidifier, approximately 3-year-old roof and 2-year-old water heater. Convenient to the NC line, Moyock & the NC Outer Banks.

804 Brookside Arch, South Chesapeake

518 Whisper Walk, South Chesapeake
$465,900
4 Beds ⋅ 2.1 Baths ⋅ 10655312 MLS
Welcome home to this beautifully maintained condominium in the highly sought-after Cedar Crossing community. This spacious open concept residence offers over 2,000 square feet of comfortable living space. Four bedrooms featuring a large primary bedroom suite on first level, with double vanity and large walk-in closet. Beautiful hardwood floors, and crown molding throughout. Tile in kitchen, bathrooms and mudroom. Enjoy the privacy of a fenced backyard with storage shed for additional equipment. Two car garage and driveway space. Neighborhood has a well-equipped playground, swimming pool, tennis court and clubhouse. Enjoy low-maintenance living in a vibrant community conveniently located near shopping, dining, schools, and major commuter routes.

518 Whisper Walk, South Chesapeake

MM James 2, South Chesapeake
$720,000
5 Beds ⋅ 3 Baths ⋅ 10655465 MLS
Model Home to Be Built - James II Model at Riverview Landing by Wetherington Homes. This thoughtfully designed floor plan offers an Owner's Suite, two additional bedrooms, and a utility room conveniently located on the first floor. Buyers may select their lot and personalize available design options. The home includes a variety of well-appointed features designed to support modern living. The community offers eight floor plan options along with multiple exterior elevations that highlight architectural detail and curb appeal. Contact us today for additional information, to join the VIP interest list, and to schedule an appointment. Discover the opportunity to build in this thriving new community in Chesapeake!

MM James 2, South Chesapeake

204 Henry Jefferson Way, South Chesapeake
$709,990
4 Beds ⋅ 3 Baths ⋅ 10655470 MLS
The Savannah offers a well-designed floor plan with a spacious great room centrally located, creating a natural flow into the kitchen and dining area—great for everyday living and gatherings. The home features four generously sized bedrooms, including an owner’s suite positioned at the rear of the home for added privacy. The owner’s suite includes direct access to the covered porch and two large closets. A flexible space just off the foyer provides versatility for use as a home office, additional living area, or formal dining space, depending on your needs. The second floor includes an additional bedroom, a full bath, and a loft area, offering extra living options for guests or multi-functional use. Thoughtful layout and functional spaces make the Savannah a comfortable and adaptable home.

204 Henry Jefferson Way, South Chesapeake

3221 Stefanie Court, South Chesapeake
$380,000
4 Beds ⋅ 3 Baths ⋅ 10655445 MLS
Experience the easy charm of Strawberry Acres! This 4-bedroom, 3-bath offers a desirable first-floor primary suite with a private bath, plus two additional bedrooms and a full bath on the main level. The finished room over the garage provides a private retreat with its own full bathroom, ideal for guests, multigenerational living, a home office, or bonus space. The fully finished garage adds versatility for hobbies, storage, or a workshop. Outside, enjoy a large yard with plenty of room for entertaining, gardening, play, or simply relaxing in a peaceful setting. Located near schools, parks, shopping, dining, and with quick access to I-64, this home offers the combination of convenience and everyday comfort. Seller is offering a flooring allowance with an acceptable offer, giving buyers the opportunity to personalize the home to their taste. Don't miss this exceptional opportunity to own a home that combines space, flexibility, and location at an affordable price right in Chesapeake!

3221 Stefanie Court, South Chesapeake

1345 Oak Ridge Drive, South Chesapeake
$629,900
4 Beds ⋅ 2 Baths ⋅ 10655393 MLS
Welcome home to this charming 4-bedroom, 2-bath brick ranch nestled on 4.22 wooded acres at the end of a quiet cul-de-sac. Inside, you'll find a warm and inviting layout featuring a family room with a wood-burning fireplace, formal living and dining rooms, granite countertops, and beautifully updated primary and hall bathrooms. Step outside to relax on the new composite deck (2024), gather around the fire pit, or enjoy the peaceful wooded surroundings. The property also includes a detached 2-car garage with a finished studio apartment and full bath, plus a whole-house generator and water softener for added convenience. Offering space, privacy, and versatile living, this property is ready to welcome you home!

1345 Oak Ridge Drive, 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.