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3136 Sybilla Street, South Chesapeake
$578,000
4 Beds ⋅ 3.1 Baths ⋅ 10650309 MLS
This beautifully maintained 4-bedroom, 3.5-bath home offers generous space for the whole family - including a second bedroom with its own En suite, perfect for guests or multi-generational living. The primary suite easily accommodates a king size bed, includes his and her closets for effortless organization, and a jetted tub for some needed relaxation. Recent updates include a newer HVAC system (Fall 2021) for year-round peace of mind. Enjoy movie nights with home theater wiring already in place in both the family room and loft. Outside, the well-maintained yard shines - and the private landscape well keeps your greenery lush and your flowers blooming - while saving on water bills. Still need space? You’ll love the extra storage tucked in the attic, garage, and under the stairs. Additionally, the garage has a side entrance and a convenient utility sink. The Culpepper Landing community enjoys its own swimming pool and clubhouse, a dog park, and multiple playgrounds.

3136 Sybilla Street, South Chesapeake

1040 Drumcastle Lane, South Chesapeake
$975,000
5 Beds ⋅ 3.2 Baths ⋅ 10649439 MLS
Welcome to 1040 Drumcastle Lane, where space, neighborhood, and convenience come together on approximately 4.8 acres! Located in a beautiful neighborhood of large lots, this expansive property provides the feel of living in the country with the convenience of being near stores and schools. Custom built with care and quality, the home features stone detail inside and out, a fantastic open great room, and a kitchen with a huge island with a prep-sink, double ovens, and a walk-in pantry. The first-floor primary suite provides a beautiful view, access to the deck, and a private bath. The bathroom is its own showcase, with separate sinks, a lavish shower with two shower heads and beautiful tile, and a jetted tub. An additional first-floor bedroom offers flexibility for an office or workout room. Upstairs, you’ll find comfortable bedrooms and two jack-and-jill bathrooms with high-end finishes. In addition to the oversized attached two-car garage, this home offers a fantastic oversized detached 3-car garage, allowing for multiple cars or a spacious workshop. The generous acreage offers endless possibilities for enjoying the great outdoors, entertaining, gardening, recreation, or simply the peace and privacy that comes with having room to spread out. Bring your horses and your plans for a pool! This beautiful and unique property provides enough space for both.

1040 Drumcastle Lane, South Chesapeake

1523 Pucknall Drive, South Chesapeake
$335,000
3 Beds ⋅ 2.1 Baths ⋅ 10646628 MLS
Easy living awaits in this 3-bedroom, 2.5-bath condo in the heart of Greenbrier. The living room is filled with natural light and offers a warm, inviting feel from the moment you walk in. The large kitchen features plenty of cabinet and counter space, a walk-in pantry, and opens to the dining area, making everyday living and entertaining easy. A first-floor bedroom adds flexibility and convenience. Enjoy the private fenced patio, great for morning coffee, grilling, or relaxing outdoors. Upstairs, the primary suite offers a large walk-in closet and attached bath with a soaking tub and separate shower. The second upstairs bedroom also features an attached full bath and walk-in closet. A second-floor laundry room with sink adds extra convenience. Community amenities include a pool, yard maintenance, trash pickup, sewer and water. Conveniently located near shopping, dining, interstates, and more. Seller is offering closing costs assistance with an acceptable offer.

1523 Pucknall Drive, South Chesapeake

103 Ashley Road, South Chesapeake
$615,000
3 Beds ⋅ 3 Baths ⋅ 10643157 MLS
This beautifully updated brick home combines comfort, functionality, and style with flexible spaces designed for modern living. At the heart of the home, the stunning kitchen features a custom island perfect for gathering, entertaining, and everyday life. Spacious bedrooms, versatile living areas, and an expansive sunroom provide plenty of room to spread out, with ideal spaces for a home office, virtual learning, hobbies, or creative pursuits. A true standout feature is the oversized two-car garage/workshop, complete with a full bath and approximately 780 square feet of unfinished space above—offering endless possibilities for guest accommodations, a studio, home gym, office, or additional storage. Step outside to enjoy beautifully landscaped grounds, custom decking, and an inviting patio designed for entertaining. A charming custom she-shed adds even more versatility, along with an additional flex space inside the home. Thoughtful updates throughout and adaptable spaces are a win!

103 Ashley Road, South Chesapeake

2600 Saint Brides Road W, South Chesapeake
$570,000
4 Beds ⋅ 3 Baths ⋅ 10642916 MLS
Retreat to the expansive second-level primary suite, featuring a private sunroom, spacious loft, luxurious garden tub, separate tiled shower, and beautiful cherry hardwood flooring. The main level offers three additional bedrooms, two full bathrooms, and a generous sunroom complete with a built-in bar—perfect for entertaining or relaxing. Enjoy 3.16 acres of peaceful outdoor living, featuring a barn, chicken coop, and storage shed, offering endless possibilities for hobbies, animals, or gardening. Major updates provide peace of mind, including a new roof (2017), two-zone HVAC system (2020), and water heater (2023). Fresh interior paint throughout and brand-new downstairs carpet make this home truly move-in ready. Welcome Home!

2600 Saint Brides Road W, South Chesapeake

1260 Kidbrooke Street, South Chesapeake
$811,665
6 Beds ⋅ 5 Baths ⋅ 10615559 MLS
Welcome to The Summit, where you’ll discover thoughtfully designed living space across 2 luxurious floors. The main level impresses with a versatile 1st-floor bedroom and full bath, a flexible office or formal dining room, and a sunlit great room that flows seamlessly from the gourmet kitchen, featuring a large island, quartz countertops, soft-close cabinets, premium stainless steel appliances (including double ovens and a gas cooktop),and a walk-in pantry. Upstairs, unwind in your expansive owner’s suite with a huge closet, double vanities, a relaxing bathtub, and a separate shower, while three additional bedrooms, two full baths, a laundry room, and a loft provide ample space and flexibility. Enjoy a vibrant, amenity-rich community with walking trails and a fire pit, all within reach of Chesapeake’s scenic waterways, local festivals, and easy access to Virginia’s beaches and mountains-your ideal lifestyle begins here. The home is complete with a walk out basement.

1260 Kidbrooke Street, South Chesapeake

1240 Kidbrooke Street, South Chesapeake
$823,440
6 Beds ⋅ 5 Baths ⋅ 10615547 MLS
Welcome to The Summit, where you’ll discover thoughtfully designed living space across 2 luxurious floors. The main level impresses with a versatile 1st-floor bedroom and full bath, a flexible office or formal dining room, and a sunlit great room that flows seamlessly from the gourmet kitchen, featuring a large island, quartz countertops, soft-close cabinets, premium stainless steel appliances (including double ovens and a gas cooktop),and a walk-in pantry. Upstairs, unwind in your expansive owner’s suite with a huge closet, double vanities, a relaxing bathtub, and a separate shower, while three additional bedrooms, two full baths, a laundry room, and a loft provide ample space and flexibility. Enjoy a vibrant, amenity-rich community with walking trails and a fire pit, all within reach of Chesapeake’s scenic waterways, local festivals, and easy access to Virginia’s beaches and mountains-your ideal lifestyle begins here. The home is complete with a walk out basement.

1240 Kidbrooke Street, South Chesapeake

220 Deepwater Drive, South Chesapeake
$415,000
3 Beds ⋅ 2 Baths ⋅ 10645328 MLS
Rare opportunity to own on deep water in Chesapeake! Fish, kayak, boat right off your back dock. Keep your boat in your own backyard on the boat lift instead of paying for dry storage or slip fees. From your private dock, enjoy an approximate 40–50-minute cruise to the open waters of the Chesapeake Bay or to Downtown Norfolk’s vibrant Waterside District where waterfront dining, entertainment and marina amenities await you! Solidly built and full of potential, this classic brick ranch home offers 1,800 square feet of living space with 3 bedrooms and 2 full baths. Whether you’re looking to renovate, personalize or invest, this home provides a fantastic opportunity to make it your own. Being sold as-is, it is ready for your vision and your creativity! Call for more details or to schedule a private tour.

220 Deepwater Drive, South Chesapeake

900 Saddleback Trail Court, South Chesapeake
$470,000
4 Beds ⋅ 2 Baths ⋅ 10650269 MLS
Welcome to your new chapter, in this 4 bedroom, 2 bath ranch-style home situated on a massive 0.46 acre lot in the sought out Great Bridge school district. This move- in ready home has been freshly painted with new carpet and LVP flooring throughout. The room over the garage is massive and can serve as the 4th bedroom, man cave, home office or play room. Discover the perfect blend of comfort and space when you step in the open family room that has a wood burning fireplace and opens up to the huge kitchen that is full of natural lighting.The eat-in kitchen has a stainless steel stove, new stainless steel dishwasher, a nice size pantry and tons of natural light from the big Bay window. The master bedroom is huge with a large walk-in closet and a fully renovated bathroom with granite counter tops and all new fixtures. This home also features a 2 car garage with a new garage door and spacious driveway for your boat/ RV parking. We can't forget about the huge, privacy fenced in backyard with endless possibilities for your future cookouts, new pool or family gatherings. The well and shed convey as-is. Call today for your private showings!

900 Saddleback Trail Court, South Chesapeake

1225 Eagle Pointe Way, South Chesapeake
$466,000
3 Beds ⋅ 2 Baths ⋅ 10650137 MLS
Welcome to easy, elegant single-level living in this highly sought-after Fairmont plan in Eagle Pointe! This beautiful 3-bedroom home offers everything you need on one level. Enjoy a spacious two-story family room filled with natural light, a vaulted sunroom, dining room, and a well-appointed kitchen with beautiful cabinetry, stainless steel appliances, two pantries, and plenty of workspace. The spacious primary suite features TWO closets, including a large walk-in, plus a luxurious bath with double vanities, jetted tub, and separate shower. A generously sized laundry room adds even more convenience. Enjoy the Eagle Pointe lifestyle and Bay Club amenities, including indoor & outdoor pools, fitness center, library, game rooms, a full calendar of activities & social events. One-level homes in Eagle Pointe are always in demand... Schedule your tour today! Some photos have been digitally staged.

1225 Eagle Pointe Way, South Chesapeake

600 Winscott Court, South Chesapeake
$435,000
4 Beds ⋅ 2 Baths ⋅ 10648408 MLS
Welcome to this beautifully maintained all-brick ranch in the highly sought-after Hickory School District! Situated on a spacious corner lot, this home offers timeless curb appeal with an inviting covered front porch, attached garage, and a fully fenced backyard providing exceptional privacy for entertaining, pets, or play. Inside, you'll find a comfortable, functional floor plan featuring 3 bedrooms plus a finished room over the garage that serves perfectly as a 4th bedroom, home office, media room, or flex space to fit your lifestyle. The home has been lovingly cared for over the years and offers the perfect opportunity for its next owner to move right in while adding their own personal style and updates over time. Conveniently located near top-rated schools, shopping, dining, parks, and major commuting routes, this is your chance to own a solid, well-built home in one of Chesapeake's most desirable communities. Don't miss this incredible opportunity!

600 Winscott Court, South Chesapeake

1045 Winchester Way, South Chesapeake
$569,000
4 Beds ⋅ 2.1 Baths ⋅ 10645167 MLS
Beautifully updated and impeccably maintained, this exceptional 4BR/2.5BA home offers thoughtfully designed living space in the highly sought-after Kemp Woods neighborhood of Chesapeake. Nestled on a quiet, tree-lined street, this move-in ready home perfectly blends timeless elegance, quality craftsmanship, & modern updates. Step inside to an inviting floor plan filled with natural light, with rich hardwood flooring, elegant plantation shutters, and spacious living areas. Gourmet kitchen is designed to impress, featuring tall cabinetry, built-in appliances, abundant counter space, & oversized breakfast area surrounded by windows that fill the space with natural light. Spacious primary suite is a true private retreat, complete with large walk-in closet & stunning, spa-inspired ensuite featuring beautifully tiled, oversized frameless glass walk-in shower, dual vanity, designer lighting, & luxurious finishes that create a resort-like experience at home. 3 additional generously sized bedrooms. Seamlessly extending the living space outdoors, both the family room and breakfast area open to an expansive multi-level deck overlooking the private backyard. Designed for entertaining and everyday enjoyment, this outdoor retreat offers oversized deck and a hot tub—perfect for summer gatherings, peaceful evenings, or relaxing under the stars. Major improvements provide exceptional peace of mind, including a roof, two-zone HVAC system, & numerous updates completed within the last 5 years, allowing the next owner to simply move in and enjoy. Conveniently located just minutes from Greenbrier’s premier shopping, dining, entertainment, parks, hospitals, and major commuter routes including I-64, this home offers the perfect balance of convenience and the quiet charm of one of Chesapeake’s most established and desirable neighborhoods. Some photos were virtually staged or digitally enhanced for marketing purposes to help buyers visualize the property’s potential. Schedule your showing today to make this house YOUR HOME!!

1045 Winchester Way, South Chesapeake

2728 Blacksmith Trail, South Chesapeake
$410,000
4 Beds ⋅ 2 Baths ⋅ 10640949 MLS
An exciting opportunity to own this beautifully maintained home in highly sought-after Great Bridge! Welcome to this charming 4-bedroom,2-bath ranch nestled in an established Chesapeake neighborhood filled with mature trees,beautiful homes,& pride of ownership throughout. Offering the ease of one-level living,this move-in-ready home delivers the perfect blend of comfort,charm,& functionality in one of Great Bridge’s most desirable locations. Step inside to bright,inviting living spaces filled with natural light and designed for comfortable everyday living & effortless entertaining. This is the kind of home where holidays feel cozy,weekend gatherings come naturally,& everyday moments feel just a little sweeter. The thoughtful floor plan offers generous room sizes,a family-friendly layout,& abundant storage,giving everyone space to live,work,& unwind comfortably. Outside,the oversized backyard creates endless possibilities for backyard barbecues,kids at play,gardening,firepit nights,or simply relaxing after a long day. Whether hosting family celebrations or enjoying peaceful mornings with coffee outdoors,this outdoor space offers the lifestyle so many buyers are searching for. In a world where so many are craving more peace,more space,& more connection,this home delivers all three. Located near top-rated Great Bridge schools,shopping,dining,parks,& convenient interstate access,this Chesapeake home for sale offers the rare combination of location,space,& lifestyle. Ranch homes with large yards,one-level living,& this much charm in Great Bridge rarely become available. More than just a house,this is a place to slow down,spread out,& truly feel at home.

2728 Blacksmith Trail, South Chesapeake

429 Dupont Street, South Chesapeake
$485,000
4 Beds ⋅ 3.1 Baths ⋅ 10649056 MLS
This home packs a punch with over 2,600 square feet of living space situated on nearly half an acre! Updated throughout, this spacious home features 4 bedrooms & 3 full bathrooms, including two private ensuites. The 1st primary ensuite has a walk-in closet, a tiled shower with dual showerheads & oversized vanity. The 2nd primary bedroom has been divided to make a 5th bedroom; both are generously sized. The kitchen is equipped with newer appliances (2025). The flexible floor plan also offers a versatile office or craft room/flex space. Enjoy the covered patio leading to the large, fully fenced backyard with a chicken coop already in place, perfect for those ready to embrace a bit of country living . The 2-car attached garage and extended driveway provides plenty of parking and additional storage. With generous living space, multiple ensuite bedrooms, thoughtful updates, and a versatile layout, this move-in-ready home has so much to offer!

429 Dupont Street, South Chesapeake

1720 Barkadeer Cove, South Chesapeake
$440,000
3 Beds ⋅ 2.1 Baths ⋅ 10648817 MLS
Welcome to Bryan's Cove, where low-maintenance living meets exceptional community amenities in the heart of Chesapeake. This beautifully maintained townhome features a first-floor primary suite and an open-concept layout designed for both everyday living and entertaining. The kitchen offers stainless steel appliances, a pantry, peninsula seating, subway tile backsplash, and opens to the dining area and spacious living room highlighted by a custom floor-to-ceiling shiplap fireplace with floating wood shelving. The heated and cooled sunroom provides additional year-round living space, while luxury vinyl plank flooring, a custom frosted glass barn door leading to the primary bath, premium window treatments, and a smart thermostat add thoughtful style and convenience throughout. Outside, enjoy a fully fenced backyard with a stamped concrete patio, pergola, professional landscaping, and attached 2-car garage. Bryan's Cove offers resort-style amenities including a clubhouse, pool, fitness center, playgrounds, and access to the Elizabeth River, all with no flood insurance required. Conveniently located near shopping, dining, interstates, and military bases, this home is ready for its next owner. Incentives may be available through preferred partners. Contact listing agent for details and eligibility. Some photos are virtually staged.

1720 Barkadeer Cove, South Chesapeake

432 Charleston Street, South Chesapeake
$390,000
3 Beds ⋅ 2.1 Baths ⋅ 10644759 MLS
Welcome home to this beautifully maintained townhome in the highly desirable Great Bridge area of Chesapeake! This spacious 3-bedroom, 2.5-bath home offers the perfect blend of comfort, style, and convenience. The open-concept floor plan is filled with natural light and features gleaming wood floors, granite countertops, stainless steel appliances, and crisp white cabinetry. The primary suite boasts a granite vanity and dual shower heads for a spa-like retreat. Pride of ownership shines throughout with a fresh interior paint refresh and a newly installed backyard gravel area, creating a low-maintenance outdoor space perfect for relaxing or entertaining. Complete with an attached garage and driveway parking, this move-in ready home is ideally located just minutes from shopping, dining, top-rated schools, parks, military bases, hospitals, and the area’s beautiful beaches. Don’t miss the opportunity to own this well-cared-for home in one of Chesapeake’s most sought-after communities!

432 Charleston Street, South Chesapeake

1456 Debbs Lane, South Chesapeake
$411,000
3 Beds ⋅ 2 Baths ⋅ 10649551 MLS
Location, location, location! Just off Volvo Parkway, this meticulously maintained ranch offers exceptional convenience to interstates, Chesapeake, Virginia Beach, shopping, dining, and more. Featuring 3 bedrooms and 2 baths, this move-in-ready home boasts a newly renovated primary bath with custom tile shower, granite kitchen with stainless steel appliances, and a cozy great room with vaulted ceiling and wood-burning fireplace. Updates galore include roof and attic spray insulation (2026), garage door and opener (2025), washer (2024), dryer (2025), and fireplace inspection (2025). Enjoy outdoor living with a pool featuring a 2026 pump, liner, and cover, plus Trex decking, pavers, hardscaping, and artificial turf. Fresh paint and an expanded driveway complete this beautifully updated, centrally located home!

1456 Debbs Lane, South Chesapeake

912 Scarlet Oak Court N, South Chesapeake
$315,000
3 Beds ⋅ 2 Baths ⋅ 10647026 MLS
Discover the possibilities in this charming ranch style home with great bones and a functional, single-level layout. Tucked away on a quiet double-ended cul-de-sac in the highly sought-after Greenbrier area, this home features a fully privacy-fenced backyard, spacious deck, and storage shed, creating plenty of room to relax, entertain, garden, or design your own outdoor retreat. The former garage was converted to create one bedroom and one full bath, completing the home’s now practical 3-bedroom, 2-bath floor plan. Bring your vision and personal touch to update the finishes, make the space your own, and build sweat equity along the way. Conveniently located near shopping, dining, highways, interstate access, military bases, and area beaches. Offered as-is and ready for its next chapter.

912 Scarlet Oak Court N, South Chesapeake

2000 Long Ridge Road, South Chesapeake
$1,175,000
5 Beds ⋅ 3 Baths ⋅ 10646791 MLS
Rare opportunity to own a Chesapeake equestrian property offering the perfect blend of refined country living and modern convenience. This exceptional home offers 5 bedrooms, 3 full bathrooms, 3,046 square feet, and an additional 712 square feet of living space in a true in-law suite with private entrance. Equestrian enthusiasts will appreciate three fenced pastures, a riding ring with light, the run-in shed, and a three-stall stable with tack room, while the outdoor enthusiast will love the large garden, the raised garden beds, the blueberry and raspberry bushes, the gazebo, and the picturesque koi pond with fountain. Inside, the living room with beautiful stone mantle and pellet stove is open to the updated kitchen featuring gorgeous, leathered granite countertops, a large island, and an eat-in area with additional cabinetry. The spacious primary suite offers beautiful property views and includes a walk-in closet and luxurious bath with double quartz shower and dual sinks. Additional highlights include wood floors throughout, an office with French doors, a fantastic screened-in porch and a deck, a 2-car attached garage, a 3-car detached garage, a new well, reverse osmosis water system, generator hook-up, and a 400-gallon propane tank. The best of country living without sacrificing modern convenience, this country retreat is designed for both comfortable living and equestrian enjoyment.

2000 Long Ridge Road, South Chesapeake

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