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$825,000
5 Beds 2.1 Baths 10646792 MLS
Space to gather, land to enjoy, and a separate apartment for the people who matter most. Nearly 3,900 square feet in the main home, 3 private acres, a detached three-car garage, and an approximately 1,000-square-foot apartment above it. This sprawling ranch offers four first-floor bedrooms, including the spacious primary suite with dual closets, beautifully refinished hardwoods, fresh paint, updated lighting, newer roof, new carpet and an expansive kitchen with gas cooking and newer appliances. A finished bonus room upstairs serves as the fifth bedroom or flexible space for guests, hobbies, or a quiet retreat. An enormous walk-in attic provides rare expansion potential, with room to add finished living space for an even more complete upstairs retreat. Enjoy the new Trex deck and peaceful backyard with room to entertain, garden, play, and bring your horses-picture them grazing outside your kitchen window while your coffee brews. Dreaming of an inground pool and backyard oasis? There is room for that too. Need space for your in-laws? Above the detached garage, the separately metered apartment includes its own bedroom, full bath, kitchen, living area, and laundry, creating true independent space for extended family, guests, a studio, or private home office. The apartment is not counted in sq ft/bedroom/bath count in this listing. Well and septic mean no monthly city water or sewer bill. Located in Riverwood, a quiet acreage community known for spacious homesites, mature trees, room for horses, and a neighborhood boat launch for enjoying nearby waterways. Enjoy the space and privacy of South Chesapeake in the Grassfield school district. Come see the lifestyle you have been searching for.

3700 Riverwood Crescent, South Chesapeake

$520,000
4 Beds 2 Baths 10646823 MLS
Welcome to your oasis in Great Bridge, a beautifully maintained home tucked away on a quiet cul-de-sac in one of Chesapeake?s most desirable communities. This spacious property offers comfortable living with bright, inviting interiors, a functional floor plan, and generous living spaces perfect for everyday life and entertaining. Step outside to your private backyard oasis featuring an in-ground pool, ideal for relaxing or hosting family and friends. In addition to the attached garage, a second detached garage provides exceptional space for vehicles, a workshop, hobbies, or extra storage. Situated on a cul-de-sac and conveniently located near top-rated schools, shopping, dining, parks, and major commuter routes, this home offers the perfect combination of privacy, functionality, and convenience.

813 Woodrow Court, South Chesapeake

$430,000
3 Beds 2.2 Baths 10646321 MLS
Built in 2022, this move-in-ready end-unit townhome in the sought-after Bryan's Cove community offers the perfect blend of modern design, comfort, and convenience. This three-story home features a flexible first-floor bonus room ideal for a home office, gym, or guest suite, plus an attached two-car garage. The open-concept main level is filled with natural light and showcases a gourmet kitchen with granite countertops, stainless steel appliances, a large center island, and an adjoining dining area with access to a private balcony—perfect for relaxing or entertaining. Upstairs, the spacious primary suite features a tray ceiling, walk-in closet, dual vanities, a soaking tub, and separate shower. Enjoy resort-style amenities including a clubhouse, fitness center, swimming pool, dog parks, playgrounds, pier, and docks. Conveniently located near shopping, dining, military bases, and major interstates, this low-maintenance townhome offers exceptional value and an unbeatable lifestyle.

1732 Defiance Drive, South Chesapeake

$599,900
4 Beds 2.1 Baths 10646724 MLS
Welcome to this beautiful move in ready Stephen Alexander home, nestled on a cul-de-sac lot in the highly sought-after Grassfield School District in Great Bridge. Enjoy relaxing on the charming front porch or entertaining on the spacious new deck. Inside, you'll find an open floor plan with hardwood floors, a family room with a gas fireplace, a spacious kitchen with a center island, a formal dining room, and a versatile bonus room perfect for a home office, playroom, or flex space. The oversized primary suite offers a private retreat with an en-suite bath, while the additional bedrooms provide plenty of room for family or guests. Updates include: Roof (2022), Windows (2019), Water Heater (2020), HVAC serviced (2026), gas fireplace serviced and kitchen appliances (2022). Conveniently located near shopping, dining, and interstates, this home offers the perfect blend of comfort, style, and location. Schedule your private tour today! Seller is offering 1 year home warranty. Assumable loan at 2.5% for qualified buyers, subject to lender approval.

1102 Watsons Glen Court, South Chesapeake

$559,000
5 Beds 3 Baths 10646652 MLS
This is classic Great Bridge living at it's best! Nestled on a quiet cul-de-sac in the desirable Southern Pines neighborhood, this beautifully maintained 5-bedroom, 3-bath home offers 2,491 square feet of versatile living space on a private, half-acre wooded lot. A standout feature is the in-law suite, complete with its own bedroom, attached sitting/living area, and full bath ideal for multigenerational living or long-term guests. Two bathrooms have been tastefully renovated, while the newer roof and replacement windows provide added peace of mind. The cozy living room features a gas log/wood-burning fireplace, and the finished room over the garage offers endless flexibility as a bedroom, playroom, media room, or home office. Relax on the welcoming front porch or entertain on the spacious rear deck overlooking the peaceful backyard. Complete with a 2-car attached garage, detached storage shed, and no HOA.

529 Wittington Drive, South Chesapeake

$625,000
4 Beds 2.1 Baths 10646683 MLS
Nestled in one of the area's most desirable neighborhoods, this stunning home offers over 3000 sq ft of beautifully designed living space. Step inside to an inviting floor plan featuring a spacious living room with soaring cathedral ceilings and a gorgeous stone fireplace. The large eat in kitchen flows seamlessly to the living area with ample cabinetry, a brand-new kitchen sink, plenty of space for entertaining. This spacious 4-bedroom home also features a versatile flex room off the foyer, great for a home office or den. Retreat to the expansive primary suite through French doors, where you will find a generous walk-in closet & a en-suite bath designed for comfort and relaxation. All new windows 2024 and a new HWH. Outside, you'll love the newer deck and fenced in yard. Cheshire Forest residents enjoy exceptional lifestyle amenities including a neighborhood pool, the flying fish swim team, clubhouse, playgrounds, tennis & pickleball courts, pond for fishing & scenic walking paths.

609 Edgewood Arch, South Chesapeake

$995,000
6 Beds 4 Baths 10645935 MLS
An exceptional opportunity to own a Stephen Alexander custom home in Greystone, one of Chesapeake's premier luxury communities where homes are rarely available. This expansive executive residence blends timeless craftsmanship with the space, flexibility, and resort-style amenities today's luxury buyers seek. A first-floor bedroom with an adjacent full bath offers versatility for guests, a home office, or multi-generational living. The primary suite is a true retreat with a fireplace, sitting area, and four closets. Enjoy a private backyard oasis featuring an in-ground pool, hot tub, screened porch, gazebo, fire pit, privacy fence, irrigation well, and expanded parking for a boat or RV. Scenic walking paths enhance this sought- after community. Significant recent investments include a new roof (2026), three HVAC systems, an encapsulated crawl space, new hardwood flooring, updated bath vanities, freshly painted kitchen cabinetry, and a new oven. Schedule your private showing today!

821 Redleafe Circle, South Chesapeake

$560,000
4 Beds 2 Baths 10646286 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

$750,000
6 Beds 3.1 Baths 10646118 MLS
Spacious 4,899 sf lakefront home offering 6 bedrooms and 3.5 baths with an exceptional floor plan designed for comfortable living and entertaining. The expansive 1st floor primary suite provides a private retreat, while a 2nd floor ensuite is great for guests or multigenerational living. A massive great room with stunning lake views serves as the heart of the home, flowing seamlessly to a large composite deck great for outdoor gatherings. The oversized 840 sf attached garage offers ample space for vehicles, storage and hobbies. A walk-up attic provides abundant storage or future expansion potential. With generous living spaces, beautiful water views and a great price, this home is ready to accommodate every lifestyle.

1548 Waterside Drive N, South Chesapeake

$700,000
5 Beds 2.1 Baths 10645293 MLS
Tucked away on a quiet cul-de-sac, this beautifully maintained custom home offers the perfect combination of quality construction, thoughtful upgrades, and everyday comfort. Built in 2004 and offering approximately 3,300 square feet, this all-brick home features 5 bedrooms, with 4 conveniently located on the first floor, providing exceptional flexibility for families, guests, or multi-generational living. From the moment you step inside, you'll appreciate the soaring cathedral ceilings, spacious living areas, and inviting gas fireplace that create a warm and welcoming atmosphere. The private primary suite offers a relaxing retreat with a jetted soaking tub and generous walk-in closets. One of this home's standout features is the incredible backyard privacy. Whether you're enjoying your morning coffee, hosting family and friends on the large deck, or simply unwinding after a long day, you'll love the peaceful setting and the feeling of having your own private oasis. This home also offers valuable upgrades that provide peace of mind for years to come. A whole-house generator ensures you're prepared and comfortable during unexpected power outages and reflects the care and attention given to maintaining the home. An irrigation system keeps the lawn looking its best with minimal effort. Located in the highly sought-after Hickory school district, this home delivers the rare combination of timeless all-brick construction, flexible living space, exceptional privacy, and important long-term investments that today's buyers appreciate. If you've been searching for a home that is as practical as it is beautiful, this one is not to be missed. Some photos have been virtually staged.

1104 Arabian Arch, South Chesapeake

$510,000
4 Beds 2.1 Baths 10645829 MLS
WELCOME HOME! Tucked away on a quiet cul de sac and set on nearly an acre backing to peaceful woods, this beautifully maintained home offers the perfect blend of privacy, outdoor living, and everyday convenience. Whether you’re enjoying your morning coffee in the screened gazebo or entertaining family and friends, you’ll appreciate the peaceful setting this property provides. Inside, you’ll find stainless steel appliances, a spacious walk in pantry, a cozy gas fireplace, and thoughtful updates throughout, including a new roof installed in 2024. A transferable 2-10 Home Warranty provides added peace of mind for the next owner. Conveniently located near Interstate 64, Route 17, shopping, dining, and major military installations throughout Hampton Roads, this home offers the ideal balance of tranquility and accessibility. Don’t miss your opportunity to make this exceptional property your next home. Schedule your private showing today!

104 Bishops Court, South Chesapeake

$479,900
4 Beds 2 Baths 10645772 MLS
Welcome to this spacious 4-bed, 2-bath home situated on a beautiful half-acre lot in the heart of Great Bridge! Offering a flexible floor plan, this home features 2 oversized living areas, 2 spacious primary bedrooms, & 2 additional bedrooms—ideal for multigenerational living, a home office, playroom, or the potential for a 5th bedroom. Updates include fresh interior paint, new flooring, restored hardwood floors, & renovated bathrooms. The updated kitchen offers new countertops, ample cabinet space, & a cozy breakfast nook. Step outside to the covered deck overlooking the expansive backyard, providing plenty of room for entertainment, gardening, pets, or future outdoor additions. Located in the highly desirable Great Bridge school district, you’ll enjoy the convenience of being just minutes from shopping, restaurants, & everyday amenities. Don’t miss this rare opportunity to own a move-in-ready home with space, flexibility, & an unbeatable location. Schedule your showing today!

145 Hurdle Dr Drive, South Chesapeake

$699,900
4 Beds 4 Baths 10645397 MLS
Welcome home to Rollingwood Estates in the highly sought after Great Bridge school district. This one owner brick transitional home offers 4 bedrooms and 4 full baths with an open, bright floor plan designed for comfortable living and effortless entertaining. The spacious FROG serves as the fourth bedroom and features its own private full bath, making it ideal for guests or multigenerational living. The kitchen offers Corian countertops, generous workspace and opens to the main living areas. Step outside to your own backyard retreat with a sparkling inground pool, dedicated pool bath, stamped concrete patio, outdoor bar/kitchen area, screened porch, and professionally landscaped yard. A two car attached garage, irrigation well, and thoughtful layout add to the appeal. Offering exceptional value in an established neighborhood, this home is priced to sell and ready for its next owner to make it their own.

837 Greenfield Lane, South Chesapeake

$629,000
6 Beds 3 Baths 10645483 MLS
Rare 6-bedroom opportunity with an ideal multigenerational layout! The first floor features a bedroom, adjacent flex room, and a modified curbless shower, offering exceptional flexibility and accessibility. Beautiful neutral decor, 9' ceilings, hardwood floors, elegant crown molding, and a huge FROG provide room for everyone. The spacious primary suite features hardwood floors and two walk-in closets. Convenient second-floor laundry. Enjoy a large fenced backyard with a detached shed and private well for economical lawn irrigation, plus an attached 2-car garage. Meticulously maintained with annual service contracts on the HVAC, tankless water heater, and crawl space. Seller will provide a termite/moisture letter. Convenient to Millville Rd., Veterans Bridge.

1816 Sunsprite Loop, South Chesapeake

$529,900
4 Beds 2.1 Baths 10645403 MLS
You have seen the pictures and now I am sure you are curious about everything this house has to offer. Well, it is absolutely 100% turn-key, move-in ready with all of the bells and whistles. The home feels so good and invites tons of natural light. The kitchen has been thoughtfully remodeled adding tons of cabinet space, a center island, a pot filler and more functional layout. The cabinets, flooring (hand scraped bamboo), counters and appliances have all been recently upgraded as well. The bathrooms have all been remodeled and the primary bath is a small piece of heaven. Separate sinks, dual shower heads in the tile/glass shower and a separate soaking tub. Go outside and you might not go back in for quite a while. A covered porch and expansive deck greet you with the hot tub around the corner. Drop down to the 28,000 gallon in-ground pool complete with a built-in endless pool for serious swimmers. Backing up to the woods, this private, backyard paradise awaits you!

2107 Sunset Maple Lane, South Chesapeake

$579,000
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

$765,000
5 Beds 2.1 Baths 10645076 MLS
Why wait on new construction when this one's already done? This home was taken all the way down to the foundation and completely rebuilt and expanded — outside of one corner of the home everything here is new. Home inspection is complete, every item addressed, so you can move in with genuine peace of mind. Tucked away on a quiet country road in Chesapeake and surrounded by 3 peaceful acres of mature trees, this modern farmhouse ranch offers the privacy and charm buyers dream about. Huge wraparound-feel porches front and back give you outdoor living space to spare, and the wide-open yard makes this property feel like a true retreat. Inside, gorgeous LVP flooring flows throughout, while the spacious living area with a stunning brick fireplace creates a warm gathering space. The farmhouse-inspired kitchen features white cabinetry, an oversized island with bar seating, and ample storage. Bedrooms are thoughtfully spaced for added privacy, while the hall bath offers a double vanity, step-in shower, and beautiful natural light. The primary suite feels like its own getaway, with private porch access, dual closets, and a spa-style bath featuring a floor-to-ceiling marble-tiled shower. A detached storage shed conveys, and the sprawling backyard offers endless possibilities — gardening, entertaining, or future additions. All the character of country living, with the peace of mind of a brand new home. Welcome home.

1629 Shillelagh Road, South Chesapeake

$325,000
3 Beds 2 Baths 10644838 MLS
Discover single-level living at its finest in this charming Chesapeake ranch! Perfectly positioned on a generous corner lot, this 3-bedroom, 2-bath home boasts a bright and open atmosphere. The spacious living area flows seamlessly into a fully updated kitchen featuring modern appliances, a moveable island, and a cheerful breakfast nook. Down the hall, the primary suite offers a peaceful everyday escape, highlighting a beautifully updated closet and an inviting en-suite bathroom. The two additional bedrooms provide endless flexibility to suit your lifestyle. The outdoor space is a true highlight, featuring a brand-new deck that overlooks a spacious yard with endless possibilities for gardening or relaxing. With a new water heater already installed and a prime location near local parks, top-rated schools, and vibrant shopping, this home is completely turnkey!

1553 Forest Cove Drive, South Chesapeake

$305,000
2 Beds 1 Baths 10644942 MLS
Welcome home to this charming all brick ranch nestled in Brentwood Estates neighborhood. This well-maintained home offers the perfect combination of classic charm and thoughtful updates making it truly move-in ready. Inside you will find a beautifully updated bathroom. The kitchen provides abundant cabinetry, and the dining room has been enhanced with new windows, elegant chandelier creating a nice setting for family dinners. All appliances convey. Enjoy peace of mind with updated roof, windows (2017), along with a brand-new sidewalk, garage floor and driveway offering exceptional curb appeal. Step outside to a large, fully fenced backyard complete with a covered deck, an ideal space for relaxing, grilling and entertaining family & friends.

2209 Wildwood Road, South Chesapeake

$550,000
4 Beds 3 Baths 10644867 MLS
Welcome home to this beautiful Craftsman-style ranch in highly desirable Culpepper Landing! This spacious 4-bedroom, 3-bath home offers approximately 2,380 square feet of thoughtfully designed living space with an open floor plan, soaring 10-foot ceilings, hardwood floors, upgraded trim, and surround sound in the living room. The gourmet kitchen features granite countertops, custom cabinetry, a large center island with bar seating, and ample storage—perfect for large families or entertaining. The first-floor primary suite offers a tray ceiling, walk-in closet, and an ensuite bath with double vanities, a garden tub, and a tiled walk-in shower. A finished room over the garage with a full bath and walk-in closet provides the perfect guest suite, home office, or flex space. Enjoy relaxing on the inviting front and side porches or entertaining on the rear deck. Additional features include a two-car attached garage, sprinkler system, and garage door opener with a transferable warranty and MyQ smart access for convenient remote operation and secure package delivery. Inground Sprinkler System has recently been inspected, a new back flow preventer was added and sprinkler heads relocated to accommodate a future fence. Interior professionally painted, new easy open window blinds installed thoughout w/4 yr warranty (2025). Located across from the neighborhood dog park, Culpepper Landing offers outstanding amenities including a clubhouse, community pool, fitness center, playgrounds, and walking trails, all with convenient access to shopping, dining, military bases, and major interstates.

3209 Dodd 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.