South Chesapeake Homes for Sale

Welcome to South Chesapeake, Virginia – a hidden gem nestled within the vibrant Chesapeake County. Known for its lush landscapes and welcoming community, South Chesapeake offers a harmonious blend of suburban tranquility and urban convenience. With its prime location, residents enjoy easy access to the bustling cities of Norfolk and Virginia Beach, making it an ideal spot for both work and play.

South Chesapeake boasts a rich tapestry of recreational opportunities, from serene parks and scenic trails to local shops and delightful dining options. Families can take advantage of the top-rated schools in the area, ensuring a bright future for their children. The friendly neighborhoods are perfect for those looking to connect with neighbors and build lifelong friendships.

For homebuyers, South Chesapeake presents an array of homes for sale that cater to diverse tastes and budgets. Whether you’re seeking a charming single-family home with a sprawling yard, a modern townhouse with urban flair, or a cozy cottage perfect for first-time buyers, you’ll find it all here. Many properties feature spacious living areas, updated kitchens, and beautiful outdoor spaces, making them perfect for both relaxation and entertaining.

With a strong sense of community and a wealth of amenities, South Chesapeake is more than just a place to live; it’s a place to thrive. Explore the homes for sale today and discover why so many choose to call South Chesapeake home. Your dream home awaits in this enchanting corner of Virginia!

Newest South Chesapeake Homes for Sale

$540,000

4 Beds ⋅ 2.1 Baths ⋅ 10646908 MLS

Beautifully updated 2-story traditional home tucked away on a quiet cul-de-sac in Chesapeake's desirable Greenbrier area! This move-in-ready home offers 4 bedrooms, 2.5 bathrooms, and an attached 2-car garage. The main level features formal living and dining rooms, a spacious family room, half bath, utility/laundry room, and an inviting kitchen with a Butler's pantry. Laminate flooring flows through the living, dining, and family rooms, while new tile flooring enhances the kitchen, bathrooms, and laundry room. Fresh interior paint throughout and brand-new carpeting upstairs provide a modern, refreshed feel. The spacious primary suite includes a walk-in closet and private ensuite bath. Conveniently located just minutes from Greenbrier Mall, shopping, dining, Chesapeake City Park, the Chesapeake Arboretum, and major commuter routes including I-64, I-464, and Route 168. Don't miss this exceptional opportunity!

800 Crescent Trace, South Chesapeake

$675,000

5 Beds ⋅ 3 Baths ⋅ 10646827 MLS

Welcome to Viridian Reserve at Hickory, where comfort, space, and peaceful wooded views come together in one exceptional South Chesapeake home. From the moment you step inside, you'll be greeted by soaring cathedral ceilings, an inviting multi-landing staircase, and a warm, open layout designed for everyday living and entertaining. The spacious family room features a cozy gas fireplace, while the incredible kitchen is truly the heart of the home, offering beautiful wood cabinetry, an abundance of cabinet space, updated appliances, and a convenient wine/beverage refrigerator. The formal dining area provides plenty of room for gatherings, and the first floor also includes a private office, a bedroom, and a full bathroom, great for guests, multigenerational living, or working from home. Upstairs, the oversized primary suite is a true retreat with room for a sitting area, three closets, and a luxurious ensuite bath featuring granite countertops, dual vanities, a walk-in shower, private water closet, and an additional spacious walk-in closet. Outside, enjoy relaxing on the charming covered porch overlooking the large backyard with peaceful wooded views, with the option to easily screen it in for year-round enjoyment. The oversized two-car garage offers exceptional storage, a built-in workbench, and plenty of room for hobbies, while the extended driveway provides additional parking. Located in the highly desirable Hickory area, this home offers the perfect combination of space, functionality, and privacy.

308 Wisdom Path, South Chesapeake

$569,900

4 Beds ⋅ 2.1 Baths ⋅ 10646819 MLS

Welcome to this beautifully maintained 4 bedroom, 2 and a half bath, all-brick ranch in the Grassfield School District of Chesapeake. This home features updated eat-in kitchen to include granite counter tops, stainless steel appliances (KitchenAid Refrigerator), gas range, shaker cabinets, and fresh paint. Enjoy an open layout with a very spacious great room, vaulted ceilings and a gas fireplace. French doors offer privacy to the formal dining, living room/office. Stunning bamboo floors throughout the kitchen and living areas. The large finished bedroom over the garage offers new LVP flooring, lighting, shelving, built in reading nook or can be used as a bed. Major system upgrades include TRANE HVAC system installed in 2021 with duct work replaced and system zoned in 2025. RainSoft reverse osmosis, enclosed crawl space with dehumidifier, insulated garage doors, updated vents and a newer gas water heater. Half bath located next to the mudroom/laundry room, washer & dryer to convey. New carpet in all main floor bedrooms. Enjoy outdoor living on your covered front porch or in your private fenced in backyard and deck. Expansive attic space for storage and extended driveway for additional parking. A truly move-in-ready Chesapeake home, minutes to shopping, dining, and interstate access. Please ask for the detailed upgrade list of extensive repairs and improvements. The home has been meticulously maintained with major system updates throughout.

817 Doe Run Drive, South Chesapeake

$675,000

5 Beds ⋅ 3 Baths ⋅ 10646878 MLS

Welcome home to this spacious 5-bed, 3-bath home offering 3,842 sq ft of beautifully designed living space on a generous .84-acre lot. With multiple living areas, a HUGE bonus room over the garage, plus a formal living room, dining room, family room, and bright sunroom, there's plenty of space to spread out. The open kitchen flows seamlessly into the family room and sunroom. Upstairs, the spacious primary suite boasts a spa-like bath with a jetted tub, separate shower, and dual vanities. Brand-new carpet was installed upstairs. Step outside to your private backyard retreat featuring a Trex deck, outdoor kitchen, stamped concrete patio, and an expansive fenced yard with a newer vinyl privacy fence with four gates. A storage shed with power provides plenty of extra storage. Additional highlights include stunning curb appeal, a stamped concrete driveway, epoxy-coated garage floor, EV charger, and easy access to military bases, major highways, shopping, dining, and entertainment.

3204 Hearring Way, South Chesapeake

$674,900

5 Beds ⋅ 3.1 Baths ⋅ 10646835 MLS

If you've been searching for a spacious, move-in-ready home with a private in-law suite on a large lot in the heart of Chesapeake, your search is over! This one-of-a-kind property offers the blend of comfort, flexibility, and space. The traditional in-law suite features its own multiple entrances, full kitchen, living room with a cozy gas fireplace, recently remodeled bathroom, bedroom, and dedicated laundry area—use for multi-generational living or extended guests. Step outside to a large backyard for relaxing or entertaining, complete with a recently built gazebo with electricity and a storage shed for all your gardening and outdoor needs. Located in a neighborhood with sought-after schools, you'll enjoy convenient access to shopping, dining, parks, and more. Don't miss this rare opportunity to make this exceptional Chesapeake home yours!

1307 Channing Way, South Chesapeake

$390,000

3 Beds ⋅ 2 Baths ⋅ 10646455 MLS

Beautifully reimagined ranch home with designer-inspired finishes throughout! Offering 1,482 square feet, this exceptional residence features 3 bedrooms, 2 beautifully updated baths, and a versatile bonus room ideal for a home office, playroom, guest space, or hobby room. The stunning kitchen showcases new custom-style cabinetry, elegant granite countertops, and brand-new stainless steel appliances, including a dishwasher, range, microwave, and disposal. Matching granite countertops extend into the bathrooms, which have been tastefully renovated with stylish new tile finishes. Additional upgrades include a new roof, new windows, new HVAC system, new water heater, new interior doors, fresh interior paint, and new flooring throughout. Blending timeless style with modern updates, this turnkey home offers comfort, quality, and exceptional value. Don't miss out, schedule your showing today!

716 Baywood Trail, South Chesapeake

$484,900

4 Beds ⋅ 2.1 Baths ⋅ 10646662 MLS

Beautifully maintained 4-bedroom, 2.5-bath home featuring a versatile floor plan with multiple living spaces and an oversized finished room over the garage (FROG), ideal as a 4th bedroom or flexible bonus space. The main level offers a welcoming foyer, formal living room, formal dining room, spacious family room with a gas fireplace, and a bright breakfast area adjoining the kitchen. Upstairs you'll find three additional bedrooms, the oversized FROG or 4th bedroom, and a conveniently located laundry room. Relax on the covered rear deck overlooking the fully fenced backyard with mature landscaping, irrigation system, and storage shed. Thoughtful updates by the current owner include a roof, replacement windows, an encapsulated crawl space with dehumidifier, water heater, dishwasher, and updated gutters. A portion of the rear deck is currently being replaced. No HOA. Flood Zone X. Convenient to shopping, restaurants, schools, military bases, and major highways.

420 Brandon Way, South Chesapeake

$825,000

5 Beds ⋅ 2.1 Baths ⋅ 10646792 MLS

An exceptional setting for the way you want to live. 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 provides a 5th bedroom 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, on land zoned to make it real. 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. Well and septic mean no monthly city water or sewer bill. 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

$665,000

5 Beds ⋅ 2.1 Baths ⋅ 10646600 MLS

LUXURY COASTAL RESORT STYLE RIVER FRONT COMMUNITY! Welden Field & Rowe Custom Home on a Premium .44-acre lot backs to Nature Preserve. Resort like lifestyle w/ waterfront Gazebo, deep water access, Kayak launch, Clubhouse, Pool, Fitness Room, Green Space, Nature Preserve w/Trails. Welcome to this meticulously maintained Craftsman-style home w/ Southern Living front porch & thoughtfully designed luxurious light-filled floor plan. Chef's kitchen w/ expansive island, bar seating, Dual-Fuel Range, tile back splash tile backsplash & Cafe SS appliances. Comfortable open living spaces that flow seamlessly throughout w/fireplace, 8 ft doors, high ceilings. Spacious downstairs owner's suite w/ Spa concept bathroom, tile floors, glass shower, over-sized Garden tub + custom walk-in closet + FF guest bedroom/Home Office w/ add storage. Outdoor oasis that backs to Nature Preserves w/ spacious covered porch, irrigation system, back up generation & MORE! Easy access to I-64, Edinburgh. WELCOME HOME!

409 Tranquility Trace, South Chesapeake

$720,000

5 Beds ⋅ 3 Baths ⋅ 10646838 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

$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

$489,900

4 Beds ⋅ 2.1 Baths ⋅ 10646630 MLS

Beautiful, brick front, 4 bedroom home in sought after Greenbriar Estates. The newly renovated kitchen boasts SS apliances, new cabinets, Quartz counters with a large island that is open to the family room. Other features include an architectural roof, wood floors, HVAC and wood floors all replaced approximately 5 years ago! The large primary suite features a walk-in closet, dual sinks, a separate soaker tub, a skylight and a custom glass shower door.LOCATION-LOCATION! Less than 30 minutes to Naval Station Norfolk & little creek bases, as well as the Virginia Beach Oceanfront .Chesapeake City Park is at the end of the street, and Greenbriar Mall is just minutes away. Schedule your showing soon, this one won't last!

602 Windward Drive Drive, South Chesapeake

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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.