South Chesapeake Homes for Sale

Welcome to South Chesapeake, Virginia—a vibrant community that beautifully blends suburban charm with the allure of nature. Nestled within the picturesque Chesapeake County, this region offers a unique lifestyle that appeals to families, professionals, and retirees alike. With its lush green parks, scenic waterways, and friendly neighborhoods, South Chesapeake is a haven for those seeking a tranquil yet connected way of life.

One of the standout features of South Chesapeake is its convenient access to major highways, making commuting to nearby cities like Norfolk and Virginia Beach a breeze. Residents enjoy a variety of shopping, dining, and entertainment options, with local boutiques and restaurants that showcase the region's rich culture. The area is also home to top-rated schools and numerous recreational facilities, ensuring that families have everything they need right at their fingertips.

When it comes to homes for sale in South Chesapeake, the options are as diverse as the community itself. From charming single-family homes with spacious backyards to modern townhouses and cozy condos, there’s something to suit every taste and budget. Many properties boast beautiful landscaping and proximity to parks, while others offer stunning waterfront views. Whether you’re a first-time buyer or looking to upgrade, South Chesapeake’s real estate market is thriving, providing ample opportunities for homeownership.

Explore the inviting neighborhoods of South Chesapeake today and discover the perfect place to call home. With its warm community spirit and beautiful surroundings, you’ll find that life here is not just about living; it’s about thriving.

Newest South Chesapeake Homes for Sale

$524,900

4 Beds ⋅ 2.1 Baths ⋅ 10653645 MLS

Well-maintained 4-bedroom home featuring an open floor plan and beautiful hardwood flooring throughout the main living areas. The spacious kitchen offers 42-inch cabinetry, granite countertops, a center island, stainless steel appliances, and plenty of workspace for everyday living and entertaining. Generously sized bedrooms include a spacious primary suite with a private bath and jetted tub. The open layout provides a comfortable flow between the kitchen and living spaces. Outside, enjoy a large fenced backyard with plenty of room for outdoor entertaining, recreation, or relaxing. Located in the Hickory school district and built in 2011, this home offers a great combination of space, style, and functionality.

1221 Rosebud Lane, South Chesapeake

$624,900

4 Beds ⋅ 2.1 Baths ⋅ 10653639 MLS

Welcome home to this spacious, beautiful 4-bedroom, 2.5-bath home in sought-after Peyton Estates, offering nearly 2,800 square feet of comfortable living space on a generously sized lot. Inside, you’ll find plenty of room to spread out, including inviting living spaces and a cozy fireplace. A whole-house water filtration system adds an extra level of everyday comfort and convenience. The attached garage provides practical storage and parking, while the rear deck is a great place to relax, entertain, or enjoy the backyard. Tucked into an established Chesapeake neighborhood with convenient access to Greenbrier shopping, dining, interstates, and more, this home offers the space, location, and flexibility today’s buyers are looking for. Come see all it has to offer!

316 Janes Way, South Chesapeake

$435,000

4 Beds ⋅ 2.1 Baths ⋅ 10652939 MLS

4 bedrooms 2.5 baths on cul-de-sac. Large fenced yard on lake with shed. All kitchen appliances. New electric panel and HVAC in 2023. New fence across the back of yard in 2024. Reverse osmosis and re-mineralizer installed on kitchen sink. New kitchen faucet and microwave in September 2026. Refrigerator "As-Is". Fireplace and dryer vent cleaned and inspected August 2026. Carpets to be professionally cleaned prior to closing.

1901 Kelly Run, South Chesapeake

$535,000

4 Beds ⋅ 2.1 Baths ⋅ 10653596 MLS

Welcome to an exceptional Pines of Warrick residence in sought-after Great Bridge, where timeless elegance meets thoughtful modern updates. This beautifully maintained 4-bedroom, 2.5-bath home offers gracious living spaces, impressive room sizes, and a long list of improvements that make this home truly special. The renovated kitchen is a standout, featuring gorgeous custom high-end cabinetry, granite countertops, a stunning beveled ceramic subway tile backsplash, and a charming breakfast nook. Rich hardwood floors, crown moulding, and classic architectural details add warmth and sophistication throughout. The formal dining room and private library/office with French doors offer elegant spaces for entertaining or working from home. The inviting family room centers around a wood-burning fireplace (gas line remains if desired) and flows naturally into the sunroom, creating a wonderful connection to the spacious deck and large fenced backyard. The first-floor primary suite offers double closets and a beautifully remodeled en-suite bath, while the generously sized secondary bedrooms provide plenty of flexibility. Upstairs, the finished room over the garage with custom built-ins offers endless possibilities as a media room, 4th bedroom, playroom, office, or hobby space. Extensive recent improvements include TWO new zoned HVAC heat pump systems, inside and out (March 2025), a condensate drain pump with alarm (April 2025), and significant crawlspace improvements including a new vapor barrier, dehumidifier, lighting, extended access door, and sump system to divert gutter, HVAC condensate, and dehumidifier drains (2020). Additional updates include a new garage door and opener (2021) and newer dishwasher. Meticulously cared for and thoughtfully updated, this is a home that offers both character and peace of mind in one of Chesapeake's most desirable communities. Come see it for yourself—you won't want to miss this one!

424 Pines Of Warrick Drive, South Chesapeake

$380,000

3 Beds ⋅ 2.1 Baths ⋅ 10653557 MLS

Beautiful Single Family Condo in the heart of Great Bridge/Grassfield! New Roof, A/C Unit & Deck (Over 30k in upgrades). 1st floor Primary Bedroom, soaring ceiling in great room, Eat-In-Kitchen, dining room, 2 bedrooms and full Bath on the 2nd floor. Better Hurry!

1216 Club Point Drive, South Chesapeake

$549,900

4 Beds ⋅ 3 Baths ⋅ 10653411 MLS

Beautifully maintained 4-bedroom, 3-full-bath home offering an open, spacious floor plan with 9-foot ceilings and hardwood flooring. The inviting kitchen features stainless steel appliances, bar seating, and flows seamlessly into the living area. The main level includes the primary suite plus two additional bedrooms. Upstairs, a private fourth bedroom with its own full bath provides wonderful flexibility for guests, a home office, or additional living space. Relax on the covered front porch or back deck. NEW HVAC in 2025! Neighborhood amenities include a clubhouse, pool, two playgrounds, dog park, and four fishing ponds. A brand-new elementary school is being built within the neighborhood and is scheduled to open next school year. VA assumable loan at 5.625%, subject to lender/VA approval and buyer qualification.

3240 Conservancy Drive, South Chesapeake

$575,000

5 Beds ⋅ 3 Baths ⋅ 10653391 MLS

Gorgeous, like-new home built in 2016 offering over 2,400 sq ft of living space. A first-floor bedroom and full bath make this layout great for guests, a home office, or an in-law suite.The gourmet kitchen is made for entertaining, featuring granite countertops, stainless steel appliances, and a gas range. Step outside to a fenced backyard backing to peaceful wooded views; great for morning coffee or quiet evenings.With modern finishes throughout and minimal need for updates, this home is truly move-in ready and packed with value!

1201 Richwood Avenue, South Chesapeake

$450,000

4 Beds ⋅ 2.1 Baths ⋅ 10653149 MLS

Welcome home to Greenbrier! This beautifully maintained, move in ready home is tucked away on a desirable cul-de-sac in the heart of Chesapeake. Featuring numerous recent updates, you can move in with confidence and enjoy! The kitchen was updated in 2023 with new cabinets, countertops, and appliances. All bathrooms were refreshed in 2024 with new vanities, sinks, tubs, toilets, flooring, and paint. Major updates include a roof (2017), fence (2021), HVAC furnace (2025), condenser(2026), and water heater (2026). The first floor offers a spacious foyer, open living and dining areas, plus flexible bonus space great for a home office or playroom. Upstairs features a large primary suite with private bath and walk-in closet, three additional bedrooms, and a spacious shared bath. Conveniently located near Greenbrier shopping, dining, interstates, and local attractions. Don't miss your opportunity to make this home yours!

1914 Keeter Run, South Chesapeake

$639,900

4 Beds ⋅ 2.1 Baths ⋅ 10653324 MLS

Located in the highly coveted Grassfield High School District, this beautifully maintained 2021-built home offers modern style, thoughtful design, and plenty of natural light. The bright, open floor plan features hardwood floors throughout the entire first floor and a desirable downstairs in-law suite and finished back room. The chef’s kitchen is the heart of the home, showcasing quartz countertops, a gas range, and a deep island providing generous seating and additional prep space. The primary bath continues the elevated finishes with quartz countertops, dual shower heads, and beautiful upgraded tile. A first-floor laundry room adds everyday convenience, while the spacious all-seasons screened-in porch creates the space to relax or entertain year-round. With its inviting layout, quality finishes, and abundance of natural light, this home offers the perfect blend of comfort and style. HUGE Inlaw suite as well for people looking.

2065 Shipyard Road, South Chesapeake

$539,900

4 Beds ⋅ 2.1 Baths ⋅ 10653218 MLS

Welcome to this spacious, thoughtfully designed home offering generous living areas and a floor plan that blends comfort with functionality. Several updates have already been completed, to include: HVAC, roof, house trim, soffit, & gutter system, electric stove, carpet/LVT flooring, some interior paint, new pool salt system & Dolphin pool vacuum. The expansive backyard is a true retreat, featuring beautiful mature trees, a sparkling in-ground saltwater pool, and a spacious deck perfect for entertaining or unwinding. Situated on a large lot with a two-car garage, this property offers the ideal combination of space, privacy, and potential. Conveniently located in the sought after Hickory school district and near shopping, dining, and major commuter routes, this is a home you'll want to experience in person.

1505 Hilltop Drive, South Chesapeake

$325,000

3 Beds ⋅ 2 Baths ⋅ 10652903 MLS

Welcome Home to Deep Creek! Don’t miss this charming and well-maintained 3-bedroom, 2-bath ranch-style home nestled in an established neighborhood. Offering approximately 1,388 square feet of comfortable living space, this home has plenty of room to live, work, and entertain. The home features a spacious living room and a versatile flex room that can easily be used as a home office, playroom, second living area, hobby space, or whatever best fits your lifestyle. The spacious bedrooms offer plenty of room for comfort, while the kitchen includes a convenient eat-in area perfect for everyday meals. Step outside to the huge, fully fenced backyard, offering plenty of space for entertaining, outdoor gatherings, pets, gardening (check out the fruit trees), or simply relaxing and enjoying the outdoors. With its flexible floor plan, spacious backyard, and convenient Deep Creek location, this home is ready for its next owner. Schedule your private showing today!

3117 Kenelm Drive, South Chesapeake

$719,900

5 Beds ⋅ 4 Baths ⋅ 10653264 MLS

Nestled on a cul-de-sac in Saddle Ridge Estates with NO HOA, 804 Wakedale Arch offers 3,720 square feet of spacious living with five bedrooms and four full baths. New hardwood floors, new carpet, and fresh paint throughout make this home move-in ready. An expansive sunroom just off the eat-in kitchen provides additional space for entertaining or relaxing. The generously sized primary suite features a sitting area, walk-in closet, and private bath with dual vanities, a separate shower, and soaking tub. A first-floor bedroom and full bath offer flexibility for guests or multigenerational living. Enjoy practical extras, including ample built-in garage shelving and a backyard shed with electricity. Space, comfort, and convenience come together in this beautifully refreshed home!

804 Wakedale Arch, 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.