South Chesapeake Homes with Cul-De-Sac Exterior features

Welcome to South Chesapeake, Virginia—a hidden gem that seamlessly blends suburban tranquility with vibrant community life. Nestled within the picturesque Chesapeake County, this charming area offers a perfect balance of nature and modern convenience, making it an ideal place to call home. With its lush parks, scenic waterways, and friendly neighborhoods, South Chesapeake invites residents to enjoy a lifestyle rich in outdoor activities and community spirit.

One of the standout features of homes in South Chesapeake is their location on serene cul-de-sacs. These quiet, tree-lined streets provide a safe and peaceful environment for families, allowing children to play freely while neighbors foster lasting friendships. Homes with cul-de-sac exteriors are not just about aesthetics; they embody a sense of community, where gatherings and friendly chats become part of daily life.

The architectural styles in this area vary, showcasing everything from charming single-family homes to modern townhouses, all designed with comfort and functionality in mind. Many of these properties boast spacious yards, perfect for gardening, entertaining, or simply enjoying the beautiful Virginia weather.

In addition, South Chesapeake is conveniently located near shopping centers, dining options, and top-rated schools, ensuring that everything you need is just a stone's throw away. Whether you're a first-time homebuyer or looking to settle down, South Chesapeake offers a welcoming atmosphere and a strong sense of community that makes it a truly wonderful place to live. Discover your dream home nestled in a peaceful cul-de-sac and experience the charm of South Chesapeake for yourself!

Newest South Chesapeake Homes with Cul-De-Sac Exterior features

$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

$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

$725,000

5 Beds ⋅ 3.1 Baths ⋅ 10652854 MLS

Sought-after Cheshire Forest! This custom Crumley-built home offers 5 bedrooms, 3.5 baths and approx. 3,100 sq. ft., with over $100K in improvements in less than two years. All 3.5 baths were beautifully remodeled by Jerry Harris with premium finishes and a level of luxury you'd expect in million-dollar homes. The primary bath is a showstopper with a soaking tub, oversized shower and dual shower heads. Additional upgrades include EMTEK door hardware, Leviton Decora Plus switches and outlets, fresh interior paint and a refreshed kitchen open to the den. The 5th bedroom offers flexible office space. Outside, enjoy an inground pool with attached hot tub, screened porch, privacy fence and greenspace. Two staircases add to the custom layout. Tucked away on a cul-de-sac with Cheshire Forest amenities including clubhouse, community pool, tennis courts and playgrounds, all in the Great Bridge school district.

813 Satinwood Court, South Chesapeake

$575,000

5 Beds ⋅ 3.1 Baths ⋅ 10653159 MLS

A rare financing opportunity and an exceptional floor plan set this completely renovated 5-bedroom, 3.5-bath home apart. Qualified buyers may be eligible to assume the seller’s existing VA loan at an incredible 2.625% interest rate, subject to servicer approval and existing loan terms. The versatile layout provides flexibility for extended family, guests, private workspaces and everyday living. Imagine cooling your home and enjoying the pool all summer with an electric bill that is virtually nonexistent. The seller reports exceptional energy savings from the solar-panel system, which will convey free and clear at closing. Other major improvements include new vinyl siding, garage door, HVAC, tankless water heater, fresh paint and so much more. The backyard paradise features a heated saltwater above-ground pool, new privacy fence and dedicated pool room that can also serve as a workout or recreation space. A well and sprinkler system help maintain the grounds.

412 Harper Court, South Chesapeake

$685,000

5 Beds ⋅ 2.1 Baths ⋅ 10652920 MLS

Welcome to a home where thoughtful design meets effortless comfort. Beautifully updated with brand-new LVP flooring, this inviting residence is enhanced by an impressive collection of custom upgrades. The primary suite features a California Closets custom system, while the office offers tailored shelving and storage. In the kitchen’s eat-in area, a dedicated dog station and additional pantry provide both style and everyday functionality. Step outside and discover a private backyard backing to peaceful woods, complete with a fire pit—for relaxing or entertaining under the stars. The screened-in porch offers another inviting space to unwind and enjoy your favorite show. With the neighborhood playground just across the street, this home blends privacy, convenience, and thoughtful details in all the right ways. A home this special deserves to be seen!

952 Checkerspot Way, South Chesapeake

$269,900

3 Beds ⋅ 1.1 Baths ⋅ 10653121 MLS

Welcome home to this 3-bedroom, 1.5-bath home featuring a spacious living room with a fireplace, stainless steel appliances, and a kitchen with abundant cabinet storage. Three bedrooms and a full bath are located upstairs, with a convenient half bath on the main level. Enjoy the fully fenced backyard w/ storage, and the added value of a new HVAC system to be installed prior to closing. Conveniently located with easy access to shopping, dining, and everyday amenities.

1007 River Birch Court, South Chesapeake

$280,000

3 Beds ⋅ 1.1 Baths ⋅ 10653026 MLS

Welcome home to this well-maintained 3-bedroom, 1.5-bath townhome! All major systems have been replaced within the last 8 years, including the roof, offering valuable updates already taken care of. The home features a functional layout with comfortable living spaces and plenty of potential to make it your own. Best of all, there are NO HOA, giving you the benefits of townhome living without the added monthly expense. Whether you're a first-time homebuyer or simply looking for a place to call home, this property is ready for its next owner. Schedule your showing today!

1208 Basswood Court, South Chesapeake

$410,000

3 Beds ⋅ 2 Baths ⋅ 10653003 MLS

Welcome to this well-maintained 3-bedroom, 2-bath ranch home in the gorgeous Riverwalk community! Proudly offered by its original owner, this charming one-story home offers 1,600 square feet of comfortable living with the convenience of a first-floor primary bedroom. The inviting layout provides plenty of space for everyday living, entertaining, or simply relaxing at home. Step outside to enjoy the back deck and create your own peaceful outdoor retreat. Riverwalk residents enjoy fantastic amenities including a clubhouse, swimming pool, playgrounds, tennis courts, scenic trails, and a boat ramp and dock with access to the Elizabeth River. Conveniently located to access bases, beaches, dining, entertainment, restaurants, shopping, and more. Well cared for and ready for its next chapter—come see all this wonderful home and community have to offer. Call now for your personal tour.

435 Supplejack Court, South Chesapeake

$715,000

4 Beds ⋅ 3 Baths ⋅ 10652738 MLS

Wonderful home that owners have maintained in very good condition, located in cul-de-sac!4 Bedrooms, 3 Full baths, a downstairs bedroom is adjacent to a full bath. Beautiful sunroom with custom inlay tile, paver patio, kitchen with island, spacious main bedroom - full bath with dual sinks, soaking tub and walk-in shower. Large family room with natural gas fireplace, formal dining & living rooms, true 2 car garage, plenty of driveway space.Crawl space encapsulated w/dehumidifier.

812 Brookside Arch, South Chesapeake

$749,000

6 Beds ⋅ 3 Baths ⋅ 10652745 MLS

Welcome to this beautiful brick home in the heart of Great Bridge! Situated on a quiet cul-de-sac, this home has it all! The foyer and entrance way are stunning and extend two stories and include a beautiful stair case. A gorgeous new primary shower, trayed primary bedroom ceiling, hardwood flooring and a private deck that offers a peaceful, wooded view. The first floor bedroom/office has direct access to a full bathroom with newer vanity and is just right for multi-generational living. Both HVAC systems are two years young. The heavy lifting has been done here, this one won't last long! See it today before it is SOLD!!!

909 Brice Court, South Chesapeake

$485,000

4 Beds ⋅ 2.1 Baths ⋅ 10652092 MLS

Gorgeous renovated 4-bedroom, 2.5-bath home in sought after Riverwalk perfectly situated on a cul-de-sac. Open floor plan filled with natural light and stylish upgrades throughout. Stunning kitchen with custom cabinets, butcher block countertops, stainless-steel appliances and amazing center island. The formal dining room and cozy living room with fireplace offer ideal spaces for entertaining or relaxing. The primary ensuite has vaulted ceiling, double sink vanity, stunning shower and walk in closet. Enjoy relaxing on the oversized back deck for a peaceful backyard retreat. Additional highlights include a generous walk-in attic, oversized 2-car garage, and excellent storage throughout. Residents enjoy access to amenities including a clubhouse, swimming pool, playground, tennis courts, scenic trails, and a boat ramp and dock on the Elizabeth River. Close to beaches, military bases, amazing restaurants, shopping and more. Fantastic home and vibrant community!

418 Supplejack Court, South Chesapeake

$593,000

5 Beds ⋅ 2.1 Baths ⋅ 10652067 MLS

Special Buyer Bonus: Use our preferred lender and get your Home Inspection and Appraisal PAID FOR! Welcome home! Tucked away on a quiet cul-de-sac in desirable Miller's Run, this move-in-ready property welcomes you with a brand-new, rot-proof PVC front porch and brand new flooring throughout. Inside, enjoy an inviting kitchen equipped with updated appliances—including a new cooktop and dishwasher—plus a generous primary suite along designed for everyday comfort. Step out back to your private summer oasis! The spacious yard features an in-ground pool converted to saltwater in 2024 with updated equipment. The rear deck was extensively rebuilt with pressure-treated lumber. The seller will paint or stain it in your choice of color at closing! Schedule your private tour today and start packing!

3404 Louise James Court, South Chesapeake

Start Your Search

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.