Chesapeake VA Homes with Cul-De-Sac Exterior features

Welcome to Chesapeake, Virginia—a vibrant community that beautifully blends suburban charm with urban convenience. Nestled in the heart of South Hampton Roads, Chesapeake is celebrated for its lush landscapes, rich history, and family-friendly atmosphere. With over 22 miles of waterfront, residents enjoy access to stunning parks, scenic trails, and a variety of recreational activities. The city’s commitment to maintaining green spaces and preserving natural beauty makes it an ideal place for families, outdoor enthusiasts, and anyone seeking a peaceful yet engaging lifestyle.

One of the most sought-after features in Chesapeake real estate is homes situated in charming cul-de-sacs. These delightful streets provide a sense of community and safety, making them perfect for families with children or anyone who values a quiet neighborhood. Cul-de-sacs often foster a close-knit environment where neighbors know one another, creating a welcoming atmosphere for all.

Homes with cul-de-sac exterior features typically boast spacious yards, ample parking, and reduced traffic, allowing for a serene living experience. These properties often have beautifully landscaped gardens and outdoor spaces perfect for entertaining or enjoying a quiet evening under the stars. Whether you’re looking for a modern abode or a classic family home, Chesapeake’s cul-de-sac offerings are sure to impress.

With top-rated schools, diverse dining options, and a variety of shopping venues, Chesapeake is not just a place to live; it’s a place to thrive. Explore the charm of Chesapeake, VA, and discover your dream home in a community that truly has it all!

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

$629,900

4 Beds ⋅ 2 Baths ⋅ 10655393 MLS

Welcome home to this charming 4-bedroom, 2-bath brick ranch nestled on 4.22 wooded acres at the end of a quiet cul-de-sac. Inside, you'll find a warm and inviting layout featuring a family room with a wood-burning fireplace, formal living and dining rooms, granite countertops, and beautifully updated primary and hall bathrooms. Step outside to relax on the new composite deck (2024), gather around the fire pit, or enjoy the peaceful wooded surroundings. The property also includes a detached 2-car garage with a finished studio apartment and full bath, plus a whole-house generator and water softener for added convenience. Offering space, privacy, and versatile living, this property is ready to welcome you home!

1345 Oak Ridge Drive, South Chesapeake

$599,900

4 Beds ⋅ 2.1 Baths ⋅ 10655291 MLS

Beautifully maintained, thoughtfully updated, and a backyard you'll want to spend all of your time in! Step inside to a welcoming foyer filled with natural light and discover this inviting 4 bedroom, 2.5 bathroom home in a sought-after neighborhood within the Hickory School District. Updates include Brazilian hardwood, upgraded pet protect carpet padding, PEX plumbing, electrical, solar power, and an electric fireplace with a gas hookup for conversion. With solar, the electric bill averages approximately $70/month. Outside, enjoy a private backyard oasis with manicured gardens, stonework, raised vegetable beds, blueberry bushes, apple trees and even an underground invisible fence! A fully insulated detached workshop with electricity and A/C offers flexible spaces for hobbies, projects, a studio, or workspace. Have instant hot water with top of the line Rinnai tankless water heater! HUGE corner lot! Meticulously maintained inside and out, this charming home is ready to be called home!

841 Woodstream Way, South Chesapeake

$609,000

5 Beds ⋅ 3 Baths ⋅ 10655211 MLS

This is the one to see $40K kit. w/waterfall quartz counters, soft close cab. all 2023, ss appliances and new LVT flooring dwn, new carpet up, Quartz FP front & crown dwn, New sliding glass door to SR, $30K in windows 2023, multi use insulated shed with mini split, new HW heater, new light fixtures, new add driveway 2023, garage door, attic stairs, toilet in hall, outlet & light switches to safety, roof 2018, new paint through out, air vents, rear gutters, a must see in cul-de-sac and more...

441 Chandler Drive, South Chesapeake

$705,000

4 Beds ⋅ 3 Baths ⋅ 10655182 MLS

Unique custom built home on cul-de-sac with rare 3 car attached garage and extended driveway. This house was made for entertaining - 23' x 14' screened porch off family room for extended living space, along with a 22' x 20' pavilion - both with trek decking, finished wood ceilings, recessed lights and fans. Beautiful extensive landscaping with a stamped concrete walkway winding around house. Impressive 2 story entry has gorgeous chandelier. Dual staircases. Large kitchen includes granite counters, stainless steel appliances with gas stove, tons of cabinets and counterspace as well as deep pantry and eat-in nook. Formal living room and dining room with door leading to large front porch. First floor office in addition to 4 bedrooms upstairs. Full bathroom downstairs. Hardwood floors run through entire 1st floor. Primary bedroom includes corner gas fireplace, 13'x12.5' walk-in closet, and large bathroom with dual sinks and jetted tub . Laundry room has entire wall of cabinets with counter space and fold down ironing board. Lots of built in storage throughout, including a walk in climate controlled attic closet. The rare 3 car garage (owner actually has 4 cars in there!) is decked out for a car aficionado with LED lighting covering the ceiling and rubberized flooring. Additional outside shed. 16 hardwired cameras around exterior convey. Generator hook up in garage. Top of the line outside Charbroil kitchen conveys with acceptable full price offer. Neighborhood dock with boat ramp nearby. Very active River Walk Community Association centers around the beautiful clubhouse (which can be rented) and has a tennis/pickleball court w/pickleball league, garden club, swimming pool w/swim team, concerts in fall, food trucks and more, as well as parks and playgrounds. Tree lined walking paths wind through neighborhood along lakes with gazebos and fountains. Easy to hop on nearby Rt. 168 Chesapeake Expressway to easily get to any area of Hampton Roads.

708 Pebble Quay, South Chesapeake

$797,640

5 Beds ⋅ 3.1 Baths ⋅ 10655214 MLS

The Tillman offers 3,226 sq. ft. of stylish and flexible living - great for multigenerational living! This spacious home includes 5 bedrooms, 3.5 baths, and a 2-car garage. The first-floor primary suite provides the perfect retreat with a massive walk-in closet, dual vanities, and a private water closet. Upstairs, you’ll find a second primary-style bedroom with direct access to a full bath, offering comfort and privacy. Three additional bedrooms (each with walk-in closets), a large loft, and a convenient laundry room complete the second floor. The open-concept main level features a welcoming dining room, expansive kitchen with an oversized island and two pantries, including a Costco pantry, and a bright family room. Photos and renderings are from builder's library, actual finishes and features may vary.

911 Intracoastal Way, South Chesapeake

$515,000

4 Beds ⋅ 2 Baths ⋅ 10654763 MLS

Welcome to 974 N Haven Circle, tucked away at the end of a quiet cul-de-sac on a spacious, fully fenced nearly half-acre lot in desirable Chesapeake! This well-maintained 4-bedroom, 2-full-bath home offers the perfect blend of comfort, functionality, privacy, and outdoor living. Enjoy peace of mind with whole-house siding and trim replaced in 2022, a tankless water heater, Ring cameras that convey, and a full-house crawlspace dehumidifier with an active Coastal Pest Control contract. The 30x28 detached shop is a dream for car enthusiasts, hobbyists, contractors, or anyone needing serious workspace and storage. Extra plywood flooring has been added in the FROG attic for even more storage. The expansive fenced backyard provides room to play, entertain, garden, or simply enjoy the outdoors. Located in a highly sought-after school district with convenient access to shopping, dining, parks, and everyday amenities. A rare combination of space, privacy, and versatility!

974 N Haven Circle, South Chesapeake

$300,000

3 Beds ⋅ 2.1 Baths ⋅ 10654893 MLS

Largest floor plan in the neighborhood! Lovingly maintained and thoughtfully updated, this spacious brick townhome is tucked away on a quiet cul-de-sac in the heart of Chesapeake. Enjoy a private, fully fenced backyard with no homes directly behind you and no HOA. Inside, you’ll find fresh paint, new carpet and flooring, updated bathrooms, new fixtures and hardware, and gleaming hardwood floors. The brand-new kitchen features granite countertops, stainless-steel appliances, a gas range, and full-size refrigerator. A wood-burning fireplace adds warmth and character, while abundant natural light fills the home. Plenty of indoor and outdoor storage provides added convenience. With a low-maintenance brick exterior, spacious floor plan, thoughtful updates, and a private backyard, this home is truly move-in ready. Pride of ownership is evident throughout—come see it today!

302 Fairfax Terrace, South Chesapeake

$445,000

4 Beds ⋅ 2 Baths ⋅ 10654764 MLS

Now this is a place you can call HOME! This charming brick ranch is situated on a spacious cul-de-sac lot with mature landscaping. Featuring 4 bedrooms a FROG that can serve as a bedroom, office, or bonus room man or woman cave. Enjoy a spacious living and dining area, cozy family room with built in bookcase and wood burning fireplace, and an eat in kitchen with newer cabinets and updated appliances. Additional features include replacement windows, architectural roof, updated primary bath, large attic for storage, and a one car attached garage. Relax on the wood deck with hot tub overlooking the spacious backyard. Conveniently located near shopping, restaurants, and interstate access. A Must See!

709 Caravelle Drive, South Chesapeake

$674,900

5 Beds ⋅ 4 Baths ⋅ 10654517 MLS

Welcome to this exceptional 5-bedroom, 4-bathroom, 3,250-square-foot Craftsman-style home, custom built by Summit Construction and ideally situated in the heart of Great Bridge on a quiet cul-de-sac. From the moment you step inside, you’ll appreciate the thoughtful design, quality craftsmanship, and extensive upgrades throughout. The spacious open-concept floor plan is perfect for both everyday living and entertaining, featuring beautiful true hardwood floors, a stunning stone fireplace with custom mantel, and an abundance of natural light. At the heart of the home is the impressive designer kitchen, complete with quartz countertops and backsplash, stainless steel appliances, and a convenient butler’s pantry featuring a wet bar and wine cabinet. The luxurious primary suite offers a gorgeous custom closet and a spa-inspired bathroom with a large tiled shower and relaxing soaking tub. A first-floor bedroom with its own ensuite bath provides an ideal space for guests, multigenerational living, or a private home office. Upstairs, you'll find additional generously sized bedrooms and thoughtfully designed living spaces. Step outside and enjoy your own private retreat with a large screened-in porch and an outdoor gas fire pit—perfect for relaxing, entertaining, and enjoying the outdoors throughout the year. There's also space designated for a future hot tub with reinforced concrete slab. Energy efficiency was also a priority, with upgraded spray-foam insulation helping enhance the home's overall efficiency and comfort. With its desirable Great Bridge location, spacious floor plan, exceptional finishes, and inviting indoor and outdoor living spaces, this beautifully crafted home offers the perfect combination of style, comfort, and functionality. Don’t miss the opportunity to make this remarkable home your own!

404 Foxgate Court, South Chesapeake

$305,000

2 Beds ⋅ 2 Baths ⋅ 10654480 MLS

Welcome to 816 Shenandoah River Road! Spacious 2 bedroom 2 bathroom condo tucked away in established Riverwalk! This move in ready home offers a cool modern feel with many updates throughout. Main living area welcomes you with fresh paint and LVP flooring. Kitchen has been updated to include custom cabinetry, quartz countertops and tile backsplash. One bedroom / bath occupy first floor and One bedroom / bathroom occupy second floor. Association is responsible for all exterior maintenance to include grounds and roof. Skylights were replaced in 2026. Enjoy all the riverwalk community has to offer, including Clubhouse, Pool, Tennis Courts, Boat Ramp, Playgrounds, Walking Trails and trash pickup.

816 Shenandoah River Road, South Chesapeake

$550,000

4 Beds ⋅ 2 Baths ⋅ 10654471 MLS

Beautiful Cape Cod ranch on a cul-de-sac lot featuring 4 bedrooms, 2 full baths, and a 2-car side-load garage. The spacious primary suite offers a walk-in closet and bright private bath with dual sinks and skylights, The great room features a gas fireplace, built-in bookshelves, and newer carpet, Convenient main-level bedroom, The kitchen boasts newer LVP flooring and stainless-steel appliances, with French doors leading to a screened-in back porch with ceiling fan. Freshly pressure washed and landscaped, the home offers easy-care yards with irrigation front and back. A backyard shed provides additional storage.

708 Wimbley Lane, South Chesapeake

$325,000

3 Beds ⋅ 1.1 Baths ⋅ 10654363 MLS

Come tour this ranch home with beautiful hardwood floors and a functional living space. This property has a partially open floor plan with a versatile layout. The open room space can be used to entertain, as an office, or as spare living space. The backyard is large and wooded, offering a storage shed and plenty of space for gardening and entertaining. The dishwasher, water heater, and refrigerator are all new (2025) and convey with the property.

1025 Shore Road, 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.