Chesapeake VA Homes with Cul-De-Sac Exterior features

Welcome to Chesapeake, Virginia—a vibrant city that beautifully marries the charm of suburban living with the conveniences of urban life. Nestled in the heart of Hampton Roads, Chesapeake boasts a rich tapestry of history, culture, and natural beauty. With its picturesque landscapes, extensive parks, and serene waterways, this city is perfect for those seeking a tranquil yet connected lifestyle.

One of the standout features of homes in Chesapeake is the abundance of properties located on cul-de-sacs. These peaceful, family-friendly streets provide a safe haven for children to play and neighbors to connect. Homes with cul-de-sac exterior features often come with spacious yards, allowing for outdoor gatherings, gardening, or simply enjoying the fresh Virginia air. The layout of these neighborhoods fosters a sense of community, where residents can build lasting relationships in a serene setting.

Chesapeake is also known for its excellent schools, diverse dining options, and a plethora of recreational activities. Whether you’re exploring the Great Dismal Swamp, enjoying a day at one of the local parks, or indulging in the local culinary scene, there’s always something to do.

Investing in a cul-de-sac home in Chesapeake not only provides a beautiful living space but also a lifestyle rich in community and convenience. Experience the perfect blend of comfort and charm in this delightful city, where your dream home awaits!

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

$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

$509,900

4 Beds ⋅ 2.1 Baths ⋅ 10653139 MLS

Welcome to 508 Schaefer Avenue, a beautifully maintained 2018-built home in Chesapeake’s Deep Creek area! With 4 bedrooms, 2.5 baths, and 2,398 square feet, this home offers the space today’s buyers are looking for. The main level features an open flow between the kitchen, dining, and living areas, along with a separate front flex room ideal for a home office, playroom, or sitting room. The bright kitchen includes white cabinetry, granite countertops, a large island with seating, and stainless steel appliances. Upstairs, the spacious primary suite includes a separate sitting area and an ensuite bath with dual vanities, a soaking tub, and a separate glass shower. Three additional bedrooms and an upstairs laundry room add everyday convenience. Outside, enjoy a level backyard, concrete patio, wooded backdrop, and attached two-car garage. Potential 5.75% assumable loan opportunity for qualified buyers, subject to lender/servicer approval, underwriting, applicable terms, and buyer qualification. Schedule your private showing today!! THIS ONE IS A STEAL!!!

508 Schaefer Avenue, West 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

$399,000

3 Beds ⋅ 2 Baths ⋅ 10652696 MLS

A Beloved Western Branch Gem! Welcome to one of Western Branch’s most cherished neighborhoods, where many homeowners have proudly called this community home for 55+ years! This spacious brick rancher offers an inviting open floor plan, multiple flexible living spaces, and a peaceful cul-de-sac location. Step outside to enjoy the huge, private backyard, surrounded by mature trees providing wonderful shade and privacy, plus a brand-new deck perfect for relaxing or entertaining. Ideally located just minutes from Hampton Roads military bases, tunnels, bridges, shopping, dining, entertainment, doctors, and hospitals, this home puts convenience at your fingertips. Recent updates include new carpet (2023), new roof (2023), remodeled hall bath (2018), and HVAC (2016). Don’t miss your opportunity to own this wonderful home in a truly special neighborhood!

4353 Shorewood Drive, West 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

$275,000

3 Beds ⋅ 2 Baths ⋅ 10652244 MLS

REAL ESTATE AUCTION – PRICE SHOWN IS THE ADVERTISED STARTING BID, NOT THE SELLER’S RESERVE OR GUARANTEED SALE PRICE. This single-story brick ranch offers approximately 1,564 square feet with 3 bedrooms, 2 full bathrooms, an attached garage and a 0.332-acre lot. Live on-site auction Saturday, October 24, 2026, at 11:00 a.m. Reserve auction subject to seller confirmation. A 10% buyer’s premium will be added to the accepted high bid to determine the contract purchase price. Successful bidder must provide the required $10,000 deposit and close within 30 to 45 days. Property is offered as-is, where-is, with all faults and without financing, appraisal, inspection or other contingencies. Pre-auction traditional real estate offers may be considered until 48 hours before the live auction. Sealed absentee bidding is available under the published auction terms. Public previews are scheduled for Saturday, September 19, and Saturday, October 10, at 11:00 a.m. Buyers should complete all inspections, financing arrangements and due diligence before bidding. Auction documents are available through the listing agent.

2916 Mintwood Drive, West 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.