South Chesapeake Homes with Wooded Exterior features

Welcome to South Chesapeake, Virginia – a hidden gem that beautifully balances the tranquility of suburban living with the convenience of urban amenities. Nestled within the heart of Chesapeake County, this charming city is known for its lush landscapes, friendly neighborhoods, and a strong sense of community. With its rich history and vibrant culture, South Chesapeake offers a lifestyle that appeals to families, professionals, and retirees alike.

One of the standout features of homes in this picturesque area is their stunning wooded exterior. Imagine waking up to the soothing sounds of nature, surrounded by towering trees and vibrant greenery. These homes are designed to harmonize with their natural surroundings, providing a serene retreat from the hustle and bustle of daily life. The wooded exteriors not only enhance the aesthetic appeal but also offer privacy and a sense of seclusion, making them perfect for those who value tranquility.

In South Chesapeake, you’ll find a diverse range of properties, from charming single-family homes to modern townhouses, all featuring that coveted wooded charm. Enjoy spacious backyards perfect for family gatherings, outdoor barbecues, or simply unwinding with a good book under the shade of a tree. The community is also conveniently located near parks, schools, and shopping centers, ensuring that everything you need is just a short drive away.

Discover the beauty and comfort of South Chesapeake, where your dream home with a wooded exterior awaits! Whether you're looking to settle down or invest, this vibrant city is ready to welcome you home.

Newest South Chesapeake Homes with Wooded Exterior features

$520,000

4 Beds ⋅ 3.1 Baths ⋅ 10646463 MLS

If you’ve been searching for true peace and privacy without sacrificing convenience, this Grassfield gem is an absolute must-see. Set back from the street on a private driveway, the property opens up to nearly an acre of total solitude, completely enveloped by woods and lush mature greenery. Inside, fresh paint brings a bright, inviting energy to a floor plan built for real life. The layout is a rare find for multi-generational living, featuring two distinct main-level suites. The in-law wing includes its own living room, making it easy to use as a private apartment, a 5th bedroom, or a home office. The primary suite feels like a custom getaway with live-edge wood countertops, dual shower heads, and a custom walk-in closet system. Out back, the property turns into a full outdoor retreat featuring a storage shed, a chicken coop, separate hookups ready for a pool and hot tub, and a massive detached two-car workshop/garage complete with a carport and RV hookup. Welcome home!

891 Bells Mill Road, South Chesapeake

$700,000

5 Beds ⋅ 2.1 Baths ⋅ 10645293 MLS

Tucked away on a quiet cul-de-sac, this beautifully maintained custom home offers the perfect combination of quality construction, thoughtful upgrades, and everyday comfort. Built in 2004 and offering approximately 3,300 square feet, this all-brick home features 5 bedrooms, with 4 conveniently located on the first floor, providing exceptional flexibility for families, guests, or multi-generational living. From the moment you step inside, you'll appreciate the soaring cathedral ceilings, spacious living areas, and inviting gas fireplace that create a warm and welcoming atmosphere. The private primary suite offers a relaxing retreat with a jetted soaking tub and generous walk-in closets. One of this home's standout features is the incredible backyard privacy. Whether you're enjoying your morning coffee, hosting family and friends on the large deck, or simply unwinding after a long day, you'll love the peaceful setting and the feeling of having your own private oasis. This home also offers valuable upgrades that provide peace of mind for years to come. A whole-house generator ensures you're prepared and comfortable during unexpected power outages, while the encapsulated crawl space reflects the care and attention given to maintaining the home, helping protect the structure and enhance energy efficiency. An irrigation system keeps the lawn looking its best with minimal effort. Located in the highly sought-after Hickory school district, this home delivers the rare combination of timeless all-brick construction, flexible living space, exceptional privacy, and important long-term investments that today's buyers appreciate. If you've been searching for a home that is as practical as it is beautiful, this one is not to be missed. Some photos have been virtually staged.

1104 Arabian Arch, South Chesapeake

$510,000

4 Beds ⋅ 2.1 Baths ⋅ 10645829 MLS

WELCOME HOME! Tucked away on a quiet cul de sac and set on nearly an acre backing to peaceful woods, this beautifully maintained home offers the perfect blend of privacy, outdoor living, and everyday convenience. Whether you’re enjoying your morning coffee in the screened gazebo or entertaining family and friends, you’ll appreciate the peaceful setting this property provides. Inside, you’ll find stainless steel appliances, a spacious walk in pantry, a cozy gas fireplace, and thoughtful updates throughout, including a new roof installed in 2024. A transferable 2-10 Home Warranty provides added peace of mind for the next owner. Conveniently located near Interstate 64, Route 17, shopping, dining, and major military installations throughout Hampton Roads, this home offers the ideal balance of tranquility and accessibility. Don’t miss your opportunity to make this exceptional property your next home. Schedule your private showing today!

104 Bishops Court, South Chesapeake

$435,000

4 Beds ⋅ 2 Baths ⋅ 10645687 MLS

Welcome to this inviting 4-bedroom ranch in the sought after Mill Creek neighborhood. Freshly painted throughout with brand new carpet and a new roof, this home is truly move-in ready. Enter into a bright living room featuring vaulted ceilings and a cozy wood-burning fireplace, seamlessly opening to the fully remodeled kitchen. The kitchen shines with white shaker soft-close cabinets, quartz countertops, and stainless steel appliances. Two bedrooms sit just off the living room, accompanied by a beautifully updated hall bathroom and laundry room. The spacious primary bedroom offers a remodeled en-suite bathroom and a generous walk-in closet. The FROG provides flexibility as a 4th bedroom, guest space, or bonus room. Out back, enjoy a wood deck overlooking an above-ground pool and a peaceful backyard with views of the wooded area maintained by the Army Corps of Engineers along the Dismal Swamp Canal. The property extends about 10 ft beyond the back fence line. Don't miss this one.

500 Willow Bend Drive, South Chesapeake

$540,000

4 Beds ⋅ 2.1 Baths ⋅ 10645295 MLS

Located in the highly sought-after Grassfield High School district, this home offers an incredible opportunity to make a home of your own in one of Chesapeake's most desirable areas. Inside features a spacious, functional floor plan boasting nearly 2700 square feet of living space. The living areas are generous with comfortable bedrooms and plenty of room to personalize. Head outside to the home's standout feature -- an expansive backyard and large deck with endless possibilities for entertaining or creating a private outdoor retreat. Conveniently located near shopping, dining, parks, and major interstates!

963 Speight Lyons Loop, South Chesapeake

$899,900

4 Beds ⋅ 3 Baths ⋅ 10645653 MLS

Welcome to The Ashford by Wetherington Homes - MOVE IN BY AUGUST 2026! A 5-bedroom, 3-bath new construction home with over 2,700 sqft on approximately 2 acres in Hickory School District with NO HOA! Designed for todays buyer, this open-concept floorplan offers luxury finishes, designer details, outdoor entertaining, & flexible living spaces. The kitchen features quartz countertops, Frigidaire Professional appliances, custom wood hood, shaker cabinetry, & upgraded lighting. The 1st floor Primary Suite includes a tiled spa-style shower, dual vanities, & oversized walk-in closet. Two additional 1st floor bedrooms offer flexibility for guests or office space. Upstairs includes 2 bedrooms, full bath, & loft ideal for media room, playroom, or gym. Enjoy luxury new construction convenient to Edinburgh, Greenbrier, shopping, dining, & commuter routes while still offering privacy & acreage!

435 Gallbush Road, South Chesapeake

$644,900

4 Beds ⋅ 2.1 Baths ⋅ 10645606 MLS

Ask Agent about a potential VA assumable loan opportunity! Better Than New and Built in 2023, this beautifully and thoughtfully upgraded home offers the benefits of newer construction without the wait. Move-in ready with quick closing available. Bright, open-concept floor plan with abundant natural light. Gourmet kitchen features quartz countertops, oversized island, premium gas range, stainless steel appliances, walk-in pantry, and custom cabinetry. Spacious primary suite includes tray ceiling, dual walk-in closets, soaking tub, tiled shower, and dual vanities. Enjoy covered front and rear porches, extended patio, fully fenced backyard with wooded views, irrigation system, storage shed, custom window treatments, and exceptional attic storage. Convenient to military bases, shopping, dining, and major commuter routes. Trusted lender Steve Hawley (NMLS #1813927) from Southern Trust Mortgage (NMLS #2921) will provide a 1% lender-paid buydown on this listing. Ask Listing Agent for details.

640 Appalachian Court, South Chesapeake

$675,000

6 Beds ⋅ 2.1 Baths ⋅ 10645171 MLS

Rare opportunity to own over 6 private acres in the heart of Deep Creek! This exceptional property includes two parcels conveying with the sale, creating a combined 6+ acres of wooded privacy at the end of a quiet road. The spacious 6-bedroom home offers endless possibilities for multigenerational living, a home office, hobby space, or guest accommodations. Enjoy the peace and seclusion of country-style living while remaining just minutes from shopping, dining, schools, and major interstates. Come see this one first!

3249 Pioneer Lane, South Chesapeake

$225,000

2 Beds ⋅ 2 Baths ⋅ 10645413 MLS

Hard to find single level living! Newer LVP flooring in main living area, carpet in bedrooms less than 2 years old, galley kitchen and updated light fixtures. End unit tucked away but right across from the pool! All new windows and sliding glass door, move in ready.

1012 Rue Marseille, South Chesapeake

$529,900

4 Beds ⋅ 2.1 Baths ⋅ 10645403 MLS

You have seen the pictures and now I am sure you are curious about everything this house has to offer. Well, it is absolutely 100% turn-key, move-in ready with all of the bells and whistles. The home feels so good and invites tons of natural light. The kitchen has been thoughtfully remodeled adding tons of cabinet space, a center island, a pot filler and more functional layout. The cabinets, flooring (hand scraped bamboo), counters and appliances have all been recently upgraded as well. The bathrooms have all been remodeled and the primary bath is a small piece of heaven. Separate sinks, dual shower heads in the tile/glass shower and a separate soaking tub. Go outside and you might not go back in for quite a while. A covered porch and expansive deck greet you with the hot tub around the corner. Drop down to the 28,000 gallon in-ground pool complete with a built-in endless pool for serious swimmers. Backing up to the woods, this private, backyard paradise awaits you!

2107 Sunset Maple Lane, South Chesapeake

$585,000

4 Beds ⋅ 2.1 Baths ⋅ 10645167 MLS

Beautifully updated and impeccably maintained, this exceptional 4BR/2.5BA home offers thoughtfully designed living space in the highly sought-after Kemp Woods neighborhood of Chesapeake. Nestled on a quiet, tree-lined street, this move-in ready home perfectly blends timeless elegance, quality craftsmanship, & modern updates. Step inside to an inviting floor plan filled with natural light, with rich hardwood flooring, elegant plantation shutters, and spacious living areas. Gourmet kitchen is designed to impress, featuring tall cabinetry, built-in appliances, abundant counter space, & oversized breakfast area surrounded by windows that fill the space with natural light. Spacious primary suite is a true private retreat, complete with large walk-in closet & stunning, spa-inspired ensuite featuring beautifully tiled, oversized frameless glass walk-in shower, dual vanity, designer lighting, & luxurious finishes that create a resort-like experience at home. 3 additional generously sized bedrooms. Seamlessly extending the living space outdoors, both the family room and breakfast area open to an expansive multi-level deck overlooking the private backyard. Designed for entertaining and everyday enjoyment, this outdoor retreat offers oversized deck and a hot tub—perfect for summer gatherings, peaceful evenings, or relaxing under the stars. Major improvements provide exceptional peace of mind, including a roof, two-zone HVAC system, & numerous updates completed within the last 5 years, allowing the next owner to simply move in and enjoy. Conveniently located just minutes from Greenbrier’s premier shopping, dining, entertainment, parks, hospitals, and major commuter routes including I-64, this home offers the perfect balance of convenience and the quiet charm of one of Chesapeake’s most established and desirable neighborhoods. Some photos were virtually staged or digitally enhanced for marketing purposes to help buyers visualize the property’s potential. Schedule your showing today to make this house YOUR HOME!!

1045 Winchester Way, South Chesapeake

$500,000

4 Beds ⋅ 2 Baths ⋅ 10644991 MLS

Beautifully updated 4 bedroom, 2 bath ranch home in the sought-after Hickory School District! Move-in ready with big-ticket updates. Enjoy easy, single-level living with great natural light, neutral finishes, and smart storage. Outside, relax on the deck in the fenced backyard—perfect for entertaining, pets, and play. Convenient driveway parking and a low-maintenance exterior provide peace of mind. Centrally located near schools, parks, shopping, bases, and the oceanfront, with quick access to major routes.

808 Rutherford 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.