South Chesapeake Homes with Wooded View

Welcome to South Chesapeake, Virginia—a hidden gem nestled within the vibrant Chesapeake County. This enchanting area is characterized by its picturesque landscapes, rich history, and a welcoming community that truly embodies the charm of Southern living. Known for its lush greenery and serene surroundings, South Chesapeake offers residents a perfect blend of suburban tranquility and urban convenience.

One of the most captivating features of homes in South Chesapeake is their stunning wooded views. Imagine waking up each morning to the gentle rustle of leaves and the soothing sounds of nature right outside your window. Many properties in this area are thoughtfully designed to maximize these breathtaking vistas, providing a peaceful retreat from the hustle and bustle of everyday life. Whether you’re sipping your morning coffee on a spacious deck or enjoying a sunset stroll through your backyard, the beauty of the woods will always be a part of your daily experience.

South Chesapeake is not just about beautiful homes; it’s also a community that values outdoor living. With numerous parks, trails, and recreational areas nearby, residents have ample opportunities to explore the great outdoors. Families can enjoy weekend picnics, hiking adventures, and even fishing in the nearby waterways, all while surrounded by the natural beauty that defines this charming city.

If you're searching for a home that offers both comfort and a connection to nature, South Chesapeake is the perfect place to call home. Experience the tranquility of wooded views and the warmth of a close-knit community in this delightful corner of Virginia. Welcome home to South Chesapeake!

Newest South Chesapeake Homes with Wooded View

$734,900

5 Beds ⋅ 3 Baths ⋅ 10646525 MLS

There is not enough space to explain how wonderful this home is! A rare sense of privacy meets thoughtful luxury in this upgraded 2022 Grassfield home. Near the end of a cul-de-sac and bordered by protected wetlands and unbuildable parcels on both sides, the lot offers a wooded backdrop that is hard to replicate. The flexible 5-bedroom, 3-bath layout includes two primary suites, one on the first floor, PLUS an office/flex room AND loft-style second living area. Crown molding, hardwood stairs, custom window treatments, a gas fireplace, quartz countertops, stainless appliances, gas cooking, under-cabinet lighting, upstairs laundry, walk-in attic, tankless water heater, smart garage opener, security system, and a custom 36-foot patio add comfort and refinement. Trusted lender Steve Hawley, NMLS #1813927, with Southern Trust Mortgage, NMLS #2921, will provide a 1% lender-paid buydown on this listing. Ask the listing agent for details. Subject to borrower qualification and lender approval.

1741 Watershed Court, South Chesapeake

$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

$849,900

5 Beds ⋅ 4.1 Baths ⋅ 10646141 MLS

Under Construction – Luxury New Construction with Timeless Coastal Farmhouse Style! This stunning 3-level home blends classic board-and-batten architecture, clean lines, black-framed windows, and thougthful accents to create exceptional appeal. Inside, an open-concept first floor is designed for modern living, featuring a spacious family room, dining area, and a designer kitchen with a large center island, custom cabinetry, and premium finishes. The second level offers four generously sized bedrooms, including an impressive owner's suite with a spa-inspired bath, plus two full bathrooms to comfortably accommodate family and guests. The third floor provides incredible flexibility with a spacious bonus room or fifth bedroom, a full bath, and convenient walk-in attic storage. With 5 bedrooms, 4.5 baths, thoughtful craftsmanship, and stylish finishes throughout, this exceptional new home offers the perfect blend of luxury, comfort, and functionality for today's lifestyle.

1833 Shillelagh Road, South Chesapeake

$550,000

3 Beds ⋅ 2.1 Baths ⋅ 10645963 MLS

Wonderful opportunity to get 4+ acres in high rated schools. HUGE outbuilding with 3 bays garage bays, powered, multi-level, for storage and recreational activities. Home sold as is. Part of an estate. Seller to do no repairs.

2323 Herring Ditch Road, South Chesapeake

$699,900

4 Beds ⋅ 3.1 Baths ⋅ 10645155 MLS

Welcome to this beautiful and spacious, well-maintained home that boasts 3261 sq.ft., four 2nd floor Bedrooms, 3.5 Baths + 1st floor Office, Dining Room, Sunroom, Family Room with cozy gas log fireplace, Living Room with handsome built-in bookcases, 12x10 shed, over 1/3rd acre corner lot, 1000 sq.ft. paver patio, 2nd floor Bedroom with ensuite bath & adjacent Loft is perfect for an In-Law Suite. 3 car garage provides ample parking and storage. Come see your dream home today!

2300 Burgess 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

$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

$280,000

2 Beds ⋅ 2 Baths ⋅ 10645506 MLS

This fantastic move-in-ready condo has undergone numerous recent upgrades (too many to list).LVP flooring and carpet, fresh paint throughout. 1st floor features include a BR with an attached bath and soaring vaulted ceilings. Tucked away in a secluded area, this property backs up to a private grassy area. Community amenities include a pool.

1641 Orchard Grove Drive, 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

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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.