South Chesapeake Homes with Wooded View

Welcome to South Chesapeake, Virginia, a hidden gem that beautifully marries suburban tranquility with vibrant community life. Nestled in the heart of Chesapeake County, this charming area boasts a unique blend of lush landscapes, friendly neighborhoods, and a rich tapestry of local culture. Whether you’re a first-time homebuyer or looking to settle down, South Chesapeake offers an array of homes that cater to diverse tastes and lifestyles.

One of the most appealing aspects of South Chesapeake is its stunning homes with wooded views. Imagine waking up to the gentle rustle of leaves and the soothing sounds of nature right outside your window. These properties provide not just a home, but a sanctuary where you can unwind after a busy day. The wooded surroundings create a serene atmosphere, perfect for outdoor enthusiasts or anyone who appreciates the beauty of nature.

In addition to the picturesque scenery, South Chesapeake is known for its excellent schools, vibrant parks, and a variety of shopping and dining options. Families can enjoy weekend outings at local parks, while nature lovers can explore nearby trails and waterways. The community is committed to fostering a friendly atmosphere, ensuring that residents feel connected and engaged.

With its perfect blend of natural beauty, community spirit, and modern conveniences, South Chesapeake is an ideal place to call home. Discover the charm of homes with wooded views and embrace a lifestyle filled with peace, comfort, and a touch of nature in your everyday life. Come explore South Chesapeake, where your dream home awaits!

Newest South Chesapeake Homes with Wooded View

$759,999

5 Beds ⋅ 3.1 Baths ⋅ 10661845 MLS

Breathtaking water and wooded views make this home RARE! Culpepper Landing is situated along the Inter Coastal Waterway, and this lot offers views as larger boats pass by. Imagine stunning scenery while entertaining guests, fishing in the stocked pond, cooking in your gourmet kitchen, relaxing in the sunroom or private ensuite. Dream kitchen features a giant center island, double wall oven, gas stove, upgraded lighting, plenty of cabinets, and sizable walk-in pantry. Oversized primary ensuite features water views, sitting area, 2 walk-in closets, dual sink vanity, tiled shower, and separate soaking tub. 2nd floor flex space could be converted to create a 6th bedroom. 3rd floor has a bedroom, full bath, plus bonus media room. Custom upgrades include retractable garage screen, fence, mudroom, wainscoting, and decorative accents. Resort style amenities include a pool, clubhouse, fitness center, playgrounds, dog park, & fishing ponds. NEW elementary school being built in the neighborhood.

818 Olmstead Street, South Chesapeake

$315,000

4 Beds ⋅ 2 Baths ⋅ 10661579 MLS

So much potential in this cape cod located in Deep Creek! Situated on over a half-acre with an addition that includes- one bedroom/full bath, large living area, small fridge/freezer, microwave, washer/dryer and balcony with private access. Addition could be used as in-law suite, business or it previously was used as an income producing unit. In the main house there are 3 bedrooms and a full bath downstairs, living & dining room, and kitchen. A large back deck, above ground pool with newer liner and a detached garage w/electric and the potential to finish the upstairs level of garage. HVAC was just recently updated along with ductwork. Great opportunity for investors! Home being sold "AS-IS".

3240 Galberry Road, South Chesapeake

620 Estates Way Unit 120, South Chesapeake

$365,000

3 Beds ⋅ 2.1 Baths ⋅ 10661737 MLS

Enjoy easy, low-maintenance living on a quiet street with peaceful wooded views in Riverwalk. This 3-bedroom, 2.5-bath townhome-style condo offers 1,831 sq. ft. and a thoughtfully designed floor plan with no wasted space. The open main level connects inviting living and dining areas, a gas fireplace, and a kitchen with granite counters, stainless steel appliances and a gas range. Upstairs, a spacious primary suite features double sinks, a tiled shower and a walk-in closet. A versatile loft adds room for work or relaxation, while the second-floor laundry room keeps everyday chores convenient. Unwind on the shaded rear deck overlooking the trees, and enjoy the storage and convenience of an oversized attached garage. High-efficiency York HVAC installed Dec. 2025. Condo fee includes master insurance, exterior/grounds maintenance and trash pickup. Shopping, dining, parks and interstate access are nearby. Pre-list inspection available.

620 Estates Way Unit 120, South Chesapeake

$549,900

5 Beds ⋅ 3 Baths ⋅ 10661712 MLS

Welcome home to this immaculate meticulously maintained original owner home in sought after Clearfield Estates. Numerous improvements gas water tank 10/26, LG Refrigerator 5/26, dishwasher 3/26, windows 12/25, roof 30-year architectural 10/23, AC 2013. Triple French patio door looks out to expansive private .30 acre back yard. First floor guest bedroom with full bath, first floor features Brazilian engineered wood floors, open concept with cozy gas fireplace, 4 additional spacious second floor bedrooms including a massive 14.5 X 28 FROG with walk in attic & built ins great for entertaining! Spacious primary features a cathedral ceiling large walk in closet, duel vanities and jetted tub. Central Greenbrier location with easy commute to multiple bases, VB and Norfolk. Sq ft per tax record

408 Brandon Way, South Chesapeake

$1,250,000

4 Beds ⋅ 3.2 Baths ⋅ 10661534 MLS

A truly one-of-a-kind custom-built residence, where exceptional craftsmanship, distinctive architectural details and an extraordinary setting come together in the sought-after Hunters Ridge neighborhood. From the stunning stonework and graceful archways to the custom solid wood and glass doors, every detail reflects a level of character and design rarely found. The impressive primary suite offers a beautiful retreat overlooking the private woods. The tranquil primary bath provides the perfect setting to unwind and recharge.An exceptional feature of this home is the attached in-law suite, offering its own private entrance, garage, full kitchen, one bedroom, 1.5 bathrooms, dedicated washer/dryer and abundant storage. This thoughtfully designed space offers versatility without sacrificing privacy.Tucked away at the end of a cul-de-sac and backing to private wooded views, the property offers a peaceful sense of seclusion while remaining approximately 15 minutes from everyday conveniences

2500 Evans Lane, South Chesapeake

$354,900

2 Beds ⋅ 2.1 Baths ⋅ 10661637 MLS

Stunning townhome in the sought-after Riverwalk community! Nestled on a quiet-cul-de-sac, this meticulously maintained home features a bright open floor plan with abundant natural light. The eat-in kitchen offers Stainless Steel appliances, pantry, ample cabinetry, generous counter space, and a coffee bar. Gleaming hardwood floors flow throughout the main level and stairs. All window treatments & all appliances convey. Spacious dining room and Great Room with a cozy gas fireplace. Upstairs, both Bedrooms feature en-suite baths, including a large primary suite with walk in shower and Jetted tub. Upgraded carpet upstairs. Private fenced-in large backyard- covered patio and direct access to trails. 2024 Gas Furnace. Tankless water heater. LeafGuard® gutters. Attached Garage, ample storage including attic. Oversized driveway for up to 4 vehicles. ADT® security system throughout home. Amenities include front yard maintenance, trash pickup, Walking trails, & playgrounds. Central location.

810 Royal Grove Court, South Chesapeake

$600,000

6 Beds ⋅ 2.1 Baths ⋅ 10661261 MLS

Motivated seller! This home offers an assumable FHA loan at 2.75% for a qualified buyer, and the seller is willing to contribute toward closing costs with an acceptable offer. Located in Chesapeake’s sought-after Grassfield school district, this freshly painted, move-in ready home offers space, flexibility, and room to grow. The open floor plan centers around a spacious kitchen with generous cabinet and counter space, pantry storage, and an easy connection to the main living areas. With multiple finished areas across three levels, the layout works well for multigenerational living, long-term guests, remote work, hobbies, a media room, playroom, or additional bedrooms. The third floor was expanded in 2021 to include two finished rooms, giving buyers even more space. Outside, the large fully fenced backyard and spacious deck are ready for cookouts, pets, play, relaxing evenings, and weekend gatherings. An expanded extra-wide driveway and EV charger add everyday convenience.

568 Waters Road, South Chesapeake

925 Cranberry Drive Unit 70, South Chesapeake

$514,900

4 Beds ⋅ 2.1 Baths ⋅ 10661392 MLS

Welcome to this beautifully maintained condo in one of Chesapeake's most desirable 55+ communities where, comfort and convenience come together in a park-like setting. Surrounded by mature landscaping, a scenic pond, and inviting seating area with a fireplace, this neighborhood offers a relaxed lifestyle with thoughtfully designed community spaces. Inside, this spacious home offers four bedrooms and two and a half bathrooms with a layout designed for both everyday living and entertainment. The primary suite provides a comfortable retreat with generous space and privacy. An in-unit elevator adds exceptional convenience and accessibility between levels. Call today for your private tour. Brand new heating and cooling systems installed 11/2026. Closing cost assistance available with acceptable offer!

925 Cranberry Drive Unit 70, South Chesapeake

$525,000

3 Beds ⋅ 2 Baths ⋅ 10661321 MLS

Your dream of country life is here! All brick updated ranch on almost 3 spacious acres! Has a huge garden space, watch wildlife but be near all the city conveniences. Big updated kitchen with beautiful cabinets and newer appliances. Bathrooms have also been updated. Off the back enjoy you spacious deck over looking the fruit trees and wildlife. The basement is fully floored and professional sealed. Basement has electricity and it's where the washer and dryer are located. It also has an outside entrance. Utilize this space for storage, exercise room, playroom, etc. This is a rare find.

2832 Benefit Road, South Chesapeake

3708 Riverwood Crescent, South Chesapeake

$750,000

5 Beds ⋅ 2.1 Baths ⋅ 10661394 MLS

Set on approximately 3 acres in Chesapeake’s Riverwood neighborhood (23322), 3708 Riverwood Crescent offers nearly 3,000 sq ft with 5 bedrooms, 2.5 baths, and a private, wooded backyard with a pool, screened porch, and updated deck. The remodeled kitchen features quartz countertops, soft-close cabinetry, recessed lighting, and mostly stainless steel appliances. Inside you’ll also find hardwood and luxury vinyl plank floors, new upstairs carpet, and updated baths with an enlarged porcelain-tiled primary shower. Major updates include dual-zone HVAC (2019/2021), a 2024 water heater, a water softener, an encapsulated crawl space with pump and dehumidifier (transferrable warranty), and replaced exterior and garage doors. The vinyl windows and screens have a transferable warranty, and the roof was replaced in 2011 with a 50-year warranty. The septic tank was recently pumped, and the shed and lawn tractor convey. Seller is willing to offer allowance for painting foyer and dining room.

3708 Riverwood Crescent, South Chesapeake

$679,000

5 Beds ⋅ 2.1 Baths ⋅ 10661245 MLS

Come see all the thoughtful details that make this home truly special! Featuring brand-new LVP flooring and an impressive array of custom upgrades, this home blends style, comfort, and everyday convenience. The primary suite boasts a custom California Closets system, while the office features beautifully tailored shelving and storage. The kitchen’s eat-in area offers a clever built-in dog station and additional pantry space. Step outside to your own peaceful retreat, where a private backyard backs to the woods and features a fire pit for relaxing or entertaining. The screened-in porch provides yet another inviting space to unwind and catch your favorite show. With the neighborhood playground just across the street, this home offers the perfect blend of privacy, functionality, and lifestyle. Don't just take our word for it—come see everything this home has to offer. You won't want to miss it!

952 Checkerspot Way, South Chesapeake

$975,000

6 Beds ⋅ 3 Baths ⋅ 10661286 MLS

Modern Farmhouse Charm Meets Turnkey Living in Desirable Chesapeake! Discover the modern farmhouse you’ve been dreaming of, where peaceful country living meets thoughtful, top-to-bottom renovation. Set on 3 Serene acres with panoramic wooded views. It embraces the natural surroundings. This beautifully refreshed home is ideal for extended family/multi generational living. Natural light fills the home, showcasing new flooring, fresh interior paint, updated lighting, and beautifully renovated bathrooms. The completely redesigned custom kitchen is the heart of the home, featuring quartz countertops, ceramic backsplash, abundant prep space, an inviting eat-in area and a KitchenAid appliance suite, ideal for everyday living and entertaining. The expansive living area offers plenty of room to gather, while the renovated wood-burning fireplace creates a cozy focal point with a new firebox, flue, chimney cap, and Buck Stove-style insert. Step onto the Trex deck with PVC railing and enjoy peaceful wooded views from the living space, primary suite or deck. The primary suite is a true retreat, featuring a custom-tiled shower with built-in bench and generous niche, deep soaking tub, double vanity and ceramic tile flooring. The expansive custom closet with built ins provides all the space you have been longing for. Additional improvements include an encapsulated crawlspace with dehumidifier, new septic system designed for 10 occupants, finished room over the garage with generous storage, updated downstairs ductwork, new interior and exterior doors and hardware, new lighting throughout, and a freshly graded crushed-aggregate driveway. The painted brick exterior adds a fresh, modern look while preserving brick’s timeless durability and character. Best of all, the home features a highly energy-efficient geothermal HVAC system. From the crawlspace to the exterior, virtually nothing has been overlooked. Renovated by New Again Houses VB. It offers the feel of quality new construction without sacrificing character, space or setting. See it today!

3132 Benefit 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.

South Chesapeake Homes with Wooded View

Newest South Chesapeake Homes with Wooded View

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