South Chesapeake Homes with Wooded View

Welcome to South Chesapeake, Virginia—a hidden gem nestled within the vibrant Chesapeake County. This charming city boasts a harmonious blend of natural beauty and suburban convenience, making it an ideal place for families, professionals, and retirees alike. With its lush landscapes, tranquil neighborhoods, and friendly community, South Chesapeake offers a serene escape from the hustle and bustle of city life while still providing easy access to urban amenities.

One of the standout features of South Chesapeake is its stunning homes with wooded views. Imagine waking up each morning to the gentle rustle of leaves and the soothing sounds of nature right outside your window. These properties not only provide a picturesque backdrop but also offer a sense of privacy and tranquility that is hard to find in more densely populated areas. Many of these homes are thoughtfully designed to blend seamlessly with their natural surroundings, featuring expansive decks, large windows, and open floor plans that invite the outdoors in.

In addition to the beautiful homes, South Chesapeake is home to an array of parks and recreational opportunities. Residents can enjoy hiking, biking, and picnicking in the nearby parks, or take a leisurely stroll through the tree-lined streets of their neighborhoods. With excellent schools, shopping centers, and dining options just a stone's throw away, South Chesapeake is not just a place to live—it's a place to thrive.

If you're searching for a picturesque community with homes that offer both comfort and breathtaking wooded views, South Chesapeake is the perfect destination for you. Come experience the charm and beauty of this remarkable city!

Newest South Chesapeake Homes with Wooded View

$400,000

3 Beds ⋅ 2.1 Baths ⋅ 10649257 MLS

Welcome to 1715 Woodmill Drive, where the front yard takes care of itself. The association maintains the front landscaping, leaving the backyard yours to shape however you like, whether that's a garden, a grill setup, or a quiet spot to unwind.Three bedrooms plus a loft give you room to spread out, with the loft ready to work as an office, a reading nook, with built in cabintes. Recent updates include new flooring throughout, fresh paint, new fixtures, and a new vanity in the primary bath, along with a curbless walk-in shower that brings a clean, modern look and everyday ease. The open flow from kitchen to living makes hosting simple, whether it's a full dinner or a quiet evening at home.Minutes to shopping, dining, and I-264. Schedule your showing today.

1715 Woodmill Street, South Chesapeake

$585,000

5 Beds ⋅ 2.1 Baths ⋅ 10648409 MLS

Welcome to 3410 Marla Court, tucked away on a quiet cul-de-sac in the sought-after Millers Run community of Chesapeake. Built in 2004, this beautifully maintained 5-bedroom, 2.5-bath home offers over 3,156 square feet of thoughtfully designed living space, combining generous room sizes with modern updates and a fantastic private setting. Fresh paint with newer luxury vinyl plank flooring, the home features an inviting open floor plan that's for both everyday living and entertaining. The spacious family room flows seamlessly into the updated eat-in kitchen, offering abundant cabinetry, ample counter space, high-end stainless-steel appliances and plenty of room for family gatherings. A first-floor bedroom provides excellent flexibility as a guest room, home office, or playroom. Upstairs, the spacious primary suite features a walk-in closet and a private ensuite bath with dual vanities, while the updated hall bathroom has a new walk-in shower which adds a stylish touch for family and guests alike. A two-zone HVAC system helps keep the home comfortable year-round. Step outside to enjoy the screened-in porch overlooking a huge, fully fenced backyard that backs to peaceful woods, creating a private retreat for relaxing, entertaining, or letting children and pets play. Offering space, privacy, modern updates, and a desirable cul-de-sac location, this exceptional Millers Run home is ready to welcome its next owners.

3410 Marla Court, South Chesapeake

$550,000

4 Beds ⋅ 2.1 Baths ⋅ 10649225 MLS

Welcome to 913 Montebello Circle, a one-of-a-kind custom all-brick home designed for buyers who appreciate true craftsmanship, architectural character, and timeless traditional design. Located in the desirable Great Bridge area of Chesapeake, this home offers distinctive features including a stunning wood spiral staircase, custom millwork, rich hardwood flooring, and three fireplaces. Outside, enjoy your own private backyard retreat featuring a saltwater inground pool, perfect for relaxing or entertaining. Ideally located near local military bases, shopping, dining, and major interstates, this is a rare opportunity to own a home filled with character, quality craftsmanship, and lasting value.

913 Montebello Circle, South Chesapeake

$435,000

3 Beds ⋅ 2 Baths ⋅ 10648528 MLS

Welcome to this charming Chesapeake ranch nestled on a full acre! This 3-bedroom, 2-bath home offers 1,620 sq. ft. of comfortable living space with beautiful hardwood floors and an impressive recreation room complete with pool table—perfect for entertaining family and friends. Head outside to the large deck with a covered sitting area and outdoor sink, creating an ideal setting for gatherings and relaxing. The detached 600 sq. ft. in-law suite adds exceptional flexibility for guests, extended family, a home office, or additional living space. With room to spread out, entertain, and enjoy the outdoors, this unique property offers the space and versatility you've been looking for in Chesapeake!

2405 Johnstown Road, South Chesapeake

$815,000

5 Beds ⋅ 3 Baths ⋅ 10648928 MLS

This exceptional, meticulously maintained home offers the feel of new construction with over $75,000 in upgrades and thoughtful owner enhancements. The customized gourmet kitchen features double ovens, a built-in microwave drawer, designer finishes, and a dry bar with beverage refrigerator—perfect for everyday living and entertaining. Upgrades continue throughout with custom window treatments, upgraded lighting, smart-home features, a reverse osmosis water system and more. A first-floor bedroom and full bath make it a perfect property for multi-generational living. Enjoy multiple outdoor spaces, including a welcoming front porch, screened-in porch and expansive patio. A wooded backdrop and full fencing create a private backyard retreat. Located on a quiet street yet just minutes from shopping, dining, and everyday conveniences, this beautifully custom home offers comfort, privacy, and elevated country living. Truly move-in ready and designed for both relaxed living and effortless entertaining.

633 Ambrose Street, South Chesapeake

$434,900

3 Beds ⋅ 2.1 Baths ⋅ 10648817 MLS

Welcome to Bryan's Cove, where low-maintenance living meets exceptional community amenities in the heart of Chesapeake. This beautifully maintained townhome features a first-floor primary suite and an open-concept layout designed for both everyday living and entertaining. The kitchen offers stainless steel appliances, a pantry, peninsula seating, subway tile backsplash, and opens to the dining area and spacious living room highlighted by a custom floor-to-ceiling shiplap fireplace with floating wood shelving. The heated and cooled sunroom provides additional year-round living space, while luxury vinyl plank flooring, a custom frosted glass barn door leading to the primary bath, premium window treatments, and a smart thermostat add thoughtful style and convenience throughout. Outside, enjoy a fully fenced backyard with a stamped concrete patio, pergola, professional landscaping, and attached 2-car garage. Bryan's Cove offers resort-style amenities including a clubhouse, pool, fitness center, playgrounds, and access to the Elizabeth River, all with no flood insurance required. Conveniently located near shopping, dining, interstates, and military bases, this home is ready for its next owner. Incentives may be available through preferred partners. Contact listing agent for details and eligibility. Some photos are virtually staged.

1720 Barkadeer Cove, South Chesapeake

$449,900

3 Beds ⋅ 3.1 Baths ⋅ 10648781 MLS

One of the best homesites in Bryan's Cove! This meticulously maintained end-unit townhome offers exceptional privacy with no neighboring buildings beside or behind it, overlooking the peaceful woods and green space. Enjoy a larger fenced backyard, private composite balcony, guest parking just steps away, and an attached two-car garage. Thoughtfully selected builder upgrades include quartz countertops, upgraded cabinetry, LVP flooring throughout, double wall ovens, upgraded appliances, added lighting, ceiling fans in every room, and a gas tankless water heater. The versatile first-floor flex space with a full bath is perfect for a guest suite, rec room, home office, or fourth bedroom. The primary suite features tray ceilings, a walk-in closet, and an en-suite bath with a double vanity, soaking tub, and shower. Located in sought-after Grassfield, Bryan's Cove offers resort-style amenities including a clubhouse, pool, fitness center, dog parks, playgrounds, beach and dock with private access to the Elizabeth River.

954 Gabion Way, South Chesapeake

$580,000

4 Beds ⋅ 2.1 Baths ⋅ 10648376 MLS

Beautifully maintained and move-in ready, this immaculate 4-bedroom, 2.5-bath home offers 2,668 sq. ft. in the sought-after Grassfield school district. The spacious floor plan features a formal dining room, flexible office or additional living space, and an inviting family room with fireplace and custom built-ins. The family room flows into the updated eat-in kitchen, creating an open, comfortable space for everyday living and entertaining. Updated bathrooms, beautiful hardwood floors and thoughtful details throughout reflect the exceptional care this home has received. Step outside to your own backyard retreat featuring an in-ground saltwater pool perfect for relaxing, entertaining and enjoying warm summer days.

2129 Chesterfield Loop, South Chesapeake

$495,900

4 Beds ⋅ 2 Baths ⋅ 10648870 MLS

Tucked away in the established Deep Creek Landing community, this custom built Cape Cod offers wooded water views and the privacy so many buyers are seeking. The original owner took great care in crafting this home, with great attention to detail. A first floor primary bedroom adds convenience, while two generous upstairs bedrooms each feature large walk-in closets plus ample storage in the eaves. A finished room over the garage provides flexible space for a fourth bedroom, home office, or rec room. The attached one car garage adds ease of access. Generator, sprinkler system, and a whole house fan add peace of mind and comfort year round. This home carries all of its original character, making it a wonderful opportunity for a buyer ready to refresh and personalize. Enjoy the wooded backdrop and the quiet of this beloved neighborhood while being minutes from I-64, shopping, schools, and military bases.

934 Ferryman Quay, South Chesapeake

$537,900

3 Beds ⋅ 3.1 Baths ⋅ 10648704 MLS

To Be Built - Financing 5.75 rate, NO PMI! Minutes to Greenbrier - Joseph’s Meadow Site: 369 Scotland Lane or TOUR MODEL HOME: 910 Bernard Ln. Open Sat/Sun 12-4 - Award-winning builder - Sophisticated Row homes with upgraded building package - Airy 10’ ceilings with 9’ lower and upper floors - Oversized windows - Extensive hardwood - First-floor bedroom w/ensuite bath - 10x20 Covered porch and front porch - Chef’s kitchen: 10’ island, quartz counters, Custom hood, GE Cafe appliance package - Luxurious primary retreat w/two custom closets - Spa bath oversized tiled shower, dual heads, large niche and Dual vanities - Large laundry room - Secondary petite suite w/huge closet and ensuite bath - Nat. Gas Tankless water heater - Finished insulated 2-car garage - Professional ground maintenance - Be home for the holidays!

130 Lenas Way, South Chesapeake

$300,000

3 Beds ⋅ 1.1 Baths ⋅ 10648009 MLS

BEAUTIFULLY UPDATED THROUGHOUT! An amazing opportunity to own your piece of the American dream with this freshly painted 3BR/1.5 bath townhome located in the heart of Greenbrier! From the kitchen with new appliances, hardware and work station sink, to HVAC, water heater and roof (all 2025). Featuring luxurious crown and chair molding, newer flooring and newer Pella and Anderson windows and storm doors. All new ceiling fans and recessed lighting too! Out back, new paver patio, flower garden, pond and hand built privacy fence create a peaceful place to relax. Obvious attention to detail and quality throughout this wonderful home! You'll wanna see this one first!

1215 Cedar Mill Square, South Chesapeake

$425,900

3 Beds ⋅ 2.1 Baths ⋅ 10648576 MLS

Welcome to 458 Blue Beech Way! This spacious 3-bedroom, 2.5-bath home offers a flexible floor plan with two primary suites—one conveniently located on the first floor and another upstairs. The living area features a cozy gas fireplace, while the generous walk-in attic provides abundant storage and potential for additional finished living space, subject to buyer verification and applicable approvals. Enjoy the amenities of this desirable community, including three scenic lakes with fountains, a community pool and clubhouse. Conveniently located near shopping, dining, entertainment and major roadways. Offered at $425,900, this home offers comfort, flexibility and plenty of potential. Schedule your showing today

458 Blue Beech Way, 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.