Chesapeake VA Homes with Wooded Exterior features

Welcome to Chesapeake, Virginia – a captivating blend of suburban charm and natural beauty. Nestled in the heart of Hampton Roads, Chesapeake is renowned for its lush landscapes, vibrant communities, and rich history. With over 22,000 acres of parks and green spaces, it’s a haven for outdoor enthusiasts and families alike. The city boasts a unique mix of urban conveniences and serene environments, making it an ideal place to call home.

One of the standout features of Chesapeake’s real estate market is its stunning homes with wooded exterior features. Imagine waking up to the gentle rustle of leaves and the soft melodies of chirping birds right outside your window. These homes, often surrounded by mature trees and lush foliage, offer a tranquil retreat from the hustle and bustle of daily life. The wooded exteriors not only provide a picturesque backdrop but also enhance privacy, creating a serene sanctuary for you and your loved ones.

Whether you’re looking for a cozy cottage nestled among towering pines or a spacious family home with expansive wooded views, Chesapeake has a diverse range of properties to suit your lifestyle. Many of these homes feature modern amenities while retaining their natural charm, allowing you to enjoy the best of both worlds.

With its friendly neighborhoods, excellent schools, and easy access to the Chesapeake Bay and Atlantic Ocean, this city is perfect for those who appreciate nature and community. Explore the enchanting homes with wooded exteriors in Chesapeake and discover your dream sanctuary today!

Newest Chesapeake VA Homes with Wooded Exterior features

$629,900

4 Beds ⋅ 2 Baths ⋅ 10655393 MLS

Welcome home to this charming 4-bedroom, 2-bath brick ranch nestled on 4.22 wooded acres at the end of a quiet cul-de-sac. Inside, you'll find a warm and inviting layout featuring a family room with a wood-burning fireplace, formal living and dining rooms, granite countertops, and beautifully updated primary and hall bathrooms. Step outside to relax on the new composite deck (2024), gather around the fire pit, or enjoy the peaceful wooded surroundings. The property also includes a detached 2-car garage with a finished studio apartment and full bath, plus a whole-house generator and water softener for added convenience. Offering space, privacy, and versatile living, this property is ready to welcome you home!

1345 Oak Ridge Drive, South Chesapeake

$975,000

6 Beds ⋅ 3.1 Baths ⋅ 10655175 MLS

Discover a private country retreat in the heart of Grassfield, where approximately 5 tree-lined acres create a peaceful setting rarely found with this much space and convenience. Over 4,000 sqft of living space with 6 beds, 3.5 baths, first floor primary ensuite. Spend summer days by the pool, unwind beneath the stars in the hot tub, or enjoy the freedom of acreage with a barn and zoning that permits horses. Mature trees frame the property and provide a sense of privacy while still placing you in the heart of Chesapeake, convenient to shopping, dining, schools and major routes.

2536 Seven Eleven Road, South Chesapeake

$849,900

4 Beds ⋅ 3 Baths ⋅ 10655045 MLS

Welcome to The Ashford by Wetherington Homes -Move-In Ready! 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

$585,000

3 Beds ⋅ 2 Baths ⋅ 10654878 MLS

Welcome home to this well-maintained brick ranch situated on approximately 1.5 acres in North Landing Farms. Recently appraised, this 3-bedroom, 2-bath home offers 1,773 sq. ft. of single-level living with a fireplace, covered front porch and large rear deck. A climate-controlled attached 2-car garage/workshop with upstairs workspace/storage provides excellent space for vehicles, hobbies and projects. Additional outdoor features include a barn, storage shed, raised garden beds, chicken run and grape arbor. HVAC, water heater and appliances are approximately 7 years old. No HOA! Zoned for Hickory Middle and Hickory High School. Enjoy plenty of space, privacy and versatility in this unique Chesapeake property. Schedule your private showing today!

552 Saddlehorn Drive, South Chesapeake

$674,900

5 Beds ⋅ 4 Baths ⋅ 10654517 MLS

Welcome to this exceptional 5-bedroom, 4-bathroom, 3,250-square-foot Craftsman-style home, custom built by Summit Construction and ideally situated in the heart of Great Bridge on a quiet cul-de-sac. From the moment you step inside, you’ll appreciate the thoughtful design, quality craftsmanship, and extensive upgrades throughout. The spacious open-concept floor plan is perfect for both everyday living and entertaining, featuring beautiful true hardwood floors, a stunning stone fireplace with custom mantel, and an abundance of natural light. At the heart of the home is the impressive designer kitchen, complete with quartz countertops and backsplash, stainless steel appliances, and a convenient butler’s pantry featuring a wet bar and wine cabinet. The luxurious primary suite offers a gorgeous custom closet and a spa-inspired bathroom with a large tiled shower and relaxing soaking tub. A first-floor bedroom with its own ensuite bath provides an ideal space for guests, multigenerational living, or a private home office. Upstairs, you'll find additional generously sized bedrooms and thoughtfully designed living spaces. Step outside and enjoy your own private retreat with a large screened-in porch and an outdoor gas fire pit—perfect for relaxing, entertaining, and enjoying the outdoors throughout the year. There's also space designated for a future hot tub with reinforced concrete slab. Energy efficiency was also a priority, with upgraded spray-foam insulation helping enhance the home's overall efficiency and comfort. With its desirable Great Bridge location, spacious floor plan, exceptional finishes, and inviting indoor and outdoor living spaces, this beautifully crafted home offers the perfect combination of style, comfort, and functionality. Don’t miss the opportunity to make this remarkable home your own!

404 Foxgate Court, South Chesapeake

$325,000

3 Beds ⋅ 1.1 Baths ⋅ 10654363 MLS

Come tour this ranch home with beautiful hardwood floors and a functional living space. This property has a partially open floor plan with a versatile layout. The open room space can be used to entertain, as an office, or as spare living space. The backyard is large and wooded, offering a storage shed and plenty of space for gardening and entertaining. The dishwasher, water heater, and refrigerator are all new (2025) and convey with the property.

1025 Shore Road, South Chesapeake

$480,000

4 Beds ⋅ 2.1 Baths ⋅ 10654173 MLS

Welcome to this beautiful one-owner ranch-style home featuring FIVE bedrooms, 2 1/2 baths and a 2-car garage. Situated on a cul de sac and in a neighborhood where homes rarely come on the market, this home is a real find! Enter via the spacious foyer, flanked by formal living and dining rooms, each boasting tray ceilings. Continue in and cozy up by a centrally-featured fireplace in the huge, open family rm, w/ full view of kitchen & large breakfast area. Brand new stainless steel appliances & new flooring are highlights of the kitchen, and brand new carpet runs through the entire downstairs. The en-suite primary lies on one side of the home with three bedrooms and full bath located on the other side. The room over the garage serves as the 5th bedroom. Entire home has been professionally painted & cleaned. Notes: new roof in 2020, extra replacement windows in storage, tons of garage cabinets, shed. Washer, dryer, well/pump work but convey AS IS. Location is so convenient to everything!

717 Treetop Lane, South Chesapeake

$415,000

4 Beds ⋅ 2 Baths ⋅ 10654279 MLS

Welcome home to peaceful country living on approximately 0.71 acres! This inviting ranch-style home offers 4 bedrooms and 2 full bathrooms, with fresh paint throughout, new LVP flooring, and new carpet making it move-in ready. The spacious living room features vaulted ceilings, while the kitchen opens to a cozy breakfast nook perfect for morning coffee or casual meals. Out back, enjoy a private yard surrounded by wooded views, an ideal setting for relaxing, entertaining, or simply enjoying a little extra peace and quiet. Tucked away in a country setting yet conveniently located just off Highway 17, this home gives you the best of both worlds: room to breathe with easy access to everything you need.

5144 Ballahack Road, South Chesapeake

$580,000

4 Beds ⋅ 2.1 Baths ⋅ 10654039 MLS

Welcome home to this spacious 4-bedroom, 2.5-bath two-story home offering approximately 2,800 square feet in the Grassfield High School district. With both a formal living room and dining room, a large family room, and an eat-in kitchen, there’s plenty of space to gather, entertain, and make yourself at home. An additional bonus room offers great flexibility for a home office, study, craft room, or whatever fits your lifestyle. Enjoy beautiful views of the 14th hole of the Las Gaviotas Golf Course right from home. Vacant and ready for its next owners—come see how easily you can picture yourself calling this pretty house home!

523 Las Gaviotas Boulevard, South Chesapeake

$650,000

4 Beds ⋅ 2.2 Baths ⋅ 10653782 MLS

Former Home-A-Rama award-winning home with character you simply don't find every day. Tucked away on a .43-acre cul-de-sac lot, this 3-story Victorian-style home offers approximately 3,100 sq. ft. of living space and a wrap-around porch. Inside you'll find hardwood floors, generous living and dining spaces, custom details, two fireplaces and two staircases. The gourmet kitchen features quartz countertops, black stainless appliances, custom cabinetry, island and pantry. Spacious bedrooms lead to an impressive primary suite with walk-in closet, ensuite bath and fireplace. A third-level bonus space offers flexibility for an office, study or workout room. Outside, an in-ground saltwater pool, multi-level deck, gazebo, fire pit and expansive backyard create a setting for entertaining or relaxing. A truly unique home ready for its next chapter!

302 Honey Locust Way Way, South Chesapeake

$1,100,000

4 Beds ⋅ 2.1 Baths ⋅ 10653479 MLS

Three wooded acres. A saltwater pool. Five garage bays. Room for the boat, RV and workshop. And no HOA. 1741 Taft Road offers a combination that’s increasingly hard to find in Southern Chesapeake. The approx. 3,700-sq.-ft. home features 4 bedrooms, 2.5 baths and a welcoming wraparound porch. Inside, the kitchen is equipped with matte white Café appliances including a gas range, while the spacious living room centers around a wood-burning fireplace. Upstairs are 4 generously sized bedrooms, including a primary suite with 2 walk-in closets. A finished third floor adds 2 large bonus rooms, creating flexible space for a nursery, home office, gym, studio or private retreat. Outside, an approx. 32,000-gallon saltwater pool and composite deck anchor the backyard, with major pool components updated in 2025–26. A heated 2-car attached garage is joined by a 3-bay detached garage/workshop with propane heat plus mini-split heating and cooling. Covered paved storage accommodates a boat, camper or RV, with a pole barn and additional storage shed adding even more versatility. The acreage continues beyond the rear gate into the woods, where walking trails extend the ways to enjoy the property. Extensive paved parking and a private setting complete a property that offers breathing room without giving up convenient access to Chesapeake.

1741 Taft Road, South Chesapeake

$725,000

5 Beds ⋅ 4 Baths ⋅ 10653705 MLS

3 acres! Farm animals allowed - horses, chickens, etc! Enjoy country living right in the heart of Great Bridge! This property offers a rare combination of space, privacy, and convenience. Inside, you’ll find a spacious, well-maintained home with a flexible floor plan. The eat-in kitchen features white cabinetry, generous workspace, and plenty of room for everyday meals and gatherings. The first floor offers a primary bedroom plus two additional bedrooms, a sunroom, and spacious rec room that could also serve as a den or office. Upstairs you will find two more bedrooms, a full bath, and a huge attic providing exceptional storage. A standout feature is the private in-law suite/apartment above the oversized attached garage. With its own separate entrance, this versatile space is ideal for extended family, guests, a private home office, or potential income-producing space. This is a 6th bedroom space so not in the 5 bedroom count. Outside is where this property really sets itself apart. With 3 acres and no HOA, you’ll have the freedom and space that can be hard to find in Great Bridge. There’s plenty of room for an RV, boat, trailers, recreational vehicles, and all your other toys. The oversized attached garage offers abundant storage, while multiple storage sheds provide even more room for lawn equipment and outdoor gear. A large detached workshop with electricity is perfect for hobbies, projects, equipment, or anyone needing a dedicated workspace. Whether you’re looking for multi-generational living, room for your hobbies and vehicles, additional storage, or simply more land and breathing room, this property offers so many possibilities. A unique opportunity to enjoy 3 acres and a true country-living feel without giving up the convenience of Great Bridge! Roof - 4 yrs old, HVAC - 2 yrs old. City sewer. Well has built in Kinecto Water Softener.

429 Warrick Road, South Chesapeake

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