Chesapeake VA Homes with Wooded View

Welcome to Chesapeake, Virginia, a hidden gem nestled in the heart of Hampton Roads. Known for its lush landscapes and vibrant community, Chesapeake offers a unique blend of suburban tranquility and urban convenience. With its rich history, diverse culture, and an abundance of outdoor recreational opportunities, this charming city is the perfect place to call home.

One of the standout features of Chesapeake is its stunning homes with wooded views. Imagine waking up each morning to the serene sights and sounds of nature right outside your window. These properties are often surrounded by picturesque trees, providing a sense of privacy and peace that is hard to find in more densely populated areas. Whether you’re sipping your morning coffee on the deck or enjoying an evening stroll through your backyard, the beauty of the natural landscape will always be a part of your daily life.

Chesapeake is not just about beautiful homes; it’s also about community. Residents enjoy access to top-rated schools, a variety of parks, and numerous recreational activities, including hiking, biking, and fishing in the nearby waters. The city’s commitment to preserving green spaces ensures that the charm of nature remains an integral part of the community.

With its combination of scenic beauty, convenient amenities, and a strong sense of community, Chesapeake, VA, is an ideal location for those seeking a home with a wooded view. Explore the possibilities and discover the perfect blend of comfort and nature in this enchanting city!

Newest Chesapeake VA Homes with Wooded View

$1,300,000

4 Beds ⋅ 2.1 Baths ⋅ 10654856 MLS

Elegant custom details and room to live the life you’ve imagined! Sweeping down a long, paved driveway, this beautiful 4-bedroom home pairs comfortable country living with a thoughtfully arranged estate. Set on over 12 pristine acres in Chesapeake, zoned for Hickory schools, this property is a rare rural sanctuary. A wraparound porch welcomes you inside to 9' ceilings, 8' doors, and reclaimed knotty pine floors. The living room features a stone fireplace, opening to a bright kitchen with soft-close cabinets, Samsung Bespoke appliances, and butler’s pantry. Outside, enjoy a saltwater pool, fire pit, and private porches within a completely fenced in yard. The farm boasts a 6-stall barn with wash station, hot water, and mini-split, plus 5 watered pastures, 3 run-ins, and a 50x42 Morton building. An additional 1.5 acres offers potential for a riding arena or agriculture gardening, while a chicken coop, fruit trees, and berries complete the setting. Enjoy southern Chesapeake's rural character, with conveniences and Route 168 nearby.

1713 Sanderson 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

$525,000

5 Beds ⋅ 3.1 Baths ⋅ 10654949 MLS

Classic character meets seriously usable space. Tucked beneath the trees in the highly desirable Silverwood neighborhood, this 5 bedroom, 3.5 bath Dutch Colonial brings together original character and thoughtful updates without losing its charm. Natural light fills the rooms and plays across the original refinished hardwood floors, bringing warmth throughout the 2,602 square foot home. The brand-new kitchen brings new cabinetry, countertops, appliances and LVP, while the stunningly updated bathrooms add a fresh, polished finish. A gas fireplace adds another touch of original character to the living room, and the finished room over the garage offers flexible space for whatever the home needs. The EZBreeze porch takes outdoor living a step further, with heat and air conditioning that keep the space comfortable throughout all the seasons. Whether enjoying a mild morning or settling in on a cooler evening, this is outdoor space with the comfort to make it genuinely usable year-round. A home with the kind of character you notice right away, paired with a fresh kitchen, beautiful updates, and spaces that make you want to stay awhile. Move in with nothing to do!

3208 Pineridge Drive, West 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 detached 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

$715,000

6 Beds ⋅ 3 Baths ⋅ 10654725 MLS

Your weekends just got an upgrade at 728 Angel Wing Drive! Located in the sought-after Grassfield school district, this meticulously maintained home offers 5 bedrooms, 3 full baths, and a media room that could serve as a 6th bedroom. A first-floor bedroom and full bath are ideal for multigenerational living or guests, while a space for a home office and formal dining room add flexibility. Your private backyard oasis features a saltwater pool, spacious patio, and pergola overlooking peaceful woods with no rear neighbors. Perfect for poolside afternoons and football Sundays! The oversized garage includes shelving and a dedicated workspace. Freshly painted inside and out within the past 3 years and cared for by just two owners, this home also features a whole-house water softener, separate drinking water system, and 32 fully paid-off solar panels for potential monthly energy savings. Thoughtful upgrades, exceptional outdoor living, and room for everyone. Your next chapter starts here!

728 Angel Wing Drive, 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

$879,900

4 Beds ⋅ 2.1 Baths ⋅ 10654253 MLS

The perfect farmhouse that’s a mix of privacy and closeness to local amenities. Sitting on approx 3 acres in Albemarle Farms, this home offers the updates you've been looking for. Step inside to a bright, welcoming interior with engineered hardwood floors, fresh paint throughout, new trim, and a beautifully updated kitchen. Completed in 2025, the kitchen features all-new cabinetry, quartz countertops, a large island, white stone backsplash, new appliances, and a new sink and faucet. Just beyond, the great room is centered around a new stone fireplace and mantle, while the 4-season room offers a flexible space to relax, work, or enjoy views of the property. Upstairs, the primary suite features a soaking tub and walk-in shower, with two additional bedrooms and bonus space offering plenty of flexibility. Major improvements include new heating and cooling units, new ductwork upstairs and downstairs, a new tankless water heater, and new downstairs subfloor. Outside is where this property really shines, with a saltwater in-ground pool, expansive deck, covered rear porch, circular driveway, and plenty of room to enjoy the wooded setting. An oversized garage with a finished room above adds even more usable space. Located in the Hickory school district with no HOA, this is a home with room to settle in, spread out, and enjoy both indoors and out. Incentives may be available through preferred partners. Contact listing agent for details and eligibility.

609 Fairfield Drive, South Chesapeake

$246,500

2 Beds ⋅ 1.1 Baths ⋅ 10654041 MLS

A Diamond Condo with NO FEES! Located in the highly sought-after Grassfield school district, this condo has had a complete transformation. Walk into a beautiful cathedral ceiling and unique reading nook under the stairs. New SS Appliances in the kitchen, new luxury vinyl floors, bedroom/office downstairs with laundry,Beautifully renovated full bathroom. Private upstairs bedroom with half bath spacious closet space and attic storage access. Partially fenced backyard. This is in a quiet neighborhood conveniently located near interstates and shopping. Hurry, before this one is gone!

102 Diamond Avenue Unit D, South Chesapeake

$625,000

5 Beds ⋅ 3 Baths ⋅ 10654148 MLS

Proposed new construction by an award-winning builder featured in past Homearama! Custom open design with a desirable 1st-floor bedroom, spacious living areas and upgraded features included. Enjoy a great yard with room to spread out and the feel of country living while still convenient to major shopping, dining, schools and everyday amenities. NO HOA fees! Anticipated delivery late 2026/early 2027. Get involved early for the opportunity to make certain selections, subject to builder schedule and allowances. One inventory home is currently available for more immediate delivery, and smaller plans may also be available. Great opportunity and value for new construction! Room to install a pool. Call listing agent for plans, pricing, specifications, allowances, construction status and available options.

622 Ambrose Street, South Chesapeake

$539,900

4 Beds ⋅ 2.1 Baths ⋅ 10654089 MLS

Located in the highly sought-after Jolliff Landing neighborhood of Western Branch, this like-new home has tons to offer! Backing to a protected preserve, you’ll have added privacy with no future construction behind you. Featuring an open floor plan with a versatile bonus/flex room and beautiful LVP flooring throughout the main living areas. The gourmet kitchen is equipped with stainless steel appliances, a gas range, quartz countertops, and a custom tile backsplash. A large center island makes entertaining easy, while the cozy gas fireplace adds warmth and charm to the living space. Additional upgrades include smart blinds, smart ceiling lighting in the living room, and an updated primary walk-in shower with a glass door. The community provides amenities such as a pool, walking trails, parks and plazas with outdoor seating, a playground, natural preservation areas, and a state-of-the-art clubhouse with kitchen, conference room, and fitness center. New construction without the wait! Schedule your showing today!

2216 Hampton Roads Parkway, West 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.