Chesapeake VA Homes with Wooded View

**Discover the Charm of Chesapeake, VA: Your Ideal Home Awaits**

Nestled in the heart of Hampton Roads, Chesapeake, Virginia, is a captivating blend of natural beauty and suburban comfort. Known for its rich history, diverse culture, and thriving community, Chesapeake offers an exceptional quality of life that appeals to families, retirees, and everyone in between. With its lush parks, scenic waterways, and vibrant neighborhoods, it’s no wonder that this city is a sought-after destination for homebuyers.

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 often boast expansive backyards that seamlessly blend with the surrounding landscape, providing a tranquil retreat from the hustle and bustle of daily life. Whether you’re sipping your morning coffee on the deck or hosting a family barbecue, the beauty of the woods creates a perfect backdrop for cherished memories.

Chesapeake is also home to a wealth of amenities, including top-rated schools, shopping centers, and recreational facilities. With miles of hiking and biking trails, as well as access to the picturesque Great Dismal Swamp National Wildlife Refuge, outdoor enthusiasts will find plenty of opportunities to explore and enjoy the great outdoors.

In Chesapeake, you’re not just buying a home; you’re investing in a lifestyle filled with natural beauty, community spirit, and endless possibilities. Come discover your dream home with a wooded view in this enchanting city, where every day feels like a getaway!

Newest Chesapeake VA Homes with Wooded View

$825,000

4 Beds ⋅ 3.1 Baths ⋅ 10648270 MLS

Beautiful custom home on 3 Acres that backs up to woods! Two Primary Suites, one downstairs and one upstairs each with their own full bath! Amazing custom Kitchen with loads of storage, Pantry, plenty of counter space, center island, brand new cabinets, granite and Stainless Steel Appliances! Dual zoned central Heat/AC. Move in ready! Located in the Grassfield School district! Completely remodeled and waiting for you, be sure to come check this one out first!No HOA, bring your horses, chickens and goats!

2239 Benefit Road, South Chesapeake

$653,900

4 Beds ⋅ 3 Baths ⋅ 10648204 MLS

The Marigold is a thoughtfully designed rear-load home that blends convenience, elegance, and flexible living. With 2,703 square feet, this home offers four bedrooms to fit your needs. Upon entry, a dining area leads you into the upgraded gourmet kitchen and open great room. Enjoy a first floor owner's suite with tray ceilings, a spacious walk-in closet, and a upgraded deluxe spa-inspired bath. The first floor also includes a secondary bedroom, full bath, and laundry room for added convenience. Upstairs, You'll also find 2 additional bedrooms, a hall bath, and a versatile bonus room ready to become whatever you need most.

1956 Paw Paw Place, West Chesapeake

$639,900

4 Beds ⋅ 3 Baths ⋅ 10648148 MLS

1949 Paw Paw Place, West Chesapeake

$794,900

6 Beds ⋅ 3 Baths ⋅ 10647933 MLS

Welcome to your home! Like new construction maticulously well maintained home sits on a quiet culdesac in the highly desired sought-after Great Bridge High School - Johnstown Estates. Featuring 6 bedrooms, 3 bathrooms with one bedroom downstairs. Magnificent well equipped gourmet kitchen with quartz counter tops, stainless steel appliances and large island that overlooks to spacious family room with gas fireplace. The upstairs primary suite offers a luxirious bathroom with double vanity and lard walk in closet. This home includes a 2 zone HVAC system and a tankless water heater for added effeciency. Gutters system and vinyl privacy fence. Conveniently located near shopping, restaurants, and highways.

1024 Loutro Court, South Chesapeake

$399,900

3 Beds ⋅ 1.1 Baths ⋅ 10647071 MLS

Charming Brick Ranch in the Heart of West Chesapeake! This adorable 3-bedroom 1.5 bath ranch-style home sits on a spacious .39-acre lot and is move-in ready! Enjoy a freshly painted interior, new flooring & more. The home features a formal living room and dining room, a cozy wood burning fireplace. Additional highlights a detached oversized garage- great for a workshop, extra storage, or hobby’s space. Located in the established Chadswyck Terrace West neighborhood with easy access to shopping, dining, and major routes. No HOA! Don’t miss this gem-schedule your showing today!

2168 Armada Drive, West Chesapeake

$335,000

3 Beds ⋅ 2.1 Baths ⋅ 10648047 MLS

One owner condo - shows like a model - professionally decorated - updates include flooring - kitchen - baths - systems - so well cared for - maintained - Cul-de-sac that borders the golf course - no thru traffic - duplex style condo with a garage and driveway parking - In the heart of Greenbrier on the 11th green of the Greenbrier Golf Course - wooded view out the back of the fenced in yard.

1016 Winged Foot Court Court Unit B, South Chesapeake

$653,900

5 Beds ⋅ 4.4 Baths ⋅ 10647953 MLS

Welcome home to this stunning brand new 2 story model,  designed with modern style, comfort, and functionality. Offering 5 spacious BDRs, 4.5 BTHS, this home features an open-concept floor plan that's perfect for both daily living & entertaining. Features of our gourmet kitchen are  upgraded quartz countertops, upgraded appliances, abundant cabinetry, & a large island that overlooks the spacious living area.  LVP flooring flows throughout the first floor, while 9-foot ceilings & elegant crown molding adding sophisticated touch. A first-floor BR with full bath provides the perfect space for guests,  or a private home office. Upstairs, you'll find generously sized bedrooms, with walk in closets. and a loft offering endless possibilities with additional living space. Exceptional community amenities include a beautiful clubhouse, community pool, playgrounds, a covered pavilion with picnic areas, and outdoor recreation spaces perfect for gathering with family and friends. Surrounded by natural beauty, this community offers a peaceful setting while remaining conveniently close to shopping, dining and highways. Don't miss the opportunity to own a beautiful home in one of the area's most desirable new-home communities.

1957 Paw Paw Place, West Chesapeake

$655,900

5 Beds ⋅ 4.1 Baths ⋅ 10647980 MLS

Welcome home to this stunning brand new 2 story model, designed with modern style, comfort, and functionality. Offering 5 spacious BDRs, 4.5 BTHS, this home features an open-concept floor plan that's perfect for both daily living & entertaining. Features of our gourmet kitchen are  upgraded quartz countertops, upgraded appliances, abundant cabinetry, & a large island that overlooks the spacious living area.  LVP flooring flows throughout the first floor, while 9-foot ceilings & elegant crown molding adding sophisticated touch. A first-floor BR with full bath provides the perfect space for guests,  or a private home office. Upstairs, you'll find generously sized bedrooms, with walk in closets. and a loft offering endless possibilities with additional living space. Exceptional community amenities include a beautiful clubhouse, community pool, playgrounds, a covered pavilion with picnic areas, and outdoor recreation spaces perfect for gathering with family and friends. Surrounded by natural beauty, this community offers a peaceful setting while remaining conveniently close to shopping, dining and highways. Don't miss the opportunity to own a beautiful home in one of the area's most desirable new-home communities.

1948 Paw Paw Place, West Chesapeake

$560,000

4 Beds ⋅ 2.1 Baths ⋅ 10647434 MLS

Welcome to this beautifully maintained home in Joliff Woods! Offering approx 2,400 square feet of living space, this spacious 4-bedroom, 2.5-bath residence combines comfort, style, and functionality. Step inside to a beautiful two-story foyer filled with natural light, creating a bright and inviting first impression. The main level features engineered hardwood flooring, a well-appointed kitchen with stainless steel appliances, and a spacious family room highlighted by a cozy gas fireplace and custom built-in cabinetry—perfect for everyday living and entertaining. Situated on a generous 0.63-acre lot, the backyard is an entertainer's dream, featuring a large new deck with in-ground pool and expansive yard, providing the ideal setting for summer gatherings, outdoor dining, or simply relaxing in your own private retreat. Upstairs, you'll find four generously sized bedrooms with abundant closet space. The impressive primary suite offers a walk-in closet ,a spa-inspired ensuite bath with a jetted soaking tub, separate walk-in shower, and plenty of room to unwind. Additional features include ceiling fans throughout, elegant dining room light fixtures, and ample storage. Don't miss this incredible opportunity to make it yours!

4936 Oriole Drive, West Chesapeake

$839,500

5 Beds ⋅ 3 Baths ⋅ 10647712 MLS

New Home by Custom Builder in Martin’s Point (Western Branch) main floor living, 4 or 5 bedroom plan. First floor primary bedroom with luxury bath- zero entry tiled shower & free standing tub, Open floor plan with Huge Gourmet Kitchen w/ Quartz counter tops, 36” gas cooktop with built-in microwave/oven, Cathedral Ceiling Family Room w/ Beamed ceiling, amazing stone fireplace with built-in bookcases, expansive covered porch (29’x10’) overlooks a privately wooded backyard & scenic view .42 acre. 3 Bedrooms & Study with French doors on 1st floor with 2 add'l large rooms on the second floor, 3 baths. Excellent location, easy access to I-664, near schools, shopping, Custom Builder is a member of Southern Living Custom Home Builder Program (since 1993). Superior quality features include Trane HVAC system, tankless hot water heater, custom cabinetry, large utility room/drop zone, Hardie Plank exterior, quality upgrades throughout. Fully sodded and irrigated yard.

3909 Bruce Road, West Chesapeake

$449,900

3 Beds ⋅ 2.1 Baths ⋅ 10647748 MLS

Rain or shine, the screened porch is calling. This move-in ready end-unit Nansemond floorplan in The Retreat at Western Branch offers low-maintenance living with a first-floor primary suite, 2-car garage, open-concept layout, and abundant natural light. The kitchen features bar seating overlooking the living room with a cozy gas fireplace, plus a spacious walk-in pantry to keep everything organized. Your favorite spot just might be the screened, covered rear porch. Upstairs offers two additional bedrooms, a loft, guest bath, and walk-in attic. Resort-style amenities include a clubhouse, pool, outdoor kitchen, fire pit, billiards, fitness center, community garden, dog park, and beautifully landscaped grounds.

4607 Longleaf Place, West Chesapeake

$630,000

4 Beds ⋅ 3 Baths ⋅ 10647334 MLS

Welcome to Beautiful Briarwood, located in the HEART of Great Bridge! This Elegant Brick Colonial is a MUST SEE! Home features 4 spacious bedrooms, 3 full baths, dual stair cases & two gas fireplaces. The 2-zone HVAC & gas water heater updated in 2026. Kitchen features Corian countertops & stainlesss Steel appliances. Enjoy the NEW deck, fenced in backyard, and low traffic cul-de-sac. Come connect your heart with this HOME!

708 Shadowfield Court, 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.