Chesapeake VA Homes with Wooded View

Welcome to Chesapeake, Virginia, a hidden gem nestled in the heart of the Tidewater region. Known for its rich history, vibrant community, and stunning natural beauty, Chesapeake offers an ideal setting for families, retirees, and anyone seeking a peaceful yet dynamic lifestyle. With its unique blend of urban conveniences and rural charm, this city is a place where you can truly have it all.

One of the standout features of Chesapeake is its picturesque homes with wooded views. Imagine waking up each morning to the serene sights and sounds of nature right outside your window. These homes are expertly designed to embrace the lush greenery that surrounds them, providing a tranquil escape from the hustle and bustle of everyday life. Whether you prefer a cozy cottage or a spacious family home, Chesapeake’s real estate market has something for everyone, all while offering the added benefit of stunning wooded landscapes.

Chesapeake is also home to an array of parks, trails, and recreational opportunities, making it a haven for outdoor enthusiasts. Enjoy hiking, biking, or simply taking a leisurely stroll through the scenic woodlands that define this beautiful area. The community is known for its friendly atmosphere and strong sense of belonging, with local events and activities that bring residents together.

If you’re searching for a home that combines modern living with the tranquility of nature, look no further than Chesapeake, VA. Experience the charm of wooded views and the warmth of a welcoming community, and discover why so many are proud to call this vibrant city their home.

Newest Chesapeake VA Homes with Wooded View

$550,000

3 Beds ⋅ 2.1 Baths ⋅ 10645963 MLS

Wonderful opportunity to get 4+ acres in high rated schools. HUGE outbuilding with 3 bays garage bays, powered, multi-level, for storage and recreational activities. Home sold as is. Part of an estate. Seller to do no repairs.

2323 Herring Ditch Road, South Chesapeake

$699,900

4 Beds ⋅ 3.1 Baths ⋅ 10645155 MLS

Welcome to this beautiful and spacious, well-maintained home that boasts 3261 sq.ft., four 2nd floor Bedrooms, 3.5 Baths + 1st floor Office, Dining Room, Sunroom, Family Room with cozy gas log fireplace, Living Room with handsome built-in bookcases, 12x10 shed, over 1/3rd acre corner lot, 1000 sq.ft. paver patio, 2nd floor Bedroom with ensuite bath & adjacent Loft is perfect for an In-Law Suite. 3 car garage provides ample parking and storage. Come see your dream home today!

2300 Burgess Court, South Chesapeake

$435,000

4 Beds ⋅ 2 Baths ⋅ 10645687 MLS

Welcome to this inviting 4-bedroom ranch in the sought after Mill Creek neighborhood. Freshly painted throughout with brand new carpet and a new roof, this home is truly move-in ready. Enter into a bright living room featuring vaulted ceilings and a cozy wood-burning fireplace, seamlessly opening to the fully remodeled kitchen. The kitchen shines with white shaker soft-close cabinets, quartz countertops, and stainless steel appliances. Two bedrooms sit just off the living room, accompanied by a beautifully updated hall bathroom and laundry room. The spacious primary bedroom offers a remodeled en-suite bathroom and a generous walk-in closet. The FROG provides flexibility as a 4th bedroom, guest space, or bonus room. Out back, enjoy a wood deck overlooking an above-ground pool and a peaceful backyard with views of the wooded area maintained by the Army Corps of Engineers along the Dismal Swamp Canal. The property extends about 10 ft beyond the back fence line. Don't miss this one.

500 Willow Bend Drive, South Chesapeake

$899,900

4 Beds ⋅ 3 Baths ⋅ 10645653 MLS

Welcome to The Ashford by Wetherington Homes - MOVE IN BY AUGUST 2026! 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

$280,000

2 Beds ⋅ 2 Baths ⋅ 10645506 MLS

This fantastic move-in-ready condo has undergone numerous recent upgrades (too many to list).LVP flooring and carpet, fresh paint throughout. 1st floor features include a BR with an attached bath and soaring vaulted ceilings. Tucked away in a secluded area, this property backs up to a private grassy area. Community amenities include a pool.

1641 Orchard Grove Drive, South Chesapeake

$300,000

3 Beds ⋅ 2.1 Baths ⋅ 10645613 MLS

Welcome Home! Thoughtfully updated throughout, this home features brand-new LVP flooring, carpet, fresh paint, blinds & added attic insulation (2026). Updated cabinets, granite countertops, light fixtures, bathroom vanities, and faucets. Major improvements provide peace of mind, including replacement windows and sliding patio doors (2021), a new roof (2017), and a water heater (2018). The spacious layout offers generously sized bedrooms, abundant closet space, and the convenience of a one-car garage. Outside enjoy the fully fenced backyard with a storage shed that backs up to the Indian River Park & inground firepit. The washer and dryer convey, making this home truly move-in ready. With its extensive updates, functional layout, and low-maintenance living, this is one you won't want to miss!

16 Farington Circle, Central Chesapeake

$644,900

4 Beds ⋅ 2.1 Baths ⋅ 10645606 MLS

Ask Agent about a potential VA assumable loan opportunity! Better Than New and Built in 2023, this beautifully and thoughtfully upgraded home offers the benefits of newer construction without the wait. Move-in ready with quick closing available. Bright, open-concept floor plan with abundant natural light. Gourmet kitchen features quartz countertops, oversized island, premium gas range, stainless steel appliances, walk-in pantry, and custom cabinetry. Spacious primary suite includes tray ceiling, dual walk-in closets, soaking tub, tiled shower, and dual vanities. Enjoy covered front and rear porches, extended patio, fully fenced backyard with wooded views, irrigation system, storage shed, custom window treatments, and exceptional attic storage. Convenient to military bases, shopping, dining, and major commuter routes. Trusted lender Steve Hawley (NMLS #1813927) from Southern Trust Mortgage (NMLS #2921) will provide a 1% lender-paid buydown on this listing. Ask Listing Agent for details.

640 Appalachian Court, South Chesapeake

$675,000

6 Beds ⋅ 2.1 Baths ⋅ 10645171 MLS

Rare opportunity to own over 6 private acres in the heart of Deep Creek! This exceptional property includes two parcels conveying with the sale, creating a combined 6+ acres of wooded privacy at the end of a quiet road. The spacious 6-bedroom home offers endless possibilities for multigenerational living, a home office, hobby space, or guest accommodations. Enjoy the peace and seclusion of country-style living while remaining just minutes from shopping, dining, schools, and major interstates. Come see this one first!

3249 Pioneer Lane, South Chesapeake

$225,000

2 Beds ⋅ 2 Baths ⋅ 10645413 MLS

Hard to find single level living! Newer LVP flooring in main living area, carpet in bedrooms less than 2 years old, galley kitchen and updated light fixtures. End unit tucked away but right across from the pool! All new windows and sliding glass door, move in ready.

1012 Rue Marseille, South Chesapeake

$529,900

4 Beds ⋅ 2.1 Baths ⋅ 10645403 MLS

You have seen the pictures and now I am sure you are curious about everything this house has to offer. Well, it is absolutely 100% turn-key, move-in ready with all of the bells and whistles. The home feels so good and invites tons of natural light. The kitchen has been thoughtfully remodeled adding tons of cabinet space, a center island, a pot filler and more functional layout. The cabinets, flooring (hand scraped bamboo), counters and appliances have all been recently upgraded as well. The bathrooms have all been remodeled and the primary bath is a small piece of heaven. Separate sinks, dual shower heads in the tile/glass shower and a separate soaking tub. Go outside and you might not go back in for quite a while. A covered porch and expansive deck greet you with the hot tub around the corner. Drop down to the 28,000 gallon in-ground pool complete with a built-in endless pool for serious swimmers. Backing up to the woods, this private, backyard paradise awaits you!

2107 Sunset Maple Lane, South Chesapeake

$765,000

5 Beds ⋅ 2.1 Baths ⋅ 10645076 MLS

Why wait on new construction when this one's already done? This home was taken all the way down to the foundation and completely rebuilt and expanded — outside of one corner of the home everything here is new. Home inspection is complete, every item addressed, so you can move in with genuine peace of mind. Tucked away on a quiet country road in Chesapeake and surrounded by 3 peaceful acres of mature trees, this modern farmhouse ranch offers the privacy and charm buyers dream about. Huge wraparound-feel porches front and back give you outdoor living space to spare, and the wide-open yard makes this property feel like a true retreat. Inside, gorgeous LVP flooring flows throughout, while the spacious living area with a stunning brick fireplace creates a warm gathering space. The farmhouse-inspired kitchen features white cabinetry, an oversized island with bar seating, and ample storage. Bedrooms are thoughtfully spaced for added privacy, while the hall bath offers a double vanity, step-in shower, and beautiful natural light. The primary suite feels like its own getaway, with private porch access, dual closets, and a spa-style bath featuring a floor-to-ceiling marble-tiled shower. A detached storage shed conveys, and the sprawling backyard offers endless possibilities — gardening, entertaining, or future additions. All the character of country living, with the peace of mind of a brand new home. Welcome home.

1629 Shillelagh Road, South Chesapeake

$399,900

3 Beds ⋅ 2 Baths ⋅ 10645064 MLS

All brick ranch on expansive 1/2 acre lot with views of the river! 3 bedrooms with hardwood floors in most of the living areas. Impressive Sunroom addition allows for great family gatherings. Kitchen with gas cooktop. Covered carport and detached garage with lots of potential. Roof appx 5 yrs old.

2749 E Meadow Drive, 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.