Chesapeake VA Homes with Wooded Exterior features

Welcome to Chesapeake, Virginia, a charming county located in the heart of the state. Chesapeake is known for its beautiful landscapes, friendly communities, and rich history. With a perfect blend of urban amenities and suburban tranquility, Chesapeake offers a high quality of life for its residents.

If you appreciate the beauty of homes with wooded exterior features, Chesapeake has plenty to offer. Imagine coming home to a cozy retreat surrounded by lush trees and nature's serenity. Homes with wooded exteriors not only provide a picturesque setting but also offer privacy and a peaceful ambiance.

Whether you are looking for a rustic cabin nestled in the woods or a modern home with a touch of nature, Chesapeake has a variety of options to suit your preferences. From spacious yards to scenic views, homes with wooded exterior features allow you to connect with the outdoors without sacrificing comfort and style.

If you are ready to find your dream home in Chesapeake, explore the listings to discover the perfect property that combines the beauty of nature with the comfort of modern living. Let Chesapeake be the place where you can unwind, recharge, and create lasting memories in a home that reflects your unique style.

Newest Chesapeake VA Homes with Wooded Exterior features

$998,895

5 Beds ⋅ 3.1 Baths ⋅ 10652907 MLS

Experience luxury living in this one-of-a-kind Chesapeake retreat, nestled on a 3-acre lot in the Grassfield School District. This custom-built home blends modern comfort with timeless charm, offering an open-concept first floor design for today's lifestyle. The spacious family room flows seamlessly into the remodeled 2024 kitchen, with direct access to the back deck for everyday relaxation or entertaining guests. Choose between two generous primary suites. First floor primary suite features a gas fireplace, dual closets, and a sitting/office area. Second floor primary suite privately located above 3-car garage, offering separation from the additional upstairs bedrooms. Enjoy abundant space for hobbies and storage with two powered sheds, plus peace of mind from the new encapsulated crawl space with vapor barrier. Major upgrades, including the roof, HVAC, and kitchen in 2024, ensures comfort and efficiency for years to come. This exceptional property delivers a rare combination of privacy, space, and freedom with no HOA restrictions, making it a true Chesapeake gem.

1910 Hallmark Way, South Chesapeake

$574,900

4 Beds ⋅ 2.1 Baths ⋅ 10653018 MLS

Located in Oak Bridge Forest, this 4-bedroom, 2.5-bath home offers a spacious layout, an oversized 2-car garage, and a large backyard made for enjoying the outdoors. Inside, a two-story foyer welcomes you into a light-filled floor plan featuring new laminate flooring, installed in 2025, throughout most of the home. The custom-designed kitchen received a complete makeover in 2025 and opens to the family room, creating an easy flow for everyday living and entertaining. Upstairs, the spacious primary suite features a private bath with a double vanity, walk-in shower, and jetted tub, with three additional bedrooms and a second full bath completing the level. Out back, mature landscaping and trees surround an in-ground pool with a new liner installed in 2024 and new pool heater added in 2025. A Trex deck provides additional space to relax or entertain. Additional features include a tankless water heater, sprinkler system, smart-home capabilities, Ring doorbell and exterior security cameras, plus an Invisible Fence encompassing the front and backyard. No HOA! With generous indoor and outdoor space, thoughtful updates, and a backyard ready for pool days and entertaining, this Oak Bridge Forest home has plenty to offer. Incentives may be available through preferred partners. Contact listing agent for details and eligibility.

733 Dissdale Lane, South Chesapeake

$650,000

5 Beds ⋅ 2.1 Baths ⋅ 10652716 MLS

Custom 5-bedroom, 2.5-bath Chesapeake home on a huge half-acre lot, currently zoned for Grassfield High School! This beautifully updated home features an open floor plan, pickled oak hardwood floors, quartz countertops, stainless steel appliances, gas range, custom barn doors, and European-inspired lighting and fixtures. The spacious primary suite offers cathedral ceilings, dual closets, and a private deck with peaceful wooded views. The spa-like primary bath features a freestanding soaking tub and custom porcelain-and-glass shower. Outside, enjoy an expansive deck and plenty of room for outdoor living, entertaining, and recreation. If you’ve been searching for a custom Chesapeake home with space, style, updates, and a large lot, this one deserves a closer look. Schedule your tour today!

2100 Millville Road, South Chesapeake

$749,000

6 Beds ⋅ 3 Baths ⋅ 10652745 MLS

Welcome to this beautiful brick home in the heart of Great Bridge! Situated on a quiet cul-de-sac, this home has it all! The foyer and entrance way are stunning and extend two stories and include a beautiful stair case. A gorgeous new primary shower, trayed primary bedroom ceiling, hardwood flooring and a private deck that offers a peaceful, wooded view. The first floor bedroom/office has direct access to a full bathroom with newer vanity and is just right for multi-generational living. Both HVAC systems are two years young. The heavy lifting has been done here, this one won't last long! See it today before it is SOLD!!!

909 Brice Court, South Chesapeake

$1,000,000

6 Beds ⋅ 3 Baths ⋅ 10652479 MLS

Open House Sat Sept 12 1-3pm. Modern Farmhouse Charm Meets Turnkey Living in Desirable Chesapeake! Discover the modern farmhouse you’ve been dreaming of, where peaceful country living meets thoughtful, top-to-bottom renovation. Set on serene acreage with panoramic wooded views. It embraces the natural surroundings. This beautifully refreshed home is ideal for extended family/multi generational living. Natural light fills the home, showcasing new flooring, fresh interior paint, updated lighting, and beautifully renovated bathrooms. The completely redesigned custom kitchen is the heart of the home, featuring quartz countertops, ceramic backsplash, abundant prep space, an inviting eat-in area and a KitchenAid appliance suite, ideal for everyday living and entertaining. The expansive living area offers plenty of room to gather, while the renovated wood-burning fireplace creates a cozy focal point with a new firebox, flue, chimney cap, and Buck Stove-style insert. Step onto the Trex deck with PVC railing and enjoy peaceful wooded views from the living space, primary suite or deck. The primary suite is a true retreat, featuring a custom-tiled shower with built-in bench and generous niche, deep soaking tub, double vanity and ceramic tile flooring. The expansive custom closet with built ins provides all the space you have been longing for. Additional improvements include an encapsulated crawlspace with dehumidifier, new septic system designed for 10 occupants, finished room over the garage with generous storage, updated downstairs ductwork, new interior and exterior doors and hardware, new lighting throughout, and a freshly graded crushed-aggregate driveway. The painted brick exterior adds a fresh, modern look while preserving brick’s timeless durability and character. Best of all, the home features a highly energy-efficient geothermal HVAC system. From the crawlspace to the exterior, virtually nothing has been overlooked. Renovated by New Again Houses VB. It offers the feel of quality new construction without sacrificing character, space or setting. See it today!

3132 Benefit Road, South Chesapeake

$349,900

4 Beds ⋅ 2 Baths ⋅ 10652315 MLS

Welcome home to this beautifully renovated, move-in-ready home where the big-ticket updates are already DONE! Featuring a NEW roof, NEW HVAC, NEW windows and NEW hot water heater. The gorgeous new kitchen offers granite countertops, a large breakfast bar, stainless steel appliances and a stainless steel farmhouse sink. Enjoy custom tiled bathrooms, spacious walk-in closets, new flooring, fresh paint and updated fixtures throughout. Outside, the fully fenced backyard backs to the woods, offering added privacy and plenty of room to relax or entertain. Conveniently located with easy access to interstates, Harbor View, military bases, shopping, dining and more. Major updates, stylish finishes, a private backyard and a convenient location—this one is ready to welcome you home!

3568 Dunedin Drive, West Chesapeake

$769,000

5 Beds ⋅ 3 Baths ⋅ 10651816 MLS

Stunning one-owner home on 3 treed acres in the sought-after Hickory High School district, with easy access to Virginia Beach! Custom hardwood floors and trim/woodwork throughout, brand new carpet, and new luxury vinyl in the rec room off the garage. Main floor is 100% hardwood. 5 bedrooms plus two bonus rooms over the garage — great for a teenage suite or mother-in-law suite. Spacious great room with fireplace, formal dining room, and breakfast area off the kitchen. Remodeled kitchen features granite countertops, double oven, double sink, and a generous pantry. First floor offers a shelved library/home office. Florida room with screens and Andersen windows throughout, plus skylights including one in the primary suite. Newer Trex composite deck and storage building in back. Encapsulated crawlspace w/ sump pump & dehumidifier (JES). Well on-site, city water, septic. HVAC serviced annually. Lots of space to grow in this sturdy home!

1204 Murray Drive, South Chesapeake

$275,000

3 Beds ⋅ 1.1 Baths ⋅ 10651743 MLS

Room to garden, create, and entertain. A home designed for real use! Located at the end of a dead-end street on a cul-de-sac, this 3-bedroom, 1.5-bath home offers hardwood floors, a comfortable living area, and a full kitchen suite with all the countertop space, cabinets, and storage you need. The house only gets better outside, with an exceptional amount of usable outdoor space. In the front, two driveways provide flexible parking, and a vivacious garden frames the yard and house, leading you to the greenhouse. In the backyard is a large detached workshop, an extra storage shed, a massive deck for entertaining, a separate fire-pit area, and a ready-to-grow garden featuring raised beds and garden arches. Whether you're working on a project, growing fresh produce, or hosting friends, this property offers the space and versatility to make this house the one where everyone gathers.

2704 Misty Point Road, South Chesapeake

$1,519,000

5 Beds ⋅ 4.1 Baths ⋅ 10651679 MLS

Stunning property situated in the heart of Great Bridge on 3 acres! Brand new gourmet kitchen with 6 burner Cosmo range, additional prep sink, new top of the line appliances and custom cabinetry. All new paint, flooring and completely renovated baths and stairwells on first two primary living levels. Bonus third floor complete with full bath, new paint and new flooring! HUGE primary suite complete with fireplace, fantastic walk-in closet and beautiful new bath. The detached 3.5 car garage includes a garage apartment with kitchenette and full bath. New windows, roof, gutters, soffits and pool liner. Absolutely amazing opportunity to secure this gorgeous, move-in ready property. Awesome enclosed patio with hot tub as well as an outdoor kitchen/bar area. This is an entertainer's dream! See it today before it is SOLD!

641 Ravenwoods Drive, South Chesapeake

$285,000

3 Beds ⋅ 2.1 Baths ⋅ 10651296 MLS

Nice brick ranch with wooded views of the park. Great flow in this home with cozy family room with wood burning fireplace. Large lot with detached garage. Great layout. This fixer upper is just waiting for the next owners and updates!

2016 Rokeby Avenue, Central Chesapeake

$230,000

2 Beds ⋅ 1 Baths ⋅ 10651421 MLS

Ranch style home with 2 bedrooms and 1 full bath located in the Plymouth Park neighborhood. Located near shopping, dining and interstate. This home features large fenced yard, covered concrete patio off office area, 2 storage sheds, spacious eat-in kitchen has gas range, new refrigerator, newer Boush dishwasher and open to living room. The utility room has washer/dryer hook-ups and gas hot water heater.

1403 Salton Drive, Central Chesapeake

$419,900

3 Beds ⋅ 1.1 Baths ⋅ 10651314 MLS

Welcome to this beautifully renovated Great Bridge classic! This all-brick ranch sits on an expansive half-acre, wood-lined lot and blends timeless charm with thoughtful 2025 updates. The home was completely renovated in 2025, featuring new flooring, appliances, a refreshed kitchen, and updated bathrooms. The spacious living room is filled with natural light from oversized windows and offers a cozy wood-burning fireplace. A convenient attached one-car garage provides added storage and functionality. Outside, enjoy the expansive, private yard surrounded by mature trees perfect for entertaining, gardening, or simply relaxing. Zoned for all highly sought-after Great Bridge schools, this home offers an exceptional opportunity in one of Chesapeake's most desirable areas!

229 Cedar Road, 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.