Chesapeake Homes with Wooded Exterior features

Welcome to Chesapeake, Virginia, a charming city where suburban tranquility meets vibrant community life. Nestled in the heart of the Tidewater region, Chesapeake is known for its lush landscapes, rich history, and a variety of recreational activities that cater to residents of all ages. With its convenient access to major highways, Chesapeake offers a perfect blend of rural charm and urban convenience, making it an ideal place to call home.

One of the standout features of homes in Chesapeake is their stunning wooded exteriors. Imagine coming home to a residence that seamlessly blends with nature, where the gentle rustle of leaves and the chirping of birds create a serene backdrop for your daily life. These homes, often nestled among mature trees and beautifully landscaped yards, provide not just aesthetic appeal but also a sense of privacy and tranquility. The wooded surroundings invite outdoor activities, from peaceful morning strolls to weekend barbecues with friends and family.

Chesapeake’s real estate market offers a diverse range of homes, many of which feature these enchanting wooded exteriors. Whether you’re looking for a cozy single-family home or a spacious property with room to grow, you’ll find options that suit your lifestyle and budget. The community is known for its excellent schools, parks, and recreational facilities, making it a perfect place for families, retirees, and everyone in between.

Discover the beauty of Chesapeake, VA, and explore homes that promise not just a place to live, but a lifestyle enriched by nature and community. Embrace the charm of wooded exteriors and find your dream home in this delightful city!

Newest Chesapeake Homes with Wooded Exterior features

$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, Chesapeake

$574,900

4 Beds ⋅ 2.1 Baths ⋅ 10647633 MLS

Welcome home to your brand-new waterfront retreat! This stunning new construction home offers 2,235 square feet of beautifully designed living space, featuring 4 bedrooms and 2.5 baths, with NO HOA! Perfectly situated on a canal/river, this property is an absolute dream for water enthusiasts. Launch your kayak, paddleboard, or small craft right from your own backyard, or take advantage of the ultra-convenient public boat launch located just next door! Inside, enjoy all the modern luxuries and pristine finishes that only new construction can offer, with an open floor plan designed for effortless entertaining and everyday living. If you have been dreaming of a turnkey waterfront lifestyle where every day feels like a vacation, your search ends here!

2800 Meadow Wood Drive E, Chesapeake

$285,000

3 Beds ⋅ 1.1 Baths ⋅ 10647127 MLS

Super convenient Chesapeake & Greenbrier location. Three bedrooms 1.5 baths plus a separate dressing area in master bedroom includes a 3rd sink. Spacious kitchen with nice counter space, all appliances, and a big front bay window. Schedule an easy showing today. 2-private parking spaces and a cul-de-sac location with no through traffic. BRAND NEW COSTCO is coming to Greenbrier Mall. Easy commute all military bases & downtown Norfolk shipyards. Easy access to beachfront and Greenbrier restaurants, shopping, NFCU & banks. YMCA includes swimming pool and activities. Buyer has ability to pick replacement carpeting. HOA approves - backyard fencing can be painted by seller. Newer heat pump unit for heating and cooling with Coolant 410A. HVAC under yearly inspection program. Seller provides Termite/Moisture clearance via Hampton Roads Warranty Program. No flood insurance required. Trash & Recycle cans provided.

1218 Cedar Mill Square, Chesapeake

$525,000

5 Beds ⋅ 3 Baths ⋅ 10646864 MLS

Charming & lovingly updated farmhouse in heart of Deep Creek on 1.2 acres includes all modern conveniences while respecting historic heritage w/features like original hardwood floors, crown molding, chair railing w/both welcoming front porch & screen porch. Beautiful kitchen w/SS appliances, granite counters, peninsula w/gas range, prep sink, SS wine fridge, oversized breakfast bar & pendent lighting. Bright & airy upstairs w/3 beds 2 w/walk-in closets, linen closet & updated hall bath w/beaded board wainscoting. 4th bed downstairs w/ensuite bath. Fantastic laundry room w/cabinetry, counter space, shelving & utility sink. Updates include: newer HVAC, ductwork & insulation, hardy plank siding & vinyl replacement windows. Spacious backyard 2 sheds & irrigation. Detached garage boasts almost 1500 sq feet split between the 2 levels. Upstairs living area has a full bedroom, bathroom and bonus closet/storage area. Great for your guests!

3248 Galberry Road, Chesapeake

$535,000

5 Beds ⋅ 2.1 Baths ⋅ 10647023 MLS

Beautiful 5-bedroom brick colonial in sought-after Brittany Woods, perfectly situated on a quiet cul-de-sac. This well maintained one owner home features a granite kitchen with island, eat in area, and stainless steel appliances, plus a bright year round sunroom and cozy office/loft. Updated baths include Corian countertops, and the primary bath offers duals sinks and is enhanced with a ceiling heater for added comfort on cold winter nights. Laundry room with W/D. The primary bedroom also boasts a large walk-in closet. A spacious family room has a natural gas fireplace and built-ins with gleaming hardwood floors in the living room, dining room, and foyer. Major updates include a 2021 gas furnace with 5 ton 17 SEER AC and new ductwork, 2025 exterior paint, 2023 refrigerator, newer Pella windows, and LeafGuard® gutters. Large backyard ideal for entertaining. Convenient to shopping, fine dining, medical facilities, shipyards, Portsmouth Naval Hospital, and interstates. A must-see home!

3017 Lord Bradford Court, Chesapeake

$235,000

2 Beds ⋅ 2 Baths ⋅ 10646952 MLS

Beautifully maintained 2 bedroom, 2 bath 1st floor condo is tucked away in Riverwalk, overlooking a peaceful wooded view. The updated kitchen features granite countertops, white cabinetry and stainless steel appliances, and opens seamlessly to the dining and living areas. Laminate flooring extends throughout the living room, dining area and hallway with carpet in both bedrooms. The spacious primary suite offers an updated en-suite bath with a dual vanity and walk-in shower. Relax on your private patio overlooking the trees...a serene setting to start and end your day. Enjoy low-maintenance living with the condo fee covering the roof, siding, water, sewer, trash pickup, landscaping and community pool. Conveniently located just minutes from interstates, shopping, restaurants, bases and River Crest Community Center.

716 Rapidan River Court Unit H, Chesapeake

$609,000

5 Beds ⋅ 3 Baths ⋅ 10646979 MLS

Tired of expensive water and sewer bills, HOA restrictions, or dealing with the stress and cost of a fixer upper? Then this brand new home is exactly what you have been waiting for. Welcome to this stunning 2,600 sq. ft. open concept residence built by local award winning builder. Featuring 5 spacious bedrooms, including a first floor bedroom great for guests or multi generational living, and 3 full baths with upscale designer finishes throughout. Enjoy luxury features including granite countertops, ceramic tile, luxury vinyl plank flooring, a cozy fireplace, and a beautiful standalone soaking tub. With NO HOA, this property is superb for boat owners, campers, trailers, or anyone wanting freedom and flexibility without extra fees or restrictions. Located in a highly sought school district with flexible spaces wonderful for entertaining and everyday living. Everything is brand new, offering peace of mind and low maintenance living.

789 Caddie Street, Chesapeake

$825,000

5 Beds ⋅ 2.1 Baths ⋅ 10646792 MLS

Space to gather, land to enjoy, and a separate apartment for the people who matter most. Nearly 3,900 square feet in the main home, 3 private acres, a detached three-car garage, and an approximately 1,000-square-foot apartment above it. This sprawling ranch offers four first-floor bedrooms, including the spacious primary suite with dual closets, beautifully refinished hardwoods, fresh paint, updated lighting, newer roof, new carpet and an expansive kitchen with gas cooking and newer appliances. A finished bonus room upstairs serves as the fifth bedroom or flexible space for guests, hobbies, or a quiet retreat. An enormous walk-in attic provides rare expansion potential, with room to add finished living space for an even more complete upstairs retreat. Enjoy the new Trex deck and peaceful backyard with room to entertain, garden, play, and bring your horses-picture them grazing outside your kitchen window while your coffee brews. Dreaming of an inground pool and backyard oasis? There is room for that too. Need space for your in-laws? Above the detached garage, the separately metered apartment includes its own bedroom, full bath, kitchen, living area, and laundry, creating true independent space for extended family, guests, a studio, or private home office. The apartment is not counted in sq ft/bedroom/bath count in this listing. Well and septic mean no monthly city water or sewer bill. Located in Riverwood, a quiet acreage community known for spacious homesites, mature trees, room for horses, and a neighborhood boat launch for enjoying nearby waterways. Enjoy the space and privacy of South Chesapeake in the Grassfield school district. Come see the lifestyle you have been searching for.

3700 Riverwood Crescent, Chesapeake

$665,000

4 Beds ⋅ 3 Baths ⋅ 10646600 MLS

LUXURY COASTAL RESORT STYLE RIVER FRONT COMMUNITY! Welden Field & Rowe Custom Home on a Premium .44-acre lot backs to Nature Preserve. Resort like lifestyle w/ waterfront Gazebo, deep water access, Kayak launch, Clubhouse, Pool, Fitness Room, Green Space, Nature Preserve w/Trails. Welcome to this meticulously maintained Craftsman-style home w/ Southern Living front porch & thoughtfully designed luxurious light-filled floor plan. Chef's kitchen w/ expansive island, bar seating, Dual-Fuel Range, tile back splash tile backsplash & Cafe SS appliances. Comfortable open living spaces that flow seamlessly throughout w/fireplace, 8 ft doors, high ceilings. Spacious downstairs owner's suite w/ Spa concept bathroom, tile floors, glass shower, over-sized Garden tub + custom walk-in closet + FF guest bedroom/Home Office w/ add storage. Outdoor oasis that backs to Nature Preserves w/ spacious covered porch, irrigation system, back up generation & MORE! Easy access to I-64, Edinburgh. WELCOME HOME!

409 Tranquility Trace, Chesapeake

$520,000

4 Beds ⋅ 3.1 Baths ⋅ 10646463 MLS

If you’ve been searching for true peace and privacy without sacrificing convenience, this Grassfield gem is an absolute must-see. Set back from the street on a private driveway, the property opens up to nearly an acre of total solitude, completely enveloped by woods and lush mature greenery. Inside, fresh paint brings a bright, inviting energy to a floor plan built for real life. The layout is a rare find for multi-generational living, featuring two distinct main-level suites. The in-law wing includes its own living room, making it easy to use as a private apartment, a 5th bedroom, or a home office. The primary suite feels like a custom getaway with live-edge wood countertops, dual shower heads, and a custom walk-in closet system. Out back, the property turns into a full outdoor retreat featuring a storage shed, a chicken coop, separate hookups ready for a pool and hot tub, and a massive detached two-car workshop/garage complete with a carport and RV hookup. Welcome home!

891 Bells Mill Road, Chesapeake

$435,000

3 Beds ⋅ 2.1 Baths ⋅ 10646107 MLS

The Welcome to your next home, where every day feels a little more special. Nestled in the highly sought-after Bryan's Cove community, this beautiful home offers more than just a place to live—it offers a lifestyle defined by comfort, convenience, and connection. Enjoy added privacy with a peaceful wooded backdrop and no rear neighbors. With a low condo fee, no flood insurance requirement, and zoning for the highly desirable Grassfield school district, this home truly checks all the boxes. Bryan's Cove is known for its scenic surroundings and exceptional amenities, offering the perfect blend of tranquility and everyday convenience. Residents enjoy access to a community dock, dog park, fitness center, clubhouse, and swimming pool. Nearby, you will find Publix, lots of other shopping and several restaurants, Tidewater Community College, and quick access to Interstates 64 and 264 makes commuting and daily errands effortless, while parks, recreation, and local attractions are all close by. Inside, you'll find a warm and inviting floor plan designed for both comfortable living and effortless entertaining. The spacious kitchen serves as the heart of the home, featuring a large center island with seating, abundant prep space, and a gas range that will delight home chefs. Every room has been thoughtfully designed to create a welcoming atmosphere where family and friends can gather and lasting memories can be made. Opportunities like this don't come along often. If you've been searching for a home in an exceptional community with outstanding amenities, top-rated schools, and a private, natural setting, this is one you won't want to miss. Schedule your private showing today and experience everything this remarkable home has to offer.

1741 Fortune Terrace, Chesapeake

$700,000

5 Beds ⋅ 2.1 Baths ⋅ 10645293 MLS

Tucked away on a quiet cul-de-sac, this beautifully maintained custom home offers the perfect combination of quality construction, thoughtful upgrades, and everyday comfort. Built in 2004 and offering approximately 3,300 square feet, this all-brick home features 5 bedrooms, with 4 conveniently located on the first floor, providing exceptional flexibility for families, guests, or multi-generational living. From the moment you step inside, you'll appreciate the soaring cathedral ceilings, spacious living areas, and inviting gas fireplace that create a warm and welcoming atmosphere. The private primary suite offers a relaxing retreat with a jetted soaking tub and generous walk-in closets. One of this home's standout features is the incredible backyard privacy. Whether you're enjoying your morning coffee, hosting family and friends on the large deck, or simply unwinding after a long day, you'll love the peaceful setting and the feeling of having your own private oasis. This home also offers valuable upgrades that provide peace of mind for years to come. A whole-house generator ensures you're prepared and comfortable during unexpected power outages and reflects the care and attention given to maintaining the home. An irrigation system keeps the lawn looking its best with minimal effort. Located in the highly sought-after Hickory school district, this home delivers the rare combination of timeless all-brick construction, flexible living space, exceptional privacy, and important long-term investments that today's buyers appreciate. If you've been searching for a home that is as practical as it is beautiful, this one is not to be missed. Some photos have been virtually staged.

1104 Arabian Arch, Chesapeake

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