Chesapeake VA Homes with Wooded Exterior features

Welcome to Chesapeake, Virginia, a hidden gem nestled in the heart of the Tidewater region. This vibrant city is known for its rich history, stunning landscapes, and a community spirit that welcomes everyone with open arms. With over 22 miles of scenic waterways, Chesapeake offers a harmonious blend of urban convenience and natural beauty, making it an ideal place for families, retirees, and anyone looking to embrace a relaxed lifestyle.

One of the standout features of homes in Chesapeake is their enchanting wooded exteriors. Imagine coming home to a property enveloped in the tranquility of nature, where towering trees and lush greenery provide a serene backdrop. These homes not only offer aesthetic charm but also provide a sense of privacy and peace that is hard to find in more urban settings. The wooded exteriors create a perfect canvas for outdoor living, whether it's hosting summer barbecues on your deck or enjoying quiet evenings by a fire pit surrounded by the beauty of nature.

Chesapeake is also known for its excellent schools, diverse recreational opportunities, and a thriving economy, making it a fantastic place to settle down. With easy access to major highways, you can enjoy the best of both worlds—peaceful suburban living and the vibrant culture of nearby Norfolk and Virginia Beach.

Whether you’re seeking a cozy retreat or a spacious family home, Chesapeake's homes with wooded exteriors promise a lifestyle that embraces nature while providing all the comforts of modern living. Come discover your dream home in this enchanting city!

Newest Chesapeake VA Homes with Wooded Exterior features

$950,000

5 Beds ⋅ 3 Baths ⋅ 10648261 MLS

Welcome to your private 3.25-acre country oasis, where luxury finishes, heavy-duty infrastructure, and absolute peace of mind converge. This beautifully updated single-story home offers an open-concept layout and highly functional spaces, making it a rare market find. INTERIOR HIGHLIGHTS Step inside to a bright, airy open floor plan where the living and dining areas flow seamlessly into the chef-inspired kitchen. The kitchen is outfitted with premium Cambria countertops for unmatched durability and sleek modern style. The primary suite serves as a spa-like retreat, boasting natural quartzite surfaces, a deep jetted soaking tub, and a massive 4x4 walk-in shower. Upstairs, a versatile finished room over the garage (FROG) and a charming attic dormer offer excellent bonus spaces for a home office, media room, gym, or guest quarters. OUTDOOR LIVING & ENTERTAINING Embrace the scenic acreage from your choice of outdoor living areas. Relax on the welcoming covered front porch, or host unforgettable gatherings on the expansive rear covered patio. The outdoor living experience is anchored by a fully equipped outdoor kitchen, great for weekend barbecues and dining al fresco while overlooking your sprawling, private acreage. THE ULTIMATE DETACHED WORKSHOP A true standout feature is the massive 2,200 sq. ft. detached workshop. This incredible building is fully powered and completely climate-controlled with heating and cooling, making it an ideal setup for a home business, car enthusiast, hobbyist, or extensive machinery storage. PREMIUM SYSTEMS & INFRASTRUCTURE No expense was spared on the home's mechanics and structural integrity: * Power Security: Whole-home generator supported by a recently added 500-gallon propane tank. * Efficiency: All-new energy-efficient windows and updated insulation throughout. * Roof & Plumbing: Roof is approx. 4 years young. All plumbing has been fully updated with zero cast iron. * Utilities: Tankless water heater for endless hot water; septic system recently serviced. Welcome Home.

1908 Benefit Road, South Chesapeake

$300,000

2 Beds ⋅ 1 Baths ⋅ 10647978 MLS

Investors! 2 Parcels totalling 22.25 +/- acres currently zoned M1 for large tract (17.5acres) and residential small tract (4.75 acres) This piece of land must be purchased with 1828 Mount Pleasant Road which is right nextdoor and runs parallel to property and has a small house with power, septic and well. Subject to zoning, interested parties should contact the City of Chesapeake Zoning and Planning for allowable uses.

1832 Mount Pleasant Road, South 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

$455,000

3 Beds ⋅ 2.1 Baths ⋅ 10647905 MLS

Built in 2021, this beautifully designed townhouse-style condo offers 2,234 square feet of thoughtfully designed living space, featuring an open floor plan and a desirable first-floor primary suite. The spacious great room with soaring ceilings flows seamlessly into the kitchen, complete with granite countertops, stainless steel appliances, a pantry, peninsula seating, and an adjoining dining area. The primary suite features a generous walk-in closet and an en-suite bath with a double vanity and oversized shower. Upstairs, you'll find two spacious bedrooms, a full bath, a loft overlooking the great room, and an unfinished storage room for abundant storage. Additional highlights include a two-car attached garage, large laundry room, and tankless water heater. A private rear patio provides the perfect spot to relax and unwind. Enjoy low-maintenance living with resort-style amenities including a clubhouse, pool, dock, playgrounds, private beach, and ground maintenance, all within the highly sought-after Grassfield school district.

1758 Barkadeer Cove, South 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

$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

$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, West Chesapeake

$825,000

4 Beds ⋅ 4 Baths ⋅ 10647485 MLS

Welcome to this custom-built retreat situated on 5 acres in a highly desirable Grassfield school district. Thoughtfully designed this exceptional property offers generous indoor and outdoor space with features ideal for multigenerational living, entertaining, hobbies, and storage. The private in-law suite includes a kitchenette and its own screened porch, creating a welcoming space for guests or extended family. Upstairs, you’ll find two ensuite bedrooms, along with an additional bedroom that offers excellent potential as a theater room, home office, or flexible living space. Car enthusiasts, hobbyists, and those seeking extra workspace will appreciate the two-car attached garage, one-car detached garage with work area, and two storage sheds. From the inviting front porch—perfect for quiet mornings and scenic views—to the rear deck designed for gathering with family and friends, this one-of-a-kind property offers the space, privacy, and versatility today’s buyers are looking for.

1837 Benefit Road, South Chesapeake

$650,000

5 Beds ⋅ 3.1 Baths ⋅ 10647348 MLS

Welcome to this spacious 3 story home offering 5 bedrooms, 3.5 bathrooms, and a versatile flex space adjacent to the fifth bedroom on the third floor, ideal for a home office, media room, hobby space, or additional living area. Brand new carpet has been installed throughout, creating a fresh and inviting feel. The backyard is designed for relaxation and entertaining with an inground fiberglass pool, white vinyl privacy fence, and a wooded buffer behind the property for added privacy. Additional features include an EV charging station, Cat 5 wiring throughout the home, and solar panels that help offset electricity costs. Conveniently located near shopping, dining, parks, and major commuter routes, this home is zoned for the Grassfield school district and offers flexible living spaces with modern amenities ready for its next owner.

2237 Summer Breeze Road, South Chesapeake

$400,000

5 Beds ⋅ 2 Baths ⋅ 10647174 MLS

Welcome to this desirable large brick Ranch located in beautiful Georgetown Colony. Inside, you'll find neutral paint throughout, carpet replaced just 2 years ago, and beautifully updated bathrooms, leaving just enough opportunity for the new owner to add their own personal style. The spacious backyard backs to a peaceful stream and includes a small fenced dog run for your furry family members on almost a .5 acre lot. The brand-new refrigerator conveys, along with all other kitchen appliances replaced within the last 3 years. Washer and dryer convey as-is. his home has been lovingly updated and shows pride of ownership. Conveniently located near shopping, dining, interstates, military bases, and everything Chesapeake has to offer—this one is ready for its next owner!

2301 Georgetown Boulevard Boulevard, Central Chesapeake

$285,000

3 Beds ⋅ 1.1 Baths ⋅ 10647127 MLS

Super convenient Chesapeake/ Greenbrier location. Easy access, nice roads. Very nice neighborhoods, streets, parks & even lakes in area. Three bedrooms 1.5 baths plus a separate dressing area in master bedroom includes a 3rd sink & counter. Nice kitchen with counter space, all appliances, and a big front bay window. Buyer can pick carpet. 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. Newer hot wtr. Greenbrier Mall Area is amazing! HVAC under yearly inspection program. Seller provides Termite/Moisture clearance via Hampton Roads Warranty Program. No flood insurance required. Aviation noise is non existent, very peaceful.

1218 Cedar Mill Square, South Chesapeake

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