West Chesapeake Homes with Wooded Exterior features

Welcome to West Chesapeake, Virginia—a hidden gem nestled within the vibrant city of Chesapeake. Known for its picturesque landscapes and rich history, West Chesapeake offers a delightful blend of suburban charm and natural beauty. With its lush greenery, serene parks, and close-knit communities, this area is perfect for families, nature lovers, and anyone seeking a peaceful retreat from the hustle and bustle of city life.

One of the standout features of homes in West Chesapeake is their stunning wooded exteriors. Many properties boast beautiful wooded surroundings, creating a tranquil atmosphere that invites relaxation and outdoor exploration. Imagine waking up to the gentle rustle of leaves and the soothing sounds of nature right outside your window. These homes not only provide a comfortable living space but also serve as a gateway to the great outdoors, perfect for hiking, biking, or simply enjoying a leisurely stroll through the trees.

The architecture of these homes often reflects the natural beauty of their surroundings, with designs that harmonize with the landscape. Whether you’re looking for a cozy single-family home or a spacious property with room to grow, West Chesapeake offers a variety of options that cater to different lifestyles and preferences.

In addition to its stunning homes, West Chesapeake is conveniently located near top-rated schools, shopping centers, and recreational facilities, making it an ideal place to call home. Explore the charm of West Chesapeake and discover the perfect blend of comfort, community, and the beauty of nature—all waiting for you in this enchanting part of Virginia.

Newest West Chesapeake Homes with Wooded Exterior features

$524,900

4 Beds ⋅ 3.1 Baths ⋅ 10650967 MLS

Situated on nearly half an acre of lush lawn and beautifully landscaped grounds, this immaculately maintained home offers comfort, flexibility, and space for everyone. Gorgeous wood floors and a custom wood-burning fireplace add warmth, while the screened porch overlooks the saltwater pool and fully fenced backyard. The spacious kitchen features granite, stainless steel appliances, and abundant cabinet and counter space. A downstairs bedroom and full bath, plus a half bath, make this home ideal for guests or multi-generational living. Upstairs, the large primary suite offers a sitting room and walk-in closet. The finished room over the garage, with two entrances, provides flexible space for a media room, game room, second living area, or private retreat, along with a spacious bedroom. Outside, enjoy a new patio and beautiful landscaping that create a true backyard oasis. With newer systems, an encapsulated crawl space, and meticulous owners, all that's left to do is move in!

2047 Ames Cir N Circle, West Chesapeake

$550,000

3 Beds ⋅ 2 Baths ⋅ 10649003 MLS

This is a project property.3 bedrooms 2 bathrooms. Septic and well water, no city hook ups. The property will be sold as is. Only to be purchased with 4733 Sondej Ave MLS#10648999 will not be sold separately. Lot lines not accurate in rein. 4745 and 4741 are one lot. Contact agent for details. Sits on 8.505 Acres

4745 Sondej Avenue, West Chesapeake

$575,000

4 Beds ⋅ 3.1 Baths ⋅ 10648135 MLS

Welcome to 2072 River Pearl Way in well-established Waterstone; two-story home featuring 2,800 sqft, 4 bdms, 3.5 baths, giving you room to grow, host, and settle in. A fireplace warms the main living area, while exotic wood, carpet, and ceramic tile carry through the floor plan. Upstairs, the spacious primary suite offers a peaceful retreat complete with a private en suite featuring heated tile floors for a touch of everyday luxury. Step outside to a deck featuring composite decking materials designed for longevity overlooking the backyard, made for morning coffee or evening gatherings, with a long driveway providing ample parking. Waterstone is known for its tree-lined streets and community pond, where residents can paddle a kayak, canoe, or paddleboard right in their own neighborhood. Book your showing now!

2072 River Pearl Way, West Chesapeake

$389,000

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 E, West Chesapeake

$520,000

4 Beds ⋅ 2.1 Baths ⋅ 10647434 MLS

Welcome to this beautifully maintained home in Jolliff 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

$574,900

4 Beds ⋅ 2.1 Baths ⋅ 10647633 MLS

Not finding the quiet and privacy you are looking for in a brand-new construction home? Want quiet luxury on a lot nestled in trees and neighbored by a quiet tributary instead of fences, driveways and alleys? Don’t want to have to pay for an HOA you won't benefit from? If so, then you have to see this brand-new home. 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 tributary of the Western Branch of the Elizabeth 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! Enjoy nature among the mature trees with plenty of lawn and space from your neighbors. 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

$519,900

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, West Chesapeake

$440,000

3 Beds ⋅ 1.1 Baths ⋅ 10644034 MLS

Escape to serene equestrian country living! This inviting 3-bedroom, 1.5-bath ranch (with additional non-heated/cooled bedroom/flex room over garage and additional full bath) sits on over 3 acres in Chesapeake's desirable Western Branch area, offering the perfect blend of privacy, open space, and modern updates. Inside, you'll find a move-in-ready home featuring a bright, updated kitchen, durable LVP flooring, spacious bedrooms, and the convenience of single-level living. The room over the attached garage provides flexible space for a home office, guest suite, 4th bedroom, or in-law suite. Outside, the 3-stall horse barn needs TLC, plus plenty of room for gardening, recreation, or creating your own mini homestead. Recent improvements include land improvements (2019), well service (2020), electrical panel service (2020), foundation improvements (2021), new appliances (2022). Tenant occupied at $2,800 per month thru 1/31/27. Live in or rent out.

4309 East Road, West Chesapeake

$609,900

6 Beds ⋅ 3 Baths ⋅ 10641027 MLS

A versatile floor plan built with space for EVERYONE! Our Myrtle model offers ranch style living with 6 bedrooms including a large finished room over the garage. Family Room opens to the Kitchen and Breakfast Area. The Estates at Jolliff Landing is a charming neighborhood boasting single family homes with covered porches, tree-lined sidewalks, lush gathering spaces, an assortment of yard games, community playground, water features, a sports field, bike paths, and a community clubhouse with a resort-style in-ground swimming pool. A plethora of outdoor activities right at your door step in an exciting new homes community! Builder is offering partial CCA & $15,000 buyer incentive (See listing agent for details as restrictions may apply) when using one of our preferred lenders. Model home open daily 12-5:00 pm at 5023 Annapolis Drive.

2223 Hampton Roads Parkway, West Chesapeake

$1,257,400

5 Beds ⋅ 4 Baths ⋅ 10640535 MLS

Proposed To Be Built- Waterfront Custom Home Community Located on the Western Branch of the Elizabeth River! Beautiful Creek Front Large Lot. Home Features Hardie Plank Exterior w/ Stone Accents. A Large Covered Rear Porch/ Dining Area w/ Stamped Concrete. Open Airy Floor Plan w/ Gourmet Kitchen, a Large Center Island, 36" Gas Cooktop, 9' Ceilings First and Second Floors. First Floor Features Eng. Hardwood. First Floor Primary Bedroom w/ Luxury Bath and Freestanding Tub. Additional first floor Study/Bed Room w/ Full Bath, Spacious second floor with Two Bedrooms, Two Baths ( One En-Suite, One Hall Bath). Large Bonus Room, Step-up Game/Recreation Room over the Family Room features a Second Floor Balcony with a Beautiful Creek View! Yard Fully Sodded and Irrigated. Many Special Features Included. Sasser has been a member of the Southern Living Custom Builder Program for 30+ years and awarded SL Custom Builder of the Year. * If Financing Buyer to obtain a Custom to Permanent Loan.

2832 Martins Point Way, West Chesapeake

$599,900

4 Beds ⋅ 2.1 Baths ⋅ 10613272 MLS

Start building your custom dream home today! Exceptional new construction opportunity on a spacious half-acre lot in the heart of Western Branch. Design your own floor plan to match your lifestyle or choose from one of the builder's stunning models. This featured plan offers a modern open-concept layout. The chef's kitchen features granite countertops, custom cabinetry, stainless steel appliances, and designer lighting. A formal dining room can easily serve as a home office. Enjoy luxury vinyl plank flooring throughout the first floor and baths, plus a covered front porch and rear patio for outdoor living. Experience quality craftsmanship, thoughtful design, and the freedom to create the home you've always imagined. Ready in Spring 2026. Contact us today to start designing your custom dream home!

1530 Jolliff Road, West Chesapeake

$539,900

4 Beds ⋅ 2 Baths ⋅ 10609828 MLS

A versatile floor plan built with space for EVERYONE! Our Myrtle model offers ranch style living with 4 bedrooms including a large finished room over the garage. From the front porch to the Family Room also open to the Kitchen and Breakfast Area. The Estates at Jolliff Landing is a charming neighborhood boasting single family homes with covered porches, tree-lined sidewalks, lush gathering spaces, an assortment of yard games, community playground, water features, a sports field, bike paths, and a community clubhouse with a resort-style in-ground swimming pool. A plethora of outdoor activities right at your door step in an exciting new homes community! Builder is offering partial CCA & $15,000 buyer incentive (See listing agent for details as restrictions may apply) when using one of our preferred lenders. Model home open daily 12-5pm at 5023 Annapolis Drive.

MM Myrtle, 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.