West Chesapeake Real Estate

Welcome to West Chesapeake, Virginia—a vibrant community nestled within the heart of Chesapeake County. Known for its charming neighborhoods, lush landscapes, and a strong sense of community, West Chesapeake offers a unique blend of suburban tranquility and urban convenience, making it an ideal place to call home.

As you explore West Chesapeake, you'll be captivated by its tree-lined streets and beautifully maintained parks. The area is rich in outdoor recreational opportunities, with numerous walking trails, playgrounds, and picnic spots that invite families and nature lovers alike to enjoy the great outdoors. The nearby Chesapeake City Park and the Elizabeth River provide ample opportunities for fishing, kayaking, and leisurely strolls along the waterfront.

West Chesapeake is also a hub of cultural diversity, boasting a variety of local restaurants, shops, and entertainment options. From cozy cafes to family-owned eateries, there’s something to satisfy every palate. The community hosts several annual events and festivals that celebrate its rich heritage, fostering a strong sense of belonging among residents.

Education is a top priority in West Chesapeake, with access to highly-rated schools and educational programs that cater to students of all ages. Families will appreciate the community’s commitment to providing a safe and nurturing environment for their children.

With its perfect blend of convenience, community spirit, and natural beauty, West Chesapeake, VA, is not just a place to live—it's a place to thrive. Whether you’re looking to buy your first home or seeking a peaceful retreat, West Chesapeake invites you to discover all it has to offer. Come and experience the charm of this wonderful city!

Newest Listings in West Chesapeake

$565,000

5 Beds ⋅ 2.1 Baths ⋅ 10646268 MLS

Welcome to this charming 5-bedroom home, perfectly situated in a wonderful, established neighborhood in Chesapeake. If you appreciate a home with character and room to grow, this is the perfect canvas for your vision. The heart of the home features a kitchen designed for those who love to cook, offering an abundance of counter and cabinet space, plus the convenience of a double oven. You’ll love spending quiet evenings by one of the two cozy fireplaces or unwinding on the beautiful, screened-in porch that overlooks a private, tree-lined backyard. With spacious bedrooms throughout, this home offers plenty of room for everyone to enjoy. Bring your personal touch and make this well-loved house your own!

2949 Prince Of Wales Drive, West Chesapeake

$560,000

5 Beds ⋅ 2.1 Baths ⋅ 10646195 MLS

Spacious Home In Wellington! This Beautiful Home Features A Fantastic Open Downstairs Floor Plan That's Perfect For Both Everyday Living And Entertaining. Spacious Primary Suite Downstairs With A Double Vanity & Soaking Bath~Upstairs, You'll Find Four Additional Bedrooms. Enjoy Large Closets, Formal Living And Dining Room With Brazilian Wood Floors And A Family Room Just Off A Great Kitchen Which Has A Lots Of Cabinet Space & Island For The Cook In The Family! Living Room Has A Cozy Gas Fireplace. Covered Deck With Dual Fans Making Outdoor Entertaining Great In The Summer Time ! Large Fenced In Back Yard. Conveniently Located Near Shopping, Dining, Military Bases, And Major Highways! This Home Is A Must See !!

3635 Mardean Drive, West Chesapeake

$162,000

2 Beds ⋅ 2 Baths ⋅ 10646186 MLS

Welcome home to this move-in ready, two bedroom, two bathroom condo located in the heart of Western Branch! Whether you are looking for your first home, or looking to downsize, you will enjoy low maintenance living in this first floor unit that is conveniently accessible to Harbor View, Interstate 664, Interstate 64, shopping, dining, entertainment, and military bases! With beautifully placed new LVP flooring throughout the home, and an updated primary bathroom, you'll live without stress knowing your HVAC system and hot water heater are both less than two years old, have reserved parking, and a private storage shed! Schedule your showing today, and make this home yours before it's gone!

3504 Clover Meadows Drive, West Chesapeake

$440,900

3 Beds ⋅ 3.1 Baths ⋅ 10646167 MLS

Welcome to Breck Grove, an exquisite townhome community in Western Branch, Chesapeake, where fine finishes & quality construction meet modern living. This tri-level END UNIT Ashbury plan beautifully showcases an open floorplan w/ luxurious upgrades & a single car garage. The kitchen stuns guests w/ granite countertops, subway tile backsplash, crown molding & soft-close drawers. Easily maintained & durable LVP & vinyl flooring throughout. Lighted tray ceiling in primary suite & WIC. Double granite vanity & 5' shower in en-suite. Enjoy exceptional amenities, including a start-of-the-art clubhouse & sparkling pool, great for relaxation & socializing. Discover your new home today! Call agent to schedule an appointment.

2013 Guava Lane, West Chesapeake

$370,000

3 Beds ⋅ 2.2 Baths ⋅ 10645727 MLS

Welcome to this well-maintained, like-new townhome in the desirable Fairview Towns community! Enjoy low-maintenance living in this newer gated community, conveniently located in Western Branch. This spacious tri-level townhome features 3 bedrooms, 2 full bathrooms, and 2 half bathrooms, along with two family rooms providing plenty of space for entertaining, relaxing, or creating a home office or flex space. The home also offers a one-car garage, two additional assigned parking spaces, and ample visitor parking. Come experience all this beautiful townhome has to offer and make it yours today!

4122 Riverside Drive, West Chesapeake

$535,000

4 Beds ⋅ 2 Baths ⋅ 10644832 MLS

Welcome home to this beautifully updated ranch in the desirable Crossings neighborhood of Western Branch! This move-in-ready home offers 4 bedrooms and 2 full baths, including a spacious first-floor primary suite with a renovated en-suite bath. The oversized FROG serves as a 4th bedroom, home office, gym, or media room. Freshly painted throughout, the home features soaring ceilings, an open foyer, formal living and dining rooms, new flooring, stylish fixtures, and a cozy gas fireplace. The updated kitchen boasts modern cabinetry, upgraded countertops, a breakfast area, coffee nook, and updated stainless steel appliances/gas range (2025). Relax in the fully fenced backyard featuring a deck, gazebo, rock garden, and peaceful sitting areas. Attached 2-car garage PLUS a detached 2-car garage/workshop. Schedule your private tour today! * Select photos have been virtually staged to show potential furniture layouts.

2927 Crossings Drive, West Chesapeake

$170,000

2 Beds ⋅ 2 Baths ⋅ 10645597 MLS

MOVE IN READY AND LOW MAINTENANCE LIVING! Whether you’re searching for your first home, looking to downsize, or add to your investment portfolio, this beautifully updated first floor end unit checks all the boxes. Featuring luxury vinyl plank flooring, fresh interior paint, stainless steel appliances, and updated bathrooms, this home is truly move in ready. Ideally located in Western Branch with convenient access to Interstate 664, Interstate 64, Harbor View, Greenbrier, shopping, dining, entertainment, and major military installations throughout Hampton Roads, you’ll love the convenience this location has to offer. Turnkey opportunities like this do not come around often. Schedule your private showing today before it’s gone.

3500 Clover Meadows Drive, West Chesapeake

$551,900

4 Beds ⋅ 2 Baths ⋅ 10645495 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, a 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 doorstep in an exciting new homes community! Builder is offering 3% CCA (See listing agent for details, as restrictions may apply) when using one of our preferred lenders. Model home open daily 12-5 pm at 5023 Annapolis Drive.

2207 Hampton Roads Parkway, West Chesapeake

$578,645

4 Beds ⋅ 2.1 Baths ⋅ 10645480 MLS

Home is 100% complete. 30 Day close is available. This traditional floor plan that offers 4 Bedrooms, 2.5 Baths, and 2400+ sq ft. Enjoy the grand design of the Primary Suite with a spacious Walk-In Closet from the Primary Bath. The dining room, kitchen & family room on the first floor allow for many entertaining evenings at home. The open floor plan provides ample space with room to stretch out. 2nd floor is spacious with 4 bedrooms & a utility room. The Estates at Jolliff Landing will be a charming neighborhood boasting single-family homes with covered porches, lush gathering spaces, an assortment of yard games, a playground, water features, a sports field, bike paths, a community center, a swimming pool, and tree-lined sidewalks. The builder is offering 4% CCA (see listing agent for details) when using one of our preferred lenders. Model home open daily 12-5pm at 5023 Annapolis Drive.

5112 Annapolis Drive, West Chesapeake

$609,000

4 Beds ⋅ 2.1 Baths ⋅ 10645393 MLS

Premium location in one of Western Branch’s most sought-after neighborhoods & schools. Beautiful, manicured homes w/large lots & no homeowner’s association. Just minutes to 664 & ALL of Hampton Roads Military bases, shopping & entertainment and medical facilities. Step inside to a welcoming foyer that leads to a formal dining room, living room and a custom kitchen with an Island. The sunken den features a gas fireplace which exits to a multi-level deck for cookouts and entertaining. The upstairs features a primary suite for a private retreat with an en-suite bath, a large walk-in closet for keeping all your items organized, while two additional bedrooms (all with walk-in closets) provide versatility for guests or even a game (flex) room. In addition, a 4th bedroom is located over the 576 SQFT. Attached garage. New interior paint and carpet, move in ready

1416 Pine Grove Lane, West Chesapeake

$584,900

5 Beds ⋅ 2.1 Baths ⋅ 10645337 MLS

A versatile floor plan with ample space for entertaining! Tha Palm offers 5 Bedrooms , 2.5 Baths, a large Family room, open to the kitchen, all BR's on 2nd floor, large patio space for outdoor living. A desirable Primary Suite bath & walk-in closet.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, a 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 doorstep 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 pm at 5023 Annapolis Drive.

2202 Wilmington Avenue, West Chesapeake

$315,000

3 Beds ⋅ 1.1 Baths ⋅ 10645375 MLS

This well-maintained home offers peace of mind with numerous updates completed over the years. According to the seller, replacement windows were installed in 2006, followed by a new HVAC system and roof in approximately 2009. The home also features a newer washer and dryer (2016), stove (2020), water heater (2021), and refrigerator (2024). Most recently, the kitchen was refreshed in 2025 with beautiful new cabinets and countertops, creating a bright, modern space that's perfect for everyday living and entertaining. With so many major improvements already completed, this home is ready for its next owner to move in and enjoy.

4213 Valencia Road, 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.