West Chesapeake Real Estate

Welcome to West Chesapeake, Virginia, a vibrant community nestled within the charming city of Chesapeake. Known for its rich history, beautiful landscapes, and a welcoming atmosphere, West Chesapeake offers a unique blend of suburban tranquility and urban convenience, making it a perfect place to call home.

West Chesapeake is characterized by its picturesque neighborhoods, where tree-lined streets and well-kept parks create a serene environment ideal for families and individuals alike. The area boasts a variety of housing options, from cozy single-family homes to modern townhouses, catering to diverse lifestyles and budgets. Residents enjoy the convenience of local amenities, including shopping centers, restaurants, and recreational facilities, all within easy reach.

The city of Chesapeake is renowned for its commitment to education, featuring highly-rated schools that provide excellent opportunities for students. Additionally, the area is rich in outdoor activities, with numerous parks, trails, and waterways that invite residents to explore and enjoy the natural beauty of Virginia. Whether you’re kayaking on the Elizabeth River or hiking through the scenic Great Dismal Swamp, there’s no shortage of adventure waiting for you.

Culturally, West Chesapeake is vibrant, hosting various community events and festivals throughout the year that foster a strong sense of belonging and camaraderie among residents. With its blend of history, nature, and community spirit, West Chesapeake is not just a place to live; it’s a place to thrive. Discover the charm of West Chesapeake, where your dream home awaits amidst a backdrop of Southern hospitality and endless opportunities.

Newest Listings in 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

$169,900

2 Beds ⋅ 2 Baths ⋅ 10645374 MLS

Beautifully renovated in 2024, this move-in ready 2-bedroom, 2-bath condo offers modern updates and low-maintenance living in the heart of Western Branch. The spacious kitchen features granite countertops, a breakfast bar, and ample cabinet space. Enjoy newer luxury vinyl plank flooring throughout, fresh interior paint (2024), and the convenience of a newer washer and dryer, all of which convey. The bright, open floor plan provides comfortable living and dining areas, while the primary suite includes a private bath and generous closet space. Additional updates include a 2017 HVAC system and a 2023 water heater for added efficiency and peace of mind. Relax in this quiet, well-maintained community with a private storage shed and reserved parking. Conveniently located near shopping, dining, interstates, military bases, and more—this beautifully updated condo is ready for you to call home!

3327 Clover Meadows Drive, West Chesapeake

$165,000

2 Beds ⋅ 1 Baths ⋅ 10645273 MLS

Welcome home to this charming first-floor condo in the desirable Clover Meadows community of Western Branch! Offering 2 bedrooms and 1 full bath, this well-maintained condo features an open and functional layout with abundant natural light and added privacy as an end unit. Enjoy easy one-level living with a spacious living area, cozy dining space, and a bright kitchen with ample cabinet storage. Conveniently located near shopping, dining, interstates, and military bases, this home is perfect for commuters. Assigned parking and low-maintenance living make this listing a must-see!

3337 Clover Meadows Drive, West Chesapeake

$9,900

10645258 MLS

Lot 100 Farmington Acres, approximately 0.36ac. Lot is located at 3509 Sigmon Dr. which is a paper street. 150' in from where Newport Dr. currently stops then turn right onto Sigmon Dr. heading back North approximately 300'. A gorgeous lot, will require improvements including but not limited to: wetlands delineation, and improvement of Newport Dr. and Sigmon Dr. to city standards before construction, lot is priced accordingly.Fantastic opportunity for sweat equity, or buy and hold as part of diversifying your investments or long term retirement. The property is minutes away from the booming North Suffolk area. Neighborhood also borders the north side of the gorgeous Retreat at Western Branch Subdivision as well as the Dunedin neighborhood.Don't miss the chance to scoop up your piece of Western Branch now at a discount!Please be mindful of neighbors when parking on Newport Dr. to view. Call listing agent with any questions!

3509 Sigmon Drive, West Chesapeake

$165,000

2 Beds ⋅ 1 Baths ⋅ 10645120 MLS

3524 Clover Meadows Drive, 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.