Chesapeake VA Homes with Jolliff Middle Middle school

Welcome to the charming community of West Chesapeake, Virginia, where the blend of suburban tranquility and vibrant local culture creates an ideal setting for families and individuals alike. Nestled in the heart of Chesapeake County, this area boasts a rich history and a welcoming atmosphere, making it one of the most sought-after locations in the Hampton Roads region.

West Chesapeake is known for its picturesque neighborhoods, where tree-lined streets and well-kept homes create a warm sense of community. Families will appreciate the proximity to Jolliff Middle School, a well-regarded institution that offers a nurturing environment for students to thrive academically and socially. With a strong emphasis on education, the area attracts families looking for quality schooling options, ensuring that children receive the best possible start in life.

The real estate market in West Chesapeake features a diverse range of homes, from charming single-family residences to modern townhouses, catering to various lifestyles and budgets. Many properties offer spacious yards, perfect for outdoor gatherings and playtime, while others boast contemporary finishes and amenities for those seeking a more modern lifestyle.

Beyond the homes, West Chesapeake is a treasure trove of recreational opportunities. Residents can enjoy nearby parks, walking trails, and community events that foster a sense of belonging. The area's convenient access to major highways makes commuting a breeze, while the vibrant shopping and dining options in Chesapeake and neighboring cities ensure that you’ll never run out of things to do.

Discover the warmth and charm of West Chesapeake, where your dream home awaits in a community that feels like family.

Newest Chesapeake VA Homes with Jolliff Middle Middle school

$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

$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

$315,000

3 Beds ⋅ 1 Baths ⋅ 10645059 MLS

This lovely 3 bedroom/1 bath abode is fresh, charming and a perfect fit for the whole family! Enjoy the benefits of solar panels that keep energy costs low. The spacious backyard is ideal for curious kids to explore, energetic pups to play fetch or a small-scale gardener’s dreams to come true. Gorgeous warm wooden cabinets , coffee bar, custom island , pantry and gas stove create a luxurious feel in this gourmet kitchen. Enjoy time in the open family room complete with striking wood flooring, a cozy and comfortable space for family movie nights and memory making, find a bonus room that offers endless possibilities creates a cozy playroom, a productive home office or transform it into an extra bedroom. Take comfort in the attractive brick exterior of the home as it’s sure to stay tidy and effortless to maintain for years to come. Check out this wonderful opportunity to live the good life in Chesapeake!

3944 Port Road Road, Central 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

$330,000

3 Beds ⋅ 1.1 Baths ⋅ 10645365 MLS

Welcome home to this well-maintained 3-bedroom, 1.5-bath brick ranch nestled on a quiet cul-de-sac in the desirable Deep Creek area of Chesapeake. This charming home offers 1,392 square feet of comfortable living space, including a spacious den/family room perfect for entertaining, relaxing, or creating the ideal flex space. Major updates completed approximately 7 years ago include the roof, HVAC, windows, water heater, and encapsulated crawlspace, providing added peace of mind. The attached garage offers additional storage and convenience, while the washer and dryer convey with the home. Being sold As-Is, with the seller willing to consider reasonable buyer concessions with an acceptable offer. Don't miss this wonderful opportunity to make this home your own!

1213 Lakeview Court, South Chesapeake

$348,900

2 Beds ⋅ 2.1 Baths ⋅ 10645065 MLS

Welcome to Piney Grove, an exquisite community in Western Branch, Chesapeake, where fine finishes & quality construction meet modern living. This 2-level plan beautifully showcases an open floorplan w/ luxurious upgrades. The kitchen stuns guests w/ upgraded quartz countertops, subway tile backsplash, & soft-close drawers. Easily maintained & durable LVP flooring & crown molding throughout 1st level. Lighted tray ceiling in primary bedroom. WIC's in both bedrooms. Quartz vanity in primary bath w/ glass-enclosed shower. Enjoy a partially wooded view & exceptional community amenities, including stet-of-the-art clubhouse & sparkling pool, great for relaxation & socializing. Discover your new home today! Call agent to schedule an appointment & to take advantage of pre-opening special pricing!

4981 Boone Road, West Chesapeake

$1,195,000

4 Beds ⋅ 4.1 Baths ⋅ 10644941 MLS

Dreaming of a Serene Country Retreat just minutes from the city? YOU FOUND IT! A Rare Jewel! Horse Lover's Dream! Almost 9 ac Family Sanctuary. Elegant Custom Built, 4 Ensuite BRs & 1/2 Bath home w/an amazing 10' x 50' front porch! Lovely entry foyer opens to Great Room w/cathedral ceiling, hand scraped engineered flooring & wood burning fireplace framed w/bookshelf cabinetry. 1st Floor Primary BR boasts expansive Bath w/2 Separate Granite Vanities, jetted tub, separate shower & Grand Walk-In Closet. PBR Plantation Shutters reveal peaceful views of property! 10 ft ceilings down & 9 ft up. Kitchen w/granite counters, 2 large pantries, ample cabinetry & generous eat-in area. Formal Dining Room for festive gatherings. Upstairs reveals open sitting area w/chandelier. Expansive FROG-4th Bedroom. 3 Covered porches. 3 Car Garage, Spacious 2 Stall Stable, Large Storage Barn, approx 30' x 20' IG Pool w/stamped concrete surround. Fruit trees & acreage for hobby farming. Don't miss this one!

377 Homestead Road, West Chesapeake

$345,900

2 Beds ⋅ 2.1 Baths ⋅ 10645033 MLS

Welcome to Piney Grove, an exquisite community in Western Branch, Chesapeake, where fine finishes & quality construction meet modern living. This 2-level plan beautifully showcases an open floorplan w/ luxurious upgrades. The kitchen stuns guests w/ upgraded quartz countertops, subway tile backsplash, & soft-close drawers. Easily maintained & durable LVP flooring & crown molding throughout 1st level. Lighted tray ceiling in primary bedroom. WIC's in both bedrooms. Quartz vanity in primary bath w/ 5' shower. Enjoy a wooded view & exceptional community amenities, including stet-of-the-art clubhouse & sparkling pool, great for relaxation & socializing. Discover your new home today! Call agent to schedule an appointment & to take advantage of pre-opening special pricing!

4983 Boone Road, West Chesapeake

$400,000

4 Beds ⋅ 2.1 Baths ⋅ 10644987 MLS

Welcome home to 4320 Schooner Trail! This beautifully maintained 4 -bedroom, 2.5 bathroom home in the sought- after Western Branch area of Chesapeake. This home offers an ideal blend of space, comfort, tons of storage and modern convenience. The downstairs features an open- concept floor plan seamlessly connecting the living room, dining area and kitchen area that has stainless steel appliances and a private office with French doors. Upstairs features a huge master bedroom with walk in closets and a massive attached bathroom. Enjoy the private, fully fenced in backyard that is perfect for relaxing and entertaining guests. The HVAC system was replaced in 2024 and the fireplace has never been used by the owner. The fireplace sold as-is. Call today for your private showing of your new home!

4320 Schooner Trail, West Chesapeake

$310,000

3 Beds ⋅ 2 Baths ⋅ 10644587 MLS

Instant equity!!!!Welcome home to this charming, single-level ranch that blends comfort and functionality! Nestled in a quiet, established neighborhood zoned for highly desirable schools, this 3-bedroom, 2-bathroom, 1,120 sqft home offers a cozy yet efficient footprint. The heart of the home features a bright and open eat-in kitchen, making meal prep and entertaining a breeze. You will love the generous-sized bedrooms that provide ample closet space and privacy. Step outside to your great-sized backyard—an ideal canvas for gardening, pets, or summer BBQs. Hobbyists and DIY enthusiasts will look no further than the attached converted garage, complemented by an extra storage workshop for tools, gear, or weekend projects. Don't miss this rare opportunity to own a move-in-ready gem in a fantastic community!

817 Dana Drive, West Chesapeake

$345,900

2 Beds ⋅ 2.1 Baths ⋅ 10644649 MLS

Welcome to Piney Grove, an exquisite community in Western Branch, Chesapeake, where fine finishes & quality construction meet modern living. This 2-level plan beautifully showcases an open floorplan w/ luxurious upgrades. The kitchen stuns guests w/ upgraded quartz countertops, subway tile backsplash, & soft-close drawers. Easily maintained & durable LVP flooring & crown molding throughout 1st level. Lighted tray ceiling in primary bedroom. WIC's in both bedrooms. Quartz vanity in primary bath w/ glass-enclosed shower. Enjoy exceptional amenities, including stet-of-the-art clubhouse & sparkling pool, great for relaxation & socializing. Discover your new home today! Call agent to schedule an appointment & to take advantage of pre-opening special pricing!

4987 Boone Road, West Chesapeake

$565,000

4 Beds ⋅ 3 Baths ⋅ 10644284 MLS

Immaculate, move-in ready 4BR/3BA ranch nestled on a quiet cul-de-sac offers a perfect blend of comfort & functionality with an open floor plan and easy one level living! Rare in-law suite is great for multigenerational living, guests, or private home office. Spacious living area opens to kitchen with large island and new appliances! Primary Bedroom offers walk-in closet, ensuite with double sinks with shower & soaking tub! Relaxing screen porch overlooks peaceful, private backyard & patio is ready for summer cookouts! Peace of mind with upgraded appliances, water heater, and HVAC components being replaced within past 3 years! Pride of ownership shines throughout! Outside bonus features extended parking pad for RV, boats, etc...Combining immaculate condition, flexible living spaces, and desirable private setting, this beauty is a rare find! Conveniently located minutes to 664 for easy access to all of Hampton Roads with nearby dining, shopping, Western Branch schools!

1217 Willow Lakes Court, West Chesapeake

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