Jolliff Woods Real Estate

Welcome to Jolliff Woods – a hidden gem nestled in the heart of West Chesapeake, Virginia! This charming subdivision offers a perfect blend of suburban tranquility and modern convenience, making it an ideal choice for families, professionals, and retirees alike.

Jolliff Woods boasts an inviting atmosphere, characterized by its tree-lined streets and beautifully manicured lawns. With a variety of well-appointed homes, each exuding its unique charm, residents enjoy a sense of community that is both warm and welcoming. The architecture here is diverse, featuring contemporary styles alongside classic designs, ensuring that there is something for everyone.

One of the standout features of Jolliff Woods is its proximity to a wealth of amenities. Residents can take advantage of nearby shopping centers, restaurants, and recreational facilities, all just a short drive away. The area is also home to several parks and green spaces, perfect for outdoor enthusiasts and families looking to enjoy the beautiful Virginian weather.

Education is a top priority in this community, with highly-rated schools serving the area, making it an attractive option for families with children. Additionally, Jolliff Woods is conveniently located near major highways, providing easy access to the bustling cities of Norfolk and Virginia Beach, as well as the serene landscapes of the Chesapeake Bay.

Whether you're seeking a peaceful retreat or a vibrant community, Jolliff Woods in West Chesapeake, VA, offers the perfect blend of both. Come explore this delightful neighborhood and discover your dream home in this picturesque setting!

Newest Listings in Jolliff Woods

$570,000

4 Beds ⋅ 2.1 Baths ⋅ 10649934 MLS

Wonderful home located in the desirable Joliff Woods neighborhood. This 4 bedroom, 2.5 bath offers approx. 2,710 square feet of living space. Situated on a generous size corner lot. Screen Porch and rear yard is completely fenced. Seller took care of all the big ticket items. Downstairs hardwood floors have just been refinished. New Windows & Slider Doors 2020, Brand New Upstairs HVAC systems, All Exterior Composite Trim, Leaf Filter Gutter Guards, & more. Conveniently located with easy access to the Southside & Peninsula, military bases, shipyards, dining, and shopping.

4700 Harlequin Way, West Chesapeake

$540,000

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

$565,000

4 Beds ⋅ 2.1 Baths ⋅ 10647147 MLS

Welcome to this beautifully updated home featuring a spacious yard and a sparkling saltwater pool, for relaxing or entertaining. Inside, you'll find freshly refinished hardwood floors, fresh interior paint, and a stunning new light fixture that adds a modern touch. The kitchen boasts custom cabinetry, while the bathrooms have been updated with new vanities. Major improvements include a new HVAC system (2025), a new fence (2024), and a tankless water heater for added efficiency. Additional features include a whole-house water filtration system, offering comfort and peace of mind. This move-in-ready home combines timeless charm with thoughtful upgrades inside and out.

4712 White Owl Crescent, 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

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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.