Jolliff Woods Real Estate

Welcome to Jolliff Woods, a hidden gem nestled in the heart of West Chesapeake, Virginia. This charming neighborhood is known for its welcoming community spirit, picturesque landscapes, and a perfect blend of suburban tranquility and urban convenience.

As you stroll through the tree-lined streets of Jolliff Woods, you’ll be captivated by the well-maintained homes that reflect a variety of architectural styles, creating a warm and inviting atmosphere. The community is characterized by spacious lots, manicured lawns, and a sense of pride among residents. Families will appreciate the friendly neighborhood vibe, where children can play safely and neighbors often become lifelong friends.

Jolliff Woods is ideally situated just minutes away from major highways, making commuting a breeze. Residents enjoy easy access to Chesapeake’s bustling shopping centers, delightful dining options, and recreational parks. The nearby Chesapeake City Park and Great Dismal Swamp National Wildlife Refuge offer outdoor enthusiasts plenty of opportunities for hiking, biking, and birdwatching, ensuring that nature is always within reach.

Education is a top priority in this community, with highly-rated schools serving the area, providing families with excellent educational opportunities for their children.

Whether you’re looking to settle down or simply explore, Jolliff Woods offers a unique blend of comfort, convenience, and community. Experience the charm of this delightful neighborhood and discover why so many choose to call Jolliff Woods home. Your dream lifestyle awaits in West Chesapeake!

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

$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.