Jolliff Woods Homes for Sale

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 conveniences, making it an ideal place for families, retirees, and everyone in between. With tree-lined streets and beautifully landscaped yards, Jolliff Woods provides a serene environment that invites you to unwind and enjoy the beauty of nature.

The homes for sale in Jolliff Woods showcase a variety of architectural styles, each designed to cater to diverse tastes and lifestyles. From cozy single-family homes to spacious two-story residences, there's something here for everyone. Many of these properties boast open floor plans, updated kitchens, and expansive backyards – perfect for entertaining guests or enjoying quiet evenings under the stars. The community is known for its friendly atmosphere, where neighbors become friends and families thrive together.

Living in Jolliff Woods means easy access to top-rated schools, parks, and recreational facilities. Whether you’re exploring the nearby Great Dismal Swamp National Wildlife Refuge or enjoying a weekend at the local farmer’s market, there’s always something to do. With convenient access to major highways, commuting to nearby cities or enjoying a day at the beach is a breeze.

If you’re looking for a place to call home in Chesapeake, Jolliff Woods is a wonderful choice. Explore the homes for sale today and discover the perfect blend of comfort, community, and convenience that awaits you in this delightful neighborhood!

Newest Jolliff Woods Homes for Sale

$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.