Rollingwood Estates Real Estate

Welcome to Rollingwood Estates, a hidden gem nestled in the heart of South Chesapeake, Virginia. This charming neighborhood boasts a perfect blend of suburban tranquility and modern convenience, making it an ideal place for families, young professionals, and retirees alike.

Rollingwood Estates is characterized by its picturesque tree-lined streets, well-manicured lawns, and friendly neighbors who take pride in their community. The area features a delightful mix of single-family homes, each showcasing unique architectural styles that reflect the warmth and character of the neighborhood. With spacious yards and inviting porches, Rollingwood Estates offers the perfect backdrop for outdoor gatherings and family activities.

One of the standout features of this community is its proximity to nature. Residents enjoy easy access to nearby parks and recreational areas, including the scenic Chesapeake City Park, where you can explore walking trails, picnic areas, and playgrounds. For those who love water activities, the Elizabeth River is just a stone's throw away, offering opportunities for kayaking, fishing, and leisurely boat rides.

Convenience is key in Rollingwood Estates, with shopping centers, dining options, and top-rated schools all within a short drive. The neighborhood is also well-connected to major highways, making it easy to commute to nearby cities or enjoy a weekend getaway.

In Rollingwood Estates, you’ll find a welcoming community spirit that fosters connections and friendships. Whether you're taking a stroll through the neighborhood or enjoying a weekend barbecue at the local park, you'll quickly discover why Rollingwood Estates is not just a place to live, but a place to call home.

Newest Listings in Rollingwood Estates

$985,000

6 Beds ⋅ 5.1 Baths ⋅ 10648547 MLS

OPEN HOUSE SUNDAY NOON-2:00 Welcome to this impressive all-brick home offering over 5,000 sq. ft. of versatile living space and exceptional indoor–outdoor amenities. With 6 bedrooms, 5.5 bathrooms, and an additional first-floor flex room perfect as a 7th bedroom, home office, or formal living area, this home adapts beautifully to your lifestyle. Five of the bedrooms include private en-suite bathrooms, giving everyone their own comfortable retreat. A bright, oversized sunroom—equipped with heating and cooling but not included in the home’s total square footage—adds even more year-round living space. Step outside to your own backyard oasis. Brick pool house with heating/cooling + full bathroom. In-ground saltwater pool with a new liner ( installed 2025). Hot tub for 6. Expansive patio area for entertaining and relaxing. The property also features a three-car garage plus a half-circle driveway providing abundant parking for guests . Freshly painted, new carpets, refinished wood floors.

844 Greenfield Lane, 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.