Rollingwood Estates Homes for Sale

Welcome to Rollingwood Estates, a hidden gem nestled in the heart of South Chesapeake, Virginia. This charming neighborhood boasts a perfect blend of tranquility and convenience, making it an ideal place for families and professionals alike. With tree-lined streets, well-maintained parks, and friendly neighbors, Rollingwood Estates exudes a warm, welcoming atmosphere that feels like home the moment you arrive.

Rollingwood Estates is known for its spacious homes, many of which feature beautiful architectural designs and lush gardens. Whether you’re searching for a cozy single-family home or a larger property with ample space for entertaining, this neighborhood offers a variety of homes for sale to suit your needs. The properties are often characterized by modern amenities, open floor plans, and inviting outdoor spaces—perfect for enjoying Virginia's beautiful seasons.

Residents of Rollingwood Estates enjoy easy access to a plethora of local amenities, including shopping centers, restaurants, and recreational facilities. The nearby Chesapeake City Park and the scenic Elizabeth River offer opportunities for outdoor activities such as hiking, biking, and picnicking. Families will appreciate the top-rated schools in the area, providing excellent educational opportunities for children.

With its prime location, friendly community, and diverse housing options, Rollingwood Estates is more than just a neighborhood; it’s a place where memories are made and dreams come true. Explore the homes for sale today and discover the perfect spot to start your next chapter in this delightful community!

Newest Rollingwood Estates Homes for Sale

$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 bathrooms, giving everyone their own comfortable retreat. A bright, oversized sunroom— but not included in the home’s total square footage. 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, South 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.