Rollingwood Estates Homes for Sale

Welcome to Rollingwood Estates, a hidden gem nestled in the heart of South Chesapeake, Virginia. This picturesque neighborhood is known for its lush greenery, friendly atmosphere, and a strong sense of community, making it the perfect place for families, retirees, and everyone in between. With tree-lined streets and well-maintained parks, Rollingwood Estates offers a serene environment that feels like a breath of fresh air.

One of the highlights of this charming neighborhood is its proximity to excellent schools, shopping centers, and recreational facilities. Families will appreciate the top-rated schools in the area, ensuring that children receive a quality education just a stone's throw away from home. For those who enjoy outdoor activities, the nearby parks and walking trails provide ample opportunities for leisurely strolls, picnics, and weekend adventures.

When it comes to homes for sale in Rollingwood Estates, you'll find a diverse selection that caters to various tastes and budgets. From cozy single-family homes to spacious properties with modern amenities, there’s something for everyone. Many homes boast beautiful yards and inviting interiors, perfect for entertaining friends or enjoying a quiet evening with family. With the real estate market in this area thriving, now is an excellent time to explore your options and find your dream home.

Embrace the charm of Rollingwood Estates and discover a community that feels like home. Whether you’re searching for a place to raise a family or simply looking for a peaceful retreat, this neighborhood has it all. Come see for yourself why so many are proud to call Rollingwood Estates their home!

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 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

Start Your Search

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.