Rollingwood Estates Homes for Sale

Welcome to Rollingwood Estates, a hidden gem nestled in the heart of South Chesapeake, Virginia. This charming neighborhood is a perfect blend of tranquility and community spirit, making it an ideal place to call home. Rollingwood Estates is characterized by its picturesque tree-lined streets, well-maintained parks, and friendly neighbors who take pride in their community.

As you stroll through the neighborhood, you’ll be captivated by the variety of homes available for sale. From cozy single-family residences to spacious modern designs, Rollingwood Estates offers a diverse range of architectural styles to suit every taste and lifestyle. Many of these homes boast large yards, perfect for family gatherings or quiet evenings under the stars. With a strong sense of community, residents often gather for neighborhood events, fostering friendships and creating lasting memories.

Rollingwood Estates is conveniently located near major highways, making commuting to nearby cities a breeze. Local amenities, including shopping centers, restaurants, and recreational facilities, are just a short drive away, ensuring you have everything you need within reach. Families will appreciate the highly-rated schools in the area, providing quality education for children of all ages.

If you are looking for a place that combines the charm of suburban living with the conveniences of urban life, look no further than Rollingwood Estates. Explore the homes for sale today and discover the perfect setting for your next chapter. Embrace the warmth and community spirit of Rollingwood Estates, where your dream home awaits!

Newest Rollingwood Estates Homes for Sale

$965,000

6 Beds ⋅ 5.1 Baths ⋅ 10648547 MLS

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. INTERIOR PHOTOS ARE VIRTUALLY STAGED

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.