Rollingwood Estates Real Estate

Welcome to Rollingwood Estates, a hidden gem nestled in the heart of South Chesapeake, Virginia. This charming subdivision offers a perfect blend of suburban tranquility and modern convenience, making it an ideal place to call home. With its picturesque tree-lined streets and beautifully landscaped yards, Rollingwood Estates is designed for those who appreciate the beauty of nature while enjoying the comforts of contemporary living.

Rollingwood Estates boasts a variety of well-appointed homes, each showcasing unique architectural styles that cater to diverse tastes. Whether you're a first-time homebuyer or looking to upgrade, you'll find an array of options that fit your lifestyle and budget. The community is known for its friendly atmosphere, where neighbors become friends and families thrive.

One of the standout features of Rollingwood Estates is its proximity to excellent schools, parks, and recreational facilities. Families will appreciate the highly-rated Chesapeake Public Schools, ensuring a top-notch education for children. For outdoor enthusiasts, nearby parks offer ample opportunities for hiking, picnicking, and enjoying the great outdoors.

Convenience is key in Rollingwood Estates, with easy access to major highways and local amenities. Shopping, dining, and entertainment options are just a short drive away, making it simple to enjoy everything South Chesapeake has to offer.

Experience the charm and community spirit of Rollingwood Estates, where you can create lasting memories in a beautiful setting. Discover your dream home today and become part of this vibrant neighborhood!

Newest Listings in Rollingwood Estates

$779,000

5 Beds ⋅ 3.1 Baths ⋅ 10661180 MLS

Are you looking for a home with a multi gen suite? We have it! Welcome to Parkside Manor, an enclave of just 20 exclusive homesites located within desirable Rollingwood Estates. The exceptional Caymus model offers a luxurious 1st floor multi gen suite complete w/ living room, bedroom, full bath & 2 walk in closets w/ separate entry from foyer. The expansive open concept floor plan creates effortless flow from the great room to the dining room & beautifully appointed gourmet kitchen. Upstairs, the impressive primary ensuite offers a serene sanctuary for relaxation & privacy. A media room,large laundry room, 3 additional bedrooms & full bathroom complete the second floor. Adding to Parkside Manor's exceptional appeal, most homesites offer picturesque views of either Cheshire Forest Lake or a tranquil pond with a water feature & walking trail, creating a peaceful setting surrounded by natural beauty. Parkside Manor is located at corner of Flax Mill Drive & Flax Mill Way. Ask for details

MM Caymus Multi Gen, South Chesapeake

$740,000

4 Beds ⋅ 3.1 Baths ⋅ 10661198 MLS

Welcome to Parkside Manor, an enclave of just 20 exclusive homesites located within desirable Rollingwood Estates. With clean contemporary lines, the Sonoma offers a thoughtfuly designed floor plan which features an open concept great room with fireplace, light filled sunroom & gourmet kitchen w/ large kitchen island. A versatile first floor guest suite or private office w/ full bathroom provides flexibility for today's lifestyles. Upstairs, enjoy a luxurious primary retreat with spa inspired bath, 2 large walk in closets, spacious secondary bedrooms, loft, large laundry room & hall bathroom. Adding to Parkside Manor's exceptional appeal, most homesites offer picturesque views of either Cheshire Forest Lake or a tranquil pond with a water feature & walking trail. Ask about current incentives!

MM Sonoma, South Chesapeake

$950,000

6 Beds ⋅ 5.1 Baths ⋅ 10658157 MLS

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. Interior pics 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.

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Rollingwood Estates Real Estate

Newest Listings in Rollingwood Estates

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