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 conveniences, making it an ideal place to call home for families, retirees, and everyone in between.

Rollingwood Estates is characterized by its picturesque tree-lined streets, spacious lots, and beautifully designed homes that reflect a variety of architectural styles. The community exudes a warm, welcoming atmosphere, where neighbors become friends and gatherings are a cherished tradition. With meticulously maintained landscaping and a strong sense of pride among residents, it’s no wonder that Rollingwood Estates is a sought-after destination in Chesapeake.

Families will appreciate the proximity to highly-rated schools, parks, and recreational facilities. The local parks provide ample opportunities for outdoor activities, from picnicking to hiking, ensuring that every member of the family can enjoy the great outdoors. Additionally, the community is conveniently located near shopping centers, restaurants, and entertainment options, making daily errands a breeze.

For those who commute, Rollingwood Estates offers easy access to major highways, allowing for a smooth journey to nearby cities and employment hubs. Whether you’re looking for a peaceful retreat after a long day or a vibrant community to engage with, Rollingwood Estates has it all.

Come experience the charm and warmth of Rollingwood Estates, where your dream home awaits in this delightful corner of South Chesapeake, VA. Discover the lifestyle you’ve always wanted in a community that feels like family.

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 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

$850,000

5 Beds ⋅ 3 Baths ⋅ 10648245 MLS

Beautifully updated Great Bridge home offering exceptional indoor-outdoor living and thoughtfully designed spaces throughout. The resort-style backyard features a fiberglass saltwater pool, outdoor kitchen w/ granite countertops, refrigerator, sink & natural gas-line plumbed grill, expansive deck, enclosed sunroom, professional landscape lighting & wooded backdrop; creating a private setting for entertaining or relaxing. Inside, enjoy open-concept living, a first-floor bedroom w/ ensuite bath, new flooring, custom Closet Factory primary closet, library/office & wine storage, plus built-in surround sound extending to the sunroom & outdoors. Additional upgrades include newer HVAC systems, irrigation w/dedicated well, LeafGuard gutters, expanded parking & garage storage. Zoned for sought-after Great Bridge schools and conveniently located near shopping, dining & everyday amenities. Beautifully maintained and thoughtfully upgraded, this home delivers space, comfort & effortless entertaining within a tree-lined community known for neighborhood events and a welcoming atmosphere.

712 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.