Rollingwood Estates Homes for Sale

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 urban convenience, making it an ideal place for families, professionals, and retirees alike. With its picturesque tree-lined streets and beautifully manicured lawns, Rollingwood Estates exudes a warm and inviting atmosphere that you’ll be proud to call home.

Homes for sale in Rollingwood Estates reflect a variety of architectural styles and sizes, catering to diverse preferences and lifestyles. From cozy single-family homes to spacious residences, each property boasts unique features that enhance comfort and functionality. Many of the homes in this community come equipped with modern amenities, open floor plans, and expansive backyards, perfect for entertaining or enjoying quiet evenings under the stars.

The community is conveniently located near major highways, providing easy access to nearby shopping, dining, and recreational opportunities. Families will appreciate the proximity to excellent schools, parks, and community centers, fostering a strong sense of neighborhood camaraderie. Whether you’re taking a leisurely stroll through the local parks or enjoying a day at the nearby Chesapeake City Park, there’s no shortage of outdoor activities to keep you engaged.

If you’re looking for a place that combines the charm of suburban living with the conveniences of city life, look no further than Rollingwood Estates. Explore the homes for sale today and discover the perfect backdrop for your next chapter in life!

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

$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

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.