Rollingwood Real Estate

Welcome to Rollingwood, a charming neighborhood nestled in the heart of Simpsonville, South Carolina, within the vibrant Greenville County. Known for its picturesque landscapes and inviting community atmosphere, Rollingwood offers residents the perfect blend of suburban tranquility and urban convenience.

As you wander through the tree-lined streets of Rollingwood, you’ll be captivated by the well-maintained homes that reflect a variety of architectural styles, from cozy ranches to modern two-stories. The neighborhood boasts spacious yards and beautiful gardens, making it a delightful place for families, retirees, and everyone in between to call home.

Rollingwood is not just about beautiful homes; it’s also about community. Neighbors frequently gather for seasonal events, fostering a strong sense of belonging. Children can often be seen playing in the parks, and families enjoy weekend picnics in the green spaces that dot the area. The neighborhood is also conveniently located near top-rated schools, making it an ideal choice for families seeking quality education for their children.

For those who enjoy outdoor activities, Rollingwood is just a stone’s throw away from scenic parks and recreational facilities. With easy access to walking trails, playgrounds, and sports courts, there’s no shortage of ways to stay active and enjoy the natural beauty that surrounds you.

In addition to its serene environment, Rollingwood offers quick access to Simpsonville’s thriving downtown area, where you’ll find a delightful mix of shops, restaurants, and entertainment options. With its friendly vibe and prime location, Rollingwood is truly a hidden gem in the Upstate of South Carolina. Come discover your new home in this welcoming community!

Newest Listings in Rollingwood

$1,147,500

5 Beds ⋅ 5 Baths ⋅ 339268 MLS

Private FULL BRICK ESTATE situated directly across from FOX RUN COUNTRY CLUB on 4 ACRES. Enjoy ONE-LEVEL LIVING with OVER 5,500 SQ FT plus a SECLUDED INGROUND POOL. This luxury home is ideal for entertaining with an OPEN FLOOR PLAN, EXPANSIVE ROOMS, and multiple gathering spaces. Guests arrive via the STATELY CIRCULAR DRIVE leading to an arched brick entry. Inside, the gracious foyer opens to a large flex room currently used as an office and a PRIVATE PRIMARY SUITE with bath. From this wing, enjoy SUNRISE GOLF COURSE VIEWS and SUNSET POOL VIEWS. To the left of the foyer, the oversized living room features HARDWOOD FLOORS, A GAS LOG FIREPLACE, BUILT-INS, and a BABY GRAND PIANO. The flowing layout continues to the formal dining room with WAINSCOTING & CROWN MOLDING. The kitchen offers GRANITE COUNTERS, TILED BACKSPLASH, a WORK ISLAND, WHITE CABINETRY, and a SINK OVERLOOKING THE GOLF COURSE, plus a large breakfast area. A separate great room invites hours of enjoyment with a WOOD-BURNING FIREPLACE, BILLIARDS AREA, and movie-night space. Additional features include an OVERSIZED LAUNDRY ROOM, pantry, and CRAFT ROOM/POTENTIAL 6TH BEDROOM with wall-to-wall cabinetry. A SECOND PRIMARY BEDROOM includes a sitting area, WALK-IN CLOSET, and ENSUITE BATH. Another bedroom with an ensuite bath plus TWO BEDROOMS WITH A SHARED BATH provide generous accommodations for family and guests. Relax year-round in the SLATE-FLOORED SUNROOM WITH BUILT-INS overlooking the pool, or unwind outdoors on the COVERED BACK PORCH WITH AWNINGS. OWNED SOLAR PANELS provide energy efficiency and lower utility costs. POOL TABLE AND BABY GRAND PIANO CONVEY. HORSES ARE WELCOME, and the acreage offers future options. Prime location that blends small-town charm with convenience: only ~20–25 minutes to Greenville. Enjoy: • GOLF-COURSE VIEWS & COUNTRY CLUB LIFESTYLE • Parks, green spaces, and outdoor recreation • Local restaurants from casual brunch to date-night dining • Easy access to shops, services, and community events • Highly desirable schools and welcoming neighborhood feel

136 Club Dr, Simpsonville

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The Listings data contained on this website comes from various participants of The Multiple Listing Service of Greenville, SC, Inc. Internet Data Exchange. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The properties displayed may not be all the properties available. All information provided is deemed reliable but is not guaranteed. © 2026 Greater Greenville Association of REALTORS®. All Rights Reserved. Last Updated