Rollingwood - Area 32 Homes with Hillcrest High school

Rollingwood - Area 32 Homes with Hillcrest High school

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 a strong sense of community, Rollingwood is the perfect place for families, young professionals, and retirees alike.

As you stroll through the tree-lined streets of Rollingwood, you'll be captivated by the beautiful homes that showcase a variety of architectural styles, from cozy ranches to modern two-story designs. Many of the properties feature spacious yards, perfect for outdoor gatherings, gardening, or simply enjoying the serene surroundings. The neighborhood is known for its well-maintained homes and welcoming atmosphere, making it an ideal spot for those looking to settle down in a peaceful yet vibrant community.

One of the standout features of Rollingwood is its proximity to Hillcrest High School, which is just a stone’s throw away. This highly regarded institution is known for its strong academic programs and commitment to student success. Families with school-aged children will appreciate the convenience of having quality education within easy reach, fostering a strong sense of community involvement and pride.

In addition to its educational offerings, Rollingwood boasts easy access to a variety of parks, shopping centers, and dining options. The nearby downtown Simpsonville is bursting with local boutiques, restaurants, and entertainment venues, creating a lively atmosphere for residents to enjoy.

If you're seeking a neighborhood that combines the warmth of community living with the conveniences of modern life, Rollingwood in Simpsonville is the perfect place to call home. Come and discover the charm of this delightful neighborhood, where every day feels like a breath of fresh air!

Newest Rollingwood - Area 32 Homes with Hillcrest High school

$1,147,500
5 Beds 4.5 Baths
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 Drive, Simpsonville

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