Rollingwood - Area 32 Homes for Sale

Welcome to Rollingwood - Area 32, a hidden gem nestled in the heart of Simpsonville, South Carolina. This charming subdivision, located in Greenville County, offers a perfect blend of suburban tranquility and convenient access to urban amenities. Rollingwood is known for its picturesque landscapes, friendly neighbors, and a strong sense of community, making it an ideal place for families and individuals alike.

One of the standout features of Rollingwood is its diverse range of homes for sale. Whether you’re seeking a cozy starter home or a spacious family residence, you’ll find a variety of architectural styles and layouts to suit your needs. Many homes in this area boast modern finishes, open floor plans, and well-manicured lawns, providing a welcoming atmosphere for both residents and guests. The community is designed with comfort in mind, featuring ample green spaces and walking trails that encourage an active lifestyle.

Living in Rollingwood means enjoying the best of both worlds. You’ll have access to top-rated schools, local parks, and a vibrant downtown area filled with shopping, dining, and entertainment options. The nearby I-385 makes commuting to Greenville and beyond a breeze, allowing you to explore all that the Upstate has to offer.

If you’re looking for a place where community spirit thrives, and beautiful homes are waiting just for you, Rollingwood - Area 32 is the perfect destination. Explore the available homes for sale and discover the lifestyle that awaits you in this delightful Simpsonville neighborhood. Your dream home is just a visit away!

Newest Rollingwood - Area 32 Homes for Sale

$1,340,000

4 Beds ⋅ 3.5 Baths

Welcome to this magnificent sprawling estate approximatley 2.3 acres in the heart of Simpsonville, perfectly positioned across from Fox Run Country Club and its beautiful golf course. Set well back from the road at the end of a long, winding driveway, this spectacular custom-built brick home is surrounded by mature trees, creating a private, park-like setting enhanced by custom LED landscape lighting. Offering two spacious stories plus a finished walkout basement, this remarkable property provides an abundance of flexible living and entertaining space. From the moment you enter, you will appreciate the quality craftsmanship showcased through graceful archways, extensive custom moldings, beautiful hardwood floors and custom built-in cabinetry. The expansive great room features a gas-log fireplace and flows seamlessly into the gourmet kitchen and breakfast area. Just beyond, a charming covered brick veranda offers a peaceful setting for morning coffee, outdoor dining or relaxing while enjoying the serene surroundings. The luxurious main-level primary suite features hardwood flooring, a tray ceiling and a beautifully appointed ensuite bath complete with dual vanities, a deep soaking tub, separate shower and spectacular custom-designed closet. Open-railing hardwood staircases add architectural interest while connecting the home’s three finished levels. Upstairs, a spacious loft library creates an inviting reading or study area, accompanied by two generously sized bedrooms with walk-in closets and an impressive media room perfect for movie nights. The finished walkout basement expands the possibilities with a private exterior entrance as well as interior access from the main home. This level includes an additional bedroom with a private bath, a large den with a wet bar and exceptional storage throughout. A third garage bay and workshop are also located on the basement level, conveniently accessed by a continuous concrete driveway—ideal for additional vehicles, hobbies or projects. Thoughtful construction, impressive framing, high-end mechanical upgrades and an abundance of closets and storage further distinguish this exceptional residence. Although the setting feels peaceful and secluded, the home is only minutes from the shopping, dining and conveniences of the Five Forks area. For those seeking acreage, privacy, remarkable living space and custom craftsmanship in a truly special Simpsonville location, this extraordinary estate is a must-see. Welcome home!

156 Club Drive, Simpsonville

$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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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