Search Homes for Sale

Rollingwood Homes for Sale in Simpsonville, SC

Rollingwood centers on Club Drive, and the name is a fair description of the ground — this is not the flat, uniform grading of a recent subdivision. Four- and five-bedroom homes here have listed into seven figures, which puts Rollingwood among the more established high-end addresses in Simpsonville rather than among the newer builds spreading out from Fairview Road.

Buyers usually arrive here after deciding they want mature trees and a real lot more than they want a warranty. That trade is the whole decision: a house in Rollingwood will not have current energy code or a builder to call, but it will have setting that a new community cannot manufacture for another twenty years. If the balance tips the other way, new construction in Simpsonville is the honest comparison.

Rollingwood Listings

$1,340,000
4 Beds ⋅ 3.5 Baths ⋅ 1600537 MLS
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 ⋅ 1597228 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 Drive, Simpsonville
$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
$465,000
4 Beds ⋅ 2.5 Baths ⋅ 1541524 MLS
Near Fox Run Country Club discover your own slice of paradise in this stunning 4-bedroom, 2.5-bath home, thoughtfully designed in a striking mid-century modern style. Nestled on a sprawling 2.2-acre lot, this property offers both privacy and natural beauty, complete with a spring-fed creek that gracefully meanders through the landscape. You'll be welcomed by lush greenery and over 300 vibrant azalea bushes, creating a colorful backdrop for this unique home. The wooded surroundings provide a serene and tranquil atmosphere, perfect if you're seeking a peaceful retreat. Inside, the home features an inviting layout with plenty of natural light and funky design elements. From the hexagonal living and dining room, to the double sided fireplace, and exquisite ceilings, this home is truly one-of-a-kind. The primary suite boasts a private screened porch, ideal for sipping morning coffee or unwinding in the evenings while enjoying the sounds of nature. There are three additional bedrooms, all ample size, and one of the secondary bedrooms even offers incredible potential with a spacious closet that is also already plumbed for an additional bathroom. The layout could easily be modified to accommodate a full staircase, leading to a huge unfinished space upstairs, perfect for your creative studio, additional living area, or extra bedrooms. The property is equestrian-friendly, making it ideal for horse lovers or anyone looking to embrace a country lifestyle, feeling tucked away from the hustle and bustle, while still being just minutes from shopping and dining options! Don't miss your chance to own this extraordinary property that blends mid-century charm with modern potential; Schedule a viewing today and envision the possibilities!

9 Green Hill Drive, Simpsonville
$950,000
4 Beds ⋅ 4.5 Baths ⋅ 1517852 MLS
A gem in the country with over 4000 sq. ft. of great home , 1500 sq.ft. detached workshop on just less than 3 acres close to the Fox Run Country Club. This is a wonderful Donald Gardner Plan!!!! This 4 bedroom, 4 .5 bath home has a two main level bedroom master suites with two walk-in closets , a sitting room and two full bathrooms with radiant heated ceramic tile floors. One of the master bathrooms has a roll-in shower While the other has a jetted garden tub and separate shower. This unique set up can be modified if needed. This was specific for the original owner. Two more spacious bedrooms upstairs with two more full baths, plus a hobby/craft/office room that is a pass through into a very large 27'x13' Bonus room or Media Room. Great use of space in this house. Two walk-in attic spaces for additional storage. One of the spaces exceeds 200 sq. ft. of space easy to condition. This is an Energy Star Rated home with state of the arty foam insulation on the under side of the roof. Fantastic low temperatures in the attic which translates into lower utility power bills. The attached oversized two car garage has two 10' wide doors that are 8' tall. Outside of the yard /utility door is a trusty gas generator already installed for added utility security. The 2.8+ acre lot is surrounded by mature shade trees providing privacy and peaceful living. Lots of nature to view from the nearly 250+/- sq. ft. back Patio . Enjoy grilling your favorite meals off the patio as it has a natural gas hook ........never run out of gas this way. The kitchen has been upfitted with Cambria Quartz counter tops and tile backsplash. Breakfast area family room, screen porch and kitchen all flow for great gatherings. Great appliances with double convection wall ovens, microwave and warming drawer. The driveway parking pad can easily accommodate 10+ cars. Great for holiday gatherings. For the car hobbyist or wood shop enthusiast please take the time to explore the detached garage. Two garage doors and at least 3 car capacity. Separate electrical service. The main house has 400 Amp service and the Workshop has a separate meter with an additional 200 Amp service . This garage has security alarm system, internet, 900 heated / cooled sq. ft. and 600 non heated. You also have a half bath to add to the comfort of a shop on your property. Additional features are two water heaters, automatic Lawn irrigation system, Home security system, level lot, Hardwood floors are upper end Teak wood, termite warranty Bond, public water, Septic system, great space for an inground pool, recirculated hot water for the first floor, UV Light filtration system as part of the HVAC system...etc..... So many more details to discuss. Just inquire further. 30 easy driving minutes to Downtown Greenville for fine dining or entertainment, 20 minutes to the GSP International airport. An easy 15 minutes to over 8 grocery stores, multiple restaurants and other shoppes.

20 Green Hill Drive, Simpsonville
Start Your Search

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

“ Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Some IDX listings have been excluded from this website. Properties may or may not be listed by the office/agent presenting the information © 2026 Canopy MLS as distributed by MLS GRID”

Last Updated: