Luxury Homes for Sale in Simpsonville

Nestled in the heart of Simpsonville, South Carolina, Century 21 Vanguard presents an exquisite collection of luxury homes that redefine opulent living. Each residence within this exclusive portfolio is a testament to architectural mastery and sophisticated design, embodying the epitome of refined elegance in one of the Upstate's most sought-after communities. The homes for sale through Century 21 Vanguard showcase a harmonious blend of contemporary aesthetics and timeless craftsmanship in Simpsonville. From the grand entrances to the panoramic views and high-end finishes, these residences exude an atmosphere of indulgence and luxury. What sets these homes apart is their bespoke design, ensuring each property stands as a unique work of art. With options ranging from modern architectural marvels to classic estates, Century 21 Vanguard caters to diverse tastes with an unparalleled level of personalized luxury.

Simpsonville's luxury homes offer an abundance of amenities that enhance the living experience. Private gardens, serene pools, and outdoor spaces cater to both entertainment and relaxation. Each residence serves as a private getaway, where residents can unwind and revel in their surroundings' exclusivity. Beyond the lavish interiors, Century 21 Vanguard goes above and beyond to deliver a seamless, personalized experience for buyers. This ensures that each individual finds not just a house but a home that reflects their unique lifestyle and aspirations. Simpsonville's prime location provides easy access to the city's vibrant cultural scene, upscale dining, and high-end shopping destinations. Yet, amidst this urban excitement lies a sense of tranquility within the community - striking a perfect balance between cosmopolitan living and small-town charm. Simply put, Century 21 Vanguard's luxury homes in Simpsonville exemplify the ultimate in residential living in the Upstate. Emphasizing individuality, opulence, and attention to detail like no other, these residences redefine the standards of luxury living - offering an exceptional lifestyle for those seeking sophistication and comfort at its finest.

You may also want to check out Greenville Luxury Homes for Sale.

Luxury Listings in Simpsonville

$985,000

4 Beds ⋅ 3.5 Baths ⋅ 1598623 MLS

All-Brick. Three levels. Three-car garage. Over 5,300 square feet. Welcome to 1 Glengrove Drive, a home right in the heart of Five Forks Simpsonville that boasts a floor plan designed for those who need room to spread out, with multiple living areas and dedicated spaces that can evolve with your lifestyle. Step inside to soaring ceilings, rich hardwood floors, a dramatic two-story great room filled with natural light, and a sweeping staircase that makes an unforgettable first impression. The main level features formal living and dining rooms, a private office, spacious laundry room, and a beautiful sunroom/conservatory that provides the perfect spot to relax year-round. The real gem is the kitchen, complete with brand-new appliances, abundant cabinetry, boundless prep space, a large center island, and an oversized breakfast area that overlooks the rear grounds. And, don’t miss the half bath and gracious laundry room that rounds out this level. Upstairs, you’ll be greeted by a peaceful owner’s retreat with a spacious bedroom, spa-inspired bathroom and two walk-in closets. There are two additional bedrooms that share a bathroom and a third bedroom that has its own private bathroom. The third level adds even more versatility with two separate flex spaces perfect for a home office, media room, playroom, hobby space, fitness area, or whatever your needs may be. Plus there’s a walk in storage area that any homeowner loves! With this space & size, there is no shortage of options for family, guests, work-from-home needs, and future possibilities. The three-car garage provides valuable storage and parking flexibility, while the outdoor deck offers a place to relax and enjoy the backyard setting. Located in desirable Five Forks Simpsonville with access to community amenities, including pool, tennis & clubhouse as well as nearby shopping, dining, and highly regarded schools, 1 Glengrove Drive offers the rare combination of size, flexibility, and location that today’s buyers are seeking.*Some photos are vittually adjusted.

1 Glengrove Drive, Simpsonville

$1,200,000

4 Beds ⋅ 3.5 Baths ⋅ 1598567 MLS

Welcome to 580 Hipps Road! Are you looking for an estate-style property with no HOA on almost five acres, with extremely close proximity to modern conveniences? Would it make your decision easier if it included a pool? An incredible outbuilding for storage, a gym, or an RV? A primary bedroom on the main level? Situated just minutes from downtown Simpsonville on nearly five acres of beautifully usable property, this stunning custom Craftsman home features 4 bedrooms and 3.5 baths. A welcoming covered front porch, elegantly accented by classic perpetual gas lanterns, invites you inside. Step through the front door to find tall ceilings and beautiful hardwood floors that flow seamlessly into an open living room. Here, a cozy brick fireplace and a striking wall of French doors draw the eye, opening directly out to an enormous back patio. The adjacent chef's kitchen is an absolute dream, boasting a large center island, a dedicated dining area, abundant counter and cabinet space, and a walk-in pantry. Just off the back of the kitchen is a versatile mudroom - the perfect everyday drop zone or pet area. The main level also hosts a huge primary suite that serves as a private retreat. It leads into a spa-like en-suite bath complete with tile floors, a separate soaking tub, and a walk-in tile shower. Beyond the large walk-in closet, you'll find the conveniently located laundry room with a sink. A separate powder room is also located on the main floor for guests. Upstairs, discover a large loft area offering plenty of space for a home office or flex room, alongside three additional bedrooms and two full bathrooms. Thoughtful everyday conveniences like a laundry chute and a walk-in attic storage area complete the upper level. The exterior is a true backyard oasis featuring an in-ground pool and a covered patio perfect for entertaining. The property also includes a massive 30'x38' detached 3-car garage with an attached carport and an additional covered patio, set alongside beautifully cut-in wooded trails. Schedule your private showing today to make this incredible Simpsonville estate yours!

580 Hipps Road, Simpsonville

$975,000

5 Beds ⋅ 3.5 Baths ⋅ 1598454 MLS

Some homes check every box. This one creates a feeling you’ll remember long after you leave. Tucked away on one of the community’s most coveted premium homesites, this extraordinary residence sits on 1.42 private acres, where mature trees, thoughtful landscaping, and resort-style outdoor living create an atmosphere that feels worlds away, yet you’re only minutes from everything Simpsonville and Greenville have to offer. Built for those who love to entertain without sacrificing everyday comfort, this 4,400+ square-foot home was designed around the idea that every space should invite people to gather. Sunlight pours through oversized windows, soaring ceilings create an inviting sense of openness, and every room flows effortlessly into the next. At the heart of the home, conversations naturally begin in the stunning living spaces before carrying into the beautifully appointed kitchen, where every appliance conveys. Tucked away on the main level, the luxurious primary suite offers the perfect private retreat, blending everyday convenience with timeless elegance. Featuring a spa-inspired bath with a beautifully tiled walk-in shower, it’s a space designed to unwind and recharge. As the evening unfolds, guests gravitate to the custom-crafted bar, movie nights come alive in the dedicated media room, and every celebration feels just a little more memorable. Then there’s the backyard… Not just a pool, but your own private escape. The sparkling saltwater pool is surrounded by multiple entertaining areas that invite everything from quiet morning coffee to unforgettable summer evenings. A beautifully designed retaining wall, covered porch, and spacious patio add character and dimension to the landscape, while the fenced pool area offers both privacy and peace of mind. Whether you’re grilling with friends, watching a game from the patio, or enjoying the stars after sunset, this outdoor living experience rivals many luxury vacation homes. Luxury, however, is found in the details. From the striking custom wood front door that creates an unforgettable first impression to the spacious three-car garage, natural gas service, irrigation system, and active termite bond, every feature was selected with comfort and peace of mind in mind. The home is even pre-wired for a home generator, providing added confidence and convenience when it’s needed most. To make settling in even easier, the patio furniture and basketball goal convey, allowing you to begin enjoying the lifestyle from day one. What truly sets this property apart isn’t simply its size or impressive list of upgrades; it’s the rare combination of privacy, craftsmanship, functionality, and effortless indoor-outdoor living. Homes on premium lots like this rarely become available, and even fewer have been cared for with this level of pride. This isn’t simply where you’ll live. It’s where birthdays are celebrated, holidays become traditions, pool days turn into lifelong memories, and ordinary evenings feel a little more extraordinary. Welcome home.

36 Modesto Lane, Simpsonville

$900,000

6 Beds ⋅ 4 Baths ⋅ 1598403 MLS

Nearly 4900 square feet. Over an acre of land. Six bedrooms. Three finished levels. This isn't just a home, it's the space to live every chapter of life without ever feeling like you've outgrown it. Perfectly situated on a beautiful 1.13 acre lot in one of Simpsonville's sought-after communities, 248 Scotts Bluff Drive offers an incredible blend of everyday comfort, thoughtful design, and unmatched versatility. The main level welcomes you with warm, inviting living spaces designed for gathering. The beautifully appointed kitchen features granite and quartz countertops, ample workspace, and opens seamlessly to the breakfast area and spacious living room. A formal dining room is ready for holidays and celebrations, while a main level bedroom and full bath, provide the perfect space for guests, family, or a private home office. Just beyond, the screened porch becomes your favorite place to enjoy quiet mornings, summer evenings, and everything in between. Upstairs, the expansive primary suite feels like a private retreat with a spacious ensuite bath and two walk-in closets. Two additional bedrooms, a full bath, laundry room, and two generous flex rooms create endless opportunities for a media room, playroom, home office, hobby space, or homework headquarters. And then there's the finished basement... More than just extra square footage, it's an entirely separate living experience. Complete with its own full kitchen, living area, laundry, two bedrooms, a full bath, and an additional flex room currently used as a gym. This level offers incredible flexibility for multigenerational living, extended guests, entertaining, or simply spreading out. Outside, the 1.13 acre homesite provides room to breathe, play, garden, entertain, or simply enjoy the privacy that's becoming increasingly hard to find. When you're ready to cool off, the neighborhood pool is just another reason you'll love calling this community home. With nearly 4900 square feet of finished living space, six bedrooms, four full baths, multiple flex rooms, and a floor plan that adapts beautifully to every stage of life, this is more than a place to live - it's a home designed to grow with you. Welcome home.

248 Scotts Bluff Drive, Simpsonville

$1,200,000

5 Beds ⋅ 3.5 Baths ⋅ 1597886 MLS

A Historic Simpsonville Homestead on 10.4 Private Acres Live from the land without leaving Simpsonville behind. Set on 10.4 private acres, 621 Jenkins Bridge Road offers a rare combination of productive land, living history, creative workspace, and flexible multigenerational living. Mature fruit trees, berries, grapes, dedicated honey-processing areas, and a natural stream create the foundation for a working homestead from the day you arrive. An original structure from the historic Brashier family homesite remains on the property, already equipped with electricity and water. It offers compelling potential as a workshop, studio, office, gathering space, or future guest-use project, subject to applicable approvals. The main brick ranch is designed for a household that needs room to live, work, host, and create. The primary level includes a wood-burning fireplace, an island kitchen, and a library with French doors that can serve as an office or flexible guest space. A separately conditioned upper wing provides additional bedrooms, studio space, and a dedicated craft room, while the finished walk-out basement expands the home with recreation, fitness, workshop, office, or poolside entertaining space. Outside, the pool, orchards, stream, historic structure, and open acreage create a property that can be productive, peaceful, and deeply personal. This is not simply a house with land. It is a place for growers, makers, hosts, and anyone ready to build a more self-directed life close to Simpsonville. Please note the beehives do not convey with the sell of the property, and will be removed as soon as they can legally be moved.

621 Jenkins Bridge Road, Simpsonville

$874,900

4 Beds ⋅ 3.5 Baths ⋅ 1597384 MLS

NEW ROCKFORD PLAN by TRUST HOMES TAILORED! Mostly Full Brick Home with 3 Car Side Entry and Tandem Garage sits nestled on close to half acre home-site in cul de sac of established Simpsonville community! Entryway features formal living and dining room, connecting to Chef's Kitchen via Butler's Pantry and Large walk-in Pantry. Kitchen includes stainless built in gas appliances, vented wall hood, quartz countertops, tile backsplash, farm sink and 42" cabinets with crown moulding! Large family room with shiplap fireplace and built in bookshelves looks out onto covered patio! Primary Suite on main floor with large full tile walk in shower, large walk in closet, dual comfort height vanities and linen closet! Mud hall with built in bench and cubbies sits across from spacious walk in laundry with sink and additional storage cabinets. Walk up the hardwood tread staircase with open wrought iron spindles to upstairs loft, following 2 bedrooms with Jack and Jill bath set up, Media room, and a third bedroom with private bath access and walk in closet! Additional features include full in ground irrigation, upgraded light and plumbing fixtures, upgraded trim package, bronze color door hardware, and video door bell/smart switch tech package with structured wiring panel! Rare opportunity for new construction in an established community close to Holly Tree Country Club!

120 Lavender Hill Court, Simpsonville

$1,100,000

5 Beds ⋅ 4.5 Baths ⋅ 1597303 MLS

Don’t miss this rare opportunity to own a custom-built home on MORE THAN AN ACRE in the heart of FIVE FORKS with NO HOA! Built in 2020, this beautiful home sits on 1.26 acres, offers more than 4,500 square feet of thoughtfully designed living space – including 5 bedrooms, 4.5 bathrooms, a large open kitchen, and a FINISHED WALKOUT BASEMENT – and is zoned for award-winning Monarch Elementary School, Mauldin Middle, and Mauldin High. Inside, you'll find an open floor plan with site-finished hardwood floors throughout the main level. The kitchen is the heart of the home, featuring custom cabinetry, a large granite island with seating and storage, ample counter space, and a walk-in pantry. The kitchen flows seamlessly into the morning room and main living areas – perfect for everything from weeknight dinners to holiday gatherings. The main level has a designated OFFICE that could also serve as a den or playroom, as well as a side-entry MUDROOM for added convenience. The primary suite offers separate HIS-AND-HERS WALK-IN CLOSETS and a spa-like ensuite bath. Upstairs, you'll also find three additional bedrooms, two full bathrooms, the laundry room, and a flexible bonus space that works well as a playroom, homework area, or second living room. The basement features a large media room wired for surround sound, a full bathroom, a kitchenette and wet bar (complete with a sink, dishwasher, and two wall taps), two walk-in storage rooms – including one with a water line for a refrigerator or ice maker – and a private flex room that can serve as a fifth bedroom, guest suite, home gym, or craft room. The outdoor living spaces are just as impressive. Two screened porches overlook the peaceful, wooded backyard, complete with a creek, mature trees, and a pallet-sized brick fire pit. The patio is built for entertaining, with an OUTDOOR KITCHEN and a brand-new Blackstone griddle with natural gas connections. The yard has a full in-ground irrigation system with a dedicated water meter to keep water costs down, as well as a fenced-in area for pets, gardening, or play space. In addition to the ATTACHED TWO-CAR GARAGE, the property also includes a DETACHED TWO-CAR GARAGE with a full attic and a built-in workbench – ideal for hobbies, outdoor equipment, extra vehicles, or additional storage. This MOVE-IN READY home has been meticulously prepared for its next owners with new carpet, fresh interior paint, refreshed landscaping, and pressure washing – all completed in July 2026. If you’ve been searching for a spacious home on more than an acre with no HOA in the heart of Five Forks, you’ll want to see this one in person!

329 Brown Road, 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

136 Club Dr, Simpsonville

$1,695,000

4 Beds ⋅ 4 Baths ⋅ 1596927 MLS

There is only one lot left in Waterford at Roper Mountain—this is your final chance to get into this beautiful community! This to-be-built home offers an incredible single-level layout. It’s a true 4-bedroom, 4-bathroom home featuring a spacious, private primary suite alongside three additional bedrooms and a versatile flex space. The entire floor plan is designed around seamless indoor/outdoor living. You'll find an open concept that maximizes natural light and offers multiple spaces for entertaining. Step outside, and you'll enjoy a private outdoor living area overlooking a backyard specifically designed to accommodate a swimming pool and pool house. As with all homes in Waterford, the architectural and design standards are top-notch. Inside, the home is beautifully appointed with wide-plank hardwoods throughout, high-end appliances, and designer bathroom tile. The impressive exterior is just as thoughtful, built with high-quality materials that include a striking blend of natural stone, brick, genuine stucco, and natural wood. These are perfectly paired with cement board siding, board-formed concrete, modern metal accents, and premium aluminum-clad windows. If you've been waiting for the right opportunity in Waterford, this is it!

301 Waterford Fall Way, Simpsonville

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“ 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”

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