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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

$1,000,000
4 Beds ⋅ 4.5 Baths ⋅ 1596835 MLS
Welcome to 43 Appian Circle, nestled within the prestigious gated community of The Columns at Roper Mountain in the heart of Five Forks. This beautifully maintained 4-bedroom, 3 full bath, 2 half bath home offers a thoughtfully designed floor plan that blends timeless elegance with everyday comfort. Step inside to a stunning two-story foyer, where natural light pours through the home, highlighting the beautiful hardwood floors and creating an inviting first impression. Just off the entry, a private home office with elegant French doors provides the perfect space for working from home. Designed with both entertaining and everyday living in mind, the open-concept main level features spacious living and dining areas that flow seamlessly into the heart of the home. The main-level primary suite serves as a private oasis, complete with a cozy sitting area and direct access to the back patio. Upstairs, you'll find three generously sized bedrooms, two full bathrooms, and a versatile loft area. Two large attic walkouts offer easily accessible storage without the inconvenience of pull-down stairs. Outside, beautifully landscaped grounds create outstanding curb appeal, while the spacious 3-car garage provides plenty of room for vehicles and storage. Ideally located just minutes from Five Forks' premier shopping, dining, top-rated schools, and everyday conveniences, this exceptional home offers the perfect combination of luxury, functionality, and an unbeatable location within one of Simpsonville's most sought-after gated communities.

43 Appian Circle, Simpsonville
$950,000
1596732 MLS
Rare Simpsonville acreage offering with approximately 9.84 acres, zoned R-S, including two separate, noncontiguous tracts: a primary approx. 8.94-acre tract with League Road frontage plus a separate approx. 0.90-acre tract included in the sale. Level to gently sloping land offers a blend of open acreage and mature woods, providing an excellent setting for a custom estate home or mini-farm. Recorded covenants prohibit subdivision and mobile or modular homes. Horses and cattle are permitted on lots over five acres, subject to the recorded requirement of at least 2.5 contiguous pasture acres per horse or cow. Recorded minimum home sizes are 2,600 heated sq. ft. for one-story, split-level, and story-and-a-half homes; two-story homes require at least 1,500 heated sq. ft. on both the first and second floors. Cooper Ridge across the street is served by public water and sewer; however, availability, capacity, connection approvals, and cost for this property have not been verified. Buyer to verify all utilities, septic suitability, zoning, intended use, and restrictions. Convenient to Rudolph Gordon School (K-8), Fountain Inn High School, Carolina Springs Golf Club, CCNB Amphitheater at Heritage Park, and downtown Simpsonville and Fountain Inn.

00 Cooper Lake Road, Simpsonville
$2,400,000
5 Beds ⋅ 6.5 Baths ⋅ 1596210 MLS
Beyond the gate and winding drive, ROUX MANOR unfolds as a place of quiet beauty—where mornings begin with birdsong and evenings settle gently over open land and soft light. It’s not often you find a property that feels this private, this peaceful—and yet sits just minutes from everything Simpsonville and Greenville have to offer. Discover the beauty and serenity of this distinguished 7.46-acre estate where luxury meets country charm, tucked behind a private gated entrance and meticulously maintained to offer a rare blend of refined living, equestrian amenities, and resort-style outdoor spaces. Ideally located just off Highway 14 near Holly Tree Country Club and less than 20 minutes from Downtown Greenville, the setting feels worlds away while remaining remarkably convenient, with everyday essentials only minutes away. / THE GROUNDS & EQUESTRIAN FEATURES / A scenic, winding, tree-lined drive leads to the fully fenced estate adorned with mature landscaping, fruit trees, heirloom grape vines, and lush gardens. Designed for both enjoyment and function, the property includes a large barn with electric and a new roof, two gated pastures, a greenhouse with power and water, a chicken coop, and a freshly tilled garden ready for planting, with abundant wildlife including deer, foxes, hummingbirds, and pollinators drawn to the butterfly and herb gardens. / RESORT-STYLE POOL & GUEST HOUSE / The gunite pool, resurfaced in 2025 and complemented by a new pool pump a few months ago, offers a private escape, enhanced by a spa with water feature. A detached pool house and guest house, connected to the main home by a breezeway, provides a seamless extension for entertaining and everyday living, with an upper level featuring a spacious living area, bedroom, and full bath ideal for guests, a private office, or creative studio, while the three-car garage includes a large climate-controlled workshop and storage area. / THE MAIN HOUSE / Refined yet comfortable, the main residence showcases quality craftsmanship throughout with high ceilings, crown molding, plantation shutters, and five fireplaces. Italian hand-glazed diamond plaster walls add warmth and character, while a grand staircase and custom Turkish chandelier create a welcoming first impression. / GOURMET KITCHEN / Sub-Zero refrigerator, gas range, warming drawers, and a custom-built pantry. / PRIMARY SUITE / A private retreat with trey ceiling, double-sided fireplace, spa-inspired bath, expansive walk-in closet, and new skylights. / EXPANSIVE LIVING SPACES / Including a Florida Room, Study/Library, and Screened Porch overlooking the pool and grounds. / THIRD FLOOR FLEX SPACE / A large, versatile living area with kitchenette, multiple walk-in storage rooms, and a private balcony with sunset views. / MODERN UPDATES / New roof (2024), multiple HVAC systems all less than five years old, and updated electrical (2015). With no HOA, you’ll enjoy both privacy and flexibility. Priced below a recent appraisal, this estate presents a compelling opportunity for the next owner. Roux Manor offers a rare balance of elegance, functionality, freedom, and peaceful living—just minutes from everything Greenville has to offer. / Private tours available through the listing agent for qualified buyers. Additional details available upon request.

208 Holland Road, Simpsonville
$1,369,080
6 Beds ⋅ 4.5 Baths ⋅ 1596117 MLS
Welcome to 74 Modesto Lane in the Estate section of Coachman Plantation. Some homes are built. This one was finished, then thoughtfully refined year after year by an owner who truly loved living here. Situated on just over 2 private acres with approximately 6,776 finished sq ft on a private road, this exceptional home offers estate-style privacy with neighborhood amenities, surrounded by farmland, ample green space, and pastoral views. A two-story foyer welcomes you into a beautifully designed floor plan featuring formal dining and living spaces, a vaulted great room with gas fireplace, and a sunroom overlooking the backyard. The gourmet kitchen includes a Wolf gas cooktop with pot filler, Bosch dishwasher, wall oven/microwave, oversized island, custom bookshelves, and a flexible scullery space. The main-level primary suite offers a sitting area, private balcony, two walk-in closets, and spa-inspired bath with dual vanities, soaking tub, and tiled shower. Upstairs includes four additional bedrooms, a flex room, two full baths, and dedicated laundry room. The finished walk-out lower level provides incredible versatility with high ceilings, kitchenette, guest suite, full bath, entertainment space, and additional unfinished area ready for a theater, gym, golf simulator, wine room, or storage. Outdoor living features an expansive patio, elevated deck, hot tub, gas line for future outdoor kitchen/fireplace, full yard irrigation, oversized powered storage building, and a large flat backyard with room for a pool, sports court, or recreation space. Located in desirable Coachman Plantation with large lots, farmland views, neighborhood pool, playground, and community events. Convenient to Five Forks, Simpsonville, Fountain Inn, and Woodruff. Zoned for Rudolph Gordon and Fountain Inn High School. Schedule a showing to tour this beautiful home today!

74 Modesto Lane, Simpsonville
$850,000
7 Beds ⋅ 5 Baths ⋅ 1595617 MLS
Experience the pinnacle of luxury living in this extraordinary 5,000+ square foot retreat nestled in one of Simpsonville’s most desirable locations. Perfectly blending elegance, comfort, and entertainment, this stunning residence offers an exceptional lifestyle opportunity just minutes from Five Forks and a short drive to Downtown Greenville. Designed with both everyday living and unforgettable entertaining in mind, the home features expansive living spaces, multiple oversized bedrooms, and spa-inspired bathrooms throughout. The chef’s kitchen opens seamlessly into inviting gathering areas, creating the ideal setting for hosting family and friends in style. From the private cinema room and game room with pool table to the state-of-the-art fitness studio and designer hot tub, every detail has been thoughtfully curated to deliver a true resort-style experience. Step outside to enjoy the screened outdoor living space and commercial-grade grilling station overlooking the private setting — perfect for relaxing evenings, weekend cookouts, or enjoying South Carolina’s beautiful seasons year-round. The flexible floor plan offers tremendous versatility for multigenerational living, executive relocation, luxury second-home ownership, or even continued short-term rental potential. Ideally situated near premier shopping, dining, entertainment, and major thoroughfares, this one-of-a-kind property combines privacy, sophistication, and convenience in a way that is rarely available in today’s market. Luxury, space, and lifestyle converge here to create an exceptional opportunity unlike anything else in the Upstate.

2 Sheldrake Place, Simpsonville
$1,495,000
5 Beds ⋅ 4.5 Baths ⋅ 1595185 MLS
Nestled behind the gates of Cobblestone, one of Greenville’s most sought-after luxury communities, this exceptional 5BR/4.5BA custom residence offers timeless architecture, refined finishes, and an effortless blend of elegance and everyday livability. Originally featured on the Greenville Tour of Homes, 801 Brixton Circle showcases meticulous craftsmanship and thoughtfully designed living spaces throughout. A stunning stone entry welcomes you into a dramatic two-story foyer highlighted by rich hardwood flooring, extensive custom millwork, and an abundance of natural light. The private study features a coffered ceiling, fireplace, and built-in cabinetry, while the formal dining room is beautifully appointed with detailed trim work and wainscoting, creating an ideal setting for entertaining. The heart of the home is designed for gathering, anchored by a spacious great room with custom built-ins and a striking fireplace. The chef’s kitchen is both functional and impressive, featuring GE Monogram stainless appliances, double ovens, a gas cooktop, oversized island with prep sink, copper farmhouse sink, granite countertops, custom cabinetry, and generous workspace. Adjacent to the kitchen, the breathtaking keeping room showcases soaring cathedral ceilings and a dramatic two-story stone fireplace, creating a warm and inviting atmosphere. Seamlessly extending the living space outdoors, the expansive screened porch with coffered ceilings overlooks professionally landscaped grounds and a tranquil water feature, offering a private retreat for year-round enjoyment. The main-level owner's suite is a true sanctuary, featuring a tray ceiling, spa-inspired bath with dual vanities, and a spacious walk-in closet. A well-appointed laundry room and butler’s pantry complete the main floor. Upstairs, you'll find three generously sized bedrooms, each with excellent closet space and access to full baths, along with a versatile bonus room that can easily serve as a fifth bedroom, guest suite, media room, playroom, fitness space, or home theater. Residents of Cobblestone enjoy an outstanding amenity package including a clubhouse, resort-style pool, playground, and tennis courts, all within minutes of Five Forks' premier shopping, dining, and award-winning schools. Conveniently located between Greenville and Spartanburg with easy access to I-85, GSP International Airport, BMW, Michelin, and major healthcare campuses, this home offers the perfect combination of luxury, location, and lifestyle. A rare opportunity to own one of Five Forks' most distinguished residences.

801 Brixton Circle, Simpsonville
$2,500,000
4 Beds ⋅ 5.5 Baths ⋅ 1595183 MLS
**Welcome Home to 6 Peters Fork Ln** Nestled on over 1.3 pristine acres in the prestigious gated Kingsbridge community, this exceptional 4BR/5.5BA executive estate offers a rare combination of luxury, privacy, and resort-style living in the heart of Five Forks. A sweeping circular drive, meticulously manicured grounds, and timeless euro inspired architecture create an unforgettable first impression. Inside, soaring two-story ceilings elevate the newly renovated chef’s kitchen, where exquisite quartzite surfaces, premium appliances, custom cabinetry, and a dramatic designer range hood create a space as beautiful as it is functional. The kitchen opens seamlessly into a spectacular keeping room with vaulted ceilings, one of the home’s three fireplaces, and walls of windows overlooking the backyard oasis. The primary suite offers a private retreat with a spa-inspired bath and tranquil views, while additional bedrooms and living areas provide both comfort and flexibility for family and guests alike. Designed for both grand entertaining and everyday enjoyment, the home offers expansive living spaces, stunning architectural details, extensive custom millwork, elegant coffered ceilings, and luxurious finishes throughout. A dedicated media/theater room provides year-round entertainment, while four garage bays offer abundant space for vehicles, storage, and hobbies. 3 Bays on main level and a 4th in rear of home. Step outside to your own private resort. The expansive covered veranda, screened in porch and All Seasons Sun Room, complete with additional fireplace and inviting gathering spaces, overlooks a beautifully designed saltwater pool and spa framed by mature landscaping and exceptional privacy. A separate pavilion creates the perfect setting for outdoor entertaining, while thoughtful amenities such as an outdoor bathroom and outdoor shower make poolside living effortless for family and guests alike. As the sun sets, enjoy evenings around the fire, unwind beneath the glow of the covered porch, or simply take in the serenity of this remarkable property. Every detail has been carefully curated to create a home that is both elegant and comfortable, sophisticated yet welcoming. Located within one of Greenville’s most coveted gated neighborhoods, 6 Peters Fork Lane offers an extraordinary lifestyle defined by privacy, prestige, and convenience—just minutes from shopping, dining, award-winning schools, GSP International Airport, both interstates, and everything Five Forks has to offer. Featuring a newly renovated kitchen, three fireplaces, media/theater room, four-car garage, resort-style saltwater pool, outdoor bath and shower, and over an acre of beautifully landscaped grounds, this is luxury living at its finest in Kingsbridge.

6 Peters Fork Lane, Simpsonville
$3,299,681
5 Beds ⋅ 6.5 Baths ⋅ 1595115 MLS
For the owners of 115 Anna’s Place, their nearly 25 years with the property have made them feel that they have lived on a mini estate. This property consists of nearly 2.5 acres, a house setback from a quiet cul-de-sac with a huge front lawn, hills for sledding and woods to play and explore. There is also the additional benefit of neighborhood living with access to community amenities and connection to neighbors. This property was purchased, designed and built by the current owners. As one tours the home, the attention to detail, quality and luxury is apparent. Custom cabinetry, custom light fixtures, solid doors, a four car garage with room for four large vehicles and storage, exquisite first floor moldings, Pennsylvania bluestone patio and so much more. While this house was designed for a young family, it can be utilized at any stage of life and the property size allows for expansion.(1.5 acre home site plus adjoining 1 acre lot). The interior of the home with nearly 9600 ft.² has space for everything you need and room for any hobby or activity. Beyond the luxury features, this home was also built with function in mind- 2 washer/dryer hookups, two dishwashers, two first floor powder rooms. Design, function, space, privacy, size and versatility this property has it all.

115 Anna's Place, Simpsonville
$850,000
5 Beds ⋅ 3.5 Baths ⋅ 1595025 MLS
Welcome to 204 Parkside Drive, nestled in the highly sought-after River Walk neighborhood. This exceptional home offers over 4000 square feet, five bedrooms, three and half bathrooms, flex room, and a primary suite along with an additional guest bedroom on the main level providing ideal flexibility for multi-generational living or visiting guests. A dramatic two-story foyer makes a striking first impression, filled with abundant natural light and anchored by a glass front door and wrought iron spindle staircase that sets the tone for the home’s refined aesthetic. The heart of the home is the stunning renovated kitchen is both elegant and highly functional. Showcasing marble countertops, an oversized entertaining island, farmhouse stainless steel sink, hidden storage underneath, prepping island with sink, built-in wine rack, exposed brick backsplash, gas cooktop, wall oven, microwave, trash compactor, soft-close drawers, an abundance of cabinetry and built- in desk. A dedicated breakfast room with custom built in cabinetry adds charm and practicality, creating a seamless space for casual dining and additional storage. The impressive Great Room serves as a stunning focal point, featuring a vaulted ceiling, recessed lighting, wall sconces, and an elegant marble gas log fireplace that anchors the space with warmth and sophistication. The spacious dining room is right off the foyer which is currently served as a music room. The primary suite is on the main level and boasts double trey ceiling, double sided gas log fireplace creates a warm, inviting ambiance, enjoyed from both the bedroom and spa inspired bath while soaking in the jetted tub. The ensuite features tile flooring, dual vanity, separate shower, water closet, enormous walk-in closet with custom built-in cabinetry creates the perfect sanctuary at the end of the day. A main-level bedroom with adjacent full hall bathroom offers exceptional versatility and is currently used as a home office but has previously been used as a nursery and guest bedroom, making it ideal for a variety of lifestyle needs. Rounding out the main level is a powder room, laundry room with cabinetry, hanging area and utility sink. Perfect drop-zone area with bench, hooks and cubbies right when you walk in from the garage. The second level offers three spacious bedrooms, each featuring their own walk-in closet, along with a Jack-and Jill bathroom. A flex room provides additional living space, ideal as a playroom, media room, or game room. Additional storage is thoughtfully provided with a walk-in floored attic and a separate pull-down attic. This floor plan offers so much flexibility for entertaining family and friends. Plus, inside there are plenty of closets and storage areas designed to keep you organized and efficient. Designed for effortless indoor – outdoor living, the screened porch is a standout addition with handsome tongue and grove ceiling, grilling deck, beautifully designed stone patio with stone firepit, creating the perfect setting for relaxing evenings and year-round entertaining. Wanting to take an after-dinner stroll or the kids want to ride their bikes, you are in luck, the path is right in your backyard! The sellers have made many improvements to their home ~ kitchen remodel, breakfast room custom cabinetry hutch, added screen porch with tongue and groove ceiling, new roof, hot water tank, electric fence for your pets, outdoor automatic lighting, lighting throughout the home, alarm system, planted numerous trees and bushes and painted. River Walk offers exceptional resort style amenities including clubhouse, exercise facility, swimming pool with active swim team, tennis and pickleball courts, playground, walking trails, recreational paths, common green spaces, and sidewalks throughout much of the neighborhood. Nature enthusiasts will appreciate more than four miles of picturesque recreational pathways winding through wooded landscapes and along with scenic Creekside views!

204 Parkside Drive, Simpsonville
$1,150,000
4 Beds ⋅ 3.5 Baths ⋅ 1594490 MLS
Welcome to this exceptional all-brick home located on a sprawling 1.2-acre level lot in the highly sought-after Kilgore Plantation community. Offering generous living spaces, and endless potential, this home is ready for its next owner to make it their own. Step inside the impressive two-story foyer, flanked by a versatile office, living room, or music room on one side and a gracious formal dining room with classic chair rail detailing on the other. The dining room flows through a convenient butler’s pantry area into the expansive kitchen, featuring a center island, tile backsplash, built-in desk, abundant cabinetry, and a sunny breakfast area overlooking the private backyard. A French door provides easy access to the brick patio, creating a seamless indoor-outdoor lifestyle. The spacious great room is the heart of the home, showcasing custom built-in bookcases with a wet bar, a cozy fireplace, and a wall of windows and French doors that open to the expansive screened porch—perfect for relaxing, entertaining, or enjoying views of the backyard. Upstairs, the large primary suite serves as a true retreat with a trey ceiling, fireplace, and built-in desk area. The en-suite bath offers dual vanities, a jetted tub, tiled shower, and generous closet space. Three additional oversized bedrooms provide plenty of room for family and guests, including one with a private bath and two connected by a Jack-and-Jill bathroom. A huge bonus room with closet and walk-in attic storage adds incredible flexibility for a media room, playroom, home gym, or guest space. Additional highlights include gleaming hardwood floors, plantation shutters, a circular driveway, attic fan, two water heaters (including one tankless),mature landscaping and ample garage storage. Rarely does a home offering this combination of space, character, and premier location become available. Don't miss the opportunity to make this Kilgore Plantation home your own.

230 Kilgore Circle, Simpsonville
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