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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

$950,000
5 Beds ⋅ 4 Baths ⋅ 1593172 MLS
Located in the heart of sought-after Five Forks in the prestigious Upland Farms community, this exceptional 5-bedroom, 4-bath Craftsman residence sits on a beautifully landscaped private half-acre homesite and showcases more than $200,000 in luxury enhancements completed after construction. Thoughtfully redesigned with high-end finishes and custom craftsmanship throughout, this home offers the perfect blend of elegance, comfort, and functional living. –From the moment you arrive, the inviting front porch with custom tongue-and-groove wood ceiling sets the tone for the impressive interior. Inside, extensive upgrades include plantation shutters throughout, all new lighting and plumbing fixtures, upgraded flooring, designer trim work, custom wainscoting, shiplap accents, beadboard details, and natural wood ceiling beams. –The open-concept main living area was designed for entertaining, featuring a dramatic stacked stone accent wall, custom wood archways, beadboard ceiling detail, soaring ceilings, and seamless flow into the fully upgraded chef’s kitchen. The kitchen boasts quartz countertops, an enlarged island, farmhouse sink, gas cooktop, stainless steel appliances, designer tile backsplash, pot filler, wood beam accents, and a spacious walk-in pantry. The spacious floorplan also includes a formal dining room, private office/study, oversized loft, and an incredible media/flex room complete with wet bar and beverage refrigerator. –The breakfast area opens to a stunning screened porch with natural wood ceilings, creating an ideal indoor-outdoor living experience. Beyond the porch, enjoy a custom stamped concrete patio, hot tub, gazebo, extensive landscaping, Bermuda sod, and custom exterior lighting for a private backyard retreat with added privacy from surrounding natural space. –A guest suite with a beautifully renovated full bath is conveniently located on the main level. Upstairs, the owner’s suite has been transformed into a luxurious sanctuary featuring hardwood flooring, a custom gas fireplace, oversized custom closets, and a spa-inspired bath with designer tile, marble countertops, farmhouse-style vanities, clawfoot tub, and an expanded walk-in shower. –Secondary bedrooms offer custom closets and updated baths, including a remodeled Jack-and-Jill bath with a newly added walk-in tiled shower. Additional features include a two-story foyer, side-entry garage, security system with cameras, extensive custom millwork, and countless designer touches rarely found in newer construction. Conveniently located near Five Forks shopping, dining, and award-winning schools, this move-in ready home delivers luxury living with unmatched attention to detail.

12 Peyton Lane, Simpsonville
$1,450,000
4 Beds ⋅ 4.5 Baths ⋅ 1592909 MLS
There are houses… and then there is that special place that truly feels like HOME. Set on a beautifully level 1.69-acre lot, this property offers the kind of lifestyle most people only experience on vacation. From peaceful mornings on the front porch with a rocking chair and coffee, to evenings gathered under the covered back porch overlooking the pool, every space invites you to slow down, relax, and enjoy life a little more. The backyard is truly something special — expansive, manicured, and designed for making memories. Whether it’s hosting a family reunion, a holiday gathering, a wedding celebration, or simply enjoying a quiet evening with the people you love most, this property was made for togetherness. The gunite pool, pool house with kitchen and lounge area, and incredible outdoor living spaces create the perfect backdrop for entertaining on any scale. At the end of the day, the current owners’ favorite tradition is simple: sitting on the covered porch, sharing dinner, talking about their day, and taking in the beauty of another southern evening. It’s easy to imagine doing the very same thing here. Practicality meets comfort as well, with garage parking for 5 vehicles along with ample additional parking for guests. And throughout the home, you’ll find thoughtful updates and loving improvements that reflect the care this property has received over the years. Be sure to ask us — or your Realtor — for the complete list of features, updates, and improvements. Also, because some websites do not support 3D tours, please reach out directly for the tour link so you can experience this home from anywhere in the world. Some homes simply check boxes. Others create a feeling the moment you arrive. This is one you truly need to experience in person. We invite you to come visit and see what makes this property feel so much like HOME. Call us, or your Realtor, to schedule a tour today! (NOTE: Because some sites do not allow the 3D tour, please ask us or your Realtor to send you the link.)

2383 Roper Mountain Road, Simpsonville
$2,350,000
5 Beds ⋅ 4.5 Baths ⋅ 1592426 MLS
Back on Market at no fault of sellers. Welcome to 305 Chancery Lane, an extraordinary custom-built residence nestled behind the gates of Cobblestone, one of Five Forks’ most coveted luxury communities. From the moment you arrive, it’s clear that no detail has been overlooked and no expense spared in transforming this home into a true indoor-outdoor oasis. Spanning over 5,000 square feet, this thoughtfully designed home offers the ease of main-floor living with five bedrooms, four and a half baths, and a three-car garage. Soaring 10-foot ceilings flow throughout, lending every space an open, airy elegance. This residence features a formal living room, a formal dining room, a great room that is completely open to a show-stopping chef’s kitchen appointed with a Wolf gas cooktop, Sub-Zero refrigerator, dual prep sinks, an oversized island, a breakfast area, and a generous walk-in pantry — everything a serious cook or effortless entertainer could desire. The oversized primary suite is a true retreat, complete with dual walk-in closets, a dedicated home office space, and a gorgeous, fully remodeled en suite bath including a freestanding soaking tub and a new sauna. Three additional spacious bedrooms — each with their own walk-in closet — provide comfort and privacy for family and guests alike. Tucked seamlessly in the hallway of the home is a custom built-in workspace with cabinetry and shelving, perfect for an extra office or kids homework/craft station. Upstairs, a personalized home theater outfitted with a brand-new Sony high-definition projector and plush reclining seats, plus a fifth bedroom (or flex space) and another full bath, round out the living experience perfectly. Step outside and prepare to be wowed! The outdoor living space is nothing short of spectacular, centering on a saltwater pool and hot tub with a Baja shelf — ideal for soaking up those warm Carolina days. A completely renovated outdoor kitchen and covered fireplace area with seating create the ultimate alfresco entertaining zone, while beyond the pool privacy gate, a level private backyard offers open green space with plenty of room to play. Family nights just got an upgrade! The sellers have executed a comprehensive, top-to-bottom renovation that includes a brand new architectural roof, all new seamless gutters, whole-house exterior paint, full house window replacement, all new insulated garage doors plus new motor/track, new epoxy garage flooring, new HVAC and heat pump, 2 new tankless gas water heaters, new alarm and AV upgrades throughout, new kitchen appliances, new central vacuum, a complete landscape redesign with landscape lighting, and a newly resurfaced pool patio featuring a cooling, slip-resistant finish. The list of upgrades is simply too extensive to capture here — this is truly a must-see in person. All of this is perfectly positioned in the heart of Five Forks, just minutes from premier shopping, acclaimed restaurants, top-rated schools, and the Greenville-Spartanburg Airport. Cobblestone residents enjoy exclusive access to a clubhouse, pool, tennis courts, and playground — a lifestyle that matches every square foot of this remarkable home. This is more than a home. It’s the one you’ve been waiting for. Schedule your private showing today.

305 Chancery Lane, Simpsonville
$1,420,000
5 Beds ⋅ 5 Baths ⋅ 337070 MLS
Welcome to a rare blend of elegance, space, and privacy at 646 Harrison Bridge Road in Simpsonville. Nestled on nearly 2 acres of beautifully maintained grounds, this stunning brick estate offers the perfect balance of refined living and everyday comfort. From the moment you arrive, the exceptional landscaping and stately curb appeal set the tone for what awaits inside. This expansive home features 5 spacious bedrooms and 4.5 baths, thoughtfully designed to provide both luxury and functionality. The interior boasts generous living spaces filled with natural light, ideal for both entertaining and quiet evenings at home. The fully finished basement offers incredible versatility—perfect for a media room, home gym, guest suite, or all of the above. Step outside and discover your own private retreat: a sparkling pool surrounded by lush greenery, creating a resort-style atmosphere right in your backyard. Car enthusiasts, hobbyists, or those in need of extra storage will appreciate the large detached, climate control, garage, offering ample space beyond the main home. This garage has the capacity to possibly hold 8 cars. Every detail of this property has been carefully curated to provide a sense of comfort, sophistication, and room to breathe. If you’ve been searching for a home that combines luxury living with acreage and privacy—while still being conveniently located near everything Simpsonville has to offer—this is the one.

646 Harrison Bridge Rd, Simpsonville
$1,250,000
4 Beds ⋅ 3.5 Baths ⋅ 1591414 MLS
Welcome to 109 West Curtis Street where you will find the definition of charm and character living in this classic and beautifully restored 1885 home in the heart of the thriving and vibrant city of Simpsonville SC!!! You can walk to everything including all the shopping and restaurants this amazing city has to offer from this truly exceptional home which is the most historic house, in Downtown Simpsonville! From the moment you see the inviting curb appeal of this completely renovated inside and out home on this large corner lot in this prominent location! You will fall in love with everything you see to include the incredible grounds that have been completely upgraded from corner to corner and include large hardwoods, beautiful fescue, exterior lighting, full irrigation, powder coated steel fence, multiple exterior patios and porches, a side entry two-car carport with brick and concrete accents, an exterior dining area, a large covered porch which is perfect for evening cocktails or morning coffee overlooking the large custom bluestone grilling area which all stays to include smoker and built-in grill, your own heated and cooled studio or guest house opportunity which is renovated and has multiple sliding doors for ample natural light, and even a water feature for a Koi pond. As you enter the home you will immediately fall in love with the character of yesteryear, but you will appreciate all the amenities we have come to expect! The flow is perfect for entertaining friends and family throughout the seasons, and comes complete with a large entry foyer with detailed tiled ceilings, a large open living room with gas log fireplace, a large dining room with classic fireplace mantle, a fully renovated kitchen with marble custom tile backsplash to the ceiling, a beautiful tongue and groove bead board ceiling, a Jennair double oven with six gas burner and griddle with a marble backsplash, pot filler and commercial grade hood, beverage center and refrigerator. Additionally, on the main floor, you will find a renovated powder room and the large master suite complete with a classic fireplace with brick surround and mantle, built-ins, a floating tub, double vanity, wonderful closet space as well as a private toilet and walk-in shower complete with glass door and full tiled walls with seat, niche and multi-Jets! Upstairs you will find a friendly family floor plan with three large bedrooms, a fully renovated full hall bath, a brand new additional third full bathroom with double sinks and walk-in-tiled shower, extra storage space and beautiful pine floors throughout the upstairs area! Additional features of this incredible home are fresh paint throughout, all new windows, canned lighting and new light fixtures, beautiful hardwood floors throughout entire home, a large main level laundry room that doubles as a "drop zone" with a private owner's rear side entrance, full alarm system, this list goes on and on and you will not be disappointed upon your private tour so come see for yourself today!!! New owner possibilities include some zoning opportunity if you want a work/live type set up, inquire within the city because there are options with this zoning of this home in this location, so this truly is an opportunity like no other!

109 W Curtis Street, Simpsonville
$1,465,000
5 Beds ⋅ 4.5 Baths ⋅ 1590288 MLS
Set along the water in the gated community of Chestnut Pond, 201 Chestnut Pond Lane blends European-inspired design with a setting that feels both private and connected. With a stone exterior and timeless architectural presence, the home sits on a pond lot with sidewalks and neighborhood lake access—offering a lifestyle that naturally extends outdoors. Inside, the main level is defined by its sense of scale and light. The living room features vaulted ceilings that create an airy yet refined feel, anchoring the space and seamlessly connecting to the kitchen. Designed for both everyday living and entertaining, the kitchen is anchored by a gas cooktop and wall oven, complemented by a spacious walk-in pantry and a layout that supports both function and flow. With five bedrooms and four-and-a-half baths, the layout offers flexibility to suit a variety of needs, including dual primary suites. The main primary retreat is complemented by a spa-like bath designed for comfort and quiet luxury, while finishes throughout—hardwood floors, ceramic tile, and carefully selected details—add warmth and polish. The lower level expands the home’s livability with a fully finished basement complete with its own kitchen/kitchenette and separate entrance, creating an ideal space for guests, extended stays, or recreation. Outdoors, the experience continues with intention. A spacious screened porch overlooks the water, while the in-ground pool and patio create a true retreat for relaxing or entertaining. The setting balances natural beauty with thoughtfully designed outdoor living, making it easy to enjoy every season. Built in 2021 by Woodland Custom Homes, this residence provides a seamless blend of elevated design, flexible living spaces, and a serene waterfront setting within one of Simpsonville’s most desirable gated communities.

201 Chestnut Pond Lane, Simpsonville
$924,900
4 Beds ⋅ 4 Baths ⋅ 1590164 MLS
Welcome to 102 Braxton Meadow Drive in the heart of Simpsonville — a stunning custom residence built by renowned Arthur Rutenberg Homes offering luxury living, timeless design, and over 3,400 square feet of beautifully crafted heated and cooled space. This exceptional 4 bedroom, 4 full bath home blends elegance, comfort, and thoughtful functionality in every detail. Your future begins the moment you step onto the inviting 21x7 rocking chair front porch — the perfect place for morning coffee, evening conversations, and Southern living at its finest. Inside, you’ll immediately appreciate the incredible flow and open design featuring a spectacular 26x15 great room that seamlessly connects to the expansive 20x16 gourmet kitchen and spacious 16x9 dining area, creating an ideal setting for entertaining and everyday living. The chef’s kitchen is truly the heart of the home, showcasing custom cabinetry, upgraded stainless steel appliances, a gas cooktop, oversized gathering island, and a hidden walk-in pantry that adds both charm and convenience. Whether hosting friends or preparing a quiet dinner at home, this space was designed to impress. One of the most remarkable features of this home is the incredible indoor/outdoor living space on the back porch. Enclosed with Andersen windows and fully heated and cooled, this all-season retreat allows you to enjoy the beauty of every season in complete comfort — perfect for relaxing, entertaining, or simply taking in the peaceful backyard setting year-round. Retreat to the spa-inspired primary suite on the main level, where luxury and relaxation meet. The ensuite bath features a gorgeous tiled shower, freestanding garden tub, separate vanities, and an oversized walk-in closet designed to accommodate every need. A secondary bedroom and full bath on the main floor provide flexibility for guests, office space, or multi-generational living. This main level offers a beautiful office at the front of the home for the work-at-home professional and an oversized laundry room complete with granite countertops and abundant cabinetry— proving that even functional spaces in this home were designed with elegance in mind. Don't miss the remote control Hunter Douglas blinds that grace the windows along the back of the home. Spectacular! Gorgeous hardwood floors guide you throughout the main living areas of the home and up the elegant rounded staircase to the second level, where you’ll find two additional bedrooms — including one with a private ensuite bath — plus another spacious full hall bath. A large bonus room offers endless flexibility and could easily serve as a media room, craft space, playroom, home gym, or even a fifth bedroom if desired. Situated on over one-third of an acre, the fenced backyard is beautifully landscaped and offers both privacy and room to enjoy outdoor living. Make sure your clients see the amazing attic space upstairs. The long driveway provides ample parking for guests, while the oversized side-entry two-car garage adds convenience and curb appeal. 102 Braxton Meadow has a whole house generator for the times when you need it the most. This extraordinary home combines luxury finishes, exceptional craftsmanship, and sophisticated design in one unforgettable property. Minutes from Publix, Lowes, Sprouts, Target, and of course, GSP airport. Don’t miss your opportunity to own this remarkable home in one of Simpsonville’s most desirable locations.

102 Braxton Meadow Drive, Simpsonville
$1,420,000
5 Beds ⋅ 4.5 Baths ⋅ 1589938 MLS
Welcome to a rare blend of elegance, space, and privacy at 646 Harrison Bridge Road in Simpsonville. Nestled on nearly 2 acres of beautifully maintained grounds, this stunning brick estate offers the perfect balance of refined living and everyday comfort. From the moment you arrive, the exceptional landscaping and stately curb appeal set the tone for what awaits inside. This expansive home features 5 spacious bedrooms and 4.5 baths, thoughtfully designed to provide both luxury and functionality. The interior boasts generous living spaces filled with natural light, ideal for both entertaining and quiet evenings at home. The fully finished basement offers incredible versatility—perfect for a media room, home gym, guest suite, or all of the above. Step outside and discover your own private retreat: a sparkling pool surrounded by lush landscaping, and a beautiful fire pit area creating a resort-style atmosphere right in your backyard. Car enthusiasts, hobbyists, or those in need of extra storage will appreciate the large detached, climate control, garage, offering ample space beyond the main home. This garage has the capacity to possibly hold 8 cars. Every detail of this property has been carefully curated to provide a sense of comfort, sophistication, and room to breathe. If you’ve been searching for a home that combines luxury living with acreage and privacy—while still being conveniently located near everything Simpsonville has to offer—this is the one.

646 Harrison Bridge Road, Simpsonville
$960,000
4 Beds ⋅ 3 Baths ⋅ 1588982 MLS
Build your custom dream home on this level, partially wooden lot in the highly sought after Simpsonville community! This to be built home features 4 bedrooms, 3 full baths with tons of living and storage space. Gorgeous finishes and lighting will add to the high end appeal of this home. A few exterior features include Hardie board plank on front exterior, Hardie lap siding on sides and back, exterior paint by Sherwin Williams, architectural shingles roofing, aluminum black gutters, fiberglass exterior front door, and vinyl windows. The lot will be fully sodded with Bermuda grass. A few interior features include custom tiled showers, custom cabinets, quartz countertops, batt insulation in walls and blown insulation in attic, and an electrical fireplace. The builder will also provide an appliance allowance. Situated among the trees, off on Highway 14 in Simpsonville, this location is close to entertainment, dining, and interstates!

630 Highway 14, Simpsonville
$1,299,000
5 Beds ⋅ 4 Baths ⋅ 1588790 MLS
Are you looking for a NO HOA ,BIG YARD AT A GREAT LOCATION?? This is it for you !! Located in the sought-after Roper Mountain Road area, this Tudor/European-style with CUSTOM BUILT AESTHETIC 5 Bed /4 Bath home offers space, privacy, and luxury resort-style living on approximately 0.80 acres with no HOA. Gate-style grandiose entrance with long private driveway. Features include spacious kitchen, sunroom, primary (master) suite, and dedicated laundry room, plus flexible home theater or in-law suite. Outdoor amenities include a courtyard and in-ground pool, ideal for entertaining. New HVAC and solar panels in place. Convenient to shopping, dining, and major roadways, just minutes to Greenville. Zoned for top-rated schools.

1311 Moore Road, Simpsonville
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