Simpsonville Properties over $2,000,000 for Sale

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Newest Simpsonville Properties over $2,000,000 for Sale

$2,400,000

5 Beds ⋅ 6.5 Baths

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

$3,299,681

5 Beds ⋅ 6.5 Baths

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

$2,350,000

5 Beds ⋅ 4.5 Baths

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

$2,975,000

5 Beds ⋅ 6.5 Baths

Welcome to one of Cobblestone’s most exceptional offerings— 704 Brixton Circle- where timeless architecture, refined craftsmanship, and resort-style living converge in a truly unforgettable park like setting. The custom 5BR/5.5BA estate immediately captivates with its striking stone and brick façade and commanding presence. This home simply sprawls across the 1.5 acre creekfront homesite, nestled among mature trees, & beautifully curated landscaping all tiered down to the fire pit and creek via the natural stone retaining walls and stairs! Entering through the European courtyard you are immediately greeted by a grand two-story foyer with a sweeping staircase that sets the homes tone—elegant, warm, and effortlessly sophisticated. Thoughtfully designed for both everyday living and elevated entertaining, the main level unfolds with gracious living spaces, rich hardwoods, detailed millwork, and soaring ceilings that invite natural light throughout. The great room is a showpiece, anchored by exposed beams and a stately fireplace, while walls of windows frame serene views of the surrounding landscape. The kitchen is as functional as it is beautiful—featuring custom cabinetry, a substantial center island, high-end appliances, and seamless flow into inviting gathering spaces. From intimate dinners to large-scale entertaining, every detail has been carefully considered. 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. The lower level is a destination all its own—designed for both entertaining and retreat. A private, richly appointed pub-style lounge, is the perfect spot for hosting a wine tasting. Enjoy evenings around the billiards table, gather for cards, or unwind in the dedicated fitness room. An additional private suite on this level offers ideal accommodations for guests or multigenerational living, all wrapped in the same elevated finishes found throughout the home. Step outside and experience a setting that rivals a private resort. Expansive terraces, covered outdoor living spaces, outdoor kitchen, and multiple entertaining areas overlook a picturesque, park-like backyard complete with a firepit gathering space and lush natural surroundings. Every inch of this home reflects intentional design, quality craftsmanship, and a level of care rarely found. Hidden within the gates of one of the Upstate’s most sought-after communities, this is more than a home—it’s a lifestyle. The Five Forks location is just minutes away from great restaurants, shopping, entertainment, great schools, major highways & GSP International Airport, making it the perfect abode for those who demand the very best in luxury and convenience.

704 Brixton Circle, Simpsonville

$2,499,900

5 Beds ⋅ 5.5 Baths

Surrounded by 4.5 acres of peaceful countryside, 602 Jenkins Bridge offers next level design, serious fun, and will wow even the most discerning of buyers. It is a MUST see! Around every corner is an intentional effort to maximize functionality, enjoy hosting, and live comfortably- inside and out. Beyond the home itself, the location is something truly special. While the setting feels quiet and tucked away, it is only 5 minutes from shopping, restaurants, and groceries at Fairview Rd. with CityScape Winery, Happy Cow Creamery, and interstate access nearby. It is only 25 minutes from downtown Greenville and the GSP airport. The outdoor living spaces define this property. A custom gunite zero-entry saltwater pool and spa is complemented by a turfed four hole putting green, outdoor kitchen, fireplace, and fire pit. A second level porch overlooks it all, creating an ideal setting for both quiet evenings and large gatherings. With a half bath and second refrigerator just inside, no detail was spared in the functionality of the outdoor space. The current owners expanded the property by an additional acre and a half, adding to the serenity and feel of privacy and the ability to tap into a natural water source. Inside, the home opens with a spacious foyer and soaring ceilings. Wood beams warm the open living areas and the stone fireplace creates architectural character. The kitchen is appointed with a full size Electrolux refrigerator and freezer, custom floating shelving, updated hardware, new lighting, and a new range hood. In the living room, built in shelving adds scale and makes an impressive visual impact. The main level primary suite is conveniently located, with generous closet space and an adjoining small office. A well designed laundry room off the garage provides excellent storage and makes a useful “drop zone.” Upstairs, two oversized bedrooms- both just over 400 sqft- share the level with the fourth bedroom. Two full bathrooms and an additional sitting area complete the upper level. The options for how to use these spaces are endless. 3 bedrooms? Homeschool room? Playroom? Craft space? More office space? Guest room? You can truly have your pick. The lower level delivers nearly 2,500 square feet of finished space designed for both work and play. A dedicated office or optional fifth bedroom is paired with its own full bathroom. Additional highlights include a home gym with its own garage door, a wet bar with beverage refrigerator, a media room, and ample storage, including a locked cedar closet. A climbing wall, foam pit, and playhouse offer memorable play spaces- kids will never want to leave! The home has been professionally decorated. For those who appreciate it just as it’s styled, nearly all of the furnishings are available to be purchased alongside the home- allowing for a seamless, move-right-in experience. It is truly BETTER than new. This home has received numerous updates throughout over the past 6 months. Improvements include all new carpeting, refinished hardwood floors on the main level, engineered hardwood flooring on the lower level, a new roof installed in 2025, and a whole home water filtration system. Additional updates and improvements are available in the associated documents-there are too many to list.

602 Jenkins Bridge Road, Simpsonville

$2,500,000

Tax Id 0566.02-01-010.09 and 0566.02-01-010.03 are part of this sale. 109 and 113 Hipps Rd. Sewer, Water, and Gas are available. Great location for single family or multiple family subdivision.

109 Hipps Road, Simpsonville

$4,750,000

15 plus acres located on Harrison Bridge Road. This property would be great for any commercial property your client would want. Close to all corridors and shopping and restaurants of Fairview Road. Tax ID 0566.02-01-010.00 and TAX ID 0566.02-01-010.06 are both included in sale

602 Harrison Bridge Road, 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