Welcome to Oakleaf, an iconic Greenville estate where timeless architecture and modern luxury come together across approximately three private, beautifully landscaped acres in the heart of downtown Greenville. Surrounded by majestic mature oaks, towering magnolias, and curated gardens, the property provides an incredibly rare sense of seclusion with an established and refined presence. Originally rooted in the 1920s and featured in publications and tours over the years, the home has been thoughtfully reimagined for today’s lifestyle while honoring its architectural heritage. Several recent updates and modernized touches throughout add to the ease of living behind its enduring craftsmanship. With over 9300 total square feet of livable space between the main residence, a charming carriage house attached to the garage, and the fully redesigned guest house; there are very few needs and desires your lifestyle may demand that cannot be fulfilled within the private sanctuary of 22 Bennett St. The main residence, spanning over 6500 square feet on its own, reflects an elegant English manor influence with five bedrooms and six-and-a-half baths. A stunning main-level primary suite introduces a more contemporary layer, with vaulted ceilings, expansive windows, and direct access to a private garden terrace. The 14 x 22' primary bath features marble finishes, dual vanities, a free-standing soaking tub, glass-enclosed shower, custom his and her closets, and his and her water closets. Designed with both everyday living and entertaining in mind, the home provides gracious formal spaces alongside a well-appointed chef’s kitchen, expansive center island, and inviting gathering areas that flow seamlessly throughout. A richly detailed den, wine cellar with original brick accents, and flexible spaces for work or leisure further enhance the experience. Complementing the main home, the separate guest house and carriage house provide exceptional accommodations for extended stays, providing both privacy and flexibility for hosting. With seven bedrooms and nine-and-a-half baths across the property, the estate is uniquely suited for multigenerational living or a true retreat-like setting. Winding brick walkways, manicured courtyards, and layered outdoor spaces create an atmosphere that feels both intimate and expansive—ideal for gatherings, quiet moments, and everything in between. A rare opportunity to own a legacy property in one of Greenville’s most coveted settings, designed to live beautifully now, while carrying its story forward for generations to come. Some images have been virtually staged.

First time ever offered on the market. Stunning custom built English Cottage in the heart of Alta Vista!

This brand new 4, 300sf, downtown luxury condo overlooks the waterfall and green space of Rock Quarry Garden, and is just steps from the Swamp Rabbit Trail, Cleveland Park and Liberty Falls. The location is unmatched in downtown Greenville. The quartzite kitchen and dedicated scullery are built for serious cooking: GE Monogram appliances including a 48" dual fuel range, two dishwashers, a 60" paneled refrigerator/freezer, wine cooler, and speed oven, with extensive pantry storage throughout. Ten-foot ceilings, European white oak floors (zero carpet), inset cabinetry and millwork, Sonance invisible speakers, and 8-foot solid core doors set the tone throughout. Large Sierra Pacific windows bring the natural setting inside at every turn, and and robust sound-deadening systems have been installed between the two units, providing a quiet, private, home. The primary suite is a sanctuary unto itself — 12-foot ceilings, a fireplace, heated marble floors, zero-entry steam shower, soaking tub, towel warming drawer, a custom imported solid marble vanity, and a custom walk-in closet with private washer/dryer connection. All three bedrooms are en suite. Downsize without compromise. Lock-and-leave luxury, park-side living, and the best of downtown Greenville just steps away. SOLD COMPS: 103 Cleveland St #401, 103 Cleveland St #402, 355 S Main #1204, 355 S Main #1102

BRAND NEW MASTERPIECE, ready to call your own by July. Walk to Augusta Circle, 5 minutes to PRISMA, and to Downtown GVL. Replete with features you crave: 6 car attached garage, 10 ft ceilings on main, 9 ft up, vaulted ceilings, 2 porches, 4 fireplaces, site finished hardwoods, Icynene insulation, walk-in wine cellar, home gym, home theater, Rec Room, THREE LAUNDRIES, the list goes on. Center attraction: Chef's Kiss open quartzite kitchen with gas cooking, top of the line appliances - PLUS SCULLERY & walk-in pantry. Primary suite TO DIE FOR on main. ALL bedrooms en suite - including In-Law/Au Paire Suite on Walk Out Terrace Level, with second full kitchen. Over 7000 sft. Designer lighting, every ceramic tile bathroom is unique. AMPLE LEVEL BACK YARD TO ADD POOL. Better than "custom, " all you have to do is MOVE IN AND ENJOY this QUIET street in old GVL's very best family neighborhood!

Welcome to an extraordinary custom home in the Alta Vista neighborhood, one of Greenville's most sought-after neighborhoods — walking distance to downtown Greenville, Cleveland Park, and the Swamp Rabbit Trail, and just minutes from the Caine Halter Family YMCA. Completed in 2025 by J. Francis Builders with interior design by Fowler Interiors, this home is a masterclass in craftsmanship, thoughtful design, and everyday livability. Every one of the five bedrooms enjoys its own private en-suite bath, complemented by a convenient powder room. Throughout the home, exquisite trim and millwork, custom inset cabinetry, and designer lighting from Visual Comfort and Curry & Company set an elevated tone, while Emtek hardware and Palmer Industries custom-built brass shelving in the wet and dry bars add refined, artisan-level detail. The heart of the home is a chef's kitchen outfitted with Thermador appliances, including an induction range, a steam/convection oven, and a 48-inch French door panel refrigerator with dual ice-making capability. Soapstone and Caesarstone countertops and custom walnut cabinetry complete the space, while an adjoining scullery — with its own dishwasher and a striking steel window — keeps everyday prep convenient and organized. Additionally, on the main level, enjoy having a two-car attached garage with Epoxy flooring. The living room features a dry bar with beverage drawers, perfect for entertaining, while the primary suite and walk-in main-level laundry room with sink adds everyday convenience (a second washer/dryer connection is also available upstairs). Two outdoor living porches with fireplaces extend the living space outward, including a three-season porch with Sunpacer enclosures and its own fireplace on the main level. A gas copper lantern welcomes guests at the front entry. Designed for entertaining, the lower level features a golf simulator with a Full Swing system offering not only golf but football, dodgeball, skee-ball, and other games for kids and adults alike, all enhanced by surround sound and an 85-inch TV. A pool table, a built-in bar with Palmer Industries custom brass and glass shelving and an antique mirror backdrop, and beverage refrigerator drawers with an ice maker and dishwasher make this level an entertainer's dream. Additionally, enjoy the covered patio with another wonderful outdoor fireplace. This level also provides large, conditioned storage space. Additional features include a whole-home generator, walkout attic storage with spray foam insulation, heated floors in the primary bathroom, an epoxy-coated garage floor, professional hardscape and landscaping with front and backyard landscape lighting, a large fenced backyard with room for a pool, stone raised garden beds and a garden storage area with sink. Set in Alta Vista, this home offers rare proximity to everything that makes Greenville special — an easy walk to downtown restaurants and shops, Cleveland Park, and the Swamp Rabbit Trail, with quick access to the Caine Halter Family YMCA. A one-of-a-kind custom build blending quality construction, designer finishes, and an unbeatable location set on just under half an acre— this is Greenville living at its finest.