22 Bennett Street

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.