Welcome to one of Greenwood‘s most distinguished private residences, where timeless Southern architecture, exceptional craftsmanship, and gracious Southern living come together on two beautifully landscaped estate-sized corner lots totaling 1.58 acres. Offering approximately 4718 ft., this remarkable executive home has been lovingly maintained and thoughtfully updated throughout the years, creating a rare opportunity to own one of Greenwood‘s true legacy properties. Surrounded by a magnificent canopy of mature trees, more than 80 flowering Dogwoods, peaceful courtyard gardens with seating areas, and professionally designed landscaping, the setting offers remarkable privacy while remaining conveniently located in the heart of Greenwood. Every season brings new beauty to the property, with multiple outdoor living spaces designed for entertaining, relaxing, birdwatching, and enjoying the natural surroundings. Inside, rich hardwood floors, custom millwork, inviting fireplaces, spacious living areas, and a massive swirling wrought-iron staircase at the entry create an atmosphere of timeless elegance. The beautifully updated kitchen features granite countertops, custom cabinetry, stainless steel appliances, custom island with seating, bay window seating, updated tile backsplash, abundant workspace, and seamless flow into the adjoining living and dining areas, making it ideal for both everyday living and entertaining. Designed with gathering in mind, the formal dining room with granite-topped cocktail/beverage bar opens through double doors onto an expansive screened-in porch complete with a wood-burning fireplace, creating an exceptional indoor-outdoor entertaining space. Just beyond, the impressive wood-beamed ceiling studio just off the screened-in porch completes the entertaining space by offering incredible flexibility as an art studio, recreation room, media room, executive office, fitness room, or private guest retreat. The partially-finished walkout lower basement level provides an additional 1,292 sq ft of living space with a half bath while also offering extensive workshop, office, and storage areas. Car enthusiasts, hobbyists, and those needing exceptional storage will appreciate the rare five garage bays and dedicated utility space for yard equipment found beneath the home. A charming detached one bedroom, one bath, one-level cottage adds even more versatility, serving perfectly as an overnight guest cottage, private office, or creative studio. The property also offers abundant storage throughout, making it as practical as it is beautiful. Extensive updates provide exceptional peace of mind, including a new architectural roof recently installed (2026), two newer HVAC systems (2023 and 2025), replacement windows and exterior doors, updated kitchen appliances (2024), kitchen backsplash (2025), sewer line replacement to the road (2023), beautifully renovated bathrooms with custom cabinetry and marble/travertine countertops, tankless hot water heater, updated electrical, Gutter-guard system added, updated locks 2026 and exterior doors, and exterior wood shingles freshly stained by professional painter along with numerous other additional improvements performed by sellers to lovingly maintain the prestige condition of this million dollar home. Pine trees (approximately 20) were professionally removed to further enhance the beauty, openness, and usability of the grounds. Adding to its rich history, the exceptional residence was proudly featured on the Greenwood Women's Club Christmas Tour of Homes, a testament to its timeless beauty and architectural significance. Combining classic Southern elegance, extensive modern updates, extraordinary entertaining spaces, mature landscaping, five garage bays, a detached guest cottage, and unparalleled flexibility, 183 Rutledge Road is far more than a home – it's a rare Greenwood legacy estate ready for you to begin its next chapter.
