Gracious classic two-story residence situated on a rare double lot along a magnificent oak-lined street in Northeast Greenwood, Mississippi. This elegant home blends timeless character with thoughtful updates, featuring beautifully refinished hardwood floors, freshly painted interiors, and tall ceilings. Spacious formal living and dining rooms provide ideal entertaining spaces, while a warm and inviting den with fireplace and brick floors opens to a generously sized kitchen complete with breakfast bar, Viking gas range, new dishwasher and refrigerator and indoor washer&dryer. The flexible floor plan includes a main-level bedroom and bathroom suitable for guests or a private office. Upstairs, the primary suite features a charming balcony overlooking the property and surrounding neighborhood. Two additional bedrooms and a full hall bath provide comfortable accommodations for family or guests. Significant recent improvements include new roofs on both the main house and guest house, along with a freshly painted exterior that enhances the home's classic Southern appeal. A separate two-story guest house offers outstanding potential for additional living space, rental income, or a studio. The structure features a new roof and exterior paint, with new windows and exterior entrance doors already installed on the lower level. Windows for the second floor are included and ready for installation. The spacious interior is ready for renovation, providing an excellent opportunity to customize the space to your needs and vision. Located within walking distance of historic downtown Greenwood, this home offers convenient access to the Yazoo River Trail and Arboretum and to one of the Mississippi Delta's most charming shopping districts. Explore distinctive boutiques, antique galleries, artisan-crafted Mississippi goods, beautiful home decor, and stylish fashions -- all part of Greenwood's vibrant and welcoming downtown experience. Classic architecture, modern updates, and exceptional potential make this a rare Northeast Greenwood opportunity.