The Maplewood Cottage (2,932 sq ft) is complemented by a fully furnished detached guest house (479 sq ft), creating a property that combines flexible living space, privacy, and the character of Weymouth Heights Historic District within one of Southern Pines' most established residential settings. Thoughtfully updated while preserving the scale and feel of the surrounding neighborhood, the property offers five bedrooms, multiple gathering spaces, and strong connections between indoor and outdoor living. Just off the front entry, a more intimate sitting room creates a welcoming introduction to the home. Beyond the double doors, the main living spaces open into the great room and adjoining Carolina room, where vaulted ceilings, expansive windows, and views of the surrounding landscape create a natural focal point. French doors, exposed brick accents, and strong sight lines throughout the rear living areas reinforce the connection between the interior spaces and the mature pines beyond. The kitchen, dining, and living areas are comfortably integrated to create a functional and inviting central living space. The renovated kitchen balances function and design with stone countertops, ceramic tile backsplash, Bertazzoni gas range, and a large central island that anchors the space naturally. Adjacent to the kitchen, the butler's pantry includes a wet bar along with additional storage and serving space. The primary suite features custom armoire-style storage, fireplace feature wall, and a spacious bath with dual vanity and large walk-in shower. Expansive windows throughout the home bring in soft natural light and reinforce the connection to the surrounding property. Outdoor spaces feel private and well established, with brick patios, garden paths, mature landscaping, and a large fenced backyard that includes a separate white picket enclosed area accented with copper-capped detailing. One patio connects directly to the primary suite and hot tub area, while another extends from the rear living spaces beneath the canopy of mature trees. Above the detached two-car garage, the fully furnished, turn-key guest house extends the functionality of the property, offering a comfortable and well-designed space for visitors or longer-term stays. Complete with a full bath, kitchenette, and open living area, it provides flexibility while maintaining privacy from the main residence. A short distance from downtown Southern Pines and the trails of Weymouth Woods, the property is well positioned for both daily convenience and outdoor recreation. Residents enjoy easy access to Broad Street's locally owned restaurants, shops, and historic downtown character, along with miles of nearby walking trails through protected longleaf pine forest characteristic of the Sandhills region. This 1.68 acre property offers a distinctive combination of privacy, updated living space, guest accommodations, and proximity to both downtown Southern Pines and Weymouth Woods within one of the area's most established neighborhoods.