Originally built in 1952 and thoughtfully expanded and renovated in 2001, Maplewood Cottage seamlessly blends historic character with the comfort, functionality, and spaciousness of modern living. Complemented by a fully furnished detached guest house, the property offers a rare combination of flexible living space, privacy, and timeless appeal within Southern Pines' coveted Weymouth Heights Historic District. The 2001 expansion added 1,562 square feet while extensively re-imagining the original residence, preserving the neighborhood's architectural character while creating a home designed for the way people live today. Set on 1.68 beautifully landscaped acres, the single level residence offers 2,932 square feet with five bedrooms, multiple gathering spaces, and a seamless connection between indoor and outdoor living. Just beyond the front entry, an inviting sitting room gives way to the expansive great room and adjoining Carolina room, where vaulted ceilings, walls of windows, exposed brick accents, and French doors frame views of the surrounding pines and create an effortless connection between the home's principal living spaces. At the heart of the home, the kitchen balances timeless design with everyday functionality, featuring stone countertops, a ceramic tile backsplash, a Bertazzoni gas range, a generous center island, and an adjoining butler's pantry complete with a wet bar, additional storage, and serving space. The primary suite serves as a private retreat with custom armoire style storage, a striking fireplace feature wall, dual vanities, and a spacious walk in shower. Natural light fills the home through expansive windows that continually draw the outdoors inside. Brick patios, winding garden paths, mature landscaping, and a large fenced backyard create multiple destinations for relaxing or entertaining. A separate white picket enclosed garden accented with copper capped fencing adds another layer of charm, while the private hot tub patio extends directly from the primary suite beneath the canopy of mature trees. Above the detached two car garage, the fully furnished 479 square foot guest house offers exceptional flexibility with a kitchenette, full bath, and open living area ideal for guests, multi-generational living, a private office, or income producing opportunities. Located moments from the shops and restaurants of historic downtown Southern Pines and the scenic trails of Weymouth Woods, this exceptional property combines the charm of a historic neighborhood with the comfort and flexibility of a thoughtfully expanded home. Opportunities to own 1.68 acres with a detached guest house, generous living spaces, and this level of privacy within Weymouth Heights are exceptionally rare.