2585 River Road, Windsor (Damascus), MA, 18415 | $699,000

Step into an extraordinary 1895 Delaware Riverfront estate where historic character meets modern luxury—all just an easy stroll across the bridge to the vibrant hamlet of Callicoon. Set on 1. 25 lush acres with a stream at the rear, this thoughtfully restored property includes a beautifully renovated 4-bedroom main residence, a stylish 1-bedroom guest house/investment rental, and a refurbished barn ready for creative use or practical storage. The main home welcomes you with a tiled mudroom that opens to a light-filled living room and a sleek dine-in kitchen equipped with quality stainless appliances and contemporary finishes. A convenient laundry room with half bath sits just off the kitchen. The expansive screened porch offers additional living flexibility, complete with a bonus room featuring its own split unit—ideal for a home office or guest overflow. Upstairs, the second-floor landing introduces a cozy sitting nook, two lovely bedrooms, and a large bath showcasing a soaking tub perfectly positioned for river and landscape views, a walk-in shower, and a custom vanity. The original Palladian windows flood this level with natural light. The top floor adds two more bedrooms and a full bath, creating a quiet private escape. The guest house/rental investment impresses with wide plank floors, a generous living room, a full bath with laundry, and a striking kitchen appointed with Bosch and Haier appliances and dramatic stone counters. Upstairs, a versatile sitting area leads to a serene, carpeted bedroom. The barn features a new metal roof, vapor barrier, and electricity—ideal for a workshop, studio, or seasonal storage. A brand-new river deck and staircase now provide easy, private access to the Delaware River, making this already exceptional property even more enticing. With Spectrum internet and unbeatable walkability to Callicoon’s dining, shopping, and entertainment, this rare riverfront offering blends historic craftsmanship, modern comfort, and Catskills lifestyle in one unforgettable package.

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