Circa 1739, this 4BR/2BA Greek Revival blends historic character with thoughtful modern updates on 2.49 private acres. Original details include wide plank floors, handcrafted woodwork, four fireplaces(two functioning)-ideal for those who appreciate timeless architecture. The spacious eat-in kitchen offers charm with everyday functionality. A first-floor bedroom and full bath provide flexible living options. Upstairs features a large primary bedroom with a fireplace, two additional bedrooms (one currently used as a dressing room), a full bath, and a bonus room ready for your vision. Outdoor highlights include gardens, multiple decks and porches, a pool, and an open barn used as a carport. A former garage offers studio or workshop potential. Recent updates include kitchen tiles, a new roof, a septic system, a boiler, an oil tank, and a new pool liner. Home to generations of Dutchess County's most notable residents, it's ready for its next chapter. Whether you're seeking a statement residence, a weekend retreat, or a truly distinguished legacy property, this timeless home invites you to become part of its storied history.