Nestled in the Upper Grassy Hill community of Woodbury, CT, 557 Upper Grassy Hill Road offers a lifestyle of luxury and comfort. This stunning Colonial residence spans 3784 square feet across three meticulously designed levels. As you step into the grand two-story foyer with gleaming marble floors, you are immediately enveloped in a sense of timeless elegance. The main level features a gracious living and dining room, ideal for entertaining, a private home office, and a sun-drenched kitchen equipped with granite countertops, stainless steel appliances, and a skylight. The kitchen seamlessly flows into the spacious family room, complete with a cozy pellet stove. Step outside to the expansive deck for a serene outdoor escape with distant views, perfect for relaxation and entertainment. Moving upstairs, you'll discover three generous bedrooms, including a luxurious primary suite with hickory hardwood floors, trey ceiling, dual walk-in closets, and a beautifully remodeled spa bath. A dressing room/sitting room adds a touch of luxury to this peaceful retreat. The fully finished walk-out lower level is a standout feature of the home, offering an exceptional in-law or au pair setup. With hickory floors throughout, a kitchen area with granite counters, a bedroom with built-ins and a Murphy bed, a marble full bath with a steam shower, and a spacious great room with built-in seating, this space is perfect for extended family or guests. French doors lead to a stunning bluestone patio with a plunge pool/spa, creating a space for both relaxation and entertainment. Additional highlights of this property include surround sound, a Belgium block-lined driveway, stone walls, an irrigation system, and a generator for added convenience and peace of mind. Situated just 90 minutes from NYC, this home is part of the self-managed Cardinal Hill HOA and backs up to designated open space, offering privacy and tranquility. The Cardinal Hill HOA provides access to a range of amenities for residents to enjoy. This property is not just a home; it's a lifestyle. Impeccably maintained and thoughtfully designed, 557 Upper Grassy Hill Road presents a rare opportunity to own a piece of Woodbury's premier real estate. Experience the perfect blend of sophistication, comfort, and tranquility in this exquisite residence.