Located in the heart of Greenfield Hill, "Upper Meadow Farm" is a rare blend of timeless character and modern comfort. Originally dating back to 1835, this storied property at 2821 Congress Street has been thoughtfully expanded and updated over the years, most recently in 2019 by the current owners. The result is a warm, welcoming home where historic details meet a fresh, refined palette. A spacious first-floor primary suite offers privacy and stunning southern views across the property, complete with a fireplace, office, and walk-in closet. The main living areas are gracious yet inviting, ideal for everyday living or hosting guests. Upstairs are four additional bedrooms and three full baths, one currently used as a home office. Step outside and discover the true magic of the property: a beautifully reimagined former blacksmith's barn with a loft, full bath, and bar area-perfect as a guest house, studio, or entertainment space. The pool, added in 2015, is complemented by a stylish pool house featuring a kitchenette, full bath, and generous terracing for summer evenings under the stars. Set on picturesque grounds, this is an exceptional opportunity for those seeking a full-time residence or a weekend retreat in one of Fairfield's most beloved neighborhoods. A truly special home.