Nestled in coveted Greenfield Hill, Applewood is a rare and charming 2-acre petite estate that seamlessly blends historic character with exceptional potential. Originally a barn, nestled within the remnants of a picturesque apple tree farm, this unique home offers an incredible opportunity to renovate, reimagine, or build anew while taking advantage of the existing 2-BEDROOM GUEST COTTAGE, INGROUND POOL and lovingly curated gardens planted over the last 2 decades. The main residence is filled with vintage appeal including wood-burning fireplace, custom built-ins and hardwood floors. Notable features include a private guest wing with full bath, the inviting screened porch, primary bedroom with bath en suite in a second wing and the finished walk-out level. This lower level presents a flexible bonus room/BR with full bath and fireplace with wood-burning stove. MAIN RESIDENCE: SF is 1815 + 209 screened porch + 480 Fin LL = 2504 SF with 4BR, 4 full baths. A versatile GUEST HOUSE offers endless possibilities, whether for guests, a home office, or rental income. The cozy living room features a wood-burning fireplace and built-ins open to kitchen, while 2 bedrooms share 1 full bath. SF = 930 SF. An IN-GROUND POOL provides a refreshing escape embraced by a perimeter of mature trees. An idyllic setting adorned with stone walls, creeping ivy and stone fireplace. Walk along the period homes, shady lanes and meandering stone walls to Greenfield Hill's center, farmer's market and parks. The location of Applewood is highly sought-after, just a short stroll from the Greenfield Hill town green with its annual Dogwood festival and surrounding homes include multi-million $$ gentleman farms and estates. Close to private and public schools, private clubs and Greenfield Hill's charming center for coffee, dinner, farmer's market or shopping. Sited in lower Greenfield Hill, the location is notable for its convenience to train, Southport, Westport + Fairfield town centers.