Charming two cottage Chilmark retreat tucked away on Middle Road. Nestled into a rolling hill, the main structure overlooks the quintessential up-island setting: a lower pasture lined with ancient stone walls and mature trees. Completing the main house is a first-floor ensuite master, two additional bedrooms, a dramatic wall of windows, and a sizable deck perfect for summer evenings. The separate one-bedroom guest house offers an idyllic, private refuge with a wood-burning fireplace, ample natural light, and a bonus sleeping loft. Situated on 1.3 acres, this property is in close proximity to all that Chilmark offers- Lucy Vincent Beach, Squibnocket, Chilmark General Store, and an abundance of scenic hiking trails. Renovations have just begun to refurbish this 1973 cottage, making it an excellent opportunity for a buyer to perfect their up-island sanctuary.