Tucked away on 4.4 spectacular acres just off North Road, this one-of-a-kind Chilmark retreat blends timeless Vineyard charm with exceptional privacy. A shaded driveway leads to classic stone walls and cedar gates opening into a beautifully landscaped courtyard. The inviting porch overlooks lush gardens, creating a peaceful outdoor sanctuary. Inside, warm, light-filled living spaces and the primary suite enjoy sweeping meadow views framed by granite boulders and stately oaks. The main level offers additional sleeping accommodations, while a spacious finished lower level with a private entrance provides ideal guest quarters. Across the courtyard, an unfinished outbuilding with a screened porch offers exciting potential as a bunkhouse, studio, or office. Two garage bays accommodate cars or boats. Ideally located less than 2 miles from Menemsha Village and Beach, 1 mile from Great Rock Bight, and just 3 miles from Lucy Vincent Beach.