65 & 75 Deer Path Way

Discover a timeless piece of livable art. It is a masterclass in organic design by architect Robert Kennedy and builder Eric Winslow. Set on 2.48 wooded acres bordering the estuaries of Herring River (Cape Cod National Seashore), this estate offers ultimate privacy. Kennedy's signature integration of architecture and custom furnishings begins at the boardwalk entrance and continues throughout the home. The interior features connected separation, using a central chimney, open balconies, and elevation changes to define spaces while maintaining an airy flow. Multiple curving perches offer intimate views of the wild Wellfleet landscape. While social areas are open, the bedrooms are distinctly private. The property also includes a 400 sq. ft. studio loft with a kitchenette above the two-car garage, plus a separate structure housing an artist's studio (also with kitchenette) and a once-functional indoor pool. This home is the pinnacle of Outer Cape privacy and architectural intent.