This compound built a second house just to watch its own pond.

Twenty-two acres on Martha’s Vineyard, planned for privacy and flexibility. At the center: a Robert A.M. Stern–designed main residence and, beside its own pond, the architecturally striking 2021 Pond House with cathedral ceilings, exposed beams, shiplap, and a dramatic stone fireplace. A 1,700-square-foot Amish barn adds additional living quarters, while separate driveways serve both parcels. Outdoor living is dialed: a heated 20' x 60' pool on a broad bluestone terrace, an exceptional pool house with a full gym, sauna, massage room, and a screened porch with fireplace, plus boardwalk-style links between cottage spaces. Membership in the private Boldwater Association conveys, granting access to an Atlantic Ocean beach, boat landing, tennis courts, and pickleball, coastal perks without sacrificing the sanctuary feel of this inland compound. For multigenerational living, private retreats, or legacy ownership, it’s a rare Vineyard estate where architecture, landscape, and craftsmanship do the talking.