10 & 12 Boldwater Road

Taxes: $35,039 (2026)

About this home

A rare offering of extraordinary scale and architectural significance, this 22-acre Martha's Vineyard estate represents a category of ownership seldom available on the Island. Designed around privacy, natural beauty, and enduring craftsmanship, the living spaces encompass more than 9,500 square feet across multiple thoughtfully designed structures, creating an unparalleled setting for multigenerational living, private retreats, or legacy ownership. Altogether, the compound offers 11 bedrooms and 13 bathrooms across its collection of residences and guest accommodations. At its heart is the Robert A.M. Stern-designed main residence—an architectural work by one of America's most celebrated architects, whose residential designs are prized for their timeless elegance and lasting value. Complementing the estate is the architecturally striking Pond House, completed in 2021, featuring cathedral ceilings, exposed beams, shiplap detailing, a dramatic stone fireplace, screened porch overlooking the pond, and beautifully appointed interiors that rival the finest boutique hotels. A 1,700-square-foot Amish barn includes additional living quarters, and private driveways serving both parcels provide exceptional flexibility while maintaining complete privacy throughout the property. Resort-caliber amenities elevate the experience, including a heated 20' x 60' swimming pool, an exceptional pool house with a fully equipped gym, sauna, massage room, and a screened porch with fireplace for effortless indoor-outdoor entertaining. Conveying with the property is coveted membership in the exclusive Boldwater Association, granting access to a private Atlantic Ocean beach, boat landing, tennis courts, and pickleball—offering the best of Vineyard coastal living without sacrificing the remarkable privacy of this inland sanctuary. This is far more than a luxury home. It is a private estate where architecture, landscape, and thoughtful design become the defining amenities. For the discerning buyer who values land, beauty, and architectural pedigree above a traditional waterfront address, this is an irreplaceable Vineyard legacy property unlike anything else available today.

Property details

Sewer

On-Site

Style

Cape

Water

Private Water

Cooling

Central Air

Heating

Forced Air, Hot Air Gravity, Hot Water Radiators

Type

Detached

Flooring

Wood, Tile

Road type

Private

Appliances

Range, Wall Oven, Dishwasher, Microwave, Refrigerator, Washer, Dryer

Waterfront

Ocean, Pond

Master Bath

Yes

Construction

Aluminum

Roof

Membrane, Other (See Remarks)

Garage

Attached

Lot

Wooded, Other (See Remarks)

Basement

Full, Finished, Interior Access

Exterior

Porch, Porch - Enclosed, Deck, Patio, Balcony, Pool - Inground Heated, Tennis Court, Gutters, Hot Tub/Spa, Barn/Stable, Professional Landscaping, Sprinkler System, Decorative Lighting, Garden Area, Guest House, Outdoor Shower

Interior

Security System, Cable Available, Sauna/Steam/Hot Tub, Intercom, French Doors

Waterview Features

Pond