10 & 12 Boldwater Road, Edgartown MA 02539

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.

Listing Courtesy of Grace Hagerty Real Estate Inc

DETAILS

Mls Id
44738
Status
Active
Bedrooms
11
Full Baths
11
Half Baths
2
Appliances
Stove: Wolf 6-Burner Gas Range, Washer: Yes
Water Source
Well
Flooring
2
Foundation
Full foundation
Year Built
1994
Exterior Features
Beach Access - Association, Community Tennis Court, Deck, Garden, Patio, Gym, Hot Tub, Porch - Screened, Private Pool, Covenants
Other Structures
Beyond the 6, 685 sq. ft. main house, the property carries a full complement of outbuildings: a 900 sq. ft. pool house and spa, a 20x60 pool, a 1, 442 sq. ft. second residence, an Amish barn, a detached bedroom, and a two-car garage. The pool house is the standout, set back among the gardens, it holds a home fitness center, massage room, sauna, hot tub, and full bath, with a screened porch and stone fireplace attached for post-workout hours.
Parking Features
Large private drives on both lots with ample parking
Sewer
Septic Tank
Heating
Gas/FHA
Basement
Full basement consisting of additional living space, full bathroom, wine cellar, storage, laundry room
Utilities
Cable
Lot Features
Professionally landscaped grounds set against open fields, pond, pool & spa
View
Pond, Pasture
Interior Features
A,AC,Ins,Irr,OSh, Floor 1: Vaulted ceilings, a fireplace, and a wall of French doors opening to the deck and landscaped grounds make the great room the heart of the first floor. Beyond it sits the gourmet kitchen with top-of-the-line appliances, a butler's pantry, and a sun-filled dining area built for entertaining. The main foyer opens to a dramatic staircase climbing to the master suite, alongside a cozy study, a powder room, and a large private office wrapped in floor-to-ceiling windows and warmed by a stone fireplace. The left wing holds two guest suites and a nursery or children's room, each with an en suite bath and its own access to the deck. The right wing stands apart for privacy, with two additional guest bedrooms, one and a half baths, and a second office., Floor 2: Upstairs, this wing is the master suite alone: fireplace-warmed sitting area, private deck, and his and her baths and dressing rooms.
Furnished
Unfurnished
Zoning
RA120
Listing Updated
Friday, July 31, 2026 at 1:09 PM