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Sheena Ruggirello

sheena.ruggirellos@gmail.com +1(860) 222-4734

$14,500,000

Est. payment - /mo

11 Beds

12 Baths

9,500 SqFt

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Key Details

Property Type Single Family Home

Sub Type Single Family Residence

Listing Status Active

Purchase Type For Sale

Square Footage 9,500 sqft

Price per Sqft $1,526

Subdivision Boldwater

MLS Listing ID 73552898

Style Cape

Bedrooms 11

Full Baths 11

Half Baths 2

HOA Fees $2,500/ann

HOA Y/N true

Year Built 1994

Annual Tax Amount $35,039

Tax Year 2026

Lot Size 21.850 Acres

Acres 21.85

Property Sub-Type Single Family Residence

Property Description

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.

Location

State MA

County Dukes

Zoning A12

Direction Off Edgartown West Tisbury Road via Pohoganot Road.

Rooms

Basement Full, Finished, Interior Entry

Primary Bedroom Level Second

Kitchen Countertops - Stone/Granite/Solid, Kitchen Island, Wet Bar, Breakfast Bar / Nook

Interior

Interior Features Bedroom, Sauna/Steam/Hot Tub

Heating Forced Air, Natural Gas, Propane

Cooling Central Air

Flooring Wood, Tile

Fireplaces Number 6

Fireplaces Type Dining Room, Family Room, Living Room, Master Bedroom

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

Laundry In Basement

Exterior

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

Garage Spaces 2.0

Pool Pool - Inground Heated

Community Features Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Stable(s), Golf, Medical Facility, Laundromat, Bike Path, Public School, Other

Waterfront Description Waterfront,Ocean,Pond,Lake/Pond,Ocean,Beach Ownership(Private)

Roof Type Wood,Shake

Total Parking Spaces 14

Garage Yes

Private Pool true

Building

Lot Description Wooded, Other

Foundation Concrete Perimeter

Sewer Private Sewer

Water Private

Architectural Style Cape

Schools

Elementary Schools Edgartown

Middle Schools Edgartown

High Schools Mv Regional Hs

Others

Senior Community false

Virtual Tour https://www.youtube.com/watch?v=YB9sIfsX1fQ

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Listed by Serhant

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Sheena Ruggirello

+1(860) 222-4734

Agent | License ID: CN234452

Agent License ID: CN234452

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10 & 12 Boldwater Road Edgartown, MA 02539

Sheena Ruggirello

Key Details

Location

Rooms

Interior

Exterior

Building

Schools

Others

Nearby School & Business

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