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Bobbi Roberts
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10 & 12 Boldwater Road, Edgartown, MA 02539

$14,500,000
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New to the Market Active
BEDS11 BATHS11 full 2 partial SQUARE FEET9,500 MLS#73552898
STATUSActive PROPERTY TYPEResidential - Single Family SUBDIVISIONBoldwater

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.

10 & 12 Boldwater Road | MLS# 73552898

This single family home located at 10 & 12 Boldwater Road, Edgartown, MA 02539 is currently listed for sale with an asking price of $14,500,000. This property was built in 1994 and has 11 bedrooms and 11 full and 2 partial baths with 9500 sq. ft. & 12 Boldwater Road is located in the Boldwater subdivision. Search Boldwater real estate on bobbiroberts.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Full, Finished, Interior Entry
Cooling: Central Air
Fireplaces: 6
Garage: 2 car attached
Heating: Forced Air, Natural Gas, Propane
Home Style: Cape
Lot Size: 21.85 Acres
Roof Type: Wood, Shake
Taxes: $35,039
Year Built: 1994

Amenities

Bedroom
Sauna/Steam/Hot Tub
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

Feature Descriptions

Appliances: Range, Oven, Dishwasher, Microwave, Refrigerator, Washer, Dryer
Association Fee: $2500/Annually
Building Area Total: 9500
Community Features: Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Stable(s), Golf, Medical Facility, Laundromat, Bike Path, Public School, Other
Compensation Based On: N/A
Compensation Broker Transaction: N/A
Compensation Buyer Agency: N/A
Compensation Sub Agency: N/A
Compensation Sub Agency Offered: N/A
Days on Site: 4
Door Features: French Doors
Exterior: Frame
Fireplace Features: Dining Room, Family Room, Living Room, Master Bedroom
Fireplace Y/N: Yes
Flooring: Wood, Tile
GarageY/N: Yes
HeatingY/N: 1
HOA Y/N: Yes
Hot Tub: Yes
Kitchen: Countertops - Stone/Granite/Solid, Kitchen Island, Wet Bar, Breakfast Bar / Nook
Laundry: In Basement
Living Room: Cathedral Ceiling(s), Beamed Ceilings, French Doors
Lot Features: Wooded, Other
Master Bathroom: Yes
Master Bedroom: Walk-In Closet(s), Balcony / Deck, French Doors
Other Structures: Barn/Stable, Guest House
Parking Features: Attached
Parking Total: 12
Patio And Porch: Porch, Porch - Enclosed, Deck, Patio
Pool Features: Pool - Inground Heated
Rooms Total: 25
Sauna: Yes
Security: yes
Security Features: Security System
Sewer: Private Sewer
Spa: Yes
Spa Features: Private
Spa Y/N: Yes
Swimming Pool: Yes
Water: Private
Waterfront Features: Waterfront, Ocean, Pond, Lake/Pond, Ocean, Beach Ownership(Private)
Wooded: Yes

Local Schools

High School: Mv Regional Hs
Middle School: Edgartown
Elementary School: Edgartown

Listed By / Shown By

Listed By

Agency Name: Serhant
Agent Name: Michael Carucci
Agency Phone: 617-250-0559

agent picture

Shown By

Agent Name: Bobbi Roberts
Agent Phone:
Agency Title: Better Homes and Gardens Real Estate The Masiello Group

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Estimated Payment

$ 39,419.80 per month $32,270.71 Principal & Interest $2,919.92 Property Tax $4,229.17 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 07/25/2026. The listing information on this page last changed on 07/25/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Sat 07/25/2026 12:00:56 AM EST) or MLSPIN MLS (last updated Fri 07/24/2026 11:38:34 PM EST) or Prime MLS (last updated Fri 07/24/2026 11:33:41 PM EST) or MREIS (last updated Fri 07/24/2026 11:55:15 PM EST). Real estate listings held by brokerage firms other than Better Homes and Gardens Real Estate The Masiello Group may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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