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12 Boldwater Road Edgartown — Photo 1 of 40

12 Boldwater Road Edgartown — Photo 1 of 40

$9,950,000

Investment Analysis — 12 Boldwater Road

Edgartown, MA 02539 — Boldwater

Based on HUD Small Area Fair Market Rent for Dukes County, MA, a 8-bedroom in 02539 carries an estimated $3,430/mo in gross rent — about a -0.26% cap rate and $-26,225/yr in estimated NOI at the $9,950,000 list price. Adjust every assumption in the calculator below.

View Standard Listing

Beds

8

Baths

10

SqFt

7,585

Style

Single Family

Built

1994

A winding approach through 9.8 acres sets the tone for 12 Boldwater Road: a private Edgartown estate of uncommon scale and distinction. At its heart stands a seven-bedroom, ten-bath residence designed by Robert A.M. Stern. A gracious foyer introduces light-filled interiors, a dramatic post-and-beam living room, multiple fireplaces, and a gourmet kitchen equally suited to intimate dinners and large gatherings. The grounds offer the ease of a private resort. Spend the day beside the heated 20' x 60' pool, or retreat to the pool house with an exterior hot tub, complete with a fully equipped gym, sauna, massage room, and screened porch with fireplace. Every element of the property invites a slower, more considered way of living on the Vineyard. The Boldwater Association membership adds access to a private ocean beach, boat landing, tennis, and pickleball courts. Together with the estate’s remarkable privacy, these amenities offer a compelling balance of seclusion and coastal recreation. Architectural heritage, expansive land, and a setting designed to be enjoyed across generations make 12 Boldwater Road an extraordinary Vineyard offering.

Estimates — not financial advice

These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.

Property Details

Financials

Original Price$9,950,000
Annual Taxes$27,507
HOA Fee$2500

Parking

Garage2
Off-Street12

Interior Specifications

Total Rooms20
Fireplaces6
FlooringWood, Tile
BasementFull, Finished, Interior Entry

Climate & Utilities

HeatingForced Air, Natural Gas, Propane
CoolingCentral Air
WaterPrivate
SewerPrivate Sewer

Building & Exterior

ConstructionFrame
RoofWood, Shake
FoundationConcrete Perimeter
ZoningA12

Property & Lot

Acres9.78
SqFt Lot426,016
Lot FeaturesWooded, Other

Amenities & Appliances

Range • Oven • Dishwasher • Microwave • Refrigerator • Washer • Dryer

Neighborhood

Shopping • Pool • Tennis Court(s) • Park • Walk/Jog Trails • Stable(s)

Geography

Floorplan Breakdown

Structural Layout

Second
Primary BedroomBedroom 2Bedroom 3Bedroom 4Bedroom 5Bathroom 2Bathroom 3
First
Dining RoomFamily RoomBathroom 1
Main,First
Living RoomKitchen
Living Room
Lvl Main,First

Cathedral Ceiling(s), Beamed Ceilings, French Doors

Dining Room
Lvl First
Kitchen
Lvl Main,First

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

Family Room
Lvl First
Primary Bedroom
Lvl Second

Walk-In Closet(s), Balcony / Deck, French Doors

Bedroom 2
Lvl Second
Bedroom 3
Lvl Second
Bedroom 4
Lvl Second
Bedroom 5
Lvl Second
Bathroom 1
Lvl First
Bathroom 2
Lvl Second
Bathroom 3
Lvl Second

Property History

Listed
$9,950,000

Sep 30, 2026

MLS® 73584420

Expired
$9,995,000

Sep 18, 2025

MLS® 73346189

Listed
$9,995,000

Mar 17, 2025

MLS® 73346189

Listing Provided By

Listing Agent: Michael Carucci

Listing Office: Serhant

MLS® Number: 73584420