14 Cow Bay Rd

Edgartown, MA 02539

$15,000,000
Price
7
Beds
6,462 Sq. Ft.
$2,321 / Sq. Ft.
6,462
Sq. Ft.
$2,321
per Sq. Ft.
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Description

Set within the prestigious Cow Bay Association, one of the island’s most exclusive and sought-after enclaves, this extraordinary 1.5-acre estate embodies the pinnacle of refined coastal living. Accessed via private road through protected land, the property includes access to over 2,000 feet of private shoreline, beach cabanas, Trapps Pond and potential mooring. Despite its remarkable seclusion, the property remains just minutes from the charm and sophistication of downtown Edgartown. The six-bedroom...Set within the prestigious Cow Bay Association, one of the island’s most exclusive and sought-after enclaves, this extraordinary 1.5-acre estate embodies the pinnacle of refined coastal living. Accessed via private road through protected land, the property includes access to over 2,000 feet of private shoreline, beach cabanas, Trapps Pond and potential mooring. Despite its remarkable seclusion, the property remains just minutes from the charm and sophistication of downtown Edgartown. The six-bedroom main residence is a masterclass in timeless design and effortless elegance. Grand yet inviting, the home offers beautifully proportioned living and dining spaces, a thoughtfully designed chef’s kitchen and a sweeping screened porch, all oriented to capture wonderful views across the pool and out to Vineyard Sound. Every room is infused with natural light and a sense of understated luxury. The grounds are nothing short of spectacular, a curated landscape of mature plantings, expansive stone terraces, and romantic pergolas draped in cascading wisteria. At the heart of the property, a stunning pool and lounge area create a private resort-like setting, ideal for both intimate relaxation and sophisticated, large-scale entertaining. A separate carriage/guest house with full amenities offers flexible accommodations for guests or staff. This is more than a home; it is a rare and irreplaceable offering, a legacy property in one of the island’s most coveted coastal settings.
  1. Listed by Gerrett Conover • Landvest MV

Property Details for 14 Cow Bay Road

Zoning
R60
View
Pond, Ocean
LISTING UPDATED: 06/03/2026 03:24 PM

Property Details for 14 Cow Bay Road

StatusActive
MLS #44402
Days on Market36
Taxes$25,883 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS Type1 Family / Single Family Residence
Year Built1958
Lot Size1.50 AC / 65,340 SF
CountyDukes County
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Location

Listing Courtesy of Landvest MV, Gerrett Conover
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Building Information for 14 Cow Bay Road

Stories-Year Built1958Building Size-Lot Size1.50 AC / 65,340 SF

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$76,904 per month

30 year fixed, 6.36% Interest

Principal and Interest

$74,747

Property Taxes

$2,157

HOA Dues

$0

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Property Information for 14 Cow Bay Road

Summary
Location and General Information
  • Latitude: 41.403022
  • Longitude: -70.5333009
  • Listing ods: AscBch, Deck, Garden, H/Tub, Patio, Porch, ScrPorch, P/Pool, WViews
  • Listing other Building: Grg
  • MLS Area Major: 2
Taxes and HOA Information
  • Tax Assessed Value: $6,286,000.00
  • Tax Lot: 24
  • Tax Map Number: 12
  • Tax Other Annual Assessment Amount: $3,849,691.00
  • Tax Year: 2026
Parking
  • Parking Features: Yes
Property
Lot Information
  • Lot Features: Yes
  • Property Type: 1 Family
Property and Assessments
  • Photos Count: 37
  • Approval Status: -1
  • Reviewed: Yes
  • Year Built Effective: 2019
Utilities
  • Sewer: Septic Tank
  • Utilities: Cbl
  • Water Source: Well
Interior and Exterior Features
Exterior Features
  • Exterior Features: AscBch, Deck, Garden, H/Tub, Patio, Porch, ScrPorch, P/Pool, WViews
Interior Features
  • Rooms Total: 13
  • Appliances: Stove: Yes, Washer: Yes
  • Fireplace Features: Yes
  • Fireplace: No
  • Flooring: Hardwood
  • Furnished: Unfurnished
  • Heating: OFHA
  • Interior Features: A,AC,Irr,OSh

Property History for 14 Cow Bay Road

DateEvent & SourcePriceAppreciation
May 1, 2026

Listed (Active)

LINK #44402

$15,000,000—
Nov 9, 1995

Sold (Public Record)

Public Record #86963099

$1,250,000—
DateEvent & SourcePrice
05/01/2026

Listed (Active)

LINK #44402

$15,000,000
11/09/1995

Sold (Public Record)

Public Record #86963099

$1,250,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 14 Cow Bay Road

Taxable ValueLand$3,667,100Additions$6,157,300Total$9,824,400
Tax Record2025$26,035 ($2,170 / month)
Home Facts
Total Finished SqFt4,783 SqFtAbove Grade Finished SqFt4,783 SqFtStories2Lot Size65,362 SqFtStyleMulti-Family Dwelling (2-4)Year Built1958CountyDUKESAPNEDGA M:0012 B:0024 L:

Schools near 14 Cow Bay Road

This home is within Edgartown School District.
Rating
School
Type
Grades
Distance
Edgartown Elementary School
Public - PK to 8
Martha's Vineyard Regional High School
Public - 9 to 12
Rating
School
Distance
Edgartown Elementary School
PublicPK to 8

Martha's Vineyard Regional High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 14 Cow Bay Road, Edgartown, MA 02539

14 Cow Bay Road is a single family home for sale in Edgartown, MA 02539. This property was listed for sale on May 1, 2026 by Landvest MV, it's currently listed at $15,000,000. It has been on the market for a total of 36 days and was last sold on November 9, 1995. This listing's school districts are Edgartown School District, Marthas Vineyard School District. Nearby schools include Edgartown Elementary School and Martha's Vineyard Regional High School. 14 Cow Bay Road is a 7-bed, 9-bath, 6,462 sqft single family home built in 1958.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Landvest MV, Gerrett Conover

The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. The property listing data and information, and the images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the images, set forth herein.