72 Chappaquiddick Ave

$2,999,000
Price
8
Beds
3,770 Sq. Ft.
$795 / Sq. Ft.
3,770
Sq. Ft.
$795
per Sq. Ft.

Description

WELCOME to this turn-key CHAPPY COMPOUND! This property offers it ALL, with its Six (6) Bedroom, Five (5) bath Primary Home, Two (2) bedroom, Two (2) bath GUEST HOUSE, expansive POOL HOUSE with a bath, kitchenette, large lounge area topped with a cathedral ceiling, a WORKOUT & GAME BARN, a POOL, a VOLLEY BALL COURT and a TENNIS and PICKLEBALL COURT that has recently been resurfaced with the traditional US Open colors. The court is lined for tennis as well as two full pickleball courts with portable...WELCOME to this turn-key CHAPPY COMPOUND! This property offers it ALL, with its Six (6) Bedroom, Five (5) bath Primary Home, Two (2) bedroom, Two (2) bath GUEST HOUSE, expansive POOL HOUSE with a bath, kitchenette, large lounge area topped with a cathedral ceiling, a WORKOUT & GAME BARN, a POOL, a VOLLEY BALL COURT and a TENNIS and PICKLEBALL COURT that has recently been resurfaced with the traditional US Open colors. The court is lined for tennis as well as two full pickleball courts with portable nets. Game on! All of this is set upon three acres of private, expansive land with distant WATER VIEWS! The estate is spectacularly located on Sampson Hill, being the highest elevation on Chappaquiddick. The location is convenient to the Chappy ferry, the Chappy Community Center, Slip Away Farm, the hiking trails on Land Bank properties and the beaches. A true gem of a location! This Chappy Compound has been meticulously grown and maintained over the years through architectural design, professional decorating and professional landscaping. The Workout & Game Barn was recently constructed in 2022. It has a light airy feeling with its cathedral ceiling, light colored wood and abundance of natural light streaming into its interior space. An interior barn door separates the space into two work out areas. The architecturally designed Guest House was constructed in 2018 with year round living as an option. It was designed with an open floor plan and an abundance of outdoor living spaces to make this Guest House live large. The fun Pool House sports a wooden beamed cathedral ceiling with a large open lounge area, kitchenette and bath, overlooking the Pool and Workout & Game Barn. The interplay between the Workout & Game Barn, Pool House, Pool and abutting Tennis and Pickleball Courts makes this Chappy Compound fun and playful! Strong Rental History.
  1. Listed by Michele Casavant • Vineyard Village Realty

Property Details for 72 Chappaquiddick Avenue

Zoning
R120
View
D/Oc, Trees/Woods
LISTING UPDATED: 12/24/2025 06:46 AM

Property Details for 72 Chappaquiddick Avenue

StatusActive
MLS #42786
Days on Market363
Taxes$6,517 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS Type1 Family / Single Family Residence
Year Built1998
Lot Size3.00 AC / 130,680 SF
CountyDukes County

Location

Listing Courtesy of Vineyard Village Realty, Michele Casavant
Add your commute

Building Information for 72 Chappaquiddick Avenue

Stories-Year Built1998Building Size-Lot Size3.00 AC / 130,680 SF

Payment Calculator

$15,362 per month

30 year fixed, 6.28% Interest

Principal and Interest

$14,819

Property Taxes

$543

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 72 Chappaquiddick Avenue

Summary
Location and General Information
  • Latitude: 41.3769284
  • Longitude: -70.4834958
  • Listing ods: WViews, Deck, Garden, Patio, Porch, ScrPorch, P/Pool, Tennis, PubBch
  • MLS Area Major: 2
Taxes and HOA Information
  • Tax Assessed Value: $2,459,500.00
  • Tax Lot: 166
  • Tax Map Number: 31
  • Tax Other Annual Assessment Amount: $420,400.00
  • Tax Year: 2023
Parking
  • Parking Features: plenty of off street parking
Property
Lot Information
  • Lot Features: Deed Restriction: Dukes County Registry of Deeds, Book 71, page 227, doc. 13180. Dirt Road easement., Spacious landscaped yard
  • Property Type: 1 Family
Property and Assessments
  • Photos Count: 63
  • Deed No: 77
  • Approval Status: -1
  • Reviewed: Yes
  • Year Built Effective: 2011
Utilities
  • Sewer: Septic Tank
  • Utilities: Cbl
  • Water Source: Well
Interior and Exterior Features
Exterior Features
  • Exterior Features: WViews, Deck, Garden, Patio, Porch, ScrPorch, P/Pool, Tennis, PubBch
Interior Features
  • Main Level Bedrooms: 4
  • Other Structures: Guest House, Workout & Game Barn, Pool House, Pool, Tennis court which has been lined with two full pickleball courts with portable nets, Gazebo, Shed, Enclosed raised garden area.
  • Rooms Total: 13
  • Appliances: Stove: yes, Washer: yes
  • Fireplace Features: One gas fireplace in Guest House
  • Fireplace: No
  • Flooring: hardwood and tile
  • Foundation Details: full/poured
  • Furnished: Partially
  • Heating: Electric
  • Interior Features: Ins,MiniSplit,OSh, Floor 1: The spacious entry foyer soars to the second floor. This floor has four (4) bedrooms and three (3) baths. Two (2) of the four (4) bedrooms on this floor have private access to the large outdoor screened in room that houses a wet bar, large lounge area, wicker swing and foosball table., Floor 2: The top floor sports a soaring ceiling with large windows and an open floor plan that has the kitchen flowing into the dining and lounge area. This entire floor has access to the oversized outdoor upper deck with water views! It is a great place to gather.

Property History for 72 Chappaquiddick Avenue

DateEvent & SourcePriceAppreciation
Dec 31, 2025

Expired

MLS PIN #73329783

$2,999,000—
Jan 28, 2025

Listed (Active)

MLS PIN #73329783

$2,999,000—
Jan 5, 2025

Listed (Active)

LINK #42786

$2,999,000—
Apr 29, 2024

Canceled

LINK #40745

$3,800,000—
May 31, 2023

Canceled

LINK #29408

$3,500,000—
May 31, 2023

Canceled

LINK #27630

$6,500,000—
May 3, 2023

Listed (Active)

LINK #40745

$3,800,000—
Jan 6, 2023

Canceled

LINK #39511

$4,200,000—
May 12, 2022

Listed (Active)

LINK #39511

$4,200,000—
Feb 28, 2017

Sold (Public Record)

Public Record #590136589

$1,200,000

+8.3% / yr

Oct 22, 2016

Expired

Martha's Vineyard MLS #21602114

—
Oct 22, 2016

Expired

Cape Cod & Islands Multiple Listing Service #21602114

$1,695,000—
Oct 20, 2016

Canceled

LINK #29930

$1,695,000—
Sep 15, 2016

Expired

MLS PIN #71977975

$1,695,000—
Mar 28, 2016

Listed (Active)

MLS PIN #71977975

$2,750,000—
Mar 16, 2016

Listed (Active)

Cape Cod & Islands Multiple Listing Service #21602114

$2,750,000—
Mar 16, 2016

Listed (Active)

Martha's Vineyard MLS #21602114

$2,750,000—
Mar 11, 2016

Listed (Active)

LINK #29930

$2,750,000—
Oct 1, 2015

Canceled

LINK #29322

$3,500,000—
Sep 8, 2015

Listed (Active)

LINK #29322

$4,900,000—
Apr 16, 2015

Canceled

LINK #28267

$4,900,000—
Apr 6, 2015

Listed (Active)

LINK #28267

$4,900,000—
Feb 26, 2015

Canceled

LINK #27614

$6,500,000—
Feb 26, 2015

Canceled

LINK #27591

$6,500,000—
Nov 3, 2014

Listed (Active)

LINK #27614

$6,500,000—
Oct 22, 2014

Canceled

LINK #27558

$2,500,000—
Oct 22, 2014

Listed (Active)

LINK #27591

$6,500,000—
Oct 12, 2014

Listed (Active)

LINK #27558

$2,500,000—
Dec 9, 2011

Sold (Public Record)

Public Record #320796587

$790,625—
Dec 9, 2011

Sold

LINK #21320

$790,625—
Nov 22, 2011

Contingent

LINK #21320

—
May 11, 2011

Listed (Active)

LINK #21320

$995,000—
DateEvent & SourcePrice
12/31/2025

Expired

MLS PIN #73329783

$2,999,000
01/28/2025

Listed (Active)

MLS PIN #73329783

$2,999,000
01/05/2025

Listed (Active)

LINK #42786

$2,999,000
04/29/2024

Canceled

LINK #40745

$3,800,000
05/31/2023

Canceled

LINK #29408

$3,500,000
05/31/2023

Canceled

LINK #27630

$6,500,000
05/03/2023

Listed (Active)

LINK #40745

$3,800,000
01/06/2023

Canceled

LINK #39511

$4,200,000
05/12/2022

Listed (Active)

LINK #39511

$4,200,000
02/28/2017

Sold (Public Record)

Public Record #590136589

$1,200,000

+8.3% / yr

10/22/2016

Expired

Martha's Vineyard MLS #21602114

—
10/22/2016

Expired

Cape Cod & Islands Multiple Listing Service #21602114

$1,695,000
10/20/2016

Canceled

LINK #29930

$1,695,000
09/15/2016

Expired

MLS PIN #71977975

$1,695,000
03/28/2016

Listed (Active)

MLS PIN #71977975

$2,750,000
03/16/2016

Listed (Active)

Cape Cod & Islands Multiple Listing Service #21602114

$2,750,000
03/16/2016

Listed (Active)

Martha's Vineyard MLS #21602114

$2,750,000
03/11/2016

Listed (Active)

LINK #29930

$2,750,000
10/01/2015

Canceled

LINK #29322

$3,500,000
09/08/2015

Listed (Active)

LINK #29322

$4,900,000
04/16/2015

Canceled

LINK #28267

$4,900,000
04/06/2015

Listed (Active)

LINK #28267

$4,900,000
02/26/2015

Canceled

LINK #27614

$6,500,000
02/26/2015

Canceled

LINK #27591

$6,500,000
11/03/2014

Listed (Active)

LINK #27614

$6,500,000
10/22/2014

Canceled

LINK #27558

$2,500,000
10/22/2014

Listed (Active)

LINK #27591

$6,500,000
10/12/2014

Listed (Active)

LINK #27558

$2,500,000
12/09/2011

Sold (Public Record)

Public Record #320796587

$790,625
12/09/2011

Sold

LINK #21320

$790,625
11/22/2011

Contingent

LINK #21320

—
05/11/2011

Listed (Active)

LINK #21320

$995,000

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

Public Records for 72 Chappaquiddick Avenue

Taxable ValueLand$420,400Additions$2,722,600Total$3,143,000
Tax Record2025$8,329 ($694 / month)
Home Facts
Total Finished SqFt2,162 SqFtAbove Grade Finished SqFt2,162 SqFtStories2Lot Size131,116 SqFtStyleMulti-Family Dwelling (2-4)Year Built1995CountyDUKESAPNEDGA M:0031 B:0166 L:

Schools near 72 Chappaquiddick Avenue

This home is within Edgartown School District.
Rating
School
Type
Grades
Distance
Public - PK to 8
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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72 Chappaquiddick Avenue is a single family home for sale in Edgartown, MA 02539. This property was listed for sale on January 5, 2025 by Vineyard Village Realty, it's currently listed at $2,999,000. It has been on the market for a total of 363 days and was last sold on February 28, 2017. 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. 72 Chappaquiddick Avenue is a 8-bed, 8-bath, 3,770 sqft single family home built in 1998.

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 Vineyard Village Realty, Michele Casavant

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.