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.
For sale
$2,999,000
72 Chappaquiddick Ave, Edgartown, MA 02539
8beds
3,770sqft
Est.:
Single Family Residence
Built in 1998
3 Acres Lot
$-- Zestimate®
$795/sqft
$-- HOA
What's special
Cathedral ceilingWooden beamed cathedral ceilingHighest elevationOpen floor planDistant water viewsAbundance of natural lightOutdoor living spaces
- 458 days |
- 919 |
- 37 |
Zillow last checked: 7 hours ago
Listing updated: December 24, 2025 at 03:46am
Listed by:
Michele Casavant,
Vineyard Village Realty
Source: LINK,MLS#: 42786
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 8
- Bathrooms: 8
- Full bathrooms: 7
- 1/2 bathrooms: 1
- Main level bedrooms: 4
Heating
- Electric
Appliances
- Included: Stove: yes, Washer: yes
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.
- Flooring: hardwood and tile
- Basement: Two (2) bedrooms, one (1) bath, an open laundry/lounge area, a large linen storage closest and a utility closet.
- Fireplace features: One gas fireplace in Guest House
Interior area
- Total structure area: 3,770
- Total interior livable area: 3,770 sqft
Property
Parking
- Parking features: plenty of off street parking
Features
- Exterior features: WViews, Deck, Garden, Patio, Porch, ScrPorch, P/Pool, Tennis, PubBch
- Has view: Yes
- View description: D/Oc, Trees/Woods
- Has water view: Yes
- Water view: D/Oc
- Frontage type: None
Lot
- Size: 3 Acres
- Features: Deed Restriction: Dukes County Registry of Deeds, Book 71, page 227, doc. 13180. Dirt Road easement., Spacious landscaped yard
Details
- Additional 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.
- Parcel number: EDGAM0031B0166L
- Zoning: R120
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Foundation: full/poured
Condition
- Year built: 1998
- Major remodel year: 2011
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
- Utilities for property: Cbl
Community & HOA
Location
- Region: Edgartown
Financial & listing details
- Price per square foot: $795/sqft
- Tax assessed value: $2,879,900
- Annual tax amount: $6,517
- Date on market: 1/5/2025
- Listing agreement: E
Estimated market value
Not available
Estimated sales range
Not available
$6,937/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 1/5/2025 | Listed for sale | $2,999,000-21.1%$795/sqft |
Source: LINK #42786 Report a problem | ||
| 4/29/2024 | Listing removed | $3,800,000$1,008/sqft |
Source: LINK #40745 Report a problem | ||
| 5/3/2023 | Listed for sale | $3,800,000-9.5%$1,008/sqft |
Source: LINK #40745 Report a problem | ||
| 1/6/2023 | Listing removed | $4,200,000$1,114/sqft |
Source: LINK #39511 Report a problem | ||
| 5/12/2022 | Listed for sale | $4,200,000+250%$1,114/sqft |
Source: LINK #39511 Report a problem | ||
| 2/28/2017 | Sold | $1,200,000-29.2%$318/sqft |
Source: Public Record Report a problem | ||
| 9/16/2016 | Listing removed | $1,695,000$450/sqft |
Source: Point B Realty #21602114 Report a problem | ||
| 8/26/2016 | Price change | $1,695,000-15%$450/sqft |
Source: Point B Realty #21602114 Report a problem | ||
| 8/3/2016 | Price change | $1,995,000-9.1%$529/sqft |
Source: Point B Realty #21602114 Report a problem | ||
| 7/13/2016 | Price change | $2,195,000-12%$582/sqft |
Source: Point B Realty #21602114 Report a problem | ||
| 4/28/2016 | Price change | $2,495,000-9.3%$662/sqft |
Source: Point B Realty #21602114 Report a problem | ||
| 3/16/2016 | Listed for sale | $2,750,000-57.7%$729/sqft |
Source: Point B Realty #21602114 Report a problem | ||
| 3/5/2015 | Listing removed | $6,500,000$1,724/sqft |
Source: Lighthouse Properties #21410077 Report a problem | ||
| 2/6/2015 | Listed for sale | $6,500,000+722.1%$1,724/sqft |
Source: Lighthouse Properties #21410077 Report a problem | ||
| 12/9/2011 | Sold | $790,625-20.5%$210/sqft |
Source: LINK #21320 Report a problem | ||
| 5/14/2011 | Listed for sale | $995,000$264/sqft |
Source: Sandpiper Realty, Inc. Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $8,329 +13.4% | $3,143,000 +9.1% |
| 2024 | $7,344 +5.3% | $2,879,900 +4.1% |
| 2023 | $6,975 +14.2% | $2,767,700 +37.3% |
| 2022 | $6,107 -11.2% | $2,015,582 -3.9% |
| 2021 | $6,876 +2% | $2,096,333 +4.2% |
| 2020 | $6,740 -2.3% | $2,012,007 +12.8% |
| 2019 | $6,901 +47.4% | $1,783,200 +47.4% |
| 2018 | $4,681 +8.8% | $1,209,500 -0.2% |
| 2017 | $4,304 +24% | $1,212,300 +26.5% |
| 2016 | $3,470 -4% | $958,700 -7.9% |
| 2015 | $3,613 +8.7% | $1,041,100 +15.9% |
| 2014 | $3,325 +29.6% | $898,600 +24.3% |
| 2013 | $2,566 +3.5% | $722,900 |
| 2012 | $2,480 -14.2% | $722,900 -15% |
| 2011 | $2,892 +10% | $850,700 |
| 2010 | $2,629 +3.1% | $850,700 -2.9% |
| 2009 | $2,550 +5.4% | $876,200 -1.1% |
| 2008 | $2,419 -11.1% | $886,000 -7.2% |
| 2007 | $2,720 -3.2% | $954,300 +2.9% |
| 2006 | $2,811 +3.2% | $927,800 +3.9% |
| 2005 | $2,725 +37.1% | $893,400 +57.8% |
| 2004 | $1,988 -12% | $566,300 +56.4% |
| 2000 | $2,260 | $362,200 |
Find assessor info on the county website
Monthly payment
Est. payment
$16,218/mo
Principal & interest
$14968
Property taxes
$1250
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Climate risks
Neighborhood: 02539
Nearby schools
GreatSchools rating
- 7/10Edgartown Elementary SchoolGrades: PK-8Distance: 2.2 mi
- 6/10Martha's Vineyard Regional High SchoolGrades: 9-12Distance: 6.5 mi
Local experts in 02539
- Massachusetts
- Dukes County
- Edgartown
- 02539
- 72 Chappaquiddick Ave
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