Post-and-beam style Edgartown home in a quiet, established neighborhood just minutes from downtown. This year-round home offers functional living spaces, a thoughtful layout, and generous outdoor areas ideal for relaxing or entertaining. Currently configured with a 3BR/1.5BA main house and 1BR/1BA accessory apartment over a one-car garage, this property affords multiple options for would-be buyers. The existing structures could be reconfigured and updated to meet a buyer's specific needs, while the large level lot also presents an excellent opportunity for those looking to start new and create a brand new, custom island retreat or private oasis complete with a pool. This property can be connected to town sewer and support up to six bedrooms with a grandfathered guest house. Located close to shops, restaurants, beaches, and the harbor, the home provides a perfect blend of convenience and privacy — ideal for year-round living, vacation use, or rental potential in one of Edgartown’s most sought-after areas.
Pending
$3,895,000
44 Plantingfield Way, Edgartown, MA 02539
4beds
2,300sqft
Est.:
Single Family Residence
Built in 1978
0.53 Acres Lot
$3,633,200 Zestimate®
$1,693/sqft
$-- HOA
What's special
Thoughtful layoutPost-and-beam style edgartown homeLarge level lotFunctional living spaces
- 85 days |
- 122 |
- 0 |
Zillow last checked:
Listing updated:
Listed by:
David Dickinson,
Compass | Point B
Source: LINK,MLS#: 41585
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Heating
- OFHW
Appliances
- Included: Stove: Frigidaire, Washer: LG
Features
- AC, Ins, MiniSplit, OSh, WdStove, Floor 1: The first floor is designed for effortless flow, showcasing wide pine plank flooring throughout, with a spacious kitchen and dining area opening into a warm, fireplace-centered living room. A rear laundry area, located next to a discreet half bath, adds everyday convenience., Floor 2: The second floor includes a generous primary bedroom, two well-sized additional bedrooms, and a roomy shared full bathroom., Floor 3: Attic space accessible via a pull-down staircase provides room for additional storage as well as second floor HVAC equipment.
- Flooring: 1.5
- Basement: Unfinished space with a concrete door; accessible from outside via a bulkhead door.
- Fireplace features: 1
Interior area
- Total structure area: 2,300
- Total interior livable area: 2,300 sqft
Property
Parking
- Parking features: 5 spaces
Features
- Exterior features: Deck, Garden, PubBch, Porch
- Has view: Yes
- View description: None
- Frontage type: None
Lot
- Size: 0.53 Acres
Details
- Additional structures: Storage shed (12x16) Solar panels on roof of main house (installed 2019)
- Parcel number: 101
- Zoning: R20
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Foundation: Poured concrete
Condition
- Year built: 1978
- Major remodel year: 2016
Utilities & green energy
- Sewer: Septic Tank
- Water: Town
- Utilities for property: Cbl
Community & HOA
Location
- Region: Edgartown
Financial & listing details
- Price per square foot: $1,693/sqft
- Tax assessed value: $2,207,100
- Annual tax amount: $5,258
- Date on market: 12/8/2025
- Listing agreement: E
Estimated market value
$3,633,200
$3.45M - $3.81M
$7,804/mo
Price history
| Date | Event | Price |
|---|---|---|
| 3/31/2026 | Pending sale | $3,895,000$1,693/sqft |
Source: LINK #41585 Report a problem | ||
| 2/28/2026 | Contingent | $3,895,000$1,693/sqft |
Source: MLS PIN #73460777 Report a problem | ||
| 12/8/2025 | Listed for sale | $3,895,000$1,693/sqft |
Source: MLS PIN #73460777 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $5,849 +12.1% | $2,207,100 +7.9% |
| 2024 | $5,216 +5.8% | $2,045,500 +4.5% |
| 2023 | $4,930 +20.4% | $1,956,500 +44.8% |
| 2022 | $4,093 +1.3% | $1,350,800 +9.6% |
| 2021 | $4,041 +6.5% | $1,232,100 +8.8% |
| 2020 | $3,794 -18.4% | $1,132,400 -5.7% |
| 2019 | $4,649 +7.4% | $1,201,200 +7.4% |
| 2018 | $4,328 +35.5% | $1,118,400 +24.3% |
| 2017 | $3,193 +0.6% | $899,400 +2.6% |
| 2016 | $3,174 +3.4% | $876,900 -0.8% |
| 2015 | $3,069 -15.1% | $884,400 -9.5% |
| 2014 | $3,614 +3.9% | $976,700 -0.3% |
| 2013 | $3,479 +3.5% | $980,100 |
| 2012 | $3,362 -3% | $980,100 -3.8% |
| 2011 | $3,465 -8.8% | $1,019,000 -17.1% |
| 2010 | $3,800 +2.8% | $1,229,800 -3.1% |
| 2009 | $3,695 +6.6% | $1,269,600 |
| 2008 | $3,466 +8.9% | $1,269,600 +13.7% |
| 2007 | $3,183 -3.2% | $1,116,700 +2.9% |
| 2006 | $3,288 +18.8% | $1,085,100 +19.6% |
| 2005 | $2,768 -12% | $907,400 +1.3% |
| 2004 | $3,145 +8.3% | $896,100 +13.6% |
| 2003 | $2,903 +16.4% | $788,900 +62.5% |
| 2001 | $2,495 +1.2% | $485,500 +22.9% |
| 2000 | $2,465 | $395,000 |
Find assessor info on the county website
Monthly payment
Est. payment
$21,216/mo
Principal & interest
$19593
Property taxes
$1623
More affordability tools
Climate risks
Neighborhood: 02539
Nearby schools
GreatSchools rating
- 7/10Edgartown Elementary SchoolGrades: PK-8Distance: 0.4 mi
- 6/10Martha's Vineyard Regional High SchoolGrades: 9-12Distance: 4.4 mi
A local agent can set up tours, give advice and negotiate with sellers.
A local lender can help you make sure your offer is ready when you are.
- Massachusetts
- Dukes County
- Edgartown
- 02539
- 44 Plantingfield Way
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