Move-in ready Edgartown home in a quiet, established neighborhood just minutes from downtown. This year-round property 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 guest house 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. 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.
For sale
$3,895,000
44 Plantingfield Way, Edgartown, MA 02539
4beds
2,243sqft
Est.:
Single Family Residence
Built in 1978
0.53 Acres Lot
$2,150,500 Zestimate®
$1,737/sqft
$-- HOA
What's special
Thoughtful layoutLarge level lotFunctional living spaces
- 3 days |
- 581 |
- 15 |
Zillow last checked: 8 hours ago
Listing updated: December 08, 2025 at 03:41pm
Listed by:
David Dickinson,
Compass | Point B
Source: LINK,MLS#: 41585
Tour with a local agent
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: 2,243
- Total interior livable area: 2,243 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: $1,737/sqft
- Tax assessed value: $2,207,100
- Annual tax amount: $5,258
- Date on market: 12/8/2025
- Listing agreement: E
Estimated market value
$2,150,500
$1.83M - $2.49M
$3,143/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 12/8/2025 | Listed for sale | $3,895,000$1,737/sqft |
Source: MLS PIN #73460777 Report a problem | ||
Public tax history
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% |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$22,827/mo
Principal & interest
$19841
Property taxes
$1623
Home insurance
$1363
Climate risks
Neighborhood: 02539
Nearby schools
GreatSchools rating
- 7/10Edgartown Elementary SchoolGrades: PK-8Distance: 0.4 mi
- 5/10Martha's Vineyard Regional High SchoolGrades: 9-12Distance: 4.4 mi
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