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44 Plantingfield Way

$3,895,000

Downtown, Edgartown, MA 02539

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Single Family Residence in Downtown, Edgartown

4 bedrooms

·

2 bathrooms

·

2243 SqFt

·

0.53 acres

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MLS #41585

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.

Property highlights

Unfurnished

Deck

Garden

Public Beach

Porch

Septic Tank

Cable

Town Water

Property Details

Association Fee:
0
Association Fee Includes:
Basement:
Unfinished space with a concrete door; accessible from outside via a bulkhead door.
Fireplace Features:
1
Flooring:
1.5
Foundation Types:
Poured concrete
Frontage Type:
None
Heating:
OFHW
Interior Features:
AC,Ins,MiniSplit,OSh,WdStoveFloor 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.
Link MLS Comments:
From Main Street, take Peases Point Way North and follow to Plantingfield Way. Property is 0.2 miles down Plantingfield Way on left.
Lot Features:
Parking Features:
5 spaces
Possible Use:
Assessed Building Value:
1188300.00
Assessed Land Value:
1018800.00

Price History

December 08, 2025
$3,895,000

Tax Information

This property was most recently assessed in 2025. It has been assessed at a value of $2,207,100. The annual tax responsibility for this property is $5,258.

Contact an Agent
Phone number
(508) 696-7777

Property Location

©2022 LINK, All Rights Reserved. Not responsible for misinformation or typographical errors. Prices are subject to change without notice. Listed by Compass | Point B.