Edgartown, MA 02539 37 Plain Field Way

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Presented By: Wendy Harman with Compass | Point B - 508-274-5363
  • MLS# 44835
  • 08/17/2026
  • Request Tour
  • Request Info
  • Beds • 5
  • Full/Half Baths • 4 / 2
  • SQFT • 3,606

Home Details

SOPHISTICATED KATAMA RETREAT WITH POOL AND CUSTOM FINISHES. Tucked at the end of a lightly traveled road, this modern farmhouse offers an exceptional combination of sophisticated design, generous living spaces, and complete backyard privacy. Working closely with the builder, the owners thoughtfully incorporated custom design elements and elevated finishes throughout the home, creating a residence that feels both distinctive and effortlessly livable. A dramatic wall of glass fills the open-concept great room with natural light and creates a seamless connection to the outdoor entertaining spaces. Designed for everyday comfort as well as memorable gatherings, the main level features spacious living and dining areas anchored by a gas fireplace and custom built-ins. The chef’s kitchen is equally impressive, with marble countertops, commercial-style stainless and integrated appliances, an oversized center island, beverage refrigerator, and a wall of sliding glass panels that opens to a poolside bar. A luxurious first-floor primary suite, private office, laundry area, and powder room complete this level. The home offers five bedrooms and four-and-one-half baths, including a second en suite primary bedroom on the upper level. Two additional upstairs bedrooms share a thoughtfully designed Jack-and-Jill bath, while the finished lower level provides a fifth bedroom, full bath, and expansive game and media room with pool and ping-pong tables—creating flexible space for guests, recreation, or extended stays. Outside, the property transforms into an entirely private, resort-style retreat. A heated 16-by-38-foot gunite saltwater pool with a generous sun shelf is surrounded by an expansive bluestone patio, multiple lounge and dining areas, a fire table, and a separate wood-burning fire pit. Manicured grounds, thoughtful landscaping, an enclosed outdoor shower, and broad lawn areas complete the setting. In addition to its appeal as a refined island residence, the property has a strong rental income history, offering an attractive opportunity for buyers seeking both personal enjoyment and investment potential. The home is being offered turnkey with indoor and outdoor furnishings, allowing the next owner to begin enjoying the property—or continue its successful rental use—with ease.
Presented By: Wendy Harman with Compass | Point B - 508-274-5363

Interior Features for 37 Plain Field Way

Bedrooms

Main Level Bedrooms1
Total Bedrooms5

Bathrooms

Half Baths2

Other Interior Features

BasementThe Lower Level offers a TV/Game Room with sofa seating, large screen TV, ping pong and pool table, plus game table, and a custom-built children's Play Area with double dutch doors located under the stairs. The fifth Bedroom is located on the Lower Level with a full shared bath.
Fireplace FeaturesGas Fireplace In Living Room
Fireplace Y/NNo
FlooringHardwood + Tile
Furnished Y/NFurnished
Interior AmenitiesA, AC, Ins, Irr, OSh, Floor 1: The first-floor has an open design Great Room with Living, Dining, and Kitchen Areas. A wall of glass windows and sliding doors frames one side of the light-filled room. The Living Area anchors one end of the room with sofa seating, gas fireplace with built-ins, and 70" large screen TV, while the Gourmet Kitchen anchors the other end. Just off the Kitchen is the Dining Area, which is framed by two walls of custom built-in cabinets. The Chef's Kitchen has a large center prep island/breakfast bar, commercial stainless and cabinet-fronted appliances, quartz counters, beverage refrigerator, plus a sliding wall of glass panels that open as a pass-thru to the outside deck and pool area with bar and four seats. There is also a first-floor Primary Bedroom with deluxe Primary Bath, and small office, plus one of two Laundry Areas, and a Powder Room., Floor 2: The second floor features three bedrooms, including a second Primary Bedroom with en suite bath and desk/work area, plus a shared Jack and Jill Bathroom for the other two bedrooms.

General for 37 Plain Field Way

AppliancesStove: Wolf® Gas Range, Washer: Yes
Assoc Fee Paid PerMonthly
Building Area UnitsSquare Feet
CityEdgartown
Full Baths4
HeatingGFHA
Lot Size Square Feet41817
MLS Area2
Property SubtypeSingle Family Residence
Property Type1 Family
SewerTwn
Standard StatusActive Under Contract
StatusC
Tax Annual Amount8190.48
Tax Assessed Value2604800
Tax Lot32.21
Tax Year2026
TaxOtherAnnualAssessmentAmount697800
Total Rooms8
UtilitiesCbl
ViewNone, Res
Year Built2021
ZoningR20

Exterior for 37 Plain Field Way

Building Area Total3606
Exterior AmenitiesDeck, P/Pool, PubBch
Foundation DetailsPoured Concrete
Frontage TypeNone
Lot FeaturesProfessionally Landscaped Yard
Lot Size Acres0.96
Lot Size Area0.96
Parking FeaturesAmple On-Site Parking
Water SourceWell

Additional Details

Price History

Janna O'Loughlin

Sales Associate Representing Sellers & Buyers
Price $5,795,000
MLS#44835
List Date 08/17/2026
Property Type Single Family
Phone 508.272.4819
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