36 Smith Hollow Dr, Edgartown, MA 02539

Local realty services provided by:Better Homes and Gardens Real Estate The Masiello Group
36 Smith Hollow Dr,Edgartown, MA 02539
$1,985,000
  • 4 Beds
  • 3 Baths
  • 2,836 sq. ft.
  • Single family
  • Active
Listed by: katie donahue & rachel serwa group, katie donahue & rachel serwa group
Office: sandpiper realty, inc.
MLS#:73472940
Source:MLSPIN

Price summary

  • Price:$1,985,000
  • Price per sq. ft.:$699.93

About this home

Tucked away behind association common land, this year-round compound offers the perfect blend of privacy, space, and flexibility. The post-and-beam main house features four bedrooms and combines timeless character with functional design, ideal for everyday living or seasonal enjoyment. A separate two-bedroom guest house with a welcoming farmer's porch is thoughtfully sited to ensure privacy and independence, complete with its own driveway and parking. The detached garage, with a loft above, adds even more versatility—ideal for storage or future finished space. Situated on one of the largest parcels in the Smith Hollow Association, the property enjoys a tranquil, park-like setting. With direct access to the bike path at the end of the road, you're just minutes from Edgartown and all down-island amenities. More than just a house—this is a place to call home.

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Home facts

  • Year built:1985
  • Listing ID #:73472940
  • Updated:January 30, 2026 at 07:53 PM

Rooms and interior

  • Bedrooms:4
  • Total bathrooms:3
  • Full bathrooms:2
  • Half bathrooms:1
  • Living area:2,836 sq. ft.

Heating and cooling

  • Cooling:Wall Unit(s), Window Unit(s)
  • Heating:Baseboard, Natural Gas

Structure and exterior

  • Roof:Shingle
  • Year built:1985
  • Building area:2,836 sq. ft.
  • Lot area:1.7 Acres

Utilities

  • Water:Private
  • Sewer:Private Sewer

Finances and disclosures

  • Price:$1,985,000
  • Price per sq. ft.:$699.93
  • Tax amount:$5,249 (2026)
The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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