Penelope Moore
Penelope A. Moore
Shelter Island Real Estate
Licensed Associate Real Estate Broker

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$3,672,000 Active

28 South Menantic Road
Shelter Island, NY 11964

4 beds, | Residential
4,174 sq ft - MLS# 10509298
Property Photo


1888 TRADITIONAL WITH ENGLISH GARDENS, POOL AND COTTAGES Once the cherished home of a respected art critic, and originally built by a local sea captain, this handsome traditional, is a singular opportunity on Shelter Island. Set on two sweeping acres, the gardens were designed with courtyards, walkways, established flowering shrubs, herb gardens and, in a nod to the history of the property which was once a farm, a fruit orchard with apple, apricot, peach, cherry and pear trees. Originally built in 1888 and re-designed by Lee Skolnik, the main home which was renovated in the late 1980's, totals 4,174+/- sq. ft. There are many intricate architectural details, including high coffered ceilings, a grand Hollywood style staircase, and modified rose windows. The entry foyer leads to the living room which has doors to the garden and extends from front to back of the home, with a wood burning fireplace and adjacent formal dining room. The kitchen features high end appliances and a walk-in butler's pantry with half bath. Toward the opposite side of the foyer are a powder room, laundry room, sitting room/study. The second floor has a landing with a walkway to the second floor of the neighboring carriage house, two en-suite guest bedrooms and a magnificent master suite, which offers an office, spa-like bath, built-in wardrobes, private living room and outdoor deck. There is a covered porch for relaxation, with views to the rose trellises, herb garden, raised vegetable gardens and orchard. The 960+/- sq. ft. carriage house has a gym, playroom and library, as well as a carpentry shop. Through the gardens, a series of formal spaces, strategically placed, paths lead to sweet meditation areas--including the 18' x 60' in-ground pool with approximately 1,410+/- sq. ft. bluestone patio, 180+/- sq. ft. cabana and 840+/- sq. ft. one bedroom cottage. A vestige of the original property, a 660+/- sq. ft. cabin, which is well maintained and now serves as a potting shed, is adjacent to a gated vegetable garden.


  • Basement: Full
  • Deck: Yes
  • Fireplace: Yes
  • Garage: Detached, 1.5 spaces
  • Heating/Cooling: OHW Heat, Wall/Window Units
  • Levels: 2
  • List Date: 05/28/2018
  • Lot Size: 2.00
  • Pool: In ground, Vinyl
  • School District: Shelter Island
  • Type: Single Family
  • Year Built: 1888
  • View: Mainland
Penelope A. Moore
Shelter Island Real Estate

PO Box 1034
Shelter Island Heights, NY
Mobile: 917-208-5519
Office: 631-749-5801
Fax: 631-204-6947 
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A Standard of Excellence Your First Choice in Shelter Island Real Estate


We had been looking for over 2 years, in part because there was not a lot on the market and in part because we had very specific requirements. Penelope was the first broker I ever met who actually listened to what those requirements were and acted on them. After several intensive days searching she understood what we needed. For the following few months we heard from her on a regular basis but there was nothing worth making a special journey out from the city for. Then finally she found a house that you could tell was important to see asap and this was the house we bought. Having found it and agreed on the price, I was keen to close asap to make sure I didn’t have to spend another 2 years looking and Penelope worked round the clock to get things done. We’ve now lived here for two years and regularly keep in touch with Penny socially. She is definitely more than your regular real estate broker... 
A.C. New York, NY
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