2 Prospect Avenue, Shelter Island, NY 11964

Shelter Island
Local realty services provided by:ERA Caputo Realty
2 Prospect Avenue,Shelter Island, NY 11964
$2,700,000
  • 6 Beds
  • 3 Baths
  • 5,900 sq. ft.
  • Single family
  • Active
Listed by: marco l. maida, carl m. gambino
Office: compass greater ny llc.
MLS#:1005789
Source:OneKey MLS

Price summary

  • Price:$2,700,000
  • Price per sq. ft.:$457.63

About this home

A rare opportunity to own a legacy compound on Shelter Island, this offering brings together three income-producing historic cottages and a separate buildable lot, all just moments from the water. Positioned at 2 Prospect Avenue and 38 Rock Point Road, the properties are offered as one cohesive investment, blending immediate revenue with exceptional future potential. Each of the three cottages features two bedrooms and one bath, with strong summer rental histories and an undeniable sense of place rooted in the island’s coastal charm. Rich in character and provenance, each residence tells its own story. The Hill Cottage, dating to the 1890s, is a one-of-a-kind former boathouse thoughtfully relocated from a grand Nostrand Avenue estate, with original architectural details preserved throughout. The Red Cottage, originally built in the 1920s as a fisherman’s retreat, has been expanded to include enclosed patios at both the front and rear. The Main House, constructed in the 1940s, has...

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Home facts

  • Year built:1920
  • Listing ID #:1005789
  • Added:107 day(s) ago
  • Updated:September 14, 2026 at 11:13 AM

Rooms and interior

  • Bedrooms:6
  • Total bathrooms:3
  • Full bathrooms:3
  • Rooms Total:6
  • Kitchen Description:Stainless Steel Appliance(s)
  • Living area:5,900 sq. ft.

Heating and cooling

  • Heating:Baseboard

Structure and exterior

  • Year built:1920
  • Building area:5,900 sq. ft.
  • Lot area:2.43 Acres
  • Architectural Style:Cottage
  • Construction Materials:Frame

Schools

  • High school:Contact Agent
  • Middle school:Call Listing Agent
  • Elementary school:Contact Agent

Utilities

  • Water:Private
  • Sewer:Septic Tank

Finances and disclosures

  • Price:$2,700,000
  • Price per sq. ft.:$457.63
  • Tax amount:$7,523 (2025)

Features and amenities

  • Appliances:Stainless Steel Appliance(s), Washer
  • Laundry features:Washer

Parking

  • Parking description:Driveway
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