$2,700,000

2 Prospect Avenue, Shelter Island, NY 11964

  • 6 beds |
  • 3 baths |
  • 5,900 sqft
  • Property Icon Single-Family Home
  • Property Year Built Icon Built in 1920
  • Property Lot Size Icon2.43acre lot
  • Property Parking Icon —— car garage
  • Property Price Per Square Feet Icon $458/sqft
  • Property List Date Icon Listed 29 days ago

Property Description

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 been carefully renovated to enhance modern comfort while maintaining the craftsmanship and warmth of its era. Completing the offering, the adjacent lot at Rock Point Road presents a rare blank canvas, ready for a primary residence and pool, surrounded by three established rental cottages. Whether envisioned as a private multi-generational retreat, a boutique rental compound, or a long-term development investment, this is a truly exceptional opportunity to own a piece of Shelter Island’s history with both immediate income and enduring upside in one of Long Island’s most sought-after enclaves.

Listing Status:
Active
Data Last Updated:
June 26, 2026 at 9:21PM
Listing Office:
Compass Greater NY LLC : 917-499-2824
MLS ID:
1005789
  • General: Beamed CeilingsOriginal Details
  • Appliances: Stainless Steel Appliance(s)Washer
  • A/C: Wall/Window Unit(s)
  • Heating: Baseboard
  • Fireplace: Fireplace
  • Style: Cottage
  • Parking: Driveway
  • Originating MLS: onekey2
  • School District: Contact Agent
  • County: Suffolk County
  • Zoning: 0700-005-00-05-00-017-001
  • Utilities: Electricity Available
  • Water: Private
  • Sewer: Septic Tank
  • Source: onekey2

This listing courtesy of Compass Greater NY LLC

Monthly Payment

$Est. Payment
  • Principal & Interest $
  • Property Taxes $
  • Home Insurance $
  • VA Funding Fee $

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