2 Prospect Ave
Listing Notes
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.
Price in context
Cheaper than 33% of the 24 homes listed nearby right now, which run $1,495,000 to $3,850,000.
See all 24 nearby listings
| Address | Asking | Size |
|---|---|---|
| 6 Oxford Ave | $1,495,000 | 4 bd · 2 ba |
| 5 Spring Garden Ave | $1,500,000 | 5 bd · 3 ba |
| 66A N Midway Rd | $1,545,000 | 2 bd · 3 ba |
| 311 5th St | $1,579,000 | 3 bd · 2 ba |
| 215 North St | $1,595,000 | 7 bd · 6 ba |
| 4 Quail Hedge Ln | $1,795,000 | 3 bd · 3 ba |
| 73 N Midway Rd | $1,845,000 | 4 bd · 3 ba |
| 1025 9th St | $1,849,000 | 4 bd · 3 ba |
| 7 Locust Ave | $1,850,000 | 4 bd · 2 ba |
| 4 Bayview Ave | $1,999,999 | 6 bd · 6 ba |
| 151 Bay Ave | $2,100,000 | 5 bd · 5 ba |
| 64A N Midway Rd | $2,199,000 | 5 bd · 4 ba |
| 64 Midway Rd | $2,199,000 | 5 bd · 4 ba |
| 14 Freds Ln | $2,485,000 | 6 bd · 4 ba |
| 11 Prospect Ave | $2,595,000 | 4 bd · 3 ba |
| 11 Prospect Ave | $2,595,000 | 3 bd · 3 ba |
| 31 Manhanset Rd | $2,895,000 | — |
| 12 Terry Dr | $2,950,000 | 5 bd · 5 ba |
| 11 Freds Ln | $3,200,000 | 5 bd · 5 ba |
| 13 Tower Hill Ave | $3,250,000 | 4 bd · 3 ba |
| 24 Rocky Point Rd | $3,290,000 | 4 bd · 3 ba |
| 9 Locust Woods Dr | $3,499,000 | 4 bd · 4 ba |
| 7 Locust Woods Dr | $3,750,000 | 6 bd · 7 ba |
| 8 Hilo Dr | $3,850,000 | 4 bd · 6 ba |
Where it is
For sale Coming soon Recently sold— zoom out for more
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