2 Prospect Avenue,Shelter Island, NY 11964
Shelter Island, NY 11964
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.
Details
| MLS # | 1005789 |
|---|---|
| Listing Type | For Sale |
| Style | House |
| Sub-Type | Resale |
| Status | Active |
| Year | 1920 |
| Days On Site | 104 |
| Listing Provided By | Compass Greater NY LLC | Marco L. Maida |
Features
| Bed(s) | 6 |
|---|---|
| Bath(s) | 3 Total |
| SQ Feet | 5,900 |
| Acreage | 2.43 |
| Water Front | Yes |
Interior
| Cooling | Wall/Window Unit(s) |
|---|---|
| Heating | Baseboard |
| Interior Features | Beamed Ceilings, Original Details |
| Appliances | Stainless Steel Appliance(s), Washer |
Exterior
| Construction Materials | Frame |
|---|
Parking
| Garage Yes / No | No |
|---|---|
| Parking Features | Driveway |
Utilities
| Utilities | Electricity Available |
|---|---|
| Sewer | Septic Tank |
Taxes
| Tax Year | 2025 |
|---|---|
| Tax Annual Amount | 7523 |
Area Information
| State | NY |
|---|---|
| County | Suffolk County |
| City | Shelter Island |
| Zip Code | 11964 |
| School District | Contact Agent |
| Elementary School | Contact Agent |
| High School | Contact Agent |
| Listing VS Median (in 11964) | |
Price: $2,700,000 low | high Med: $1,999,999 sqft: 5,900 low | high Med: 2,777 $ / sqft: $458 low | high Med: $720 On site: 104 low | high Med: 134 | |
Market Activity 11964
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Learn More About This Property
| State | NY |
|---|---|
| County | Suffolk County |
| City | Shelter Island |
| Zip Code | 11964 |
| School District | Contact Agent |
| Elementary School | Contact Agent |
| High School | Contact Agent |
| Listing VS Median (in 11964) | |
Price: $2,700,000 low | high Med: $1,999,999 sqft: 5,900 low | high Med: 2,777 $ / sqft: $458 low | high Med: $720 On site: 104 low | high Med: 134 | |
