2 Prospect AVE, Shelter Island, NY 11964
2 Prospect AVE, Shelter Island, NY 11964
2 Prospect AVE, Shelter Island, NY 11964
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$2,700,000
Est. payment /mo
6 Beds
3 Baths
5,900 SqFt
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Key Details

Property Type Single Family Home

Sub Type Single Family Residence

Listing Status Active

Purchase Type For Sale

Square Footage 5,900 sqft

Price per Sqft $457

MLS Listing ID 1005789

Style Cottage

Bedrooms 6

Full Baths 3

HOA Y/N No

Rental Info No

Year Built 1920

Annual Tax Amount $7,523

Lot Size 2.425 Acres

Acres 2.425

Property Sub-Type Single Family Residence

Source onekey2

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.

Location

State NY

County Suffolk County

Interior

Interior Features Beamed Ceilings, Original Details

Heating Baseboard

Cooling Wall/Window Unit(s)

Fireplace No

Appliance Stainless Steel Appliance(s), Washer

Exterior

Parking Features Driveway

Utilities Available Electricity Available

Waterfront Description Lake Front

Garage false

Private Pool No

Building

Sewer Septic Tank

Water Private

Structure Type Frame

Schools

Elementary Schools Contact Agent

Middle Schools Call Listing Agent

High Schools Contact Agent

School District Contact Agent

Others

Senior Community No

Special Listing Condition None


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OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
Listed by Compass Greater NY LLC • Marco L. Maida

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Christine Sardinha

Christine Sardinha

+1(718) 404-4132

Broker Associate | License ID: 10301202073

Broker Associate License ID: 10301202073

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