2 Prospect Ave | Image 1
2 Prospect Ave | Image 2
2 Prospect Ave | Image 3
2 Prospect Ave | Image 4
2 Prospect Ave | Image 5
2 Prospect Ave | Image 6
2 Prospect Ave | Image 7

$2,700,000

For Sale

11 days ago

2 Prospect Ave, Shelter Island, NY

House

MLS® 1005789

6 Bed

3 Bath

5900 sqft

--

  • Key Facts
  • Description
  • Map

Key Facts

Type Single Family Residence
Levels Residential
Size 5900 sqft
Garage 
Taxes $7,523
Days Active 10
Lot Size 
Approx. Age 1920
Avg. Price Per Sqft $457
MLS® Number 1005789

Property Address: 2 Prospect Ave, Shelter Island, NY, 11964

Average square foot calculated using Size range provided by listing agent.

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.
MLS® Number1005789
Laundry Level
Central VacNo
FireplaceNo
Acreage
Exterior
Garage
Approx. Age1920
Basement
DrivewayDriveway
Garage Spaces
Heat
A/C
Heating Fuel

Extras

Price History

-End Date
Not Sold YetSold Price

For Sale

May 29, 2026List Date
$2,700,000List Price
  • Commute

Commute

Starting Address
Destination Address
2 Prospect Ave, Shelter Island, NY

Like what you see?

Complete the form and we'll be in touch. No login necessary.

Add a Comment
Loading...

Similar Listings

Comparable Properties