Linda Akers
Associate Real Estate Broker
REALTOR®, CBR
BEDS6
BATHS3 full
SQUARE FEET5,900
MLS#1005789
STATUSActive
PROPERTY TYPEResidential - Single Family
SCHOOLContact Agent
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.
Property Features
Property Type: Residential - Single Family
Cooling: Wall/Window Unit(s)
Heating: Baseboard
Home Style: Cottage
Lot Size: 0.12 Acres
Taxes: $7,523
Year Built: 1980
Amenities
Beamed Ceilings
Original Details
Feature Descriptions
Appliances: Stainless Steel Appliance(s), Washer
Building Area Total: 5900
Exterior: Frame
Fireplace Y/N: Yes
On Market Date: 2026-05-29
Parcel Number: 0700-005-00-05-00-017-001
Parking Features: Driveway
Rental Term: Monthly
Rooms Total: 6
Sewer: Septic Tank
Utilities: Electricity Available
Water: Private
Waterfront Features: Lake Front
Local Schools
High School: Contact Agent
Elementary School: Contact Agent
School District: Contact Agent
Estimate Your Payment
Estimated Payment
$ 15,067.09 per month $13,652.67 Principal & Interest $626.92 Property Tax $787.50 Homeowner's InsuranceChange Payment Information
Listed By / Shown By
Listing By
Agency Name: Compass Greater NY LLC
Agency Contact: 917-499-2824
Shown By
Agent Name: Linda Akers
Agent Phone: (516) 365-5780
Agency Title: Coldwell Banker American Homes
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2 Prospect Avenue | MLS# 1005789
This single family home located at 2 Prospect Avenue, Shelter Island, NY 11964 is currently listed for sale with an asking price of $2,700,000. This property was built in 1980 and has 6 bedrooms and 3 full baths with 5900 sq. ft. Prospect Avenue is located within the Contact Agent school district. Search Shelter Island real estate on lindaakers.cbamhomes.com today.