2 Prospect Avenue, Shelter Island, NY 11964
Suffolk County
Key Facts
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 Information
Property Type
Residential
Sub-Type
Single Family Residence
Style
Cottage
Year Built
1920
Living Area
5,900 sq ft
Lot Size
2.42 acres
Days on Market
5
MLS® Listing#
1005789
Property Features
Interior
Appliances
Cooling
Heating
Parking
Construction
Utilities
Sewer
Water Source
Schools
- Elementary:
- Contact Agent
- Middle:
- Call Listing Agent
- High:
- Contact Agent
Financial Details
Annual Taxes
$7,523
Parcel Number
0700-005-00-05-00-017-001
Affordability Calculator
$540,000
Estimated monthly payment
$14,371/mo
Principal $2,160,000 · Est. interest $3,013,392 over 30 yrs
Neighborhood Market Statistics
How this home compares to active listings in Shelter Island, NY
- $842,857
- Median Listing Price
- 53
- Median Days on Market
- 1,600
- Median Sq Ft
- $482
- Median Price / Sq Ft
- 594
- Active Listings
- This home’s price is 220% above the area median.
- Its price per sq ft is 5% below the area median.
Market statistics compiled from active EXIT Realty® and MLS listings in Shelter Island, NY.
Location
- 2 Prospect Avenue, Shelter Island, NY 11964
Points of Interest in Shelter Island, NY
Showing the Shelter Island area map.
Nearby Schools
Shelter Island School
School · 1.4 mi away
Greenport Elementary School
Elementary · 1.5 mi away
Southold Elementary School
Elementary · 4.2 mi away
Southold Junior Senior High School
Secondary · 4.2 mi away
Head Start
School · 4.8 mi away
Oysterponds Elementary School
Elementary · 5.2 mi away
Sag Harbor Elementary School
Elementary · 6.9 mi away
Sag Harbor Union Free School District Page
School · 7.0 mi away
Pierson High School
Secondary · 7.0 mi away
Cutchogue East Elementary School
Elementary · 7.2 mi away
Harbor Waldorf School
School · 7.3 mi away
Our Sons and Daughters
School · 7.3 mi away
Mattituck-Cutchogue School Dist
School · 8.3 mi away
Our Lady of Mercy Elementary School
Elementary · 8.5 mi away
New Suffolk School
Elementary · 8.8 mi away
Ross Lower School
School · 9.1 mi away
The Green School
School · 9.8 mi away
Ross School
Elementary · 9.8 mi away
Hayground School
School · 10.0 mi away
Bridgehampton School
School · 10.5 mi away
Commute Calculator
Nearby Homes
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| Address | Price | Beds | Baths | Sq Ft |
|---|---|---|---|---|
| 287 Bay Walk, Fire Island Pines, NY | $1,899,000 | 5 | 5 | 2,456 |
| 45 Poe Street, Staten Island, NY | $1,899,000 | 6 | — | 4,680 |
| 544 Falcon Avenue, Staten Island, NY | $1,900,000 | 5 | — | 3,712 |
| 296 Edgewater Street, Staten Island, NY | $1,980,000 | 5 | — | 2,625 |
| 34-25 24 Street, Long Island City, NY | $2,100,000 | 6 | 3 | 3,036 |
| 317 Sky Walk, Fire Island Pines, NY | $2,150,000 | 7 | 6 | 3,444 |
Moving Cost Estimate
EXIT Agents in Shelter Island
Listing Courtesy: Compass Greater NY LLC - 6312518644
Presented by: Marco L. Maida
Fair Housing Notice