For Sale

Listed by Marco Maria Maida and Carl Gambino

Source: OneKey #1005789

2 Prospect Ave, Shelter Island Heights, NY, 11965

$2,700,000

6
3
5900 sq. ft.
5227 sq. ft.

SingleFam

1 day on the market

What's around 2 Prospect Ave

About this property

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.

Looking for more information on 2 Prospect Ave?

Explore comparables, sales history and growth for this property.
Learn more

Contact

Similar properties for sale nearby

For Sale
$1,990,000
4 Bayview Avenue
Shelter Island Heights NY 11965
6
6
2
Single-Family
Listing courtesy of Joseph W Johns
For Sale
$4,995,000
189 Ram Island Drive
Shelter Island Heights NY 11965
6
7
Single-Family
Listing courtesy of Daniel Gale Sotheby's International Realty

Other properties for sale by Compass Greater NY LLC

For Sale
$10,250,000
5055 New Suffolk Road
New Suffolk NY 11935
5
6
3
Single-Family
Listing courtesy of Compass Greater NY LLC
For Sale
$1,565,000
8579 New Suffolk Avenue
Cutchogue NY 11935
4
4
1
Single-Family
Listing courtesy of Compass Greater NY LLC
For Sale
$985,000
427 Sound Road
Greenport West NY 11944
2
1
2
Single-Family
Listing courtesy of Compass Greater NY LLC

Browse properties sold in nearby areas

The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed. Copyright © 2026 OneKey MLS. All Rights Reserved

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the "DMCA") provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under MLS GRID IDX Rules Updated September 16, 2024 7 U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to: dmca@ratemyagent.com

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner's behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

© 2026 RateMyAgent