Penelope Moore
Licensed Associate Real Estate Broker
(631) 749-5801
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Home > Rentals > Page 3

Rental Listings

Shelter Island Spacious Traditional near Beach

Shelter Island Spacious Traditional near Beach

Priced at August(LD) ('25 - 25) $39,000    Beds: 4    Baths: 2.5    Sq. Feet: 2682

Spacious Shelter Island Rental Rental Registration #2024-L-0111. Located a stone's throw from wide  ... Property Details

Shelter Island Water View with Pool

Shelter Island Water View with Pool

Priced at Two Weeks (07/01/25 - 07/31/25) $12,000; July ('25 - 25) $23,000    Beds: 4    Baths: 2    Sq. Feet: 1932

Rental Registration #2025-L-0048. Located a stone's throw from sandy beach just across the street,  ... Property Details

Shelter Island Quiet Contemporary with Pool

Shelter Island Quiet Contemporary with Pool

Priced at July/August(LD) ('25 - 25) $42,000, July ('25 - 25) $20,000; August(LD) ('25 - 25) $22,000    Beds: 3    Baths: 2    Sq. Feet: 2500

Rental Registration #2025-L-0008. Located in the Conservancy Estates area on the south side of  ... Property Details

Shelter Island Pristine Traditional with Pool

Shelter Island Pristine Traditional with Pool

Priced at July (07/01/25 - 07/18/25) $20,000; August(LD) ('25 - 25) $37,000    Beds: 4    Baths: 3    Sq. Feet: 3194

Rental Registration #2024-L-0027. This recently built traditional is located on one acre within  ... Property Details

Fabulous Shelter Island Modern with Pool

Fabulous Shelter Island Modern with Pool

Priced at Two Weeks (06/01/25 - 06/30/25) $8,500; Two Weeks (07/01/25 - 07/31/25) $14,500; Two Weeks (08/01/25 - 09/01/25) $14,500; Two Weeks (09/02/25 - 09/30/25) $8,000    Beds: 3    Baths: 3    Sq. Feet: 1338

Rental Registration #2024-L-0093. Located within close proximity to marina, this sleek modernist,  ... Property Details

Turn Of The Century Shelter Island Waterfront

Turn Of The Century Shelter Island Waterfront

Priced at June ('25 - 25) $17,000; July/August(LD) ('25 - 25) $52,500 RENTED; Custom (09/06/25 - 09/30/25) $20,000    Beds: 4    Baths: 2    Sq. Feet: 2500

Rental Regisstration #2023-L-0177. Located on the harbor, this classic turn of the century Farmhouse  ... Property Details

Shelter Island Ram Island Beachfront with Pool

Shelter Island Ram Island Beachfront with Pool

Priced at June ('25 - 25) $26,500; Custom (07/01/25 - 07/10/25) $15,000; September ('25 - 25) $26,500    Beds: 4    Baths: 2    Sq. Feet: 1500

Rental Registration #2023-L-0001. Set on 1.8 +/- waterfront acres on Ram Island by Coecles Harbor  ... Property Details

Clean East Hampton Contemporary with Pool and Tennis

Clean East Hampton Contemporary with Pool and Tennis

Priced at July ('25 - 25) $27,000; August(LD) ('25 - 25) $29,000 RENTED    Beds: 4    Baths: 2    Sq. Feet: 1850

Rental Registration #23-1112. No groups or shares. Located approximately 1.5 +/- miles from town on  ... Property Details

Sunny Shelter Island Waterfront with Dock and Sandy Beach

Sunny Shelter Island Waterfront with Dock and Sandy Beach

Priced at August ('25 - 25) $49,500; September ('25 - 25) $25,000    Beds: 4    Baths: 3    Sq. Feet: 2799

Rental Registration #2023-V-0037. Set close to wide sandy beach on slight bluff, this sunny  ... Property Details

Shelter Island Close Proximity to Beach with Pool

Shelter Island Close Proximity to Beach with Pool

Priced at July ('25 - 25) $11,500; August(LD) ('25 - 25) $16,500    Beds: 3    Baths: 2    Sq. Feet: 1600

Rental Registration #2024-L-0085. A sweet ranch house on 1.5 +/- acres within close proximity to  ... Property Details

Shelter Island Dering Harbor Front Delight

Shelter Island Dering Harbor Front Delight

Priced at MD-LD ('25 -25) $130,000; June ('25 - 25) $50,000; July ('25 - 25) $55,000; August ('25 - 25) $60,000    Beds: 4    Baths: 4    Sq. Feet: 3606

Rental Registration #2023-L-0146. This four-bedroom, four-bath traditional sits directly on Dering  ... Property Details

Sunny Bayfront on Shelter Island
Rented

Sunny Bayfront on Shelter Island

Priced at August(LD) ('25 - 25) $20,000 RENTED    Beds: 4    Baths: 2.5    Sq. Feet: 1504

Rental Registration #2023-L-0041. This contemporary offers four bedrooms and two and one half baths  ... Property Details

Traditional Pond Front Shelter Island

Traditional Pond Front Shelter Island

Priced at MD-LD ('25 - 25) $50,000; June ('25 - 25) $15,000; July ('25 - 25) $20,000; August(LD) ('25 - 25) $25,000    Beds: 4    Baths: 2.5    Sq. Feet: 3000

Rental Registration #2024-L-0024. This Victorian Traditional has four bedrooms, two and one half  ... Property Details

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Penelope Moore

Penelope Moore

Since 1998, Penelope has been the driving force and leader in the Shelter Island real estate market, and is the go-to real estate broker for discerning buyers and sellers. She has experienced record-breaking sales in multiple categories over successive years, and her success has been distinguished not just by benchmark sales, but by volume in all categories.

Meet Penelope

Penelope Moore, Licensed Associate Real Estate Broker

9 Grand Avenue, PO Box 100
Shelter Island Heights, NY 11965-0100

(631) 749-5801
(917) 208-5519 Mobile

Contact Penelope

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