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

Rental Listings

Shelter Island Sweet Traditional with Pool

Shelter Island Sweet Traditional with Pool

Priced at December ('23 - 23) $8,500; January ('24 - 24) $6,000; February ('24 - 24) $6,000; March ('24 - 24) $6,500; April ('24 - 24) $6,500; Custom (06/11/24 - 06/26/24) $16,000; Custom (07/13/24 - 08/02/24) $27,000; Custom (08/03/24 - 09/02/24) $40,000    Beds: 4    Baths: 3.5    Sq. Feet: 2004

Rental Registration #2022-L-0004. This traditional with four-bedrooms, three and one-half bathrooms  ... Property Details

Shelter Island Waterfront with Pool

Shelter Island Waterfront with Pool

Priced at July ('24 - 24) $35,000; August(LD) ('24 - 24) $37,000    Beds: 3    Baths: 4    Sq. Feet: 3160

Rental Registration #0012. Some of the most spectacular sunsets can be enjoyed from this spacious  ... Property Details

Charming 1920’s Waterfront Cottage with Dock

Charming 1920’s Waterfront Cottage with Dock

Priced at July ('24 - 24) $14,900 RENTED; Two Weeks (07/01/24 - 07/31/24) $7,600 RENTED; August (08/02/24 - 09/03/24) $14,750    Beds: 1    Baths: 2    Sq. Feet: 875

Rental Registration #23-V-0016. Located within short distance to the ferry, Heights and beach, this  ... Property Details

Pristine Shelter Island Bay View with Dock Access

Pristine Shelter Island Bay View with Dock Access

Priced at July ('24 - 24) $28,000; August(LD) ('24 - 24, w/o LD $30k) $35,000; September ('24 - 24) $20,000    Beds: 3    Baths: 2    Sq. Feet: 1608

Rental Registration #2021-L-91. This recently renovated ranch has a sunny living room, kitchen with  ... Property Details

Lush and Lovely Shelter Island with Pool

Lush and Lovely Shelter Island with Pool

Priced at July ('24 - 24) $38,000    Beds: 4    Baths: 4    Sq. Feet: 2424

Rental Registration #2022-L-0084. Located a half block from sandy beach, this deer free property has  ... Property Details

Shelter Island Cottage Close Proximity to Sandy Beach

Shelter Island Cottage Close Proximity to Sandy Beach

Priced at December ('23 - 23) $2,200; January ('24 - 24) $2,200; February ('24 - 24) $2,200; March ('24 - 24) $2,200; April ('24 - 24) $2,200; June ('24 - 24) $7,000; July ('24 - 24) $11,500; August(LD) ('24 - 24) $14,500 RENTED    Beds: 3    Baths: 1.5    Sq. Feet: 1935

Rental Registration #2022-L-0061. New to the rental market! This well maintained, sunny cottage is  ... Property Details

Shelter Island Heights Contemporary

Shelter Island Heights Contemporary

Priced at Year Round (09/11/23 - 09/11/24) $4,000    Beds: 3    Baths: 2    Sq. Feet: 1584

Rental Registration #2023-L-0011. Located a stone's throw from Shelter Island Country Club, Crescent  ... Property Details

Summer Beach Cottage on Shelter Island

Summer Beach Cottage on Shelter Island

Priced at MD-LD ('24 - 24) $28,000; June ('24 - 24) $8,000; July ('24 - 24) $15,000; Two Weeks (08/01/24 - 08/31/24) $10,000; August(LD) ('24 - 24) $18,000; Year Round (09/01/24 - 09/30/25) $36,000    Beds: 2    Baths: 1    Sq. Feet: 700

Shelter Island Summer Beach Cottage for Rent Rental Registration #2023-L-0105. Located within close  ... Property Details

Shelter Island Water View with Pool

Shelter Island Water View with Pool

Priced at December ('23 - 23) $5,000; March ('24 - 24) $5,000; May ('24 - 24) $5,000; June ('24 - 24) $14,000; July ('24 - 24) $23,000; August(LD) ('24 - 24, w/o LD $23k) $25,000; September ('24 - 24) $14,000; Custom (09/06/24 - 09/30/24) $10,000    Beds: 4    Baths: 2    Sq. Feet: 1932

Rental Registration #2023-L-0006. Located a stone's throw from sandy beach just across the street,  ... Property Details

Fabulous Shelter Island Sandy Beach House with Pool

Fabulous Shelter Island Sandy Beach House with Pool

Priced at Custom (07/08/24 - 08/02/24) $21,625; Two Weeks (08/19/24 - 08/30/24) $10,899; Custom (09/09/24 - 09/30/24) $16,349; Two Weeks (10/01/24 - 10/14/24) $10,899    Beds: 5    Baths: 5    Sq. Feet: 2954

Rental Registratino #2022-L-0114. Located in the estate section, this sprawling five bedroom ranch  ... Property Details

Shelter Island Quiet Contemporary with Pool

Shelter Island Quiet Contemporary with Pool

Priced at June ('24 - 24) $15,000; July ('24 - 24) $28,000; August(LD) (08/01/24 - 09/02/24) $32,000    Beds: 3    Baths: 2    Sq. Feet: 2500

Rental Registration #2023-L-0127. Located in the Conservancy Estates area on the south side of  ... Property Details

Fabulous Shelter Island Waterview with Pool

Fabulous Shelter Island Waterview with Pool

Priced at Year Round (11/15/23 - 11/15/24) $120,000; MD-LD ('24 - 24) $95,000; June ('24- 24) $25,000; July ('24- 24) $30,000    Beds: 3    Baths: 2.5    Sq. Feet: 1832

Rental Registration #2023-L-0110. Located just a stone's throw from wide sandy beaches, this  ... Property Details

Southernly Shelter Island Waterfront

Southernly Shelter Island Waterfront

Priced at Year Round (10/1/23 - 09/30/24) $120,000    Beds: 4    Baths: 2    Sq. Feet: 2100

Rental Registration #20-L-0048. Pristine and sunny contemporary with lush southernly views, open  ... Property Details

Fabulous Shelter Island Modern with Pool

Fabulous Shelter Island Modern with Pool

Priced at MD-LD ('24 - 24) $70,000; June ('24 - 24) $16,500; Two Weeks (06/01/24 - 06/30/24) $8,500; July ('24 - 24) $27,000; July/August(LD) ('24 - 24) $56,000; Two Weeks (07/01/24 - 07/31/24) $14,500; August(LD) ('24 - 24, w/o LD $27k) $37,000; Two Weeks (08/01/24 - 08/31/24) $14,500; September ('24 - 24) $15,000; Two Weeks (09/01/24 - 09/30/24) $8,000    Beds: 3    Baths: 3    Sq. Feet: 1338

Rental Registration #2022-L-0052. 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 (05/24/24 - 06/30/24) $18,000; June ('24 - 24) $17,000; July/August(LD) ('24 - 24) $59,000 RENTED; July ('24 - 24) $27,000 RENTED; August(LD) ('24 - 24, w/o LD $30k) $32,000 RENTED; Custom (09/06/24 - 09/30/24) $20,000    Beds: 4    Baths: 2    Sq. Feet: 2500

Rental Registration #2022-L-0106. 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 ('24 - 24) $26,500; September ('24 - 24) $26,500    Beds: 4    Baths: 2    Sq. Feet: 1500

Rental Registration #2022-L-0005. 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 June (05/27/24 - 06/30/24) $25,000; July ('24 - 24) $27,000; August(LD) ('24 - 24) $29,000    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

Shelter Island Creekfront with Dock and Pool

Shelter Island Creekfront with Dock and Pool

Priced at June (05/24/24 - 06/30/24) $18,000; July ('24 - 24) $25,500 RENTED; August(LD) ('24 - 24) $30,600 RENTED; September (09/03/24 - 09/30/24) $21,000    Beds: 4    Baths: 3    Sq. Feet: 3000

Rental Registration #2023-L-0029. This four-bedroom, three-bath waterfront Traditional occupies .75  ... Property Details

Stunning Shelter Island Little Ram Waterfront with Pool

Stunning Shelter Island Little Ram Waterfront with Pool

Priced at June ('24 - 24) $25,000; July ('24 - 24) $30,000; August(LD) ('24 - 24) $35,000; September (09/03/24 - 09/30/24) $25,000    Beds: 4    Baths: 3    Sq. Feet: 1584

Rental Registration #2023-L-0090. Located on Little Ram Island on Gardiners Bay, this four bedroom,  ... Property Details

Splendid Shelter Island Estate with Pool

Splendid Shelter Island Estate with Pool

Priced at June ('24 - 24) $25,000; Weekly (06/01/24 - 06/30/24) $7,000; July ('24 - 24) $60,000; Weekly (07/01/24 - 07/31/24) $15,000; Custom (08/03/24 - 08/10/24) $18,000; Custom (08/11/24 - 08/18/24) $18,000    Beds: 4    Baths: 2.5    Sq. Feet: 3500

Rental Registration #2023-L-0025. This Shelter Island historic home was built in 1791, with  ... 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

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