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

Rental Listings

Shelter Island Nantucket Style Farmhouse with Dock and Sunsets

Shelter Island Nantucket Style Farmhouse with Dock and Sunsets

Priced at Custom (07/01/25 - 07/24/25) $45,000    Beds: 4    Baths: 3.5    Sq. Feet: 2799

Rental Registration #2025-L-0013. This picturesque Nantucket style farmhouse is tucked away in  ... Property Details

Shelter Island Cape Code with Deeded Waterfront Access

Shelter Island Cape Code with Deeded Waterfront Access

Priced at July ('25 - 25) $20,000; August(LD) ('25 - 25) $25,000    Beds: 5    Baths: 4    Sq. Feet: 3128

Rental Registration #2024-L-0099. This Shelter Island Cape Cod, located in Menantic Peninsula on a  ... Property Details

Glorious Shelter Island Waterfront Cottage

Glorious Shelter Island Waterfront Cottage

Priced at Two Weeks (08/16/25 - 09/01/25) $22,000    Beds: 4    Baths: 2    Sq. Feet: 1755

Rental Registration #2025-L-0011. This beachfront four bedroom with 3 Queen sized beds and one full  ... Property Details

Shelter Island Sunny Wades Beach Contemporary

Shelter Island Sunny Wades Beach Contemporary

Priced at Custom (07/01/25 - 07/30/25) $20,000; Two Weeks (07/01/25 - 07/15/25) $13,000; Two Weeks (07/17/25 - 07/31/25) $12,500; Custom (09/03/25 - 09/30/25) $3,000; Custom (10/03/25 - 10/31/25) $2,700; Custom (11/02/25 - 11/30/25) $2,700    Beds: 3    Baths: 2.5    Sq. Feet: 2428

Rental Registration #2024-L-0076. Located a stone's throw from popular southerly beach in quiet  ... Property Details

Shelter Island Elegant Bayfront with Deepwater Dock
Rented

Shelter Island Elegant Bayfront with Deepwater Dock

Priced at July/August(LD) ('25 - 25) $100,000 RENTED    Beds: 5    Baths: 4.5    Sq. Feet: 4467

Rental Registration #2024-L-0046. First offering! This elegant traditional graces a slight bluff  ... Property Details

Shelter Island Traditional with Pool, Beach and Lighthouse Views

Shelter Island Traditional with Pool, Beach and Lighthouse Views

Priced at July ('25 - 25) $69,000; August(LD) ('25 - 25) $80,000    Beds: 4    Baths: 4.5    Sq. Feet: 5122

Rental Registration #2024-L-0049. This traditional, with inspiring views of "Bug Light" lighthouse  ... Property Details

Shelter Island Newly Renovated Water View Cottage with Pool

Shelter Island Newly Renovated Water View Cottage with Pool

Priced at MD-LD ('25 - 25) $95,000; July/August(LD) ('25 - 25) $80,000; July ('25 - 25) $40,000; Custom (7/15/25 - 09/01/25) $65,000; Two Weeks (08/01/25 - 08/15/25) $20,000; August(LD) ('25 - 25) $45,000; September ('25 - 25) $20,000; October ('25 - 25) $12,500; November ('25 - 25) $5,000; December ('25 - 25) $5,000; January ('26 - 26) $5,000; February ('26 - 26) $5,000; March ('26 - 26) $5,000    Beds: 3    Baths: 3.5    Sq. Feet: 1836

Rental Registration #2024-L-0028. Located on a private Ram Island lane, this stylish and uplifting  ... Property Details

Shelter Island Heights Renovated Apartment

Shelter Island Heights Renovated Apartment

Priced at Year Round (12/01/24 - 11/30/25) $42,000    Beds: 2    Baths: 1   

Located in the heart of Shelter Island Heights in a mixed use building, this newly renovated 2  ... Property Details

Shelter Island Picturesque Farmhouse with Pool
Rented

Shelter Island Picturesque Farmhouse with Pool

Priced at July ('25 - 25) $25,000 RENTED    Beds: 8    Baths: 3    Sq. Feet: 2720

Rental Registration #2025-L-0014. Located a short distance from Heights, ferry, shops, fine dining  ... Property Details

Shelter Island Beach Cottage

Shelter Island Beach Cottage

Priced at MD-LD ('25 - 25) $32,000; July ('25 - 25) $11,000; August ('25 - 25) $12,000    Beds: 3    Baths: 2    Sq. Feet: 1428

Rental Registration #2025-L-0007. Shelter island's south side offers expansive Shell Beach and  ... Property Details

Shelter Island Estate Home Bordering Golf Course
Rented

Shelter Island Estate Home Bordering Golf Course

Priced at July ('25 - 25) $45,000 RENTED; August(LD) ('25 - 25) $50,000 RENTED    Beds: 4    Baths: 5.5    Sq. Feet: 4000

Rental Registation #2025-L-0004. This new estate home on a shy acre bordering Gardiners Bay Country  ... Property Details

Shelter Island Traditional with Pool bordering Preserve

Shelter Island Traditional with Pool bordering Preserve

Priced at Weekly (08/15/25 - 09/01/25) $19,500; Weekly (09/01/25 - 09/30/25) $12,900; Weekly (10/01/25 - 10/31/25) $6,900; Weekly (11/01/25 - 11/30/25) $5,500; Weekly (12/01/25 - 12/31/25) $5,000    Beds: 5    Baths: 5.5    Sq. Feet: 4700

Rental Registration #2024-V-0024. This grand compound bordering parkland is spectacular. The main  ... Property Details

Shelter Island Close Proximity to Beach

Shelter Island Close Proximity to Beach

Priced at Two Weeks (07/01/25 - 07/31/25) $11,000; Weekly (07/01/25 - 07/31/25) $5,500; Two Weeks (08/01/25 - 09/02/25) $11,000; Weekly (08/01/25 - 08/31/25) $5,500    Beds: 3    Baths: 2    Sq. Feet: 1384

Rental Registration #2025-V-011. Welcome to a charming and immaculate cottage that is sure to  ... Property Details

Shelter Island Modern with Pool

Shelter Island Modern with Pool

Priced at Custom (07/01/25 - 07/13/25) $25,000; August(LD) ('25 - 25) $45,000 RENTED    Beds: 3    Baths: 3    Sq. Feet: 2891

Rental Registration #2023-L-0161. This sleek and sun-filled modern on approximately one acre borders  ... Property Details

Shelter Island Wades Beach with Pool

Shelter Island Wades Beach with Pool

Priced at July ('25 - 25) $32,000; August(LD) ('25 - 25) $35,000    Beds: 4    Baths: 3    Sq. Feet: 2842

Rental Registration #2023-L-0163. This arts and crafts cottage sits on 1.0+/- acre overlooking a  ... Property Details

Shelter Island Charming Harbor Front Cottage

Shelter Island Charming Harbor Front Cottage

Priced at July ('25 - 25) $25,000; August(LD) ('25 - 25) $25,000    Beds: 3    Baths: 3    Sq. Feet: 2209

Rental Registration #2023-L-0164. Turn of the century cottage with southern views onto the harbor  ... Property Details

Charming Shelter Island Heights Harborview Victorian

Charming Shelter Island Heights Harborview Victorian

Priced at Two Weeks (07/01/25 - 07/21/25) $10,000    Beds: 4    Baths: 2.5    Sq. Feet: 2140

Rental Registration #2024-L-0110. This 1885 Shelter Island Heights Victorian, located in the heart  ... Property Details

Shelter Island Scandinavian with Pool and Guest House

Shelter Island Scandinavian with Pool and Guest House

Priced at July ('25 -25) $32,000; Two Weeks (08/01/25 - 08/15/25) $15,000 RENTED    Beds: 5    Baths: 4    Sq. Feet: 3600

Rental Registration #2024-L-0043. Located within close proximity to popular Sunset Beach, golf,  ... Property Details

Chic Shelter Island Barn with Pool and Day Dock

Chic Shelter Island Barn with Pool and Day Dock

Priced at Custom (08/25/25 - 09/05/25) $11,000    Beds: 3    Baths: 2    Sq. Feet: 1560

Rental Registration #2025-L-0006. This chic barn-style house is located off a quiet lane and is  ... Property Details

Sun-Filled Shelter Island Charming Cottage Close to Beach
Rented

Sun-Filled Shelter Island Charming Cottage Close to Beach

Priced at August(LD) ('25 - 25) $14,000 RENTED    Beds: 4    Baths: 3    Sq. Feet: 2400

Rental Registration #2024-L-0026. This sun filled one level cottage is located within a stone's  ... 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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