Penelope Moore
Licensed Associate Real Estate Broker
(631) 749-5801
  • Email
  • Facebook
  • Instagram
  • Twitter
  • Home
  • Search
    • Residential Listings
    • Land Listings
    • Rental Listings
    • Sold Listings
    • Shelter Island Sold Properties
  • Neighborhoods
  • Buyers
  • Sellers
  • Blog
  • About
    • About
    • Shelter Island Town Information
    • Testimonials
    • Penelope in the News
    • Standard Operating Procedures
    • Support
  • Contact
Home > Rentals > Page 2

Rental Listings

Cozy 2 Bedroom Cottage

Cozy 2 Bedroom Cottage

Priced at Winter (01/01/23 - 03/31/23) $12,000; Custom (04/01/23 - 04/21/23) $6,750; August ('23 - 23) $35,000    Beds: 2    Baths: 1    Sq. Feet: 1248

Rental Registration #2022-L-0011. This sun-filled cedar shingled cottage on a quiet lane, and within  ... Property Details

5 Bedroom Colonial with Infinity Pool and Waterfront Beach

5 Bedroom Colonial with Infinity Pool and Waterfront Beach

Priced at February ('23 - 23) $10,000; March ('23 - 23) $10,000; April ('23 - 23) $12,000; May ('23 - 23) $18,000; Custom (06/15/23 - 06/22/23) $6,000; Custom (08/18/23 - 09/04/23) $32,000; September ('23 - 23) $20,000; Custom (09/18/23 - 09/30/23) $12,000; October ('23 - 23) $18,000; November ('23 - 23) $15,000; December ('23 - 23) $15,000    Beds: 5    Baths: 6.5    Sq. Feet: 5670

Rental Registration #2021-L-88. This charming 5 bedroom, 6 bath colonial has an open floor plan that  ... Property Details

Shelter Island Hidden Gem with Pool

Shelter Island Hidden Gem with Pool

Priced at August(LD) ('23 - 23, w/o LD $27k) $30,000    Beds: 4    Baths: 3    Sq. Feet: 1542

Rental Registration #2022-L-0013. This modern 4 Bedroom, 3 bathroom hidden gem with pool features an  ... Property Details

Shelter Island Quiet Contemporary with Pool

Shelter Island Quiet Contemporary with Pool

Priced at Weekly (06/01/23 - 06/30/23) $7,000; Weekly (07/01/23 - 07/31/23) $8,750; Weekly (08/23/23 - 08/31/23) $10,000; Custom (08/23/23 - 09/04/23) $15,000    Beds: 4    Baths: 3    Sq. Feet: 1900

Rental Registration #2021-L-72. Located within close proximity to Wades Beach on Shelter Island,  ... Property Details

Shelter Island Harborfront Farmhouse

Shelter Island Harborfront Farmhouse

Priced at June ('23 - 23) $15,000; July ('23 - 23) $30,000 RENTED; August(LD) ('23 - 23) $35,000 RENTED; Weekly (09/05/23 - 09/30/23) $5,500; September (09/05/23 - 09/30/23) $16,500    Beds: 3    Baths: 1 Full, 1 Half    Sq. Feet: 1536

Rental Registration #2121-L-54. This classic Shelter Island harborfront farmhouse was built in 1900  ... Property Details

Shelter Island Heights Charming Waterview Farmhouse

Shelter Island Heights Charming Waterview Farmhouse

Priced at June ('23 - 23) $15,000; July ('23 - 23) $28,000; August(LD) ('23 - 23) $32,000    Beds: 4    Baths: 2    Sq. Feet: 2007

Rental Registration #2021-L-55. New to the rental market! This Shelter Island Heights farmhouse,  ... Property Details

Shelter Island Serenity with Farm Views and Saltwater Pool

Shelter Island Serenity with Farm Views and Saltwater Pool

Priced at July ('23 - 23) $29,000    Beds: 3    Baths: 2    Sq. Feet: 1639

Rental Registration #2021-L-22. Bordering Westmoreland Farm, this spacious traditional with privet  ... Property Details

Sunny Shelter Island Cape Cod

Sunny Shelter Island Cape Cod

Priced at June ('23 - 23) $12,000; August(LD) ('23 - 23) $22,000    Beds: 5    Baths: 2    Sq. Feet: 1779

Rental Registration #2021-L-43. This pristine five bedroom Cape Cod was recently renovated and is  ... Property Details

Modernist Waterfront with Pool near Shelter Island Heights

Modernist Waterfront with Pool near Shelter Island Heights

Priced at July ('23 - 23) $50,000    Beds: 3    Baths: 3.5    Sq. Feet: 1536

Rental Registration #2021-L-28. Tucked away on a gravel road, just outside Shelter Island Heights,  ... Property Details

Shelter Island Mid Century Modern with Pool

Shelter Island Mid Century Modern with Pool

Priced at September ('23 - 23) $16,000; Winter (09/01/23 - 05/31/24) $4,200; October ('23 - 23) $16,000    Beds: 3    Baths: 2.5    Sq. Feet: 1634

Rental Registration# 21-1-64.This sleek mid century modern on shy acre is located a few doors from a  ... Property Details

Shelter Island Cottage with Pool Close to Beach

Shelter Island Cottage with Pool Close to Beach

Priced at June ('23 - 23) $15,000; July ('23 - 23) $30,000; August(LD) ('23 - 23, w/o LD $33k) $37,000    Beds: 3    Baths: 2    Sq. Feet: 1456

Rental Registration# 2021-L-41. Located within close proximity to sandy beach with sunsets galore  ... Property Details

Bayview Contemporary Shelter Island

Bayview Contemporary Shelter Island

Priced at Weekly (09/06/22 - 06/04/23) $5,000; Custom (06/13/23 - 06/23/23) $9,000; July ('23 - 23) $20,900; Two Weeks (07/01/23 - 07/14/23) $11,000; August(LD) ('23 - 23) $24,000; Two Weeks (08/01/23 - 09/04/23) $13,000    Beds: 4    Baths: 3    Sq. Feet: 2600

Rental Registration #2022-V-0017. This sunny Contemporary with slices of water views has loads of  ... Property Details

Iconic Shelter Island Heights Waterview Victorian

Iconic Shelter Island Heights Waterview Victorian

Priced at Custom (05/26/23 - 06/30/23) $26,000; June ('23 - 23) $23,000; July ('23 - 23) $31,000; August(LD) ('23 - 23, w/o LD $34k) $36,000; Custom (09/04/23 - 09/30/23) $26,000    Beds: 5    Baths: 3.5    Sq. Feet: 2596

Rental Registration #2022-S-0002. Since the turn of the century, this Victorian has greeted visitors  ... Property Details

Charming and Simple Harborfront with Dock

Charming and Simple Harborfront with Dock

Priced at May ('23 - 23) $10,000; Custom (06/01/23 - 06/15/23) $10,000; Custom (07/15/23 - 08/15/23) $35,000; Custom (09/18/23 - 09/30/23) $10,000; October ('23 - 23) $20,000    Beds: 4    Baths: 2    Sq. Feet: 2170

Rental Registration #2023-L-0009. This straightforward L-shaped cottage on the harbor has a  ... Property Details

Iconic Shelter Island Heights Waterview Victorian

Iconic Shelter Island Heights Waterview Victorian

Priced at June ('23 - 23) $32,000; July ('23 - 23) $38,000; August(LD) ('23 - 23, w/o LD $40k) $42,000    Beds: 5    Baths: 3 Full, 2 Half    Sq. Feet: 2740

Rental Registration #20-L-0095. This completely restored 1890's Shelter Island Victorian is in the  ... Property Details

Shelter Island Cottage with Beach, Dock & Mooring

Shelter Island Cottage with Beach, Dock & Mooring

Priced at June/July (05/26/23 - 07/31/23) $70,000; July ('23 - 23) $40,000    Beds: 4    Baths: 4    Sq. Feet: 2180

Rental Registration# 2022-L-0112. Located on the harbor, this cheery country cottage has wonderful  ... Property Details

Shelter Island Spacious Traditional with Pool Close to Beach

Shelter Island Spacious Traditional with Pool Close to Beach

Priced at Custom (07/15/23 - 07/31/23) $22,000; August(LD) ('23 - 23, w/o LD $50k ) $62,500; Two Weeks (09/05/23 - 09/30/23) $18,000    Beds: 5    Baths: 3.5    Sq. Feet: 2552

Rental Registration #2022-L-0048. Enjoy your summer at this spacious traditional with plenty of room  ... Property Details

Newly renovated 1911 Plantation Style Home

Newly renovated 1911 Plantation Style Home

Priced at May ('23 - 23) $30,000; June ('23 - 23) $35,000; July ('23 - 23) $50,000; August(LD) ('23 - 23) $65,000    Beds: 6    Baths: 4.5    Sq. Feet: 2790

Rental Registration #2023-L-0005. This newly renovated 1911 plantation style home combines old world  ... Property Details

Glorious Shelter Island Waterview with Pool

Glorious Shelter Island Waterview with Pool

Priced at Winter (10/01/22 - 04/30/23) $10,000; Custom (05/01/23 - 05/25/23) $25,000; MD-LD ('23 - 23) $150,000; June ('23 - 23) $35,000; July ('23 - 23) $50,000; August(LD) ('23 - 23) $60,000; Custom (09/05/23 - 09/30/23) $25,000    Beds: 4    Baths: 3    Sq. Feet: 2337

Rental Registration #19L-0077 This elevated contemporary sited on one acre overlooking the waters  ... Property Details

Shelter Island Spacious Traditional with Pool

Shelter Island Spacious Traditional with Pool

Priced at Feb ('23 - 23) $15,000; March ('23 - 23) $15,000; April ('23 - 23) $15,000; May ('23 - 23) $15,000; June ('23 - 23) $45,000; July ('23 - 23) $55,000; August ('23 - 23) $65,000; October ('23 - 23) $15,000; November ('23 - 23) $15,000; December ('23 - 23) $15,000    Beds: 5    Baths: 5.5    Sq. Feet: 3868

Rental Registration #2023-L-0003. With views to a 12 +/- acre preserve directly across the street  ... Property Details

  • « Previous Page
  • 1
  • 2
  • 3
  • 4
  • 5
  • Next Page »

Contact Me

Lets Chat! Contact me with any questions!
Contact

Stay Connected

  • Email
  • Facebook
  • Instagram
  • Twitter
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

CRS logo
Saunders Realty logo

© 2023 All Rights Reserved  •  Privacy Policy  •  Accessibility Statement