24 Harbor Lane - .53 acre, 3736 sq ft, 4 bedroom, 4.5 bath, harbor view Colonial, last listed at $6,995,000 on 3/15/25 and sold for $6,700,000 on 6/4/25;  23A Harbor Lane - .27 acre, 2758 sq ft, 2 bedroom, 3.5 bath Colonial, last listed at $5,250,000 and sold for $5,250,000 on 4/4/25; 104 South Ferry Road - 3.44 acre, 4040 sq ft, 5 bedroom,  5 full bath, 2 half bath Traditional Continue Reading

As of the week following Memorial Day 2025, the Shelter Island rental market remains flat. Traditionally, the bulk of summer rental activity occurs between Columbus Day and mid-April, with prospective tenants searching and securing leases during that time. This past off-season, however, most inquiries have been for short-term stays or dates that don’t align with typical monthly start and end Continue Reading

Memorial Day, observed on the last Monday of May, is a national day of remembrance for those who died while serving in the U.S. military. While it marks the unofficial beginning of summer for many Americans, the day’s true purpose is solemn: to honor lives lost in service to the country. Originally known as Decoration Day, the tradition began in the years following the Civil War, a conflict that Continue Reading

Each spring, the Town of Shelter Island conducts re-assessments of properties throughout the island. This involves comparing the subject property to similar properties, ideally in the same general vicinity as the subject. Unlike an appraisal, which contemplates transfers from the immediate 12 months prior, an assessment is a lagging indicator going back over a period of three years from the prior Continue Reading

Gratitude and Momentum in a Busy Holiday Season As Thanksgiving approaches, the area’s farm stands and markets are bustling with shoppers preparing for cherished gatherings around the table, sharing a festive feast with family and friends. In the midst of the holiday excitement, the autumn-to-winter real estate market usually serves as a quieter, yet vital backdrop. This season often Continue Reading

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https://www.youtube.com/watch?v=h_YO8RXkw9k&authuser=0 https://youtube.com/shorts/99NX7GRV9hI?feature=shared Memorial Day on Shelter Island Honoring the Fallen Heroes Memorial Day, an American holiday observed on the last Monday of May, honors the men and women who died while serving in the U.S. military. Originally known as Decoration Day, it originated in the years following the Continue Reading

Following Labor Day weekend and Hurricane Ophelia's persistent rains, Shelter Island displays clear autumnal signs. Trees a little farther west on Long Island showcase tips of leaves turning to vibrant shades of red and orange as a sort of "coming soon attraction" while local farm stands now have a variety of pumpkins, colorful mums, autumn apples, and harvest-time vegetables on display. The Continue Reading

As summer 2023 draws to a close, Shelter Island has seen its community rekindle cherished activities and friendships post-pandemic, with many marveling at how swiftly the season has passed. Events such as the 10K Race, Fireworks, Vintage Car Show, The Green Expo, and Chicken Barbecue have marked the season. And as we anticipate the Snapper Derby this weekend, we’re reminded that Tumbleweed Tuesday Continue Reading