Snapshot of real estate on Shelter Island

It’s a buyer’s market; it’s a seller’s market. Can it be both? Many Island real estate professionals tend to confirm that, since sellers and buyers are increasingly savvy about what properties are worth and the national economy enters into the picture.

A consensus agrees that with some downward movement on interest rates, reluctant buyers are beginning to pull the trigger on deals that were slow to close.

According to Realtor.com,“The median listing home price in Shelter Island was $2.8M in September 2025, trending up 22.1% year-over-year. The median listing home price per square foot was $1,000 … On average, homes in Shelter Island sell after 137 days on the market. The trend for median days on market has gone up since last month, and slightly up since last year.”

What doesn’t sell today are properties whose owners aren’t pricing them properly, said broker Melina Wein. Still, she added, it tends to take longer to move a deal forward because buyers want to watch the market for awhile to determine when the best time to close will show itself.

COVID brought deals to the table because many families wanted to leave congested city areas and regarded Shelter Island as safer. But what sold at escalated prices slowed once the pandemic eased. At first the market was slow, Ms. Wein said. But property owners recognized they had to negotiate if they were going to close, she said.

Angelo Piccozzi of Dering Harbor Real Estate said business is thriving, but it takes more deals at lower prices to keep momentum. There are fewer closings at $4 to $5 million today, with many more fetching prices of $1.5 to $2.5 million, several real estate professionals reported.

Another factor is properties transferred from one generation to another in families often took several decades before they were available, are selling these days, Mr. Piccozzi said. As families gravitate to other parts of the country, and the oldest generation wants to be nearer to children and grandchildren, people are moving off the Island and some younger families are buying those houses.

It’s encouraging that it’s only early November, but Mr. Piccozzi is already seeing people looking for summer rentals for 2026. Many who start as renters on Shelter Island become buyers after a summer or two, he said.

Independent broker Susan Cincotta confirmed the price point for sales, saying she’s seeing deals close at $2.5 million or less. Sellers and buyers are realistic about prices and more houses are coming to the market than has been true in any recent times, she said.

It’s a different market, said Marika Kaasik, who said she remembers other times when deals were taking lengthy periods of time to close. Still, today deals are moving. “COVID was an anomaly,” Ms. Kaasik said. If it’s not the place where the real estate market offers many deals on multi-million properties, there are still some along Gardiner’s Bay that are selling at high prices, she added.

With the inauguration of Donald Trump in January 2025 sales dropped off in the real estate market, said Saunders Real Estate Broker Penelope Moore. She was running around a lot, showing a lot of good properties, but not seeing many closings. Something changed in August though, and sales began to close, Ms. Moore said. 

Potential buyers she had known for years who said they weren’t ready to purchase are becoming serious buyers. Why? Cynthia Barrett of Brown Harris Stevens thinks she knows.

Rumors of interest rates dropping began percolating and while they might not yet be at desirable levels, potential buyers who had hesitated, were returning and taking serious looks at properties, Ms. Barrett said.

Sellers who had been holding firm to higher prices and even leaving the market for awhile, suddenly saw a market with a lot of inventory and realized they could sell but would have to reduce their asking prices to be competitive. They had to absorb multiple price reductions, Ms. Barrett said.

Buyers at the high end were often in financial services, had a good year and were expecting 2026 would be the same. They had money to spend and could look at even some of the high end properties.

While it doesn’t mean there weren’t slow times — open houses when no one showed to look at the properties — gradually serious buyers were coming out to look at properties and over time, sales picked up. Many of the buyers are younger and will own houses that could stay in their families for generations, Ms. Barrett said.

Janalyn Travis-Messer of Griffing & Collins a DTM Enterprises, which builds houses on Shelter Island, East Hampton and in Pennsylvania, speculated that more sellers are lowering property prices, a factor that she said is “a good thing.” For her, it’s a buyer’s market and although interest rates have dropped only a little, there’s still a reluctance by buyers to consider a “fixer upper” even if work is relatively modest. Buyers are hesitant to take on a property that needs work, wanting assurance what they purchase is a negotiated price they can manage with no unknowns.

They may be missing a good deal since generally agents have knowledge of which trades people to recommend, and there are many reasonably priced and highly capable workers on the Island who can create the perfect house for their needs with a minimum of work, she said.

Trust those recommendations from your broker who wants you to be happy about your purchase, which can result in referrals, Ms. Travis-Messer said.

Douglas Elliman Executive Manager of Sales Tim Kelly, who works out of the company’s Sag Harbor office, said what everyone says: If properties are priced right, even those at the high end will draw buyers.