“Working with Maria to purchase our first home was nothing short of amazing. Not only was she kind, friendly, and extremely knowledgeable, but she also made the home buying process FUN! When we finally found our dream home, she did all in her power to help us seal the deal - and she did! Even during closing when we hit a few speed bumps, she was right there making sure everything was smoothed over. I could not recommend her more! If you’re looking to buy a home, seriously, get in touch with Maria! She will make your entire experience amazing. Thank you so much Maria!”
- Agent Pronto
- New York
- Shelter Island
The best way to find top real estate agents in Shelter Island, NY
We analyze thousands of real estate agents in Shelter Island and nationwide to find you proven local professionals, for free.
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Compare top Shelter Island real estate agents.
Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for November 2026.*
*Sales data is calculated based on transaction information available to Agent Pronto at the time of publishing and may not accurately reflect all transactions for a given agent.
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- Tell us what you need.
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Shelter Island real estate Market Report.
Information and statistics on the latest trends in the Shelter Island real estate market. *
Latest Rolling 3-Month Snapshot
Jul 1, 2026 - Sep 30, 2026
Quarterly Pricing Trends for Shelter Island
Rolling three-month data ending on quarter boundaries when available.
Quarterly Pricing Trends for Shelter Island
Rolling three-month data ending on quarter boundaries when available.
Quarterly Pricing Trends for Shelter Island
Rolling three-month data ending on quarter boundaries when available.
Quarterly Inventory and Sales Activity for Shelter Island
Rolling three-month supply and activity totals for the selected period.
Quarterly Inventory and Sales Activity for Shelter Island
Rolling three-month supply and activity totals for the selected period.
Quarterly Inventory and Sales Activity for Shelter Island
Rolling three-month supply and activity totals for the selected period.
Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Jul 2026 - Sep 2026).
Inventory on Shelter Island has edged up in this rolling three-month view, with about 30 active listings and a modest 12 percent increase from a year ago. Contract activity is relatively light, as only 4 homes sold and 4 went pending, even though closed sales are up more than a third compared with last year.
Pricing is adjusting to this slower pace, with the typical home value down nearly 9 percent year over year and the median list price falling more than 20 percent over the same period. Sellers are also seeing buyers negotiate more, as the average sale-to-list ratio sits around 95 percent and no homes in this period closed above their asking price.
Time on market tells an interesting story, because the median days on market is roughly 184 days, which is still long but about half what it was a year ago. Even with that improvement, months of supply remains high at over 19 months, reinforcing Shelter Island’s status as a buyer’s market and underscoring the need for careful pricing. Buyers and sellers can both benefit from an experienced local agent, and Agent Pronto can connect them with someone who understands these conditions.
Learn more about what Shelter Island has to offer.
Shelter Island offers residents a serene seaside lifestyle with abundant nature, boating and outdoor recreation, and a close-knit community in a peaceful, walkable island setting.
Shelter Island combines quiet coastal living with convenient access to both the North and South Forks of Long Island. Reached by short ferry rides from Greenport and North Haven, it feels tucked away yet remains practical for year round residents and second home owners.
Daily life centers on the water and small scale services. Crescent Beach and Wades Beach offer family friendly swimming, while Crescent Beach / Sunset Beach is a favorite for evening views. Outdoor enthusiasts value the extensive trails and bird habitat in Mashomack Preserve, along with town landings that support boating and kayaking. The Shelter Island Public Library anchors community events and remote work needs with reliable workspace and programming.
On Ranboy Road and in the Heights, you will find casual restaurants, markets, and cafes that cover daily errands without leaving the Island. Families often look closely at the Shelter Island School and the town’s Parks and Recreation offerings when comparing neighborhoods. Proximity to nearby Greenport, Southold, Riverhead, Sag Harbor, and East Hampton expands options for dining, healthcare, and shopping while preserving Shelter Island’s quieter feel.
Because inventory is limited and each area of the Island has distinct rules, shoreline conditions, and access patterns, working with a local real estate expert can significantly reduce stress. Agent Pronto connects both buyers and sellers in Shelter Island with agents who understand these nuances and can guide each step with confidence.
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See why so many people rely on Agent Pronto to make their real estate journey a success.
“Jack was professional, responsive, and easy to work with throughout the process. He was always available to answer questions and made everything as smooth as possible. I appreciate his time and effort and would recommend him to anyone looking for a knowledgeable real estate agent.”
“Selling our home after more than a decade of memories while relocating from New York to Texas could have been incredibly stressful, but our realtors made the entire process feel manageable from start to finish. Their level of involvement was unlike anything we’ve experienced. They were engaged in every aspect of the sale, communicated constantly, and were personally present for every showing. We never felt like just another listing—they treated our home as if it were their own and were invested in getting us the best possible outcome. Their knowledge of the market, attention to detail, and proactive approach were invaluable. Whether it was preparing the house for showings, providing feedback, coordinating with buyers, or navigating negotiations, they were there every step of the way. No question went unanswered, and no concern was ever too small. Thanks to their hard work and dedication, we were able to successfully sell our home and make our move to Texas with confidence. In a profession where service can vary greatly, they truly set the gold standard. If you’re looking for realtors who are professional, knowledgeable, responsive, and genuinely care about their clients, look no further. We are incredibly grateful for everything they did and would recommend them without hesitation to anyone buying or selling a home. Five stars simply don’t do them justice. ++ Highly recommended!”
“Samantha was amazing. We've been looking for a second place now for two years, on and off again. We were not in a rush. Samantha was patient with our open timetable, available, responsive and informative. We would very much highly recommend her. I don't usually wrote reviews, but she deserves 5+ stars.”
“Lamar took the time to understand what was important to us as buyers. It was especially challenging since we were relocating to Long Island from Florida. He was patient and was there doing Video Tours with us. Lamar is a Realtor to have on your side.”
“Lori is amazing!!!! Couldn’t have found a more caring, understanding and friendly realtor. She listened to my requests, and I felt like she was very thorough with all of her follow up. She kept me up to date during the entire process of the sale of my home. A true professional who felt like a good friend.”
“You won't find someone more responsive , patient, diligent and sincere than Jay. His insight and honesty helped us walk away from a few houses we would have regretted purchasing as inventory got thin. He was right and he helped us close on a home we absolutely love! Thanks Jay!!!”
“Ryan is a knowledgeable real estate agent, with his guidance and expertise he was able to sell our home within 24 hours. We had the most positive experience and would highly recommend him to others.”
“Sal made the home buying experience as pain less as possible. He always responded to my texts or took my calls whenever I called him. He answered any and all questions I had. He was with us every step of the way from looking at houses all the way through the closing process. I wish there were more people like Sal in all walks of life. He may look young but has that old school mentality that is missing these days. I have already recommended Sal to my family and friends and would recommend him to anybody interested in buying or selling their home. I can honestly say that without Sal we would not be in our first home and I am eternally grateful for all he's done for my family.”
“My experience with Michael has been excellent. He is both experienced in how to effectively sell real estate and an expert in knowing how to deal with people. He always errs on the client's behalf. His knowledge is wide and his demeanor professional. As an Interior Designer and Architect, I found him Michael to be a real team member.”
Frequently Asked Questions
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There are more than 2 million real estate agents across the U.S., and you want to be sure the one you partner with is an experienced and trustworthy professional with strong local expertise covering the housing market in and around Shelter Island. Working with a proven agent will help you sell your home faster and for more money, and help you find your dream home at the best possible price.
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Choosing a real estate agent to help you buy or sell property is one of the most important decisions you’ll make in your lifetime. You want to make sure your agent is an expert in your area, has a proven record helping people buy and sell similar homes to yours, and is well regarded by their previous clients. Let us know a few details about the property you are selling or the kind of home you want to buy, and Agent Pronto will match you with trusted real estate agents that have the experience you need. And before you interview an agent, check out our top five questions to ask a buyer’s agent and listing agent.
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We consider performance metrics, close rates, specialties, and client reviews to qualify the best full-time agents. We then take the information you provide about the home you are selling or the kind of home you want to buy, and analyze the top local agents with the right experience for your specific needs. For more than a decade, we've helped hundreds of thousands of home buyers and sellers find the right agent. Get started now and find the perfect real estate agent.
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No. Agent Pronto is a free service for home buyers and sellers and you are under no obligation to work with our recommended agents. Find your Shelter Island Realtor® or real estate agent today.
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