We analyze thousands of real estate agents in Southold and nationwide to find you proven local professionals, for free.
Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for October 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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Information and statistics on the latest trends in the Southold real estate market. *
Jul 1, 2026 - Sep 30, 2026
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month supply and activity totals for the selected period.
Rolling three-month supply and activity totals for the selected period.
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).
Southold’s rolling three-month data through September 2026 points to more options but shifting activity. Active listings are roughly flat year over year, with 79 homes on the market, yet new listings are down more than 10 percent from a year ago. Pending sales have also slipped compared with last year, even as closed sales are holding steady around 20 over the recent three-month window.
Prices are showing resilience even as inventory and contracts adjust. Typical home values are almost 5 percent higher than a year ago, while the median list price has jumped about 20 percent year over year, suggesting sellers are still confident in what buyers will pay.
Time on market and supply trends help explain the mixed signals. Homes are selling faster than a year ago, with the median days on market falling to 44 days, and the share of properties closing above list has edged up to about 30 percent. At the same time, months of supply has more than doubled year over year to about 6.6 months, moving conditions closer to balance despite the area still being labeled a seller’s market. With these crosscurrents in Southold, both buyers and sellers can benefit from Agent Pronto’s help in finding an agent who understands the latest local trends.
Southold offers residents a picturesque coastal lifestyle, a supportive close-knit community, and rich local experiences—from outdoor recreation to culture and dining.
Southold stands out from other North Fork communities with its blend of historic waterfront hamlets, active farms, and a strong year round local identity. While nearby Riverhead and Greenport draw more passing visitors, Southold leans into a quieter pace, where residents tend to know each other and seasonal tourism supports, rather than defines, daily life.
Life here revolves around the water and the land. Boaters and kayakers take advantage of Southold Bay access and nearby Orient, while local tasting rooms like Bedell Cellars highlight the region’s winemaking reputation. The historic heart of the community is captured at the Southold Historical Museum, and families appreciate resources like Southold Junior-Senior High School and the Southold Free Library along Main Road.
Outdoor time is part of the local rhythm. Residents frequent Founders Landing Park for bayfront swimming and picnics, explore trails and shoreline at Cedar Beach Park, and visit nearby Mattituck for additional dining and services.
Because Southold’s inventory is limited and highly specific by location, water access, and historical character, timing and preparation matter. Whether you are a long time resident thinking about selling or planning a move to the North Fork, connecting early with the right local expert through Agent Pronto can help you navigate the market with confidence and clarity on both the buying and selling side.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“Thomas was such a pleasure to work with. I have worked with agents and the past and he superseded all of my expectations by far! Was very knowledgeable about the market and the area, priced property fairly, great negotiation skills. I would highly recommend.”
“I was a North Carolina transplant looking to sell my property in central Long Island, NY. Samantha had connections to a an excellent real estate attorney, a junk removal service that worked at an acceptable cost and on short notice. She was knowledgeable, responsive, and really went above and beyond to make sure I felt connected - in spite of navigating the process from states away. I never felt a need to go up to NY and handle something myself. I would use again if I go back to Long Island.”
“John went above and beyond throughout our home-buying journey, and we cannot recommend him highly enough. His dedication, responsiveness, and genuine care made us feel supported every step of the way. Whether it was day or night, he always made time to answer our questions, no matter how small, with patience and attention to detail. John made what can be an overwhelming process feel smooth and manageable. We always felt like a priority, and we truly couldn’t imagine working with anyone else. If you’re looking for someone who will go the extra mile and make your home-buying experience as stress-free as possible, John is the person you want by your side!”
“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!”
“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.”
“I couldn't be happier with how this sale was handled. Selling my childhood home was an emotional process, and having a realtor who understood that made all the difference. Communication was excellent from start to finish — I always knew what was happening and never had to chase for updates. What stood out most was how respectful Jill was of my preferences. She used my preferred method of contact every time and genuinely listened to how I wanted the sale to be conducted, rather than pushing her own agenda. That level of attentiveness made a stressful process feel manageable. I would highly recommend Jill Garton to anyone looking for a professional who combines strong communication skills with real respect for their clients' wishes.”
“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!”
“Ashley was an exceptional partner in both the sale of our previous home and the purchase of our new one. From the very beginning, she brought a level of professionalism, knowledge, and calm confidence that made the entire process feel manageable and even enjoyable. She understood exactly what we were looking for, offered thoughtful guidance at every step, and never hesitated to go the extra mile to make sure we felt informed and supported”
“Daniel did great job at helping me and my family land a house in Long Island! He’s super knowledgeable and always willing to help out. We have always treated him like a family member!”
“It was our pleasure to work with Robert Stumpo and we would do so again. As out-of-town clients, we appreciated his willingness to stop by properties as needed, take videos and photos, and serve as a local liaison. He gave us local insider tips and helped us choose the right locations and condos for us. He was persistent in connecting with the seller’s uncommunicative agent and negotiated a rebate from his own fees to correct an issue he didn’t cause. He even offered to help keep an eye on our new condo before we move in. Truly above and beyond!”
“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.”
“My wife and I had a great experience working with Dewey while relocating from the West Coast to Manhattan. He was professional, responsive, and a clear communicator throughout the entire process. He provided valuable insight into NYC real estate, neighborhoods, and even specific buildings, arranged virtual tours for us, and seamlessly coordinated with all parties involved. Dewey's thoroughness and steady guidance gave us confidence, especially when walking us through the board application and ensuring nothing was overlooked. He truly set the bar high for what we expect from a realtor. Highly recommend!”
“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.”
“Kerry is an amazing person who genuinely cared about my husband and myself as we took a large step into our future. She worked with our busy schedules and gave amazing advice to set us in the right direction for what we were looking for. We would not be in the house we are in today without the effort care she took with our future. I would recommend her to anyone, but first time home buyers for sure as it's great to have someone backing you up that's as knowledgeable and helpful as her!”
“Knaggs is amazing realtor, he has an great personality and is patience with his clients He doesn’t rush or try to sell you a home just to make his profit, very understandable when it comes to what your looking to buy I highly recommend him. I just purchased a new home and Im so excited he is the best.Im very satisfied with his work, I also was recommended through a friend. His team is great too!!! Thank you knaggs!!!!”
“Stephanie was available start to finish, 24/7. Questions that needed answers -she either knew or got. From dealing with realtors to the bank to attorneys, she made sure every "T" was crossed and "I" was dotted. She was very knowledgeable and always acted in my best interest. Great personality, attitude and highly skilled negotiator.”
“Andrew was great! He held our hands every step of the way and was always there with any questions we may have had. He did not make you feel like you were being annoying when you constantly text him with questions. And if the lawyer didn’t get back to us right away Andrew would get us the answers. He made sure the house was priced right so it would sell .He also made sure closing went as smoothly as possible by keeping us informed and up-to-date with everything that was going on and what was needed. We would definitely call Andrew again if we needed a real estate broker, so worth it!”
“Mary Gonzalez was truly exceptional Real Estate Agent. Honestly, I was impressed with her level of knowledge and the amount of data that she had about the market. She knew where to look for information and gave me answers immediately when I needed them. I would sincerely recommend her because when buying a house, the experience of the agent is very valuable to avoid bad decisions. By way of background, I am a first-time home buyer. I had no idea about the process whatsoever when I first started taking a look at homes, or what to expect throughout the process, but Mary helped me!!! Mary will work with you to make your desires a reality. She has a great team. They made the selling process so easy and helped me understand what was going on every step of the way. Moreover, She is honest, diligent, kind, responsible, a very good communicator and explicit. She will always tell you the truth of things without hiding her point of view about a house and its conditions. Honestly, we loooooved working with Mary! Thank you so much for everything!!!!!”
“Cynthia took me to see two apartments that were within my budget and in nice buildings, and helped take me through the application process without a hitch. In a town where there are so many pitfalls to apartment searches and renting she was a great agent to work with and made me feel secure & supported throughout. Can't recommend her highly enough!”
“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.”
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 Southold. 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.
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.
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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