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Wingdale, NY real estate

Compare top Wingdale 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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Wingdale real estate Market Report.

Information and statistics on the latest trends in the Wingdale real estate market. *

Quarterly Pricing Trends for Wingdale

Rolling three-month data ending on quarter boundaries when available.

Quarterly Pricing Trends for Wingdale Q4 '21 Q4 '22 Q4 '23 Q4 '24 Q4 '25 Q3 '26 Median sale price in Oct 2021 - Dec 2021: $219K Median sale price in Apr 2022 - Jun 2022: $233K Median sale price in Jul 2022 - Sep 2022: $365K Median sale price in Oct 2022 - Dec 2022: $435K Median sale price in Jan 2023 - Mar 2023: $125K Median sale price in Apr 2023 - Jun 2023: $285K Median sale price in Oct 2023 - Dec 2023: $265K Median sale price in Jan 2024 - Mar 2024: $170K Median sale price in Apr 2024 - Jun 2024: $385K Median sale price in Jul 2024 - Sep 2024: $275K Median sale price in Jan 2025 - Mar 2025: $263K Median sale price in Jul 2025 - Sep 2025: $465K Median sale price in Oct 2025 - Dec 2025: $570K Median sale price in Jan 2026 - Mar 2026: $549K Median sale price in Apr 2026 - Jun 2026: $365K Median list price in Jan 2022 - Mar 2022: $225K Median list price in Apr 2022 - Jun 2022: $324K Median list price in Jul 2022 - Sep 2022: $435K Median list price in Oct 2022 - Dec 2022: $136K Median list price in Jan 2023 - Mar 2023: $181K Median list price in Apr 2023 - Jun 2023: $329K Median list price in Jul 2023 - Sep 2023: $214K Median list price in Oct 2023 - Dec 2023: $273K Median list price in Apr 2024 - Jun 2024: $329K Median list price in Jul 2024 - Sep 2024: $357K Median list price in Jan 2025 - Mar 2025: $74K Median list price in Apr 2025 - Jun 2025: $403K Median list price in Jul 2025 - Sep 2025: $575K Median list price in Oct 2025 - Dec 2025: $600K Median list price in Jan 2026 - Mar 2026: $399K Median list price in Jul 2026 - Sep 2026: $502K Oct 2021 - Dec 2021 Median sale price $219K Median list price Unknown Jan 2022 - Mar 2022 Median sale price Unknown Median list price $225K Apr 2022 - Jun 2022 Median sale price $233K Median list price $324K Jul 2022 - Sep 2022 Median sale price $365K Median list price $435K Oct 2022 - Dec 2022 Median sale price $435K Median list price $136K Jan 2023 - Mar 2023 Median sale price $125K Median list price $181K Apr 2023 - Jun 2023 Median sale price $285K Median list price $329K Jul 2023 - Sep 2023 Median sale price Unknown Median list price $214K Oct 2023 - Dec 2023 Median sale price $265K Median list price $273K Jan 2024 - Mar 2024 Median sale price $170K Median list price Unknown Apr 2024 - Jun 2024 Median sale price $385K Median list price $329K Jul 2024 - Sep 2024 Median sale price $275K Median list price $357K Oct 2024 - Dec 2024 Median sale price Unknown Median list price Unknown Jan 2025 - Mar 2025 Median sale price $263K Median list price $74K Apr 2025 - Jun 2025 Median sale price Unknown Median list price $403K Jul 2025 - Sep 2025 Median sale price $465K Median list price $575K Oct 2025 - Dec 2025 Median sale price $570K Median list price $600K Jan 2026 - Mar 2026 Median sale price $549K Median list price $399K Apr 2026 - Jun 2026 Median sale price $365K Median list price Unknown Jul 2026 - Sep 2026 Median sale price Unknown Median list price $502K
Median sale price
Median list price
* Data provided by Redfin, a national real estate brokerage.
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Seller’s Market
Seller’s Market
Buyer’s Market
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25
50
75
100

Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Q1 2026).

Wingdale’s rolling three-month data shows notable shifts compared with a year ago. The median list price is down about 13 percent year over year, signaling some pricing relief for buyers. At the same time, new listings have roughly doubled, giving house hunters more options even though the number of active listings is holding close to last year’s level.

Looking at the latest period ending in September 2026, the median list price sits just over $500,000 with only two active listings on the market. This combination of higher inventory flow but very few homes available at any given time reflects a small, tight market where each new listing matters.

Recent history highlights how quickly conditions can shift in Wingdale. Median sale prices in past quarters have ranged from about $170,000 in early 2024 to over $570,000 at the end of 2025, while days on market have swung from single digits to nearly three months, and months of supply has varied from about 1.0 to just over 6.0. Those wide price and speed ranges, along with a current seller’s market reading, underscore how important local expertise is when setting expectations. Buyers trying to time an offer and sellers deciding on a list price can both benefit from Agent Pronto’s help finding a Wingdale agent who understands these dynamics.



Learn more about what Wingdale has to offer.

Wingdale offers residents a welcoming, tight-knit community with abundant outdoor recreation, convenient local services, and easy access to regional amenities, all wrapped in peaceful rural charm.

Wingdale immediately feels different from nearby commuter hubs like Poughkeepsie or White Plains. Here, daily life revolves around wooded hillsides, open sky, and a close community, yet you still have practical access to the Harlem Line at the Harlem Valley–Wingdale station for trips to New York City.

Outdoor lovers are drawn to Wingdale’s proximity to Harlem Valley Rail Trail access points and the sweeping scenery of Pawling and Beekman. Residents make good use of nearby Dover Plains Library and local parks, while weekend routines might include breakfast at a local diner in town or exploring the shops and cafes of Amenia. The Dover Union Free School District serves the area and is an important anchor for families considering a move.

Housing in Wingdale ranges from older farmhouses and modest ranch homes to newer construction on larger lots. Inventory can be tight, and well priced properties often move quickly compared with some areas of Dutchess County. Buyers benefit from understanding local micro markets near the train station and main corridors, while sellers gain an edge by preparing for inspections and pricing with recent sales in mind.

The right local real estate agent can interpret subtle neighborhood trends and timing, and Agent Pronto can connect both buyers and sellers in Wingdale with that trusted expertise.

Find your Wingdale real estate agent today →


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“Trish was incredible to work with. As a first time homebuyer she made the process so easy and smooth from start to finish. Trish went above and beyond to show me several properties and was always accommodating of my tricky schedule. Trish also sent weekly updates by email with progress and next steps which took the stress out of the home buying process! Trish was super responsive morning noon and night. I highly recommend her for anybody looking to buy or sell!!!”

sross3190 ·

Photo of Tricia Farin
Real Broker CT, LLC
“I haven’t even purchased a home with Robert yet, and I can already say without hesitation that he has earned every one of these five stars. When I first started working with Robert, I wasn’t even entirely sure what my next chapter looked like. I went from considering renting, to buying a home, to exploring an income-producing property, and now to seriously considering building my dream home. Through every pivot - and there have been a few - Robert has never made me feel like I was wasting his time or needed to hurry up and make a decision. He has simply met me where I am, answered what feels like a thousand questions, educated me, encouraged me, and helped me think through what makes the most sense for my life and my future. And he has quite literally walked through homes with me and told me, flat out, “Do not buy this house.” That matters to me. Robert is not interested in simply selling me a home so he can collect a commission. He has been very clear that he does not want to be part of the worst financial decision I ever make. He wants to be part of the best one. That means he will point out what I may not see, tell me when something gives him pause, and steer me away from a property if he believes I would regret it later - even if that means we keep looking. I cannot overstate how much trust that builds in a relationship with a real estate agent. What also sets Robert apart for me is his commitment to veterans. Robert is an Army veteran himself, and his knowledge of VA benefits, VA home loans, and the resources available to veterans goes far beyond knowing how to complete a real estate transaction. He genuinely wants veterans to understand and receive the benefits they have earned. In my case, his knowledge of benefits 100% changed my life. During one of our conversations, Robert encouraged me to pursue a VA disability claim for an injury that occurred when I was in service. This wasn’t even something I knew was available to me. He helped me understand that these benefits existed for all veterans- not just those who were injured during deployment or combat. I never knew this as I got out in the early 90’s and this wasn’t explained to veterans then. I followed his advice, filed my claim, and ultimately received a VA disability rating that, without question, changed my life. There was no commission attached to that. No house sale.. Nothing in it for him other than knowing he was helping someone. He simply saw another veteran who might be entitled to benefits she had earned and took the time to point me in the right direction. I will never forget that. Robert is knowledgeable, patient, straightforward, and incredibly generous with his time and expertise. He’s also a family man, and I think that shows in the way he approaches his clients. He doesn’t seem interested in simply putting people in houses. He wants to understand what you are trying to build for yourself and your family, and then help you make the smartest possible decision about how to get there. So yes, someday I fully expect this review will include the story of the house Robert helped me buy or, at this rate, the dream home he helped me build. But he has already helped me with something far bigger than a real estate transaction. If you are a veteran looking to buy a home, particularly someone who isn’t completely sure what benefits or opportunities are available to you, I cannot recommend Robert highly enough. And veteran or not, if you want an agent who will actually listen, educate you, protect your interests, and stay alongside you until the right decision becomes clear, Robert is exactly the kind of person you want in your corner.”

Becky Saxe ·

Photo of Robbie Brestovansky
EXP Realty
“Lisa Jeanneret of Corcoran Country Living was the listing agent for the home we sold in Mahopac, which sold very quickly. Lisa also helped us find our new home in Hopewell Junction, which was not easy. We wanted to move closer to family & friends in the Wappingers/East Fishkill area. Lisa stuck with us for over a year looking at several houses, even when my wife and I were ready to give up, until we found the right match. Lisa has a lot of local knowledge and was able to recommend various resources to help conclude our sale and purchase, including lawyers, engineers and contractors.”

Ralph Savarese ·

Photo of Lisa Jeanneret
Corcoran Country Living
“Buying a home is one of the biggest decisions you’ll ever make. Bruno made the process less stressful and I can’t imagine having gone through the process with anyone better than him. From day one, he was incredibly patient, never once making us feel rushed or pressured. We looked at many homes out several offers and no matter how many questions we had or how many showings we requested, he was always available and happy to show us the houses. What impressed me the most was how much he genuinely cared about making sure we made the right decision. He took the time to educate us throughout the entire process, explaining things in a way that was easy to understand and making sure we felt confident every step of the way. His knowledge of the market was incredible. He told us that interest rates were likely to go up and that home prices would continue to increase, and he was absolutely right. The market won’t be the same in a few months he kept telling us. Thanks to his advice, we felt confident moving forward when we did, and looking back, we’re so grateful we listened. More than just being a great realtor, he was someone we completely trusted. He always had our best interests at heart, was honest, responsive, and genuinely invested in helping our family find the right home. Some realtors want a quick purchase and to move on. He pointed out potential issues and recommended several services for after the home purchase. We’re incredibly thankful for everything he did for us and couldn’t recommend him more highly. If you’re looking for someone who is knowledgeable, trustworthy, patient, and truly cares about his clients, you won’t find anyone better than Bruno.”

michaelopz ·

Photo of Bruno Ruiz-Castano
ADCNY Realty Corp
“From the moment we met Rosanna, we knew she was our person. She comes with a calm that is comforting in the chaos of figuring out a milestone as hefty as a new home. She listened to our needs and wants and found us potential homes that fit the mark. We really felt like the homes we were visiting fit our vision plus or minus a few things. We bid on 3 homes and all of them fit our criteria exactly. Rosanna kept in constant communication without being overbearing or overwhelming. She answered our questions quickly and gave us recommendations to build out the rest of our team- which turned out to be the best team in the business. On a personal level, Rosanna set up showings for us for a total of 24 homes in the span of 8 months. She never made us feel like we were being picky or difficult and understood the gravity of choosing a starter home. I cannot emphasize how amazing it felt to be seen, understood, and given patience in this process. Along the way, she really got to know us, making suggestions based on each of our personal likes and dislikes. That's not a MUST in realty, but an added bonus. Rosanna brought a lot of laughter to the process that can seem daunting adn stressful. This skill eases a ton of the tension that comes with the search. I highly recommend Rosanna as YOUR person to help you find your new home.”

Jeyandini Fernando ·

Photo of Rosanna Fabre
Keller Williams Realty Partners
“Helen and Dan did such an amazing job assisting me in my search for an apartment! As a first time renter, I had no idea how any of it worked. Helen and Dan walked me through it, were extremely responsive, and found my dream place. They are some of the most professional people I’ve ever had the pleasure of working with, and would recommend them to anyone who needs real estate assistance. Thank you so much for everything!”

jprestopino ·

Photo of Helen Schweitzer
Helen Schweitzer Realty LLC
“We had an incredible experience working with CK team at eXP Realty!! From start to finish both Catia and Kayleigh went above and beyond in every possible way. Their communication was truly outstanding—no matter the time of day, They were always available to answer our questions, walk us through details, and make sure we felt confident every step of the way. What really stood out was how hard they fought to help us get the home we have now. both were determined, strategic, and completely dedicated to making it happen for us—and thanks to their persistence and expertise, they succeeded. We genuinely felt like they were just as invested in our dream as we were. They also put in so much time and effort behind the scenes to ensure everything was running smoothly. From coordinating details to keeping us informed, they made what could have been a stressful process feel organized and manageable. One of the things we appreciated the most was that every step, they made sure we felt supported and never once pressured us into making a decision or going beyond what we were comfortable with. Their priority was always what was best for us, and that level of patience, honesty, and commitment made the entire experience feel both exciting and secure. We couldn’t have asked for a better experience, and we’re so grateful for everything they did for us. We love our new home!! Highly recommend them to anyone looking for someone who truly cares and delivers results!”

zuser20250228054355082 ·

“Michael was great to work with during the home buying process. He kept me informed throughout the process and helped negotiate a prolonged sale that took some unexpected turns. Thank you, Michael!”

claireneville13 ·

Photo of Michael Santarpia
KFortuna realty
“I am glad that I contacted Agent Pronto, so I got to connect with Martha Gaffney. It has been a great pleasure working with her and she worked really hard to get me a house which is well worth it. Thanks Martha and thanks Agent Pronto for the opportunity. ”

Shreen B. · Bronx, NY

Photo of Martha & Niall Gaffney
Old Towne Living NY Inc.
“Working with Curt was amazing! I chose him to sell my house because he made me feel comfortable from our very first meeting, even though I was selling the house I inherited as is and it needed a lot of work. He was incredibly patient throughout the entire process, especially when dealing with a difficult buyer, and he guided me every step of the way. I would absolutely recommend Curt to anyone looking for a realtor.”

Elizabeth Boisi ·

Photo of Legacy Land & Homes
Legacy Land & Homes, LLC
“Cassandra is an elite broker. She does excellent work. I was picky so I had specific requirements that were challenging for other brokers. I would recommend her to anyone looking in the area. You will not be disappointed!”

cdallas144 ·

Photo of Magnolia Real Estate
eXp Realty Magnolia Real Estate
“Alban helped me and my family to find our house...he was really patient and helpful during the entire process.... We bought the house almost 2 months ago and since this is our new house there were many things that we needed help with and he been continuing helping and answering our questions or concerns....100% recommended.”

oskrx227 ·

Photo of Alban Preldakaj
RE/MAX Distinguished Homes & Properties
“BEST IN THE TRADE...GOAT. Rebecca Kane is very professional and knowledgeable in the real estate market. She went all out to make sure everything step throughout the process went smoothly. She treated us like FAMILY. EXCELLENT SERVICE!!!!!”

JacquelineTurner91 ·

Photo of Rebecca Kane
Keller Williams Hudson Valley United
“I wish there were more than five stars to rate! Diana is patient, and honest. Her communication is quick and incredibly professional. We used Diana to both purchase and sell a home. She talks you through any of your concerns and always makes sure you feel comfortable and confident in all the decisions of what can be a stressful process”

iblieb ·

Photo of Diana Murphy
HomeSmart Homes and Estates
“Karen worked with me to sell 7 properties. Karen responds to every message and email immediately, goes above and beyond, and is simply a pleasure to work with. Highly recommended.”

stevenfruchter1989 ·

Photo of Karen Zayas
Century 21 Alliance Realty Group
“Had a very positive experience with Gigi Finan, the broker to whom I was referred. She kept me informed and kept the transaction moving. She showed me a range of properties as they became available.”

David L. · Peekskill, NY

Photo of Gigi Finan
Houlihan Lawrence Real Estate
“Dina was amazing to work with, her knowledge and expertise truly helped in selling my co-op. Co-op sale can be tricky and hard and working with Dina truly made it as easy as possible.”

ttallevi ·

Photo of Dina Bahr
K. Fortuna Realty Inc.
“Jeff was awesome to work with. Jeff did a great job selling our home. Our home sold in 3 days. I would definitely use Jeff again and I highly recommend him to anyone that needs a Real Estate Agent. I give him 10 stars. Debbie & Vito”

sweepea1931 ·

Photo of Jeff Eraca
Real Broker
“Joann represented me both in selling my existing home at the time and in purchasing my presnt one. She was very responsive to my inquiries, knowledgeable about local rules, regulations, and procedures, and effectively acted on my behalf to theother parties agents and lawyers. In addition, she was very pleasant and easy to deal with.”

johnpfinn10 ·

Photo of Joann Krieger
K Fortuna Realty Inc
“Mario has been my agent over 20 years..he always managed to send me great tenants..with prompt and total respect for me and them..our selling experience was smooth and he was responsive to our needs and always kept us informed and up to date with all data selling a home..I will continue to work with him in future projects for his expertise on all properties as the market progresses”

zuser20150119113305210 ·

Photo of Mario Sclafani
RE/MAX Classic Realty

Frequently Asked Questions

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 Wingdale. 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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