“Nael was incredible throughout the entire process in helping us sell our co-op studio. Would recommend and plan to use his services in the future.”
CENTURY 21 Elite Realty
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We analyze thousands of real estate agents in Wingdale and nationwide to find you proven local professionals, for free.
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Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for July 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.
Median sale price
Median list price
Quarterly Pricing Trends for Wingdale
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for Wingdale
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Inventory and Sales Activity for Wingdale
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
Quarterly Inventory and Sales Activity for Wingdale
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
Quarterly Inventory and Sales Activity for Wingdale
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
10
Seller’s Market
Seller’s Market
Buyer’s Market
0
20
40
60
80
100
0
25
50
75
100
Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Mar 2026 - May 2026).
Year-over-year trends in Wingdale show a striking shift in prices and pace. The typical home value in this rolling three-month view is about 284 percent higher than a year ago, highlighting how volatile a small market can be. At the same time, the share of homes selling above list has dropped to zero, down from last year.
Looking at the latest rolling period ending in May 2026, conditions reflect a tight seller’s market with very limited options. Only one active listing and one home sold are recorded, and the market gauge places Wingdale firmly in seller’s territory. Homes are moving more quickly, with the median days on market down to 25, compared with much longer times seen in past years.
Recent history underscores how quickly dynamics can change here, with days on market swinging from 81 days at the end of 2023 to as low as 13 days by mid-2024. Sale-to-list ratios have also softened, with the current average around 91 percent, suggesting buyers may have some room to negotiate even in a low-inventory environment. With such small numbers driving big percentage changes, local expertise matters a lot when interpreting value and timing. Buyers trying to enter this tight market and sellers aiming to price correctly can both turn to Agent Pronto to connect with a local agent who understands these nuances.
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.
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“Ricky's experience in the local area, hard-working attitude and positive demeanor make him a great choice for perspective buyers in the Watetown/Fort Drum area!”
eXp Realty
“Después de una larga jornada para lograr comprar nuestra casa, por fin hemos llegado a la meta. 🏡 Queremos agradecer a María de Osorio por su apoyo durante todo este proceso. Siempre estuvo disponible para responder nuestras dudas y preguntas, brindándonos orientación y tranquilidad en cada paso. Definitivamente la recomendaremos a nuestros amigos y familiares. ¡Gracias por ayudarnos a hacer realidad este sueño!”
Century 21 Elite Realty
“Working with Nicole Issac was an absolute pleasure from start to finish. She was outstanding in every aspect of the process and truly went above and beyond to help us secure our property. Her patience, professionalism, and dedication made what could have been a stressful experience feel smooth and manageable. Nicole took the time to answer every question, explain every detail, and guide us through each step with confidence and care. No matter how many concerns or requests we had, she remained calm, responsive, and supportive throughout the entire journey. Her knowledge of the market, attention to detail, and commitment to our needs were exceptional. We always felt like a priority, and it was clear that she genuinely cared about helping us find the right home. I would highly recommend Nicole Issac to anyone looking for a trustworthy, hardworking, and patient real estate agent. She exceeded our expectations in every way, and we are incredibly grateful for all of her help.”
Century 21 Full Service Realty
“It was a pleasure to work with Crystal. She was knowledgeable and very responsive to requests. She shared updates as they occurred and came to our home for most of the paperwork signings. From listing to closing it was about 5 weeks to sell our property with 8 offers the first week! Thank you to Crystal the whole process went smoothly. We are very happy. We would list with her again in the future. Thank you. L”
Century 21 Jackson Real Estate
“Claudia was nothing short of amazing to work with during the process of looking for our first home. The whole process was made so much easier knowing we had someone like Claudia looking out for our best interests. She was always available to answer questions, offer guidance, and let us know when something that fit out criteria was available to visit. I would recommend Claudia without hesitation to anybody looking for a real estate agent.”
Century 21 Elite Realty
“I had an incredible experience working with Samuel Okine for my first NYC apartment. From start to finish, he was attentive, knowledgeable, and genuinely invested in helping me find the perfect place. Sam's guidance made the entire process stress-free, and I couldn't be happier with my new home. I highly recommend Sam to anyone looking for a trustworthy and professional agent in New York City!”
The Agency Real Estate
“A true professional. Alana is great at what she does .”
Signature Premier Properties
“Brandy was fantastic every step of the way and stayed consistent throughout this entire process. Highly recommended for anyone in need of a realtor.”
Century 21 Elite 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. ”
Old Towne Living NY Inc.
“I have never seen a realtor agent go above and beyond like Sandy. I willl never work with another agent other than Sandy in the future”
Century 21 Scala Group
“Vesna is a top notch Broker and will always stick to her in the future and will also recommend her to anyone who needs real estate broker”
Century 21 Elite Realty
“My realtor was incredible and very helpful throughout the process of selling my home.”
HomeSmart Premier Living Realty
“We were referred to the Carrillo Agency and worked with Brandi Everett. She was great helping us through the entire buying process. She made sure we were covered by a colleague when she couldn't be there and guided us through the search, bidding and closing process. We can't thank Brandi enough for her help.”
Coldwell Banker
“Virginia worked well with me to sell my home. Communication was easy and she was always on time”
Century 21 Alliance Realty Group
“Sold my house when others couldn't. Sold it fast for asking price. Doesn't get any better than that!”
eXp Realty
“I enjoyed the extra mile as well as ear. Positive when needed, clarity when asked. Imelda's professionalism and experience provided great value and insight, when a smooth situation became more challenging. Imelda has experience that was significan to me, I don't think I would've done this without you. Thank you.”
EXP realty
“Happy to find an agent who was familiar with multi-family across the nation for my purchase.”
Keller Williams Realty Greater Rochester
“Kevin was very professional and knowledged. He assisted me so much throughout this stressful buying process and worked in any way possible to decrease the load on my shoulders. I would recommend Kevin to my family and friends.”
eXp Realty
“On a whim, I used Agent Pronto, as I was in the market to sell my current apartment. I was connected with Joana Chu, a highly recommended realtor and it turned out to be one of the best decisions I have made.”
Home Court Real Estate LLC
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 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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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 Wingdale Realtor® or real estate agent today.
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