We analyze top real estate agents in Chester and across the country to find you the most proven local agents, for free.
Agent Pronto analyzes transaction data, specialties, client reviews, and more to find the best agent for you. Updated for September 2025. *
* 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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“Nicole was absolutely fantastic in helping find the house of we wanted. She went above and beyond, helping us with any requests or questions that we had. I would definitely recommend Nicole to friends/family and use her the next time we have to buy/sell as house.”
“Buying a house with your mom as your realtor could go one of two ways - either you end up stuck in her basement / guest room forever, or she gets you into the perfect place. Luckily for me, Beth nailed it. She was on top of everything, quick to answer my million questions, and made the whole process way less stressful than I thought it would be. She fought to get me the best deal and made sure I didn’t settle for anything less than what I really wanted. If she works this hard for her own kid, imagine what she’ll do for her clients - we’re talking answering calls at all hours, catching things most people wouldn’t even think to look for, and negotiating like she’s on a personal mission against overpriced houses.”
“Sold my house when others couldn't. Sold it fast for asking price. Doesn't get any better than that!”
“Working with Nael on the purchase of my new home in Walden was a fantastic experience. He was patient, knowledgeable, and truly had my best interests at heart. From the first showing to the final walkthrough, Nael made sure everything went smoothly. He helped me find the right home, negotiated effectively, and stayed on top of every detail. I’m so grateful for his support and would recommend him to anyone looking for a trustworthy and dedicated agent.”
“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.”
“Matthew is very knowledgeable as a broker, He told us what to expect and what needed to be done to get the most of what we were asking for. He guided us every step of the way and made me feel comfortable through the process. He is very reliable and always kept me informed throughout the sale of the house. I would highly recommend him him to all my friends and will use him in the future for the purchase of my second home. I can definitely say he is a great asset to your company.”
“You put me in touch with very good realtors. I chose Rebecca Kane from the recommendations. She did an excellent job.”
“Travis is the best. He loves his job.”
“Arleen was pleasant, knowledgeable, and proactive. I enjoyed working with Arleen. She did things the way I would have. She was direct, patient to a point, and professional. The process did not lag on Arleen's watch. Highly recommend.”
“Patrick Taylor made the task of selling my home painless. He kept me informed through the entire process and I would recommend him to anyone trying to buy/sell their home. ”
“We thought Hermi Aquino was an exceptional realtor—one we recommend to others without hesitation.”
Information and statistics on the latest trends in the Chester real estate market, updated for September 2025. *
The typical home value in Chester is projected to be $338,130 for the month of September. August’s finalized data reported the typical value of a home in the city to be $358,750—up 21.61% over the previous 12 months. For comparison, county-level data pegged home values at $456,600 in Orange County for the most recent reporting period. That number is expected to float around $455,150 in September.
Chester had 6 new listings and 3 listings that went under contract in August, increasing the area’s total available inventory to 9—up 50.0% from the previous month. Inventory is projected to have further increased in September.
Of those 9 active listings, 11.11% reduced their price in the month of August. The median listing price for homes in Chester fell 21.3% from July to August, bringing the current median listing price to $364,000. Based on projected data for September, listing prices may continue to fall.
The number of days that homes have been on the market prior to going under contract rose year-over-year. In August 2025, the median time for a listed property to go pending was 38 days, compared to 20 days in August 2024. However, in recent months the median number of days from listed to pending appears to be falling. That trend is predicted to have carried through to this September.
Market gauge is calculated based on the the number of active listings divided by home sales over the most recently available reporting period.
Chester offers residents a welcoming, family-friendly community with small-town charm, strong local services, ample parks, and easy access to nature and nearby amenities.
Chester offers a delightful mix of small-town warmth, scenic surroundings, and a lifestyle colored by both history and modern comfort. The town’s unique character is evident as you stroll along Main Street, where local shops and eateries cater to every palate. Families appreciate the convenience of the Chester Union Free School District, which supports learning with dedicated teachers and enriching programs. The area's legacy is showcased at the Chester Historical Society, where residents gain a deeper appreciation for their hometown roots.
Recreation is easy to find at Goosepond Mountain State Park with its inviting trails perfect for all ages, and the well-loved The Castle Fun Center provides entertainment options from go-karts to mini-golf. For neighbors who love homegrown goods, the Sugar Loaf Arts & Crafts Village in nearby Warwick offers a vibrant arts scene and regular events.
Living in Chester means being close to destinations like Middletown and Orange County, gifting residents with easy access to broader amenities and shopping. With its rural charm balanced by essential conveniences, Chester continuously attracts those seeking community spirit and tranquility.
Whether you are considering buying your first home or planning to sell and move on to new adventures, engaging with Agent Pronto can help you connect with the ideal real estate professional for your needs in Chester.
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 Chester. 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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