“We have worked with Mallori before and wouldnt have it any other way. She is amazing at her job and goes above and beyond for her clients. Looking forward to working with her again in the future!”
- Agent Pronto
- South Dakota
- Chester
The best way to find top real estate agents in Chester, SD
We analyze thousands of real estate agents in Chester and nationwide to find you proven local professionals, for free.
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Compare top Chester real estate agents.
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.
The easiest way to find a top agent you can trust.
Sell faster. Buy smarter. Get matched with proven agents who know your market—all for free.
- Tell us what you need.
- Answer a few quick questions about your real estate goals.
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- We’ll find you top local agents based on performance, expertise, and customer reviews.
- Connect and compare.
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- Whether you’re buying, selling, or both, you’ll have a proven expert on your side.
Learn more about what Chester has to offer.
Chester offers residents a welcoming, close-knit community with convenient services, active local events, and ample outdoor recreation.
Chester stands apart from larger nearby communities like Madison and Sioux Falls with its small scale, open skies, and strong sense of local identity. Here, neighbors recognize each other at the post office and ballfield, and grain trucks and fishing boats share the same country roads.
Life in Chester revolves around school, sports, and outdoor time. Families value the close connection to Chester Area School District, where classrooms are small and Friday nights center on community events. Anglers and boaters head to nearby Brant Lake and Lake Madison for fishing, water sports, and quiet evenings on the shoreline. Local worship and social activities create additional ties that keep long‑time residents and new arrivals connected.
Daily needs are met in town or on quick trips to Dell Rapids and Brookings, while bigger shopping or specialty services are easily reached in Lake County. The pace is slower, yet internet and highway access keep work and learning connected to the region.
In a market this small, homes can move quickly or appear only occasionally. Being prepared with a real estate professional who understands Chester’s timing, pricing, and off‑market opportunities is essential. Agent Pronto can connect both buyers and sellers with the right local agent so they are ready when the next opportunity in Chester appears.
Trusted by over 500,000 buyers and sellers.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“I would recommend Jess Jager to anyone looking to sell a house. She was an excellent communicator from day one. She listened to our initial needs, and our feedback along the way, and always had our best interest in mind. Jess was amazing to work with.”
“Greg was so awesome! He guided me through buying my first my first home. He answered any and all questions I had and helped me through every step of the way!”
“Deena was great to work with while looking for a house. Fast to respond, willing to find houses in my price range and criteria, and helpful with any questions I had during the process.”
“I worked with Amy several years ago on the sale of my home and purchase of a new home and she was fantastic. We were so impressed with her that when my father passed away and my mother was looking to downsize, there was no question that we would return to Amy for assistance. She was incredibly kind and supportive during a difficult time. We fully trusted her knowledge and ideas. We quickly found the perfect place and Amy was instrumental in helping us get a great deal. In addition she was able to get my mother’s home sold within 1 day. She is kind, wonderful to work with, made things fun, and is generally concerned about the welfare of her clients. We would recommend her to anyone. We love Amy!!”
“We couldn't have asked for a better experience. . Roy helped us with both selling and purchasing a home, which is stressful regardless of circumstances. He is professional and represents his clients well. He is quick to respond to questions and helps troubleshoot issues or "to do" items. He provides realistic and honest market knowledge. Very highly recommend.”
“Ryan is exactly what we needed as a realtor. He’s was excellent in helping make the process of buying a house a wonderful experience. I would recommend Ryan to anyone.”
“Casey and Jon did an amazing job! With their help, I received an offer in less than 1 week of listing! They were extremely knowledgeable and kept the process moving smoothly clear through the final day of selling!”
“Jessica was amazing to work with, she went above and beyond to get us into the house that we purchased. She is honest and straightforward and that was very important to us when purchasing a home. Would highly recommended Jessica to anyone looking to buy a home.”
“Amy was absolutely awesome to work with! Her responsiveness and unbiased knowledge and opinions were exactly what we needed when we needed it! She was great with negotiations and truly helped us all the way through the closing! I would recommend her to anyone who is looking to purchase or sell a home! Amy thanks for helping us with our first home and getting us into our dream home!”
“Words can't describe how grateful we are to Julie and her team. She had so many resources to help us out as first time home buyers. She really listens to our needs and wants and she's super patient, didn't rush us at all. She was very thorough throughout our home buying process, everything went so smoothly. Would definitely recommend Julie and her team, especially to first time home buyers!”
“We met Toni at a showing and got a great vibe from her. She was patient and worked to understand what we were looking for in a home. She brought certain homes to our attention that had the key points we mentioned. It was relieving having someone on our team during this stressful process. She would jump to show or talk about things at ANY time. She is definitely a go-to person. Very reliable.”
“We’ve bought and sold lots of property in many states; but Larry has to be one of the best RE agents with which we have worked. Very motivated, non-pressuring, and looking out for our best interests. We really appreciated his honesty and attention to detail.”
“I cannot say enough good things about John! My significant other and I met John about a year and a half before we had any plans of selling our two properties with the plan of eventually buying a house together. John came over did a market analysis of my significant others home and gave us some pointers on where to put our money to improve minor issue, at the time we were not selling and John went above and beyond to help us with potentially nothing to gain. Once we were finally ready to put the home on the market we did not hesitate to use John. He was kind and very knowledgeable about the market, every step of the way John rocked it! He sold our property within record time and cared about us as human beings. 6 months later we started looking occasionally at houses coming on the market, we were doing minor repairs on our second house to get it ready to eventually list. At this time “we were not looking to buy” (let’s be honest we were but didn’t know it ourselves?) my significant other and I had multiple different ideas on the perfect house making it very difficult to pin point what we would actually buy. We would find a property we were interested in and at a moment’s notice John would get us in. John could of put pressure on us multiple times to buy houses that were not right for us but John didn’t, he cared about us and wanted us to buy the house that fit our direct needs and long term goals. John didn’t want us to settle for something and regret it later, John must have walked us through a ton of houses and did so with a smile on his face, when it came time to buy John was on it and we got our dream home. After buying we still had our second property to list and sell John again was great he got it on the market in record time seeing as we were really not fully prepared to list it and it sold within 24hours of hitting the market after the fact we started doing renovations on our new home (it had an unfinished basement) John was very interested in our progress and offered to come out and do an analysis once our unfinished level was completed so we could see the benefits of the remodel we were doing, we were again impressed with John, he cares about us and is excited about what we are doing in our home. Thank you so much John for everything you do you have earned a customer for life with us!”
“She is trustworthy. She's not just trying to sell a house to make money. She cares about each client that she deals with to find just the right house for the right people. She's very patient.”
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 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.
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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 Chester Realtor® or real estate agent today.
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