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Chester, SD real estate

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.

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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, SD real estate

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.

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“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!”

Isabella Bradstreet · Sioux City, IA

Photo of Hoffert Homes Group
Century 21 ProLink
“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.”

Mindy Dunne · Kingsley, IA

Photo of Jess Jager
Century 21 ProLink
“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!”

Emily Johnson ·

Photo of Greg Doohen Realty Group
Keller Williams of Sioux Falls
“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.”

Tyler Story ·

Photo of Amy Stockberger
Amy Stockberger Real Estate
“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!!”

lisaaymar12 ·

Photo of Tara Allen
Keller Williams Sioux Falls
“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.”

ck617613 ·

Photo of Henry Ulrich
Ascend Realty Inc
“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.”

wlevi4508 ·

Photo of Chelsea Link Real Estate
Berkshire Hathaway Midwest Realty
“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!”

computercowboy1982 ·

Photo of Casey Hatch
Keller Williams Realty Sioux Falls
“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.”

Russ Skovlund ·

Photo of Jessica Bergman
Keller Williams Sioux Falls
“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!”

Shaundonelan47 ·

Photo of Amy Hix
Hegg Realtors
“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!”

ella guppie292 ·

Photo of Julie Roth Real Estate
Real Broker LLC
“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.”

PamelaPowers5 ·

Photo of Delfs Real Estate Group
Keller Williams Siouxland & Okoboji
“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.”

talkiw ·

Photo of Luetke Team Real Estate
Keller Williams Realty Sioux Falls
“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!”

botermanbreanna ·

Photo of John Maurer
Vylla Home
“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.”

Tina Steppan ·

Photo of Di Dahl
Keller Williams Realty Sioux Falls

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 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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