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“Working with Victoria Holmes was such a wonderful experience from start to finish. She made the whole process feel effortless, and her supporting staff was just as incredible—so kind, attentive, and genuinely invested in helping us. We keep pinching ourselves because this home is absolute perfection for our family. We’re beyond grateful to Victoria and her team for making this dream a reality.”
“Kim is the best. I shared with her that I had to sell my family members home and that I had 0 experience with realty or selling a home. She made everything so easy. The sale happened within days and I had no issues. She was there to help in a stressful time for me. I highly recommend.”
“Shawn came highly recommend and did not disappoint. He has been on the ball and on my side from begining to end. His local knowledge was invaluable as a buyer moving from out of state and his follow through with vetted vendors for after the purchase smoothed the transition. Shawn Jones is a man of his word and goes above and beyond.”
“Donna negotiated four houses for us and got us under contract for under asking and got the seller to fix many of the large issues. Will be a returning customer.”
“Miguel was amazing 10/10 definitely recommend! He is very knowledgeable and super attentive, he really made this first time home buying process very smooth and the best of all is that he was very understanding.”
“Kathryn Hoffman was recommended by a woman in our church book club. Kathryn lived up to the praises and compliments given by this person. She was professional and knowledgeable about every aspect of the home search and purchase process. Kathryn did her best to work around my schedule and was available for showings when necessary. Ms. Hoffman clearly understands the housing market and the many aspects and attributes of the communities in the Chicago suburbs. She was able to connect me with other experienced and respected professionals, as necessary during the purchase process (attorney, home inspector, etc). I would highly recommend Kathryn Hoffman as a realtor/agent.”
“Barb provided exceptional service throughout my home-buying experience. She demonstrated professionalism, clear communication, and a genuine commitment to ensuring a smooth process from start to finish. I am grateful for her guidance and highly recommend her to anyone seeking a knowledgeable and reliable real estate agent.”
“Cinny helped us sell and buy a condo at the same time and the whole experience was so smooth. From helping us list our place, going to showings with us, and answering all our concerns, I don’t know how she did it all but she was there for us. We were able to do both the selling and buying within 3 months which still amazes me how quick and easy she made this process. She was proactive in finding places and booking showings that work around our schedule. And what I really love is how well she understood what my partner and I were looking for in a home. We ended up buying the place she had suggested for us. Originally this place was not on our radar but she highly recommended us to check it out and we’re so glad we did. We’re so happy with new home and this could not have been done without Cinny!”
“John was a great Realtor many years of experience definitely knows his market. John is definitely one of the people that will get to know his sellers his clients and every time that I had any issues John always answered within an hour sometimes within minutes the funny thing is is that one day out of the blue John contacted me Wanting to know if I wanted to sell my house and I said you know I've been thinking about it cause I had a tenant in there and I have some severe medical problems and John waited and waited and waited through all the endless phone calls and follow ups. He ended up getting my business because he was patient. He waited and it took over a year of us working together to get my house on the market and it's sold in two weeks. I cannot say enough good things about John, but I do thank him for his patience and his understanding with my personal issue and I promised if he didn't give up on me, he would get the business and he got it!”
“Brittany was the best agent anyone can ask for always very informative and guided me threw all the steps as a first time home buyer I can not say enough about how amazing/professional she was as a first time home buyer i would recommend her to anyone who really wants someone to be in your corner on getting the perfect house that best suits your interest i found a home perfect for my family and it was all thanks to Brittany absolutely amazing 10/10”
“Nancy Silwa is an experienced realtor who knows her profession. She knows, and in fact lives in the area, where I was selling my house. This was a bonus as she really had a handle on the market. She walked with me every step of the way so that I understood the process. I was selling a home I had lived in for 43 years. Nancy understood the emotional impact of this decision and gently helped me stay focused on the task at hand: sell the house. She found the perfect buyers. A young couple who will make my house their home. Knowing this made selling my home a little easier. I would and indeed have recommended Nancy to others. She is simply THE BEST!”
“I can’t recommend Emir highly enough! From start to finish, he was professional, knowledgeable, and incredibly responsive. He truly had my best interests at heart and made the entire buying process smooth and stress-free. His attention to detail and dedication went above and beyond. If you’re looking for someone who knows the market and actually cares about their clients, Emir is the one!”
“Exceptional professional and person. Meldina was so kind and supportive through the entire process of buying my first commercial purchase.”
“Laura Topp was recommended by a trusted friend, a friend whom I will trust even more after this experience. Laura is extremely knowledgeable, personable and very well connected in the real estate market. Laura and her team (including Becki, also very involved in my sale and purchase) went over and above to insure my then-current home was sold in a timely manner (it was a matter of days, in fact) and for the best possible price! As for my purchase, Laura connected me with not only public but also private listings, and I also found/ contracted for my new dream home within days. In addition to her knowledge, expertise and connections, Laura is also one of the kindest people have ever met; she made me feel valued and supported throughout this entire process. I would recommend Laura and her team in a heartbeat (I already have) and although I was not previously aware of BHHS, this company also has high ratings in my book because of Laura and Becki.”
“Working with Tracy Anderson gave us a leg up. She is very knowledgeable of the market. She was very patient with my father. She staged the Home well using his furniture which made it look great. Her negotiating skills helped us through some potentially tricky issues and let us net the most possible. I would recommend her 100%!”
“Jeff held the fort down while I was away for 3 weeks, during which time we had repairs done and had the house professionally cleaned. He was totally trustworthy. I cannot think of a better real estate agent.”
“Heather was a dream to work with in our home buying journey. She was very responsive, patient, and understanding of all of our needs when it came to what we wanted in a home. Her great personality and good sense of humor made her a pleasure to be around. Her knowledge and recommendations made our process smooth and painless. My wife and I highly recommend considering Heather all of your real estate needs.”
“My Wife and I were first time homebuyers in a very difficult market. Renee guided us through the process and answered any and all questions we had. We're extremely pleased with the end result and would happily work with her again in the future.”
“Antonio was always available for questions and always prompt in his replies. An ecellent experience.”
“We live in Florida and were wanting a second home in the Plainfield, Illinois area. We were not seeing too many places that were available. She showed us a few places in January online but they didn't work out for us. Since she knew what we were looking for, a condo went on the market that she thought we would be interested in. We happened to be in the Chicago area in March so we investigated the condo and sure enough we liked it and made an offer, and subsequently purchased. We were lucky that she remembered what we were looking for, and are so grateful to her for that, We also appreciated that she was not high pressure and that would have been an immediate turnoff for us. She was very helpful throughout the whole process and we would recommend her highly. Thanks again Kathy!”
Information and statistics on the latest trends in the Winchester real estate market, updated for September 2025. *
Winchester offers residents a warm, close-knit community with excellent schools, plentiful parks, and a welcoming blend of small-town charm and convenient local amenities.
Winchester rewards residents with small-town ease and surprising access to opportunity. As the seat of Scott County, its historic courthouse square anchors locally owned shops and eateries, while US-67 and Illinois 106 make commutes to Jacksonville and Springfield straightforward. Weekends often start outdoors: anglers, hikers, and families head to Siloam Springs State Park for trails, picnic areas, and a scenic lake managed by the Illinois Department of Natural Resources, and hunters and wildlife watchers find expansive prairie and timber at Jim Edgar Panther Creek State Fish and Wildlife Area.
Families appreciate educational continuity through Winchester CUSD 1, which offers K–12 academics, arts, and athletics with a community-centered feel. Nearby higher education deepens the talent pipeline and enrichment options, from the liberal arts tradition at Illinois College to workforce and transfer programs at Lincoln Land Community College’s regional offerings. Healthcare needs are well covered, with specialty care and a modern emergency department a short drive away at Jacksonville Memorial Hospital within the Memorial Health system.
Housing spans classic Victorians near the square to newer builds at the edge of town, and daily life revolves around school events, youth sports, and neighbor-to-neighbor support that makes newcomers feel at home quickly. Whether you’re buying your first place or preparing to sell, Agent Pronto can connect you with a top local agent who knows Winchester’s market inside and out.
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 Winchester. 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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