“Working with Tracy to buy our home was a great experience and she was always available and communicative even as we navigated some difficult parts of the negotiation with the seller. She was personally at every visit and even at the inspection and closing, going way above and beyond my expectations and previous experiences with buying agents. Thanks to her we found a home for our family and while we don't plan to buy in the near future I'd be happy to work with her again and again. Thanks Tracy!”
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Compare top Pill Hill / Calument Heights real estate agents.
Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for June 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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Pill Hill / Calument Heights real estate Market Report.
Information and statistics on the latest trends in the Pill Hill / Calument Heights real estate market. *
Latest Rolling 3-Month Snapshot
Mar 1, 2026 - May 31, 2026
Quarterly Pricing Trends for Pill Hill / Calument Heights
Rolling three-month data ending on quarter boundaries when available.
Quarterly Pricing Trends for Pill Hill / Calument Heights
Rolling three-month data ending on quarter boundaries when available.
Quarterly Pricing Trends for Pill Hill / Calument Heights
Rolling three-month data ending on quarter boundaries when available.
Quarterly Inventory and Sales Activity for Pill Hill / Calument Heights
Rolling three-month supply and activity totals for the selected period.
Quarterly Inventory and Sales Activity for Pill Hill / Calument Heights
Rolling three-month supply and activity totals for the selected period.
Quarterly Inventory and Sales Activity for Pill Hill / Calument Heights
Rolling three-month supply and activity totals for the selected period.
Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Mar 2026 - May 2026).
Pill Hill / Calument Heights is currently tilted toward sellers, with the market gauge reading a seller’s market and only about three months of supply available. Homes here are also priced well below the broader Chicago market, with a typical home value around the mid-$190,000s compared with Chicago’s median closer to the low $400,000s.
Prices in this rolling three-month view are notably softer than a year ago, with the typical home value down more than 20% year over year. At the same time, the share of homes selling above list has fallen to roughly one in five, down from much higher levels seen in late 2025, suggesting buyers have more room to negotiate even in a seller-leaning environment.
On the activity side, homes sold have inched up slightly from a year earlier while active listings are down nearly 20%, reflecting fewer options but steady demand. New listings have dropped by more than 20% year over year, yet the average sale-to-list ratio is still above 97%, showing that realistic pricing is getting deals done for both sides. Buyers and sellers who want to navigate these shifting dynamics can use Agent Pronto to connect with a local real estate agent who understands this neighborhood’s trends.
Learn more about what Pill Hill / Calument Heights has to offer.
Pill Hill / Calument Heights offers residents a welcoming mix of green spaces, local dining, practical transit options, and a close-knit community that makes everyday life convenient and engaging.
Pill Hill / Calument Heights in Chicago combines residential calm with practical connectivity, appealing to long‑time residents and newcomers alike. Located on the Southeast Side, the neighborhood offers quick access to Lake Shore Drive, I‑94, and Metra Electric service from nearby South Chicago, making commutes to downtown and neighboring areas straightforward.
Tree‑lined streets feature primarily single‑family homes and bungalows, with larger lots than many North Side neighborhoods. Everyday needs are close at hand, with grocery options along Stony Island Avenue and nearby retail in Chatham and Avalon Park. Residents can enjoy outdoor space at Rosenblum Park and larger green areas like Calumet Park along the lakefront. The Whitney M. Young Jr. Branch Library and local schools such as Gwendolyn Brooks College Preparatory Academy add educational and community resources.
Dining and everyday services extend into neighboring South Shore and Pullman, where historic attractions and additional shopping broaden local options. Proximity to the expanding Chicago Park District network and Southeast Side cultural institutions supports an active, convenient lifestyle.
Whether you are buying your first home in Pill Hill / Calument Heights, moving within the neighborhood, or preparing to sell, an agent who understands local pricing, school boundaries, and commute patterns can significantly reduce stress. Agent Pronto connects both buyers and sellers with the right local real estate professional to navigate the process with confidence.
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“Steven was very helpful, knowledgeable, passionate, and most importantly he met all of my needs! I will definitely use him for all of my future home purchases in the near future. Thanks again Steven, he's definitely a ROCK STAR! I can't wait to work with him in the near future. Betty Ng”
“Meldina is an expert in the local market and an exceptional negotiator. Her professionalism, communication, and dedication exceeded our expectations. We highly recommend her!”
“Mike was very responsive from start to finish. Our home sale played out exactly how Mike told us it would. We had multiple offers over asking the first weekend. We were moving out of state and a smooth and quick sale is what we were hoping for and Mike made that happen. We would highly recommend Mike to anyone looking to sell their property in the Southwest Suburbs.”
“Kim has sold two properties for me this year, and in both transactions she did a fantastic job. She was always responsive, communicated clearly throughout the process, and took the time to answer every question I had. Her professionalism, market knowledge, and attention to detail made each sale go smoothly. I would highly recommend Kim and her team to anyone looking to buy or sell a home in the area. Based on my experiences, I personally would not hire any other agent to sell a house.”
“Barb was 1/20 realtors who was willing to work with me in the beginning over 9 years ago. This is when I first purchased my home. I was cheap buyer. It went without saying I was going to be using her for the sale of the home 9 years later. She handled the hurdles flawlessly and talked me through and coached me the entire way. To say I appreciate her is an understatement. I sold my home after we relocated it of state and she coordinated every logistic of that sale on my behalf to he best of her ability. I recommend her without fail and would point every person in her direction that has a need for a solid realtor.”
“Kathy fought a lot of uphill battles for us and despite hurdles at every turn (with prospective buyer) she pushed on and was able to secure our sale. I can't thank her enough for the amount of work she put in.”
“It was a joy to work with Kathryn she was able to answer every question I had, her knowledge goes a long way and I will definitely recommend her to friends and family.”
“Brittany is an AMAZING realtor and I don't say that lightly. She goes above and beyond to make sure that we are getting everything that we asked for and more. If you are looking for a realtor that goes out of her way to make sure her clients needs are met, you have found your realtor! I could not put into words how happy I am!”
“Working with Emir is always a pleasure. He was very helpful in coordinating work on our house for sale, working with vendors and providing valuable feedback on neccesary work vs. potential work items unlikely to generate return. We closed sale of house 3 weeks from time of first listing. I'd worked with Emir before and hope to do so again in the future.”
“Becki from Laura Topp’s team was incredible in helping me purchase my first property, a brick 2-flat in Chicago’s highly competitive north and west side market. Inventory was extremely limited and we toured at least 20 properties throughout the process. Becki was consistently accommodating with her time, prepared detailed reports for every showing and approached each opportunity with a thoughtful strategy. She genuinely treated the search as if she were buying the property for herself. When we finally found the right building, Becki skillfully negotiated with the listing agent and played a major role in getting the deal done while still protecting my interests and keeping the transaction together. The listing agent even praised her professionalism and credited her with helping secure the deal. Throughout closing, she remained diligent, communicative and focused on making sure I understood every step of the process and felt protected as a buyer. I cannot recommend Becki and Laura Topp”
“Melissa Young was incredibly attentive and knowledgeable which was critical for me as a first-time home buyer. She helped me win my very first bid with a strong offer and guided me through challenges with the appraisal process. She sets the bar high and I am so happy with my beautiful first home in Chicago!”
“Thanks for your help in purchasing our first home!”
“Great experience! Very attentive, honest, and dedicated. Professional, efficient, and easy to work with. Highly recommended!”
“Our house could be considered high end property in the neighborhood. Cinny worked hard to get it under the contract in a week and sold our house a little over a month. We are happy about the result. During the process, there were ups and downs which made us nervious. Cinny listened to our concerns and gave us professional advice.”
“Shawn is a perfect example of everything a new homeowner could want in a realtor. He's patient, informative and passionate about helping you find the right home. Shawn goes the extra mile in preparing detailed documents on every listing you visit and has a vast knowledge of property pros and cons. You also know you'll get a honest and trustworthy professional at your side when you work with him. I can't recommend Shawn enough!”
“Would use Lizette again, very easy to work with & very professional. Would recommend here 100% to Friends.”
“Renee O'Brien was very understanding, helpful, and kind .... knowledgable in the house situation and problem solving to move the sale along swiftly...”
“Before using Jeffry as my agent, I had looked at several homes with 3 other agents for almost a year. Within 2 months of working with Jeffry, we found the home that I had been looking for and was the perfect fit.”
“John Campobasso was great to work with in selling our unit. He was professional, knowledgeable, and guided us through every step of the process. We really appreciated how upfront and straightforward he was. He always gave us honest feedback and clear expectations. He made the whole experience feel smooth and much less stressful than we anticipated. We’re so glad we worked with him and would definitely recommend his services to anyone looking to buy or sell.”
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 Pill Hill / Calument Heights. 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 Pill Hill / Calument Heights Realtor® or real estate agent today.
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