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Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for December 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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“This is the second time that Kim 🗝️🔑 assisted me in a real estate transaction. I recommend Kim for her professionalism, promt response times and hard work! Kudos to her photographer. My buyer told me that mine was one of the only homes that was represented well with photos.”
“She was very helpful especially to a first time home buyer. Whatever questions I had about the property she would answer it or get the answer from the listing agent. Was always on time for showings. Would definitely recommend her especially for first time buyers”
“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.”
“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!”
“Juan helped us immensely in buying our first home and answered every question we had. Would 100% recommend.”
“Antonio was always available for questions and always prompt in his replies. An ecellent experience.”
“I had an amazing experience working with Erick when purchasing my new home. From the very beginning, he took the time to understand exactly what I was looking for and offered valuable insights into the housing market. Erick was incredibly knowledgeable, patient, and responsive, answering all my questions and guiding me through every step of the process. The process of finding the perfect home can be overwhelming, but Erick made it seamless. He was always available to schedule viewings at my convenience, and when we found the right place, he worked tirelessly to ensure my offer was competitive and that all the paperwork was handled efficiently. Thanks to Erick, I now own a home that I absolutely love. I highly recommend him to anyone looking for a dedicated and professional real estate agent.”
“Marc was a crucial part of our home buying process and we are grateful we chose him. He was there every single step of the way from start to finish and went above our expections in many ways. He is great in his craft and we would use him again without a doubt.”
“Sharie did excellent job. Always accessible on time. Extremely approachable”
“Larry is by far the most AMAZING Realtor. He was always very responsive to my calls, texts, request, etc. We built up such a great relationship through this crazy process, that even after we closed on our new home, he reached out to check on us. He is always looking to get the best deal for his clients. He is like family now to us and will always have his own seat next to the firepit in our backyard. I would DEFINETLY recommend Larry to anyone and everyone looking to buy or sell. AMAZING.. Can't say enough Great things about Larry.”
“Easily one of the best realtors, he was extremely friendly didn’t rush us for houses tours. He also showed my family and me plenty of houses on the market for months.”
Information and statistics on the latest trends in the Sleepy Hollow real estate market, updated for December 2025. *
The typical home value in Sleepy Hollow is projected to be $278,000 for the month of November. October’s finalized data reported the typical value of a home in the neighborhood to be $278,000—down 24.04% over the previous 12 months. For comparison, city-level data pegged home values at $380,000 in Chicago for the most recent reporting period. That number is expected to float around $385,000 in November.
Sleepy Hollow had 1 active listings in October, including 1 new listings. Overall, active listings were down 50.0% from the previous month.
The median listing price for homes in Sleepy Hollow fell 0.0% from September to October, bringing the current median listing price to $480,000. Based on projected data for November, listing prices may continue to fall.
The number of days that homes have been on the market prior to going under contract has been fairly steady year-over-year. In October 2025, the median time for a listed property to go pending was 64 days, compared to 64 days in October 2024. In recent months the median number of days from listed to pending appears to be steady. That trend is predicted to have carried through to this November.
Sleepy Hollow offers residents a welcoming, walkable community with green spaces, convenient local shops and services, and family-friendly amenities that foster a strong, close-knit neighborhood feel.
Sleepy Hollow is a quiet pocket on the city’s southwest side where winding residential streets, mature trees, and mid-century homes create a calm, close-knit rhythm. Steps from Beverly and Morgan Park, it offers the best of neighborhood living with quick access to wider Chicago energy. Residents value the extra elbow room—generous yards, alley-access garages, and a front-porch culture that makes block parties and holiday displays feel like community traditions.
Daily life here is easygoing yet well connected. Local playgrounds, ballfields, and fitness programs run by the Chicago Park District keep weekends active. Commuters appreciate the convenience of the Metra Rock Island service from nearby Beverly/Morgan Park stations for a swift ride to the Loop, while the Chicago Transit Authority links the neighborhood to the rest of the city by bus and rail.
Families are drawn by strong education options through Chicago Public Schools, including neighborhood schools, magnets, and selective-enrollment programs. After-school enrichment and story times at the Chicago Public Library add to the family-friendly rhythm, and locally owned cafés and casual eateries anchor everyday conveniences along nearby commercial corridors.
If you’re looking for a serene residential base with solid schools, reliable transit, and a genuine neighborhood feel, Sleepy Hollow delivers the right balance of calm and city access. Whether you’re buying or selling, Agent Pronto can connect you with a local expert who understands Sleepy Hollow block by block.
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 Sleepy Hollow. 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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