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Empathy, Experience and Excellence

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About Hileary Cleary

With over 20 years of experience in real estate, Hileary Cleary understands both the complexities and emotions that come with buying or selling a home. As a Seniors Real Estate Specialist® (SRES®), she is specially trained to meet the unique needs of mature clients making transitions in housing. Whether you're a first-time buyer, seasoned seller, or navigating a life change, Hileary is committed to making the process as smooth and stress-free as possible.


After falling in love with real estate more than two decades ago, Hileary has successfully built her career in some of the most competitive markets in the country, including Marin County, CA, the Greater Boston Area, and for the past 10+ years, the Chicagoland area. She brings a wealth of experience, market insight, and strategic negotiation skills to each transaction—consistently delivering desirable results for her clients.


Hileary's approach is client-centered, compassionate, and rooted in integrity. She takes great pride in walking alongside her clients during one of life’s biggest decisions, always advocating for their best interests.


When she’s not working, Hileary enjoys spending time with her husband Neil, their daughters Grace and Lily, and their Bernese Mountain dog, Teddi.

TESTIMONIALS

Highly recommend!
I had the pleasure of working with Hileary during both the purchase and sale of my property, and I couldn't be more impressed with her service. From the very first meeting, Hileary was incredibly attentive, taking the time to truly understand my needs and preferences. She was always responsive to my questions and concerns, no matter how small, and made sure I felt informed and supported throughout the entire process. What stood out the most was her ability to communicate clearly and effectively. She broke down complex information, guiding me through each step with ease, and made sure I understood every detail—whether it was about the buying process or the intricacies of selling my home. Her expertise in the market was evident, and she offered valuable insights that helped me make confident decisions. In both buying and selling, Hileary demonstrated a deep understanding of the local market, providing data and strategies that were spot-on. Thanks to her hard work and dedication, I was able to secure a great deal on both ends, and the entire experience was seamless and stress-free. I highly recommend Hileary to anyone looking for a knowledgeable, reliable, and personable real estate agent. She truly goes above and beyond!
Posted by Peggy T. (Seller) on 02 Apr 2025

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Downers Grove traces its name to Pierce Downer who settled the area on 150 acres in 1832. The arrival of the railroad in 1864 brought new opportunities and stimulated growth. The mid-1960s to the mid-1980s saw a boom period in which the population doubled. Abundant trees, parks and greenery earned Downers Grove the nickname, “Village of Trees.” Students attend elementary schools in District 58 or 69, and high school at Downers Grove North and Downers Grove South (District 99). Downers Grove has park sites totaling 500 acres. More than 500 programs are coordinated by the Park District and are devoted to sports, recreation, leisure and learning, including fully-developed programs for people with disabilities. The downtown area has a thriving shopping district, new construction condos, and entertainment venues that include the Tivoli Theater.

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Incorporated in 1926, Westmont has continued to grow dramatically as a result of booming industry in nearby communities. Most students attend school in District 201. High School students attend Westmont High School, Hinsdale Central, or Downers Grove High Schools. The Westmont Park District maintains 65 acres of land incorporating parks, playgrounds, playing fields and a community center.

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Planned in part by Frederick Olmsted, the designer of New York’s Central Park, Clarendon Hills is a “picture book small-town community.” Not quite two square miles in size, the Village projects a distinct charm and style. Residents and local organizations take an active role in maintaining the beauty of their community. District 181 houses two elementary schools. High school students generally attend Hinsdale Central High School in District 86. Four parks, two man-made lakes, a golf course, tennis courts, and several playgrounds are maintained within the village.

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Declared as "A Nice Place to Live", Darien is a city in DuPage County, about 20 miles southwest of Chicago's Loop. The city was named after a town in Connecticut. At the beginning of the twenty-first century, Darien was the youngest municipality in DuPage County. The city perfectly exemplifies the monstrous suburban development that occurred post-World War II. Darien is often associated with the Argonne National Laboratory, which is located nearby. In the 2010 census, the population of Darien was 22,086.

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Founded in 1873, historic Hinsdale is one of the Western Suburb’s most prestigious communities. Gently rolling lawns and quiet streets are bordered by oak, maple and elm trees. Downtown Hinsdale is a charming destination that offers fashionable boutiques and plentiful dining options that range from casual to upscale. In addition to several local plazas and the central business district offers charming shops and small businesses. Hinsdale Schools include Hinsdale Central and Hinsdale South High Schools, a middle school and five public elementary schools. The Village is home to parks that span over 120 acres and include tennis courts, a swimming pool and playgrounds. Cross-country skiing, swimming, archery and horseback riding are among the offerings.

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Early settlers to Lisle were attracted by the prime timber, agricultural land and plentiful water resources available. In 1850 Lisle Township was created, but the Village of Lisle was not incorporated until 1956. Today Lisle is situated at the crossroads of two major interstates in the heart of DuPage County’s High Tech Corridor. The town offers an ideal setting for residents, businesses and visitors alike. Lisle is served by two public school districts, Community Unit School District 202 and Naperville 203. Benedictine University is located within the Village and College of DuPage and North Central College is located nearby. The Park District maintains a community fitness center, an aquatic park and golf course in addition to the many park facilities found in the area.

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Founded by famed sportsman and captain of industry Paul Butler, Oak Brook has evolved into a thriving, sophisticated community. A modern commercial and retail base is complemented by abundant woodlands, ponds, streams, gently rolling hills and stately homes on tree-lined streets. Oakbrook Center has a growing reputation as Chicagoland’s premiere shopping site. Eight school districts serve the Oak Brook community. Most elementary students attend schools in District 53. Area high schools include Hinsdale Central (District 86), Downers Grove North (District 99) and York High School in Elmhurst (District 205). An avid polo player, Paul Butler was responsible for the polo field, which is home to the Butler National Polo Tournament. The village-owned Oak Brook Golf Club, sprawling 1800 acre Fullersburg Park, and the Oak Brook Sports Core with tennis and soccer facilities are popular recreational options for residents. The Park District coordinates numerous seasonal activities for the enjoyment of all age groups.

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