Philip Winston
About Philip
With a deep-rooted connection to Chicago spanning nearly three decades, Philip Winston brings a valuable blend of communication expertise, negotiation skills, and a client-focused approach to the real estate industry. Having spent over 15 years as a professional actor and eight years as a college professor specializing in communications and public speaking, Philip has honed his ability to connect with people, understand their needs, and guide them toward their goals with clarity and confidence.
Growing up in a family immersed in real estate—his father a land surveyor and his mother a real estate professional—Philip developed an early passion for the industry. His first experiences in real estate involved working alongside his parents, learning the intricacies of land assessment and property preparation. This foundation, combined with his extensive background in customer service, has equipped him with the ability to anticipate client needs and navigate transactions with professionalism and ease.
Philip’s expertise extends beyond buying and selling properties; his strength lies in fostering meaningful relationships and ensuring clients feel informed and empowered throughout every step of the process. His strong interpersonal skills, innovative thinking, and unwavering tenacity set him apart in a competitive market. Whether negotiating a deal, crafting strategic marketing plans, or providing clear and consistent communication, Philip is dedicated to delivering exceptional service tailored to each client’s unique aspirations.
A passionate Chicagoan, Philip loves celebrating the city’s vibrant culture, stunning architecture, and diverse neighborhoods. His deep knowledge of the local restaurant and theatre scene further reflects his enthusiasm for all that Chicago has to offer. When he’s not working with clients, you’ll find him cooking, gardening, running, or spending time with his family.
Guided by the philosophy of “recommit”—a lesson learned from his years in theatre—Philip approaches challenges with perseverance and a steadfast commitment to his clients’ success. Whether buying, selling, or investing in Chicago real estate, Philip Winston is a trusted partner dedicated to making each transaction as seamless and rewarding as possible.
For anyone looking for a place to live, I would highly recommend Philip Winston. Philip communicates clearly and brings a lot of knowledge about the area. He is highly responsive and puts his clients first! Overall, Philip was very considerate of and attentive to my needs. Philip was a pleasure to work with and helped me to find a perfect place for me!
The O'Connor Group’s Past Sales
The O'Connor Group’s Exclusive Real Estate Listings
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8940 Lamon Avenue
$0
- 7 beds
- 3.2 baths
- Skokie
- Two to Four Units
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2214 W Oakdale Avenue
$2,250,000
- 6 beds
- 4.1 baths
- North Center
- Detached Single
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2851 W Rascher Avenue
$2,500,000
- 6 beds
- 5.2 baths
- Budlong Woods
- Detached Single
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1932 W Crystal Street 1
$699,900
- 3 beds
- 2.1 baths
- Wicker Park
- Attached Single
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2225 W Carmen Avenue
$1,699,000
- 5 beds
- 3.1 baths
- Ravenswood
- Detached Single
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3037 N Lincoln Avenue 204
$1,115,000
- 3 beds
- 2.1 baths
- Lakeview
- Attached Single
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3836 N Bell Avenue
$1,000,000
- 6 beds
- 2 baths
- St Bens
- Two to Four Units
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6144 N Francisco Avenue
$1,125,000
- West Ridge
- Multi Family 5+
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5706 N Mozart Street
$725,000
- 5 beds
- 2.1 baths
- West Ridge
- Detached Single
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4235 N Kedzie Avenue 3B
$325,000
- 2 beds
- 2 baths
- Irving Park
- Attached Single
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6316 N Magnolia Avenue
$1,100,000
- 5 beds
- 4.1 baths
- Edgewater
- Detached Single
See what people are saying about Philip
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Lorena D Working with Philip to purchase our first home in Chicago was an absolute privilege. As first-time buyers in the Chicago area, during the holiday season and in a 2026 market that requires both speed and precision, we were initially overwhelmed, but Philip’s local market expertise and guidance made the entire journey seamless. I myself am a fellow realtor of 26 years, and I will forever be a client of Philip!!
From our first meeting, his excellent communication stood out; he was always responsive, ensuring we were updated at every stage of the transaction. Philip didn’t just show us listings; he provided invaluable details on Chicago's unique neighborhoods and helped us navigate the complexities of condo associations and local regulations.
Thanks to his sharp eye for detail and proactive approach, he found us a beautiful condo that checked every box on our wishlist. Throughout the closing process, he was a steady hand, providing the specific guidance we needed to feel confident in our investment. He has become more than our local agent in the Chicago area, he will forever be family. He treated us with such kindness, genuine concern and honesty.
If you are looking for a professional, knowledgeable, and dedicated realtor in Chicago, we cannot recommend Philip highly enough!
Thank you for making our daughter’s dream come true!
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Josie M and Rob S Without Philip's hard work and dedication, we don't think we would have landed our current home. As first time homebuyers, we were nervous about the process and didn't know where to start, but thankfully Philip was there! Philip was on top of everything during the entire process, which helped take the stress off our shoulder and eased our minds. He took time to build a relationship with us that went deeper than surface level- we even sent him a picture of a dish we made with spices he gifted us as a housewarming gift. He really took the time to get to know us. He is very knowledgeable of his craft and supported us throughout the entire process. After each showing, Philip dedicated time to listen to our thoughts, which he then burned to memory and applied to future showings. We are so thankful to Philip for helping us find a place we are happy to call home.
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Freddy V. For anyone looking for a place to live, I would highly recommend Philip Winston. Philip communicates clearly and brings a lot of knowledge about the area. He is highly responsive and puts his clients first! Overall, Philip was very considerate of and attentive to my needs. Philip was a pleasure to work with and helped me to find a perfect place for me!
