Karen Willard
About Karen
Karen Willard brings over a decade of real estate expertise, a deep client-first philosophy, and a proactive, personalized approach to every client relationship. Licensed in both Illinois and Texas, Karen built her career in Austin before relocating to Chicago's Andersonville neighborhood—a community she chose for its warmth, inclusivity, and tree-lined, walkable charm.
Karen's professional foundation began as an Executive Assistant to high-level private equity executives in New York City, where she developed a reputation for anticipating needs, solving problems creatively, and delivering exceptional service. That same drive led her to a real estate development company, where she discovered a genuine passion for real estate. She earned her broker's license and has since built a reputation as a trusted advisor and dedicated advocate for her clients.
With a background in fashion, small business, and real estate development, Karen brings a unique eye for design, value, and opportunity. She combines that perspective with strong market knowledge, skilled negotiation, and a commitment to staying current on industry trends so her clients can make informed decisions with confidence. Karen holds a Bachelor's Degree in Apparel Design with a concentration in Business from The University of Texas at Austin and has pursued advanced real estate education through coursework toward the Luxury Home Marketing Specialist and Accredited Buyer's Representative designations.
Karen understands that buying or selling a home is far more than a transaction—it's both a significant financial decision and an important life milestone. Known for truly listening, communicating clearly, and creating a calm, low-stress experience, she guides clients with patience, honesty, and genuine care from the first conversation through closing. She never pressures clients before they're ready, but knows when decisive action is needed to protect their interests.
At the heart of Karen's business is a simple belief: every client deserves an advocate who treats their move as if it were her own. Whether helping a first-time buyer, marketing a luxury property, or assisting an experienced investor, Karen is committed to making the process feel manageable, rewarding, and centered around her clients' goals every step of the way.
The O'Connor Group’s Past Sales
The O'Connor Group’s Exclusive Real Estate Listings
-
7020 Keystone Avenue
$850,000
- 4 beds
- 3.1 baths
- Lincolnwood
- Detached Single
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2851 W Rascher Avenue
$1,700,000
- 6 beds
- 5.2 baths
- Budlong Woods
- Detached Single
-
6026 N Forest Glen Avenue
$1,000,000
- 4 beds
- 3.2 baths
- Sauganash
- Detached Single
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2536 Oak Avenue
$1,695,000
- 4 beds
- 4.1 baths
- Northbrook
- Detached Single
-
69 Nicholas Drive
$475,000
- 3 beds
- 2.1 baths
- Des Plaines
- Attached Single
-
7201 N Lincoln Avenue #403
$315,000
- 2 beds
- 2 baths
- Lincolnwood
- Attached Single
-
2551 W Arthur Avenue #2E
$375,000
- 3 beds
- 3 baths
- West Ridge
- Attached Single
-
6025 N Sacramento Avenue
$595,000
- 6 beds
- West Ridge
- Two to Four Units
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6128 N Francisco Avenue
$950,000
- 11 beds
- West Ridge
- Two to Four Units
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2656 W Logan Boulevard
$1,350,000
- 4 beds
- 3.1 baths
- Logan Square
- Detached Single
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5652 N Lockwood Avenue
$925,000
- 5 beds
- 3.1 baths
- Jefferson Park
- Detached Single