Cadey O'Leary Collection

Cadey O'Leary Collection Luxury Broker at Christie’s International
Lincoln Park, New Construction, Upper Market

Cadey O’Leary has honed her knowledge and passion for quality new construction and design into a successful residential real estate business where she serves a range of clients from real estate developers to buyers and sellers of fine homes and condominiums on the city’s north side. With over ten years of upper-market real estate experience, extensive background as a successful entrepreneur and ma

rketing expert with a staunch commitment to excellence, Cadey has established herself as one of Chicago’s award-winning and top-producing agents. Appreciated for her candor, sales proficiency and personability, she values long-term relationships and is devoted to producing great outcomes for her clients who rely on her for all their real estate needs. With a keen understanding of what the luxury buyer values, Cadey has worked with several developers in helping design, market and sell new Single-Family Homes and condominiums, many of which have achieved new pricing thresholds in their markets. The hallmark of Cadey’s career to date has been the intensive ground-up developer collaboration and successful sell out of The Orchard Private Residences in Lincoln Park, surpassing previous pricing benchmarks by more than 30%. Cadey and her sales and marketing team worked alongside top talent in development, architectural and interior design in conceptualizing and producing a masterfully detailed, finely appointed boutique residential building that has become the new standard for luxury and most highly sought address on the city’s north side. Cadey’s unwavering dedication to offering unparalleled service for every client and her proficiency in communication and negotiation have placed her in the upper echelon of realtors in the city. She is among the top-10 selling agents in Lincoln Park with one of the highest average transaction sizes. Cadey has consistently been recognized as one of Chicago Agent Magazine’s “Who’s Who of Real Estate,” a Top Producer by the Chicago Association of Realtors® and among America’s top 1.5% of real estate brokers. Cadey enjoys connecting her clients, friends and colleagues, professionally and personally, and has co-founded several networking groups. She has cultivated personal relationships with brokers in other markets across the United States and has carved a particular focus and expertise in 30A along northwest Florida’s Emerald Coast, a long-favorite vacation spot for her family and her.

Over the past month, we have hosted client gatherings, attended charity events, enjoyed musical performances and a seren...
06/03/2026

Over the past month, we have hosted client gatherings, attended charity events, enjoyed musical performances and a serendipitous connection.

Last week, I had the pleasure of meeting the author of 𝑨 𝑳𝒊𝒕𝒕𝒍𝒆 𝑴𝒐𝒓𝒆 𝑺𝒐𝒄𝒊𝒂𝒍, a new book that explores the unexpected benefits of leaning in more and engaging with others. Nicholas Epley is a professor at Chicago Booth and researcher who integrates empirical data with anecdotal discoveries in this fascinating book. The black and white photo of the two of us was taken shortly after we discovered that my brother interviewed him the week prior on his podcast, John O'Leary - Live Inspired.

A wonderful, memorable moment that reinforces his book’s premise. Something I am working to expand upon.

This season has been defined by highly nuanced conditions across every segment of the market, resulting in $16 million i...
05/28/2026

This season has been defined by highly nuanced conditions across every segment of the market, resulting in $16 million in closed and pending sales this spring, with 40% of our transactions never hitting the MLS.

We have approached each client and property with a personally tailored strategy designed around their unique circumstances and timelines while pursuing winning outcomes.

These sales have been achieved through a thoughtful mix of Private Network listings, strategic MLS exposure, customized marketing plans, agent-to-agent outreach and priority access to off-market opportunities.

Relationships, expertise and results.

In today’s market of change and industry disruption, planning, knowledge and access are more important than ever. We are here to be of help and delighted to be a resource

Coming soon along the edge of Lincoln Park and Lakeview, this three-bedroom penthouse offers the best of North Side livi...
05/27/2026

Coming soon along the edge of Lincoln Park and Lakeview, this three-bedroom penthouse offers the best of North Side living with a wider floor plan, beautiful natural light and three private outdoor spaces.

Gracious interiors feature soaring ceilings, elegant millwork, custom-stained hardwood floors and a beautifully appointed chef’s kitchen, all designed for both easy everyday living and entertaining.

Above it all, a 1,700 sqft rooftop terrace delivers sweeping neighborhood and skyline views.

📍𝟐𝟗𝟏𝟖 𝐍 𝐒𝐡𝐞𝐟𝐟𝐢𝐞𝐥𝐝, 𝟒𝐒
3 bed | 2 bath
Offered at $950,000

𝐏𝐫𝐞-𝐦𝐚𝐫𝐤𝐞𝐭 𝐨𝐩𝐞𝐧 𝐡𝐨𝐮𝐬𝐞:
Friday | 4-6pm
Saturday | 12-1:30pm

DM for more information or to schedule a private tour.

05/22/2026

A beautifully appointed three-bedroom penthouse tucked along a coveted Lakeview block. Expansive wide floor plan. Private rooftop retreat perched above the trees and summer evenings waiting upstairs. SOON.

The market is highly nuanced right now.What we’re seeing in Lincoln Park is very different from what’s happening in the ...
05/20/2026

The market is highly nuanced right now.

What we’re seeing in Lincoln Park is very different from what’s happening in the South Loop, especially in the $1M+ condo market.

In Lincoln Park, inventory has tightened to just 1.3 months of supply and well-positioned homes are moving quickly.

Meanwhile, the South Loop luxury market is sitting closer to 4 months of supply with homes taking 60 days or longer to sell, often with price adjustments before doing so.

A reminder that broad market headlines only tell part of the story. Neighborhood, property type and buyer behavior matter more than ever.

Lately, many of our client conversations have extended beyond Chicago, working in tandem with our agent partners in Ohio...
05/13/2026

Lately, many of our client conversations have extended beyond Chicago, working in tandem with our agent partners in Ohio, Hinsdale and Lake Forest to help clients navigate timing, strategy and next steps across multiple markets.

What continues to stand out is how relationship-driven this business truly is. The ability to pick up the phone and collaborate across markets creates a far more seamless experience for clients navigating major transitions.

Many of today’s moves are far more nuanced than simply buying or selling a home. For some clients, that means aligning a sale with a purchase in another market. For others, it means creating flexibility before making a move.

This is where trusted relationships and thoughtful collaboration matter most.

What we are seeing now is extraordinary. Numbers that cast new perspective on Chicago’s inventory shortfall and market i...
05/02/2026

What we are seeing now is extraordinary. Numbers that cast new perspective on Chicago’s inventory shortfall and market impact, especially in preferred leafy neighborhoods where sellers of desirable homes and condos hold the cards and buyers the short straw.

Read more ⬇️

What we are seeing now is extraordinary. Numbers that cast new perspective on Chicago’s inventory shortfall and market impact, especially in preferred leafy neighborhoods where sellers of desirable homes and condos hold the cards and buyers the short straw.

Chicago remains one of the tightest inventory markets in the nation. A recent national report shows the city offered les...
04/28/2026

Chicago remains one of the tightest inventory markets in the nation. A recent national report shows the city offered less than one-third the number of homes for sale this March than it did in March 2019. But, that’s not the full story.

Closings are still happening. In Lincoln Park, closed sales are actually up over last year. Homes are going under contract before they fully hit the market. In a climate like this, strong reputations and relationships are vital to opening opportunities and ensuring winning outcomes.

The stone leads. Deep plum walls answer. Warm walnut, unlacquered brass. Design that lingers.Design 📷
04/24/2026

The stone leads. Deep plum walls answer. Warm walnut, unlacquered brass. Design that lingers.

Design
📷

Rituals shape how we show up and how we remember what matters. I was reminded of this last night attending my first atpr...
04/23/2026

Rituals shape how we show up and how we remember what matters. I was reminded of this last night attending my first atproperties Timeless Awards. The evening celebrates past and present honorees who have achieved a sales milestone.

I invite you to read more ➡️ bit.ly/3QCuye7

Address

548 W Webster Avenue
Chicago, IL
60614

Opening Hours

Monday 9am - 5pm
Tuesday 9am - 5pm
Wednesday 9am - 5pm
Thursday 9am - 5pm
Friday 9am - 5pm
Saturday 9am - 5pm
Sunday 9am - 5pm

Telephone

+17737104202

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