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.

𝟒 𝐦𝐨𝐧𝐭𝐡𝐬 𝐥𝐞𝐟𝐭 𝐢𝐧 𝐭𝐡𝐞 𝐲𝐞𝐚𝐫. 𝐀𝐧𝐝 𝐭𝐡𝐞𝐫𝐞 is 𝐚 𝐥𝐨𝐭 𝐨𝐟 𝐦𝐚𝐫𝐤𝐞𝐭 𝐥𝐞𝐟𝐭.⁣With $28M in closed + pending sales, we’re actively bringi...
09/03/2026

𝟒 𝐦𝐨𝐧𝐭𝐡𝐬 𝐥𝐞𝐟𝐭 𝐢𝐧 𝐭𝐡𝐞 𝐲𝐞𝐚𝐫. 𝐀𝐧𝐝 𝐭𝐡𝐞𝐫𝐞 is 𝐚 𝐥𝐨𝐭 𝐨𝐟 𝐦𝐚𝐫𝐤𝐞𝐭 𝐥𝐞𝐟𝐭.

With $28M in closed + pending sales, we’re actively bringing new homes to market and talking with clients about what the rest of this year and early next could look like.

One thing we know: in this age of scarcity, seasonality doesn’t have the same influence it once did. With pent-up demand, buyers are acting when the right home comes along.

The impact of scarcity in Lincoln Park is obvious, especially when compared to two years ago. A few highlights of latest numbers through August:

🔴 𝐇𝐨𝐦𝐞𝐬 𝐟𝐨𝐫 𝐒𝐚𝐥𝐞 ↓ 𝟑𝟗% | Lincoln Park condo + townhome inventory fell from 127 homes for sale in August 2024 to 78 in August 2026.
🟢 𝐌𝐞𝐝𝐢𝐚𝐧 𝐏𝐫𝐢𝐜𝐞 ↑ 𝟑𝟐% | 4+ bedroom median sold price has risen nearly $400K from $1.175M in 2024 to $1.55M this August.
🟢 𝐏𝐫𝐢𝐜𝐞/𝐒𝐅 ↑ 𝟑𝟎% | 4+ bedroom median PPSF rose from $393in 2024 to $510 this August.
🟢 𝐂𝐥𝐨𝐬𝐞𝐝 𝐒𝐚𝐥𝐞𝐬 ↑ 𝟏𝟒% | 3-bedroom sales increased from 312units to 355 units YoY.
🟢 𝐍𝐞𝐰 𝐂𝐨𝐧𝐬𝐭𝐫𝐮𝐜𝐭𝐢𝐨𝐧 𝐒𝐚𝐥𝐞𝐬 ↑ 𝟏𝟎𝟕% | 3-bedroom sales more than doubled from 14 in August 2024 to 29 this year.

A point worth making. Price acceleration has tempered the last 12 months. Numbers we are tracking closely. Some of our clients are selling now. Others are making improvements and engaging us with photography and other marketing preparation, so they are in a position to move when their timing is right.

The market isn’t waiting for spring. If a move is on your radar, let’s talk.

Dolly Parton lived extraordinarily for 80 years. She is the embodiment of the mythical American dream. A petite, poor co...
08/28/2026

Dolly Parton lived extraordinarily for 80 years. She is the embodiment of the mythical American dream. A petite, poor country girl from rural Tennessee who propelled herself to world-class stardom, globally admired. A boundless spirit of self-deprecating humor. Tireless work ethic bolstering born talent, destined for greatness. A faithful woman who loved her Lord and boldly proclaimed it. Married to her beloved husband for nearly six decades. A denter of the universe who impacted millions with her astonishing generosity and foresight. Humble, grace-filled and unapologetically ambitious. Contradictions that blended seamlessly into the fabric of who Dolly was. At her heart, she radiated goodness, joy and hopefulness. She achieved more success than one hundred gifted people could do in ten lifetimes. Yet, it is her character and genuineness that has impacted the world, joining people from all backgrounds and beliefs in honoring her.

𝐌𝐚𝐲 𝐰𝐞 𝐚𝐥𝐥 𝐬𝐭𝐫𝐢𝐯𝐞 𝐭𝐨 𝐛𝐞 𝐚 𝐥𝐢𝐭𝐭𝐥𝐞 𝐦𝐨𝐫𝐞 𝐥𝐢𝐤𝐞 𝐃𝐨𝐥𝐥𝐲 🩷

08/21/2026

Step into an unparalleled lifestyle of refined comfort.

Opportunity awaits.

The Orchard, Residence 103 hitting the market next week.

📍2350 N Orchard
2 bed 2.1 bath
Offered at $1,500,000

Reach out to us to learn more.

Some of the best relationships in our business are built over years of taking care of each other's clients.Maureen McCar...
08/20/2026

Some of the best relationships in our business are built over years of taking care of each other's clients.

Maureen McCarthy, has become one of our trusted agent partners in the Western suburbs and we’re grateful to be the same for her in the city.

Most recently, we worked with a first-time buyer she referred to us to find his West Loop condo. We connected the family of longtime clients with her for the purchase of an exceptional home in Clarendon Hills. And last year, when Maureen’s clients were ready to return to the city, we found them a beautiful single-family home in Lincoln Park.

Grateful for the business we’ve done together, but even more so for the friendship that has come with it.

With the Chicago Air & Water Show returning to the lakefront this weekend, we’re looking beyond the skyline to homes whe...
08/15/2026

With the Chicago Air & Water Show returning to the lakefront this weekend, we’re looking beyond the skyline to homes where aviation has a place in the story.

From a private helipad atop the Blue Ridge Mountains and an FAA-approved heliport on nearly 400 acres in Vermont to a Florida home with direct runway access and a historic Santa Barbara estate built by an aviation pioneer, each offers a different connection to flight. Some make getting away remarkably easy. Others were quite literally shaped by aviation.

Read more ➡️ https://bit.ly/4bPYnje

📍𝟓𝟖𝟏 𝐒𝐚𝐠𝐞𝐞 𝐖𝐨𝐨𝐝𝐬 | 𝐇𝐢𝐠𝐡𝐥𝐚𝐧𝐝𝐬, 𝐍𝐂
7 bedroom 7.4 bath
Offered at $32,000,000
Listed by Liz Harris and Jody Lovell with Sotheby's International Realty

📍𝟔𝟓𝟎 𝐅𝐫𝐚𝐧𝐜𝐢𝐬 | 𝐁𝐚𝐫𝐧𝐚𝐫𝐝, 𝐕𝐓
2 bed 4.3 bath
Offered at $29,000,000
Listed by Bravynia⁠

📍𝟏𝟓𝟖𝟓𝟎 𝐁𝐫𝐢𝐭𝐭𝐞𝐧 | 𝐏𝐚𝐥𝐦 𝐁𝐞𝐚𝐜𝐡 𝐂𝐨𝐮𝐧𝐭𝐲, 𝐅𝐋
5 bed 5.5 bath
Offered at $10,900,000
Listed by Rodolfo Maya with Illustrated Properties Real Estate

📍𝟑𝟎𝟑𝟎 𝐒𝐚𝐦𝐚𝐫𝐤𝐚𝐧𝐝 | 𝐒𝐚𝐧𝐭𝐚 𝐁𝐚𝐫𝐛𝐚𝐫𝐚, 𝐂𝐀
7 bed 5 bath
Offered at $6,475,000
Listed by Omid Khaki with Carolwood Estates.

The first seven months of 2026 have produced mixed results in Chicago’s $2M+ luxury market.⁣Citywide, median condo price...
08/13/2026

The first seven months of 2026 have produced mixed results in Chicago’s $2M+ luxury market.

Citywide, median condo prices are down slightly, while single-family homes are up 2 percent to $2.6M. Streeterville condo prices are up 10 percent, the Gold Coast’s niche luxury condo market is down nearly 25 percent and Lincoln Park condo prices are down 5 percent.

The constant across every neighborhood and property type is low inventory. Available homes are down 25 to 50 percent year-over-year in many areas. Still, buyers have shown they are unlikely to move on homes that don’t show clear value.

The Orchard continues to stand apart, with its last three closed and pending sales averaging north of $1,100 per square foot.

Our latest Luxury Market Report takes a closer look at Chicago, Lincoln Park, the Gold Coast and Streeterville ➡️ bit.ly/4fVbaDx

08/11/2026

There is a level of detail here you rarely find in a two-bedroom.

Designed in partnership with Soucie Horner, Residence 103 has the character and craftsmanship of a custom home. At its center, a bespoke Christopher Peacock kitchen pairs hand-painted cabinetry and walnut interiors with richly veined quartzite, setting the tone throughout.

Marble baths are finished with Waterworks fixtures and custom vanities. A limestone fireplace grounds the living room, with a heated, covered terrace overlooking the gardens of Lincoln Common, extending the space outdoors.

Thoughtfully scaled for full-time living or beautifully suited as an in-town.

2350 N Orchard, Residence 103
2 bed | 2.1 bath
Offered at $1,500,000

Private showings begin Wednesday, by appointment only. Reach out to us.

August 12 | 4–5:30pm

Some of our favorite opportunities are also our best-kept secrets. After two quiet pre-market sales at The Orchard, we’r...
08/07/2026

Some of our favorite opportunities are also our best-kept secrets.
 
After two quiet pre-market sales at The Orchard, we’re pleased to present one more.
 
A bespoke Christopher Peacock kitchen anchors this perfect two-bedroom home overlooking the landscaped gardens of Lincoln Common, while floor-to-ceiling windows open to a heated, covered terrace that blurs the line between indoors and out. Inside, every detail has been considered, from rich hickory flooring and marble-clad baths to custom millwork and timeless architectural details throughout.

📍2350 N Orchard, Residence 103
2 bed 2.1 bath
Offered at $1,500,000
 
Private previews begin next week. Reach out for early access.

Summer invites quiet reflection. Early mornings before the day unfolds. Evening walks that return us to what matters mos...
08/01/2026

Summer invites quiet reflection. Early mornings before the day unfolds. Evening walks that return us to what matters most. Lindsey Kamberos and I are whittling our business, pairing our strengths with the clients and opportunities we can serve most fully and generously.

Read more from our latest Cadey Curated ➡️ https://bit.ly/4fQWpjR

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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