Olive Well

Olive Well is a Chicagoland real estate group with Compass committed to strengthening the community beyond the real estate market.

Compass Real Estate is a licensed real estate broker and abides by federal, state, and local equal housing opportunities.

09/09/2026

While everyone else was enjoying summer, we spent it training for the fall market. Skills sharpened. Reflexes tested. Lockbox-opening speed at an all time high. Fall market starts now and we are ready to race. 🏁🍂🏡

04/14/2026

What worked a year or two ago doesn’t always work now.

The Chicagoland market is moving fast and the playbook is constantly changing.

We’re seeing:
• 10–15 offers on many homes
• 10–20% over asking becoming the norm
• Homes not always comping out
• Escalation clauses and “love letters” largely not allowed
• Cash buyers everywhere

So how do you actually compete?

It’s not just about price.

It’s about preparation and getting buyers ready both mentally and financially to act quickly and confidently. That often means working with a lender who can position you to waive a mortgage contingency (not for everyone but increasingly common in winning offers).

Terms matter and most offers include:
• Quick closes
• Free rent-backs
• As-is / no-request inspections

But honestly? One of the biggest advantages…

Relationships and collaboration.

Knowing the listing agent, understanding what the seller really wants, and positioning your offer the right way can make all the difference. Here at .well we often collaborate with other team members to hatch the perfect plan for a winning strategy.

That said, not every home is flying. Some are sitting, and there are still opportunities to find great value. It’s a tale of two markets and knowing the difference is everything.

In this market, strategy is everything.

Make sure you’re working with someone who knows how to navigate it.

02/24/2026

Our broker .gwin updated her bathroom for $2,220 — keeping the travertine tile, upgrading strategically, and creating something that now feels custom and layered.

From a real estate perspective, that matters.

When buyers walk into a bathroom, they don’t calculate tile costs. They react emotionally. And this one now feels finished.

Full breakdown is on the blog!

Swipe 👉 to see the before.

12/14/2025

Join us this Wednesday, 10/17, at 10 AM at in Lake Forest as we pack meal kits for foster and homeless children in our community. $50 contribution recommended.

Comment Give Back for the RSVP link. We hope to see you there!

11/04/2025

Meet the Team Tuesday: .oliff 💕
Chicago lover, proud fighting Illini, and Lombard native — Dana’s been helping clients buy and sell homes for a decade, and she still believes Chicago is the best city in the world.

Known for her positive energy and sharp organization, Dana makes even the most stressful moments in real estate feel manageable. She’s been featured in Chicago Agent Magazine, Who’s Who in Chicagoland Real Estate, and The American Dream TV.

At home, Dana’s world revolves around her husband, their daughter Olivia, and their labradoodle Harvey. She is usually cooking something new, exploring local markets, or relaxing on the front porch with a good book (and glass of w**e). Health and wellness are her passions, but grocery shopping might just be her favorite form of therapy. 🛒🥦☀️

10/08/2025

Meet the team Tuesday with ! Real estate expert, hands-on dad, renovation pro, and travel enthusiast always ready for the next adventure. A Lake Forest native now living in Highland Park with his wife and business partner, Lauren Mitrick Wood, Charlie is a proud girl dad to fearless two-year-old Blair and recently welcomed his son, Weston, into the world.

He and Lauren are currently restoring their 115-year-old Howard Van Doren Shaw home — a project that’s as beautiful as it is never-ending. When he’s not on a job site or showing homes, you’ll find Charlie recharging on the ski slopes, cheering for Liverpool FC, rooting for any Chicago sports team, or catching live music wherever he can.

Whether exploring a new city, walking their Vizsla, Cooper, or guiding clients through the market, Charlie brings calm energy, creativity, and deep Chicago + North Shore expertise to everything he does.

Fun fact: ask him about his teaching adventures in China — or the time he walked the runway in Milan for Louis Vuitton back in high school!

Thx for the pic 📸

09/24/2025

Meet the Team Tuesday: Patrick Shipp! is Michigan-born, Chicago-obsessed, and your go-to guy for all things real estate. He made the leap from corporate life to helping people find home sweet home in 2012, and he’s been rocking the Chicago market ever since.

With over 10 years of experience, Patrick brings savvy negotiation skills, deep neighborhood knowledge, and a heart-led approach to every deal. When he’s not realestating, he’s catching up with family in Michigan, sharing his Eagle Scout camping skills, or indulging in his two favorites: Hendrick’s gin and chicky tenders. His go to spot for each? for a dirty Hendricks martini. Mmmmm. And in Wicker Park for chicken tendies - double mmmmm.

Patrick proudly serves on the Young Professionals Network, and OUT at Compass—all while repping the Olive Well Team with the utmost energy and heart. ❤️💕

09/16/2025

Meet the Team Tuesday: ! Architect. Developer. Realtor. Entrepreneur. Julie isn’t your average agent—she brings a designer’s eye and a developer’s mindset to every real estate journey. With a Master’s in Architecture from IIT and a background in design and construction, she knows homes from the inside out. Born in Barrington and well-versed in neighborhoods across Chicagoland, Julie connects deeply with her clients and helps them envision what’s possible—whether buying, renovating, or building from scratch. She loves hiking solo in England, tending to her massive garden, or planning her next off-the-map family adventure. A proud DePaul parent, fluent in German and always renovating her home with her architect husband, she’s smart, she’s creative, and she’s genuine, that’s Julie!

08/29/2025

This summer, several of our team members hit the road and landed in Denver for a company-wide Compass retreat. We had the chance to connect with incredible agents from across the country—swapping stories, sharing strategies, and building relationships that make us all stronger. A big thank-you to the .realestate for kicking things off with their networking event!

📸 Pictured here are some of our Olive Well agents alongside partners from coast to coast at the East Coast Network’s welcome party. These connections mean that when life takes you beyond Chicago, we can connect you with trusted professionals who will take great care of you—wherever your next chapter leads.

08/26/2025

Meet the team Tuesday with - She is a South Florida native turned Chicago real estate expert, who is now also licensed in Nashville, managing multiple markets with over a decade of experience. She’s passionate about helping clients feel truly at home—no matter the city. A proud wife, boy mom to Walker, and dog mom to Theo (their lovable Frenchton), Laura brings a warm, driven energy and a designer’s eye to every transaction. She’s half Italian, has two older brothers, and swears by ketchup on her mac and cheese (really!?)

Outside of real estate, you’ll find her decorating for fun, planning her next getaway, hunting down the best coffee shops, or soaking in the magic of city life. She was recently a host on and you can check out her home tour on our website at OliveWell.com

Address

1643 N. Milwaukee Avenue
Chicago, IL
60647

Website

http://www.olivewell.com/

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