Olive Well

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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.

10/19/2026

You can take the girl out of the East Coast… ❤️

Tori grew up outside of Boston, but Chicago is the place she chose to put down roots—and over the years, she’s made it very much her own.

She loves a house with potential, a garden to grow, a neighborhood that feels like home, and—like the rest of us—somehow always has one more project that definitely “needs” to be done. 😂

For Tori, home is about so much more than the house itself. It’s the community, the people, and the life you build around it.

Next up in our Get to Know Our Brokers series, meet Tori and see how she homes.

Where All Live Well.

10/08/2026

Well, this is awkward. 😂 It’s my turn.

As the person who is usually behind this account—and the one making everyone else do these videos—it feels a little strange to now introduce myself.

I grew up around real estate, was pretty convinced I’d do anything but follow in my parents’ footsteps…and yet, here we are. Turns out I love houses, but I love everything that happens around them even more—the people, the neighborhoods, the design, the community, and creating a place that really feels like yours.

These days, home for me is a 100-year-old house that may never actually be finished, two little kids, a dog, a garden, lots of rearranged furniture, and a pretty full life that I’m incredibly grateful for.

So here’s my turn to share a little bit about how I home. ❤️

— Lauren

10/02/2026

Scroll thatta way for all the details ➡️
DM us for the address 📨
Open houses this weekend 10/3 11-1 and 10/4 10-12
See ya there ✌️

10/01/2026

If Sarah has an off switch, we haven’t found it yet. 😂

She’s always on the go—showings, concerts, workouts, adventures with her son, time with friends and family—and somehow still finds room for more.

But beneath all that Energizer Bunny energy is someone who really loves what home means: a place to slow down, turn on a good record, cook something delicious, and be with your people.

Next up in our Get to Know Our Brokers series, meet Sarah Jenema and see how she homes. ❤️

09/24/2026

Next up on our “get to know our agents” series is Julie Dunne! She’s fast, she’s furious, and she used to be an architect. Can’t wait for you to learn more about Julie…

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. 🛒🥦☀️

Address

1643 N. Milwaukee Avenue
Chicago, IL
60647

Website

http://www.olivewell.com/

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