A Real Story — From a Two-Flat to Lakefront Living
I recently worked with two sisters who had lived for years in a two-flat in another Chicago neighborhood.
One in each unit
A shared life, but separate spaces
As they moved into retirement, they started asking a different question:
“What do we want our everyday life to feel like now?”
The Shift
They weren’t just thinking about:
Space
Price
Location
They were thinking aboutlifestyle
What They Chose Instead
They’re now in the process of purchasing:
Lakefront condos with water views out every window
And their daily life is already shifting:
Elevator building
Door staff + front desk
Valet parking
Indoor Art Deco swimming pool
And Then… The Real Reason
But what matters most to them?
Stepping outside.
To:
The lake
The walking path
The ability to go north or all the way downtown
This Is the Downsizing Most People Don’t Think About
This isn’t:
“Less space”
This is:
More life
Vacation First — At This Stage of Life
This is where your philosophy hits HARD:
Vacation First
Vacate the mind…
Realign your mind, body, and spirit…
Every single day
These are SERIOUS buyers
“I help people transition INTO this lifestyle”
Should I Downsize to a Condo on Lake Michigan in Chicago (or Evanston)?
If you’ve been living in a house or a two-flat in Chicago and starting to think about your next chapter, you might be asking:
“Should I downsize to a condo on Lake Michigan?”
Here’s the truth:
This isn’t just downsizing… it’s a complete lifestyle shift.
And for the right person?
It can be one of the best decisions you make.
This Isn’t About Less — It’s About Different
A lot of people hear “downsizing” and think:
Smaller space
Giving things up
Letting go
But the people I work with?
They’re not thinking smaller.
They’re thinking different.
The Real Question Changes
Instead of asking:
“How much space do I need?”
They start asking:
“How do I want to live every day now?”
A Real Story — From a Two-Flat to the Lakefront
I recently worked with two sisters who had been living for years in a two-flat in another Chicago neighborhood.
One lived in one unit
The other in the second unit
It worked for years.
But as they moved into retirement…
They started rethinking everything.
The Shift
They weren’t just looking for:
Another property
Another layout
They were looking for anew way of living
What They Chose Instead
They’re now in the process of purchasing lakefront condos.
And not just any condos…
Units with Lake Michigan water views out every window
What Their New Life Looks Like
This is where it really changes:
Elevator building
Door staff + front desk
Valet parking
Indoor Art Deco swimming pool
Everything becomes easier.
But This Is the Real Reason
What matters most isn’t inside the building.
It’s what’s right outside.
The lake
The walking path
The ability to go north, south, or just sit and take it in
From Maintenance to Movement
Think about the shift:
Before:
Maintaining a building
Managing space
Handling responsibilities
Now:
Walking the lake
Being outside
Enjoying your time
Vacation First — This Stage of Life
This is where my philosophy becomes even more important:
Vacation First
Vacate the mind… and the rest of your day is bonus
Realign your mind, body, and spirit in nature first
And for many downsizers…
This is exactly what they’ve been waiting for.
What Downsizers Love About Lakefront Living
1. Simplicity
Less maintenance. More freedom.
2. Built-In Lifestyle
You don’t have to plan your day.
You step outside and it’s there.
3. Safety + Convenience
Secure buildings
Staff on-site
Easy access
4. Community
People in similar life stages
Shared lifestyle
Connection without effort
What You Need to Think About
Let’s be real — this is still a big decision.
1. Space Adjustment
You’re trading space for experience.
2. Monthly Costs
Assessments + taxes matter.
3. Building Matters A LOT
Not all buildings are equal.
This is where guidance is critical.
Who This Is Perfect For
This is for someone who:
Is ready for a new chapter
Values lifestyle over space
Wants ease, access, and connection
Feels drawn to the lake
Who It Might Not Be For
This might not fit if:
You’re not ready to let go of space
You don’t value the lake
You prefer a more private, separate lifestyle
My Perspective
I’ve helped people:
Move out of long-time homes
Leave two-flats
Transition into lakefront living
And I’ve seen what happens:
They don’t feel like they downsized.
They feel like they leveled up their life.
So… Should You Downsize to the Lake?
Yes — if you’re ready for a lifestyle shift.
Yes — if you want your everyday life to feel different.
Yes — if the lake already calls you.
Let’s Take A Look See
If you’re starting to think about downsizing and wondering what your next chapter could look like…
Let’s explore it together.
Here are some wise words from a couple of sisters DownSizing!!!
Mary Taylor Sticha (“Pia”)
Broker/Owner – Look See Realty
Chicago, Illinois
708-267-6039
Helping buyers transition into the Vacation First lifestyle along Lake Michigan.
