How Much Is Your Home Worth?

55+ Communities on Chicago's North Shore & Northwest Suburbs

Ready to trade the snow shovel for the social calendar? Winfield Cohen helps active adults find low-maintenance homes in 55+ communities across Northbrook, Glenview, Buffalo Grove, Deerfield, and the surrounding suburbs, so you can stay close to the people and places you love with far less upkeep.

Why Active Adults Are Choosing to Stay Close to Home

Many people assume retiring means leaving Illinois. More and more, they're choosing to stay, and for good reasons. Illinois does not tax Social Security benefits, and most retirement income, including pensions, 401(k) and IRA withdrawals, is also exempt from state income tax. Homeowners 65 and older may also qualify for senior property tax exemptions and an assessment freeze that can help keep costs predictable.

Active adults choosing to stay near home in the North Shore suburbs

Active 55+ Properties

Available 55+ Listings on the North Shore

Why a 55+ Community Makes Sense Now

Say Goodbye to Snow Duty

Chicago winters are no joke. Your HOA typically handles snow removal, lawn care, and exterior maintenance, so you can spend January planning a trip instead of shoveling a driveway.

Put Your Equity to Work

Many long-time North Shore homeowners have built substantial equity in their family homes. Selling can free up funds for travel, family, or simply a more comfortable retirement.

Community Built In

Clubhouses, fitness classes, card groups, holiday events, and neighbors who share your stage of life. It's easy to stay connected when connection is part of the design.

Stay Near Family

Moving to a 55+ community nearby means keeping Sunday dinners, school recitals, and weekend babysitting on the calendar without the distance of relocating out of state.

Top-Tier Healthcare Nearby

The area offers access to hospitals including Endeavor Health Glenbrook and Evanston Hospitals, Northwestern Medicine Lake Forest Hospital, and Northwest Community Hospital.

Simplify Your Monthly Budget

A right-sized home often means lower utilities, less maintenance, and in many cases a lower property tax bill than a larger family home.

How Winfield Cohen Helps

From Your First Call to Your First Night in Your New Home

1

Free, No-Pressure Consultation

We start with a conversation about your timeline, budget, and how you want to live. There's no obligation and no sales pitch.

2

Sell Your Current Home for Top Value

Winfield Cohen prepares, prices, and markets your home strategically to protect your equity and maximize your return.

3

Find the Right Community

He'll narrow your options to 55+ communities that match your lifestyle, preferred location, and budget, and help you compare HOA costs, amenities, and rules.

4

Close and Move In with Confidence

Winfield Cohen coordinates both transactions and aligns the timing so your transition feels smooth rather than stressful.

Request a Free Consultation

Ready to Explore 55+ Communities on the North Shore?

We’ve Got Answers

Frequently Asked Questions

Is the Chicago North Shore a good place to retire?

For many people, yes. Illinois doesn't tax Social Security or most retirement income, and seniors may qualify for property tax relief programs. Add excellent hospitals, beautiful parks and forest preserves, strong cultural offerings, and proximity to family, and staying local often makes more sense than moving away.

What amenities do 55+ communities in this area usually offer?

It varies by community, but common features include a clubhouse, fitness room, walking paths, and organized social events. Some larger communities add pools, pickleball courts, and hobby rooms. Your HOA fee typically covers shared amenities and exterior maintenance, and Winfield Cohen will help you understand exactly what's included before you buy.

Are pets allowed in 55+ communities?

Many communities welcome pets, but rules differ. Some limit size, breed, or number of pets. Share your pet's details early and Winfield Cohen will make sure every community you tour is a good fit.

Do I have to sell my home before buying in a 55+ community?

Not always. Some buyers use bridge financing or a contingent offer to buy first, while others sell first and rent briefly. The best option depends on your finances and market conditions, and Winfield Cohen coordinates both sides so you're never stuck between homes.

Are there new construction 55+ homes in the area?

New construction does come up, though availability varies. New builds offer modern layouts, energy efficiency, and warranties but can involve longer timelines. Resale homes are often available sooner and may already have upgrades. Winfield Cohen tracks both and can alert you when something matching your criteria becomes available.

What should I look for when touring a 55+ community?

Look past the model home. Visit the clubhouse on a weekday to see how active it really is, check the condition of common areas, and ask for the HOA's budget and reserve fund information. Also consider how far you'll be from your doctors, pharmacy, and family.