Connecticut’s Oldest Towns Are Growing Older—Here’s Why It Matters

Neil Caron
Aug 24
2 min read

August 24, 2025 | Connecticut Trends | Presented by ReadySetLoan™️

Connecticut is graying faster than much of the country. The U.S. Census Bureau reports that about 8% of Connecticut residents are now 75 or older, compared with 7% nationally. That small percentage difference tells a big story—one that affects housing, community services, and even the mortgage market.

The Towns Leading the Shift

Winchester saw its 75+ population nearly double in five years, climbing from under 7% in 2019 to nearly 13% in 2023.
Westbrook, Sharon, Morris, and Redding all posted increases of about five percentage points in the same period.
Westbrook now leads the state with 16.6% of residents aged 75+, while Old Saybrook follows close behind at 15.7%.

What’s Driving the Change?

Part of this trend comes from longtime residents simply aging in place, while other towns are attracting retirees who value small-town charm, shoreline proximity, or cultural communities. The Connecticut Department of Social Services also reports steady enrollment growth in programs like the Medicare Savings Program, showing that seniors are putting down roots here.

A Few Surprises

Not every town is trending older. Salisbury actually saw its 75+ population decline by more than six points—the steepest drop in Connecticut—while Norfolk and North Haven also edged downward.

🐷 RSL Piggy Points

Towns like Winchester are aging fast, which may influence future housing needs.
Communities with more seniors often see increased demand for single-level living, downsizing options, and senior-friendly financing solutions.
These shifts can create new opportunities for buyers, sellers, and investors in Connecticut.

🎤 Neil’s Take

“As Connecticut communities age, we’re likely to see ripple effects in housing demand. Seniors may sell larger homes, opening opportunities for younger buyers, while towns will need to expand senior-friendly housing and services. For homeowners, this could mean both challenges and opportunities ahead.”—Neil Caron, Area Sales Manager, CMG Mortgage

The RSL Perspective

At ReadySetLoan™️, we see demographic trends as more than statistics—they’re indicators of where housing demand is headed. Whether you’re looking to downsize, invest, or settle into a Connecticut community with long-term potential, understanding these shifts helps you get to the finish line of homeownership with confidence.

🏁 Ready to explore your options?

Let ReadySetLoan™️ be your guide through Connecticut’s evolving market.