The Gables at Winchester

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The Gables at Winchester

Senior Living Community in Winchester, Massachusetts:
The Gables at Winchester

299 Cambridge Street
Winchester, Massachusetts 01890
(781) 756-1026

Living Options

Independent Living
Assisted Living
Short Term Stays

Floor Plans



Everyone at this community is very welcoming. Deb makes that place magnificent and Charlene and her whole team are very friendly.

Welcome Home

​​​​​​As you’re walking amidst strong New England pines, playful piano keys and a hint of laughter catch you by surprise. You follow the joyful sounds into our spacious lobby, where residents mingle as another tries their luck at “Piano Man” on the community piano. There’s a sense of fun and wanderlust in the air as your glance shifts to the window. Bright pink shades of rhododendrons dance on the patio where residents are reading. The residents have known each other for a long time—decades, even. But you’re welcomed into the fold immediately as a new friend calls you over. It’s time for dinner—and it’s about time you got here. Welcome home.

Map of the Gables at Winchester


Hospitals / Medical Centers

Hospitals / Medical Centers

Entertainment, arts, and culture

Entertainment, arts, and culture

Near Water

Near Water

Hear from Our Residents

Our residents radiate with joy, laughter, and love for the life they live—and their smiles are our true reward. Whether it’s enjoying live entertainment, happy hour, or our garden club, our residents can’t wait to share with you what they love about The Gables.

"The staff at the Gables have been great to my mother as well as my family. The support, compassion ,an understanding has been above and beyond any expectations we had." - Al DeLucia

News & Events

join us during our virtual open house

Open House

Think Senior Living is Boring?

Think again. In a Five Star community, you have the freedom every day to choose your own adventure. Watch how one resident charts her own path for fun-filled, stress-free senior living.

"Your Complete Guide to the Cost of Senior Living" e-Book

Your Complete Guide to the Cost of Senior Living

Confused about senior living costs? Download our FREE e-book to better understand senior living options, typical cost ranges and financing options. Also find checklists to help guide conversations.

Get the answers you need, so you can make the best choice for you and your family.

Let's start a conversation !

Whether you’re looking for a community for yourself or a loved one, let’s talk about where you can go from here.