The Overlook

The Overlook in Charlton, MA offers retirement living on 450 spectacular acres in Worcester County, MA. Ideally located in the heart of New England and just a short distance from Boston, Providence, and Hartford, our community is surrounded by exciting places, interesting people and infinite opportunities to keep learning and growing. As one of the finest retirement communities in Massachusetts, we’re proud to offer a full continuum of health care, should you ever need it. With so much to do and enjoy in all directions, it’s no surprise that The Overlook attracts people from all around. They come for the spectacular setting. They come for the spacious and elegant residences. They come to savor the dining options, the indoor heated pool, the Performing Arts Center and a full calendar of events. They come to experience the endless ways to enjoy the next chapter in their story. And with a 450-acre backyard, our campus stands apart from other retirement communities in Massachusetts. Hosting family and friends has never been easier with welcoming outdoor gathering spaces, full-service catering, and multiple dining venues. You’ll always have the option to picnic, garden, hike, cross-country ski, play tennis, practice your putting and discover countless other ways to stay active and engaged in the “Heart of the Commonwealth.” We invite you to explore The Overlook’s wide variety of living options, including cottages, apartments, and suites across independent living, assisted living and memory care. Once you’ve taken a peek, schedule an in-person visit to see how great your future can look from here. Independent living at The Overlook is all about enjoying your retirement, your way. We provide the breathtaking New England backdrop and a welcoming, active community. You choose the retirement lifestyle that’s right for you. Located just an hour outside of Boston on 450 acres of untouched New England countryside in Worcester County, MA, The Overlook is the perfect choice for city lovers and nature lovers alike.