Active Retirement Community in Chestertown, MD
Live the Life You Love at Heron Point of Chestertown
A Historic River Town with the Chesapeake Just Downstream.
Heron Point of Chestertown turns Maryland’s Eastern Shore into part of everyday retirement. Apartments and cottages occupy a 66-acre waterfront setting where residents can walk beside the Chester River, launch a kayak, gather at the dock, or head into historic Chestertown for an afternoon downtown.
“It’s very beautiful here and everyone is so welcoming. They have the space for me to be exactly the person I want to be.”
“I love spending time in the gardens at Heron Point. I’m very grateful to be able to grow so many different plants and get out in nature.”
Benefits of this Chestertown Retirement Community’s Amenities
River Access, Walkable Grounds and Homes with Different Rhythms.
Heron Point’s setting is its defining amenity, but not its only one. Waterfront recreation, fitness, creative spaces, and residential choice make it possible to build an active week without losing the calm of the shoreline.

Direct Access to the Chester River
A campus dock, kayak rack and launcher create convenient opportunities for paddling and time beside the water.

An 800-Foot Boardwalk
The boardwalk extends the waterfront experience and offers a scenic place for walking or pausing by the river.

Two Miles of Walking Paths
Garden-like routes connect homes, amenities and outdoor spaces across the 66-acre property.

Apartments and Cottages
Residents can choose central apartment convenience or a cottage setting with additional privacy and campus views.

A Modern Fitness Center
Separate cardio, free-weight and strength-training areas support different exercise preferences.

A Naturally Lit Art Studio
An atrium-like studio gives classes and individual creative work a bright dedicated setting.

Boating, Golf and Chesapeake Recreation
Local yacht and golf opportunities extend the community's river-oriented lifestyle beyond the property.
Acts Retirement is the Standard for Senior Living
Start a Heron Point Tour at the Water.
Walk the boardwalk and dock area, compare an apartment with a cottage, and visit the fitness and art spaces. That route captures both the river setting and the practical choices of daily life.
Floor Plans
Waterfront Apartments and Cottages with Room to Personalize.
With one- and two-bedroom apartments plus cottage layouts, our Chestertown living spaces have you covered AND make moving incredibly easy with a convenient partnership with LivNow Relocation.
Retirement Community Pricing in Chestertown
Residence and Future Life Care Together.
Far from an added cost, the entrance fee is a prepayment on future healthcare at today’s rates, locking in access to assisted living, skilled nursing, and memory care before they are ever needed.
Residents average 39 to 41 percent in tax deductions on fees as a prepaid medical expense. And if savings are ever outlived through no fault of your own, the Acts Samaritan Fund ensures you are never asked to leave.
Chestertown-centered Senior Health Services
Proper Support is Always Ready.
Every level of care is available on campus, delivered with loving-kindness, so the people who live here never have to leave, and the people who love them never have to worry.
Assisted Living
Help with personal activities and routines.
Skilled Care
Certified treatment for extended needs.
Rehabilitation
Short-term and outpatient therapy support.
Home Health
Care delivered in familiar surroundings.
Chestertown Retirement Community FAQs
Useful Details About Life at Heron Point of Chestertown.
What types of residences are available at Heron Point?
Heron Point offers both senior apartments and cottages. Options range from one-bedroom apartments to larger multi-room cottage homes, allowing residents to choose a residence that fits their preferred space, lifestyle and retirement plans.
What is there to do at Heron Point of Chestertown?
Heron Point offers activities and social opportunities designed to support residents’ physical, mental, cultural and spiritual well-being. Its waterfront location also provides opportunities to enjoy the outdoors and water-based recreation, including sailing on the Chester River and launching smaller watercraft from the community’s shores.
Is Chestertown, MD a good place to retire?
Chestertown can be an appealing place to retire for older adults looking for a smaller town with access to the water and the Chesapeake Bay. The historic town offers classic architecture and boutique shops, while the surrounding Eastern Shore provides opportunities for boating, sailing and other outdoor recreation.
What is there to do in Chestertown during retirement?
Chestertown offers a small-town environment with local shops, historic architecture and access to the Chester River. Retirees who enjoy boating and the outdoors can also take advantage of the town’s location on Maryland’s Eastern Shore and its connection to the Chesapeake Bay.
Does Heron Point offer maintenance-free retirement living?
Yes. Heron Point takes care of responsibilities such as lawn care, snow removal and general maintenance. This gives residents more time to enjoy the community’s activities, amenities and the surrounding Chestertown area without many of the routine responsibilities of maintaining a home.
What healthcare services are available at Heron Point?
Heron Point provides on-site health services, including assisted living and skilled care. This allows residents to enjoy independent living while having access to additional support on campus if their healthcare needs change in the future.
What is Acts Life Care® at Heron Point?
Acts Life Care® combines retirement living with a plan for future healthcare needs. At Heron Point, services such as assisted living and skilled care are available on campus and included under the Life Care arrangement, helping residents prepare for potential changes in their health while they are still independent.
Will my monthly fee increase if I need more care at Heron Point?
Under Acts Life Care®, monthly fees remain consistent regardless of changing healthcare needs. This means a resident’s monthly fee does not increase solely because they need a higher level of care, such as assisted living or skilled care, providing greater predictability for future healthcare expenses.
How much does it cost to live at Heron Point of Chestertown?
Pricing at Heron Point varies based on factors such as the residence selected, location within the community, availability and contract type. Prospective residents can use Acts’ financial assessment calculator or request current pricing information to determine which options may fit their retirement budget.
Is Heron Point a not-for-profit retirement community?
Yes. Heron Point is affiliated with Acts Retirement-Life Communities, a not-for-profit senior living organization. Acts states that its mission is focused on enhancing residents’ lives rather than generating profits for investors.
Can I tour Heron Point before deciding to move?
Yes. Prospective residents can schedule a personal tour of Heron Point to see residences, experience the waterfront campus and learn more about amenities, pricing, activities and Acts Life Care®. Touring the community also provides an opportunity to ask questions and get a better sense of everyday life at Heron Point.
News & Resources
Waterfront Retirement, Wellness and Eastern Shore Retirement Ideas
Read about active living, relocation, financial planning, brain health, and ways to stay connected in Chestertown and along the Chesapeake.
Recent Heron Point of Chestertown News
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See What All Heron Point Has to Offer
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Disclosure: Click here to view Heron Point of Chestertown’s latest disclosure statement.