Two people walk side by side on a wooden boardwalk through tall grasses toward a covered dock over the water.

Active Retirement Community in Chestertown, MD

Live the Life You Love at Heron Point of Chestertown

501 E Campus Ave, Chestertown, MD 21620 Get Directions

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.

Tour Heron Point of Chestertown

Gini Newlin Heron Point resident

“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.”

Connie Schroth Heron Point resident

“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.”

Two women are in a library; one is sitting on a couch reading a book and smiling, while the other stands near a bookshelf browsing for a book.
Lounge area with patterned sofas, a coffee station, and a wooden sailboat suspended from the ceiling. Magazines are on a round table; framed art hangs on a paneled wall.
A clean, modern dining area with round tables, cushioned chairs, wood flooring, and buffet stations in the background under bright lighting.
Wooden boardwalk leading to a gazebo by a lake, with a dock and colorful kayaks nearby, surrounded by reeds and trees in the background under a partly cloudy sky.

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.

Simple blue line drawing of a kayak seen from above with a double-ended paddle laid diagonally across it, on a light gray background.

Direct Access to the Chester River

A campus dock, kayak rack and launcher create convenient opportunities for paddling and time beside the water.

Blue line drawing of the sun, three pine trees, and a curved shape suggesting a lake or body of water, on a light background.

An 800-Foot Boardwalk

The boardwalk extends the waterfront experience and offers a scenic place for walking or pausing by the river.

Simple blue line drawing of a person walking, depicted in a minimalist stick figure style on a light background.

Two Miles of Walking Paths

Garden-like routes connect homes, amenities and outdoor spaces across the 66-acre property.

Simple blue outline of a house with a heart shape in the center, set against a light background.

Apartments and Cottages

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

Simple line drawing of a person lifting a barbell overhead, symbolizing weightlifting or strength training.

A Modern Fitness Center

Separate cardio, free-weight and strength-training areas support different exercise preferences.

Blue outline icon of an artist’s paint palette with five wells and a paintbrush resting across it, on a light background.

A Naturally Lit Art Studio

An atrium-like studio gives classes and individual creative work a bright dedicated setting.

Simple blue line drawing of a person swinging a golf club near a golf ball, with a golf bag containing clubs shown nearby—capturing the leisurely lifestyle found in Gainesville senior apartments and carriage homes or within the vibrant Lake Lanier retirement community.

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

50 + Years
Not-for-Profit Excellence
96 %
Resident Satisfaction
28
Communities & Growing
Two people walk on a wooden footbridge surrounded by trees, with residential buildings visible in the background on a cloudy day.

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.

Schedule a Tour

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.

View Floor Plans

Black and white floor plan showing two bedrooms, two baths, kitchen, den, living/dining area, front and back porches, and labeled fixtures, appliances, and room dimensions.
A long wooden boardwalk leads from the water through marsh grass to a residential area, with benches, gazebos, and kayaks docked on the left.

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.

View Full Pricing Details

Talk to a Life Care Consultant

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.

Learn More

Blue line drawing of two hands holding up a house, symbolizing protection or care for a home.

Assisted Living

Help with personal activities and routines.

Two hands shaking, forming the shape of a heart, drawn with simple blue lines on a light background.

Skilled Care

Certified treatment for extended needs.

Line drawing of a human head in profile with a heart shape inside the brain area, symbolizing emotional intelligence or empathy.

Rehabilitation

Short-term and outpatient therapy support.

Simple blue line drawing of two crutches crossed over each other on a light background.

Home Health

Care delivered in familiar surroundings.

Chestertown Retirement Community FAQs

Useful Details About Life at Heron Point of Chestertown.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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

Browse All Retirement Resources

 

See What All Heron Point Has to Offer

Request a detailed information kit with pricing, floor plan, community amenities and more!

Request Your Kit Today

Disclosure: Click here to view Heron Point of Chestertown’s latest disclosure statement.