There’s something about life on the Chester River that instantly puts you at ease. The water glistens in the afternoon sun, sailboats drift by at a slow pace, and the air feels just a little lighter. Tucked along these scenic banks sits Chester River Landing, one of Chestertown’s most desirable waterfront communities — where modern design meets small-town charm on Maryland’s Eastern Shore.
A Hidden Gem on the Chester River
Just minutes from downtown Chestertown, Chester River Landing offers an ideal balance between peaceful waterfront living and walkable convenience. This thoughtfully planned community was designed for people who love the beauty of the Bay but want the ease of a low-maintenance lifestyle.
From your back deck, you might catch the reflection of a passing heron or hear laughter from the pool nearby — and yet, you’re only a few minutes from Chestertown’s restaurants, shops, and farmers market. It’s a place where you can have morning coffee by the water and dinner in town without ever feeling rushed.
Community Highlights
Chester River Landing isn’t your typical subdivision — it’s a waterfront haven with resort-style amenities and an authentic sense of place. Homeowners enjoy:
- Private marina and boat slips for lease or purchase. Easy access to the Chester River
- Waterfront communal area with stunning views
- Peaceful community pool and pavilion
- Maintenance-free living (landscaping and exterior upkeep handled by the HOA)
- Walking paths and green spaces throughout the community
- Close-knit neighbors who love the same laid-back lifestyle
It’s the perfect fit for anyone who wants to spend less time on maintenance and more time soaking up the waterfront views.
Location & Lifestyle
Chester River Landing’s location is one of its biggest draws. You’re just over a mile from historic downtown Chestertown, home to independent shops, art galleries, and locally loved restaurants like Watershed Alley and Modern Stone Age Kitchen.
Residents can walk or bike to Washington College, enjoy concerts at Garfield Center for the Arts, and spend weekends exploring nearby destinations like Rock Hall, Eastern Neck Wildlife Refuge, or the scenic Chestertown Marina.
Life here feels peaceful but never isolated — every day brings another opportunity to explore or simply watch the world go by from the dock.
Homes at Chester River Landing
Homes in Chester River Landing combine modern craftsmanship with classic Eastern Shore style — think bright, open layouts, spacious kitchens, and expansive windows overlooking the water.
Most homes include:
- Private decks or balconies with river views
- Attached garages and ample storage
- High-end finishes and open-concept designs
- Options for boat slips or nearby dock access
The neighborhood includes a mix of single family townhomes, duplexes, and condo units each thoughtfully placed to maximize natural light and views. And with exterior maintenance covered, homeowners can focus on what really matters — enjoying life by the river.
Why Buyers Love Chester River Landing
For many buyers, Chester River Landing offers the perfect balance of luxury, comfort, and community. It’s ideal for:
- Retirees seeking a low-maintenance home with high-end finishes
- Professionals wanting a weekend retreat on the Eastern Shore
- Anyone craving water access without the upkeep of a private dock
The community’s welcoming atmosphere and unbeatable river views make it one of Chestertown’s most desirable addresses — and one that only becomes more in demand each year.
Local Expertise Matters
As realtors who live and work along Maryland’s Eastern Shore, we understand the unique character of waterfront living — and how to help buyers find a home that fits both their lifestyle and their goals.
New Homes Now Available at Chester River Landing
New homes are currently in development at Chester River Landing, offering buyers the rare chance to join this community while inventory is available. These newly built properties combine modern design, energy-efficient features, and all the benefits of maintenance-free living — just steps from the water.
Interested buyers can view available listings or schedule a private tour with us to explore floor plans, finishes, and pricing options.
View Available Homes at Chester River Landing
Experience the Best of Chestertown Living
Chester River Landing isn’t just a place to live — it’s a lifestyle. Here, sunsets over the river mark the end of every perfect day, and neighbors gather to share stories on front porches or at the pool.
Contact us today to schedule a private showing or discuss your goals for finding a home on Maryland’s Eastern Shore!
