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Chestertown, MD, 21620 • 21620 • Kent County
$422/sqft
-$20,000 since Mar 25, 2026
Down payment assistance available
3Beds
2Baths
1,600Sqft
2009Built
On the Chester River
Rip-Rap, Sandy Beach, Private Dock Site, River, Canoe/Kayak, Fishing Allowed, Private Access, Personal Watercraft (PWC), Sail
Scenic Views
Marina · Water · River · Panoramic
Chester River Landing
Boat Dock/Slip · Common Grounds · Elevator(s)
Enhanced Security
Main Entrance Lock · Fire Sprinkler System
Outdoor Living
Porch
1 Fireplace
Gas/Propane
Special Features
Above Grade · Below Grade
1-Car Garage
Garage Faces Front · Garage Door Opener · Detached · Parking Lot
This home is getting attention
Listed 57 days ago · 600 views · 9 saves
Demand and pricing signals for this listing
600 views
People checking out this listing
9 saves
Buyers have saved this home
57 days on market
Established listing
$422/sqft
Price per square foot
This home ranks in the top 33% of listings most likely to go under contract soon, based on market activity and demand signals.
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Condo · Built 2009
Welcome to 118 Little Harbor Way #202, a beautifully reimagined waterfront condo offering effortless living and sweeping panoramic views of the Chester River. Located in the highly desirable Chester River Landing community, this second-floor, 3-bedroom, 2-bath residence delivers the perfect blend of modern luxury, low maintenance, and classic Eastern Shore charm. Completely taken down to the studs and thoughtfully rebuilt, the condo feels brand new from top to bottom. The open floor plan is filled with soft, natural light and showcases wide-plank wood flooring, a cozy gas fireplace, and uninterrupted river views from the main living areas. The stunning kitchen features white quartz countertops and backsplash, stainless steel appliances, and a seamless flow for both everyday living and entertaining. The primary suite is a true retreat, complete with a walk-in closet and a spa-like tiled shower with multiple shower heads, including a rainfall feature. Both bathrooms are finished with timeless, high-quality materials, creating a clean, classic, and calming feel throughout. Step out onto the private balcony and take in peaceful, north-facing river views with soft, consistent light throughout the day. It is ideal for relaxing, reading, or simply watching boats drift by without the glare of direct sun. This is waterfront living at its most comfortable and serene. Additional features include elevator access to the second floor, a one-car garage, and a deeded boat slip, approximately 4 feet MLW. The community offers a pool, fishing pier, and marina with floating docks, along with beautifully maintained grounds featuring oyster shell walking paths and a firepit. The marina area also includes a community grill and multiple tables, perfect for outdoor dining and gathering. Flood insurance is not currently required for this second-floor unit, contributing to overall affordability. Buyers are encouraged to perform their own due diligence and verify any insurance requirements. Ideally located within walking distance to historic downtown Chestertown, and just a short drive to golf, dining, and the yacht club at Chester River Yacht and Country Club, this condo is perfectly suited for those looking to downsize, simplify, or secure a refined second home on the water. Move in ready, thoughtfully updated, and designed for relaxed coastal living, this is Eastern Shore living at its finest.
Standout features identified
Our analysis highlights waterfront condo, cozy gas fireplace, and walk-in closet as key attractions of this home.
Based on current rates
Est. 6.10% rate · 30yr fixed · $540,000 loan
Full calculator →Key facts and listing details
16 categories of property features
5 rooms detailed
Bedroom1
MainBedroom2
MainBedroom3
MainBathroom1
MainBathroom2
MainMarket data and value estimates
3 schools rated nearby
Chestertown, MD, 21620
6 events
17 years of records
Local context around this listing
Chestertown, MD • Kent County
Nearby neighborhoods
Nearby cities
Nearby zip codes
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