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220 Old Steamship Rd, Stevensville
$1,950,000
4 Beds ⋅ 5 Baths
WATERFRONT (20 acres) located on the Northern section of Kent Island, in the area of larger acreage estates, the "Pink House" provides a peaceful respite from the rush of the world. As easy 5 minute drive from the Chesapeake Bay Bridge the home offers access to the western shore metro areas. NO SUBDIVISION POTENTIAL With over a 1000' of protected shoreline fronting along the broad, open waters of the Chester River the has 100'+ pier offers 4' MLW. A waterfowl hunter's delight you'll find a blind on the pier and one offshore as well. A generously proportioned inground pool with an expansive apron for lounging and dining is a focal point between the house and the river. An outdoor kitchen, huge deck and a screened gazebo invite spending time outdoors. A conservatory suitable for greenhouse functions or outdoor dining under cover is reminiscent of older European estate gardens. Established landscaping with unique plants surround the home and outdoor spaces. The residence is a blend of eclectic flair and flowing functionality. Designed to maximize views, the generous square footage offers a main level owners suite and three upper en-suites. Many custom features such as the designer counter tops and backsplash in the kitchen, hint at the uniqueness of this home. The "Pink House" offers secluded acreage at the end of a tree lined circular driveway. With some needed renovations and designer touches this home has the potential to be a showplace! CRAB this opportunity to own one of Kent Islands finer properties along the Chester River.

220 Old Steamship Rd, Stevensville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: Non Subscribing Office.

212 Landing Ln, Chestertown
$750,000
3 Beds ⋅ 4 Baths
Nestled along the tranquil western shore of the Chester River, this beautiful townhome in Chester River Landing offers an unparalleled waterfront living experience with direct water access and captivating water views. Just a short stroll from the historic heart of Chestertown, MD, it combines modern luxury with timeless charm. This elegant 3-bedroom, 2.5-bath residence is designed to maximize comfort and style. The spacious living areas are bathed in natural light, enhancing the serene ambiance of this waterfront haven. The open-plan living and dining areas flow seamlessly into the well-appointed kitchen, equipped with top-of-the-line appliances and ample storage. The master bedroom is a true retreat, with easterly river views and an ensuite bath. The additional bedrooms are generously sized, perfect for family or guests. The 3.5 baths are elegantly designed, featuring modern fixtures and finishes. One of the standout features of this home is its perfect vantage point for watching the daily sunrise. Imagine starting your day with a cup of coffee on the balcony, as the first light of dawn reflects off the calm waters of the Chester River while rowing teams begin their daily workout. Whether you're seeking a peaceful waterfront retreat or a picturesque spot to entertain, this townhome offers it all. The community amenities of Chester River Landing further enhance the lifestyle, with walking paths, swimming pool, private pier with available boat slips for purchase or lease, outdoor grilling and beautifully landscaped common areas. Discover the unique blend of history, luxury, and natural beauty at this waterfront home on the Chester River.

212 Landing Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Unrepresented Buyer Office.

118 Little Harbor Way Unit 201, Chestertown
$665,000
2 Beds ⋅ 3 Baths
An impeccably maintained, perfectly positioned two bedroom, two and one-half bath condo featuring one of the best vistas of Chestertown and the Chester River. Here, body, mind, and spirit naturally align - it's simply impossible not to feel balance. River House, with only five private residences, occupies the best real estate within this prized, friendly and well managed neighborhood called Chester River Landing. Historic downtown Chestertown and the Chester River Yacht & Country club are less than 2 minutes away, when you need a break from your enclave that includes marina, grill patio, crabbing/fishing pier, beach area for kayak launch, waterfront green space with fire pit, community garden, and pool with pool house. Unit 201 includes a nearby 1 car garage with overhead storage racks and a deeded premium boat slip (A7) A unique feature of this home is a custom HVAC and air quality system, ideal for anyone with seasonal allergies, chemical sensitivities, or just appreciative of quality air and healthy living. New GE range, LG and 03 Pure Eco Laundry System installed 2025. (Warranties convey). The lobby and all common areas have recently been beautifully redecorated and furnished. As part of CRL commitment to maintaining property excellence, the entire exterior of River House is currently receiving new siding, flashing and other pro-active improvements at no cost to the new owners.

118 Little Harbor Way Unit 201, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

118 Little Harbor Way Unit 202, Chestertown
$660,000
3 Beds ⋅ 2 Baths
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.

118 Little Harbor Way Unit 202, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Doug Ashley Realtors, LLC.