Properties Sold in 2025

Occupying the prominent location on the Sassafras River and commonly known as " The Decker property", this 418 +/- acre farm has over 5,000 feet of waterfront. Waterfrontage on Money Creek and Cox Creek as well. Improved by a rustic lodge with panoramic water views, rolling fields and lawn leading to the water's edge, several barns, waterfowl impoundments with wells strategically located, pond, raised deer blinds, shoreline blinds, private dock with multiple slips, expansive sandy beach and much more.

Price: Sold for $12,000,000

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Waterfront lot in the community of Chesapeake Landing, just outside of Chestertown. This lot has failed previous perc tests and is most likely not buildable.

Price: Sold for $25,000

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Price: Sold for $1,531,833

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Stunning home and property with 180-degree views of the Chesapeake Bay. The home was completely remodeled in 2017 by Taylor Loughry Construction. Boasting a bright open floor plan with high-end finishing, vaulted ceilings with skylights, and beautifully landscaped outdoor space. Two bedrooms and two full bathrooms, open living space with a gourmet kitchen, and a large deck overlooking the Chesapeake. You'll love how the Chesapeake Bay views are framed throughout the home. Enjoy meals on the deck and evenings on the smaller platform deck, perched above the bay. Completely fenced back and side yard facing the water, perfect for pets and some added privacy. The primary bedroom and bath are spacious, boasting bay views, and sliding doors leading to the deck. The office nook lends space for some quiet time. Pull a kayak out and launch on the sandy beach, located down the hill from the home. Launch a boat at the Tolchester Estates boat ramp, or just 2 miles away at the Tolchester Marina. A short drive to the renowned boating community of Rock Hall, and a 20-minute drive to the charming and historic town of Chestertown. This home is the perfect spot for entertaining and relaxing!

Price: Sold for $705,000

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Price: Sold for $1,775,000

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A Rare Opportunity, this craftsman style 3 bedroom, 3 ½ bath home with a main floor primary bedroom is nestled on the serene East Fork of Langford Creek/Bay, and offers the perfect blend of comfort, privacy, and natural beauty. With approximately 150 feet of shoreline and a sandy beach, this property is a true waterfront gem. The great room boasts expansive living space with vaulted ceilings, a loft, and a catwalk for a unique and inviting atmosphere. - The kitchen was beautifully remodeled in 2022 to include modern finishes and appliances, making it the perfect space for entertaining. All the bedrooms offer beautiful views to wake up to. A gentle slope leads you to your own piece of paradise with a sandy beach, ideal for launching kayaks or canoes. Plus, the deep-water boat slip at the community dock provides the perfect haven for boat owners. Enjoy breathtaking water views and refreshing summer breezes from your south-facing waterfront. The property includes a 2-car heated garage, built in 2006, with a separate storage area and a bonus space above—complete with radiant floor heat and AC for year- round comfort. Located within the Cacaway Farm Cooperative Housing Corporation, this home is part of a select group of 5 waterfront properties. Enjoy ownership in a corporation with the added benefit of sharing common expenses for a lower cost of living. Soon the coop ownership is to become a fee simple ownership. Make your appointment today to be a part of that in the near future, with this lower price and no transfer fees. A new BAT septic system was installed in the past 4 years, and the shared sewage disposal area is maintained by the county for worry-free living. This property offers the rare combination of privacy, community, and stunning waterfront access. Don't miss out on this incredible opportunity to own a piece of paradise. Because of its position, the home is perfectly situated to catch the prevailing summer winds from the south, which are often cool and refreshing. This combination of sunlight and breeze provides a wonderful outdoor living experience, whether you’re lounging on the waterfront or enjoying an evening dinner on the deck. It’s the kind of peaceful, tranquil environment that enhances the feeling of living in harmony with nature. Schedule a showing today and make this dream home yours! https://www.instagram.com/reel/DMI5S6-gbSa/?igsh=eXIxOWg3eGhuMms5

Price: $1,195,000

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Welcome to Rigbie Bluff Condominium! This is a rare opportunity for an end unit 2-bedroom condo to be available which offers breathtaking panoramic views of the Upper Chesapeake Bay and spectacular sunsets in the spring & summer. Enjoy waterfront living at its finest with your own boat slip, perfect for boating enthusiasts. Relax by the community pool, take advantage of private beach access, or unwind on your deck while soaking in the serene views. This unit features a spacious basement area, ideal for extra storage or workshop space. Whether you’re looking for a weekend retreat or a year-round residence, this bright and breezy condo delivers the perfect blend of comfort, convenience, and coastal charm.

Price: Sold for $362,500

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Step back in time with this enchanting 1928 waterfront cottage, rich with historic charm and timeless character. Nestled along the serene Elk River, this cozy retreat features original warm wood floors, a striking grand stone fireplace, and breathtaking water views from most rooms. With six bedrooms—including one conveniently located on the main level—there’s ample space for family and guests. The screened porch offers the perfect perch to unwind and watch ships from around the world pass by, adding a touch of maritime magic to your days. Located on a private road leading to a handful of waterfront homes, this rare gem combines privacy, natural beauty, and classic elegance for a truly unique living experience.

Price: Sold for $1,025,000

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Waterfront Living on the North East River! Enjoy stunning waterfront views from this 3-bedroom home perfectly positioned on the scenic North East River. Designed for both comfort and convenience, the home features a lower level with a spacious garage and additional storage, as well as an outside elevator for easy access to the main living areas. A screened porch on the water side offers a peaceful retreat just steps from the river. The main level boasts two bedrooms and an open-concept kitchen, living, and dining area—all with spectacular water views. Expansive sliding doors lead out to a full-width deck, perfect for entertaining or relaxing as you take in the natural beauty around you. Best of all, this property includes its very own private pier, making it ideal for boating, fishing, or simply soaking up the waterfront lifestyle. Bulkhead and dock new in the last 10 yrs. Bonus Opportunity: The adjacent waterfront lot, 2a is available only as a package price with the house for $1.1 million.

Price: Sold for $730,000

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Beautifully maintained waterfront home on the Sassafras River. Family and friend oriented community. Superior blend of tasteful grand home and modern conveniences. Multiple fireplaces for winter warmth and ambiance. Great room sports many windows for a bright interior. Walk out onto porch looking out to the river. A great place for dining alfresco or sipping an afternoon beverage. Nice size bedrooms and spacious owner suite with balcony and breath taking views of the Sassafras River, perfect place for private morning coffee. From the great room enter the water side porch step onto the front yard and claim your spot on one of the cheerful yellow Adirondack chairs and while the day away watching the boating activity. In the evening experience a spectacular sunset. There are stairs into the water for a refreshing swim or lower your boat and explore the wonderful Maryland waterways. Great location for visiting Chestertown, home of eclectic shopping , dining and amenities of Washington College. Close to Rt 301 for points North and South. Perfect home for seasonal or year round living.

Price: Sold for $1,450,000

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This stunning waterfront property completely renovated in 2022 boasts an elegant design that seamlessly blends modern luxury with the serene beauty of its natural surroundings. The spacious gourmet kitchen is equipped with top-of-the-line appliances, perfect for culinary enthusiasts who enjoy cooking while admiring picturesque river views.
The thoughtfully designed waterside hardscaping enhances the outdoor living experience, creating a perfect setting for relaxation and gatherings. The newly installed dock offers direct water access, ideal for boating and fishing activities. The three-car garage provides ample space for vehicles and water toys. The garage also includes an office, making it convenient for those who work from home or serve as guest suite.

Located just minutes from route 301, the home offers quick and easy travel to Philadelphia, allowing residents to enjoy both tranquil country living and the vibrant city life. Nearby attractions include several marinas, parks, and local dining establishments, ensuring a balanced lifestyle filled with opportunities for exploration and leisure.

Price: Sold for $1,095,000

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Exceptional Chester River Landing townhome with elevated views of the Chester River. Enjoy sunrises over the Chester from the balcony and living space. Beautiful views any time of year. A deep water boat slip is included in the sale.
The living room offers, cozy gas fireplace, has beautiful water views all year. This condo boast an open floor plan with tons of natural light, ample room for entertaining and family gatherings. The gourmet kitchen with stainless appliances leads to the dining space which has nice views of the Chester River and community.
Upstairs you’ll find the riverfront primary bedroom, there’s even a view from the soaking tub. Additionally, there are two bedrooms that share a full bath. On the first level there is an office space that could also be used as extra sleeping sleeping space. The large two car garage has enough room for two vehicles and additional storage for all your water toys.
Enjoy the luxuries of the Chester River Landing community, including a pool, community beach, walking paths, beautifully landscaped communal area, waterfront bbq area and much more. Chester River Landing is located just minutes from Historic Chestertown, with many restaurants, shops and entertainment.

Price: Sold for $782,500

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Gorgeous views from this Bayfront property. What could be called the Million Dollar view, but for half the price. This compact bungalow has had extensive work done in the last 20 years but is looking for a new owner to enjoy that spectacular view and take their time to upgrade as feel the need. Steps down to a sandy beach with retaining wall to secure the pilings, recently done. Steps are steep but very secure, however the bottom steps have been washed away. Located in a well established community of Chesapeake Haven, there is a Mandatory HOA, in this section.

Price: Sold for $426,000

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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.

Price: Sold for $750,000

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Exceptional 5 acres on Davis Creek with elevated and panoramic views throughout the property! The dock offers two boat lifts, great water depth and fantastic access to the Chester River and Chesapeake Bay. The very beautiful, rustic cabin has been updated with a ductless mini split for comfortability. Additionally, there is a large fireplace and cookstove. Open living space with great views, enjoy family meals in the dining room or on the cozy porch. The spiral staircase takes you to the primary bedroom and attached full bath. There is a garage with a full bathroom, 4 built-in bunkbeds for additional sleeping quarters, laundry area, and an office space. Attached side garage space is perfect for equipment storage or a workshop. This property is fantastic for hunting, fishing, boating and all outdoor activities The Shore has to offer! Located down the street from the Rock Hall Yacht Club and Lankford Bay Marina. Very walkable and inviting neighborhood located only a short distance from all downtown Rock Hall and Chestertown have to offer.
Strictly by appointment only. Located off a private drive, do not enter without an appointment.
Check Out Property Video Below:
https://show.tours/v/V9PrmYJ

Price: Sold for $950,000

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Park like setting with natural beauty all around you, take a quite day with very nice outdoor den . Watch the herons, eagles, ducks and geese search for food or take a leisurely kayak cruise down Mill Creek to the Chesapeake Bay. Conveniently located a short distance from Worton Creek Marina, Restaurants, Resort Style Marinas, Historic Chestertown, Parks and much more. Chesapeake Landing Offers water access with 2 marinas, boat slips and docks. A perfect location to keep for a weekend away on the beautiful Eastern Shore or primary residence.

Price: Sold for $625,000

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Waterfront rental with a boat slip! Fantastic views every season. Spring, summer & fall boat activity and calm winter vistas. Two bedrooms and two full bathrooms, as well as two half baths. The third floor can be additional sleeping space, and has a deck with a birds eye view. The main level is open living space, great for entertaining! Enjoy all meals on the deck. The best part is the fireworks view on the 4th of July. Best seats in town! Bring your boat and start enjoying the Rock Hall lifestyle. 1-year lease, rental comes fully furnished, renter responsible for utilities, pets on a case-by case basis with deposit.

Price: Sold for $699,000

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