Comfort. Nature. Luxury. All are expressed in this Contemporary waterfront home on Southeast Creek. Listen to Ospreys from your screened porch or private second floor balcony. Cool off in the pool or practice yoga in the poolside studio space. Friends from far away can come use your detached guest cottage as a tranquil retreat. Walk down your dock and go sailing with easy access to the Chester River and beyond. Gather with the ones you care about most on the central open floor plan on the main floor. Upstairs has everything you need to decompress and take in the fine Eastern Shore lifestyle. The home is less than 15 minutes from Historic Downtown Chestertown by boat or car and less than 2 hours from Washington D.C., Philadelphia, or Baltimore.

This is your chance to own one of the most prominent homes in Chestertown's Historic District already completely upgraded and finished to suit. The Tilley Residence was rebuilt in 1863 and celebrates the Second Empire style reminiscent of the Champs-Élysées in Paris. The neighboring properties on this sought after corner are some of the area's most important including Widehall and the Custom House which was one of the original British Royal Ports of Entry to the Americas. The current owners include one of Kent County's renowned builders and craftsmen who decided to take on this restoration as a passion project to honor its beauty and significance in the community. The home was completely updated in 2024 with new HVAC, Electrical, Plumbing, roofing, and wood flooring. The floor plan was opened up to accommodate your lifestyle in 2025. New bathrooms and kitchen were custom designed. A grand 3 story staircase greets you at the foyer along with arched entryways to introduce you to the level of detail to be found throughout. The front porch allows you to sit back to watch everything happening in town or simply admire the water. The updated layout is designed for optimal flow and natural light. The primary suite captivates you with a fireplace, spacious walk in closet, and tiled shower room with views of the water from two sides. The Mansard roof allows for the full third floor. In the basement there is a partially finished space perfect for your wine cellar along with extra unfinished tidy space for storage. There is also a fenced in rear yard perfect for intimate gatherings, pets, and gardening. Off street parking is a huge plus as well with a detached garage connecting to the rear yard. Due to this property's grandeur and scope of work, the sellers are going to let you decide on some finishes to make you feel you spend wisely. Allowance lists to be provided to interested parties. Turn this important and updated piece of Chestertown History into your Legacy property.

This Waterfront Contemporary home is nestled on a bluff with sweeping views of Still Pond Creek. The property checks all of the boxes for your retreat including a well maintained deck, screened river room for crab feasts, private sandy beach and dock with several boat lifts. The living room has a cathedral ceiling, wood burning fireplace, and glass sliders leading you to the deck with incredible views of nature and wildlife. One of the 3 main floor bedrooms, the primary suite has an ensuite bathroom, walk-in closet, and full length windows to celebrate the property's connection with the water. On the lower level you will find another bedroom, den, workshop, and garage. Upgrades include New Heating and Cooling (2024&2025), New Roof (2022), Garage Door (2024), Plumbing and Electrical Updates (2022), Generator, Rinnai Tankless hot water heater, and Reverse Osmosis water treatment. Still Pond Creek provides direct access to the open waters of the Chesapeake Bay for prime boating opportunities however is a protected tributary making it great for water sports. The property is located in the rolling farmlands of Worton, only 15 minutes from the shops, restaurants, and galleries of downtown historic Chestertown. Philadelphia, Washington D.C., and Baltimore are all less than a 2 hour drive making this perfect for a weekend getaway or year round residence.

This waterfront farmette is a rare find just a few minutes from downtown Chestertown and features extensive updating. The new kitchen, 2 new full bathrooms, and new roof all from 2024 just to name a few have you set up for many years to come. Most of the property is cleared and grassy making it perfect for your equestrian retreat on the water. A detached 2 car garage is perfect for vehicles or water toys. The river room is flooded with natural night and offers prime views of the surrounding wildlife. Stay cozy with the wood burning fireplace. Fishing and hunting are prime in this location. Feel a sense of peace and tranquility on this very private 9 acres while being able to drive to the historic district for the shops, art galleries, theatre, and restaurants in less than 10 minutes. Chestertown is located just 1.5 hours from Washington DC, Philadelphia, and Baltimore.

Big, bold, and beautiful! This wonderfully updated 2 story brick colonial in Chestertown is just minutes walking to the shops, restaurants, college, and waterfront. The first floor is enhanced with a finished sunroom with mini split, well appointed full bathroom adjacent to the office, and the kitchen of your dreams. Traditional aspects remain with a spacious dining room with built ins and living room with fireplace. The upstairs has 4 bedrooms including the primary suite with dressing room, private balcony and en suite bathroom equipped with radiant floor heat. Half of the third floor is finished as well with a mini split and skylights for hobbies while the other half is perfect for storage. Not that storage is a issue with this full basement including a workout room and dance studio as well. The lush grass yard is tastefully landscaped and easily enjoyed with privacy on your rear deck. Keep your cars and favorite toys clean with the 3 car garage. Spare no detail and live luxuriously in this Eastern Shore gem.

Welcome to your private oasis! This charming home boasts mature landscaping that provides both beauty and privacy on a large corner lot. Custom built Cape Cod offers a first floor primary suite, living room with fireplace and built ins, formal dining room and a kitchen with granite counters and updated appliances. There’s an open area on the 2nd level ideal for reading or watching TV. Plus 2 more bedrooms and an office. Updates include: new carpet primary BR, garage door 2024, roof Dec 2022. Enjoy the serene ambiance from the large deck, overlooking a picturesque pond with not one, but two enchanting waterfalls. The soothing sound of cascading water creates a tranquil atmosphere, perfect for relaxation and unwinding. This property is a true retreat, offering an idyllic escape right in your backyard. Located just minutes from the Chester River and Chestertown’s historic district.

Historic charm with a modern floor plan. Live just around the corner walking to the shops, galleries, and restaurants of downtown Chestertown in this beautifully updated Victorian on quiet Mill Street. High end appliances such as Miele and Bosch adorn the kitchen and laundry. Easily converted back into a 3 bedroom. The backyard is well landscaped, has a covered outdoor living space, and a spacious detached hobby shed or office space. This low maintenance property with walkable lifestyle works perfectly for a weekend retreat or year round residence. Chestertown is located less than 1.5 hours from Washington D.C, Philadelphia, and Baltimore.