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Beautiful waterviews of the Chester River set the stage for this special Chestertown property, located in desirable Mile Tree Village and just a short walk from the Historic District. Set on .53 acres, the home offers 1,656 square feet of finished living space on the main level, with 3 bedrooms and 2 full baths, plus an unfinished lower level with a half bath and one-and-a-half-car garage. An upper-level deck, accessible from the living room, dining room, and primary suite, provides the perfect spot to enjoy the river views and the easy Eastern Shore lifestyle. The home is ready for a fresh vision and offers tremendous potential to become a luxury waterview residence. Thoughtful updating could transform the existing spaces into a home that takes full advantage of the setting. Within a short walk or bike ride to Chestertown's Historic District for dinner, shopping, galleries, and Annual Festivals, while the Chester River provides a beautiful backdrop to everyday life. Bring your vision and create a truly special waterview home and experience the Eastern Shore Lifestyle at its finest!

3 Beds ⋅ 3 Baths

Beautiful waterviews of the Chester River set the stage for this special Chestertown property, located in desirable Mile Tree Village and just a short walk from the Historic District. Set on .53 acres, the home offers 1,656 square feet of finished living space on the main level, with 3 bedrooms and 2 full baths, plus an unfinished lower level with a half bath and one-and-a-half-car garage. An upper-level deck, accessible from the living room, dining room, and primary suite, provides the perfect spot to enjoy the river views and the easy Eastern Shore lifestyle. The home is ready for a fresh vision and offers tremendous potential to become a luxury waterview residence. Thoughtful updating could transform the existing spaces into a home that takes full advantage of the setting. Within a short walk or bike ride to Chestertown's Historic District for dinner, shopping, galleries, and Annual Festivals, while the Chester River provides a beautiful backdrop to everyday life. Bring your vision and create a truly special waterview home and experience the Eastern Shore Lifestyle at its finest!

10 Cedar Chase Ct, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

$369,900

Welcome to this beautifully updated country farmhouse, where classic charm meets modern comfort in a serene rural setting. Thoughtfully renovated throughout, this inviting home offers a spacious first-floor primary suite, two additional bedrooms, and generous walk-in attic space—perfect for storage. The main level has been freshly painted and features new flooring, creating a bright, move-in-ready atmosphere. Efficient mini-splits provide comfortable climate control throughout the home, with capacity for one more unit if desired. Step outside through the newer French doors into a fully fenced backyard, ideal for pets, gardening, or simply enjoying the peaceful surroundings. Recent updates include 6 mini-splits, a new hot water heater (installed 11/25), a front roof that is 5–7 years old, and a rear roof just 5 years old with durable 50-year shingles. The third level boasts newly conditioned bonus spaces, offering flexible living or recreational options. Location is a true highlight. Situated minutes from the Sassafras River, a nearby marina, and popular restaurants including the Kitty Knight Inn and Restaurant, Fish Whistle, and Twinny’s. This property places waterfront dining and recreation right at your doorstep. You’re only one mile south of the Fredericktown boat ramp, making boating and water access effortless. Route 301 is an easy 10-minute drive for convenient travel north or south, and the home sits along the Chesapeake Scenic Byway—your gateway to charming waterfront towns such as Chesapeake City, Chestertown, and more. This remodeled farmhouse blends updated living with timeless country appeal and an unbeatable Eastern Shore location. Don’t miss the opportunity to make it yours.

3 Beds ⋅ 3 Baths

Welcome to this beautifully updated country farmhouse, where classic charm meets modern comfort in a serene rural setting. Thoughtfully renovated throughout, this inviting home offers a spacious first-floor primary suite, two additional bedrooms, and generous walk-in attic space—perfect for storage. The main level has been freshly painted and features new flooring, creating a bright, move-in-ready atmosphere. Efficient mini-splits provide comfortable climate control throughout the home, with capacity for one more unit if desired. Step outside through the newer French doors into a fully fenced backyard, ideal for pets, gardening, or simply enjoying the peaceful surroundings. Recent updates include 6 mini-splits, a new hot water heater (installed 11/25), a front roof that is 5–7 years old, and a rear roof just 5 years old with durable 50-year shingles. The third level boasts newly conditioned bonus spaces, offering flexible living or recreational options. Location is a true highlight. Situated minutes from the Sassafras River, a nearby marina, and popular restaurants including the Kitty Knight Inn and Restaurant, Fish Whistle, and Twinny’s. This property places waterfront dining and recreation right at your doorstep. You’re only one mile south of the Fredericktown boat ramp, making boating and water access effortless. Route 301 is an easy 10-minute drive for convenient travel north or south, and the home sits along the Chesapeake Scenic Byway—your gateway to charming waterfront towns such as Chesapeake City, Chestertown, and more. This remodeled farmhouse blends updated living with timeless country appeal and an unbeatable Eastern Shore location. Don’t miss the opportunity to make it yours.

13831 Augustine Herman Hwy, Galena

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

21173 And 21163 Chesapeake Ave, Rock Hall

$649,900

This home has been meticulously maintained and is located in the heart of everything Rock Hall has to offer! The 2 story entrance foyer with tile floors is just the beginning of the surprise you will find in this special, 2,900+/- square foot, home. There are 4 bedrooms, 3.5 baths, a large living room with cathedral ceiling, 2 bedrooms upstairs and 2 bedrooms down, heat pump and mini-split systems for heating and cooling and is move in ready!! A free standing propane stove will help take the chill off during the cooler months. The dining area is just off the kitchen with great views from the large picture window. The kitchen offers all of the major appliances. The laundry room is also a very nice size. There is a side deck for outdoor entertaining. Need storage?.....There is an interior storage/shop room and a large shed to keep some of your summer toys. The crawl space has been recently encapsulated. Need more room or maybe a guest house? The adjoining lot already has sewer and water and is included with the sale. Or just enjoy the open space between you and the next door neighbors. This could make a great full or part time residence! Only a short distance to the harbor and restaurants! Watch the Rock Hall July 4th fireworks right from your deck next year!!

4 Beds ⋅ 4 Baths

This home has been meticulously maintained and is located in the heart of everything Rock Hall has to offer! The 2 story entrance foyer with tile floors is just the beginning of the surprise you will find in this special, 2,900+/- square foot, home. There are 4 bedrooms, 3.5 baths, a large living room with cathedral ceiling, 2 bedrooms upstairs and 2 bedrooms down, heat pump and mini-split systems for heating and cooling and is move in ready!! A free standing propane stove will help take the chill off during the cooler months. The dining area is just off the kitchen with great views from the large picture window. The kitchen offers all of the major appliances. The laundry room is also a very nice size. There is a side deck for outdoor entertaining. Need storage?.....There is an interior storage/shop room and a large shed to keep some of your summer toys. The crawl space has been recently encapsulated. Need more room or maybe a guest house? The adjoining lot already has sewer and water and is included with the sale. Or just enjoy the open space between you and the next door neighbors. This could make a great full or part time residence! Only a short distance to the harbor and restaurants! Watch the Rock Hall July 4th fireworks right from your deck next year!!

21173 And 21163 Chesapeake Ave, Rock Hall

Listing courtesy of Doug Ashley Realtors, LLC. Contact: