easternshoremdfineproperties.com Search Results

$200,000

Investors, contractors & handy buyers—this is the fixer-upper opportunity you’ve been waiting for! This downtown Chestertown diamond in the rough offers strong ARV potential and an opportunity for a fix & flip, long-term rental, or short-term rental. Located just steps from Washington College and an easy walk to historic downtown shops, restaurants, and the waterfront. Currently occupied, but in need of a full renovation, this is a true value-add opportunity in a highly desirable location. Cash or renovation financing only—will not qualify for traditional financing. Priced to move!

4 Beds ⋅ 1 Baths

Investors, contractors & handy buyers—this is the fixer-upper opportunity you’ve been waiting for! This downtown Chestertown diamond in the rough offers strong ARV potential and an opportunity for a fix & flip, long-term rental, or short-term rental. Located just steps from Washington College and an easy walk to historic downtown shops, restaurants, and the waterfront. Currently occupied, but in need of a full renovation, this is a true value-add opportunity in a highly desirable location. Cash or renovation financing only—will not qualify for traditional financing. Priced to move!

223 Mount Vernon Ave, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$599,900

Welcome to 13981 Mill Creek Lane - a wonderful 3 bedroom, 2.5 bathroom cape cod with 2,000+ square feet of living space, screened porch, 2-car attached garage, and 3-car detached garage all on 6 acres in Galena, MD! Upon entry, you'll notice the incredible amount of parking and the convenient circular driveway, making it easy for residents and guests to come and go seamlessly. The main living area features a wood-burning fireplace, great for staying cozy in the cooler months. The eat-in kitchen, complete with large island, has been updated with granite counters and features tile flooring, plenty of cabinet space, and tons of room for a table. Just off the kitchen, the screened porch is a wonderful place to hang, eat crabs in the summer months, and enjoy morning coffee. Down the hall, a formal dining room can fit a massive table to accommodate friends and family, or it can be converted into an office or recreation room. A first floor bedroom and full bathroom are conveniently located on the far side of the home for privacy. Rounding out the main level is the laundry room and half bathroom. Upstairs, the enormous primary bedroom features a walk-in closet, massive bonus room with mini split heating and cooling, and access to the primary bathroom. Down the hall, an additional bedroom rounds out the living space. The detached 3 car garage is more than just a garage - it could serve as an excellent workshop and also features an additional covered area on the back of the garage, great for lawncare storage. Use your 6 acres creatively! If you're a gardener or a hunter, this could be your paradise! Bring your goats and horses! This home is great for the car enthusiast, too - the 5 total garage spaces alone make for an incredibly rare property! There are so many awesome possibilities at 13981 Mill Creek Lane!

3 Beds ⋅ 3 Baths

Welcome to 13981 Mill Creek Lane - a wonderful 3 bedroom, 2.5 bathroom cape cod with 2,000+ square feet of living space, screened porch, 2-car attached garage, and 3-car detached garage all on 6 acres in Galena, MD! Upon entry, you'll notice the incredible amount of parking and the convenient circular driveway, making it easy for residents and guests to come and go seamlessly. The main living area features a wood-burning fireplace, great for staying cozy in the cooler months. The eat-in kitchen, complete with large island, has been updated with granite counters and features tile flooring, plenty of cabinet space, and tons of room for a table. Just off the kitchen, the screened porch is a wonderful place to hang, eat crabs in the summer months, and enjoy morning coffee. Down the hall, a formal dining room can fit a massive table to accommodate friends and family, or it can be converted into an office or recreation room. A first floor bedroom and full bathroom are conveniently located on the far side of the home for privacy. Rounding out the main level is the laundry room and half bathroom. Upstairs, the enormous primary bedroom features a walk-in closet, massive bonus room with mini split heating and cooling, and access to the primary bathroom. Down the hall, an additional bedroom rounds out the living space. The detached 3 car garage is more than just a garage - it could serve as an excellent workshop and also features an additional covered area on the back of the garage, great for lawncare storage. Use your 6 acres creatively! If you're a gardener or a hunter, this could be your paradise! Bring your goats and horses! This home is great for the car enthusiast, too - the 5 total garage spaces alone make for an incredibly rare property! There are so many awesome possibilities at 13981 Mill Creek Lane!

13981 Mill Creek Ln, Galena

Listing courtesy of RE/MAX Chesapeake. Contact:

$349,900

Brand new construction in Chesapeake Landing, and the primary suite is on the main level — full bath, walk-in closet, no stairs at the end of the day. That one detail is what most buyers spend months searching for and rarely find at this price. Roughly 1,600 square feet, laid out so the main floor handles everything: an open living room, a kitchen with shaker cabinets, granite counters and stainless steel appliances, plus laundry and a half bath. Luxury vinyl plank runs throughout — the kind of floor that still looks right after wet boat shoes and muddy paws. Upstairs, two additional bedrooms share a full bath. Guests, an office, a hobby room — tucked away from the main living space so the first floor stays yours. The lot is a third of an acre with a private driveway, giving you real yard on all sides rather than a strip of grass between neighbors. Chesapeake Landing is a waterfront community with a clubhouse, walking trails and community water access. Membership in the community association is voluntary and carries a modest annual fee. Historic Chestertown — the shops, the restaurants, the riverfront — is a short drive away. Everything here is new. New systems, new surfaces, new appliances. Nothing deferred, nothing to renovate, nothing waiting to break in year two. Schedule your private tour today.

3 Beds ⋅ 3 Baths

Brand new construction in Chesapeake Landing, and the primary suite is on the main level — full bath, walk-in closet, no stairs at the end of the day. That one detail is what most buyers spend months searching for and rarely find at this price. Roughly 1,600 square feet, laid out so the main floor handles everything: an open living room, a kitchen with shaker cabinets, granite counters and stainless steel appliances, plus laundry and a half bath. Luxury vinyl plank runs throughout — the kind of floor that still looks right after wet boat shoes and muddy paws. Upstairs, two additional bedrooms share a full bath. Guests, an office, a hobby room — tucked away from the main living space so the first floor stays yours. The lot is a third of an acre with a private driveway, giving you real yard on all sides rather than a strip of grass between neighbors. Chesapeake Landing is a waterfront community with a clubhouse, walking trails and community water access. Membership in the community association is voluntary and carries a modest annual fee. Historic Chestertown — the shops, the restaurants, the riverfront — is a short drive away. Everything here is new. New systems, new surfaces, new appliances. Nothing deferred, nothing to renovate, nothing waiting to break in year two. Schedule your private tour today.

23208 Buck Neck Rd, Chestertown

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442

$424,900

Located in a beautiful waterfront community, this refreshed 5-bedroom, 2.5-bath home offers approximately 1,936 square feet of comfortable living space on approximately 0.38 acres. The property combines updated interiors, flexible living spaces, and the relaxed lifestyle of Maryland’s Eastern Shore. The home offers five generously sized bedrooms, providing comfortable space for family, guests, or work-from-home needs. The versatile fifth bedroom can function as a home office, guest room, flex space, or secondary suite, depending on your needs. The upgraded kitchen features bright white cabinetry, updated countertops and backsplash, stainless-steel Whirlpool appliances, and a KitchenAid dishwasher. The French-door refrigeratorincludes a front water and ice dispenser for added convenience. Attractive ceiling fans throughout the home add both comfort and style. The main living area is anchored by a stylish electric fireplace with custom floating shelving, creating a warm focal point for the home. With five bedrooms, the layout offers excellent flexibility, and the fifth bedroom can also serve as a home office, guest room, or additional flex space. The partially finished one-car garage offers added versatility beyond traditional vehicle parking and storage. It can also serve as a game room, entertainment area, recreation space, hobby room, home gym, or additional flex space, giving buyers even more options for how they use the home. Step outside to an expanded rear deck, hot tub, and fire-pit/seating area, ideal for relaxing or entertaining. Boating enthusiasts will appreciate the nearby seasonal marina with restaurants and a dive bar 3 blocks away and a public boat ramp approximately one mile away, providing convenient access to the area’s waterways. Additional updates include an approximately two-year-old water heater and a private well with an upgraded water-treatment/softening system, professionally serviced in 2025 with a new Clack neutralizer head installed. Whether used as a primary residence, vacation home, weekend retreat, or a home designed for entertaining, 8630 Elm Road offers space, versatility, thoughtful updates, and the Eastern Shore lifestyle in one inviting package.

5 Beds ⋅ 3 Baths

Located in a beautiful waterfront community, this refreshed 5-bedroom, 2.5-bath home offers approximately 1,936 square feet of comfortable living space on approximately 0.38 acres. The property combines updated interiors, flexible living spaces, and the relaxed lifestyle of Maryland’s Eastern Shore. The home offers five generously sized bedrooms, providing comfortable space for family, guests, or work-from-home needs. The versatile fifth bedroom can function as a home office, guest room, flex space, or secondary suite, depending on your needs. The upgraded kitchen features bright white cabinetry, updated countertops and backsplash, stainless-steel Whirlpool appliances, and a KitchenAid dishwasher. The French-door refrigeratorincludes a front water and ice dispenser for added convenience. Attractive ceiling fans throughout the home add both comfort and style. The main living area is anchored by a stylish electric fireplace with custom floating shelving, creating a warm focal point for the home. With five bedrooms, the layout offers excellent flexibility, and the fifth bedroom can also serve as a home office, guest room, or additional flex space. The partially finished one-car garage offers added versatility beyond traditional vehicle parking and storage. It can also serve as a game room, entertainment area, recreation space, hobby room, home gym, or additional flex space, giving buyers even more options for how they use the home. Step outside to an expanded rear deck, hot tub, and fire-pit/seating area, ideal for relaxing or entertaining. Boating enthusiasts will appreciate the nearby seasonal marina with restaurants and a dive bar 3 blocks away and a public boat ramp approximately one mile away, providing convenient access to the area’s waterways. Additional updates include an approximately two-year-old water heater and a private well with an upgraded water-treatment/softening system, professionally serviced in 2025 with a new Clack neutralizer head installed. Whether used as a primary residence, vacation home, weekend retreat, or a home designed for entertaining, 8630 Elm Road offers space, versatility, thoughtful updates, and the Eastern Shore lifestyle in one inviting package.

8630 Elm Rd, Chestertown

Listing courtesy of Save 6, Incorporated. Contact:

$599,900

Welcome to 20714 Wilkins Avenue, a rare opportunity in the heart of charming Rock Hall. Perfectly positioned less than two blocks from the beach, this home is within walking distance of local favorites including Blue Heron Oyster House, Muskrat Alley Café, and the marinas at Osprey Point and Haven Harbour, making it easy to enjoy everything this beloved Chesapeake Bay town offers. Situated on an oversized double lot! This property offers exceptional flexibility and future potential. Whether you’re looking for room to expand, extra outdoor space, or as a short term rental with multiple accommodations, properties like this are rarely available this close to downtown. The 3-bedroom, 2.5-bath home has been thoughtfully updated with a stunning brand-new primary bathroom and new powder room while maintaining its coastal charm. A detached shed has been transformed into additional guest quarters, equipped with a propane stove and window air conditioner, creating the perfect space for visiting family and friends. Step outside to your private 18-foot, three-season gazebo, complete with electricity and perfectly positioned to overlook the water. Whether you're enjoying your morning coffee, watching boats glide in and out of the harbor, or taking in breathtaking sunsets, this inviting space offers the perfect setting to relax and enjoy the beautiful water views. With its prime location, generous lot size, and versatile layout, this property would make an exceptional full-time residence, vacation getaway, or income-producing short term rental. Opportunities like this in downtown Rock Hall don’t come along often.

3 Beds ⋅ 3 Baths

Welcome to 20714 Wilkins Avenue, a rare opportunity in the heart of charming Rock Hall. Perfectly positioned less than two blocks from the beach, this home is within walking distance of local favorites including Blue Heron Oyster House, Muskrat Alley Café, and the marinas at Osprey Point and Haven Harbour, making it easy to enjoy everything this beloved Chesapeake Bay town offers. Situated on an oversized double lot! This property offers exceptional flexibility and future potential. Whether you’re looking for room to expand, extra outdoor space, or as a short term rental with multiple accommodations, properties like this are rarely available this close to downtown. The 3-bedroom, 2.5-bath home has been thoughtfully updated with a stunning brand-new primary bathroom and new powder room while maintaining its coastal charm. A detached shed has been transformed into additional guest quarters, equipped with a propane stove and window air conditioner, creating the perfect space for visiting family and friends. Step outside to your private 18-foot, three-season gazebo, complete with electricity and perfectly positioned to overlook the water. Whether you're enjoying your morning coffee, watching boats glide in and out of the harbor, or taking in breathtaking sunsets, this inviting space offers the perfect setting to relax and enjoy the beautiful water views. With its prime location, generous lot size, and versatile layout, this property would make an exceptional full-time residence, vacation getaway, or income-producing short term rental. Opportunities like this in downtown Rock Hall don’t come along often.

20714 Wilkins Ave, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$375,000

Adorable 4 bedroom 2 bathroom Cape Cod in the quiet Crestview neighborhood in Chestertown close to Restaurants, Shopping, the brand new YMCA and the Historic Downtown. Eat in kitchen with back deck overlooking a beautiful yard that backs up to farm land that is preserved forever. Freshly painted with new carpet! Washer & dryer in unit. Extra storage in knee walls upstairs. In Chestertown but outside the town limits so no town tax or water/sewer bill! Come make this home yours today, immediate occupancy.

4 Beds ⋅ 2 Baths

Adorable 4 bedroom 2 bathroom Cape Cod in the quiet Crestview neighborhood in Chestertown close to Restaurants, Shopping, the brand new YMCA and the Historic Downtown. Eat in kitchen with back deck overlooking a beautiful yard that backs up to farm land that is preserved forever. Freshly painted with new carpet! Washer & dryer in unit. Extra storage in knee walls upstairs. In Chestertown but outside the town limits so no town tax or water/sewer bill! Come make this home yours today, immediate occupancy.

1010 Twin Ct, Chestertown

Listing courtesy of Kevin Dey Realty. Contact:

$765,000

Country elegance at its finest with this recently updated and spacious Cape Cod in the water oriented community of Clearview, just minutes from historic Chestertown. The amenities here are a major plus with Franklin pond and community access directly to Churn Creek. The home has had a transformation in the last 2 years with updated bathrooms, floors, kitchen, landscaping, and a new HVAC unit. The main floor master suite allows you to live in luxury with two walk in closets, hardwood double doors, and brand new bathroom with soaking tub and walk in steam shower. Upstairs is a blend of spacious bedrooms and bathrooms galore with an office nook to look out at nature. Storage is no issue with a full basement ready to take on as many holiday decorations as your heart desires. The property is sprawling on over 4 acres that abut the community pond and green space. Outdoor living is celebrated here with a massive deck out back for entertaining and covered front porch for birdwatching. The abundance of our Eastern Shore is just a short ride away with local staples such as Red Acres Hydroponics and Lockbriar Farms for your produce right in Worton and the Chestertown Farmer's Market for the rest. Invest wisely while improving your quality of life.

4 Beds ⋅ 4 Baths

Country elegance at its finest with this recently updated and spacious Cape Cod in the water oriented community of Clearview, just minutes from historic Chestertown. The amenities here are a major plus with Franklin pond and community access directly to Churn Creek. The home has had a transformation in the last 2 years with updated bathrooms, floors, kitchen, landscaping, and a new HVAC unit. The main floor master suite allows you to live in luxury with two walk in closets, hardwood double doors, and brand new bathroom with soaking tub and walk in steam shower. Upstairs is a blend of spacious bedrooms and bathrooms galore with an office nook to look out at nature. Storage is no issue with a full basement ready to take on as many holiday decorations as your heart desires. The property is sprawling on over 4 acres that abut the community pond and green space. Outdoor living is celebrated here with a massive deck out back for entertaining and covered front porch for birdwatching. The abundance of our Eastern Shore is just a short ride away with local staples such as Red Acres Hydroponics and Lockbriar Farms for your produce right in Worton and the Chestertown Farmer's Market for the rest. Invest wisely while improving your quality of life.

24274 Waterview Dr, Worton

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

$429,900

Welcome home to relaxed Eastern Shore living in the waterfront community of Chesapeake Landing. This beautifully updated 2,140 sq ft Cape Cod offers the perfect blend of charm and modern comfort with 3 bedrooms, 2.5 baths, and a welcoming floor plan designed for everyday life. The main level features new flooring throughout, a spacious living area, formal dining room, and a renovated country kitchen with new appliances, new counters, and plenty of space for gathering. A main-level bedroom adds flexibility for guests or one-level living. Enjoy morning coffee or evening sunsets on the back deck overlooking the open, cleared 0.39-acre lot—perfect for gardening or outdoor fun. Additional highlights include a 2-car garage and access to community amenities with a beach, fishing pier, and pavilion. Just minutes from historic downtown Chestertown, you’ll love being close to local shops, dining, marinas, and all the charm of Eastern Shore living.

4 Beds ⋅ 3 Baths

Welcome home to relaxed Eastern Shore living in the waterfront community of Chesapeake Landing. This beautifully updated 2,140 sq ft Cape Cod offers the perfect blend of charm and modern comfort with 3 bedrooms, 2.5 baths, and a welcoming floor plan designed for everyday life. The main level features new flooring throughout, a spacious living area, formal dining room, and a renovated country kitchen with new appliances, new counters, and plenty of space for gathering. A main-level bedroom adds flexibility for guests or one-level living. Enjoy morning coffee or evening sunsets on the back deck overlooking the open, cleared 0.39-acre lot—perfect for gardening or outdoor fun. Additional highlights include a 2-car garage and access to community amenities with a beach, fishing pier, and pavilion. Just minutes from historic downtown Chestertown, you’ll love being close to local shops, dining, marinas, and all the charm of Eastern Shore living.

10781 Fermoy Rd, Chestertown

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442

$255,000

Good as New. Renovated from top to bottom. Pictures say it all. On the outside we have a new roof, windows, and siding . Inside you will not have to do a thing except make it your own. We have all updated painting and flooring throughout the house . You will find Tile and HVLP flooring which are all heated with propane. Kitchen has been updated and freshened up and ready for a new owner. For all your heating and cooling needs we have a New HVAC unit. All of the quality work and updates that have been done will offer peace of mind for years to come. Welcome Home

3 Beds ⋅ 1 Baths

Good as New. Renovated from top to bottom. Pictures say it all. On the outside we have a new roof, windows, and siding . Inside you will not have to do a thing except make it your own. We have all updated painting and flooring throughout the house . You will find Tile and HVLP flooring which are all heated with propane. Kitchen has been updated and freshened up and ready for a new owner. For all your heating and cooling needs we have a New HVAC unit. All of the quality work and updates that have been done will offer peace of mind for years to come. Welcome Home

11106 Plum Dr, Worton

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$249,500

Discover this beautiful 3-bedroom Cape Cod home in the heart of Worton, Maryland, conveniently located near local amenities and scenic Eastern Shore attractions. Thoughtfully updated with over $20,000 in upgrades, this residence effortlessly blends classic charm with modern comfort. The inviting living spaces feature abundant natural light and elegant finishes throughout. The upgraded kitchen is perfect for both cooking and entertaining, while the spacious bedrooms offer comfort and tranquility. Step outside to a lovely yard with a recently installed privacy fence, ideal for family, pets, evening gatherings, or enjoying your morning coffee. This home offers the perfect combination of charm, comfort, and value. Don’t miss the opportunity to make this beautifully upgraded Cape Cod your new home.

3 Beds ⋅ 1 Baths

Discover this beautiful 3-bedroom Cape Cod home in the heart of Worton, Maryland, conveniently located near local amenities and scenic Eastern Shore attractions. Thoughtfully updated with over $20,000 in upgrades, this residence effortlessly blends classic charm with modern comfort. The inviting living spaces feature abundant natural light and elegant finishes throughout. The upgraded kitchen is perfect for both cooking and entertaining, while the spacious bedrooms offer comfort and tranquility. Step outside to a lovely yard with a recently installed privacy fence, ideal for family, pets, evening gatherings, or enjoying your morning coffee. This home offers the perfect combination of charm, comfort, and value. Don’t miss the opportunity to make this beautifully upgraded Cape Cod your new home.

11060 Plum Dr, Worton

Listing courtesy of Patterson-Schwartz-Newark. Contact: 3027337000