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Experience the best of in-town Chestertown living in this custom-built single-level home! The open floor plan features abundant natural light, gleaming hardwood floors and a bright, inviting layout perfect for entertaining or relaxing. The dining room is open to the kitchen which includes some updated appliances, ample cabinet storage, and a breakfast bar. The primary suite has a large walk-in closet and an en-suite bath which now boasts a soaking tub. Step outside to enjoy the large deck, fire pit patio, and fully fenced backyard. This home offers comfort and convenience at every turn. Just a few blocks from Washington College and a short stroll to Downtown Chestertown’s charming restaurants, shops, and waterfront.

411 Greenwood Ave, Chestertown

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

Selling Office: Monument Sotheby's International Realty.

$412,000

This 3,000 SF commercial building was originally constructed in 2001, but was significantly improved in 2020 and most recently used as a veterinary hospital. A 29 ft x 16 ft reception area, 8 treatment rooms/offices and 2 restrooms offer a user-owner or investor a flexible layout for a variety of uses. Dual heat pumps with propane back up provide multi-zoned conditioning for the building. Two ADA compliant bathrooms and an entry ramp are in place. There are sealed concrete floors in the work spaces and new high quality vinyl planked flooring in pubic areas. A 5KW Generac back up generator insures uninterrupted power to the building. The property is served by public water and sewer and there is a whole-building water filter installed. Crossroads Commercial zoning offers a wide range of permitted uses. Conveniently located on Rt. 20, 5 minutes outside the town of Rock Hall.

6270 Rock Hall Rd, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: Unrepresented.

$410,000

Charming Move-In Ready Colonial in the Heart of Town This beautifully updated Colonial blends timeless character with modern comfort. Ideally located within walking distance of local restaurants, shops, and the scenic waterfront, it offers the perfect combination of charm and convenience. The exterior showcases classic Colonial appeal with vibrant shutters, fresh paint, new roof, gutters, doors, and Andersen double-hung tilting sash windows.The welcoming front porch overlooks manicured flower beds that enhance curb appeal, while the private backyard provides the perfect setting for weekend gatherings and cookouts or just outdoor relaxation. Inside, the home has been thoughtfully renovated from top to bottom. Recent updates include a Mitsubishi Mini-Split heating and cooling system,Rinnai propane instant hot water heater, and 200-amp electrical service with all-new wiring, fixtures, and recessed lighting throughout. The kitchen is a true showstopper that is completely transformed with new cabinetry, quartz countertops, a center island, stainless steel appliances, and a vented range hood. Refinished rustic hardwood floors run throughout the main level, seamlessly blending old world craftsmanship with modern design. A separate Laundry room features a new washer and dryer with Electric Hookups. Upstairs, you’ll find comfortable bedrooms with Shaw carpeting and pet-proof padding and a beautifully updated bathrooms featuring tiled walls and floors, new vanity, and modern fixtures. The dry basement offers a wide step entrance from Laundry Room with excellent storage space, a new 200-amp electric panel, vapor barrier, and plenty of room for a workshop or home gym or Man Cave. Enjoy the best of in-town living with everything you need just a short stroll away. Schedule your tour today and fall in love with this move-in ready gem

Charming Move-In Ready Colonial in the Heart of Town This beautifully updated Colonial blends timeless character with modern comfort. Ideally located within walking distance of local restaurants, shops, and the scenic waterfront, it offers the perfect combination of charm and convenience. The exterior showcases classic Colonial appeal with vibrant shutters, fresh paint, new roof, gutters, doors, and Andersen double-hung tilting sash windows.The welcoming front porch overlooks manicured flower beds that enhance curb appeal, while the private backyard provides the perfect setting for weekend gatherings and cookouts or just outdoor relaxation. Inside, the home has been thoughtfully renovated from top to bottom. Recent updates include a Mitsubishi Mini-Split heating and cooling system,Rinnai propane instant hot water heater, and 200-amp electrical service with all-new wiring, fixtures, and recessed lighting throughout. The kitchen is a true showstopper that is completely transformed with new cabinetry, quartz countertops, a center island, stainless steel appliances, and a vented range hood. Refinished rustic hardwood floors run throughout the main level, seamlessly blending old world craftsmanship with modern design. A separate Laundry room features a new washer and dryer with Electric Hookups. Upstairs, you’ll find comfortable bedrooms with Shaw carpeting and pet-proof padding and a beautifully updated bathrooms featuring tiled walls and floors, new vanity, and modern fixtures. The dry basement offers a wide step entrance from Laundry Room with excellent storage space, a new 200-amp electric panel, vapor barrier, and plenty of room for a workshop or home gym or Man Cave. Enjoy the best of in-town living with everything you need just a short stroll away. Schedule your tour today and fall in love with this move-in ready gem

109 S College Ave, Chestertown

Listing courtesy of Taylor Properties. Contact:

Selling Office: LPT Realty, LLC.

$409,000

Step onto the inviting front porch and into a home designed with both comfort and functionality in mind. The kitchen features a large breakfast room, center island, and built-in desk, providing an ideal space for everyday meals, gathering, and staying organized. A formal dining room and formal living room offer additional spaces for entertaining and special occasions. The oversized family room is sure to be a favorite, featuring a gas fireplace and plenty of space for everyone to spread out. Upstairs, you'll find four comfortable bedrooms, including a spacious primary suite. Outside, enjoy the fenced backyard, back deck, and corner-lot setting—perfect for outdoor entertaining, play, gardening, or simply relaxing. With its welcoming front porch, generous interior spaces, and convenient Millington location, this home offers the space and features you've been looking for. Come see all that 217 School St has to offer!

Step onto the inviting front porch and into a home designed with both comfort and functionality in mind. The kitchen features a large breakfast room, center island, and built-in desk, providing an ideal space for everyday meals, gathering, and staying organized. A formal dining room and formal living room offer additional spaces for entertaining and special occasions. The oversized family room is sure to be a favorite, featuring a gas fireplace and plenty of space for everyone to spread out. Upstairs, you'll find four comfortable bedrooms, including a spacious primary suite. Outside, enjoy the fenced backyard, back deck, and corner-lot setting—perfect for outdoor entertaining, play, gardening, or simply relaxing. With its welcoming front porch, generous interior spaces, and convenient Millington location, this home offers the space and features you've been looking for. Come see all that 217 School St has to offer!

217 School St, Millington

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

Selling Office: Patterson-Schwartz-Newark.

$407,500

Fully furnished! Adorable rancher in a PRIME location in Rock Hall. Just steps to the marinas, restaurants, and shops. The house has been completely remodeled. All new appliances. Large family room with a pellet stove and plenty of space for social gatherings. Nice-sized bedrooms and 2 full bathrooms. Luxury vinyl plank flooring throughout. Detached garage and potting shed. Less than 1/2 mile to the public beach. Private backyard with koi pond and water feature. The current owners have their boat docked at a nearby slip, and they can see it from the property. There is no work to be done here. Just bring a suitcase and move right in!

Fully furnished! Adorable rancher in a PRIME location in Rock Hall. Just steps to the marinas, restaurants, and shops. The house has been completely remodeled. All new appliances. Large family room with a pellet stove and plenty of space for social gatherings. Nice-sized bedrooms and 2 full bathrooms. Luxury vinyl plank flooring throughout. Detached garage and potting shed. Less than 1/2 mile to the public beach. Private backyard with koi pond and water feature. The current owners have their boat docked at a nearby slip, and they can see it from the property. There is no work to be done here. Just bring a suitcase and move right in!

5697 Walnut St, Rock Hall

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

Selling Office: Unrepresented Buyer Office.

$400,000

Excellent Opportunity to own a great 50+/- acre hunting and recreational property in northern Kent County Maryland. Diverse wooded acres provide for good privacy with reasonable road frontage and an excellent habitat lending an upper hand for Deer, Turkey and other diverse wildlife species. The convenience of this wooded parcel is another reason to move it to the top of your list at around 20 minutes to Middletown Delaware and close to numerous acres of state held land. The current owner has not performed a perc test but there are a few other homes adjoining the property to the east on similar soil types and elevations. As always, any buyer should perform their own due diligence, any map boundary lines are only estimates.

Bradford Johnson Road, Golts

Listing courtesy of The Land Group. Contact:

Selling Office: National Land Realty, LLC.

$395,000

Beautifully updated and maintained Colonial home in Dogwood Village. This spacious home offers nearly 2000 square feet of living plus a basement area. There is an attached 2 car garage and both a screened porch and open deck at the rear of the home. A fireplace in the living room adds warmth to cool fall and winter days. The rear of the home is accented by both spacious screened porch and an open deck. Perfect location with easy access to highways and tax free shopping in Middletown.

Beautifully updated and maintained Colonial home in Dogwood Village. This spacious home offers nearly 2000 square feet of living plus a basement area. There is an attached 2 car garage and both a screened porch and open deck at the rear of the home. A fireplace in the living room adds warmth to cool fall and winter days. The rear of the home is accented by both spacious screened porch and an open deck. Perfect location with easy access to highways and tax free shopping in Middletown.

189 Birchwood, Galena

Listing courtesy of L. C. Parker Real Estate. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$395,000

10790 Worton Rd shows very well, starting with a covered front porch with plenty of room for comfortable seating. This rancher home has a split-type floor plan, with a large primary suite featuring a nice step in shower, plenty of space for a king-size bed and still room for a relaxing reading area. The living space is open to the kitchen, living room, sitting room, or it could be a dining area which features a gas fireplace. There is also a door leading to the fenced in back yard, so your treasured pet will be safe. All the necessary appliances convey. There is a handy island for casual eating in the kitchen. Plenty of storage with a pantry closet as well. Laundry room is conveniently off of the kitchen area with access to the side yard. Plenty of storage with a pantry closet as well. No basement but the 2 car detached garage has plenty of storage with an area dedicated to a pool table. There are three bedrooms in all, with another hall bath. Included in this sale is an additional parcel (see documents) that has a milk house that was built somewhere around the 1930's. The zoning for the 2nd parcel is C1. The milk house is being sold as is. With the additional parcel being conveyed the total acreage is +/- 1.353 This is a property is a bit tucked away but still located close to Chestertown for convenience.

10790 Worton Rd shows very well, starting with a covered front porch with plenty of room for comfortable seating. This rancher home has a split-type floor plan, with a large primary suite featuring a nice step in shower, plenty of space for a king-size bed and still room for a relaxing reading area. The living space is open to the kitchen, living room, sitting room, or it could be a dining area which features a gas fireplace. There is also a door leading to the fenced in back yard, so your treasured pet will be safe. All the necessary appliances convey. There is a handy island for casual eating in the kitchen. Plenty of storage with a pantry closet as well. Laundry room is conveniently off of the kitchen area with access to the side yard. Plenty of storage with a pantry closet as well. No basement but the 2 car detached garage has plenty of storage with an area dedicated to a pool table. There are three bedrooms in all, with another hall bath. Included in this sale is an additional parcel (see documents) that has a milk house that was built somewhere around the 1930's. The zoning for the 2nd parcel is C1. The milk house is being sold as is. With the additional parcel being conveyed the total acreage is +/- 1.353 This is a property is a bit tucked away but still located close to Chestertown for convenience.

10790 Worton Rd, Worton

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Doug Ashley Realtors, LLC.

$395,000

Well maintained Beautiful Brick Rancher nestled on 2.16 Acres in Chestertown and a short distance to Historic Downtown. 3 Spacious Bedrooms all with Hardwood Flooring and 2 Full Baths. The Primary Bath has been completely renovated with a Walk-In Tiled Shower. Living Room offering a cozy Brick Fireplace with Hardwood Flooring. Family/Kitchen Combo with Slider leading to the tranquil back yard. Enjoy the 20x40 in-ground Pool (new cover) which is great for Family Fun and Entertaining. Oversized attached 2 car Garage with ample driveway parking for guests and storage. Amazing Home updates include New Roof 2009, Windows 2018, Heat Pump 2022, Septic 2019, Well 2022. Great opportunity to own a charming home! 1 Year Home Warranty Included

Well maintained Beautiful Brick Rancher nestled on 2.16 Acres in Chestertown and a short distance to Historic Downtown. 3 Spacious Bedrooms all with Hardwood Flooring and 2 Full Baths. The Primary Bath has been completely renovated with a Walk-In Tiled Shower. Living Room offering a cozy Brick Fireplace with Hardwood Flooring. Family/Kitchen Combo with Slider leading to the tranquil back yard. Enjoy the 20x40 in-ground Pool (new cover) which is great for Family Fun and Entertaining. Oversized attached 2 car Garage with ample driveway parking for guests and storage. Amazing Home updates include New Roof 2009, Windows 2018, Heat Pump 2022, Septic 2019, Well 2022. Great opportunity to own a charming home! 1 Year Home Warranty Included

8629 Airy Hill Rd, Chestertown

Listing courtesy of Keller Williams Realty. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$394,000

Looking for NEW construction and the convenience of one-story living? Look No Further! At the end of a private driveway is this elegantly designed 3 BR 2 bath Country Craftsman nestled on a 0.25 acre lot. A multi pitched roofline tops this beautiful home which displays craftsmanship and attention to detail. This oasis which has a keyless entry two-car attached garage is adorned with board and batten siding and very stylish black gutters and downspouts. The front porch offers relaxation in a private setting. Step inside and you will be greeted with a well-designed open floor layout. This home welcomes you with beautiful LVP flooring, recessed lighting, 10’ ceiling in the living area, modern kitchen with SS appliances, under cabinet lighting, granite countertops along with a sprinkler system throughout. This split bedroom layout is flanked with a primary bedroom 14’ x 12’ on the right side situated behind the double garage. The ensuite has a stand alone tiled shower, double vanity, and spacious walk-in closet. A few steps from the primary bedroom is the laundry/utility/mud room. On the left side of this home are two other bedrooms both 11’ 4” x 11’. Each have a walk-in closet. A shared bathroom between these two bedrooms has a linen closet, and a tiled to ceiling soaker tub. In this hallway is another linen closet. No shortage of storage in this home. In the attached garage you have an EV charger, a storage room, and additional attic storage overhead. As you exit from the kitchen, there is a landing with stairs that lead to a cement pad in the backyard. This outside area is a great place to host family and friends gatherings along with other outdoor activities. A bonus to this home is the one-car detached garage at the end of the lane. A great place for that “man cave”, “she shed”, playhouse, workshop, or storage. Easy commute to Routes 301 and 50. Conveniently located near the high school and community center. Outdoor attractions include Betterton beach, Chesapeake shores of Rock Hall, great local restaurants. Schedule your showings today!

Looking for NEW construction and the convenience of one-story living? Look No Further! At the end of a private driveway is this elegantly designed 3 BR 2 bath Country Craftsman nestled on a 0.25 acre lot. A multi pitched roofline tops this beautiful home which displays craftsmanship and attention to detail. This oasis which has a keyless entry two-car attached garage is adorned with board and batten siding and very stylish black gutters and downspouts. The front porch offers relaxation in a private setting. Step inside and you will be greeted with a well-designed open floor layout. This home welcomes you with beautiful LVP flooring, recessed lighting, 10’ ceiling in the living area, modern kitchen with SS appliances, under cabinet lighting, granite countertops along with a sprinkler system throughout. This split bedroom layout is flanked with a primary bedroom 14’ x 12’ on the right side situated behind the double garage. The ensuite has a stand alone tiled shower, double vanity, and spacious walk-in closet. A few steps from the primary bedroom is the laundry/utility/mud room. On the left side of this home are two other bedrooms both 11’ 4” x 11’. Each have a walk-in closet. A shared bathroom between these two bedrooms has a linen closet, and a tiled to ceiling soaker tub. In this hallway is another linen closet. No shortage of storage in this home. In the attached garage you have an EV charger, a storage room, and additional attic storage overhead. As you exit from the kitchen, there is a landing with stairs that lead to a cement pad in the backyard. This outside area is a great place to host family and friends gatherings along with other outdoor activities. A bonus to this home is the one-car detached garage at the end of the lane. A great place for that “man cave”, “she shed”, playhouse, workshop, or storage. Easy commute to Routes 301 and 50. Conveniently located near the high school and community center. Outdoor attractions include Betterton beach, Chesapeake shores of Rock Hall, great local restaurants. Schedule your showings today!

25070 Lambs Meadow Rd, Worton

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: EXP Realty, LLC.

$391,000

OPEN HOUSE, SATURDAY, NOV 1, 10-12 PM! 100% financing is available! The seller offers up to $10,000 toward closing costs or a rate buy down. This brand new home in Rock Hall, a historic harbor town celebrated for its Chesapeake Bay shoreline, boating lifestyle and vibrant coastal charm, features 4 bedrooms, 2 bathrooms and 2,000 square feet of single-level living. It offers luxury vinyl floors, energy efficient windows, a spacious central island with seating, stainless steel appliances, a large porch for entertaining and an attached 1 car garage. Situated on a quarter-acre lot in a new cul de sac, the property balances privacy and community. You will be minutes from downtown Rock Hall, where you can enjoy fresh seafood, explore museums and experience the charm of this Eastern Shore town. Whether strolling along the waterfront, enjoying the marina or setting sail on the Bay, this home puts you at the heart of it all. Discover Eastern Shore living where modern comfort meets small town character and arrange your private showing today.

4 Beds ⋅ 2 Baths

OPEN HOUSE, SATURDAY, NOV 1, 10-12 PM! 100% financing is available! The seller offers up to $10,000 toward closing costs or a rate buy down. This brand new home in Rock Hall, a historic harbor town celebrated for its Chesapeake Bay shoreline, boating lifestyle and vibrant coastal charm, features 4 bedrooms, 2 bathrooms and 2,000 square feet of single-level living. It offers luxury vinyl floors, energy efficient windows, a spacious central island with seating, stainless steel appliances, a large porch for entertaining and an attached 1 car garage. Situated on a quarter-acre lot in a new cul de sac, the property balances privacy and community. You will be minutes from downtown Rock Hall, where you can enjoy fresh seafood, explore museums and experience the charm of this Eastern Shore town. Whether strolling along the waterfront, enjoying the marina or setting sail on the Bay, this home puts you at the heart of it all. Discover Eastern Shore living where modern comfort meets small town character and arrange your private showing today.

21739 Centennial Ln, Rock Hall

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: Maverick Realty, LLC.

$390,000

Welcome home to 7982 Radcliffe Road! This charming corner-lot offers a perfect blend of character and modern comfort. Built in 1978- this well maintained 2 bedroom, 2 bathroom home feels more of a newer era. Inside you'll find a spacious living room with plenty of room to relax by the fireplace or entertain! The oversized garage offers amazing storage and features an office space that is closed off. Outside, you can enjoy the nice-sized yard with the views of a crop field and beautiful sunsets. Located right outside of Chestertown, the home puts shops, restaurants, and the local farmers market close by and is also walking distance to a view of the Chester River! An amazing opportunity to enjoy small-town living convenience, space & character!

2 Beds ⋅ 2 Baths

Welcome home to 7982 Radcliffe Road! This charming corner-lot offers a perfect blend of character and modern comfort. Built in 1978- this well maintained 2 bedroom, 2 bathroom home feels more of a newer era. Inside you'll find a spacious living room with plenty of room to relax by the fireplace or entertain! The oversized garage offers amazing storage and features an office space that is closed off. Outside, you can enjoy the nice-sized yard with the views of a crop field and beautiful sunsets. Located right outside of Chestertown, the home puts shops, restaurants, and the local farmers market close by and is also walking distance to a view of the Chester River! An amazing opportunity to enjoy small-town living convenience, space & character!

7982 Radcliffe Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

$390,000

Just off Route 301 for commuters, but located in the country with privacy, space for animals, hobbies, and entertaining. Large detached garage with storage space above, full unfinished basement, fenced pasture area, and inground pool. So much potential here, come with vision and make it your own!

4 Beds ⋅ 2 Baths

Just off Route 301 for commuters, but located in the country with privacy, space for animals, hobbies, and entertaining. Large detached garage with storage space above, full unfinished basement, fenced pasture area, and inground pool. So much potential here, come with vision and make it your own!

32287 Quinn Rd, Massey

Listing courtesy of Village Real Estate Company LLC. Contact:

Selling Office: Coldwell Banker Rowley Realtors.

$385,000

Enjoy your own private waterfront access with a dock perfect for launching a canoe, kayak, or paddleboard. While the water at the dock is not deep enough for larger boats, deep-water access is just minutes away at Long Cove Marina or the nearby Long Cove public landing. The property consists of two deeded parcels, offering the potential to obtain a second sewer allocation for the adjoining 1+ acre lot (buyer to verify with Kent County Planning & Zoning). Those looking to renovate will appreciate that the existing home is located outside the 100-foot Critical Area buffer, making future improvements more feasible. Relax on the deck and take in the peaceful surroundings, where blue herons, bald eagles, deer, and other wildlife are frequent visitors. One of the area's oldest and largest bald eagle nests can be seen just across the creek, adding to the property's truly special setting. Whether you're dreaming of restoring the existing home, building for the future, or simply enjoying the tranquility of this unique waterfront escape, the possibilities are endless. Please note: When visiting the property, drive all the way into the driveway and do not park or turn around on neighboring properties.

Enjoy your own private waterfront access with a dock perfect for launching a canoe, kayak, or paddleboard. While the water at the dock is not deep enough for larger boats, deep-water access is just minutes away at Long Cove Marina or the nearby Long Cove public landing. The property consists of two deeded parcels, offering the potential to obtain a second sewer allocation for the adjoining 1+ acre lot (buyer to verify with Kent County Planning & Zoning). Those looking to renovate will appreciate that the existing home is located outside the 100-foot Critical Area buffer, making future improvements more feasible. Relax on the deck and take in the peaceful surroundings, where blue herons, bald eagles, deer, and other wildlife are frequent visitors. One of the area's oldest and largest bald eagle nests can be seen just across the creek, adding to the property's truly special setting. Whether you're dreaming of restoring the existing home, building for the future, or simply enjoying the tranquility of this unique waterfront escape, the possibilities are endless. Please note: When visiting the property, drive all the way into the driveway and do not park or turn around on neighboring properties.

22523 Crouchs Ln, Rock Hall

Listing courtesy of Select Land & Homes, LLC. Contact:

Selling Office: Crown Homes Real Estate.

$385,000

Welcome to 107 Boxwood Lane in the Dogwood Village community. This home is nicely situated at the end of a cul-de-sac with a spacious triangular lot. The backyard is nicely edged with foliage, making a private oasis. The home offers convenient one-floor living. Large open living space, stainless steel appliances, wood floors and natural light. A bonus sunroom is just steps away from the dining area. This space could also be a playroom, studio, office or den. The primary bedroom has a large bathroom and walk-in closet. Two additional bedrooms share a full bathroom. Spacious two car garage and large paved driveway. From the garage there is a walk-down basement for additional storage or projects. A short drive to the Sassafras River and many marinas. Located 30 minutes from Chestertown and Middletown DE, under an hour to Wilmington.

Welcome to 107 Boxwood Lane in the Dogwood Village community. This home is nicely situated at the end of a cul-de-sac with a spacious triangular lot. The backyard is nicely edged with foliage, making a private oasis. The home offers convenient one-floor living. Large open living space, stainless steel appliances, wood floors and natural light. A bonus sunroom is just steps away from the dining area. This space could also be a playroom, studio, office or den. The primary bedroom has a large bathroom and walk-in closet. Two additional bedrooms share a full bathroom. Spacious two car garage and large paved driveway. From the garage there is a walk-down basement for additional storage or projects. A short drive to the Sassafras River and many marinas. Located 30 minutes from Chestertown and Middletown DE, under an hour to Wilmington.

107 Boxwood Ln, Galena

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Remax Vision.

$384,000

Custom-Perfected Home with Luxury Finishes — Without the Luxury Price This beautifully reimagined 3-bedroom, 2-bath home (1,512 sq. ft.) sits on a generous .34-acre lot and offers high-end upgrades you’d expect to find in a designer showcase. The owners completely overhauled the home from top to bottom—correcting builder issues and enhancing every detail with thoughtful, custom touches. Step inside to discover modern farmhouse elegance, highlighted by a stunning chef’s kitchen where no detail was spared. From porcelain wood-look tile floors to solid wood KraftMaid soft-close cabinetry, quartz countertops, and a massive island, this kitchen is both functional and fabulous. You’ll love the hidden microwave, gold fixtures, pot filler, double Café dishwashers, Café refrigerator with Keurig dispenser, and brick tile backsplash—plus clever add-ons like concealed charging stations, pop-up countertop shelves, and pull-out drawers for effortless organization. The open living area features a custom shiplap accent wall, a cozy pellet stove, and custom steel handrails leading upstairs. There’s a bedroom and full bath on the first floor—perfect for guests or multigenerational living. Upstairs offers two additional bedrooms and a beautifully updated bath. Outside, your private paradise awaits. The backyard is partially enclosed with a 6-ft privacy fence, surrounded by raised garden beds (with tomatoes already growing!), a water-fed garden line, French drains for excellent drainage, and a concrete patio complete with hot tub, privacy pergola with curtains, outdoor TV, and lighting for evening entertaining. The impressive Amish-built 24x30 garage is more than just parking—it’s a dream workshop, featuring a 4-inch poured concrete pad with reinforced supports, mini-split HVAC, pellet stove, LED lighting, garage door opener, RV hook-up, and EV charging outlet. Additional upgrades include fresh interior paint, brick tile floors in the downstairs bath, custom window treatments on the back sliding door, and a recently completed septic and home inspection for peace of mind. Located in a community with optional HOA membership that grants access to water amenities. Enjoy easy proximity to Great Oak Marina—featuring a restaurant, beach bar, and live entertainment—plus charming Chestertown and Rock Hall, both just 12 minutes away. This is more than a home—it’s a showcase of craftsmanship, comfort, and creativity, all wrapped in affordability. You truly have to see it to believe it! Want to see these updated fun features in action, there is a video to show just that!

Custom-Perfected Home with Luxury Finishes — Without the Luxury Price This beautifully reimagined 3-bedroom, 2-bath home (1,512 sq. ft.) sits on a generous .34-acre lot and offers high-end upgrades you’d expect to find in a designer showcase. The owners completely overhauled the home from top to bottom—correcting builder issues and enhancing every detail with thoughtful, custom touches. Step inside to discover modern farmhouse elegance, highlighted by a stunning chef’s kitchen where no detail was spared. From porcelain wood-look tile floors to solid wood KraftMaid soft-close cabinetry, quartz countertops, and a massive island, this kitchen is both functional and fabulous. You’ll love the hidden microwave, gold fixtures, pot filler, double Café dishwashers, Café refrigerator with Keurig dispenser, and brick tile backsplash—plus clever add-ons like concealed charging stations, pop-up countertop shelves, and pull-out drawers for effortless organization. The open living area features a custom shiplap accent wall, a cozy pellet stove, and custom steel handrails leading upstairs. There’s a bedroom and full bath on the first floor—perfect for guests or multigenerational living. Upstairs offers two additional bedrooms and a beautifully updated bath. Outside, your private paradise awaits. The backyard is partially enclosed with a 6-ft privacy fence, surrounded by raised garden beds (with tomatoes already growing!), a water-fed garden line, French drains for excellent drainage, and a concrete patio complete with hot tub, privacy pergola with curtains, outdoor TV, and lighting for evening entertaining. The impressive Amish-built 24x30 garage is more than just parking—it’s a dream workshop, featuring a 4-inch poured concrete pad with reinforced supports, mini-split HVAC, pellet stove, LED lighting, garage door opener, RV hook-up, and EV charging outlet. Additional upgrades include fresh interior paint, brick tile floors in the downstairs bath, custom window treatments on the back sliding door, and a recently completed septic and home inspection for peace of mind. Located in a community with optional HOA membership that grants access to water amenities. Enjoy easy proximity to Great Oak Marina—featuring a restaurant, beach bar, and live entertainment—plus charming Chestertown and Rock Hall, both just 12 minutes away. This is more than a home—it’s a showcase of craftsmanship, comfort, and creativity, all wrapped in affordability. You truly have to see it to believe it! Want to see these updated fun features in action, there is a video to show just that!

23416 Cloquet Rd, Chestertown

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

Selling Office: Compass.

$382,500

Buyer's remorse means this house is again available at an amazing price! Spacious home in Kenndyville with lots of amenities. Featuring 4 bedrooms and 2.5 baths with a large kitchen with granite countertops, living room with gas fireplace, 2-car detached garage, and a huge unfinished basement. Plenty of storage. Deck off the living room leads to a partially fenced back yard. Just a short drive to downtown Chestertown.

Buyer's remorse means this house is again available at an amazing price! Spacious home in Kenndyville with lots of amenities. Featuring 4 bedrooms and 2.5 baths with a large kitchen with granite countertops, living room with gas fireplace, 2-car detached garage, and a huge unfinished basement. Plenty of storage. Deck off the living room leads to a partially fenced back yard. Just a short drive to downtown Chestertown.

11901 Dairy St, Kennedyville

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

Selling Office: Benson & Mangold, LLC.

$380,000

NEW PRICE – One of Chestertown's Best Values! Over 2,500 square feet of 2023 construction priced comparably to many older Chestertown homes with just 1,200–1,800 square feet. If you're looking for maximum living space, modern design, and exceptional value, this home deserves a closer look. This move-in ready, three-story home offers 5 bedrooms, 3.5 baths, and 2,535 square feet of thoughtfully designed living space. The inviting front porch welcomes you into an open-concept main level featuring a spacious family room, dining area, and a bright kitchen designed for everyday living and entertaining. Highlights include stainless steel appliances, a generous peninsula, large corner pantry, first-floor laundry, and convenient powder room. The private owner's suite features a spacious walk-in closet and en-suite bath with double vanity and walk-in shower. Three additional bedrooms share a full bath with double vanity, while the finished third level provides a fifth bedroom, full bath, and flexible bonus space perfect for a home office, media room, playroom, fitness area, or guest suite. Ample closet space throughout provides exceptional storage. Unlike many homes in the community, this property backs to mature trees rather than neighboring homes, offering a more private backyard setting. Additional features include a modern Smart Home Package for convenience, efficiency, and peace of mind. Seller is offering a buyer credit toward allowable closing costs, helping conserve cash after settlement for future backyard enhancements such as a patio, fencing, or shed. Enjoy the beautifully landscaped community pond with fountain and the convenience of being just minutes from historic downtown Chestertown, Washington College, waterfront parks, restaurants, shopping, and year-round community events. The Village of Chestertown is now a completed community with no future construction—offering the opportunity to enjoy an established neighborhood from day one. Compare the square footage, age, and features, then come see why this home represents one of the best values currently available in the Chestertown market.

5 Beds ⋅ 4 Baths

NEW PRICE – One of Chestertown's Best Values! Over 2,500 square feet of 2023 construction priced comparably to many older Chestertown homes with just 1,200–1,800 square feet. If you're looking for maximum living space, modern design, and exceptional value, this home deserves a closer look. This move-in ready, three-story home offers 5 bedrooms, 3.5 baths, and 2,535 square feet of thoughtfully designed living space. The inviting front porch welcomes you into an open-concept main level featuring a spacious family room, dining area, and a bright kitchen designed for everyday living and entertaining. Highlights include stainless steel appliances, a generous peninsula, large corner pantry, first-floor laundry, and convenient powder room. The private owner's suite features a spacious walk-in closet and en-suite bath with double vanity and walk-in shower. Three additional bedrooms share a full bath with double vanity, while the finished third level provides a fifth bedroom, full bath, and flexible bonus space perfect for a home office, media room, playroom, fitness area, or guest suite. Ample closet space throughout provides exceptional storage. Unlike many homes in the community, this property backs to mature trees rather than neighboring homes, offering a more private backyard setting. Additional features include a modern Smart Home Package for convenience, efficiency, and peace of mind. Seller is offering a buyer credit toward allowable closing costs, helping conserve cash after settlement for future backyard enhancements such as a patio, fencing, or shed. Enjoy the beautifully landscaped community pond with fountain and the convenience of being just minutes from historic downtown Chestertown, Washington College, waterfront parks, restaurants, shopping, and year-round community events. The Village of Chestertown is now a completed community with no future construction—offering the opportunity to enjoy an established neighborhood from day one. Compare the square footage, age, and features, then come see why this home represents one of the best values currently available in the Chestertown market.

107 Flying Cloud Dr, Chestertown

Listing courtesy of CENTURY 21 New Millennium. Contact:

Selling Office: RE/MAX Advantage Realty.

$380,000

Welcome to this Hidden Gem on 1.11 Acres! Just minutes from Rt. 301, this property offers the perfect blend of peaceful rural charm and convenient access to Middletown, Dover, and Chestertown. This custom-built, one-level home features energy-efficient 2x6 construction, a partially open floor plan, 3 bedrooms, and 2 full bathrooms—providing comfortable single-story living for the whole family. Inside, enjoy the warm, rustic feel of beautiful Scotch Pine wood imported from Finland, showcased on the walls and vaulted ceiling. A new Pelpro pellet stove adds cozy cabin ambience and efficient heating during cooler months. Recent upgrades include: Metal roof (5 years new), New front door, LVP flooring, New hot water heater, New stove & dishwasher, New shutters, New pool pump, Fresh landscaping, and a Fully encapsulated crawl space with dehumidifier for added peace of mind. Outdoor Living You’ll Love: Step outside to your expansive, private backyard retreat. Relax on the large covered deck, cool off in the above-ground saltwater pool (2018), or unwind year-round in the 6-person Vita Spa hot tub (2018). A True Workshop Dream: The standout feature of this property is the fully insulated, air-conditioned 24' x 32' shop/garage, equipped with: 100-amp electric service, 2-post vehicle lift, 220-volt welding receptacle, Small rear office—ideal for hobbyists or working from home. Perfect for mechanics, welders, or anyone needing space for trucks, boats, or equipment. Additional structures include an 18' x 20' lean-to with metal roof and a 40-ft shipping container for secure storage. Come tour this unique home and make your dreams a reality today!

Welcome to this Hidden Gem on 1.11 Acres! Just minutes from Rt. 301, this property offers the perfect blend of peaceful rural charm and convenient access to Middletown, Dover, and Chestertown. This custom-built, one-level home features energy-efficient 2x6 construction, a partially open floor plan, 3 bedrooms, and 2 full bathrooms—providing comfortable single-story living for the whole family. Inside, enjoy the warm, rustic feel of beautiful Scotch Pine wood imported from Finland, showcased on the walls and vaulted ceiling. A new Pelpro pellet stove adds cozy cabin ambience and efficient heating during cooler months. Recent upgrades include: Metal roof (5 years new), New front door, LVP flooring, New hot water heater, New stove & dishwasher, New shutters, New pool pump, Fresh landscaping, and a Fully encapsulated crawl space with dehumidifier for added peace of mind. Outdoor Living You’ll Love: Step outside to your expansive, private backyard retreat. Relax on the large covered deck, cool off in the above-ground saltwater pool (2018), or unwind year-round in the 6-person Vita Spa hot tub (2018). A True Workshop Dream: The standout feature of this property is the fully insulated, air-conditioned 24' x 32' shop/garage, equipped with: 100-amp electric service, 2-post vehicle lift, 220-volt welding receptacle, Small rear office—ideal for hobbyists or working from home. Perfect for mechanics, welders, or anyone needing space for trucks, boats, or equipment. Additional structures include an 18' x 20' lean-to with metal roof and a 40-ft shipping container for secure storage. Come tour this unique home and make your dreams a reality today!

12035 Galena Rd, Massey

Listing courtesy of Taylor Properties. Contact:

Selling Office: Berkshire Hathaway HomeServices Homesale Realty.

$379,900

Welcome to this stunning 2023 built home — a move-in ready, three-story residence offering 5 bedrooms and 3.5 baths across 2,615 sq ft of thoughtfully designed space. The first floor features an open layout with a spacious family room, dining area, and bright, well-appointed kitchen. This level also includes a convenient first-floor laundry and a powder room. The kitchen is equipped with stainless appliances, a large corner pantry, and a generous peninsula. Upstairs, the owner’s suite offers a walk-in closet and an en-suite bath with a double vanity and walk-in shower. Three additional bedrooms share a full hall bath, also with a double vanity for added convenience. The third floor provides the fifth bedroom, another full bath, and a flexible space ideal for an office, playroom, media room or storage. Extras you’ll love: modern smart features, a fully fenced yard, and a backyard upgraded with pavers and a concrete patio, perfect for grilling, entertaining, or relaxing outdoors. Plenty of closets and storage space. With everything already complete, this home blends comfort, convenience, and style.

5 Beds ⋅ 4 Baths

Welcome to this stunning 2023 built home — a move-in ready, three-story residence offering 5 bedrooms and 3.5 baths across 2,615 sq ft of thoughtfully designed space. The first floor features an open layout with a spacious family room, dining area, and bright, well-appointed kitchen. This level also includes a convenient first-floor laundry and a powder room. The kitchen is equipped with stainless appliances, a large corner pantry, and a generous peninsula. Upstairs, the owner’s suite offers a walk-in closet and an en-suite bath with a double vanity and walk-in shower. Three additional bedrooms share a full hall bath, also with a double vanity for added convenience. The third floor provides the fifth bedroom, another full bath, and a flexible space ideal for an office, playroom, media room or storage. Extras you’ll love: modern smart features, a fully fenced yard, and a backyard upgraded with pavers and a concrete patio, perfect for grilling, entertaining, or relaxing outdoors. Plenty of closets and storage space. With everything already complete, this home blends comfort, convenience, and style.

112 Silver Heel Dr, Chestertown

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: Crown Homes Real Estate.

$376,900

Back on the market due to the previous buyer's financing denial. A home inspection was completed, and the seller has addressed all requested repairs. The inspection report and receipts for completed repairs are available upon request, providing added confidence for prospective buyers. Welcome to this beautifully updated 4-bedroom, 3 full bath home situated on a spacious 1.68-acre corner lot in a peaceful rural setting. This move-in-ready property features a renovated kitchen with modern finishes, updated bathrooms, new paint, new flooring, and a new water well. The partially finished basement with bar offers additional living and entertaining space perfect for gatherings or relaxing. Enjoy the perfect balance of privacy and convenience with easy access to Middletown, DE, Chestertown, and Dover. Plenty of outdoor space for entertaining, gardening, or simply enjoying Eastern Shore living. Don’t miss this opportunity to own a beautifully renovated home in a convenient location. This property won’t last long; schedule your appointment today! " Listing agent is related to seller"

Back on the market due to the previous buyer's financing denial. A home inspection was completed, and the seller has addressed all requested repairs. The inspection report and receipts for completed repairs are available upon request, providing added confidence for prospective buyers. Welcome to this beautifully updated 4-bedroom, 3 full bath home situated on a spacious 1.68-acre corner lot in a peaceful rural setting. This move-in-ready property features a renovated kitchen with modern finishes, updated bathrooms, new paint, new flooring, and a new water well. The partially finished basement with bar offers additional living and entertaining space perfect for gatherings or relaxing. Enjoy the perfect balance of privacy and convenience with easy access to Middletown, DE, Chestertown, and Dover. Plenty of outdoor space for entertaining, gardening, or simply enjoying Eastern Shore living. Don’t miss this opportunity to own a beautifully renovated home in a convenient location. This property won’t last long; schedule your appointment today! " Listing agent is related to seller"

31657 Olivet Cir, Galena

Listing courtesy of Keller Williams Realty Central-Delaware. Contact:

Selling Office: Crown Homes Real Estate.

$375,000

Welcome to 14037 E. Beechwood Road- set on a spacious, nearly one-acre lot, this property offers privacy, scenic views, and the kind of laid-back lifestyle the Eastern Shore is known for. Enjoy the beauty of rural surroundings with plenty of room for outdoor living, gardening or simply relaxing and taking in the natural landscape. Inside, the move-in ready home features three comfortable bedrooms and two full baths, offering a functional layout for everyday living. The nicely sized kitchen includes ample cabinetry and an eat-in area, providing a welcoming space for meals and gathering. Downstairs there is a bonus space that can be used for additional living area, home gym or an office. Step outside and you'll find a large rear covered porch- perfect for enjoying morning coffee or unwinding in the evenings- along with a paver patio that extends the outdoor living and entertaining space. The community of Gregg Neck is known for its quiet roads, larger parcels, and relaxed pace- offering that sought-after Eastern Shore vibe while still being conveniently located to nearby towns, shopping and major routes for commuting ease.

Welcome to 14037 E. Beechwood Road- set on a spacious, nearly one-acre lot, this property offers privacy, scenic views, and the kind of laid-back lifestyle the Eastern Shore is known for. Enjoy the beauty of rural surroundings with plenty of room for outdoor living, gardening or simply relaxing and taking in the natural landscape. Inside, the move-in ready home features three comfortable bedrooms and two full baths, offering a functional layout for everyday living. The nicely sized kitchen includes ample cabinetry and an eat-in area, providing a welcoming space for meals and gathering. Downstairs there is a bonus space that can be used for additional living area, home gym or an office. Step outside and you'll find a large rear covered porch- perfect for enjoying morning coffee or unwinding in the evenings- along with a paver patio that extends the outdoor living and entertaining space. The community of Gregg Neck is known for its quiet roads, larger parcels, and relaxed pace- offering that sought-after Eastern Shore vibe while still being conveniently located to nearby towns, shopping and major routes for commuting ease.

14037 E Beechwood Rd, Galena

Listing courtesy of CR Realty. Contact:

Selling Office: EXIT Preferred Realty.

$375,000

Recently and thoroughly renovated, charming and spacious 4 bedroom 3 bathroom home located only about 6 miles from Chestertown in an idyllic country setting. Some improvements include new HVAC, electric, 3 season room , water filter and high-end, smart appliances. Terrific in-ground pool enclosed with privacy brick wall, a large patio and deck are perfect for entertaining or relaxing in the outdoors. Oversized (26x36) detached 2-car garage with additional storage space/workshop (12x24) and electric. Situated on approximately 1 acre lot with peaceful, park-like setting and mature trees. Priced below replacement cost. Schedule a showing today.

Recently and thoroughly renovated, charming and spacious 4 bedroom 3 bathroom home located only about 6 miles from Chestertown in an idyllic country setting. Some improvements include new HVAC, electric, 3 season room , water filter and high-end, smart appliances. Terrific in-ground pool enclosed with privacy brick wall, a large patio and deck are perfect for entertaining or relaxing in the outdoors. Oversized (26x36) detached 2-car garage with additional storage space/workshop (12x24) and electric. Situated on approximately 1 acre lot with peaceful, park-like setting and mature trees. Priced below replacement cost. Schedule a showing today.

7653 Broad Neck Rd, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Pearson Smith Realty, LLC.

$375,000

JUST INSTALLED BRAND NEW CARPET! Welcome to 907 N Meadowview Drive, a beautifully maintained home in the sought-after Crestview community of Chestertown. Situated on a spacious .707-acre lot, this 3-bedroom, 2.5-bath home offers 1,842 square feet of comfortable living space. Step inside to find a bright and inviting living room anchored by a cozy pellet stove, ideal for chilly evenings. The eat-in kitchen provides plenty of space for casual dining, while the formal dining room offers flexibility—use it as a traditional dining area, home office, or playroom to suit your lifestyle. All three bedrooms are located on the second level, along with two full bathrooms. A convenient half bath is located just off the main living area, and a dedicated laundry room adds to the home’s practical layout. The attached two-car garage offers additional storage and convenience. Enjoy the outdoors with a private back deck, patio area, and two large side yards surrounded by beautiful landscaping—ideal for entertaining, gardening, or simply unwinding after a long day. Don’t miss your opportunity to own a well-cared-for home on a generously sized lot in a lovely neighborhood just minutes from downtown Chestertown.

JUST INSTALLED BRAND NEW CARPET! Welcome to 907 N Meadowview Drive, a beautifully maintained home in the sought-after Crestview community of Chestertown. Situated on a spacious .707-acre lot, this 3-bedroom, 2.5-bath home offers 1,842 square feet of comfortable living space. Step inside to find a bright and inviting living room anchored by a cozy pellet stove, ideal for chilly evenings. The eat-in kitchen provides plenty of space for casual dining, while the formal dining room offers flexibility—use it as a traditional dining area, home office, or playroom to suit your lifestyle. All three bedrooms are located on the second level, along with two full bathrooms. A convenient half bath is located just off the main living area, and a dedicated laundry room adds to the home’s practical layout. The attached two-car garage offers additional storage and convenience. Enjoy the outdoors with a private back deck, patio area, and two large side yards surrounded by beautiful landscaping—ideal for entertaining, gardening, or simply unwinding after a long day. Don’t miss your opportunity to own a well-cared-for home on a generously sized lot in a lovely neighborhood just minutes from downtown Chestertown.

907 N Meadowview Dr, Chestertown

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

Selling Office: Cross Street Realtors LLC.

Nestled in the northernmost part of Kent County, this charming Galena home offers the perfect blend of small-town living and convenient access to nearby destinations. Enjoy an easy commute to Middletown, Delaware, Cecil County, and Chestertown, while being just minutes from local marinas, waterfront restaurants, and all the recreation the area has to offer. The beautiful Sassafras River is less than a mile away, providing stunning views, boating opportunities, and waterfront dining. Inside, you'll find new flooring, fresh paint throughout, and a bright, refreshed interior that is truly move-in ready. The full unfinished basement offers abundant storage space and endless possibilities for a workshop, hobby area, home gym, or future expansion.

Nestled in the northernmost part of Kent County, this charming Galena home offers the perfect blend of small-town living and convenient access to nearby destinations. Enjoy an easy commute to Middletown, Delaware, Cecil County, and Chestertown, while being just minutes from local marinas, waterfront restaurants, and all the recreation the area has to offer. The beautiful Sassafras River is less than a mile away, providing stunning views, boating opportunities, and waterfront dining. Inside, you'll find new flooring, fresh paint throughout, and a bright, refreshed interior that is truly move-in ready. The full unfinished basement offers abundant storage space and endless possibilities for a workshop, hobby area, home gym, or future expansion.

105 Dogwood Dr, Galena

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

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

Beautifully updated and move-in ready, this charming one-level home offers the perfect blend of comfort, style, and convenience! Recent improvements include a newly added full bath off the living area and a beautifully remodeled half bath featuring a gorgeous walk-in shower and all new finishes The inviting kitchen includes an eat-in dining area, breakfast bar, wine cooler, and brand-new appliances -- ideal for entertaining or everyday living. Gorgeous hardwood floors and attractive tilework throughout add warmth and character. Relax on the enclosed side porch with peaceful neighborhood views or enjoy outdoor living on the newly build deck designed for sunny afternoons and evening gatherings. Located in the heart of Rock Hall, this home places you close to marinas, public landings, local shops, restaurants, and all the charm this beloved Chesapeake Bay town has to offer. Enjoy seasonal festivities, waterfront living, and the laid-back lifestyle Eastern Shore buyers love. Whether you are looking for a full-time residence, weekend getaway or retirement retreat, this lovely home truly feels like HOME!

Beautifully updated and move-in ready, this charming one-level home offers the perfect blend of comfort, style, and convenience! Recent improvements include a newly added full bath off the living area and a beautifully remodeled half bath featuring a gorgeous walk-in shower and all new finishes The inviting kitchen includes an eat-in dining area, breakfast bar, wine cooler, and brand-new appliances -- ideal for entertaining or everyday living. Gorgeous hardwood floors and attractive tilework throughout add warmth and character. Relax on the enclosed side porch with peaceful neighborhood views or enjoy outdoor living on the newly build deck designed for sunny afternoons and evening gatherings. Located in the heart of Rock Hall, this home places you close to marinas, public landings, local shops, restaurants, and all the charm this beloved Chesapeake Bay town has to offer. Enjoy seasonal festivities, waterfront living, and the laid-back lifestyle Eastern Shore buyers love. Whether you are looking for a full-time residence, weekend getaway or retirement retreat, this lovely home truly feels like HOME!

5989 N Main St, Rock Hall

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

Charming and full of potential, this 3-bedroom, 1.5-bath Cape Cod home offers a prime in-town Chestertown location with thoughtful updates already in place. New roof (December 2025), central air unit (2022), and new carpet upstairs provide peace of mind, while classic features like hardwood floors, abundant natural light, and a wood-burning fireplace add warmth and character. The flexible layout includes a main-level bedroom and full bath, a formal dining room, and a bright living room. Upstairs, two additional bedrooms and a half bath, easily converted back to a full, offer room to grow. A bonus room off the main level is perfect for a home office, mudroom expansion, or hobby space. The sunroom connects seamlessly to a private backyard. A sizable driveway and detached garage offer ample off-street parking. Architectural plans for a full renovation and addition are available with an acceptable offer. This is an incredible opportunity to customize and add value in a sought-after location. Just a short stroll to Downtown Chestertown, Washington College, and the Chester River, this home offers both convenience and long-term potential.

Charming and full of potential, this 3-bedroom, 1.5-bath Cape Cod home offers a prime in-town Chestertown location with thoughtful updates already in place. New roof (December 2025), central air unit (2022), and new carpet upstairs provide peace of mind, while classic features like hardwood floors, abundant natural light, and a wood-burning fireplace add warmth and character. The flexible layout includes a main-level bedroom and full bath, a formal dining room, and a bright living room. Upstairs, two additional bedrooms and a half bath, easily converted back to a full, offer room to grow. A bonus room off the main level is perfect for a home office, mudroom expansion, or hobby space. The sunroom connects seamlessly to a private backyard. A sizable driveway and detached garage offer ample off-street parking. Architectural plans for a full renovation and addition are available with an acceptable offer. This is an incredible opportunity to customize and add value in a sought-after location. Just a short stroll to Downtown Chestertown, Washington College, and the Chester River, this home offers both convenience and long-term potential.

217 Philosophers Ter, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: Cross Street Realtors LLC.

Tucked in the heart of Rock Hall, this original 3-bedroom, 2-bath Craftsman is as charming as they come. Thoughtfully maintained and updated over time, it blends classic character with everyday comfort. The home features hardwood floors, abundant natural light, and beautifully preserved details throughout. The layout offers flexibility with two updated full bathrooms, one on each level. Recent improvements include a new roof, gutters, front door, refreshed porch, and an encapsulated crawlspace with dehumidifier. Outside, a fenced backyard creates a private setting for entertaining or unwinding on the patio, while the inviting front porch is the perfect spot to start or end the day. Just steps from Rock Hall’s Main Street, you’re within easy reach of local shops, restaurants, live music, marinas, and the waterfront, making this Craftsman an ideal full-time home or weekend escape on the Eastern Shore.

Tucked in the heart of Rock Hall, this original 3-bedroom, 2-bath Craftsman is as charming as they come. Thoughtfully maintained and updated over time, it blends classic character with everyday comfort. The home features hardwood floors, abundant natural light, and beautifully preserved details throughout. The layout offers flexibility with two updated full bathrooms, one on each level. Recent improvements include a new roof, gutters, front door, refreshed porch, and an encapsulated crawlspace with dehumidifier. Outside, a fenced backyard creates a private setting for entertaining or unwinding on the patio, while the inviting front porch is the perfect spot to start or end the day. Just steps from Rock Hall’s Main Street, you’re within easy reach of local shops, restaurants, live music, marinas, and the waterfront, making this Craftsman an ideal full-time home or weekend escape on the Eastern Shore.

21235 Rock Hall Ave, Rock Hall

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: Benson & Mangold, LLC.

$366,000

New Construction Alert! Four beautiful 3BR, 2.5 bath duplexes under construction on Striper Run in Watermans Estates. Nice open 1st floor layout with living, dining & kitchen areas, powder room and separate laundry room. Luxury vinyl plank flooring in the living areas, granite counter tops and stainless appliances are included. Upstairs, there's a primary suite with walk-in closet, full bath, two more spacious bedrooms and another full bath. The 7' x 23' storage room with overhead door provides lots of space for toys and tools. Out back there's a concrete patio and 6 ft vinyl privacy fence. Watermans Estates is an attractive community in the heart of Rock Hall. Walkable or bike-able to restaurants, marinas and shops the location offers easy access to Rock Hall's many festivals and fun events.

New Construction Alert! Four beautiful 3BR, 2.5 bath duplexes under construction on Striper Run in Watermans Estates. Nice open 1st floor layout with living, dining & kitchen areas, powder room and separate laundry room. Luxury vinyl plank flooring in the living areas, granite counter tops and stainless appliances are included. Upstairs, there's a primary suite with walk-in closet, full bath, two more spacious bedrooms and another full bath. The 7' x 23' storage room with overhead door provides lots of space for toys and tools. Out back there's a concrete patio and 6 ft vinyl privacy fence. Watermans Estates is an attractive community in the heart of Rock Hall. Walkable or bike-able to restaurants, marinas and shops the location offers easy access to Rock Hall's many festivals and fun events.

21139 Striper Run, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: Gunther-McClary Real Estate.

$365,000

Well situated 70s Ranch. Original kitchen and baths. Hardwood floors. 3 beds, 2 baths.