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1 Idlewhile Ave Unit 4, Betterton
$449,000
3 Beds ⋅ 3 Baths
Crew's Landing 3 bedroom Townhouse, located in Betterton, The Jewel of the Chesapeake. This 12 unit complex has become a premier waterfront community on the upper Bay. Located on a 5 acre setting of beautiful landscape offering carefree living. It includes a community dock and a great private sandy beach. The unit has had upgrades with wood plank tile floors, kitchen with granite countertops, and stainless steel appliances. Living room with gas fireplace has access to screen porch and deck. Large primary bedroom with a balcony. Primary bath has beautiful tiled walk-in shower, new cabinetry and granite countertop. Third floor bedroom offers expansive views of the upper Bay. Full basement with workbench and closet offers plenty of room for all your toys. A new HVAC system was installed 5yrs ago. An 11,000 lb., remote controlled boat lift with E-drive motors is included. Enjoy maintenance free living.

1 Idlewhile Ave Unit 4, Betterton

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

104 Church Aly, Chestertown
$445,000
2 Beds ⋅ 2 Baths
A perfect pied-a-terre or full time residence, this adorable historic home is just steps from the farmers market, shops, restaurants, theater,art galleries and the Chester River. Zoned residential or business. Completely updated in 2021. Metal roof. Loaded with character and charm.

104 Church Aly, Chestertown

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

Selling Office: Unrepresented.

5761 S Main St, Rock Hall
$440,000
The current owner did a lot line adjustment and is selling 5761 Main Street on 3,547 sq.ft. of land. The 1st floor of the building is used for retail space and the 2nd floor is a 2BR/1 bath apartment.

5761 S Main St, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: Unrepresented.

222 Mount Vernon Ave, Chestertown
$433,000
4 Beds ⋅ 2 Baths
This charming 1916 home in Chestertown's historic district is in a quiet neighborhood next to Washington College, just a short walk from downtown and the waterfront. Three finished levels and high ceilings plus bright, natural light make the home feel airy and spacious. Historic features include original heart-pine hardwood floors and beautiful molding throughout. The first floor includes an adorable kitchen with butcher block countertops, as well as a living room, dining room, and 3/4 bathroom. Upstairs, you’ll find three bedrooms, a full bath, and a walk-in closet. The third floor offers a lofted bedroom and bonus room - perfect for a playroom, office, or workout room. The mahogany-floored porch has interchangeable screens and windows, converting easily from a screen porch into a sunroom. Outside, a new six-foot pressure-treated pine fence provides privacy for the backyard, with an extra fenced garden area. The driveway has off-street parking for two vehicles. Additional home updates include a tankless hot water heater, high-efficiency 3-zone boiler, whole-house surge protector, upgraded panel, and Kenmore gas range. In summer 2025, the current owners invested in over $60,000 in major renovations hoping to stay for many years. They replaced the roof, updated the electrical wiring, and painted the interior. All upgrades were intended to be enjoyed by current homeowners. Unfortunately, they found that they had to move out of state to be closer to a new job.

222 Mount Vernon Ave, Chestertown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: Benson & Mangold, LLC.

201 Birch Run Rd, Chestertown
$430,000
3 Beds ⋅ 2 Baths
*****PRICED $30,000 UNDER THE RECENT APPRAISED VALUE***** One floor living, a wood burning fireplace, and hardwood floors help this represent the cozy but elevated Eastern Shore lifestyle. The Mile Tree Village community is tucked on a quiet cul-de-sac with views of the Chester River. The home has been thoughtfully improved with major 2021 updates including joist replacement, flooring, crawl space encapsulation, and rear fencing all performed by the greatest hits list of Kent County craftsmen, along with freshly stained rough-cut cedar siding in 2025. An oversized two-car garage, serene courtyard with water feature, and a spacious, partially shaded backyard with deck seating create a setting that feels both private and inviting—all just a short walk to downtown shops, restaurants, Washington College, and the town’s parks.

201 Birch Run Rd, Chestertown

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

Selling Office: Blackwell Real Estate, LLC.

21007 Bayside Ave, Rock Hall
$425,000
3 Beds ⋅ 2 Baths
Adorable updated cottage in the heart of town on popular Bayside Avenue offering approximately 1,400 sq. ft. of charming coastal living. This delightful Cape Cod features 3 bedrooms and 2 full baths, with seasonal water views of Rock Hall Harbor from the second floor. The main level offers an open floor plan with a cozy propane fireplace, 2 bedrooms, and 1 full bath, while the entire upper level serves as a spacious private primary suite. Enjoy outdoor living in the fenced rear yard — perfect for pets, entertaining, or relaxing on the back deck while taking in the scenery. A detached one-car garage and storage shed provide plenty of room for bikes, tools, kayaks, and LSV/golf cart storage. Ideally located within walking distance to local favorites including Harbor Shack and Waterman’s Crab House, marinas, harbor festivities, shops, and more. Conveniently situated along the complimentary Rock Hall Rides shuttle route, making it easy to enjoy everything this waterfront town has to offer!

21007 Bayside Ave, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

21120 Green Ln, Rock Hall
$419,000
3 Beds ⋅ 2 Baths
COMING SOON - NEW ROOF!!! Your Chesapeake Bay getaway just steps from Haven Harbour South Marina. Launch your boat, dine on the waterfront, stroll to the beach, and enjoy resort-style living from this beautifully updated home. This updated 3-bedroom, 2-bath rancher situated on an expansive lot with glimpses of the water and room to relax, entertain, and enjoy the Eastern Shore lifestyle. The spacious detached garage provides ample storage for vehicles, boats, and recreational equipment. Unwind in the cooled three-season room overlooking the fenced backyard, offering the perfect setting for gatherings with family and friends after a day on the water. Ideally located just a short walk or golf cart ride from Haven Harbour South Marina, you'll enjoy convenient access to boat slips, waterfront dining, a sandy beach, marina amenities, and breathtaking Chesapeake Bay sunsets. Whether you're seeking a year-round residence, weekend escape, or boating retreat, this property offers comfort, convenience, and the best of Rock Hall living. Wake up, walk to your boat, spend the day on the Chesapeake Bay, enjoy waterfront dining, watch the sunset, and return home to relax in your private backyard. Every day feels like you're on vacation.

21120 Green Ln, Rock Hall

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

Selling Office: Real Broker, LLC - Annapolis.

12089 Blacks Station Rd, Kennedyville
$415,000
4 Beds ⋅ 2 Baths
Charming Cape Cod nestled on a beautiful 2-acre lot offering the perfect blend of space, privacy, and timeless charm! This well-maintained home features a long driveway, 2-car garage, and lovely landscaping that creates wonderful curb appeal. Inside, you’ll find hardwood floors on the main level along with fresh neutral paint throughout the home. The spacious sunroom addition is filled with natural light and offers peaceful views of the picturesque backyard. Nature lovers and gardeners will appreciate the mature fruit trees including apple, pear, and cherry, along with thriving raspberry, blueberry, and blackberry bushes. The flexible main-level bedroom with full bath is ideal for guests, a home office, or convenient one-level living. Upstairs offers generously sized bedrooms with plenty of space and character. Major updates have already been taken care of with a recently updated roof, HVAC system, water softener, and hot water heater. A rare opportunity to enjoy peaceful outdoor living with room to grow! 10 miles to 301, 20 minutes to Chestertown and Middletown.

12089 Blacks Station Rd, Kennedyville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Doug Ashley Realtors, LLC.

no property photo
$415,000
3 Beds ⋅ 2 Baths
Welcome to this beautifully updated 3-bedroom, 1.5-bath rancher offering 1,344 sq ft of comfortable, energy-efficient living. Thoughtfully improved since 2018, this home blends modern upgrades with inviting indoor and outdoor spaces. Step inside to find newer laminate flooring, updated baseboards, and a fully remodeled kitchen featuring soft-close cabinetry, butcher block countertops, and stainless steel appliances. The spacious sunroom is a true highlight, complete with new insulation, drywall, a charming shiplap ceiling, and a cozy gas fireplace with blower—perfect for year-round enjoyment. Major system upgrades provide peace of mind, including all new Pella energy-efficient windows (with six additional windows added to the family room), a 2022 architectural roof with ridge vents, new vinyl siding with added insulation and house wrap, and a fully encapsulated and insulated crawlspace with treated floor joists. The home is equipped with a high-efficiency 2-unit, 4-zone mini-split system (23 SEER), a tankless electric water heater, whole-house water filtration, and a 200-amp electrical panel with generator transfer switch. Enjoy seamless indoor-outdoor living with a 15’ x 19’ three-season sunroom featuring floor-to-ceiling E-Z Breeze windows, LVP flooring, and a ceiling fan. Outside, the 150’ x 100’ lot backs to trees for added privacy and includes a paver patio with firepit, retractable awning, and beautifully landscaped grounds. The fenced backyard features wood slat fencing with wire mesh, along with apple and fig trees, grapevines, greenhouse framing and raised beds for garden enthusiasts. Additional features include a new laundry room with half bath, updated main bath, new exterior doors with storm doors, upgraded lighting, gravel driveway, and a storage shed with added screened porch, power, and lighting (shed conveys as-is). Located on a quiet street, yet conveniently walkable to local restaurants and the beach, this move-in ready home offers the perfect blend of comfort, efficiency, and lifestyle.

20812 Mercer Ave, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: Rock Hall Properties Real Estate.

6270 Rock Hall Rd, Rock Hall
$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.

109 S College Ave, Chestertown
$410,000
3 Beds ⋅ 3 Baths
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.

217 School St, Millington
$409,000
4 Beds ⋅ 3 Baths
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.

Bradford Johnson Road, Golts
$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.

189 Birchwood, Galena
$395,000
3 Beds ⋅ 3 Baths
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.

10790 Worton Rd, Worton
$395,000
3 Beds ⋅ 2 Baths
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.

8629 Airy Hill Rd, Chestertown
$395,000
3 Beds ⋅ 2 Baths
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.

32287 Quinn Rd, Massey
$390,000
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.

22523 Crouchs Ln, Rock Hall
$385,000
3 Beds ⋅ 3 Baths
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.

107 Boxwood Ln, Galena
$385,000
3 Beds ⋅ 2 Baths
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.

23416 Cloquet Rd, Chestertown
$384,000
3 Beds ⋅ 2 Baths
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.

11901 Dairy St, Kennedyville
$382,500
4 Beds ⋅ 3 Baths
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.

107 Flying Cloud Dr, Chestertown
$380,000
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.

14037 E Beechwood Rd, Galena
$375,000
3 Beds ⋅ 2 Baths
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.

105 Dogwood Dr, Galena
$370,000
3 Beds ⋅ 2 Baths
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.

5989 N Main St, Rock Hall
$370,000
3 Beds ⋅ 2 Baths
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.

217 Philosophers Ter, Chestertown
$370,000
3 Beds ⋅ 2 Baths
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.

21235 Rock Hall Ave, Rock Hall
$370,000
3 Beds ⋅ 2 Baths
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.

521 N Kent St, Chestertown
$365,000
3 Beds ⋅ 2 Baths
Well situated 70s Ranch. Original kitchen and baths. Hardwood floors. 3 beds, 2 baths.

521 N Kent St, Chestertown

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

Selling Office: TTR Sotheby's International Realty.

23264 Clarissa Rd, Chestertown
$365,000
3 Beds ⋅ 2 Baths
Tucked neatly on a corner in Chesapeake Landing, this three-quarter acre parcel is among one of the largest in the neighborhood. The 2020 custom built home exudes simple luxury. Offering three bedrooms and two full baths in a simple and efficient floorplan, is has flow and comfort in mind. It features a modern kitchen with tall quiet close cabinets, granite counter tops and a tile backsplash, stainless appliances, and an ample pantry for storage. Six-over-six oversized windows throughout the home, extra tall doors, a transom window over the front door, and a ten-foot door to the screen porch allows light to pour inside. A full and separate laundry room remove that chore from the living space and offer a dedicated work room with storage. The Primary Suite includes a generous walk-in closet and en suite bath. Since 2021, upgrades and improvements include: screened porch, Leafguard on all gutters, shed to coordinate with the home’s aesthetics, asphalt driveway, thoughtful landscaping, water treatment system, and is wired for IQ Fiber (formerly ThinkBig) for internet. This home is absolutely, without question, turnkey and ready for its new stewards!

23264 Clarissa Rd, Chestertown

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

Selling Office: Rosendale Realty.

21133 Striper Run, Rock Hall
$364,900
3 Beds ⋅ 3 Baths
New Construction Alert! The last two beautiful 3BR, 2.5 bath duplexes under construction on Striper Run in Watermans Estates are now for sale. Nice open 1st floor layout with living, dining & kitchen areas, powder room and separate laundry room. Luxury vinyl plank flooring in the 1st and 2nd levels is 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.

21133 Striper Run, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: RE/MAX Chesapeake.

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