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21712 Centennial Ln, Rock Hall
$395,000
3 Beds ⋅ 3 Baths
Brand-new construction in the Crosby Woods Subdivision! This thoughtfully designed 3-bedroom, 3-bath home offers convenient one-level living with an open floor plan, recessed lighting, granite countertops, a kitchen island, pantry, and stainless steel appliances. The home features two primary suites with private tiled bathrooms, including one with an additional sitting area for added comfort and flexibility. A dedicated laundry/utility room, welcoming front porch, and rear deck provide both convenience and outdoor enjoyment. Situated on a spacious 0.601-acre lot backing to trees and set back from the road, this property offers privacy while remaining just 0.5 miles from downtown Rock Hall. Don't miss the opportunity to own this beautiful new home!

21712 Centennial Ln, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

11989 Augustine Herman Hwy, Kennedyville
$245,000
2 Baths
Prime duplex opportunity in Kennedyville with immediate positive cash flow potential and plenty of future options. This versatile property offers an exceptional opportunity for a wide range of buyers, from first-time home buyers looking for added flexibility, to downsizers seeking a manageable home with supplemental income or multigenerational households in need of separate yet connected living space, and investors searching for strong day-one returns. With income-producing potential already in place, this duplex stands out as a smart purchase for anyone who values both immediate cash flow and long-term upside. One of the standout features of the property is the large backyard, offering space that is increasingly hard to find and full of possibility. Whether envisioned as an outdoor entertaining area, garden, play space, or future enhancement opportunity, Combined with its desirable location, the property offers the rare combination of current performance and untapped potential. For buyers who want a duplex that can serve today’s needs while also creating opportunities for tomorrow, this is a compelling chance to own a property with broad appeal, functional flexibility, and room to grow.

11989 Augustine Herman Hwy, Kennedyville

Listing courtesy of Gunther-McClary Real Estate. Contact:

13235 Knotts Ln, Golts
$1,495,000
3 Beds ⋅ 2 Baths
106 Acre Recreational Farm Hidden away at the end of a small country lane always a special lifestyle for the outdoor lover. Regulations prohibit surrounding farms from growing communities. BIG BUCKS,, GAGGLE OF TURKEYS, WOOD DUCKS & GEESE. Narrow fields, hedgerows and curved woods giving lots of cover near the ponds and impoundments gives hunting sites spread throughout. Recent Selective Forrest management work has improved the hunt ability offering additional trails and food plot areas. Home was moved approx 20 years siting onto a new foundation then renovated to enjoy the views and ready for its new owners. Horses, we have some fencing, turn in shed, 4 stall to the rear of 3 level barn giving you plenty of room for storage of hay, straw and feed. And think how much fun to ride through and impoundment? Almost adjoins the 4,000 Millington Wildlife Preserve, with riding trails. Remember this area is protected from the surrounding farms becoming communities and the end of your dreams. Haven’t you work Hard all these Years? Reward yourself now with unique Opportunity while it’s available. Do not enter property without appointment and listing agent. New County Zoning change This would make a great extra income opportunity Possible Farm Wedding site ** IMAGINE A NEW CLASIC BARN AND MAYBE EVEN A GAZIBO BOTH OVERLOOKING THE LARGEST POND INCLUDING LANDSCAPING, PARKING AND OTHER FEATURES TO THIS UNIQE PROPERTY. LETS TALK ABOUT IT… PHIL RIORDAN AGENT MEREDITH FINE PROPERTIES

13235 Knotts Ln, Golts

Listing courtesy of Meredith Fine Properties. Contact:

4818 Piney Neck Rd, Rock Hall
$289,000
3 Beds ⋅ 1 Baths
Charming home located just outside of town, extensively renovated between 2005-2008. Renovations included taking the home down to the studs and updating insulation, drywall, windows, furnace, plumbing, flooring, kitchen, and bathroom. The open floor plan creates a bright and airy living space, and a 2020 addition added a third first-floor bedroom on the main level, offering convenient one-level living. Situated on nearly an acre, the property includes a detached garage/shed and a spacious yard. Water conditioner is owned but not operational, and the dishwasher conveys but is not in connected. Property is being sold As-Is. A small area of wetlands is located in the far rear corner of the parcel.

4818 Piney Neck Rd, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

13235 Knotts, Golts
$1,495,000
3 Beds ⋅ 2 Baths
Hidden away at the end of country lane Privacy awaits Surrounded by woods 106 Acres Hunting Farm in North East Kent County. Government regulation's insure surrounding farms will remain rather than growing communities. About 60 acres woods, 26 acres of grain fields, with over 7 acres impoundments, deep ponds for fishing plus a wood duck pond in the woods. Impoundments are equipped with water level control. Buyer to verify acreage 1900 farm home renovated about 20 yrs. Ago including new heat pump. Three Bedrooms, 2 Full Baths, Dining Room, Living Room, Family Room with Fireplace. Enjoy the picturesque views of farm from 2nd floor deck off master bedroom Perfect setting for Canadian geese to spend the nights adding to your enjoyment. Recent Selective Forestry work completed improved opportunity with additional trails and food-lots areas add shelter food for wildlife. Some fencing & 4 stalls behind the barn for horses plus a turn in shed. Many nice duck hunting properties are impacted by global warming rising sea level not an issue here. Elevation is well over 50 feet above sea level, so you a safe investment that can be enjoyed for generations to come. And surrounding farms protected from becoming communities and ending your dreams. Listed on June 20, 2026 some sites say several years which is not accurate. Featuring Fiber Optic for your Enjoyment and recently install heat pump. Haven’t You Worked Hard? Now Your Time for to Reward Yourself..20 minutes from Middletown, De that offers sales tax free shopping and dining. Possible extra income farm wedding site subject to county approval. ** IMAGINE A NEW CLASSIC BARN AND PERHAPS A GIZABO OVERLOOKING THE LARGEST POND? ADD IN A GREAT LANDSCAPING PARKING AND FEATURES FOR A DESIRABLE DESTINATION. WITH SO MANY PEOPLES SO CLOSE. Wilmington, Towson & Bay Bridge about 50 minutes. Philadelphia and West Chester about 90 minutes. Almost adjoins the 4,000 Millington Wildlife Preserve. Google it to see what’s available. HERE IS YOUR CHANCE * STEP UP, AND ENJOY A GENERATIONAL TREASURE! Do not enter property without appointment and with Listing Agent. PHIL RIORDAN AGENT MEREDITH FINE PROPERTIES

13235 Knotts, Golts

Listing courtesy of Meredith Fine Properties. Contact:

104 Conley Dr, Chestertown
$239,900
3 Beds ⋅ 2 Baths
Price Improvement! Now offered at $239,900 Welcome to 104 Conley Drive in the heart of Chestertown! This move-in ready 3-bedroom, 1.5-bath townhome offers comfortable, low-maintenance living with a spacious layout and fenced rear yard. The main level features a bright living room, an eat-in kitchen with ample dining space, and a convenient half bath. Upstairs, you’ll find three bedrooms and a full bath. Notable updates include a new HVAC system installed in 2020 and a sewer line replacement completed approximately four years ago, providing added peace of mind for the next owner. Enjoy outdoor entertaining, gardening, or relaxing in the private fenced backyard. Conveniently located near shopping, dining, schools, parks, the YMCA, and historic downtown Chestertown, this home is an excellent opportunity for first-time buyers, downsizers, or investors alike. Schedule your showing today!

104 Conley Dr, Chestertown

Listing courtesy of Cummings & Co. Realtors. Contact:

11989 Augustine Herman Hwy, Kennedyville
$245,000
Prime duplex opportunity in Kennedyville with immediate positive cash flow potential and plenty of future potential. This versatile property offers an exceptional opportunity for a wide range of buyers, from first-time home buyers looking for added flexibility, to downsizers seeking a manageable home with supplemental income or multigenerational households in need of separate yet connected living space, and investors searching for strong day-one returns. With income-producing potential already in place, this duplex stands out as a smart purchase for anyone who values both immediate cash flow and long-term upside. One of the standout features of the property is the large backyard, offering space that is increasingly hard to find and full of possibility. Whether envisioned as an outdoor entertaining area, garden, play space, or future enhancement opportunity, Combined with its desirable location, the property offers the rare combination of current performance and untapped potential. For buyers who want a duplex that can serve today’s needs while also creating opportunities for tomorrow, this is a compelling chance to own a property with broad appeal, functional flexibility, and room to grow.

11989 Augustine Herman Hwy, Kennedyville

Listing courtesy of Gunther-McClary Real Estate. Contact:

234 N College Ave, Chestertown
$79,000
2 Beds ⋅ 1 Baths
Investor Special – Charming Colonial in Prime Chestertown Location! Welcome to 234 N College Ave, an adorable colonial full of character and potential, nestled in the heart of historic Chestertown. This short sale opportunity is a rare find for savvy investors or buyers ready to bring their vision to life. With classic colonial charm, this property offers the perfect canvas for renovation or restoration. Located near downtown Chestertown’s shops, restaurants, and waterfront, the location can’t be beat. Original architectural details, a cozy layout, and timeless curb appeal make this home a standout gem waiting to be polished. Don't miss your chance to invest in one of Maryland’s most beloved small towns. Sold as-is. Cash or renovation loans preferred.

234 N College Ave, Chestertown

Listing courtesy of Cummings & Co Realtors. Contact:

104 Acorn Dr, Chestertown
$275,000
3 Beds ⋅ 3 Baths
Enjoy the convenience of townhome living in Oak Hollow, just minutes from historic downtown Chestertown, local schools, and the YMCA. With approximately 1,900 square feet of living space across three levels, this home offers a flexible layout with room to make it your own. The ground level features a versatile bonus room that could serve as a home office, workout space, or recreation room, along with an attached one-car garage. Upstairs, the main living level offers a spacious living room and an eat-in kitchen with access to a private rear deck overlooking a wooded backdrop—an inviting spot to relax or enjoy your morning coffee. The upper level includes three bedrooms, including a primary suite with a private bath, plus a convenient dedicated laundry area. The Seller is offering a $2,500 credit toward painting, cosmetic updates, or carpet, giving the next owner an opportunity to personalize the space to suit their style. Conveniently located and offering a practical, three-level layout, this Oak Hollow townhome is worth a look for buyers seeking their first home, those looking to downsize, or investors exploring rental opportunities.

104 Acorn Dr, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

25416 Commerce Ln, Chestertown
$1,100,000
Unique opportunity to expand or start your business just minutes from the Eastern Shore thoroughfares of Routes 301 and 213 and also just outside of downtown Chestertown. The blend of infrastructure and zoning such as public sewer, Industrial zoning, tractor trailer access, railway abutting the business park and 3 phase electric throughout the building make this irresistible for a wide variety of businesses. Iconic Eastern Shore architect Peter Newlin designed the building with passive solar heating and cooling in mind as evidenced in the dynamic roof pitch. Radiant floor heating ensures that not only are your employees happy but your machines and materials are better protected as well. The layout allows for great separation of personnel, office tasks, and shop space. 3 Bathrooms, one with shower, allow for the staff to have their space of their own without sacrificing customer experience. Quality control, conference and storage rooms are thoughtfully planned out and spacious. The exterior provides ample parking for staff and customers separately while also designed for tractor trailor turnaround. Over 2 acres and extra sewer allotment allow for vision and future possibilities. Less than 2 hours from Philadelphia, Wilmington, Baltimore, and Washington DC. Opportunities like this don't come up often so jump in now for the growth of the Eastern Shore.

25416 Commerce Ln, Chestertown

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

8796 Maryland Pkwy, Chestertown
$1,495,000
Circa 1743 with a stately 1825 addition, The Inn at Mitchell House is a rare pre-Revolutionary manor home on 9+ manicured acres on Maryland's Eastern Shore. Listed on the National Star-Spangled Banner Trail and just a mile from the Chesapeake Bay, this storied property offers a once-in-a-generation chance to own one of the region's most beloved historic estates. The grounds unfold past champion and organic fruit trees, a generous herb garden, an original 18th-century smoke house, two private bridges over Stoneybrook Pond which are all framed by woods and rolling farm fields. Inside, nine bedrooms and six-and-a-half bathrooms reveal nearly two and a half centuries of craftsmanship: original wood floors, brick floors in the dining room and kitchen, signature Bulls Eye moldings, exposed hand hewn beams, eight fireplaces and soaring 11-foot ceilings. For more than 40 years the property has operated as a successful Bed & Breakfast. An optional furniture package is available for a seamless turnkey transition. Its origins as a single-family residence also make it an extraordinary private estate, full-time home or weekend retreat. A coveted sewer allotment is included with the sale which opens the door for a future carriage house, barn, additional dwelling, stable, studio or expanded hospitality use. A new roof, a complete exterior paint job, new hot water heater, new well pump and updated electrical service were completed in 2025–2026. This delivers the rare combination of historic character and modern peace of mind. Tolchester Marina and the Shanty Beach Bar are a mile away. Rock Hall is six miles down the road and the charming historic district of Chestertown is just ten miles away. After nearly four decades of careful stewardship, the current owners are ready to pass on the privilege and the story of The Mitchell House.

8796 Maryland Pkwy, Chestertown

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

31673 W Edge Rd, Millington
$359,000
2 Beds ⋅ 1 Baths
Cute cottage located on the upper Chester River! Entertain on the spacious rear deck. Watch the Chester River slowly meander to more wide open waters. Follow the gently sloped backyard to the updated bulkhead at the water's edge. Launch your kayak and explore the river and allow the tide to take you as you explore the river. When done relax indoors to an updated home that offers an open floor plan as the living room and kitchen merge as one. This home was updated several years ago so there is very little you would need to do other than adding your own personal touches. There are 2 bedrooms with wood floors and a single bath. The living room and one of the bedrooms offers access to the rear deck through sliding glass doors. There is a full basement with connecting stairs from the main level. Here is where you will find the laundry. There is plenty of storage space and could possibly be finished living space if the new owner would like to tackle the project. You will be hard pressed to find anything on the water this cute and in this price range so come take a look and decide for yourself!

31673 W Edge Rd, Millington

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

21173 And 21163 Chesapeake Ave, Rock Hall
$649,900
4 Beds ⋅ 4 Baths
This home has been meticulously maintained and is located in the heart of everything Rock Hall has to offer! The 2 story entrance foyer with tile floors is just the beginning of the surprise you will find in this special, 2,900+/- square foot, home. There are 4 bedrooms, 3.5 baths, a large living room with cathedral ceiling, 2 bedrooms upstairs and 2 bedrooms down, heat pump and mini-split systems for heating and cooling and is move in ready!! A free standing propane stove will help take the chill off during the cooler months. The dining area is just off the kitchen with great views from the large picture window. The kitchen offers all of the major appliances. The laundry room is also a very nice size. There is a side deck for outdoor entertaining. Need storage?.....There is an interior storage/shop room and a large shed to keep some of your summer toys. The crawl space has been recently encapsulated. Need more room or maybe a guest house? The adjoining lot already has sewer and water and is included with the sale. Or just enjoy the open space between you and the next door neighbors. This could make a great full or part time residence! Only a short distance to the harbor and restaurants! Watch the Rock Hall July 4th fireworks right from your deck next year!!

21173 And 21163 Chesapeake Ave, Rock Hall

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

8796 Maryland Pkwy, Chestertown
$1,495,000
9 Beds ⋅ 7 Baths
Circa 1743 with a stately 1825 addition, The Inn at Mitchell House is a rare pre-Revolutionary manor home on 9+ manicured acres on Maryland's Eastern Shore. Listed on the National Star-Spangled Banner Trail and just a mile from the Chesapeake Bay, this storied property offers a once-in-a-generation chance to own one of the region's most beloved historic estates. The grounds unfold past champion and organic fruit trees, a generous herb garden, an original 18th-century smoke house, two private bridges over Stoneybrook Pond which are all framed by woods and rolling farm fields. Inside, nine bedrooms and six-and-a-half bathrooms reveal nearly two and a half centuries of craftsmanship: original wood floors, brick floors in the dining room and kitchen, signature Bulls Eye moldings, exposed hand hewn beams, eight fireplaces and soaring 11-foot ceilings. For more than 40 years the property has operated as a successful Bed & Breakfast. An optional furniture package is available for a seamless turnkey transition. Its origins as a single-family residence also make it an extraordinary private estate, full-time home or weekend retreat. A coveted sewer allotment is included with the sale which opens the door for a future carriage house, barn, additional dwelling, stable, studio or expanded hospitality use. A new roof, a complete exterior paint job, new hot water heater, new well pump and updated electrical service were completed in 2025–2026. This delivers the rare combination of historic character and modern peace of mind. Tolchester Marina and the Shanty Beach Bar are a mile away. Rock Hall is six miles down the road and the charming historic district of Chestertown is just ten miles away. After nearly four decades of careful stewardship, the current owners are ready to pass on the privilege and the story of The Mitchell House.

8796 Maryland Pkwy, Chestertown

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

21424 Catholic Ave, Rock Hall
$399,000
4 Beds ⋅ 2 Baths
Welcoming to 21424 Catholic Ave, located in the heart of Rock Hall! Walking distance to many shops, restaurants, and marinas. Nicely situated on a large in-town parcel, the largest residential lot on Catholic Avenue. This 4-bedroom home was redone from the inside out in 2024. The welcoming living space contains original wood accents, adding much charm to this newly updated home. Spacious open living space with a beautifully renovated kitchen, custom wood cabinets, new LVT, and engineered hardwood flooring throughout. Three bedrooms, with great closet space, share a full bath. At the end of the home, you'll find the primary bedroom, with a spacious primary bath and walk-in closet. The oversized two-car garage has plenty of room for extra storage. One-floor living and a two-car garage are hard features to find in downtown Rock Hall. Outside, the possibilities are endless; there's ample room for outdoor activities or projects. Updates include: -Crawlspace encapsulation and whole house dehumidifier -10 new windows -New 25 year roof -Siding, shutters & new gutters -New flooring, engineered hardwood, LVT and carpet -Completely updated kitchen with custom cabinetry -HVAC heat pump & AC -200 amp breaker panel And more!

21424 Catholic Ave, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

26566 Lambs Meadow Rd, Worton
$2,475,000
Versatile commercial property, featuring just over 23,000 sq ft of workshop and/or warehouse space on 6.71 acres. Conveniently located on 298, just over 30 minutes to Middletown, Delaware, under an hour to Wilmington, and just down the road from Chestertown and Galena.  The newest workshop was constructed in 2021. Featuring 13’ high rolling doors, concrete floors, insulated walls, and a pellet stove for the winter.  The original workshop building has a second-floor loft, bathroom, and separate rooms that could facilitate multiple offices. The roof was replaced and exterior walls painted in 2021. The addition next to the original building was completed in 2014. This section features 4 bays with 11’ rolling doors and 3,000 sq ft of space. Lastly, the 118’ x 48’ storage room can house almost any kind of farm equipment. The additional acreage is currently farmed.  Enter from either 298 or Still Pond Rd. Plenty of parking and easy drive-through or turn-around space for trailers.  A rare commercial find in Kent County with ample potential! Opportunity to purchase the residential home in conjunction with the commercial property. 12296 Still Pond Rd is a spacious 3-bedroom, 2.5 bath, brick house with an updated kitchen, bathrooms, attached garage, and additional outbuildings. The home features a dedicated dining space, living room, a bonus room that could be used as an office or den, and a 3-season back porch.  **The commercial property and residential home are listed for $2,475,000. Showings by appointment only- do not enter property without scheduled appointment

26566 Lambs Meadow Rd, Worton

Listing courtesy of Gunther-McClary Real Estate. Contact:

26566 Lambs Meadow Rd, Worton
$2,100,000
Versatile commercial property, featuring just over 23,000 sq ft of workshop and/or warehouse space on 6.71 acres. Conveniently located on 298, just over 30 minutes to Middletown, Delaware, under an hour to Wilmington, and just down the road from Chestertown and Galena.  The newest workshop was constructed in 2021. Featuring 13’ high rolling doors, concrete floors, insulated walls, and a pellet stove for the winter.  The original workshop building has a second-floor loft, bathroom, and separate rooms that could facilitate multiple offices. The roof was replaced and exterior walls painted in 2021. The addition next to the original building was completed in 2014. This section features 4 bays with 11’ rolling doors and 3,000 sq ft of space. Lastly, the 118’ x 48’ storage room can house almost any kind of farm equipment. The additional acreage is currently farmed.  Enter from either 298 or Still Pond Rd. Plenty of parking and easy drive-through or turn-around space for trailers.  A rare commercial find in Kent County with ample potential! Opportunity to purchase the residential home in conjunction with the commercial property. 12296 Still Pond Rd is a spacious 3-bedroom, 2.5 bath, brick house with an updated kitchen, bathrooms, attached garage, and additional outbuildings. The home features a dedicated dining space, living room, a bonus room that could be used as an office or den, and a 3-season back porch.  **The commercial property and residential home are listed for $2,475,000. Showings by appointment only- Do not enter property without scheduled appointment

26566 Lambs Meadow Rd, Worton

Listing courtesy of Gunther-McClary Real Estate. Contact:

6202 Rock Hall Rd, Rock Hall
$425,000
This unique mixed-use property offers exceptional flexibility and opportunity just outside the town of Rock Hall. The first floor features a versatile storefront currently operating as a bookstore, with a history of successful uses including a fabric studio, pottery studio, marine engine shop, and appliance store—showcasing its adaptability for a wide range of business ventures. The back room on the first floor was also used as a bedroom for guest in the past as well. The second-floor residential space provides comfortable living with an eat-in kitchen, formal living room, family room, one full bath, and two bedrooms. A spacious rear deck extends the living area outdoors, perfect for relaxing or entertaining. Additional improvements include a 35’ x 28’ pole barn and a 28’ x 14’ shed currently utilized as a bookstore event space, adding even more functional possibilities. The property also features a beautiful garden area ideal for outdoor gatherings and enjoyment. With its prime location just outside Rock Hall, this property blends commercial opportunity with residential comfort in a highly desirable setting.

6202 Rock Hall Rd, Rock Hall

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

Map 36 Parcel 80 Watertower Road, Chestertown
$55,000
Discover the potential of this open .69-acre lot in Fairlee! Whether you’re looking to build your dream home, create a weekend retreat, or invest in future development, this property offers endless possibilities. Zoned Village, this lot could potentially allow for a duplex or multiple dwellings, making it an excellent opportunity for builders, investors, or buyers seeking additional flexibility. Nestled off the main road and deeded with a right-of-way for access, this parcel offers a peaceful, private setting while remaining conveniently close to local amenities, recreation, and the waterfront charm of the Eastern Shore. Public water and sewer may be available, offering the potential convenience of public utilities without the expense and maintenance of a private well or septic system. Buyer to verify availability of allocations and is responsible for any associated fees. Don’t miss this chance to own a versatile piece of land in a desirable location with great potential for future growth and development!

Map 36 Parcel 80 Watertower Road, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

21123 Striper Run, Rock Hall
$344,900
3 Beds ⋅ 3 Baths
NEW PRICE — $344,900! MORE SPACE, MORE FLEXIBILITY & NO HOA! Discover an exceptional opportunity in the charming waterfront town of Rock Hall! Offering approximately 2,040 square feet of living space, an oversized lot and a versatile floor plan, this beautifully maintained home has so much more to offer than meets the eye! Featuring 3 bedrooms, 2 full baths, a powder room and an impressive oversized sunroom/flex space that’s even larger than the primary suite! With its own private exterior entrance and direct kitchen access, this incredible bonus space offers endless possibilities for a home office, guest retreat, hobby room or additional living area. Inside, you’ll find beautiful hardwood flooring, a cozy gas fireplace, crown molding, updated lighting, generous storage and a plumbed bar area ready for your personal touch. Outside, enjoy ample parking, room for your golf cart and the added freedom of NO HOA FEES! Imagine enjoying everything Rock Hall has to offer! Explore nearby marinas, boating, fishing, waterfront restaurants, coffee shops, live music, local shops and the relaxed Eastern Shore lifestyle. Whether you’re searching for a year-round residence or a weekend getaway, this home offers the space and versatility to make it your own. ANOTHER OPTION WORTH EXPLORING! Seller will also consider a short-term SIX-MONTH RENTAL, subject to mutually acceptable terms. NOW OFFERED AT $344,900! Generous living space, a unique bonus room, an oversized lot, NO HOA and flexible options make this a home worth seeing in person. Schedule your private tour today and discover the possibilities!

21123 Striper Run, Rock Hall

Listing courtesy of Chaney Homes, LLC. Contact:

21124 Striper Run, Rock Hall
$355,000
3 Beds ⋅ 3 Baths
Location is EVERYTHING. Upgrades are EVERYTHING. And this stunning Rock Hall home offers BOTH. Perfectly positioned in the heart of Rock Hall, Maryland, this beautifully upgraded home delivers the coastal lifestyle buyers are searching for on Maryland’s Eastern Shore. Imagine hopping on your golf cart or bike and being just minutes from waterfront restaurants, marinas, local shops, live music, and all the charm that makes downtown Rock Hall one of the Eastern Shore’s most beloved waterfront towns. And let’s talk about the upgrades… because they absolutely blow new construction away. From the moment you walk through the door, you’ll notice the difference. The level of craftsmanship, custom finishes, thoughtful details, and high-end touches throughout this home are the kind buyers WANT but rarely get from a builder at this price point. Simply put, you will NOT find these upgrades in new construction without spending significantly more. The stunning kitchen is the heart of the home, featuring upgraded finishes, custom details, and a layout designed perfectly for entertaining and everyday coastal living. Every space throughout the home feels warm, inviting, and move-in ready with details that immediately stand out. Whether you’re searching for a full-time residence, weekend getaway, vacation home, Airbnb investment opportunity, or second home near the Chesapeake Bay, this property checks every box. -High-end upgrades throughout -Stunning kitchen with custom finishes -Spacious layout designed for entertaining -Move-in ready with luxury details throughout -Golf cart or bike ride to marinas, restaurants, and downtown Rock Hall -Minutes to waterfront dining, boating, and the Chesapeake Bay -The perfect blend of location, lifestyle, and luxury upgrades Homes with THIS location and THIS level of upgrades rarely hit the market in Rock Hall… and when they do, buyers move FAST. If you’ve been searching for a beautifully upgraded home in Rock Hall, Maryland with close access to marinas, boating, waterfront restaurants, and Chesapeake Bay living, this is the one you do not want to miss.

21124 Striper Run, Rock Hall

Listing courtesy of RE/MAX Executive. Contact:

31436 Sassafras River Ave, Galena
$2,150,000
4 Beds ⋅ 4 Baths
Luxury deep water retreat on the Sassafras River: an exceptional custom waterfront crafted residence Offering expansive river views, a private deep-water pier, resort style amenities and distinctive natural timber architectural. The custom log construction adds warmth, character and architectural distinction throughout the home The current owners had their 70 ft boat docked there for 10 years with space for several boats to be docked as well. INDOOR POOL looking to the outdoors, situated on a DOUBLE LOT, with a glass enclosure and loads of space to entertain! There are 2 separate upper-level quarters, one for guests which includes a family room, sitting room and full bath. So much potential to utilize at least 2 of the rooms for bedrooms. The primary suite on the other side of the home includes 2 walk-in closets, a dressing room. full bath with soaking tub, an office space and a sitting area with waterfront views. 3 bedrooms with potential to have 5 bedrooms. Set on the tranquil shores of the Sassafras River, this striking custom-built home, blends timeless craftsmanship with resort-style amenities—perfect for effortless entertaining and relaxed waterfront living. The great room includes soaring beams, walls of glass, and panoramic river views Deep water frontage with private pier, 3,000 lb. boat lift and ideal for larger boats as well, crabbing, fishing, and sunset cruising. Year‑round indoor pool pavilion with lounge seating, beverage bar, and easy walk-out. Chef’s kitchen featuring premium appliances, expansive island, and seamless flow to dining and outdoor spaces. Multiple decks and patios for al fresco dining, plus level lawn to the water’s edge. There is even a small kitchenette in the garage for those hardcore entertainers! A full house generator is also present and 3 HVAC units to cool the home. This home would make an amazing Air B and B! There is an additional cabin with sleeping bunks and amenities for those overnight guests that never want to leave. Please click on the walkthrough tour and floor plans are also available.

31436 Sassafras River Ave, Galena

Listing courtesy of EXP Realty, LLC. Contact:

Sandy Bottom Road, Chestertown
$49,000
Escape to the peace and quiet of the countryside with this beautiful private wooded 2-acre lot, tucked away down a secluded gravel lane. Offering a perfect blend of mature trees and a partially open entrance area, this property is ideal for camping, hunting, recreation, or simply enjoying nature in a tranquil setting. Bring your RV or pitch a tent and enjoy the great outdoors! Electric is available at the road, and the seller has marked the approximate property corners and boundaries for convenience (no survey on file). A seasonal hand-dug well is also located on the property. Whether you're looking for a weekend getaway, a place to gather around bonfires, or your own private retreat in nature, this property offers endless possibilities to relax and unwind outdoors.

Sandy Bottom Road, Chestertown

Listing courtesy of Village Real Estate Company LLC. Contact:

21190 Green Ln, Rock Hall
$850,000
Unique opportunity offering two adjoining parcels with exceptional potential in Rock Hall. Parcel 1 consists of approximately 1.4 acres located on Geen Lane and is zoned Critical Area Residential. Improvements include the foundation of a pre-existing structure, an existing well, and a grinder pump connected to public sewer already installed. Buyer to verify well usability and buildability. Parcel 2 is accessed through Parcel 1 and consists of approximately 9 acres with 706 feet of shoreline per survey plat. Zoned Commercial Critical Area (CAR) and Marine (M), this parcel offers a wide range of potential commercial and marine-related uses. Excellent opportunity for investors, marina-related businesses, or those seeking a unique waterfront development opportunity. Buyer to verify all intended uses, zoning regulations, approvals, and buildability of the property.

21190 Green Ln, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

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