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29313 Glencoe Rd, Kennedyville
$1,100,000
3 Beds ⋅ 2 Baths
Welcome to 29313 Glencoe Rd Kennedyville. Experience waterfront living at its finest with this well-maintained 3-bedroom, 2-bath ranch home. Designed for comfort and relaxation, the home features just a few of the amenities of a bright sunroom, and a spacious walk-out basement. Outside, you'll find two detached garages with additional storage above, offering ample room for vehicles, hobbies, and equipment. An original out building, called the fish house offers a unique perspective of the area. A newer pier with a boat lift and floating dock provides easy access to the water, making it perfect for boating, fishing, or simply enjoying life on the Sassafras River & other tributaries. The property boasts approximately 200 feet of bulkheaded shoreline and a small sandy beach, creating the quintessential waterfront retreat. Elevated views stretch down the Sassafras River and across Freeman Creek, where you can watch abundant wildlife throughout the seasons. Begin each day with breathtaking sunrises over the Sassafras River. This exceptional waterfront property offers the perfect blend of comfort, convenience, and scenic beauty.

29313 Glencoe Rd, Kennedyville

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Gunther-McClary Real Estate.

29341 Glencoe Rd, Kennedyville
$890,000
2 Beds ⋅ 2 Baths
NO LOT LINE ADJUSTMENT!!! Nestled along the serene banks of the Sassafras River, this charming brick fixer-upper offers a rare opportunity to create your dream waterfront retreat. Set on a sprawling 2.58-acre lot with 175 feet of private shoreline, the property boasts breathtaking river views, peaceful natural surroundings, and direct deep-water access. Inside, the home offers over 1,500 square feet of functional living space ready for your personal touch. It features 2 bedrooms, 2 full baths, a cozy family room with a fireplace, and a spacious river room adorned with stunning bluestone flooring. An expansive enclosed porch invites you to sip your morning coffee while taking in the sunrise over the water. A conveniently attached garage adds to the home’s functionality. The real star of this property is outside: a private 185-foot dock with 4+ MLW, complete with a boathouse, boat lift, and launch ramp — perfect for boating, kayaking, paddleboarding, or simply enjoying life by the water. Whether you’re an avid water enthusiast or seeking a tranquil escape, this location delivers. Offered strictly AS IS, this property presents multiple possibilities — renovate, expand, or start anew. Whatever your vision, the actual value lies in the land and unparalleled location on one of the most desirable stretches of the Sassafras River. Please do not walk on the dock, as it needs to be renovated along with the boathouse. There is a shared driveway easement; however, please confirm with the county that you have the option to put in your own driveway.

29341 Glencoe Rd, Kennedyville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Unrepresented Buyer Office.

13983 Turners Point Rd, Kennedyville
$567,000
2 Beds ⋅ 3 Baths
Impeccably kept Kentmore Park home with a white picket fence. Over two acres with private rear yard for relaxation. Adorable brick outbuilding for storage, home office, man cave or she shed. Gazebo for al fresco dining, afternoon card games or just enjoying nature. Two additional sheds for storing just about anything. Habitat for many bird species in season. Owl, Heron and Eagle territory year round. This home mixes the old with the new. Character throughout this custom built home. Architectural details, crown and dentil molding. Large kitchen for casual dining and entertaining. Designer countertops and stainless appliances topped off with a Viking range and an antique coal range by AGA. Plenty of gathering space at the elongated island. Large windows bring the outside in to the kitchen. Owner suite is on the main floor. Second floor boasts a super large room and full bath for a guest/ family quarters. There is a beautiful livingroom with a fireplace and a family room with a fireplace and built in bookshelves. Excellent living spaces. The gracious dining room can host many a fine dining experience. The full size basement with indoor and outdoor access offers many possible uses from storage to crafts to games. A lovely sunny screen porch stretches across the back of the house with access to the kitchen and to the owners suite. A step from the porch takes you to the spa/ hot tub in it's own private setting. This home is being offered with an additional lot included. The lot affords this home access to the Kentmore Park Amenities. Beach, Piers, Boat ramp, and the Kentmore Park social association. This listing includes MLS listing # MDKE2005752, 0.11 acre lot on Anglewood Rd, Kentmore Park.

13983 Turners Point Rd, Kennedyville

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Unrepresented.

28781 Valley Rd, Kennedyville
$546,500
3 Beds ⋅ 2 Baths
Originally built in 1930. Completely updated and tastefully renovated. Perfect year round or seasonal cottage. In the very special private community of Kenmtore Park. Year round activities for all. Nightly get together at the Big Pier to capture the most beautiful sunsets on the Sassafras River. Morning coffee is served on the deck off of the kitchen. Invite friends over for a day at the beach then a casual dinner served on the secluded patio off the entertainment room. Great place also for a fire pit in the cooler months. All bedrooms are on the opposite side of the home from the entertainment room and the patio for convenient privacy. Walk to the beach or ride down on a golf car, there is always something to watch and usually someone to talk with. Kentmore is close to Galena on the North side. Visit the enchanting Cross Street Market and the Sassy market. Get take out from Twinnys or Galena Pizza. Upscale dining at the Kitty Knight or the Fish Whistle. Head South from Kentmore and come across Washington College and all the amenities of Historic Chestertown. Jump on your boat or hitch a ride on a neighbor's boat for a great day on the river. Boating, wakeboarding, skiing or tubing. Jet ski anyone? At night view the endless unobstructed sky and a million stars, planets, and the moon.

28781 Valley Rd, Kennedyville

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

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.

11955 Augustine Herman Hwy, Kennedyville
$330,000
Welcome to this spacious 2,236 square foot, 4-bedroom, 3-bath property located in the heart of Kennedyville, currently configured as a two-unit, multi-use home offering exceptional flexibility. The property can easily be converted back to a single-family 4-bedroom, 3-full-bath residence or utilized as a live/work opportunity with potential storefront space in the front unit while generating rental income from the rear apartment. The rear unit features 2 bedrooms, 2 full bathrooms including a newly added second-floor bath, a full kitchen, laundry, mudroom, and private rear entrance, while the front unit offers 2 bedrooms, 1 full bathroom, a full kitchen, laundry, and a third-floor attic that can easily be converted into additional living space with insulation and electric already roughed in. The owner has completed meticulous structural and mechanical renovations throughout the property, including new plumbing, electrical, HVAC system, roof, insulation, fresh paint, and a newly constructed large full bathroom, ensuring a move-in-ready experience. A fenced rear lot provides parking for up to six vehicles, and the home is certified lead-free. Conveniently located just 10 minutes from Chestertown and 25 minutes from Middletown, the property is also within walking distance to the Kennedyville Firehouse and popular community events such as monthly food truck nights, craft vendor shows, bake sales, and local yard sales.

11955 Augustine Herman Hwy, Kennedyville

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: RE/MAX Chesapeake.

11955 Augustine Herman Hwy, Kennedyville
$330,000
4 Beds ⋅ 3 Baths
This 2,236 sq ft, 4-bedroom, 3-bath property is a versatile live/work or investment opportunity. Currently configured as a two-unit home, it can easily convert back to a single-family residence or generate rental income from the rear apartment while utilizing the front unit as residential or potential storefront space. Each unit is fully self-contained with its own laundry area (washer/dryer) and full kitchen (refrigerator and stove/cooktop), making them highly desirable for tenants. The rear unit features 2 bedrooms and 2 baths, including a newly added second-floor bath, while the front unit offers 2 bedrooms, 1 bath, and a third-floor attic with insulation and electric roughed in for additional living space. Meticulous renovations include new plumbing, electrical, HVAC, roof, insulation, fresh paint, and a newly constructed full bathroom, ensuring a move-in-ready property. A fenced rear lot provides parking for up to six vehicles, and the home is certified lead-free. Located just 10 minutes from Chestertown and 25 minutes from Middletown, the property is near the Kennedyville Firehouse and local events like food truck nights, craft shows, and yard sales. Strong rental potential combined with turnkey upgrades makes this a smart investment for live/work or multi-family income!

11955 Augustine Herman Hwy, Kennedyville

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: RE/MAX Chesapeake.

11969 Augustine Herman Hwy, Kennedyville
$319,000
4 Beds ⋅ 2 Baths
Vintage home with lots of original details retained. 3 Staircases, 3 original fireplaces and a very grand front foyer and staircase give this home so much character! Current owners have updated it lovingly throughout. Enter through the spacious back yard, into a welcoming mudroom with a full bath on the main floor to your left and then into the updated and cozy kitchen with new dishwasher, LVP flooring, complete with the cutest back stair case! The staircase leads up to a separate home office, craft room, den, or 4th bedroom. Also downstairs is a main floor bedroom, a nice size dining room with decorative fireplace and parquet flooring, and a Living room with new carpet, and a new pellet stove to keep you warm on those chilly nights. On the 2nd level are 2 bedrooms plus the office, and a full bathroom. Full stairs to the 3rd floor leads to 2 additional rooms that could easily be finished into more living space. Since 2018 the current owners have updated the home to include: New Roof on 2 sections of house and roof repairs to existing roof (only 10 years old), all New windows (5) on third floor, encapsulated crawl space, new Oil Furnace, 2 new water heaters (one serves upstairs bathroom only). New dishwasher, blown in insulation in all internal ceilings and attic, new flooring downstairs, kitchen and bathroom updates, and so much more! Outside is a very private oasis. Completely fenced in yard with large covered side porch and open back deck looking out to a manicured lawn with large shed and nice plantings. Back gate leads to gravel driveway, parking for 2-4 cars The home is very versitile. Village zoning allows for commercial use as well. In the past it has been an antique/retail store, but please verify any possible uses with the county first.

11969 Augustine Herman Hwy, Kennedyville

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Long & Foster Real Estate, Inc..

11976 Flour Mill St, Kennedyville
$315,000
3 Beds ⋅ 2 Baths
Welcome to 11976 Flour Mill Street in the charming Village at Kennedyville! Nestled in the heart of this small-town community, this well-maintained 3-bedroom, 2-bath rancher offers comfortable one-level living with an inviting open floor plan perfect for everyday living and entertaining alike. Enjoy relaxing mornings on the welcoming front porch or unwind on the spacious back deck overlooking the backyard. Conveniently located just a short drive to Route 301 for easy northbound or southbound travel, while also being close to the historic waterfront town of Chestertown with its local shops, restaurants, and community events. If you are looking for small-town charm with convenience, this home is a must-see!

11976 Flour Mill St, Kennedyville

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

Selling Office: Unrepresented.

27741 Lambs Meadow Rd, Kennedyville
$275,000
3 Beds ⋅ 3 Baths
Original Primary School No. 3 | c.1840 | Near Kennedyville Featured in Historic Homes of Kent County Step back in time with this one-of-a-kind historic treasure — the original Primary School No. 3, circa 1840, lovingly preserved and waiting for its next chapter. Listed in Historic Homes of Kent County, this unique property sits on just under two acres, offering timeless charm, unmatched character, and rare opportunity. Set back from the road and tucked along tree-lined boundaries, the home offers exceptional privacy while evoking a deep sense of history. As you walk through the home, original details greet you at every turn — from the beloved deep window sills and antique newel post staircase to the charming fireplaces that anchor the living spaces. These historic elements are truly priceless, offering a chance to bring the past to life with your own personal vision. The property also features multiple outbuildings full of potential. One offers ample workshop space — ideal for restoring and reviving this special home. Another two-level structure could serve as an artisan’s studio, a creative retreat, or simply provide additional storage for tools and equipment. There’s even a shed with a lean-to that could comfortably house a few small animals, creating a homestead feel. Whether you're seeking a historic restoration project, a quiet country retreat, or a unique piece of Maryland's heritage, this property is a rare find — rich in character, wrapped in history, and full of promise.

27741 Lambs Meadow Rd, Kennedyville

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Doug Ashley Realtors, LLC.

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