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108 Little Harbor Way, Chestertown
$635,000
Buildable waterfront lot in the Chester River Landing community. This prime location captures panoramic views of the Chester River! Just steps away from deep water boat slips, which are available for lease or purchase. Perfect location to build your dream home on the water. The Chester River Landing community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club. Enjoy the close proximity to ample shops, dining options, and Chestertown’s year-round farmers market.

108 Little Harbor Way, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

21590 Pine Ln, Rock Hall
$624,900
1 Beds ⋅ 1 Baths
Exceptional custom live/work space located on 5 acres at the entrance of Rock Hall. Newly constructed in 2019. This home boasts a screened porch, open living space with hardwood floors, encapsulated crawl space, metal roof, efficient ductless mini-splits, and sophisticated vaulted ceilings. This professional artist studio was completed with architectural lighting, seamlessly lighting the space for the everyday or a special occasion. Currently used as an artist studio, this home and property have the potential to be whatever you desire. The open living space would make an inviting home, perfect for entertaining. The tucked-away loft bedroom is spacious and has exceptional views of the surrounding woods. There is plenty of room on the 5-acre parcel to expand or customize! Prime location with tons of privacy. This gem is tucked away, yet just a short jaunt to all Rock Hall has to offer: marinas, restaurants, Main Street shops, public boat launches, and the Ferry Park beach! Showings by appointment only.

21590 Pine Ln, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

21191 W Sharp St, Rock Hall
$610,000
3 Beds ⋅ 3 Baths
Welcome to 21191 West Sharp Street - conveniently located just a few steps from downtown Main Street and the Rock Hall Marinas, this 1920s craftsman has recently undergone a remarkable renovation from top to bottom. Taken down to the framing and expanding upon the existing square footage, it was completely rebuilt by a reputable local builder. No surface was left untouched! Several interior walls were removed for a new modern open-floor layout with elevated ceilings. The exceptional construction quality, a main floor primary suite and practical indoor / outdoor living spaces make this the perfect home for everyday living or a weekend retreat. A few of the outstanding features include: coffered ceilings, thick crown moldings and railings, dark hardwood floors, plantation shutters, double wine bar, a Wolf kitchen range, a conditioned two-car garage, screened-in porch, a copper water line, the list goes on. The home was also fitted with dual mini-split systems and a large Rinnai instant hot water heater: both energy efficient and budget friendly! As you enter you are greeted by a spacious living room and dining room combination which naturally flow into the modern kitchen. Finished with granite countertops, ceramic tile backsplash, and Wolf and GE appliances, The first floor primary bedroom with large ensuite bath enables one to enjoy all one floor living should they desire. A double chilled wine bar and powder room behind the kitchen complete the first floor living area. Moving upstairs, there is a generously sized living space in the front and two full bedrooms behind in the newly added dormers. A new full bath with ceramic tile flooring and shower, and stone vanity further complements the upstairs living space. Moving to the back of the house; the screened-in porch is perfect for summertime crabs feasts and the propane fire pit is great for summer evenings with friends and family. Plenty of parking in the back driveway or in the two-car garage which is heated, air conditioned and spray-foam insulated. A quick walk to Java Rock for a morning coffee or an easy stroll to the Marina’s or the beach. Rock Hall is a vibrant town with many great restaurants, a brewery, and many festivals like Pirates and Wenches and Fall Fest. You dont want to miss this remarkable home.

21191 W Sharp St, Rock Hall

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

21008 Rock Hall Ave, Rock Hall
$599,900
3 Beds ⋅ 2 Baths
New construction opportunity in Rock Hall with time to make it your own. The current plans feature a 1,650-square-foot ranch-style home with 3 bedrooms, 2 bathrooms, a front porch, and rear deck, all situated on a .79-acre lot within town limits. The open living areas include a large kitchen with white cabinetry, quartz countertops, stainless steel appliances, and upgraded LVP flooring that continues through the living and dining rooms. The primary bedroom features a walk-in closet and en-suite bathroom with dual vanity and shower. Two additional bedrooms have upgraded carpet and share a guest bathroom with a tub/shower. Additional features include an energy efficiency heat pump, a conditioned crawl space and public water and sewer. There is still time to select finishes and add your own personal touches. Buyers may also have the option to make changes to the current plans or choose a different style of home, subject to new permit approval. Located just two blocks from Rock Hall Harbor and close to Haven Harbour and Swan Creek, the property puts boating, marinas, restaurants, shops, and the waterfront all within easy reach. It’s a convenient in-town location for enjoying the laid-back, waterfront lifestyle that makes Rock Hall such a popular Eastern Shore destination.

21008 Rock Hall Ave, Rock Hall

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

14200 Metasequoia Ct, Galena
$595,000
It is a rare opportunity for a private waterfront lot off the Sassafras River to come available. This 14 acre parcel of land is located above the bridge in a well established small community of Gentle Winds. Scenic and tranquil area for birding watching, kayaking or taking a short boat ride to restaurants located down the river. With this 14 acre lot, there are open areas and woods to play with. Build the house of your dreams and be able to work and play where you live. Short drive to tax free shopping in Middletown DE. It appears that this property is allowed to have an in-law suite as a separate living area, note the letter from Gentle Winds HOA, Also the Kent county has their assessment. The Hoa, will need to review plans and etc. as before.

14200 Metasequoia Ct, Galena

Listing courtesy of Gunther-McClary Real Estate. Contact:

12118 Still Pond Creek Rd, Worton
$585,000
4 Beds ⋅ 3 Baths
Welcome to your dream home in Worton, MD! This stunning center hall Colonial-style property boasts 4 bedrooms, 2.5 bathrooms, and sits on over 6 acres of picturesque land. As you approach the home, you'll be greeted by a charming circular driveway and an oversized detached 2 car garage, perfect for storing all your vehicles and outdoor equipment. Inside, the home features beautiful hardwood floors throughout, adding warmth and character to the space. The kitchen is a chef's delight, with soapstone countertops, gas cooking and ample cabinet space for all your culinary needs. Cozy up by the fireplace; perfect for relaxing on chilly evenings. This property has a metal roof and owned solar panels, allowing for energy-efficient living and potential cost savings on utilities. With a shed for additional storage and plenty of space to roam on the expansive grounds, this property offers the perfect blend of comfort and tranquility and just a short drive to Chestertown. Don't miss your chance to make this idyllic retreat your own – schedule a showing today!

12118 Still Pond Creek Rd, Worton

Listing courtesy of Patterson-Schwartz-Hockessin. Contact:

21309 E Sharp St, Rock Hall
$585,000
This 10,000 SF commercial building presents a prime investment opportunity with significant investment potential. Located on an irregularly shaped parcel, the property offers flexibility for various development options, making it ideal for investors looking to capitalize on future growth. Built in 1955, the structure requires major rehabilitation, allowing for customization to meet market demands. The building features durable brick and aluminum facia on block construction. Concrete and hardwood flooring provide a solid foundation for redevelopment. Ample paved parking enhances accessibility, attracting potential tenants or customers. With no current association fees or amenities, investors can maximize their profit. The expansive size and strategic location position this property for various commercial uses, from retail to mixed-use developments. Seize the opportunity to transform this property into a lucrative asset in a growing market. A buyer is responsible to confirm all details and uses of the property.

21309 E Sharp St, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

1 Bayview Rd Unit 12B, Betterton
$565,000
3 Beds ⋅ 2 Baths
Waterfront condo in Rigbie Bluff with elevated, unobstructed waterfront views! This second-floor unit offers two levels of comfortable living with beautiful Chesapeake Bay views from multiple rooms. The main level features an updated kitchen with cherry cabinets and granite countertops, dining area, and living room overlooking the Bay. A flexible bedroom/sitting room with wet bar and water view, Jack-and-Jill bath with tub and laundry, and second bedroom complete this level. Upstairs, the spacious loft offers additional living space, skylights, and another great Bay view. The primary suite features a generous closet, en-suite bath with walk-in shower, and private deck - just the spot to enjoy your morning coffee or watch the sunrise over the Bay. Enjoy the community pool, private dock, deeded boat slip with an 8,000-lb boat lift, and a private basement with exterior access for plenty of storage. The condo association has completed numerous improvements in recent years, including new siding, decking, and stairs where needed. Located in Betterton, “The Jewel of the Chesapeake,” with the beach, pier, boardwalk, and park nearby. A wonderful opportunity to enjoy elevated, unobstructed waterfront living, boating, and all that this charming Chesapeake Bay town has to offer!

1 Bayview Rd Unit 12B, Betterton

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

25124 E Kentfield Rd, Worton
$565,000
3 Beds ⋅ 3 Baths
Light-filled home with glowing wood floors, exposed beams, skylights, and open living space. This one-level home is nestled on just under two acres! The expansive yard offers room for many activities and provides scenic views from the home. Inside, the open living space is bright and airy, with skylights, bay windows, and vaulted ceilings with exposed beams. The large kitchen has beautiful updated granite countertops, a large pantry, kitchen island with seating, and ample cabinet space. From the dining room you can explore the raised deck with a hot tub! Or enjoy meals on the screened porch, finished with water and electricity. This one-level home boasts 3 spacious bedrooms and 2.5 bathrooms. The primary bedroom has a walk-in closet and opens to a sun-filled studio or office space, which has access to the raised deck. There is an attached two-car garage with ample storage space, which could also make a great workshop. Under 15 minutes to downtown Chestertown and less than an hour to Middletown DE. This home is move in ready! The sellers are selling turn-key with contents. Recent updates include: -Refinished hardwood floors throughout home -Granite countertops in kitchen -Updated kitchen appliances -Water treatment system - & more! Solar leased through Tesla

25124 E Kentfield Rd, Worton

Listing courtesy of Gunther-McClary Real Estate. Contact:

12613 Walnut Valley Ct, Worton
$559,500
3 Beds ⋅ 2 Baths
There's a joyful feeling here that takes you straight back to childhood summers on the water. The Kinnairds Point community and property itself delivers this on just over two private acres at the end of a quiet cul-de-sac in Worton. Fully remodeled in 2020, the home opens into a vaulted great room with an exposed beam ceiling and a brick fireplace, flowing into a gorgeous, move-in-ready kitchen finished in crisp white cabinetry and a farmhouse sink. The owner's suite offers a spacious walk-in closet and an amazing renovated bath, while a screened porch and picnic lawn keep everyday living just as easy outdoors. The screened porch is designed for sharing beautiful moments and taking in nature. The full basement allows you to keep all of your "toys" tucked away while still keeping your cars in the garage. Best of all, Kinnairds Point offers access to two private Chesapeake waterfronts each with its own beach, pavilion, and kayak storage, one with a boat ramp just a walk or golf cart ride from your door. Crab pots, boat cruises, and sunset chairs are all in your future. Come life the Eastern Shore lifestyle in a polished setting just minutes from Historic Chestertown.

12613 Walnut Valley Ct, Worton

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

5666 Walnut St, Rock Hall
$550,000
3 Beds ⋅ 2 Baths
Rare opportunity to purchase five contiguous parcels totaling 3.765± acres in a prime location near Rock Hall Harbor. Parcel 505 features an older manufactured home situated on approximately 1.27± water-view acres with scenic views of North Point Marina and Rock Hall Harbor. The additional parcels include Parcel 504 (0.853± acres), Parcel 503 (1.04± acres), Parcel 502 (0.258± acres), and Parcel 501 (0.344± acres), offering endless possibilities for expansion, investment, or future development (subject to applicable approvals). The existing home offers over 1,200 square feet of one-level living with three bedrooms and two full baths. While the home is in need of renovation and repairs, it presents an excellent opportunity to create a charming vacation retreat, retirement home, or investment property in a highly desirable waterfront community. The property is being sold As-Is. The lots are cleared and level, providing a fantastic setting to enjoy all that Rock Hall has to offer.

5666 Walnut St, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

21090 W Sharp St Unit 133, Rock Hall
$545,000
3 Beds ⋅ 2 Baths
Experience the allure of waterfront living with this stunning condominium, perfectly situated to offer breathtaking views of the Chesapeake Bay and the Rock Hall Harbor. Inside, you are greeted by an inviting ambiance, accentuated by updated kitchen and flooring that seamlessly blend style and functionality. Whether you’re an aspiring chef or simply enjoy the art of entertaining, the modern kitchen is designed to inspire culinary creativity, boasting stainless steel appliances and ample storage space. Just up the stairs you will find two large guest bedrooms, washer and dryer, and a full bathroom. The primary bedroom is located on the third level with a view of the Bay. You'll love the large private balcony overlooking the Chesapeake. The primary bathroom has a soaking tub as well as a shower, and a walk-in closet with ample space for storage. This residence is located a short stroll from marinas, a vibrant array of restaurants, and downtown shops. Easy access to festivals throughout the summer and fall, enjoy a delightful day out or a cozy evening at your favorite eatery. The charm of this location is not just limited to daytime adventures; it transforms into a magical setting at night! The best part is the unobstructed views of spectacular 4th of July fireworks, all from the comfort of your own home. This condominium offers relaxation and convenience while taking in all the charms of Rock Hall. With a focus on comfort, every corner is thoughtfully designed to cater to your needs, blending modern amenities with the natural beauty of its surroundings. Don’t miss the opportunity to make this beautiful condominium your own! Embrace the coastal lifestyle and let the Chesapeake Bay become your new escape.

21090 W Sharp St Unit 133, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

12200 Azalea Ct, Worton
$535,000
3 Beds ⋅ 3 Baths
Custom-built rancher situated on more than 1.8 acres in the Kentfield community of Worton. Designed for one-floor living, the home offers a spacious, functional layout along with an unfinished basement that provides plenty of room for storage, a workshop, or other possibilities. The large kitchen features a breakfast area, generous cabinet and counter space, and a center island with propane cooktop. The living room includes built-in cabinetry, a propane fireplace, and a slider door leading to the screened porch overlooking the private backyard. The living room opens to the dining area and entry, creating an easy flow through the main living spaces. The primary suite includes an en-suite bath with two walk-in closets, dual vanities, a separate shower, and jetted tub. Two additional bedrooms share a full hall bath, while a separate office offers flexible space and could serve as a fourth bedroom. The two car, side entry garage has access to the basement. Outside, the large backyard is surrounded by mature trees and includes split-rail fencing, a storage shed, and covered pergola. The 1.8+ acre lot offers plenty of room for a future pool, larger outbuilding, gardens, or additional outdoor living space. Located near Still Pond Creek and just five minutes from Worton Elementary School and Kent County High School, the property offers a peaceful setting while remaining convenient to both Chestertown and Rock Hall. Middletown, Delaware is approximately 35 minutes away. Schedule a showing today.

12200 Azalea Ct, Worton

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

13984 Mill Creek Ln, Galena
$535,000
4 Beds ⋅ 2 Baths
Home Sweet Home. How Sweet it is! Rustic Log cabin 4 Bedrooms, 2Baths. Front and rear porches, In ground Pool, 3 Car detached garage, 24X 34 detached metal building. Great for all the toys, Shop, or Storage. Mature Landscaping, All Situated on 9.28 Acres located close to the Sassafras River. Wow! Call for your private showing.

13984 Mill Creek Ln, Galena

Listing courtesy of Key Realty, Incorporated. Contact:

12712 And 12714 Still Pond Rd, Still Pond
$519,900
Invest with confidence in this amazing duplex opportunity just minutes from Historic Chestertown and the pristine Betterton Beach. Get your entrepreneurial juices flowing because the income opportunity with this property makes it irresistible. You can live in one side and largely get your mortgage paid for you by renting out the other side. You can rent both and enter an easy cash flow situation at a great price. This property also provides for a perfect multigenerational household. The garage is another amazing plus with a kitchenette, full bathroom and loft for a private office or area for grandkids to roughhouse. Surround yourself with a great sense of community and bucolic farm landscapes. The rear yard includes a hot tub, amazing hardscaping for family gatherings and a view that opens out to peaceful farm fields. Sit in the sunroom at 12712 Still Pond Road and truly understand the quality of life that comes with country living. This is one not to be missed.

12712 And 12714 Still Pond Rd, Still Pond

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

12712 And 12714 Still Pond Rd, Still Pond
$519,900
6 Beds ⋅ 6 Baths
Invest with confidence in this amazing duplex opportunity just minutes from Historic Chestertown and the pristine Betterton Beach. Get your entrepreneurial juices flowing because the income opportunity with this property makes it irresistible. You can live in one side and largely get your mortgage paid for you by renting out the other side. You can rent both and enter an easy cash flow situation at a great price. This property also provides for a perfect multigenerational household. The garage is another amazing plus with a kitchenette, full bathroom and loft for a private office or area for grandkids to roughhouse. Surround yourself with a great sense of community and bucolic farm landscapes. The rear yard includes a hot tub, amazing hardscaping for family gatherings and a view that opens out to peaceful farm fields. Sit in the sunroom at 12712 Still Pond Road and truly understand the quality of life that comes with country living. This is one not to be missed.

12712 And 12714 Still Pond Rd, Still Pond

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

11960 Flour Mill St, Kennedyville
$515,000
7 Beds ⋅ 5 Baths
Welcome to 11960 Flour Mill Street. This is the perfect house for a growing family or a multi-generational household. Main House has 6 full bedrooms and 4 full bathrooms while the second floor above the garage is a spacious mother-in-law suite with a separate entrance, efficiency kitchen, full bath and walk-in closet. First floor has a bedroom and full bath and wide open floor plan in the kitchen and living rooms. Kitchen features stainless steel appliances, granite countertops and wood cabinets. Second floor has 5 bedrooms and 2 full baths. Partially finished full basement has another full bathroom and offers a range of possibilities for the next owner. This home has more room and storage than you could imagine. The Villages at Kennedyville is a quiet, local community. Less than 90 minutes to Philadelphia and Washington D.C. 30 minutes to Middletown, Delaware and tax-free shopping. Close to Turners Creek State Park, Betterton Beach and the restaurants/marinas in Galena on the Sassafras River. Just a few minutes to historic downtown Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals and an award-winning weekly Farmer's Market. Seller will convey a brand new Carrier HVAC unit with the sale to replace the first floor one.

11960 Flour Mill St, Kennedyville

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

103 Sutton Way, Chestertown
$509,000
5 Beds ⋅ 4 Baths
103 Sutton is perfectly situated just a stone’s throw from the vibrant heart of Downtown Chestertown. This exquisite 4+ bedroom residence is designed to cater to the diverse needs of today’s Buyers, offering a harmonious blend of comfort, style, and functionality. This home is ideal for those upsizing or seeking multi-generational living. * Originally built as the community model home – and meticulously maintained since – it has ALL the extras: generous breakfast nook bump out, gas fireplace, gleaming hardwood floors, upgraded carpet, oversized windows, granite countertops, stainless appliances, dedicated home office, and a finished basement with a full bath and expansive wet bar. * As you step inside, you’ll be greeted by a two-story foyer flooded with light, dining room and den or family room. The gourmet kitchen that is a chef’s paradise, featuring high-end appliances, custom hardwood cabinetry, and a small island for an ideal triangle of space for meal prep. The open concept layout flows effortlessly into the breakfast nook and living room, providing the perfect setting for family gatherings and celebrations with friends. Click on the propane fireplace for a cozy night watching the sunset or snow flurries outside the tall windows. * The spacious primary suite is an escape through a double door entry – featuring a lighted tray ceiling, a large walk-in closet, en suite bath with soaking tub, glass shower, and a separate water closet. Three additional bedrooms all have custom trim work, generous closets, and large windows. * The finished basement is a standout feature, complete with a stylish wet bar with stone walls that transforms it into the ultimate entertainment zone, perfect for hosting game nights or movie marathons. The backyard feels private with mature trees and a gentle slope, ideal for play space. * The proximity to local parks, playgrounds, restaurants, and shopping ensures that all your family’s needs are met within minutes. Additionally, the Coventry Farms neighborhood fosters a sense of community all while being a convenient distance from Middletown, DE, Philadelphia, PA, Washington DC, Baltimore, MD, and points beyond. * This home is not just a place to live; it’s a lifestyle waiting to be embraced. Don’t miss the opportunity to make this stunning property your own. Schedule your private tour today and experience firsthand what this exceptional home has to offer.

103 Sutton Way, Chestertown

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

201 N Lynchburg St, Chestertown
$500,000
A great opportunity for community mission driven organizations. The church and 5 additional parcels are all offered separately or together. Located in the heart of Chestertown, this charming church of a little over 3,500 square feet offers a unique opportunity for continued use as a place of worship, community gathering space, or potential conversion. The property features wheelchair accessibility, on-site parking, and a layout ideal for a variety of uses. With its peaceful setting and classic structure, this building is ready to serve its next purpose. Also available with mls MDKE2006846 additionally

201 N Lynchburg St, Chestertown

Listing courtesy of RE/MAX Associates-Hockessin. Contact:

331 Devon Dr, Chestertown
$499,999
4 Beds ⋅ 4 Baths
Welcome to 331 Devon Drive in Family friendly Coventry Farms. With 4 bedrooms and 3.5 bathrooms, this recently updated and meticulously maintained Colonial home offers enough space for the whole family and a harmonious blend of convenience and elegant living. The owners have an assumable VA Mortgage below 4.5% The well-designed first floor - featuring tall ceilings, new dimmable recessed lighting and a wood burning fireplace - is anchored by the open-concept kitchen and living room spaces, which flow naturally to the exterior deck. The upgraded gourmet kitchen is a chef's dream, featuring upgraded countertops, stainless steel appliances, and a spacious island that invites culinary creativity. The kitchen flows effortlessly into the family room, where a cozy fireplace serves as the focal point, perfect for gathering with loved ones. The back of the house flows easily through sliding glass doors to the large back deck overlooking a large community open space with trees and a rolling field. A formal dining room off the kitchen and a large office space complete the first floor. Moving upstairs, there is brand new carpet throughout all four bedrooms. The master suite is a true retreat, complete with a walk-in closet and an en-suite bathroom. The attached garage accommodates two vehicles, while the paved driveway provides additional parking for guests. An electric vehicle charging station is great for those with an EV. The finished walkout basement with a full bathroom is a large open space offering possibilities for a second living room, home gym, entertainment area, etc. A Sunrun Solar system has significantly reduced the home's electric bill. Recent upgrades include: GE Profile SS kitchen appliances, deep farm-style sink, Trane heating / air air system, recessed lighting, fans, second floor carpet, interior and exterior paint throughout and more. Coventry Farms is just a couple minutes from downtown Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic architecture, local shopping, restaurants, art galleries, and waterfront parks. Home to many festivals, an award-winning weekly Farmer's Market, Chestertown has a laid-back lifestyle with an endless number of social or volunteer activities. Less than 90 minutes to Washington D.C. or Philadelphia. Enjoy country living on the Eastern Shore. More photos and information to come!

331 Devon Dr, Chestertown

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

25133 Wymont Park Rd, Worton
$499,000
1 Beds ⋅ 2 Baths
Welcome to Wymont Park, a sought-after waterfront community on picturesque Still Pond Creek, where every day feels like a vacation on Maryland's Eastern Shore. From sipping your morning coffee while watching the sunrise over the water to enjoying breathtaking waterfront sunsets from your private floating dock, this unique property offers the lifestyle you dream about. Nestled on a beautiful waterfront lot, this versatile property features two separate living spaces, making it ideal for multi-generational living, guest accommodations, or potential rental opportunities. The charming waterfront cottage offers 1 bedroom, 1 full bath, and 1 half bath, highlighted by a spacious living room with cathedral ceilings and panoramic views of Still Pond Creek. The kitchen provides abundant cabinet and counter space, making it perfect for entertaining. Adding even more value is the oversized detached garage with a fully equipped second-floor apartment, complete with 2 bedrooms, a full kitchen, living room, and full bath. Whether you're hosting extended family, accommodating guests, or creating a private workspace, this additional living area offers endless possibilities. Step outside and discover what truly makes this property special. A large wraparound deck leads to a gazebo, creating the perfect place to relax and take in the peaceful creek views. Follow the path to your private floating dock, ideal for boating, kayaking, fishing, crabbing, paddleboarding, or simply enjoying life on the water. Located in one of Kent County's most desirable waterfront communities, this property offers the perfect combination of privacy, natural beauty, and Eastern Shore charm. Whether you're searching for a full-time waterfront residence or weekend getaway, this rare waterfront property is ready for its next owner to make it their own. Don't miss your chance to own a piece of Maryland's Eastern Shore waterfront lifestyle on Still Pond Creek.

25133 Wymont Park Rd, Worton

Listing courtesy of RE/MAX Chesapeake. Contact:

14136 Kentmore Park Rd, Kennedyville
$499,000
4 Beds ⋅ 2 Baths
Amazing waterfront community on the Sassafras river. This Kentmore Park home was originally built in 1953. Major renovation in 2006 adding bedrooms, bathroom, basement, large light filled gathering room. The rear deck has space for outdoor dining and privacy. The perfect year round get away or primary residence. Well maintained. Four bedrooms and two baths. Lower level garage and walk out basement. Enclosed lawn and yard equipment storage space. Rear yard gathering area and room for a garden. Lovely pastoral view of farmland. Easy path to beach and central Kentmore Park Community areas. Tax free shopping in Delaware. Convenient shopping in Galena. Check out Cross Street Market for produce, local meat, specialty foods, plantings and friendly faces. Explore Jones Farm for local meats and ice cream. Event space for special occasions, pumpkin patch and seasonal surprises. Convenient Sassy Market for deli, fresh meat and the perfect snacks and beverages. Galena has fine and casual dining, pizza and delicious steak sandwiches. You are close to Historic Chestertown with casual and special dining, eclectic shopping, Chestertown Golf and Country Club, waterfront access, fishing and boating opportunities. Cruise the Chester River on the Packet for an adventure or special celebration. Visit historical buildings. Enjoy weekend activities in History Park in the center of town, farmers market, Tea Party, Crazy Days sales and more. Never a dull moment. Chestertown is full of history including Washington College and the Chestertown Tea Party Reenactment. This home offers so much not to mention lazy days on the beach, water sports, sailing, power boating, jet skis. Friendly and welcoming neighbors, gathering at the pier for taps and the sunset. Living the Life! Kentmore Park was established in the late 1940 era. Started mainly as a sailing community for weekend and summer enjoyment. Now a very active community with year round social events as many familys have expanded their time in Kentmore beyond spring, summer and fall. A mix of full time and part time residents. All ages are represented. There is a social club with $350.00 yearly dues. There are many activities with the Kentmore Park Improvement Association (KPIA) for all ages. Easy travel to points north and south. PA, NJ, DC. Easy day trip to Annapolis, Easton, St. Michaels.

14136 Kentmore Park Rd, Kennedyville

Listing courtesy of Gunther-McClary Real Estate. Contact:

10 Cedar Chase Ct, Chestertown
$495,000
3 Beds ⋅ 3 Baths
Beautiful waterviews of the Chester River set the stage for this special Chestertown property, located in desirable Mile Tree Village and just a short walk from the Historic District. Set on .53 acres, the home offers 1,656 square feet of finished living space on the main level, with 3 bedrooms and 2 full baths, plus an unfinished lower level with a half bath and one-and-a-half-car garage. An upper-level deck, accessible from the living room, dining room, and primary suite, provides the perfect spot to enjoy the river views and the easy Eastern Shore lifestyle. The home is ready for a fresh vision and offers tremendous potential to become a luxury waterview residence. Thoughtful updating could transform the existing spaces into a home that takes full advantage of the setting. Within a short walk or bike ride to Chestertown's Historic District for dinner, shopping, galleries, and Annual Festivals, while the Chester River provides a beautiful backdrop to everyday life. Bring your vision and create a truly special waterview home and experience the Eastern Shore Lifestyle at its finest!

10 Cedar Chase Ct, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

16 Howell Point Rd, Betterton
$487,000
3 Beds ⋅ 3 Baths
SELLER-PAID 2-1 INTEREST RATE BUYDOWN AVAILABLE! Make homeownership more affordable with lower mortgage payments for the first two years! For example, based on an assumed 7.75% interest rate, buyers could enjoy a 5.75% rate in Year 1 (approximately $500/month savings), 6.75% in Year 2 (approximately $250/month savings), and 7.75% beginning in Year 3. That’s potentially $9,000 in savings over the first two years! Buyers may also have the opportunity to refinance if rates decrease, although refinancing is not guaranteed. Example only. Actual rates, payments, savings, and eligibility depend on loan terms and lender approval. Buyers must qualify at the full note rate, subject to lender requirements. Contact your lender for details. Welcome to 16 Howell Point Road in Betterton, Maryland, where small-town Eastern Shore charm meets comfortable living just a few blocks from beautiful Betterton Beach! This inviting 3-bedroom, 3-bath home offers plenty of space inside and out. The full walk-out basement is partially finished, providing additional living space with endless possibilities for a family room, home office, recreation area, guest space, or workshop. Step outside onto the back deck overlooking the fenced-in backyard, perfect for pets, entertaining, gardening, or simply relaxing at the end of the day. The large driveway provides plenty of parking, while the spacious backyard offers room to enjoy the outdoors. One of the home’s best features comes each evening—gorgeous sunsets stretching across the rolling hills and surrounding farmland, creating a peaceful Eastern Shore backdrop right from your own backyard. Located just blocks from Betterton Beach and the Chesapeake Bay, you’ll have easy access to swimming, boating, fishing, kayaking, and everything that makes this waterfront community such a special place to call home. Whether you’re searching for a full-time residence, weekend getaway, or Eastern Shore retreat, 16 Howell Point Road is ready to welcome you home!

16 Howell Point Rd, Betterton

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

129 Trafford Dr, Chestertown
$480,000
3 Beds ⋅ 3 Baths
PICTURES COMING SOON Welcome home to this beautiful 3-bedroom, 2.5-bath residence in the charming town of Chestertown, MD. Designed for both comfortable living and effortless entertaining, this home offers spacious interiors filled with abundant natural light. The main level features a bright kitchen with Breakfast Bar that flows seamlessly into a sunny Florida room, creating the perfect space to enjoy your morning coffee or unwind while overlooking the backyard. You'll also find a formal dining room for hosting special occasions, a welcoming living room, and a cozy family room that provides plenty of space for everyday living. Downstairs, the finished basement offers versatile additional living space ideal for a recreation room, home theater, fitness area, playroom, or home office. There is enough space to do all of it. The unfinished area has full laundry and ample storage. Upstairs, the expansive owner's suite serves as a private retreat, complete with a generous walk-in closet and an ensuite bathroom featuring a soaking tub. Two additional bedrooms each offer large closets and ample space for family, guests, or a home office. A full bathroom conveniently located off the second-floor sitting area completes the upper level. Step outside to your own private backyard oasis. The landscaped yard features a refreshing in-ground swimming pool with a new tile finish and a new filtration system, making it ready for years of enjoyment. A new deck with a privacy wall extends from the home, providing the perfect setting for outdoor dining, entertaining, or relaxing poolside. Additional highlights include a large storage shed and a newly installed rock bed surrounding the pool deck that enhances both beauty and low-maintenance landscaping. For added peace of mind, the home also features a roof that is only two years old. Combining spacious living areas, thoughtful updates, exceptional outdoor amenities, and a desirable location in historic Chestertown, this home truly has something for everyone. Don't miss the opportunity to make this exceptional property your next home!

129 Trafford Dr, Chestertown

Listing courtesy of Elevated Real Estate Solutions. Contact:

21251 Chesapeake Ave, Rock Hall
$480,000
5 Beds ⋅ 2 Baths
Beautifully updated while preserving its character, this charming home is ideally located just a short distance from the Rock Hall Harbor and Chesapeake Bay, offering easy access to waterfront dining, boating, and all the coastal charm Rock Hall has to offer. Relax on the spacious front porch, or entertain on the screened porch, complete with electricity and plenty of space for outdoor dining. Inside, the home seamlessly blends original character with thoughtful modern updates. The large country kitchen retains its classic charm while featuring updated stainless steel appliances. Off of the kitchen you’ll find the formal living and dining rooms, highlighted by beautiful built-in cabinetry and warm original hardwood floors that extend throughout the home. This home offers a first-floor bedroom and an updated full bathroom, offering hard-to-find single-level living. Upstairs there are four additional bedrooms and a second full bathroom, providing plenty of room for family, visitors, or a home office. The large backyard is adjacent to the civic center, providing lots of open space, yet lined with trees for privacy. Filled with warmth, charm, and modern comforts, this beautifully maintained home offers the perfect opportunity to enjoy life in one of Maryland's most beloved waterfront communities. Short distance to Main Street shops, many restaurants, marinas, and the Rock Hall beach. Brand new roof! This home is move in ready! The sellers are selling turn-key with contents.

21251 Chesapeake Ave, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

105 N Water St Unit 3, Chestertown
$459,000
2 Beds ⋅ 2 Baths
Second story, waterfront condo in historic Chestertown. Comes with a private boat slip at the end of the dock. 2 bedrooms and 2 full baths. Spacious patio with a stunning view of the Chester River. One of the most coveted streets in historic Chestertown!

105 N Water St Unit 3, Chestertown

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

21111 Chesapeake Ave, Rock Hall
$449,000
This beautiful waterfront lot consists of 95 feet of water frontage. It has a 90 foot pier and can hold 8 boats in 6+ feet of water. Water and Electric are available on site. This property is part of Rock Hall Harbor. It is located in the Maritime Water-Dependent Zoning District.

21111 Chesapeake Ave, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

31923 River Park Rd, Millington
$435,000
3 Beds ⋅ 2 Baths
Charming waterfront rancher on the Chester River! This move-in ready home features 3 bedrooms, 1.5 baths, and luxury viny plank flooring throughout. Recent upgrades include all-new appliances (2021), a 12' x 20' shed/workshop (2023), and new HVAC and viny siding (2024). Step outside to a spacious deck overlooking the river and your private dock--perfect for fishing, launching kayaks, or docking a small boat. Conveniently located just 15 minutes from both Chestertown, MD and Middletown, DE, this waterfront retreat offers the ideal blend of comfort, convenience, and outdoor enjoyment. A must-see!

31923 River Park Rd, Millington

Listing courtesy of RE/MAX Chesapeake. Contact:

10781 Fermoy Rd, Chestertown
$429,500
4 Beds ⋅ 3 Baths
Seller is offering a credit of up to 2% of the purchase price toward the buyer's interest rate buydown with an acceptable offer, a real financial advantage on this updated Cape Cod in the Chesapeake Landing community. Buydown subject to lender approval and buyer qualification. Welcome home to relaxed Eastern Shore living in the waterfront community of Chesapeake Landing. This beautifully updated 2,140 sq ft Cape Cod offers the perfect blend of charm and modern comfort with 3 bedrooms, 2.5 baths, and a welcoming floor plan designed for everyday life. The main level features new flooring throughout, a spacious living area, formal dining room, and a renovated country kitchen with new appliances, new counters, and plenty of space for gathering. A main-level bedroom adds flexibility for guests or one-level living. Enjoy morning coffee or evening sunsets on the back deck overlooking the open, cleared 0.39-acre lot—perfect for gardening or outdoor fun. Additional highlights include a 2-car garage and access to community amenities with a beach, fishing pier, and pavilion. Just minutes from historic downtown Chestertown, you’ll love being close to local shops, dining, marinas, and all the charm of Eastern Shore living.

10781 Fermoy Rd, Chestertown

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