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$363,000
3 Beds ⋅ 3 Baths
Welcome to Galena a little big town. Located just down the road from the Sassafras River this area has excellent access to the Chesapeake Bay, shopping, restaurants and more. With just about an hours drive you can be in Baltimore, Philadelphia or Annapolis. What an opportunity to build instant equity. Spacious home in great community, backing to farmland. This home is located in the community, but not within town limits. Enjoy public utilities without the town tax! Home has been maintained over the years, featuring new HVAC less than a year ago as well as roof replacment 10 years ago. Nicely laid out with living room, dining room, eat in kitchen, laundry room, powder room and great family room on the main level. The second level has a primary suite with loft, two additional bedrooms and hall bath. There is also a nicely proportioned two car attached garage. Home will benefit from updating to make it your own.

206 Maplewood Ln, Galena

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

$315,000
3 Beds ⋅ 1 Baths
Here is 24775 Langford Road, a well-maintained 3-bedroom, 1-bath home situated on 1.27 acres in a peaceful country setting just minutes from downtown Chestertown. The property features a spacious two to three-car detached garage/workshop, offering plenty of room for vehicles, storage, hobbies, or projects. A large Trex deck provides additional outdoor living and entertaining space. The home underwent extensive renovations in 2018, including the roof, windows, siding, gutters, storm doors, HVAC system, the Well was done in 2021, and partial crawl space encapsulation. Interior improvements included refinishing of the original hardwood floors and a remodeled kitchen featuring all-wood cherry cabinetry and stainless-steel appliances. With numerous major improvements already completed, garage and workshop space, and over an acre of property, this home offers comfortable country living with convenient access to Chestertown, Rock Hall and surrounding areas.

24775 Langford Rd, Chestertown

Listing courtesy of RE/MAX Chesapeake. Contact:

$1,195,000
2 Beds ⋅ 1 Baths
Remarkable downtown Chestertown development opportunity outside the Historic District. Incredible potential for a builder or a unique property for a private homesite. Directly adjacent to the Chestertown walking rail trail and just steps from downtown Chestertown while overlooking the Lawrence Wetland Preserve, rolling meadows and Radcliffe Creek behind. Sale includes two parcels - 302 S Mill (.45 acres) and 300 S Mill (.55 acres) - totaling approximately 1 acre. 300 is unimproved and 302 has a 1960s brick home on it. R:6 Traditional Neighborhood Development Zoning permits a wide range of dense residential development opportunities. Maximum residential density is limited to 42 bedrooms which could be single family homes, multi-family, apartments, townhouses, rowhouses, condos, and others. Smaller commercial options available as well. Public water and sewer is on site and additional allocations are available. Entire site is usable. Property is partially wooded with several large mature Oak Trees. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market. Additional information available upon request. Buyer to perform own due diligence. Do not enter property without and appointment.

302 S Mill St, Chestertown

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

$649,000
4 Beds ⋅ 3 Baths
Welcome to this beautifully crafted home in the water-oriented community of Great Oak Estates, just outside of Chestertown on Maryland’s Eastern Shore. Nestled in a peaceful setting that backs to woods alive with songbirds and butterflies, this high-quality residence offers an easy-flow floor plan designed for both lively gatherings and quiet private moments. A soaring two-story foyer greets guests and opens to the living room and family room, the latter featuring built-in cherry cabinets and a cozy propane fireplace. The formal dining room connects seamlessly to the kitchen and an additional casual dining space, making entertaining effortless. The kitchen showcases handmade cherry cabinetry and a brand-new refrigerator. Hardwood floors run throughout the main living areas, while brand-new carpeting softens every bedroom. On the main level, the primary suite includes its own bathroom, a walk-in closet, and plantation shutters. A second main-floor bedroom (ideal as a guest room or home office) shares convenient access to the hall bath. Completing the first floor are a large walk-in pantry and a laundry room outfitted with a brand-new washer and dryer. Upstairs you’ll find two additional spacious bedrooms, each with its own walk-in closet, plus a full bathroom. An oversized walk-in attic provides abundant storage or the perfect opportunity to create a bonus room or extra living space. Dual zone HVAC provides comfort from a newer lower level unit and an upper unit replaced in 2026. Complete roof replacement was completed in 2026 as well. A voluntary HOA opens the door to the amenities of Safe Harbor Great Oak Landing Marina—private beach area, pool, 9-hole golf course, and more. Simply walk or hop in a golf cart to reach the marina and enjoy all the water-oriented lifestyle this community has to offer. You’re also minutes from Rock Hall, with its additional marinas, charter boats, shopping, and restaurants. Less than 10 minutes away lies Chestertown and Washington College, along with more shopping, dining options, a hospital, and a wonderful Saturday morning Farmers Market, and much more. Whether you’re seeking a full-time residence or a relaxing Eastern Shore getaway, this home delivers quality craftsmanship, flexible living spaces, and convenient access to the best of Great Oak Estates and the surrounding area.

22400 Great Oak Landing Rd., Chestertown

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

$359,997
4 Beds ⋅ 3 Baths
Welcome to 25133 Smithville Rd.! This spacious 4-bedroom, 3-bath traditional Colonial offers comfortable living with plenty of room to spread out. The main level features a desirable primary suite with a private full bath, along with an inviting eat-in kitchen and formal dining room perfect for everyday living and entertaining. Step outside to enjoy the spacious, level backyard with fencing for added privacy. There is plenty of room for entertaining, family gatherings, kids, pets, outdoor activities, and more—all while enjoying your own private outdoor space. With its spacious layout, convenient main-level primary suite, and private backyard, this home offers a wonderful opportunity to make it your own. Come see all that 25133 Smithville Rd. has to offer and make this home yours!

25133 Smithville Rd, Worton

Listing courtesy of Allfirst Realty, Inc.. Contact: 4433201344
$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:

$147,000
Build your dream home in Little Neck Farm! Lot #30 is a spacious residential property on Hagy Road with a deeded deep-water boat slip. The future home site offers beautiful pastoral views and is nicely edged with crape myrtles and evergreens. The deeded boat slip, located in the Little Neck community waterfront, is just a short stroll or drive away. The community docks were recently updated and replaced! The deeded boat slip #4 has lights, electric, and water. The waterfront also features space to store and launch a kayak, picnic tables, and a storage shed. Enjoy the peaceful open space and protected shorelines in Little Neck. Peaceful location, yet only 10 minutes to downtown Rock Hall, which offers two small grocery stores, ample shops, restaurants, and festivals throughout the year! This property is a prime location with water access, perfect for a full-time home or weekend getaway.

Lot 30 Hagy Rd, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

$1,495,000
3 Beds ⋅ 2 Baths
BIG BUCK FARM * GEESE * DUCKS & GAGGLE OF TURKEYS Hidden away at the end of country lane Privacy awaits Surrounded by woods with a unique mix of fields, water features to enjoy Natures Ever Changing Beauty. 106 Acres Hunting Farm in North East Kent County. Government regulation's insure surrounding farms will remain rather then 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. 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.

13235 Knotts, Golts

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$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:

$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:

$549,000
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:

$549,000
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:

$339,000
5 Beds ⋅ 3 Baths

6746 Quaker Neck Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$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: