With almost every inch updated since 2012 - from the roof to the floors - this adorable two bedroom, two and half bath cottage is turnkey. The luxury primary suite, added in 2014 by a sought-after custom contractor, has tall ceilings, a cozy bay window seat, walk-in closet, en-suite bath with heated tile flooring, and spa shower. The cozy family room with wood-burning fireplace opens to the awning covered back patio to extend the living space into the mature English gardens. Just a few short blocks from the waterfront and the farmer's market, amble or ride bikes (or register your golf cart!) to take advantage of all that Downtown Chestertown offers. Ready for showings on Thursday September 25^th!

Endless Possibilities on 20 Rolling Acres at Dawnwood Farm in Still Pond, Maryland

Discover the magic of Maryland’s Eastern Shore at this captivating 20-acre farmstead, where heritage charm meets modern comfort. Whether you're a dreamer, a doer, or a little of both, this property offers something extraordinary for every kind of buyer—from adventure-seeking families and aspiring homesteaders to seasoned growers and urban escapees in search of space to breathe.

At the heart of the property stands a gracious three-story 19th-century Victorian farmhouse, beautifully preserved and thoughtfully updated over the past decade. Original character—like hardwood floors, tall ceilings, and elegant millwork—blends seamlessly with modern conveniences, including upgraded systems, renovated kitchens and baths, and flexible living spaces suited to today’s lifestyle.

Outdoors, you’ll find yourself surrounded by gently rolling country hills, inviting everything from morning hikes and afternoon picnics to stargazing by a campfire at night. Cool off with a dip in the in-ground pool, then retreat to the pool house for relaxation or weekend entertaining. A charming caretaker’s cottage provides extra space for guests, rental income, or multi-generational living.

For those called to the land, the established organic gardens and mature fruit trees—peach, fig, and pawpaw—make it easy to envision a self-sustaining lifestyle. Cultivate your own food, raise chickens, or expand into a full-scale working farm—there’s room to grow, and inspiration at every turn. Perfectly suited for horses or livestock - the property includes two large restorable open bay barns that have been structurally stabilized, and a vintage silo. Approximately 15 acres of organically farmed open fields are currently under the purview of the Washington College CES’s Natural Lands Projectand planted with native wildflowers which are in full bloom all summer long.

And when you're ready for a change of pace, Betterton Beach and the sparkling Chesapeake Bay are just a few miles down the road, offering kayaking, crabbing, sunset walks, and family beach days that feel like a vacation—without ever leaving home.

Whether you're seeking a weekend getaway, a family compound, or a forever home with purpose and possibility, this Still Pond treasure offers the rare blend of privacy, charm, and usable land—just minutes from Chestertown and an easy escape from city life.

Don’t miss this opportunity to live your next chapter—schedule your private tour today and experience the beauty, space, and freedom of life on the Eastern Shore.

Spacious, Stylish, and Designed for Real Life – Welcome to Orchard Hill

Discover the perfect blend of comfort, flexibility, and convenience in this expansive 4-bedroom home, tucked into the sought-after Orchard Hill neighborhood of Chestertown, MD. With thoughtful upgrades and versatile spaces, this residence is ideal for those looking to level up their lifestyle—whether you're a young professional seeking work-from-home ease, those looking for room to spread out and make a place their own, or hosting large holiday gatherings under one roof.

Enjoy the ease of main level living, including a beautiful 2024 renovation of the custom primary bath that brings spa-level luxury to your daily routine. The chef in the house will be inspired by the gourmet kitchen, outfitted with top-tier appliances perfect for entertaining or everyday culinary adventures.

Need a quiet space to work or study? A dedicated home office offers privacy and separation. Upstairs, a second-floor great room provides an ideal zone for movie nights, play space, or a creative studio — the possibilities are endless.

Outside, the large yard invites your vision—garden, playset, patio, or all of the above. With plenty of room to grow, this outdoor space is a blank canvas for your next chapter.

Located just minutes from downtown Chestertown, the Chester River, and everyday essentials like grocery stores and shops, this home offers the perfect balance of neighborhood peace and easy access to town life.

Ready for more space and more possibilities? Schedule your tour today and come see how life fits in Orchard Hill.

Welcome to your Eastern Shore escape—where timeless charm meets modern convenience on over four beautifully private acres in the heart of Quaker Neck. Just a short drive from historic Chestertown, this double-lot property invites you to embrace a slower pace, with all the major updates already completed: new septic, HVAC, and roof in 2021, plus thoughtful improvements through 2025 including a designer kitchen appliance package, new windows and doors, a stunning new upstairs hall bath, upgraded electric, water treatment system, gutter guards, crawl space encapsulation, and lightning-fast fiber optic internet.

Inside, the home unfolds with warmth and versatility. A vaulted-ceiling dining room sets the stage for intimate dinners or festive holiday gatherings. The four-season sunroom, just off the living room, brings the outdoors in with peaceful views and year-round natural light. Cozy up in the den by the wood-burning fireplace, or gather in the spacious family room around the pellet stove—both perfect for relaxing evenings and snowy days.

With four comfortable bedrooms, there's space for everyone, including a private primary suite that offers a true retreat with its luxury en suite bath. Whether you're hosting summer crab feasts or crisp autumn poolside evenings, the heated in-ground pool is ready to anchor your best memories. The detached workshop is ideal for storage or hobbies, and the pool house keeps all the essentials tidy and accessible. Even your four-legged family members have a space of their own in the fully outfitted kennel—ready for pets or easily repurposed as a charming chicken cottage.

Surrounded by trees with farmland views in every direction, this hidden gem offers serenity and space without sacrificing proximity. For those seeking a home where lifestyle, comfort, and convenience converge—this one is ready to welcome you home.

Cute as a button in Chester Harbor! Just the right amount of space... a third of an acre yard, three bedrooms and a bath. New in the past few years: flooring throughout, metal standing seam roof, generously sized HVAC, and asphalt driveway sealant. Large two bay shed for storage and lawn tools has electric, and the back deck is ideal for grilling and picking crabs. Low maintenance and move-in ready!

A truly unique and versatile property – perfect for all generations! Bring everyone along to experience this stunning property, offering an incredible combination of space, style, and functionality. The 3-bedroom, 2-bath main home has been thoughtfully designed to cater to both relaxation and entertainment, featuring expansive living areas and high-end finishes throughout.  The spacious primary suite is a true retreat at the end of the main hall, thoughtfully designed with comfort and functionality in mind. Flowing seamlessly off the bedroom is a bright, open-concept bathroom, flooded with natural light. At its center, a sleek glass-enclosed, tiled shower which offers a spa-like experience, framed by clean lines and premium finishes. An elegant dual vanity stretches across one wall with modern fixtures, and ample under-sink storage, perfect for effortless morning routines. Built-in cabinets provide generous storage space for linens and essentials, blending style with practicality. Attached to the main bath area, a discreet door leads into a fully attached laundry & linen room, offering ultimate convenience with a stacked washer and dryer and additional cabinetry — all tucked neatly within the primary suite for maximum ease and privacy.

The centerpiece of this home is the incredible family room, an open space that provides a perfect flow for gathering, entertaining, or simply unwinding. The gourmet chef’s kitchen is a true showstopper, equipped with state-of-the-art appliances, ample counter space, custom cabinetry, and a large center island that’s perfect for meal prep or casual dining. Whether you're hosting a dinner party or cooking for your family, this kitchen will surely inspire your inner chef. Off the main living areas, the home office with a separate entrance offers a quiet, professional space ideal for working from home or managing personal projects without interrupting family life. The full basement is a highlight, featuring a cozy gas fireplace and a kitchenette for additional living or entertaining space. This expansive lower level offers endless possibilities – create your dream media room or play area.

Attached to the main home, the in-law suite offers a fully independent living space, with 2+ bedrooms, a full bath with laundry, an eat-in kitchenette, and a gas fireplace for added warmth and coziness. A charming back porch extends the living space, providing a private outdoor retreat. Whether you have extended family or guests, this suite offers the perfect balance of comfort and privacy. Enjoy the serene outdoor setting with a large wrap-around deck, perfect for relaxing or entertaining while soaking in the views of the expansive, private backyard.

Thoughtful landscaping surrounds the property, creating a tranquil oasis for family and friends. The mature gardens are in full bloom from Spring through Summer and offer a feast for the senses, full of color and sweet smells that waft through open windows. This property boasts two driveways - one equipped with an EV charger next to the parking pad - providing ample parking and easy access to the main home, the home office, and the in-law suite. Large, accessible storage sheds ensure there’s plenty of room for everything you need, from seasonal items to tools and equipment. For the little ones, a finished playhouse provides a magical space for imagination and fun, while still being a part of the beautiful surroundings.

This sprawling estate offers the ideal setting for multigenerational living, with separate yet interconnected spaces that provide both independence and togetherness. Whether you’re hosting family gatherings, running a business from home, or simply enjoying the serenity of the setting, this property truly has it all. A rare opportunity to enjoy both privacy and accessibility on a breathtaking 4.5-acre parcel. Just miles from the Georgetown Harbor on the Sassafras River, enjoy local hot spots such as the Fish Whistle at the Granary, The Kitty Knight House, and Twinny's with a Twist for a sweet treat.

The Shore is calling, bring a crowd or just escape for yourself... there is space to bring everyone or just enjoy the peace and quiet of this truly lovely setting.

Welcome to your slice of the Chesapeake Bay lifestyle! Nestled in the quaint, walkable town of Rock Hall—just steps from marinas, waterfront, dining, and shops—this 3-bedroom, 2-bath coastal cottage offers the perfect blend of charm, comfort, and flexibility. Whether you're searching for a weekend retreat, a year-round residence, or a smart investment property, this one checks all the boxes.

Step inside and feel instantly at ease. This well-maintained home features light-filled living spaces, an easy-flow layout, and thoughtful updates throughout. The updated kitchen has newer stainless appliances, the dining area and reading nook are ideal for gatherings and lively games, while the main level bedroom offers a quiet place to recharge after a day on the water. The two large bedrooms upstairs have room for plenty, and the full bath has a soaking tub to unwind.

Outside, enjoy laid-back afternoons on the expansive back deck—perfect for grilling, crab picking, or simply taking in a Bay breeze. The partially fenced rear yard offers privacy and room for the pups, and to play or garden, enhanced by low-maintenance landscaping that lets you focus on fun, not work. The shed is four years new and offers storage for water toys, yard games, and boating necessities.

But here’s the best part: a separate 2-bed, 1-bath income unit gives you the opportunity to generate revenue while you relax. Ideal for short-term vacation rentals, hosting guests, or even a home office or studio.

Live where others vacation. Walk or bike to the harbor, charter a sunset sail, jump on your boat that is nearby at a marina, or paddle out from a nearby launch. Rock Hall is known for its friendly community, laid-back vibe, and stunning sunsets—and this home puts you right in the heart of it all.

Don't miss this rare opportunity to own a turn-key home with coastal character and rental income potential in one of the Maryland Eastern Shore’s most beloved waterfront towns. [Some furnishings and décor available, too! To be discussed outside of the contract of sale.]

Discover the perfect blend of vintage charm and modern updates with this beautifully maintained 1950s craftsman, peacefully tucked along the scenic Chester River. Whether you're searching for a quiet second home getaway or a prime income-producing investment, this property offers the waterfront lifestyle so many dream about—boating, fishing, and relaxing right from your own private dock.

The heart of the home is a tastefully updated kitchen, designed for both everyday living and easy entertaining. A main-level bedroom and full bath provide comfort and convenience, while upstairs, you'll find two additional spacious bedrooms and a vintage full bath—ideal for hosting family and friends. Wall to wall windows flood the sunroom with natural light, where you’ll enjoy stunning river views all year round—perfect for morning coffee or evening unwinding.

Outside, a large yard provides endless possibilities for outdoor living, from garden parties to quiet afternoons with a fishing pole. The private dock means your boat is always just steps away, ready for sunset cruises or a spontaneous day on the water. A full walk-out basement offers easy-access storage for all your water toys, fishing gear, boating essentials, and garden tools, making waterfront living truly effortless.

Set on a double lot - totaling almost an acre and a half - in a serene, private locale nestled between the historic charm of Chestertown and Rock Hall, this property offers the best of both worlds: peace and quiet without being far from dining, shops, and cultural events.

This stunning Victorian home has been treated to an incredible renovation, rebuilt from the studs, but preserving the original details and charm! The hardwood floors absolutely gleam. This four bedroom, three full bath home spans almost 2800 square feet. With a custom kitchen overlooking the backyard and in-ground pool, a large laundry/mud room, an additional space for a den or home office (offering a separate entrance, too), plus the original dining and living room, which has 9'+ ceilings. The second floor features four bedrooms, all with dedicated mini-split HVAC units, a hall bath, and a spacious primary suite complete with a massive closet, en suite bath with dual vanity and tiled shower, and a coffered ceiling. A few additional features include off-street parking, a fully fenced backyard, and a sweet front porch perfect for your morning cup of coffee.

Experience the waterfront lifestyle like never before in this stunning mid-century modern home, which seamlessly hangs cliffside over the serene waters of the Chesapeake Bay's Fairlee Creek. Offering unparalleled privacy and exclusivity, this extraordinary residence evokes the sensation of floating on a boat, where every moment feels like an escape to a tranquil paradise. The unique design and architecture of this home harmoniously blend with the natural landscape, offering expansive views of the surrounding water and wildlife from nearly every room.

Set on a generous almost 2-acre parcel, the property includes not only the main residence but also a second residence, making it the perfect retreat for families or guests. Together, the two homes boast five spacious bedrooms, providing ample room for relaxation and privacy. Whether you’re hosting family gatherings or enjoying peaceful solitude, the expansive living areas, large windows, and open floor plans invite you to savor the beauty of the bay from within the comfort of your home.

Step outside, and you’ll find a private beach perfect for sunbathing, swimming, or launching kayaks and paddleboards into the calm waters of Fairlee Creek. The home also includes its own private dock, offering easy access for boating enthusiasts to explore the Bay’s stunning waterways. For those seeking a sense of community, this property provides access to the neighboring Safe Harbor Great Oak Landing, where residents can enjoy a wealth of amenities, including a marina, pool, golf course, dining at waterfront restaurants, and a lively beach bar—ideal for casual gatherings or sunset cocktails.

This home is not just a property; it's a lifestyle—a rare and exclusive opportunity to immerse yourself in the beauty and serenity of waterfront living, with all the modern conveniences and luxury amenities you could desire. Whether you’re looking for a full-time residence or a vacation getaway, this mid-century modern home offers the perfect blend of style, comfort, and natural beauty.

Nestled on the edge of the desirable Crestview neighborhood, this main level living home boasts beautiful hardwood floors, an easy flow perfect for entertaining, an ample screened in porch with views of the wooded back yard, and a walk-out, unfinished basement perfect for a gardening room or enclosed storage. Roof is only a few years young!