Don't miss this rare opportunity. This special home offers spectacular and picturesque views of the Saint Michaels Harbor in addition to its prime location on one of Saint Michaels most desirable streets. Conveniently located near all of the in-town amenities and walkable to great restaurants, shops, brewery, winery, gallery, seasonal farmer's market, museums and more. This home has received a fresh interior painting, a deep cleaning and it is move in readyIt is a 4-bedroom, 3 full bath and 1/2 bath home with the 1/2 bath on the first floor. One of the bedrooms and a full bath is a guest apartment with a kitchenette located over the 2 car attached garage. The guest apartment is accessible from the inside of the home or by a private outside entrance. The Primary Suite includes an updated en-suite Bath with double vanity, walk-in shower and private toilet. The Primary bedroom has room for a king-size bed, a walk-in closet, a north harbor view and access to the 2nd floor front porch. The 2 additional bedrooms have large closets, harbor views and individual access doors to the front porch. Both bedrooms share a large, updated bathroom with a combination tub/shower. The main part of the home is both comfortable and casual while at the same time stately and refined. The kitchen and eat in breakfast /dining area looks out over the Harbor and opens to the 1st floor porch and porch swing which is a great place to have your morning coffee. The kitchen has a great layout, granite counter tops, stainless appliances, a Viking paneled refrigerator and a walk-in pantry. The Dining room or living room has a harbor view as well and a central fireplace with attractive marble and millwork. The architectural marvel of this home is the Conservatory. It is a fantastic room for entertaining with a double height ceiling and intriguing structure. This was in use as a great room / family room. The back wall could also accommodate a large bar and flat screen if desired. If interested, a future owner might consider it for a master suite. Two sets of French doors open to either the front lawn or side yard for entertaining. The unique design of the conservatory also provides a near 180-degree view of the harbor and all of the sunrises and sunsets.With the lowest price per square foot for a Luxury, Waterview, in town home, it is also a comparatively excellent value.

A Rare Waterview Masterpiece Designed for the Ultimate Boating Lifestyle. Set on 1.376 acres with breathtaking water views and unforgettable sunsets, this one-of-a-kind contemporary residence delivers luxury, functionality, and resort-style living at every turn. Thoughtfully designed with the boater in mind, this exceptional home offers expansive entertaining spaces, refined finishes, and outstanding access to boating amenities. The main level showcases a dramatic living room with gas fireplace and sweeping water views, a dining room opening to the rear deck, and a stunning gourmet kitchen featuring quartzite countertops, a grand center island, Wolf 5-burner gas stove, steam oven, convection oven, butler’s pantry, and an additional pantry/storage area with refrigerator. A screened-in porch just off the kitchen creates the perfect space for relaxed water view living. Also on this level are a hall bath, office or sitting room, main-level laundry, and a luxurious primary ensuite with small deck with stunning views, double vanities, jetted tub, and a separate shower and toilet area. The second level is ideal for hosting, offering three bedrooms with 2 full baths, plus two additional sleeping areas thoughtfully designed for guests. The fully finished lower level continues the luxury with a gym, room of choice office/bedroom with full bath, additional laundry hookup, spa-like bathroom with double vanities and an oversized shower, and a rear entry perfectly suited for coming in off the water. Outdoor living is nothing short of spectacular, featuring a professionally landscaped rear patio with water feature, firepit, garden irrigation, and automatic timers. A rear garage and workshop provide ample space for water toys, gear, and golf carts. Additional highlights include a deeded boat slip with two boat lifts, 90-amp electric vehicle charger, whole-house humidifier, three-zoned HVAC, Pella windows, architectural roof (2024), automatic water shutoff system (Flow Logic), and all appliances included. An exclusive opportunity to acquire the adjacent 1.245-acre parcel, offered separately, featuring a deeded boat slip and lift, with right of first refusal extended to the purchaser. This extraordinary property offers a rare blend of luxury, privacy, and elevated water view living. Truly one of a kind—schedule your private showing today.

Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners near Widehall and the Custom House. Completely restored in 2024–2025 by one of the town’s most iconic builders, the home blends historic character with modern comfort through thoughtful updates, new systems, and refined living spaces.Just one block to the waterfront or to morning coffee at Evergrain, the location captures the rhythm of Chestertown living—laid back yet polished, historic yet vibrant. This is more than a home; it is an irreplaceable asset and a true legacy property within one of Maryland’s most beloved waterfront towns.

This boater's paradise demonstrates the perfect blend of luxury and convenience. The property boasts three floors of sweeping waterfront views all easily accessed via your own private elevator. High end finishes can be found throughout and the home has been impeccably maintained. The first floor feels inviting with the fireplace, open kitchen, and guest bedroom with ensuite full bathroom currently being used as an office. The second floors wows you with 3 spacious bedrooms including the primary that has a walkout balcony for quiet evenings staring out over the water. The top floor provides yet another entertaining or living space with a wet bar, full bathroom, and a walk out balcony. Outdoor living in general is a highlight here with each floor allowing for a different perspective of the Eastern Shore landscape. Don't forget about the amenities of the community. Lounge out by the pool, walk to famous waterfront seafood establishments, or navigate the vast waters of the Chesapeake from your deeded 35 foot deep water boat slip just steps away. This luxury Eastern Shore destination is located just an hour from Washington, D.C. or Baltimore and less than two hours from Philadelphia.

Welcome to Windwood: where meticulous pride of ownership truly shows on this classic Cape Cod on nearly 10 acres of serene, private land. With an expansive 4-bedroom main house and separate guest cottage; this home is perfect for a multi-generational family who are looking for separate spaces or for a family looking to generate more income by utilizing the guest house as a rental. This home really epitomizes quality 1960's construction and craftsmanship: solid brick and cedar siding, southern pine hardwood floors throughout, elegant keyhole crown moldings, a wonderful dining room fireplace, built-in shelving cabinets, timeless dormers, and so much more. Coming up the circle drive you are received by a peaceful front porch; perfect for enjoying summer breezes and sunsets. Inside you are greeted to a welcoming foyer with a formal living room to your right and massive dining room to your left complemented by a wood-burning fireplace with intricate wood mantle. Moving back you will find the private main-floor primary suite with ensuite and large walk-in closet. The first floor further features a TV room and a recently renovated sun-room bump. out. Continuing on, the spacious kitchen with breakfast area was renovated in 2021 and now features honey-oak built-ins, custom cabinets, granite countertops, stainless steel appliances, propane or electric stove, a generously sized island with overhang seating, and LVP flooring. As you take the wide staircase upstairs you will find more gleaming hardwood floors that were just refinished. The second floor has three generously sized bedrooms; each with large closets and a smaller office space. Each end of the second floor features large attic storage areas. The full basement is partially finished with a spacious rec or workout room with a wood burning stove and new LVP floors. Across the brick breezeway, the guest house has also been recently renovated including all new kitchen appliances, walnut cabinets, washer/dryer, new floors, and upgraded bath. In front of the guest house is an attached two-car garage with additional areas for storage and tools. The backyard is a gardener’s dream and is fully fenced for the dogs and/or little kids. A small garden area, pergola and small fishpond complete the peaceful surroundings. Several walking trails have been cut out throughout the woods where you will find a large woodshed with plenty of storage. This wonderful property has so much to offer, you won’t want to miss it. Much more info and professional photos coming soon. Stay tuned!

Explore 92.71 acres of pristine Eastern Shore landscape, featuring a diverse mix of woods, marshland, and serene natural ponds that attract abundant waterfowl. The property provides outstanding habitat for sika deer and other native wildlife, making it ideal for hunters, outdoor enthusiasts, and conservation-minded buyers. Wooded, firm ground allows for convenient access throughout, while the location is just minutes from public boat ramps with direct access to the Chesapeake Bay. A rare chance to own a peaceful, wild retreat in Maryland’s scenic countryside.

Perfectly situated on over an acre, this custom-built masterpiece offers over 4,000 SF with three fully finished levels thoughtfully designed for luxurious living and effortless entertaining. From the moment you arrive, you'll appreciate the meticulous care, craftsmanship, and extensive upgrades this home has to offer. Step inside to find a spacious formal dining room framed by elegant segmental archways, setting a warm and inviting tone. The main level flows seamlessly into the heart of the home — the gourmet kitchen — featuring soft-close cabinetry, a large center island, dual ovens, under-cabinet lighting, an induction cooktop, a spacious walk-in pantry, and a reverse osmosis water filtration system connected to both the kitchen sink and refrigerator. Adjacent to the kitchen, a cozy breakfast nook provides the perfect space for everyday meals. The expansive family room offers the ideal gathering place, complete with a pellet stove, a beautiful wet bar perfect for entertaining, and oversized sliders that fill the space with natural light. These sliders open directly to the screened-in porch — newly updated with pet-resistant screens — and lead to an attached deck, creating even more space for outdoor relaxation. Upstairs, the second level is designed for ultimate comfort. The luxurious oversized primary suite features a private propane fireplace, dual walk-in closets, and a spa-like en-suite bathroom with a luxury stone jacuzzi tub, rainfall shower, abundant natural and overhead lighting, and separate his-and-hers vanities. Two additional bedrooms with spacious closets, a large bonus room with a pellet stove (ideal for a recreation room or optional sixth bedroom), and a second full bathroom complete this floor. For added convenience, a second-floor laundry room makes everyday living even easier. The third level offers two more versatile bedrooms, a full bathroom, and access to the HVAC system — perfect for home offices, guest suites, or teen retreats. The solar panels will be paid off before closing The outdoor space is just as impressive. Enjoy a partially fenced yard, ideal for children and pets to safely roam, an oversized attached 2-car garage with access to the crawl space, a detached 2-car garage that makes an excellent workshop, storage space, or man cave, plus an additional storage shed. A partial whole-house generator provides added peace of mind. And the best part? No HOA! Located just minutes from downtown Centreville's charming shops, restaurants, marina, and parks, with easy access to Route 301 and only 13 miles from the Bay Bridge, this property truly leaves no comfort feature overlooked. Welcome to a home where luxury, privacy, and convenience meet — your Eastern Shore dream awaits.

Rare lake front property in Kent County! Welcome to your serene getaway nestled on 2.62 acres of partially wooded land on Urieville Lake! This stunning 4-bedroom, 3.5-bathroom home offers the perfect blend of comfort and privacy, making it an ideal retreat for families and nature enthusiasts alike. With an option of a first floor bedroom there are currently three bedrooms on the second floor and one bedroom in the walk out basement, there’s plenty of space for family and guests. The open-concept living area is perfect for gatherings, featuring ample natural light and gorgeous views of the surrounding landscape & lake! Enjoy convenience and comfort with two full bathrooms on the second, one full bath on the lower level and an additional half bath on the first, designed with modern fixtures and finishes. The finished walk-out basement provides excellent additional living space, bath/bedroom & perfect for a game room, entertainment area, or a private office. It also offers direct access to the beautiful outdoors. The property spans 2.62 acres, providing ample room for outdoor activities, gardening, or simply unwinding in nature. The partially wooded area enhances your privacy while allowing for serene nature walks right in your backyard & along the Lakes edge! Located on Urieville Lake, enjoy fishing, boating, kayaking and other recreational activities just moments from your doorstep. This private setting is perfect for those looking to escape the hustle and bustle of city life. Urieville Lake is about 35 acres in size and is shaped like the letter Y. The average depth is about 3 feet and supports a standard bass/bluegill fishery and is managed accordingly. Anglers may also occasionally catch other species including pumpkinseed sunfish, brown bullhead catfish, golden shiners and common carp. Welcome home!

Nestled in the shadows of the Choptank River is a meticulously maintained home in the water-privileged neighborhood of Asbury. Expansive lot sizes give you the privacy needed within a walkable neighborhood. Sit in your rocker with a cocktail while enjoying the dream turned into a reality of a wrap-around porch. A large rear screened-in porch to watch the local wildlife opens onto extensive hardscaping, perfect for an outdoor fire pit to enjoy those cool evenings with family and friends. Large open kitchen into the family room is the heart of the home that features a wood stove. 4 substantial bedrooms upstairs. Main floor features an office that could be a wide range of things, including a main floor bedroom. Steps from the Asbury Nature Trail that brings you to your community dock and water access with Huge views of the Choptank River.

Welcome home to refined coastal living on Maryland’s Eastern Shore in this beautifully designed 3-bedroom, 3-bath home located in the premier 55+ community of Bay Bridge Cove in Stevensville, Maryland.This lovely and well-maintained home was built in 2022 and offers 2,074 square feet over two levels. The home blends light-filled spaces with effortless, low-maintenance living just minutes from the Chesapeake Bay.Soaring cathedral ceilings elevate the main living area, where a propane fireplace creates a warm focal point for entertaining or just relaxing. The kitchen is designed for gathering, featuring granite countertops, a custom backsplash, stainless steel appliances, and an expansive center island with cabinetry on both sides — ideal for casual breakfasts or evenings entertaining friends and neighbors. A dining area is located between the kitchen and living area, completing the truly open concept. Enjoy your morning coffee or curl up and read a good book in the sunroom located just off the living room, featuring lovely views of the tree lined open space at the rear of the home — no neighbors behind you! The main-level primary suite offers tray ceilings, dual closets, double vanities, and a beautifully tiled walk-in shower — a peaceful retreat at day’s end. A second bedroom and full bath on the main level provide convenience for guests, while the upper level offers a private third bedroom with full bath and a spacious family room with custom railing overlook, perfect for extended stays or additional living space.Other features of the home include a welcoming gated courtyard with charming bistro lighting, perfect for a little gardening, or unwinding at the end of the day. Beautiful custom blinds are tailored to each room, ceiling fans are located throughout, and the front and rear storm doors provide even more light into this light and airy home. The two-car garage has ample space for your vehicles, water toys, or just some extra storage. The lawn irrigation system helps to maintain a plush lawn, and lawn maintenance is included in the HOA, allowing you to enjoy the community lifestyle Bay Bridge Cove residents embrace.Bay Bridge Cove residents settle into a vibrant, resort-style setting with an oversized clubhouse with fitness center, meeting and gathering spaces, full kitchen, community pool, pickleball, and bocce. Activities abound at this gathering spot all year round! The walking/biking trails are throughout the community, as well as a dog park for your furry family members, and even a community garden for those fresh summer vegetables.Ideally located just minutes from the Chesapeake Bay, area golf courses, waterfront dining, shopping, and multiple marinas. Annapolis is a short 15 minutes away, Washington DC is about an hour, and Atlantic Coast beaches are approximately a 2-hour drive. This home offers the perfect balance of coastal charm, convenience, and active adult living, and is just waiting for you to call this HOME! Schedule your private tour today!

Motivated Sellers, bring all reasonable offers! Beautifully Restored 1890s Victorian in Trappe, MD - 6BR, 3.5BAStunning fully restored 1890s Victorian in the heart of Trappe. This spacious 6-bedroom, 3.5-bath home features a wraparound porch, formal living and dining rooms, a family room, and a marble primary bath. The home offers one gas fireplace for warmth and ambiance, plus four original decorative fireplaces that add timeless character throughout.The modern kitchen includes stainless steel appliances and a 36 gas range.Updated throughout with all-new plumbing and electrical, spray foam insulation, new windows, and a 4-zone heating system. Outdoors, enjoy a large slate patio and generous off-street parking. A rare blend of historic charm and modern efficiency -move-in-ready.Call Today for a Tour!

Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable waterfront community of Chester River Landing. Just a short walk or bike ride into downtown Chestertown, this elegant, turn-key home offers maintenance-free living, great amenities, and easy water access to the Chester River. The welcoming foyer seamlessly flows into the rear den or office which could be converted into a 3rd bedroom. Off the den is the first-floor bedroom and full bath. Enjoy the summer breeze from the private back screened-in porch; recently upgraded with high-tech flex screens and a ceiling waterproofing; keeping the porch dry. The real action is found upstairs. The living room – anchored by an electric fireplace with stone surround – is complemented by the oversized second story deck; perfect for grilling or watching picturesque Chester River sunsets. The modern kitchen features new stainless-steel appliances, abundant cabinet space, granite countertops and a large island with breakfast bar. Plenty of space for formal or casual dining. The second floor is finished by an oversized primary bedroom with ensuite bath and large walk-in closet. Should one desire an elevator; there are two locations where one could be built into the existing design. Leave your worries aside as the condo association takes care of all exterior maintenance, yardwork, and repairs. Boaters will enjoy the well-maintained community dock with slips available for purchase or lease (with board approval), or just drop in a kayak or paddle board; great on warm summer evenings. Other community amenities include the pool, walking paths, garden, picnic and grilling areas, and a fire pit. 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 walkways and parks. Chestertown is home to many festivals and an award-winning Farmer's Market every Saturday. New YMCA with full gym, racquet sports, lap pool, sauna, etc. Don’t miss your opportunity to enjoy worry-free living along the Chester River.

Welcome to the desirable Rivers End community, where lifestyle and location come together. Residents enjoy a community fishing pond, recreational area, and basketball courts, along with neighborhood events and the convenience of golf cart–friendly streets.This spacious home offers 5 bedrooms (septic approved for 4) and a layout designed for comfortable living and entertaining. The large living room flows openly into the kitchen, creating a bright and welcoming gathering space complete with propane hookup. The kitchen features tile backsplash, under-cabinet lighting, a built-in computer desk, and updated appliances including a 2025 dishwasher, 2024 refrigerator, and a stove and microwave from 2018.A separate dining room with vaulted ceilings adds charm and elegance, while hardwood interior doors and vaulted ceilings in the bedrooms with French door closets add character throughout the home. The oversized primary suite features a wide double door sized entrance, large walk-in closet, LVP flooring, jetted soaking tub, and separate stall shower, creating a relaxing private retreat.The second-floor bonus room has been converted into an additional bedroom and sitting/play area, and another bedroom includes its own attached half bath, offering flexibility for guests or other members.Additional highlights include a large laundry room that doubles as a pantry with built-in storage, new smoke detectors, and a crawl space with plastic vapor barrier. Major systems have been thoughtfully maintained, including a dual-zone Trane HVAC system ( 2020 air handler) and a hot water heater approximately five years old.The oversized garage offers extra room for storage or hobbies and is fully drywalled, with a generator outlet already in place. Outside, the private backyard features irrigation, providing a great space to relax or entertain. The shed with electric and gazebo convey as-is.Enjoy fishing or small boating in the community pond, or take advantage of the location just outside Seaford, close to local seafood restaurants with easy access to the beaches close enough for a day trip. This home offers the perfect blend of space, community amenities, and convenient coastal living.

Private backyard in Vibrant Community. Get lost in this backyard oasis close to downtown Easton in the very exciting neighborhood of Mulberry Station. Minutes from downtown Easton, you will get lost in all the special nooks and crannies hiding in your hidden paradise. Lose yourself in a book under the Crepe Myrtles, Zen out next to the manmade ponds with water features. Who needs a sound machine with the peaceful sounds of leaves rustling and babbling brooks babbling? A huge inground pool with a designated firepit area can make any evening special. This thoughtfully designed outdoor space needs to be seen to really be appreciated. Inside, you will find ample room to spread out. The lovely kitchen/family room combo features a gas fireplace to cozy up to. Indoor/Outdoor dining with sliders that open up from your kitchen onto your beautiful large deck with electric awning. Upstairs, Double doors open to your very large primary suite with walk-in closet and en-suite. Three other large bedrooms and bathroom round out the upstairs.

Spacious & Updated Home in Cloverfields on Kent IslandWelcome to this beautifully improved home located in the desirable Cloverfields community on Kent Island in Stevensville. Set on an oversized double lot with a private, tree-lined backyard with a brand-new privacy fence, this 3 bedroom, 2 bath home offers over 2,300 sq ft of total living space and a long list of recent upgrades.On the upper level, enjoy an open concept with laminate flooring throughout. An open kitchen with breakfast bar has all the appliances you need including dishwasher (one year old), stove (less than two years old) and a brand-new microwave. The dining room walks out to a screened in balcony to enjoy your morning coffee while catching the morning news or Today show. The living room features a large bay window allowing lots of natural light.The newly renovated primary suite features brand new luxury plank flooring, ceiling fan, walk-in closet and beautifully renovated primary bath with soaking tub, double sinks and walk in shower. A second bedroom and second full bath round out the upper level rooms.On the lower level you'll find a generously sized third bedroom, large family room with fireplace that walks out to the fenced in yard, laundry area and workshop with access out to the driveway area. Rough in plumbing appears to be in place for an additional bathroom but buyers are responsible for their own due diligence to add 3rd bath.Major improvements include a new HVAC system, privacy fencing, and ongoing exterior upgrades—new siding and roof installation are currently in progress.Cloverfields offers exceptional amenities: private beach on the Chester River, marina with boat ramp and rental slips, seasonal pool, playground, clubhouse, and low annual HOA fees. Conveniently located just minutes from the Chesapeake Bay Bridge, with easy access to Annapolis, Baltimore, and D.C.Owners are motivated—recently purchased in 2024 with plans to make this their dream home, a job transfer has prompted a quick sale. Don’t miss this opportunity to own in one of Kent Island’s most sought-after communities.

Remarkable remodel in the heart of Easton. Brand new everything from the studs out. Large open floorplan centered around the thoughtfully designed kitchen featuring a huge island, stainless steel appliances and close quiet cabinetry makes the heart of this home sing. Step outside to enjoy some after dinner cocktails on your beautiful brick patio with views of the Tred Avon River. Huge primary suite includes walk-in closet and en suite with walk-in shower. Central AC and Heat with mini splits in the back half help keep costs and temperature controlled. Seamlessly blending new and old charm, come see this whimsical home quickly

COMING SOON!!!!!Nestled in the heart of Maryland’s Lower Eastern Shore, 1151 Crocheron Road in Toddvilleoffers a rare opportunity to own a property surrounded by nature, privacy, and authenticEastern Shore charm.This home is perfectly positioned for those seeking peace, space, and outdoor living. Withabundant wildlife, open surroundings, and a quiet rural setting, the property is especiallyappealing to hunters and outdoor enthusiasts, with frequent sightings of deer and nativewildlife right on and around the property.Toddville is known for its rich watermen heritage, natural beauty, and unspoiledlandscapes—making it an ideal location for a primary residence, weekend retreat, orrecreational getaway. Whether you’re envisioning a hunting basecamp, a private escape, or aplace to enjoy the slower pace of coastal living, this property offers the flexibility to bring yourvision to life. 4 bedrooms, 2 full Bathrooms, newly remodeled kitchen, fenced yard and so many more wondeful features.Enjoy the freedom of country living while still being connected to nearby towns, waterways,and the unique lifestyle that makes the Eastern Shore so special.

A Rare Opportunity in the Heart of Historic ChestertownDiscover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage.Brimming with character and potential, the property currently features a townhouse on one side and two apartments on the other, offering a flexible layout ideal for renovation, income generation, or a creative reimagining. Whether you're envisioning a stately single-family residence, a dynamic live/work space, or a thoughtfully restored multi-unit investment, the possibilities are as expansive as the lot itself.That said, this is not a turnkey property. Significant settling has occurred over the years, and a substantial renovation will be required to bring it back to life. Offered strictly as-is, this is a true fixer-upper for the visionary buyer ready to take on a transformative project.Situated within both the Arts & Entertainment District and Enterprise Zone, this location supports both residential and business uses—making it an ideal candidate for those looking to merge lifestyle, business, and history. **See updated zoning info and description from town office in Documents.Bring your vision, creativity, and tools—and seize the chance to breathe new life into a piece of Chestertown’s storied past. Opportunities like this don’t come along often.Schedule your showing today and imagine the future you can build here.

A Rare Opportunity in the Heart of Historic ChestertownDiscover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage.Brimming with character and potential, the property currently features a townhouse on one side and two apartments on the other, offering a flexible layout ideal for renovation, income generation, or a creative reimagining. Whether you're envisioning a stately single-family residence, a dynamic live/work space, or a thoughtfully restored multi-unit investment, the possibilities are as expansive as the lot itself.That said, this is not a turnkey property. Significant settling has occurred over the years, and a substantial renovation will be required to bring it back to life. Offered strictly as-is, this is a true fixer-upper for the visionary buyer ready to take on a transformative project.Situated within both the Arts & Entertainment District and Enterprise Zone, this location supports both residential and business uses—making it an ideal candidate for those looking to merge lifestyle, business, and history.Bring your vision, creativity, and tools—and seize the chance to breathe new life into a piece of Chestertown’s storied past. Opportunities like this don’t come along often.Schedule your showing today and imagine the future you can build here.**See updated zoning info from the town in documents

Welcome home to this move-in ready home featuring 4 bedrooms and 3 full baths. The upper level features a large light-filled living room with windows on the front and side of the home. The living room opens into the combined kitchen and dining area. The kitchen features a new backsplash, stainless steel appliances, new faucet, and a kitchen island perfect for food prep, serving area, and plenty of additional cabinet storage underneath. The adjoining dining area provides ample space for your dining needs and offers convenient access to the nice-sized deck, perfect for outdoor dining and barbecuing. The deck has steps down to the rear yard for all of your outdoor activities. The partially fenced rear yard could easily be enclosed to provide safety and privacy. The remaining upper level features the upper level primary suite with full bathroom, and the other 2 bedrooms share a full hall bathroom. The lower level features the 4th bedroom with walk-in closet and adjoining full spa bathroom. This room can also function as a family room with full wet bar if you just need a little more relaxing space. This level is finished off with a laundry/utility room and garage entry. The location of the home is perfect for commuters and is less than 10 minutes to I-95 and a short trip to Delaware for work and tax free shopping, as well as all points south along the I-95 corridor to Washington, DC. Recreation abounds with a short trip to Elk Neck State Park, approximately 30 minutes away. The park features the Turkey Point Lighthouse which sits on a high bluff overlooking the Chesapeake Bay, Elk, and Northeast Rivers. The park offers campgrounds, rustic cabins, swimming, fishing, crabbing, miles of trails for hikers and bikers, as well as boat and canoe/kayak launches. This home is ready and waiting for you to come home! Schedule your tour today, don't wait! SHOWINGS BEGIN 11/2/25

Motivated Seller. Welcome to 121 Primrose Road, a well-built two-story home offering 2,034 square feet of living space on a .345-acre lot, located just outside downtown Chestertown in a quiet setting.The upper level includes three bedrooms and two full bathrooms, while the main level offers a convenient half bath. The first floor features a bright living area, a traditional dining space, and a spacious all-seasons room off the kitchen—ideal for everyday living or entertaining. The full basement provides excellent potential for future finishing, storage, or workspace.Recent improvements include newly installed LVP flooring in the downstairs bathroom and sunroom, completed this month. A brand-new septic system adds peace of mind, while the attached two-car garage and large rear deck enhance functionality and outdoor enjoyment.Situated on the Queen Anne’s County side of Chestertown, the property offers easy access to downtown shops, dining, and waterfront amenities, while still enjoying the feel of a peaceful neighborhood.

LET'S MAKE A DEAL!!! Come see this beautifully renovated ranch-style home offering over 1,431 sq. ft. of living space, ideally located on a quiet back street in a desirable water-oriented community with beach access.This 3-bedroom, 1 full bath home was completely renovated down to the studs in 2021, allowing the next owner to enjoy the benefits of extensive upgrades throughout. The open floor plan seamlessly connects the living room, dining area, and kitchen, creating a functional and inviting living space.The kitchen features white cabinetry, black granite countertops, and GE stainless steel appliances, while the home is enhanced by ¾-inch thick, 3-inch wide sanded and stained hardwood floors. A spacious family room offers a wood stove and slate flooring, providing additional living and entertaining space.Major improvements include all new plumbing and electrical systems (2021), Andersen Low-E windows, and a Pella sliding door with built-in blinds in the primary bedroom. The updated full bath features a tile surround, and the home is equipped with a high-efficiency Amana heat pump, 50-year architectural shingles, and updated siding.Additional highlights include a stackable washer and dryer, a large front deck, storage shed, and seasonal water views. Residents enjoy access to community amenities including boating, watersports, and beach access.A thoughtfully renovated, move-in-ready home offering comfort, quality, and lifestyle in a waterfront community.

Live with ease in this beautifully updated and maintained one floor home in downtown Chestertown. The current owners put a large addition on the house that includes a family room with wood burning stove, sunroom, and primary suite with en suite bathroom and walk in closet. A large laundry room on the main floor and updated kitchen with tons of counter space were other valuable design updates. The basement provides ample partially finished storage space in a completely dry environment due to serious structural improvements, sump pump and french drain system. Bring your hobby down there or your trusty work bench. The roof, HVAC, and hot water heater are all less than 10 years old. The front yard provides a polished experience with tasteful landscaping. The rear yard is quite large for a house in town and includes a raised bed garden and tidy shed. Experience the relaxed lifestyle of Chestertown with the Historic District's shops, Washington College, and the Margo Bailey park just a short walk away.

Easton charm meets everyday convenience at this coming soon opportunity at 207 Tred Avon Avenue. Ideally located just moments from downtown Easton’s shops, restaurants, galleries, andThis home offers the chance to enjoy in-town living with character and comfort.Upon arrival, a versatile den welcomes you into this charming bungalow - use it for an office, tv room, play area, or just a relaxing space to greet guests. Venture into the living room with built in shelving and decorative fireplace mantel.Off the living room, you'll find the primary bedroom with ample closet space and primary bath with a linen closet and access to the attic for additional storage space.Through the living room, you'll find a bright kitchen and dining room. The kitchen has lots of cabinets for storage, a built-in microwave with exhaust fan, and side door that goes right to the driveway for easy access to carry in your groceries. The laundry closet is right off the kitchen and large dining space. Two bedrooms and a second bath with an additional linen closet round out the interior features of the home.The backyard is a practically a blank slate to make your own. New fencing has recently been added and a small portion of the yard was already sectioned off for a pet area which could easily be converted into an elevated garden or entertaining space. A nice shed will convey with the property as well. There is ample space to add a patio for outdoor entertaining, carport, or even a garage (buyers to do their own due diligence for building regulations, permitting, etc.)The heat pump and air handler were recently renewed with a new compressor and new blower and a new roof was installed in 2024.Whether you're sipping coffee in the cozy den or headed into town for a night out, this home is the ideal spot to call your own.

Welcome to this spacious end-unit townhouse offering 4 bedrooms and 2.5 bathrooms, providing plenty of room for comfortable living. The main level features a bright and open layout with abundant natural light, ideal for everyday living and entertaining. The kitchen opens to the main living areas, creating a functional and inviting space.Upstairs, you’ll find generously sized bedrooms, including a primary suite with a private bathroom. Additional bedrooms offer flexibility for guests, a home office, or playroom. Enjoy the convenience of low-maintenance living while being just minutes from downtown Easton, shopping, dining, and parks. This home is a great opportunity for anyone looking for space, comfort, and a prime location on Maryland’s Eastern Shore.

Charming 3-Bedroom Rancher in an Ideal Easton Location!Nestled in a prime Easton location, 16 Willis Avenue offers the perfect combination of comfort, convenience, and charm. This well-maintained 3-bedroom, 1-bath rancher is situated on a desirable corner lot, just a stone's throw from the heart of Easton. Whether you're looking for a great starter home or a cozy space to downsize, this property has something for everyone.The thoughtfully designed layout includes a spacious living room with a large windows allowing for ample natural light with a separate dining room that leads into a well-equipped kitchen that includes a full-size washer and dryer. Hardwood floors can be found throughout the home. Three bedrooms and one bath complete the interior layout of this quaint in-town Easton home.From the kitchen, step outside to a screened-in porch, the perfect spot for enjoying your morning coffee, unwinding after a long day, or hosting friends and family for a gathering, all while staying cool and bug-free. Enjoy the privacy and spaciousness of a corner lot, offering ample outdoor space for gardening or simply relaxing in the fresh air.One of the highlights of this home is its proximity to downtown Easton, where you’ll find charming shops, dining, entertainment and year round events and festivals. Enjoy all the benefits of town living while still having the peace and quiet of a residential neighborhood.With neutral colors throughout and easy-to-care-for features, it’s perfect for anyone looking for a low-maintenance, move-in ready property.Whether you're starting out, downsizing, or looking for a peaceful retreat, this home offers great value in one of the most desirable locations on the Eastern Shore. Don't miss your opportunity to make this house your home!

Highly sought after large townhome in the desirable community of Mallard Landing in Denton, featuring almost double the square footage, and a rear deck off of the kitchen. Multi-generational living has a full bedroom and bath, as well as a large family room on the main floor. A few easy steps to the second floor brings you to a beautiful open kitchen, dining, and living room. The third floor features two more bedrooms sharing a full bath, as well as a large primary bedroom with en suite. New flooring throughout. Community pool and playgrounds make this home desirable for all ages. Easy highway access makes commuting a breeze, or in-home office space for working from home is also an option. Easy walking to the new brewery or local pub where friends and neighbors gather to break bread and share a pint. This homes location has it all.

Desirable end-unit, 3-story townhome located in the heart of Chestertown, just moments from downtown and adjacent to the new YMCA. This well-maintained home features newer carpet and paint, a one-year-old stove (purchased new for $4,000), and a hot water heater just two years old. A newer full-size stackable washer and dryer adds convenience.Enjoy both sunrise and sunset views with an east-facing front that fills the home with beautiful morning light and a west-facing rear offering stunning evening sunsets. The balcony has been recently stained, and the first-floor patio has been thoughtfully converted into a deck with built-in wood flower boxes—perfect for outdoor enjoyment.The versatile first level offers flexible space ideal for a bedroom, office, or exercise room, complete with a gas fireplace and sliding door access to the deck. The garage includes a built-in loft, workbench, and shelving for added storage and functionality.Upstairs, the primary suite features a vaulted ceiling and a spacious en-suite bath with soaking tub and walk-in shower. A mature maple tree enhances the backyard setting, providing charm and seasonal beauty.Move-in ready and ideally located—this home offers comfort, updates, and convenience all in one.

Welcome to life in Rock Hall — a charming waterfront town where the pace is slower, the people are friendlier, and the Chesapeake Bay lifestyle is part of everyday living.This lovingly renovated home was thoughtfully updated by owners who cared about the details—not a quick flip—resulting in a property full of character and quality improvements throughout. Inside, you’ll find beautiful LVP flooring, a bright open-concept layout, and a stunning kitchen featuring granite countertops, a tile backsplash, stainless steel appliances, and plenty of space to gather after a day on the water, experiencing Chestertown and all the other towns nearby!For peace of mind, all major systems are new, including a brand-new roof, and a home inspection has already been completed with items addressed, making this home truly move-in ready.The layout offers comfort and privacy with the primary suite tucked away on one side of the home, while the three additional bedrooms are located on the opposite side, perfect for maybe or a home office setup. The home is connected to public water and sewer, and also offers fiber internet, giving you modern convenience in a laid-back coastal setting.Step outside and enjoy the freedom that comes with no restrictions—bring your boat, RV, or water toys, and if you’ve been dreaming of building a pole barn or workshop, you can do that here too.Located just minutes from creeks, rivers, and the Chesapeake Bay, this home places you right in the heart of one of the Eastern Shore’s most beloved boating towns. Rock Hall may only have one traffic light, but it’s full of life—with marinas, waterfront restaurants, coffee shops, boutiques, ice cream stops, and a quaint downtown. The town hosts events throughout the year, creating that true small-town vibe where everyone knows your name—or soon will.If you’ve been searching for a fun, beachy lifestyle with small-town charm, modern updates, and room for your boats and hobbies, this home delivers.Rock Hall — where nice people live.

Seller has to find home of choice. Welcome home to this charming 2-bedroom, 1-bath gem nestled in a quiet, established neighborhood. Perfect for first-time buyers, downsizers, or anyone looking for comfortable, low-maintenance living, this home offers both warmth and functionality.Step inside to find beautiful new wood flooring flowing through the living room, kitchen, and hallway, creating a fresh and modern feel throughout the main living areas. The spacious living room is ideal for relaxing or entertaining guests, while the kitchen offers plenty of room to cook and gather.The oversized primary bedroom is a true retreat, featuring a generous walk-in closet with ample storage space. A well-appointed second bedroom provides flexibility for guests, a home office, or additional family members.Situated on a .4-acre lot, the fully fenced backyard offers privacy and room to enjoy the outdoors. Spend summer days cooling off in the above-ground pool, hosting barbecues, or simply unwinding in your own private space.With its inviting layout, recent updates, and convenient location, this home is ready for you to move in and make it your own.

Looking for a 3 bed farmhouse in Millington with classic charm and modern updates? This warm and friendly 1920 single family home offers 1508 square feet on a 0.17 acre lot with a 2021 roof, vinyl siding, three second floor bedrooms, one full bath, and a half bath off the kitchen. A wrapped front and side porch sets the tone, while a rear wooden deck opens to the yard for easy outdoor living. The heated rear garage includes driveway parking and a setup that allows welder hookup, ideal for hobby work or small trades. Inside, the layout provides a cozy front living space, practical kitchen flow, and natural light throughout. Located in Millington with quick access to Route 301.

Enjoy coastal living this fall and beyond with this meticulously maintained, fully furnished, turn-key 1-bedroom, 1-bath condo in Ocean City, MD. Perfectly situated on the first floor, you’ll appreciate the ease of access—no stairs to climb when bringing in luggage or supplies. Inside, the open-concept kitchen and living area provide a bright, welcoming space to relax or entertain. Step outside to your spacious balcony, complete with comfortable furniture, hurricane shutters, and a convenient storage shed for beach gear and toys. Recent upgrades include a new washer/dryer (2023), refrigerator (2019), and a Google Nest thermostat that allows you to control the climate remotely. After a day at the beach, rinse off in the community’s outdoor shower before heading inside. Parking is included for added convenience.Just two short blocks from the ocean and within walking distance to the historic Ocean City Boardwalk, Jolly Roger Amusement & Splash Mountain Water Park, plus countless restaurants and shops—this location offers the best of everything. The Jamaica Daybreak Condo Association recently completed extensive exterior renovations (May 2025), with all assessment fees already paid in full by the seller—giving buyers peace of mind. With some of the lowest condo fees in the area at just $325/month, you’ll also enjoy discounted cable TV and internet. Lovingly owned for 20 years and never rented, this condo is move-in ready and waiting for its next chapter.

Welcome to this sweet ranch-style home in Worton, Maryland, tucked into a quiet little neighborhood of Knight’s Landing surrounded by beautiful farmland. It’s the perfect spot if you’re looking for peaceful living without feeling far from everything—just under five minutes to the local high school, community center, and park. Cozy, convenient, and easy on the budget, this home offers small-town vibes with everyday essentials close by.Property sold AS- IS Seller will make NO REPAIRS

LOT for sale!!! An exceptional opportunity to enhance a premier waterfront lifestyle. This 1.245-acre water-view homesite in Sunset Pointe includes a deeded boat slip and lift

PRICE REDUCTION!!Wonderful lot in Betterton, only 2 blocks from the beach, and your chance to make wonderful memories in this community known as the Jewel of the Chesapeake. Betterton sits right on the upper Chesapeake Bay at the mouth of the Sassafras River, an extremely popular boating area. The beach is beautiful with calm waters and amenities for a perfect day at the beach. This community is certainly a treasure and one of the areas best kept secrets! Don't miss out on your chance to build your dream home in one of the best little spots in Maryland! Water/Sewer Allocation is available through the town.

(Lot 2 - .685 acres & Lot 3 - .689 acres) Conveniently located slightly off 291, in a private area on a dead-end road, this property is close to Chestertown and minutes away from route 301. Lots sit high off the road level and adorned with young saplings. Soil evaluation from 2011 approved for 3 beds and a 2,000 sq ft home, located just outside the critical area. Lots being sold together!

Come build your dream home. Located right off E Sharp Street on Chesapeake Villa is your .46 acre lot. Location is perfect to everything Rock Hall has to offer, from shops to restaurants to the water. Come check it out today.Lot has water/sewer hookup available, contact town of rock hall to confirm fees.

Discover this cozy 2-bedroom, 1-bathroom mobile home, perfect for comfortable living. Featuring a large screened-in porch, you can enjoy fresh air year-round without the hassle of bugs! Conveniently located near restaurants, shops, and essential services, this home offers both comfort and convenience. Don't miss out on this affordable and well-located gem!

One parcel comprised of 2 cleared lots in Tolchester Estates. The community is on the Chesapeake Bay and the residents have access to the beach and there is a marina close by.County states water/sewer allocation is available. Buyer to confirm with due diligence.

Great opportunity to own a lot in Chesapeake Landing! Currently does not have a valid perc. Water access to Worton Creek if you join the voluntary civic association! Close to Worton Marina and Chestertown.

Welcome home to this spacious 5-bedroom, 2-bath Colonial located in the heart of Ridgely. This in-town property offers a large kitchen with plenty of space for cooking and entertaining, a comfortable living room, and generously sized bedrooms throughout. The traditional floor plan provides a warm and inviting flow, perfect for both daily living and hosting guests. Enjoy the convenience of being close to local shops, parks, and restaurants while still having the comfort and character of small-town living.

Welcome to 509 Cannon Street! This cozy 2-bedroom, 1-bath home has been thoughtfully updated and is ready for you to move right in. Inside, you'll find a comfortable layout and a brand-new HVAC system to keep you comfortable year-round, plus the convenience of off-street parking.Tenants are responsible for electric, town water and sewer, and internet services. To qualify, applicants must have a credit score of 600 or higher with no delinquent accounts and a monthly income of approximately three times the rent. All household members over the age of 18 are required to complete an application.This well-maintained home won’t last long—reach out today to schedule your showing and make 509 Cannon Street your next home.