Gobbler Hill, circa 1858 with an addition built in 1989, sits like a jewel atop one of the highest points in Kent County. Listed on the National Historic Registry, the transitional architecture is an excellent example of late Greek Revival to early Italianate. The property consists of four parcels totaling over 65 acres. Wildlife abounds on the fields of native prairie grasses, wild flowers, woods, approximately 20 tilled acres and a large pond. Impeccable attention was payed to maintaining the historic character of both the interior and exterior. From the Lincrusta wall covering, 19th century faux wood finishing, plaster medallions, white and sugar pine wood floors and crown molding on the 11 ft. ceilings to the monumental copper roof, the thoughtful restoration is stunning. The newer addition beautifully blends into the original section adding modern conveniences and natural light. The library boasts black walnut bookshelves constructed by a local craftsman. Well maintained grounds offer gardens, mature trees, a classic poured concrete in ground pool with inlaid tile and stunning views. This unique, lovingly restored piece of Kent County history is now looking for a new steward to guide it into its next chapter.

Gobbler Hill, circa 1858 with an addition built in 1989, sits like a jewel atop one of the highest points in Kent County. Listed on the National Historic Registry, the transitional architecture is an excellent example of late Greek Revival to early Italianate. The property consists of four parcels totaling over 65 acres. Wildlife abounds on the fields of native prairie grasses, wild flowers, woods, approximately 20 tilled acres and a large pond. Impeccable attention was payed to maintaining the historic character of both the interior and exterior. From the Lincrusta wall covering, 19th century faux wood finishing, plaster medallions, white and sugar pine wood floors and crown molding on the 11 ft. ceilings to the monumental copper roof, the thoughtful restoration is stunning. The newer addition beautifully blends into the original section adding modern conveniences and natural light. The library boasts black walnut bookshelves constructed by a local craftsman. Well maintained grounds offer gardens, mature trees, a classic poured concrete in ground pool with inlaid tile and stunning views. This unique, lovingly restored piece of Kent County history is now looking for a new steward to guide it into its next chapter.

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.

This masterpiece is finally complete. Rebuilt in 1863, the Tilley Residence showcases classic Second Empire style on one of Chestertown’s most prominent corners, neighboring Widehall and the Custom House.Expertly restored in 2024–2025 by one of Kent County’s premier builders, the home offers new HVAC, electrical, plumbing, roofing, flooring, and a refreshed open layout. Custom kitchen and baths balance modern comfort with timeless character. A grand three-story staircase and arched entryways welcome you inside. The front porch overlooks town and offers water views. The primary suite includes a fireplace, walk-in closet, and a tiled shower room with views from two sides. The Mansard roof provides a full third floor, and the basement includes a great wine cellar opportunity plus ample storage. A fenced rear yard, off-street parking, and a detached garage complete this rare offering—historic charm blended with modern amenities.

The Sally Harris Mill House was once part of the Bloomingdale Estate is one of the remaining 18th Century masterpieces on the Eastern Shore. This peaceful farmette boasts over 31 acres with a blend of open pasture and wooded seclusion. The property sits on the Western banks of Madam Alices Branch, a tributary of the Wye River. Mature evergreens line the entrance creating a dramatic feel and historic charm is displayed throughout the home with 5 fireplaces, Flemish bond brickwork, and a gambrel roof. Modern amenities have been incorporated with the 2 story North wing which was completed around 2000 to include a first floor primary suite with en suite bathroom, makeup room, and 2 separate walk-in closets on the first floor and 2nd floor family room. The updated kitchen, partially finished basement with kitchenette, and heated pool are also highlighted upgrades. Outdoor living is celebrated here with a screened in rear porch for dinners in nature, a front porch to sit and watch the wildlife, and pool deck for making memories. Bring your machines and toys because there is plenty of storage in the outbuildings. The 2 story machine shop has been impeccably maintained and is perfect for any type of project. The open pasture would be perfect for horses and though they haven't been maintained in a few years, the forest contains nature trails for disconnecting from the hustle and bustle or hunting opportunities. This is your chance to make a piece of Eastern Shore's history your own peaceful retreat.

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.

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.

Stunning waterfront property with private dock site on the Chester River. The house has been gutted and needs a complete rehab, or it can be removed and rebuilt to suit your dreams. Building plans are available. The property features a brand-new BAT septic system that has yet to be connected. Beautiful location and views! Just a short drive to Chestertown. 3 ft mean low water, buyer to verify.

Prepare to be wowed when you walk through the front door. Gleaming hardwood floors, huge floor-to-ceiling windows, high-end kitchen and primary bath. Floor plan that flows beautifully. 4 bedrooms and 2 baths. Wood burning fire place in the living room. House is filled with natural light. Two car garage under the house with unfinished basement. Windows, roof, appliances, and HVAC have all been replaced. Electric has been updated. The list of improvements goes on. Come see this for yourself. It's gorgeous!

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.

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

Experience the best of in-town Chestertown living in this custom-built single-level home! The open floor plan features abundant natural light, gleaming hardwood floors and a bright, inviting layout perfect for entertaining or relaxing. The dining room is open to the kitchen which includes some updated appliances, ample cabinet storage, and a breakfast bar. The primary suite has a large walk-in closet and an en-suite bath which now boasts a soaking tub. Step outside to enjoy the large deck, fire pit patio, and fully fenced backyard. This home offers comfort and convenience at every turn. Just a few blocks from Washington College and a short stroll to Downtown Chestertown’s charming restaurants, shops, and waterfront.

Fully furnished! Adorable rancher in a PRIME location in Rock Hall. Just steps to the marinas, restaurants, and shops. The house has been completely remodeled. All new appliances. Large family room with a pellet stove and plenty of space for social gatherings. Nice-sized bedrooms and 2 full bathrooms. Luxury vinyl plank flooring throughout. Detached garage and potting shed. Less than 1/2 mile to the public beach. Private backyard with koi pond and water feature. The current owners have their boat docked at a nearby slip, and they can see it from the property. There is no work to be done here. Just bring a suitcase and move right in!

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

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.

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.

This meticulously maintained end-unit townhouse offers the best of both comfort and convenience. Overlooking a scenic walking trail, this home is just a short stroll to Easton’s vibrant downtown, with dining, shopping, and all town amenities right at your doorstep. Inside, you’ll find gleaming hardwood floors throughout the main level, creating a warm and inviting atmosphere. The spacious living and dining areas flow seamlessly into a gourmet kitchen, complete with a double wall oven, gas cooktop, pantry, and elegant granite countertops. French doors lead to a outdoor balcony, perfect for relaxing or entertaining.The main suite is a true retreat, featuring a vaulted ceiling, loft area, a generous walk-in closet, and an en suite bath. The second bedroom also has its own walk-in closet and full bath creating a second main bedroom. Please note: this unit offers the same square footage as the 3-bedroom models, but the seller thoughtfully combined the two smaller bedrooms to create a spacious second primary bedroom instead. The lower level offers a cozy family room, laundry area, and a convenient half bath. Access to the 2-car garage is also located on this level. New roof and carpet installed 2025. Experience the charm of downtown living with the added benefit of modern comforts.

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 Sellers!!! Welcome to 121 Primrose Road, a spacious two-story residence offering 2,034 square feet on a .345-acre lot. This well-built home delivers comfort, functionality, and potential in a peaceful setting just outside downtown Chestertown.Inside, you’ll find three bedrooms and two full baths upstairs plus a convenient half bath on the main level. The main floor features a bright living area, a classic dining space, and a large all-seasons room off the kitchen—perfect for gatherings or relaxing year-round. The full basement offers a blank slate, ready to finish as a recreation room, workshop, or extra storage.A brand-new septic system provides peace of mind, while the attached two-car garage and expansive back deck add everyday convenience. Situated on the Queen Anne’s County side of Chestertown, this property keeps you close to the shops, restaurants, and waterfront charm of downtown while offering the privacy of a quiet neighborhood.

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.

Spacious Colonial in the Rising Sun School District with modern updates and functional living areas. The kitchen features granite countertops and stainless steel appliances, complemented by hardwood, ceramic tile, and carpet flooring throughout. Four bedrooms—including three with walk-in closets—offer ample space, while the primary suite boasts a walk-in shower and dual vanities for added convenience. The home includes 2.5 bathrooms and a finished basement, providing extra living and storage space. Additional features include a two-car garage with updated garage door, a roof installed in 2023, and an owned propane tank for efficient heating. Situated on a lot backing to open farmland, the property offers privacy and wide, unobstructed views. Living Area: 1,880 sq. ft. above grade; total living space 2,668 sq. ft. including finished basement. Due to railings and deck needing repairs NO FHA, VA or USDA

Move-in ready and freshly updated in 2025! This 3-bedroom, 2-bath home offers approx. 1,600 sq. ft. of stylish living on a .387-acre corner lot with public water and sewer. Every detail has been thoughtfully upgraded—appliances and systems are brand new, complemented by luxury vinyl plank flooring throughout. The spacious layout includes a large mudroom and plenty of modern finishes. Located just minutes from Fairlee Creek’s public landing for easy water access, and a short drive to downtown Chestertown and Rock Hall, this home combines comfort, convenience, and Chesapeake charm. PROPERTY CAN BE PURCHASED FOR AN ADDITIONAL COST WITH LISTING MLS #MDKE2005074, 1.8 ACRES SUBDIVIDED INTO 4 LOTS TO MAKE THIS LOT AN ESTIMATED TOTAL OF 2.19 ACRES!

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!

Great rancher in Chester Harbor on the Queen Anne's County side of Chestertown. Fresh paint and carpet throughout. Both bathrooms are completely remodeled. The kitchen could use updating, but the space is great and the appliances are in excellent condition. Plenty of room to add a kitchen island and still have space for a table. Nice 2 car detached pole barn style garage. Fenced back yard. This property has a lot to offer!

Don't miss this beautiful, original owner, 3rd floor unit. Well-kept and ready to move in. 2 bed and 2 full baths with spacious loft that could be used as guest bedroom, office, playroom and so much more. Newly upgraded granite countertops, HVAC and wood floors. Plenty of closet storage and cathedral ceilings in main area and primary bedroom. This is a must see! Just minutes to The Avenue at White Marsh!

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.

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.

Nestled in the charming West End Historic District, this delightful Colonial home, built in 1918, offers a perfect blend of classic elegance and modern comfort. With 1,836 square feet of thoughtfully designed living space, this residence invites you to experience the warmth and character that only a historic home can provide. Step inside to discover beautiful hardwood floors that flow throughout the main living areas, creating a seamless and inviting atmosphere. The spacious eat-in kitchen is a true highlight, equipped with essential appliances including a refrigerator, stove, dishwasher, and disposal, making meal preparation a joy. The kitchen's layout encourages gatherings, whether it's a casual breakfast or a festive dinner with friends. The living room features a cozy gas fireplace, perfect for those chilly evenings when you want to unwind with a good book or enjoy a movie night. Ceiling fans throughout the home ensure a comfortable climate year-round, while the attic provides additional storage or potential for future expansion. This home boasts three well-appointed bedrooms and two full bathrooms, offering ample space for relaxation and privacy. The convenience of main-floor laundry adds to the home's functionality, making daily chores a breeze. Outside, the property sits on a generous 0.14-acre lot, providing a lovely outdoor space for gardening or enjoying the fresh air. Just a short stroll away, the Choptank River beckons with its serene waters, offering opportunities for kayaking, fishing, or simply enjoying the picturesque views. The neighborhood is rich in history and charm, with tree-lined streets and a welcoming community atmosphere. Living in the West End Historic District means you're just moments away from local amenities, including quaint shops, delightful cafes, and parks that invite leisurely strolls or picnics. The vibrant community spirit is palpable, making it easy to connect with neighbors and enjoy the local culture. This home is not just a place to live; it's a sanctuary where memories are made. Experience the perfect blend of historic charm and modern convenience in a neighborhood that truly feels like home.

Kent County welcomes you with a move-in ready home that’s full of updates! This 3-bedroom, 2-bath home sits on nearly a half-acre and is just minutes from downtown Chestertown. Enjoy peace of mind with a newer roof (approximately 5 years old), central heat and air, and a tankless water heater. The home features updated bathrooms, fresh interior paint, and a large laundry room with abundant shelving and space for storage. Outside, you’ll find a spacious yard, storage shed, and access to a wonderful community park with a pavilion and basketball courts. A great combination of comfort, convenience, and value in a desirable location! Kent County has 21 marinas, all within minutes of this location. Live, work and play here in Kent County!

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.

Step back in time with this charming 3-bedroom, 2-bathroom home built in 1890, located in the heart of Preston. Full of character and original details, this home offers a unique opportunity to restore and customize a piece of local history. The inviting living room features a cozy fireplace, perfect for relaxing evenings. A large laundry room and a separate den/office provide flexibility and extra space for modern living.Outside, you’ll find an oversized shop/garage ideal for hobbies, storage, or a workshop. The property also includes a home generator, adding peace of mind. While the home does need some work, it has great bones and endless potential to become a stunning residence once again. Bring your vision and breathe new life into this timeless property.

Move-In Ready Rancher in Cambridge, Maryland! Welcome home to this charming and well-maintained ranch-style property offering easy, one-level living and a warm, inviting atmosphere. Inside, you’ll find a clean and comfortable layout with plenty of natural light and space to make it your own.Step outside to a spacious backyard featuring a versatile concrete slab—perfect for grilling out, setting up a basketball hoop, or adding a shed for extra storage or hobbies. Whether you’re just starting out, downsizing, or looking for a simple and stress-free home, this property checks all the boxes.Enjoy convenient living in the heart of Cambridge, with close proximity to local amenities, shopping, and dining.

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.

Wooded lot located in the waterfront community of Chesapeake Landing. There is a voluntary HOA that you can join for a fee to join to gain access to the boat ramp and Marina. Lot backs up to farm land.

Spacious & Updated Home in Cloverfields on Kent Island. 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. The living room features a large bay window allowing lots of natural light.The newly renovated primary suite features brand new luxury plank flooring, 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 to the driveway area.Major improvements include a new HVAC system, privacy fencing, and new siding and a new roof were completed in October of 2025.12-month lease preferred. Minimum lease of 6 months considered at a rate of $3,000 per month. Landlord requires a security deposit equal to one month's rent, minimum credit score of 650 and minimum monthly income of two times monthly rent. All applicants must apply through Rent spree and applications will be processed accordingly. Tenants responsible for all utilities and general yard maintenance.Are you considering purchasing a home versus renting? Reach out for a lender referral to learn about down payment grant programs and see if you qualify to own this property. This property is also listed for sale under MLS #MDQA2014968 - Owners will remove for sale listing if a lease is signed.

Quaint two bedroom, one and a half bath in downtown Cambridge.This two story duplex apartment has charm and character throughout including built in shelving in the living room and a curved archway going into the dining area. The kitchen has a washer and dryer and space for a small four top or bistro table. Off the dining room, there is a half bath with space for additional storage.Upstairs features two bedrooms and a full bath. Bedroom one is large with three closets and a small balcony. Bedroom two is also an ample size with lots of natural light.End your day relaxing on the covered porch or head just a few blocks over to one of the many great restaurants in town for a bite to eat.Contact listing agent to arrange a viewing. All applicants must apply through Rent spree and applications will be processed accordingly. Landlord covers the heat and water. Tenant responsible for all other utilities. Landlord requires a security deposit equal to one month's rent, minimum credit score of 550 and minimum household annual income of $50,400.