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.

18th century historic home in downtown Chestertown with a separate carriage house! The main home features 3 bedrooms all with en-suite baths. The carriage house has an additional 2 bedrooms and 2 baths with separate laundry and a brick patio. Entrances to the property from Queen St. and Horsey Lane, 2 driveways with plenty of parking spaces. Original wood flooring throughout much of the house. The first floor features a living room, dining room, kitchen, and half bath. New owner to add vanity and toilet to one of the upstairs baths. Second-floor laundry room. Lovely landscaping and fenced-in yard between the main house and the carriage house. Just a short walk to the heart of downtown Chestertown. Definitely a rare find.

Welcome to this charming and elegant 2 bedroom, 2.5 bathroom condo nestled in a tranquil water-oriented community near the Chester River in the historic town of Chestertown, Maryland.This gorgeous home is situated in a prime location, offering easy access to nearby shops, cafes, and restaurants. As you step inside, you'll be greeted by a warm and inviting atmosphere that seamlessly blends classic charm with modern convenience.On the main level , you'll find access from the attached garage or front porch. Off the spacious hallway you have the enclosed Washer/Dryer unit, storage closet and full bathroom. French Doors leading to the first floor study with a bedroom to the left and straight ahead to the downstairs screened in porch overlooking the serene community pond.The upper level features an open-concept living area that's perfect for entertaining. You'll love the spacious kitchen with its stainless steel appliances, sleek countertops, and ample cabinet space. The dining area is flooded with natural light, creating the perfect ambiance for family meals and gatherings with friends. Enter the upstairs porch overlooking the pond with views of the pond, this is true indoor/outdoor entertaining.The upstairs primary suite is a true retreat, complete with a luxurious en-suite bathroom featuring double sinks, shower and stunning finishes. A huge walk in closet completes this experience.This home is also ideally situated within a water-oriented community, providing easy access to boating, fishing, and other water activities. The community offers a dock, boat ramp, as well as grilling areas and a swimming pool for your enjoyment.With its stunning finishes, prime location, and luxurious amenities, this 2 bedroom, 2.5 bathroom condo is the perfect place to call home. Don't miss your chance to experience the best that Chestertown has to offer!

Sprawling brick rancher in a lovely, peaceful setting. Over 2800 sq ft. Large rooms with lots of natural light. Huge family room with cathedral ceilings and fireplace overlooking the ample rear yard. Formal living and dining rooms with hardwood floors and crown molding. HVAC is only one year old. New well pump and WIFI controlled garage door. Water heater new in 2017. Home has a grand, palatial feel with relaxing views from all the windows. Close to Chestertown and a golf cart ride to the Chester River Yacht and Country Club. High speed internet available on site.

A delightful 2 bedroom 1 bath Duplex Condo in the lovely Riverside Terrace community. The unit has been well-maintained and has breathtaking water views from the front yard and both upper and lower decks. Nestled in the heart of Historic Chestertown with easy access to town, the river, shops, Washington College, and hospital. Enjoy the beautiful tree-lined streets of this colonial-era town, the Saturday farmers' market, local theater and everything that Chestertown has to offer.

This sprawling brick rancher will take your breath away! Renovated top to bottom with updated systems, brand new stylish kitchen, luxury bathrooms, rich hardwood flooring, and a fabulous rear patio set on a large deep lot with mature trees. Single floor living with low maintenance ALL BRICK exterior, a 1 car attached garage and plenty of space for the entire gang! Minutes from Rt. 301 and commuting/shopping in Delaware, all set in a picturesque quiet small town with playground park just down the street. RECENTLY REDUCED! Come check it out today before someone else does!

Beautiful, well maintained 3 bedroom end unit townhome. Just minutes from downtown Chestertown. Features freshly refinished hardwood floors, new carpet, new roof, vaulted master bedroom, soaking tub and separate shower in the master bath, 9 foot ceilings on the first floor, walk out second story deck, and an over-sized garage with a workshop. The home is very close to shopping and restaurants. A perfect place for weekends or year-round lifestyle living.

Lovely cottage in Byford Heights, convenient location that's just minutes from the local hospital, shopping and schools. This mid-century home is move-in ready and you can take your time updating as you like...or keep it in it's current mid-century style. With 4 bedrooms and 2 full baths, there is plenty of room for a growing family. Hardwood floors throughout. Attached garage with a nice driveway provides ample parking. Large fenced in back yard with storage shed. Come see this lovely home today!

Just a few blocks away from the heart of downtown Chestertown, this bungalow could be your perfect home, or great investment property. With a large kitchen and dining room for entertaining and a living room with an abundance of natural light, this could be your happy place. The bedrooms are large, one with a half bath attached and the laundry/mud room has plenty of room for storage with a closet and cabinets.

Quiet Community, public water access block away, walking trail, Sunrise and sunset water views. Private fencing on one side, fencing for dogs in back yard. New Patio great for fire pit. Inside new wooden blinds, new luxury vinyl floor, new ceiling fan in living room, new gas stove. TAX free shopping in Middletown Delaware 15 minutes away. This is a very nice duplex.

Welcome to country living! This is a beautiful brick rancher in a beautiful country setting. Enjoy the peace and quiet of the surrounding Kent County farmland. Enjoy the beautiful Hardwood floors and natural colors as you walk through the front door. You will love the rear screened in porch, looking out over the trees and shrubs of Angelica Nurseries. Almost 1 acre of land for you to spread out on. You can stop over to Crow Vineyard and Winery and enjoy the winery and grass fed beef! You are close to Delaware and Tax Free Shopping , close to the water was well, stop down to Turner's Creek Park and Boat Ramp. Lots to do in the area for sure!

Priced To Sell Fast! Charming 2 Level Colonial, Spacious Kitchen with QUARTZ Counters, Stainless Steel Appliances, Modern Tile Backsplash, Spacious Bedrooms, New Custom Paint, Updated Bathroom, Brand New HVAC, New Flooring, Updated Lighting, Driveway, Much More!! Close to Schools, Shopping and Commuter Routes. This Will Not Last!

Lovely well-cared for home in the center of Kennedyville. 3br, 1.5ba 2 story home with large fenced in yard. New roof and flooring installed in 2019. Freshly painted and move-in ready! Should go for any financing type. Easy access to Delaware and points north. Minutes from Chestertown.

1600 SF 3 BR/2.5 BA home that shows like new located in the Village at Kennedyville offers a front porch that overlooks the community pond...full basement and garage...hardwood flooring on the first floor, beautiful cabinetry with a very spacious kitchen pantry

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.

Circa 1743 with a stately 1825 addition, The Inn at Mitchell House is a rare pre-Revolutionary manor home on 9+ manicured acres on Maryland's Eastern Shore. Listed on the National Star-Spangled Banner Trail and just a mile from the Chesapeake Bay, this storied property offers a once-in-a-generation chance to own one of the region's most beloved historic estates.The grounds unfold past champion and organic fruit trees, a generous herb garden, an original 18th-century smoke house, two private bridges over Stoneybrook Pond which are all framed by woods and rolling farm fields.Inside, nine bedrooms and six-and-a-half bathrooms reveal nearly two and a half centuries of craftsmanship: original wood floors, brick floors in the dining room and kitchen, signature Bulls Eye moldings, exposed hand hewn beams, eight fireplaces and soaring 11-foot ceilings.For more than 40 years the property has operated as a successful Bed & Breakfast. An optional furniture package is available for a seamless turnkey transition. Its origins as a single-family residence also make it an extraordinary private estate, full-time home or weekend retreat. A coveted sewer allotment is included with the sale which opens the door for a future carriage house, barn, additional dwelling, stable, studio or expanded hospitality use.A new roof, a complete exterior paint job, new hot water heater, new well pump and updated electrical service were completed in 2025–2026. This delivers the rare combination of historic character and modern peace of mind. Tolchester Marina and the Shanty Beach Bar are a mile away. Rock Hall is six miles down the road and the charming historic district of Chestertown is just ten miles away.After nearly four decades of careful stewardship, the current owners are ready to pass on the privilege and the story of The Mitchell House.

Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore’s 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 promenade 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.

Some Day has arrived. Tucked within 38 rolling acres near Betterton Beach and the Chesapeake Bay, this private equestrian retreat offers space to slow down, reconnect with nature, and awaken to birdsong across the fields. The inviting three-bedroom, three-and-a-half-bath home features a first-floor primary suite, private study, and an attached two-car garage with a loft roughed in for a potential caretaker’s or guest suite. Paddocks, riding trails, a sand ring, five-stall stable, and four-bay machine shed complete the equestrian setting, while more than half the acreage is currently tilled under a farm lease. Peaceful and private, Some Day Farm is a place to breathe deeply and live fully.

Some Day has arrived. Tucked within 38 rolling acres near Betterton Beach and the Chesapeake Bay, this private equestrian retreat offers space to slow down, reconnect with nature, and awaken to birdsong across the fields. The inviting three-bedroom, three-and-a-half-bath home features a first-floor primary suite, private study, and an attached two-car garage with a loft roughed in for a potential caretaker’s or guest suite. Paddocks, riding trails, a sand ring, five-stall stable, and four-bay machine shed complete the equestrian setting, while more than half the acreage is currently tilled under a farm lease. Peaceful and private, Some Day Farm is a place to breathe deeply and live fully.

This over 5 acre waterfront estate on Churn Creek is a true Eastern Shore recreational property. Besides the home itself, the grounds include a board and batten cabin to serve as base camp for water sports down by the water, dock with direct access to the Chesapeake Bay, barn with a stall for your horse or sheep, and detached 2 car garage with lounge area above. Here you can enjoy the abundance and lifestyle of the Eastern Shore with crabbing, fishing, hunting, water skiing, sailing and hikes on the nature trail all available on site. Outdoor living is huge here with multiple spaces to connect with nature and enjoy the privacy of your own waterfront sanctuary. The home is the perfect size for a weekend getaway or full time residence with a floorplan that has been expanded and opened up to accommodate the amazing views and 2026 lifestyle. Storage is a breeze with a full basement including a shop and rec room for grandkids or guests to go enjoy with privacy. One floor living makes for an easy flow with the primary suite opening to a brick patio with sliders and including both an ensuite bathroom and walk in closet. The blend of amenities on site and proximity to Chestertown's Historic District make this the perfect magnet house to attract friends and family or an amazing investment opportunity.

Welcome to a breathtaking country estate where modern elegance, architectural grandeur, and total sanctuary converge across 2.23 serene acres. Spanning over 4,000 square feet of meticulously refined living space, this extraordinary five-bedroom residence has been thoughtfully crafted to offer both lavish entertaining possibilities and effortless multi-generational comfort.Upon arrival, the welcoming foyer makes a memorable first impression, framed by detailed custom millwork and flanked by a private executive office and a sophisticated study or formal dining space. Moving inward, the magnificent two-story great room commands attention with its soaring ceilings and a cozy gas fireplace crowned by a classic raised brick hearth. At the heart of the main level lies a gourmet kitchen designed for grand gatherings, showcasing fresh luxury vinyl flooring, select new appliances, and a stunning quartz-topped center island with a prep sink that easily reconfigures for multi-purpose hosting. Sunbeams flood the adjoining sunroom, creating a seamless transition to the outdoors while mirroring the warmth of the home’s main-floor primary suite. This private retreat features a spacious walk-in closet and a newly remodeled, spa-inspired bath complete with new quartz double vanities, sleek updated fixtures, a large walk-in shower, and an exquisite standalone soaking tub.Offering unmatched independence and comfort, a fully self-contained ground-level suite on the lowest level serves as the ultimate in-law or guest quarters. Complete with its own private ground-level entrance, open-concept kitchen and living area, dedicated laundry, and an accessible bath with a walk-in shower, this wing ensures total convenience without sacrificing style. A new addition to the lower level unlocks movie-theater magic with a fully furnished screening room ready for immediate enjoyment. Upstairs, four generously proportioned bedrooms accompany a beautifully refreshed hall bath.The exterior grounds are nothing short of a resort-style paradise. Step out onto the back porch to take in sweeping views of the lush landscape and expansive partially fenced yard. The sparkling inground pool serves as the crown jewel of the outdoor space, newly upgraded with all-new mechanicals including a dedicated heater. Surrounding the water, extensive custom hardscaping leads to a fireside gathering area, while an oversized gazebo with an outdoor fan offers a shady retreat on warm afternoons. With a brand-new roof installed in 2026, a newly resurfaced driveway, and space remaining for future additions, this estate represents a rare opportunity to experience sophisticated countryside living at its finest and, less than 5 minutes from Chestertown's restaurants, shopping, and Farmer's Market.Updates to the home are available in Documents

Built in 1780/1840, Highcroft is in the heart of the Historic District near the Chester River. A rare in-town property that offers a 2-car garage with a second floor and a long driveway for tons of off-street parking. 3 bedrooms, 4 full baths and 1 half bath. Primary bedroom has his and hers private baths. 8.2 kw solar array on the garage. EV level 2 charger. Easy room flow from front to back for entertaining. Just steps to restaurants, bars, and shops. This is an ultra efficient green house.

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 boat slip - #49 - 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.

Country elegance at its finest with this recently updated and spacious Cape Cod in the water oriented community of Clearview, just minutes from historic Chestertown. The amenities here are a major plus with Franklin pond and community access directly to Churn Creek. The home has had a transformation in the last 2 years with updated bathrooms, floors, kitchen, landscaping, and a new HVAC unit. The main floor master suite allows you to live in luxury with two walk in closets, hardwood double doors, and brand new bathroom with soaking tub and walk in steam shower. Upstairs is a blend of spacious bedrooms and bathrooms galore with an office nook to look out at nature. Storage is no issue with a full basement ready to take on as many holiday decorations as your heart desires. The property is sprawling on over 4 acres that abut the community pond and green space. Outdoor living is celebrated here with a massive deck out back for entertaining and covered front porch for birdwatching. The abundance of our Eastern Shore is just a short ride away with local staples such as Red Acres Hydroponics and Lockbriar Farms for your produce right in Worton and the Chestertown Farmer's Market for the rest. Invest wisely while improving your quality of life.

Experience the warmth and charm of in-town living in this beautiful residence in Chestertown's Historic District. Just a few blocks from the waterfront, shops, galleries, and restaurants, it offers the perfect balance of walkability and tranquility on one of the district's quietest streets. The thoughtfully designed layout makes excellent use of every square foot, while tasteful updates fill the home with natural light. A spacious screened porch extends from the dining room, offering a peaceful place to relax and enjoy the character of the neighborhood. The fenced backyard is a gardener's dream, featuring lush landscaping, vibrant plantings, and beautiful hardscaping that create a private outdoor sanctuary. A rear entrance with off-street parking adds everyday convenience while preserving the home's charming streetscape. This exceptional historic property offers an outstanding lifestyle less than two hours from Washington, DC, and Philadelphia.

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

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

Gorgeous house on River Rd in the Queen Anne's County side of Chestertown. 3 total bedrooms and 2.5 baths. The main bedroom is on the first floor. Stunning sun room, patio and pool. 2 car garage. Living room and den.

The Pearce House has been a testament to fine Eastlake Victorian architecture since it was constructed by famous early Eastern Shore builder H.M. Stuart for Judge James Pearce who held the highest court in the State. The home boasts 6 fireplaces, ornate millwork all over, stained glass windows, soaring ceilings, massive pocket doors, spacious rooms, and surprisingly ample closet space. Homes aren't built like this anymore making adventuring the halls an absolute treat. Water views can be found from various windows of the home with specific angles highlighted seasonally. Outdoor living is celebrated with screened in porch flowing out back from the kitchen, covered front entry porch and second floor covered sleeping porch. The yard itself is a sanctuary with mature azaleas, magnolia, and gingko creating a calming setting. There is a driveway and your car can just stay there because this home is located just blocks walking from all of the dining, shopping, and culture that Chestertown has to offer. This home is part of the Maryland Historic Trust. Own a piece of American history less than two hours from DC, Baltimore, and Philadelphia while enjoying the walkable lifestyle of Chestertown's Historic District.**Interior professional photos are coming soon and are going to be really special**

The luxury of living here is not in the square footage. It is in the untouched beauty of the river and constant exposure to nature. A charming oasis on the Chester River with 3 outbuildings all with the most amazing view. Magnificent plantings around the property. A duck blind for hunting. Private dock with lift. Historical ferry road is yours! The house was completely renovated in 2011. It's all so charming and extremely well kept. Roughly a quarter mile of waterfront. BAT septic system only approved for 1 bedroom. You cannot expand the house.

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

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

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

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

Built in 2018, this custom coastal raised home is ideally located just one block from the Chesapeake Bay, offering the perfect blend of relaxation, recreation, and investment potential. Enjoy easy access to Rock Hall’s 12 marinas, Ferry Park Beach, local restaurants, shops, and charming downtown—all just a short walk, bike ride, or drive away. Nature lovers will appreciate the close proximity to Eastern Neck Island National Wildlife Refuge, where you can explore by foot, kayak, or bike.Designed for both everyday living and entertaining, the home features an oversized two-car garage with abundant parking—ideal for storing kayaks, paddleboards, bikes, jet skis, and more. The spacious, private backyard sets the stage for gatherings with a fire pit and over 1,000 square feet of wraparound decking invites you to take the party upstairs. A covered porch offers the perfect spot to relax and enjoy summer storms or gentle coastal breezes, and the outdoor shower makes rinsing off after a day on the Bay a breeze.Inside, you’ll find beautiful hardwood floors throughout, generously sized bedrooms, and a thoughtfully designed layout. The primary suite includes dual closets—one being an oversized walk-in—a full en-suite bath with tub/shower combo, and private deck access complete with a TRX workout area. The main living level showcases a bright, open-concept floor plan with stunning 360-degree views, ideal for entertaining. The top level features stainless steel appliances, granite countertops, and walls of windows that flood the space with natural light and capture glimpses of the Bay.Multiple sliding glass doors on every level seamlessly connect indoor and outdoor living, making the expansive decks a true extension of the home.Furnishing will be offered to be purchased making this turnkey, this property also boasts a proven rental history with three years of returning Airbnb and VRBO guests—providing excellent income potential for the weeks you’re not enjoying it yourself. Annual income details available upon request.Don’t miss this exceptional opportunity to own your slice of the Bay lifestyle!

Welcome to 14504 John Peel Road, located in a desirable waterfront-oriented community in Galena offering private community dock access and the opportunity to enjoy the Eastern Shore lifestyle. Conveniently located just minutes from Route 301, this spacious 4-bedroom, 2.5-bath Colonial offers over 2,300 square feet of comfortable living space with plenty of room for everyone.The main level features a beautiful kitchen with cherry cabinetry and lvp flooring, a dining area or family room with an electric fireplace, and a convenient half bath. Enjoy additional living space in the screened-in porch, perfect for relaxing and taking in the peaceful surroundings. The front of the home offers two formal living rooms, providing flexible space for entertaining, a home office, or additional gathering areas.Upstairs you’ll find all four bedrooms and two full bathrooms, including a spacious primary suite with a Juliet balcony. The basement offers even more possibilities with a wood stove and additional space for storage, hobbies, or recreation. An attached two-car garage adds everyday convenience.

This cute as a button downtown stunner is recently updated and ready for the next owner to fall in love with the lifestyle that comes with living in the Historic District. Located on a quiet side street just a block from Chestertown's dining, shopping, and galleries, this is the perfect blend of social and tranquil. This means that walking down to Evergrain or Modern Stone Age Kitchen for a croissant and cappuccino before a morning stroll along the waterfront promenade could become part of your morning routine. The thoughtful updates over the years have opened the floor plan and allowed for a modern layout. Many serious upgrades have occurred in the past year including the kitchen and electrical service. The wood burning stove, basement for storage, and garden building are amazing benefits. Invest wisely in an amazing home while improving your quality of life in this incredible community on the water less than 2 hours from Washington DC, Philadelphia, and Baltimore.

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

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.

Seller is super motivated and may have found their next home so this must go! All offers welcomed! Home recently appraised for $501,000.Welcome to 16 Howell Point Road in Betterton, Maryland, where small-town Eastern Shore charm meets comfortable living just a few blocks from beautiful Betterton Beach!This inviting 3-bedroom, 3-bath home offers plenty of space inside and out. The full walk-out basement is partially finished, providing additional living space with endless possibilities for a family room, home office, recreation area, guest space, or workshop.Step outside onto the back deck overlooking the fenced-in backyard, perfect for pets, entertaining, gardening, or simply relaxing at the end of the day. The large driveway provides plenty of parking, while the spacious backyard offers room to enjoy the outdoors.One of the home’s best features comes each evening—gorgeous sunsets stretching across the rolling hills and surrounding farmland, creating a peaceful Eastern Shore backdrop right from your own backyard.Located just blocks from Betterton Beach and the Chesapeake Bay, you’ll have easy access to swimming, boating, fishing, kayaking, and everything that makes this waterfront community such a special place to call home. Whether you’re searching for a full-time residence, weekend getaway, or Eastern Shore retreat, 16 Howell Point Road is ready to welcome you home!

A perfect pied-a-terre or full time residence, this adorable historic home is just steps from the farmers market, shops, restaurants, theater,art galleries and the Chester River. Zoned residential or business. Completely updated in 2021. Metal roof. Loaded with character and charm. Many more pictures to come!

Step into timeless charm with modern updates in this beautifully renovated early 1900s home located in the heart of Kennedyville. Offering 4 bedrooms, 2 full baths, and a versatile third-floor loft, this home seamlessly blends classic character with today’s conveniences.From the moment you arrive, you’ll be drawn to the inviting wraparound front porch—perfect for relaxing and enjoying small-town living. Inside, the home has been thoughtfully updated from top to bottom, including brand new siding, windows, roof, and HVAC system for added peace of mind.The interior showcases a stunning transformation featuring refinished original hardwood floors, fresh paint throughout, and a completely updated kitchen with granite countertops and brand new stainless steel appliances. Both bathrooms have been tastefully renovated, offering a clean and modern feel while complementing the home’s historic charm.Additional highlights include a convenient laundry/mudroom off the rear of the home and a flexible third-floor loft space—ideal for a home office, playroom, or guest retreat.Out back, you’ll find a detached carriage house equipped with electric (100 amp service), heat, and A/C—perfect for a workshop, studio, or additional storage.Situated in the quaint town of Kennedyville, this property offers the perfect balance of historic character, modern upgrades, and small-town charm.

This unique mixed-use property offers exceptional flexibility and opportunity just outside the town of Rock Hall. The first floor features a versatile storefront currently operating as a bookstore, with a history of successful uses including a fabric studio, pottery studio, marine engine shop, and appliance store—showcasing its adaptability for a wide range of business ventures.The second-floor residential space provides comfortable living with an eat-in kitchen, formal living room, family room, one full bath, and two bedrooms. A spacious rear deck extends the living area outdoors, perfect for relaxing or entertaining.Additional improvements include a 35’ x 28’ pole barn and a 28’ x 14’ shed currently utilized as a bookstore event space, adding even more functional possibilities. The property also features a beautiful garden area ideal for outdoor gatherings and enjoyment.With its prime location just outside Rock Hall, this property blends commercial opportunity with residential comfort in a highly desirable setting.

Welcome to the sought-after Elk River Basin community, where comfort, convenience, and the Chesapeake Bay lifestyle come together. This exceptionally well-maintained ranch home offers approximately 1,550+/- square feet of living space and is situated on a spacious 0.46-acre lot.The home features three bedrooms with the potential for a fourth bedroom, along with 1.5 bathrooms, including a private half bath in the primary bedroom. The spacious living room boasts cathedral ceilings and flows seamlessly into the kitchen and dining area, creating an open and inviting floor plan. A remote-controlled window blind in the living room provides added convenience, while Andersen windows enhance the home's quality and energy efficiency.Sliding glass doors lead to a large rear deck with a pergola, perfect for outdoor entertaining, and a screened porch offers seasonal winter views of the Elk River.A unique feature of this property is the additional room currently used as an in-home hair salon with its own private entrance, making it ideal for a home business, office, studio, or hobby room. An additional 12' x 8' bonus room provides flexible space that could serve as a fourth bedroom, home office, exercise room, or additional storage.Recent improvements include a new roof, gutters, and Gutter Guards, providing added value and peace of mind.Residents of Elk River Basin enjoy community water access, a community playground, and a private beach area accessible by a short golf cart ride. Conveniently located just minutes from marinas, waterfront dining, shopping, and the historic town of Chesapeake City, this property offers easy access to local attractions while maintaining the charm of a water-oriented community.Located in the highly desirable Bohemia Manor School District, this move-in ready home offers an excellent opportunity for year-round living or a peaceful weekend retreat.

$5,000 credit towards upgrades! Welcome home to this beautifully maintained Colonial nestled in the desirable Meadows community of Church Hill. Ideally located between historic Chestertown and Centreville and within the sought-after Queen Anne's County School District, this home offers the perfect blend of comfort, convenience, and timeless style.Step inside through the impressive two-story foyer that welcomes you into a bright and inviting floor plan. The spacious primary suite serves as a private retreat, complete with a, separate shower, and relaxing soaking tub. The home has been exceptionally well cared for and features numerous updates, including a newer roof and HVAC system, providing peace of mind for years to come. New HVAC system installed and serviced by Dixieland energy January 2025, operated by Nest technology. New Roof in July 2025 installed by Economy Roofing with GAF Timberline HDX Lifetime Shingles. New 16x12 Trex Deck with a large poured concrete patio installed in 2024-2025.The partially finished full basement offers endless possibilities with plenty of room for a recreation area, home gym, office, or additional storage. Outside, you'll fall in love with the beautifully landscaped backyard oasis—perfect for entertaining, summer barbecues, or simply relaxing after a long day.With its outstanding condition, thoughtful updates, attached garage, and prime location just minutes from shopping, restaurants, and easy access to Route 301, this is a home that truly checks all the boxes. Schedule your private showing today and experience everything 116 Reeand Lane has to offer!

Buyer's remorse means this house is again available at an amazing price! Spacious home in Kenndyville with lots of amenities. Featuring 4 bedrooms and 2.5 baths with a large kitchen with granite countertops, living room with gas fireplace, 2-car detached garage, and a huge unfinished basement. Plenty of storage. Deck off the living room leads to a partially fenced back yard. Just a short drive to downtown Chestertown.

Sweet Victorian in downtown Betterton, just a short walk to Betterton Beach. Home has been lovingly cared for by the same owners for nearly 50 years. The main floor features the living room, dining room, and kitchen. As well as a laundry room with half bath, an office, an entry room in the front, and mud room in the back. On the second floor you will find 3 bedrooms and a full bath. On the 3rd floor is another bedroom that could also be used as a family room, hobby room or office. Out back, there is a driveway with parking for 2 cars. The rear yard is perfect for entertaining with a deck, patio and covered pergola. Brand new oil furnace. Mini splits in most of the rooms. This property is quaint and charming and would be perfect as a beach home or a full time residence.

Welcome to this beautifully updated country farmhouse, where classic charm meets modern comfort in a serene rural setting. Thoughtfully renovated throughout, this inviting home offers a spacious first-floor primary suite, two additional bedrooms, and generous walk-in attic space—perfect for storage. The main level has been freshly painted and features new flooring, creating a bright, move-in-ready atmosphere. Efficient mini-splits provide comfortable climate control throughout the home, with capacity for one more unit if desired. Step outside through the newer French doors into a fully fenced backyard, ideal for pets, gardening, or simply enjoying the peaceful surroundings. Recent updates include 6 mini-splits, a new hot water heater (installed 11/25), a front roof that is 5–7 years old, and a rear roof just 5 years old with durable 50-year shingles. The third level boasts newly conditioned bonus spaces, offering flexible living or recreational options. Location is a true highlight. Situated minutes from the Sassafras River, a nearby marina, and popular restaurants including the Kitty Knight Inn and Restaurant, Fish Whistle, and Twinny’s. This property places waterfront dining and recreation right at your doorstep. You’re only one mile south of the Fredericktown boat ramp, making boating and water access effortless. Route 301 is an easy 10-minute drive for convenient travel north or south, and the home sits along the Chesapeake Scenic Byway—your gateway to charming waterfront towns such as Chesapeake City, Chestertown, and more. This remodeled farmhouse blends updated living with timeless country appeal and an unbeatable Eastern Shore location. Don’t miss the opportunity to make it yours.

Dreaming of life by the Chesapeake Bay? Here's your chance! Located on a private road in the sought-after Carpenter's Point community, this beautifully updated 2-bedroom, 1 full bath home offers approximately 1,000± sq. ft. of living space and sits on a rare double lot (Lots 16 & 17) with beach and water access, just a short walk to the beach. The home is NOT in a flood plain (FEMA letter available).✨ Additional features include:✔️ Spacious attic for extra storage✔️ Encapsulated crawl space✔️ Public water & sewer—no well or septic to maintain🚤 The oversized detached garage is perfect for a workshop, vehicle storage, or all your water toys. There's even an additional paved parking area beside the garage for your boat, Jet Skis, or trailer.Whether you're looking for a full-time residence, a vacation getaway, or an investment property, this Chesapeake Bay retreat is one you won't want to miss!

Welcome to 11976 Flour Mill Street in the charming Village at Kennedyville! Nestled in the heart of this small-town community, this well-maintained 3-bedroom, 2-bath rancher offers comfortable one-level living with an inviting open floor plan perfect for everyday living and entertaining alike. Enjoy relaxing mornings on the welcoming front porch or unwind on the spacious back deck overlooking the backyard. Conveniently located just a short drive to Route 301 for easy northbound or southbound travel, while also being close to the historic waterfront town of Chestertown with its local shops, restaurants, and community events. If you are looking for small-town charm with convenience, this home is a must-see!

A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial. Full finished basement. More details and pictures coming soon!

Welcome to 204 S Church Street — a charming 3BR/3BA home in the heart of Sudlersville!This beautifully maintained and thoughtfully updated home offers comfort, style, and modern conveniences. One of its standout features is the spacious first-floor primary bedroom complete with a private en-suite bathroom, offering ease and accessibility rarely found in homes of this style. This home boasts 3-bedrooms and 3 full bathrooms and features a wrap-around porch perfect for morning coffee or evening relaxation.Inside, you'll find an inviting layout with granite countertops in the kitchen, a cozy fireplace in the living area, and dual-zone HVAC to keep you comfortable year-round. The home is equipped with a tankless water heater, ensuring endless hot water and energy efficiency.Enjoy privacy and room to play in the fully fenced-in yard, ideal for pets, gardening, or entertaining. O head over to nearby Sudlersville Park!This move-in-ready gem offers the perfect combination of small-town living and modern amenities.Don’t miss your chance to make it yours!

Welcome to 109 Parma Road in family-friendly Chester Harbor. This well-maintained home is located on a quiet street and has three generously sized bedrooms with hardwood flooring and 2 full bathrooms. An upgraded kitchen featuries granite countertops, SS appliances, and solid wood cabinets with quiet-close drawers. Spacious living room off the kitchen and dining room combo. Spacious and private backyard is perfect for dogs and children. Mature oak trees provide lots of cool shade. Recent upgrades include: bathroom vanities, ceilings fans, light fixtures, microwave, interior paint, driveway crushed run. Chester Harbor is a quiet community with water access to the Chester River for just $15 per year and NO HOA. 5 minutes to downtown Historic Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market. Enjoy country living on the Eastern Shore. Less than one hour to Annapolis. Much more info and professional photos coming soon. Stay tuned!

Price improvement: Colonial in Kennedyville overlooking the pond. Situated on a corner lot with a private driveway behind the house. 2 car attached garage, 4 bedrooms and 2.5 baths. Gas fireplace. Large mudroom with laundry. Partially finished basement with new carpeting. Lovely front porch for relaxing and enjoying the view.

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.

Set within a stately 1800s waterfront home, this beautifully renovated one-bedroom condominium offers an effortless life along the Chester River. Begin your mornings with river views, spend shaded afternoons beneath the trees, or retreat to the floating dock for sunbathing and quiet reflection. With an updated kitchen and bath, kayak storage, off-street parking, and downtown Chestertown’s shops and restaurants just one block away, 117 N Water Street, Unit 3B is a maintenance-free escape within 90 minutes of Washington, D.C., and Philadelphia.

Clean, classic mid-century style ranch with REAL wood floors. archways, knotty pine kitchen, a big front porch, large yard, off-street parking and bonus alley access in rear with possible room for a detached garage (buyer to verify) New upgraded electrical service and GFCI outlets, fresh paint, floors refinished and more. Walk to conveniences from this move-in ready charmer in upper Chestertown.

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! Owner had a pre home inspection for your convenance! The home is good to go!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.

GREAT NEW PRICE!! MOTIVATED SELLER!Welcome home to this stunning end-unit townhome located in the heart of Elkton, MD! Boasting 3 spacious bedrooms and 1.5 baths, this home is packed with features you'll love. The main level welcomes you with gorgeous vinyl plank flooring and an abundance of natural light. You will fall in love with the kitchen, featuring elegant granite countertops and a sliding door that leads out to a private back deck—perfect for outdoor entertaining. NEW ROOF, NEW SUMP PUMPEnjoy the ultimate convenience of first-floor laundry. Upstairs, the massive primary bedroom serves as a true retreat. Two additional bedrooms are also on the second floor. Looking for extra space? The partially finished basement offers a versatile bonus room tailored to your needs. Situated in a prime location convenient to I-95 and just minutes from the Delaware border for tax-free shopping.

Welcome to easy, low-maintenance living in a location that's hard to beat! Conveniently situated near the University of Delaware, major highways, shopping, dining, and everyday amenities, this home offers the perfect combination of affordability and accessibility.Designed for those who want to spend less time on home upkeep and more time enjoying life, this property is an excellent opportunity for first-time buyers, investors, or anyone looking to downsize.The home has been well cared for but does have some deferred maintenance that has been reflected in the price. It is being offered AS-IS. The seller will not make repairs except for lender-required repairs, which will be considered at the seller's sole discretion.If you're looking for a home with tremendous value, a prime location, and the opportunity to make it your own over time, this is one you won't want to miss!

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.Seller is offering a $5,000 credit to the buyer !!Property sold AS- IS Seller will make NO REPAIRS

Investor special! This property needs to be fully rehabbed. Great location in the highly sought after neighborhood college Heights.A diamond in the rough and ready for new owners. Highest and Best by 5PM 8/12/26

This is a unique opportunity to invest in cleared and level acreage just off one of the Eastern Shore's commercial corridors and a few minutes from Downtown Chestertown. Suburban Commercial Zoning allows for a variety of possible uses.

Great Investment Opportunity – Fixer-Upper on 1 Acre LotAttention DIYers, investors, and renovators! This small home, located on a beautiful 1-acre lot, is a diamond in the rough, offering endless potential for the right buyer. Nestled in the quiet, rural setting of Quaker Neck just 1.5 miles from downtown Chestertown, this property is the perfect canvas for a major rehab project.The home, which is in need of significant repairs and updates, is being sold as-is, providing a great opportunity to bring your vision to life. Whether you're looking to restore it to its original charm or transform it into something entirely new, this property offers a solid foundation for your renovation ideas.Property Highlights:* 1-acre lot with plenty of space for expansion, gardening, or outdoor activities* Small house with potential to become a cozy retreat or a profitable rental* Quiet, rural location for privacy and peace of mind* Easy access to Chestertown for shopping and Quaker Neck Landing for water fun!Please note: This home needs extensive repairs and will not qualify for traditional financing, so it's ideal for cash buyers or those with renovation experience. Buyer to perform due diligence. Sellers are willing to provide architectural drawings & site plans for their planned renovation.Don’t miss this opportunity to turn a fixer-upper into your dream home or next big project. Schedule a showing today and imagine the possibilities!

Located on the upper Chester River in Millington, River Bend Lane offers the perfect blend of convenience and waterfront lifestyle just seconds from Route 301 for easy commuting. Skip the hassle and expense of a perc test — the owners have already secured public water and sewer allocation, making the building process that much easier. Enjoy kayaking, fishing, and peaceful river views right from your backyard while surrounded by beautiful natural scenery and abundant wildlife. A rare opportunity to build your dream home with both convenience and waterfront charm.

(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. Unsuccessful land evaluation completed on May 26,2026 for a conventional septic. You will need to reach out to the County for highest and best use or to talk about an alternative septic system. 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.

Entire historic home in downtown Chestertown for a great price!! One block from shops, restaurants, galleries and much more. Large living room opens to eat-in kitchen with beautiful countertops and all stainless steel appliances. Half bath and laundry on main floor and 3 bedrooms and two full bathrooms upstairs. Hardwood floors throughout. Private backyard with fence and storage shed. Dead end street has plenty of parking. Convenient location and great price! Available immediately, one year lease minimum, tenant to pay electric and quarterly water/sewer. Rental application fee paid by tenants. Do not enter property without an appointment. Call for details and online application.