243 properties for sale in Chestertown town

Opportunity awaits at 108 Groff Road in Millington, MD! Bring your vision and creativity to this spacious Cape Cod-style home situated in a peaceful, wooded setting. Featuring a versatile floor plan, generously sized living areas, dormer windows, and a charming covered front entry, this property offers plenty of potential for customization. The home includes a spacious kitchen and living areas, an upper level with additional living space, and a bathroom featuring a jetted soaking tub. Mature trees provide natural privacy, while the rear deck offers an opportunity to create an inviting outdoor retreat. Whether you're an investor looking for your next renovation project or a buyer ready to transform a property into your dream home, this is a chance to build equity and make it your own. Property is in need of renovation and is being sold as-is. Bring your imagination and discover the possibilities!

Offer deadline tomorrow Sunday, October 18 at 2pm*. Welcome home to Chesapeake Landing! Tucked back in this quiet water-access community, this 3 bed, 1 bath rancher offers 1,008 square feet of easy, low maintenance one-level living on a. 37 acre lot with plenty of room to spread out. As you walk into the front door, you enjoy a lovely living space with an open floor plan leading into the kitchen. Down the hall, you have 3 bedrooms and a newly renovated bathroom. This home has been meticulously maintained and updated from top to bottom over the last 4 years including a new roof, new HVAC, new flooring throughout, a water conditioning system, all new stainless steel appliances, a new storm door, and more. Theres so much to enjoy nearby. Launch your boat from the community ramp at Worton Creek Marina and spend the day on the water. Then end it with dinner at a local favorite, The View at Worton Creek. This home is located just a short drive from Chestertown, Rock Hall and the Safe Harbor

The Perfect Maryland Retreat with Chesapeake Bay Views Close By. Experience the quality of a custom-built Cape Cod crafted by a reputable local builder. Lovingly maintained by its original owner, this home is completely move-in ready and features a freshly painted interior throughout. Whether you are looking for a full-time residence, a weekend getaway, or a holiday retreat, this property offers a peaceful escape. The home features a Chestertown address but sits closer to Rock Hall, giving you the absolute best of both worlds. You are perfectly positioned to enjoy the vibrant Rock Hall festivities and marinas, while still being just a short drive from the famous Chestertown Farmers Market and Historic Downtown, with their variety of Festivals and events throughout the Year. Arrive via the welcoming, roomy front porch, an inviting space to sit, relax, and take in the quiet surroundings. Inside, the main level features an open floor plan where the living room, anchored by a cozy propane

Welcome to 105 E Brook Drive, located in the sought-after North Brook community of Centreville, MD! Situated on an oversized corner lot with plenty of room to expand, this beautifully refreshed home offers 4 bedrooms, 3.5 bathrooms, and the space and flexibility today's buyers are looking for! Step inside to discover gorgeous refinished hardwood floors, fresh paint throughout, and new carpeting (2026), creating a bright and inviting atmosphere. The kitchen features brand-new appliances (2026), while a new tankless water heater (2026) adds modern efficiency and convenience. Upstairs, the spacious primary suite offers a relaxing retreat, complete with two closets and a private bathroom featuring tile floors, a soaking tub, and a separate stand-up shower. The fully finished basement provides incredible additional living space, perfect for a recreation room, home office, entertaining, or hosting guests. Outside, enjoy the patio overlooking the expansive backyard, offering endless possibili

Just a 2 blocks from Rock Hall Harbor which accesses the Chesapeake Bay, this adorable Cape Cod is the retreat youve been dreaming of. Whether youre looking for a peaceful primary residence, a weekend or vacation getaway, or an investment property to Airbnb, this home perfectly balances cozy character with nearby conveniences. Peace and quiet doesnt mean being disconnected. You're just a short stroll or drive from downtown shops and dining, giving you the best of water community living and small-town convenience, such as quaint downtown shops, restaurants like Harbor Shack, Rock Hall Brewing Company, The Little Lemon Leaf Diner, Ford's Seafood, ice cream from Get the Scoop, and much more. Yearly Rock Hall events such as the renowned Pirates and Wenches Weekend, 4th of July Celebration, FallFest, Blessing of the Fleet, Waterman's Day, the Lighted Boat Parade (and so much more) will keep you entertained all year long. Inside the home, enjoy a roomy living room and dining room area that's

One-acre colonial w/ saltwater pool & leased solar | 4 br, 2.5 BA | FARMLAND VIEWS | ONE MILE FROM ROUTE 301 | FENCED YARD | ATTACHED GARAGE W/ PLENTY OF PARKING Set on a one-acre lot backing to farmland, this four-bedroom, two-and-a-half-bath Colonial offers a country setting with easy access to Route 301. Cathedral ceilings and natural light give the interior an open feel, while the fireplace provides a comfortable gathering spot. An attached garage and a large driveway offer plenty of parking. The fully fenced backyard includes an in-ground saltwater pool, with additional space for gardening, outdoor games, and entertaining. The pool needs repairs (the seller will pay), offering an opportunity for the next owner to bring it back into use. Solar panels are installed on the home and are leased (documents reflect good savings). With plenty of room to spread out both inside and out, this home is ready for everyday living and time spent outdoors

Discover the Charm of Kinnairds Point in this beautiful mid-century modern home. A sloping, wooded wonderland just minutes from historic Chestertown, this inviting and energy-efficient home offers the perfect blend of privacy, comfort, and Chesapeake Bay living. Set on just over two beautifully landscaped acres, the property features mature trees, fruit trees, spectacular plantings, and a peaceful, private setting surrounded by nature. Designed for both everyday living and effortless entertaining, the home offers three bedrooms and two updated baths on the main level, along with hardwood floors throughout. The updated gourmet kitchen opens to the dining and living areas, where a wood-burning fireplace creates a warm and welcoming gathering space. The updated screened porch and new, expansive deck bring the outdoors in and provide wonderful places to relax, entertain, and enjoy the natural surroundings. The spacious lower level adds exceptional flexibility, with a comfortable family roo

Chase the sunset daily at this exceptional waterfront beauty, perfectly perched on 3.12 private acres with no HOA. Just off Reed Creek overlooking the Chester River. Completely rebuilt inside and out in 2019, this stunning retreat offers nearly 1,900 square feet of one-level living with three bedrooms, two full baths, and additional home office/ flex-space. Built to entertain, the home features 900-square feet of wraparound Trex deckingan inviting setting for waterfront dinners, gathering with friends, or simply unwinding as the sun slips away. A 150-foot pier, built in 2020 and equipped with an 8,000-pound boat lift, puts days on the water within easy reach. A large outbuilding. Approx. 28' x 24'. With electric provides flexible space for hobbies, storage, and projects. Encapsulated crawlspace for peace of mind. Privacy, room to play, and waterfront living come together beautifully. Dont miss your opportunity to make this gorgeous, private retreat your everyday escape

Welcome! You Will Never Need To Spend Another Vacation in Someone Else's Home. Vacation in your own home all summer long! This is a Beautifully Cared For Home, And Is Fully Furnished, Just Show Up And Enjoy The Comfy Home, With Two Bedrooms And A Fold Out Sofa Bed Too! A Super High Ceiling Pole Building/Garage For Your Car, Golf Cart, Equipment Or Boat Storage! Indian Acres Campground Is A Boaters Dream, You Have Your Own Year Round Boat Storage! Open Access To The Community Boat Launch! Huge Screen Porch, Large Deck, Shed, Garage And Plenty Of Parking On The Spacious Corner Lot That's Located Right Around The Corner From The Community Pool, Pavilion And Recreation Area! The Indian Acres Gated Community Is a Great Vacation Get Away With So Much To Do, Or Just Relax. The Golf Cart Friendly Community Makes For Getting To The Pools And Waterfront a Breeze! Plus, Boat Ramp, Lake, Two Ponds, Convenience Store (With Great Food), Arcade And So Much More. Come See All That This Community Has T

Welcome to 116 Frederick Drive in Centreville Maryland. Be Sure to Click the Virtual Tour! This property has been meticulously cared for by the current owners, and it shows! The property sits on. 34 acres. Pride of ownership shines through in this gem of a home. This property gives you plenty of space both inside and out. You will be welcomed home every day by your beautiful lawn and established landscaping. There is plenty of parking available with your own attached garage and asphalt driveway. There is Luxury Vinyl flooring throughout the home. The property has a spacious backyard complete with a fence, a concrete patio and a pergola perfect for entertaining. Enjoy tons of natural light in the spacious kitchen where laminate countertops are partnered with a Stainless-Steel Refrigerator, a built-in microwave and stove. The tile flooring in the kitchen means easy maintenance. The Livingroom includes built-in shelves and an electric fireplace. The upgraded banister really makes the room

Welcome to 8630 Elm Road, where comfortable living meets the relaxed pace of Marylands Eastern Shore. Located in the water-oriented Tolchester Estates community, this refreshed five-bedroom, 2.5-bath home offers approximately 1,936 square feet of flexible living space on about 0.38 acres. Begin the day with a quiet moment on the furnished front porch, then enjoy a versatile interior with room to work from home, welcome overnight guests, and spend time together. The fifth bedroom can serve as a private home office, guest room, hobby room, or other flexible space separate from the main living area. Attractive ceiling fans throughout the home add comfort and style. The refreshed kitchen features bright white cabinetry, a French-door refrigerator, stainless-steel appliances, and a spacious adjoining dining area with room to gather and enjoy meals. The main living ar Start the day with a quiet moment on the furnished front porch, then enjoy a layout with room to work from home, welcome gues

Lock the door, grab your coffee, and walk. Directly across from the Chestertown Marina in the heart of the Historic District, 204 S Water Street is the pied-terre the Eastern Shore was made for. Thoughtfully restored, the home pairs period character with an open, easy-living floor plan and a full bath on the main level. Out back, the rear porch and low-maintenance yard are made for slow mornings and long summer evenings. Step out the front door to the Chester River, Wilmer Park, and the marina. Stroll a few blocks of brick sidewalks to galleries, cafs, the oyster bar, live theatre, and the Saturday Farmers Market. Tall ships at Downrigging, jazz in the park, sunsets on the river: it's all right here. About 90 minutes from DC and Philadelphia, it's close enough for every weekend and charming enough to stay for good

Price increase due to the homes expanded footprintover 1,200 additional square feet! *.*To be built! Welcome to this beautifully designed3,540 sq. Ft. home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The standard floor plan includes4 bedrooms and 3.5 baths, with the option to expand to5 bedrooms and 4.5 bathsby adding a first-floor guest suite. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining areaperfect for entertaining. Upstairs, the primary suite features a spa-like bath and walk-in closet, complemented by a convenient second-floor laundry. Designed with future needs in mind, this home also offers the option of aresidential elevatorfor effortless access across all levels. Enjoy broad water views and breathtaking sunrises over the Chester River. The covered porches and expansive windows create a seamless connection to the outdoors, enhancing the waterfront lifestyle of this sought-after communi

Ask about our SELLER-PAID RATE BUYDOWN the builder is paying to permanently lower your interest rate when you finance with our preferred lender, who is also contributing toward your closing costs. The result: a dramatically lower monthly payment on a brand-new home, saving you well over a hundred dollars every month even more on lower-down-payment financing. This is real payment relief in today's market often the difference between watching and owning. Brand-new construction in the heart of Chestertown. Buydown applies with use of preferred lender; see agent for details. Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs youll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. A

This ranch home in the water access community of West View Shores has become available! A 2 bedroom, 1.5 bath home is perfect for a first home, a downsizing home or a weekend home! Recently updated (mostly in 2020), there is a newer roof, newer siding, newly finished sunroom with new flooring and an updated feel! Home is very open and breezy in the warm months and warm and cozy in the winter months! The community is highly sought after as it offers a great location to visit rivers to both the north and south. There is a community boat ramp, fishing pier and private community beach. Bring your golf cart and join in on a lifestyle many only dream of. Call Lori today for a private tour!

Welcome home to this beautiful Cape Cod located in Corsica Landing Estates, along the Corsica River. This home features three ample sized bedrooms, two full baths, a separate kitchen, dining and living area. While it has plenty of space inside and out, the potential for more living area is yet to be discovered. This home has a fully framed unfinished second floor. While the current septic system is in perfect working order, QAC and a septic company have determined that with an upgrade to a BAT system and extension of the drain fields, you can have an additional one to two bedrooms and another bath. This home just needs you and your design plans! If that isn't enough the home is located just a stone's throw away from the Centreville Wharf where you can launch your boat, fish from the dock or just relax in the park area or let the children roam and enjoy the playground. There are so many other great amenities nearby from restaurants and shops to grocery stores, the YMCA and so much more

Custom-built rancher situated on more than 1.8 acres in the Kentfield community of Worton. Designed for one-floor living, the home offers a spacious, functional layout along with an unfinished basement that provides plenty of room for storage, a workshop, or other possibilities. The large kitchen features a breakfast area, generous cabinet and counter space, and a center island with propane cooktop. The living room includes built-in cabinetry, a propane fireplace, and a slider door leading to the screened porch overlooking the private backyard. The living room opens to the dining area and entry, creating an easy flow through the main living spaces. The primary suite includes an en-suite bath with two walk-in closets, dual vanities, a separate shower, and jetted tub. Two additional bedrooms share a full hall bath, while a separate office offers flexible space and could serve as a fourth bedroom. The two car, side entry garage has access to the basement. Outside, the large backyard is su

Exceptional custom live/work space located on 5 acres at the entrance of Rock Hall. Newly constructed in 2019. This home boasts a screened porch, open living space with hardwood floors, encapsulated crawl space, metal roof, efficient ductless mini-splits, and sophisticated vaulted ceilings. This professional artist studio was completed with architectural lighting, seamlessly lighting the space for the everyday or a special occasion. Currently used as an artist studio, this home and property have the potential to be whatever you desire. The open living space would make an inviting home, perfect for entertaining. The tucked-away loft bedroom is spacious and has exceptional views of the surrounding woods. There is plenty of room on the 5-acre parcel to expand or customize! Prime location with tons of privacy. This gem is tucked away, yet just a short jaunt to all Rock Hall has to offer: marinas, restaurants, Main Street shops, public boat launches, and the Ferry Park beach! Showings by ap

Classic home on South Main Street in the town of Rock Hall. Charming in-town farmhouse-style residence on a spacious lot. 36 acres, plus a large garage/ workshop with electric! Step inside to discover a warm and inviting interior. Original solid hardwood floors throughout, traditional floor plan with classic build-ins. The heart of the home is the large country-style kitchen, with ample table space and a pantry. The adjoining family room has a cozy propane fireplace with glass doors, which keeps this home very cozy! The formal dining room gets lots of natural light and leads to a large mudroom/ rear entry. There are three spacious bedrooms upstairs, as well as a half bathroom. There is a full bathroom downstairs. This home is ready for its next chapter. A great opportunity to renovate a property with solid bones in the heart of town! The large yard gives you privacy and room for activities while still being downtown. Walking distance to all Rock Hall has to offer, marinas, restaurants,

Nice old home in Rock Hall located on Main Street that needs some TLC. 4 bedrooms, 2 1/2 baths, upgraded kitchen, bath, Florida room and rear deck. Maintenance free exterior (new shingles 2022) and fenced yard. Short walking distance to downtown, shopping, Churches. A short drive to the Chesapeake Bay, Public Landings and Eastern Neck Wildlife Refuge

Some houses are finished. This one is full of opportunity. Built circa 1920, this Victorian sits in one of Downtown Chestertown's most desirable neighborhoods and it's waiting for someone who can see what it is meant to become. The hard work and the expensive work have already been done: new cedar siding, blown-in insulation, and original hardwood floors throughout. What remains is the fun part. The kitchen and baths are a genuine blank slate, ready for your design, your finishes, your vision. And the bones remarkable. Solid construction, generous proportions, and historic detail at every turn the kind of craftsmanship that simply isn't built anymore, and can't be bought back once it's gone. Start with a house of real character and your renovation adds value instead of merely keeping up. Upstairs, five generous bedroom and two full baths. A rare third-floor primary suite offers space and privacy set apart from the rest of the home a true owner's retreat, a guest wing, or a quiet work-f

Imagine waking to golden light spilling across 7.25 acres of rolling hills, horses grazing in the distance, and the Chesapeake breeze drifting in from Betterton Beach just up the street. Mornings begin with coffee in the sun-drenched sunroom, and the first-floor primary suite turns every day into easy, one-level living. Evenings end with a warm escape to the sauna room in the full basement. Geothermal heating and cooling keeps every season effortlessly comfortable, and fiber optic internet keeps you connected to the world while it feels a million miles away. Beyond the 3 bedroom, 3 bath main house, an attached 2-car garage, a 3-bay garage with a charming 1 bedroom, 1 bath guest apartment, and a detached 2-bay workshop give you room for visiting friends, creative pursuits and every passion project. With historic Chestertown's waterfront dining and shops just a short drive away, this is the Eastern Shore dream, ready to be lived

Discover 6324 Quaker Neck Road, an exceptional waterfront estate spanning over 5 acres along the East Fork of Langford Creek offering over 5 feet of water at low tide. Over 5,900 square feet of refined living space with 5 bedrooms and 4 baths, designed for elegant Shore entertaining and everyday ease. A new private pier with swim platform and boat lift, plus your private beach, extends living outdoors complemented by a detached garage with carriage house and a pole building. Minutes to Chestertown, yet quietly removed a distinguished Quaker Neck offering for the buyer who wants it all

Rare opportunity to own an exceptional 8 acre residential farmette in Church Hill in Queen Anne's County! This versatile property features a 3-story, 4 bedroom, and 1 full bathroom and 2-half bathrooms farmhouse with 2,256 sq ft of living space, including a spacious living room, formal dining room, updated kitchen, sunroom, front porch, and patio surrounded by mature trees and established gardens. Perfect for an equestrian or hobby farm, the land includes 5 acres of pastures and a 2,600 sq ft barn equipped with 5 horse stalls, a large storage loft, an enclosed workshop, electric, and water. A separate 870 sq ft climate-controlled recreational outbuilding with a half bath offers the perfect footprint for a private home office, gym, or guest suite. Enjoy a private, secluded country setting without sacrificing conveniencelocated less than 0.5 miles from Rt 213 and 3.5 miles from Rt 301 for an easy commute. By Appointment Only. The road becomes the private driveway onto the property so vie

Welcome home! This beautifully maintained and updated property sits on a generous. 45-acre lot in a lovely, quiet neighborhood, with a peaceful, wooded backdrop for added privacy. Renovated in 2017, this home offers numerous upgrades and thoughtful improvements, including hardwood floors, newer windows and doors, updated HVAC, and a newer roof. The kitchen features 42-inch cabinetry, granite countertops, and stainless steel appliances, while the custom ceramic-tile bath adds an extra touch of style. Enjoy the best of outdoor living from the fabulous screened-in porch and deck, perfect for relaxing, entertaining, or simply enjoying the tranquil surroundings. A large parking area provides plenty of space for family and guests, and the partial basement offers additional storage or flexible-use space. With so many major updates already completed, there is little left to do but move in, relax, and enjoy! A wonderful opportunity for anyone looking for a move-in-ready home with space, privacy

Price Improvement | Motivated Sellers*. Welcome to 135 Crossgate Drivea home designed for the way life actually happens. Friends gathered in the kitchen. A fire going in the living room on a cool fall evening. A fenced backyard perfect for outdoor entertaining. A dedicated office for working from home. This home offers space to come together and room to spread out when you need it. The main level flows easily from the spacious kitchen and eat-in area into the living room, while a separate dining room provides space for holidays and entertaining. Upstairs, you'll find four bedrooms, including a generous primary suite with a private bath and walk-in closet. The unfinished basement offers flexibility for storage today and the potential for a home gym, recreation room, workshop, or additional living space in the future. A two-car garage provides plenty of room for vehicles and gear, with a walk-in cooler negotiable with the sale. Beyond the home, enjoy a neighborhood with sidewalks, street

Second story, waterfront condo in historic Chestertown. Comes with a private boat slip at the end of the dock. 2 bedrooms and 2 full baths. Spacious patio with a stunning view of the Chester River. One of the most coveted streets in historic Chestertown!

Welcome home to this sanctuary that beautifully blends modern comfort with warm Eastern Shore charm. Nestled at the end of a quiet cul-de-sac in the desirable Willow Branch East community, this property offers a sprawling 1.61-acre lot with. 5 bedrooms. A welcoming front porch leads into a dramatic two-story open foyer featuring an elegant staircase. The main level boasts a bright, flexible formal dining room or home office and a spacious living room. At the heart of the home is a spacious kitchen fully equipped with Silestone countertops, 42' Maple Toffee cabinetry, and brand-new stainless steel appliances, plus a generous keeping room perfect for large gatherings. Transition effortlessly through the cozy family/sunroomcomplete with a stylish barn doorto the rear stone paver patio for seamless indoor-outdoor entertaining. Upstairs, the private primary suite serves as a true sanctuary, showcasing a spacious sitting room and a spa-like en-suite bath with a jetted soaking tub. Four addit

Amazing waterfront community on the Sassafras river. This Kentmore Park home was originally built in 1953. Major renovation in 2006 adding bedrooms, bathroom, basement, large light filled gathering room. The rear deck has space for outdoor dining and privacy. The perfect year round get away or primary residence. Well maintained. Four bedrooms and two baths. Lower level garage and walk out basement. Enclosed lawn and yard equipment storage space. Rear yard gathering area and room for a garden. Lovely pastoral view of farmland. Easy path to beach and central Kentmore Park Community areas. Tax free shopping in Delaware. Convenient shopping in Galena. Check out Cross Street Market for produce, local meat, specialty foods, plantings and friendly faces. Explore Jones Farm for local meats and ice cream. Event space for special occasions, pumpkin patch and seasonal surprises. Convenient Sassy Market for deli, fresh meat and the perfect snacks and beverages. Galena has fine and casual dining, p

Welcome to this spacious Cape Cod situated on a generous corner lot in Centreville's Hunters Ridge neighborhood. Offering four bedrooms, two full and two half baths, and multiple living spaces, this home provides a flexible layout with plenty of room to gather, entertain, work from home, or spread out. The main level features a primary bedroom, along with formal living and dining rooms and a kitchen that flows into the family room for comfortable everyday living. A cozy wood stove adds warmth and character, while the sunroom provides another inviting space to relax and enjoy views of the backyard. Upstairs, you'll find two additional bedrooms, while the fourth bedroom is located above the garage with its own half bath. This separate space offers plenty of versatility and could work beautifully as a private guest area, home office, hobby room, or bonus space depending on your needs. Outside, the deck overlooks the spacious backyard, offering plenty of room to relax, entertain, or enjoy