Chestertown MD Real Estate & Homes for Sale

Discover your dream home perched on a tranquil hill in Chestertown, Maryland. This beautiful 3-bedroom, 2.5-bathroom residence features lush landscaping and a welcoming front porch, ideal for enjoying scenic views. Inside, the open floor plan is filled with natural light, showcasing a spacious living room with a cozy fireplace and a gourmet kitchen that's perfect for entertaining. The master suite offers luxury with an en-suite bathroom and walk-in closet, along with two additional bedrooms for guests or flexibility. Step outside to an expansive backyard, perfect for outdoor gatherings while taking in picturesque surroundings. This home is located in a family-friendly neighborhood with easy access to parks, shops, and dining, making it a perfect blend of suburban charm. Schedule your private showing today and experience the beauty and comfort of 126 Hilltop Drive - your future home awaits!

Coastal waterfront condo with excellent views in prestigious Chester River Landing offering amenities including a private marina, community pool, fire pit, gas grills, and kayak launch. This turn-key unit with expansive, breathtaking views of the Chester River offers a deeded deep water boat slip, 2-car garage, 2 covered balconies, and upgraded throughout! Make the most of Downrigging weekend this year by enjoying the festival's fleet of Tall Ships from your very own home. A mere 3/4 mile away is Chestertown's historic downtown, host to our local speakeasy, nationally recognized farmers' & artisans' market, fine dining, walking/jogging path, eclectic shops, a plethora of activities and events throughout the year, and so much more. Summer is just around the corner and there is no better place to be than here on The Chester.

Welcome to 116 Pine Chip Road, a beautifully renovated Cape Cod in the heart of Chestertown, MD, Queen Anne's County. This 3-bedroom, 1 1/2-bathroom home has undergone a complete transformation, boasting new siding, windows, doors, and drywall throughout. The modern upgrades continue inside, where you'll find stunning LVP flooring on all three levels. The main level features two spacious bedrooms, each with double closets, and a full bathroom. The custom kitchen is a chef's dream, featuring a gas stove, upgraded quartz countertops, solid wood cabinets, and stylish open shelving. Upstairs, the primary bedroom offers a private retreat with a mini-split AC/heat unit, a large dressing room, and a convenient 1/2 bath. The finished basement is perfect for entertaining, complete with surround sound, a laundry room, and a utility room. The outdoor space is equally impressive, with a newly installed privacy fence surrounding the backyard. The fence includes three personal gates and one large gate for vehicle access. Additionally, the property features a shed and a detached garage, providing ample storage and workspace. This home is move-in ready and offers a perfect blend of modern amenities and classic charm. Don't miss the opportunity to make 116 Pine Chip Road your new home!

Very affordable with a nice .59 acre lot. A great Re-Hab opportunity. Nicely located Rancher in Chesapeake Landing. Voluntary HOA membership allows access to Worton Creek. Property Backs up to Community Recreational Area with a pond. This is an opportunity to design your new home.

Step into your dream home just outside of Downtown Chestertown, recently updated with new flooring, fresh paint, and professional cleaning! This inviting residence offers beautiful views of a spacious community open space'perfect for dog walking and outdoor play. The large unfinished basement, filled with natural light from the egress window, provides an ideal space for activities or ample storage options. Above the garage, a generous family room awaits'flexible enough to serve as a bedroom, playroom, exercise space, or whatever fits your needs! Retreat to the primary bedroom featuring two closets, including a walk-in, and an ensuite bath designed for relaxation with a soaking tub and separate shower. Experience comfort, convenience, and community in this updated home. Don't miss your chance to make it your own!

Welcome to 1316 Ewingtown Rd, where the charm of historic Chestertown meets the tranquility of rural living. Nestled on nearly 3 '½ acres of pristine land (main lot is 2.33 acres and adjacent lot is 1 acre), this Art Deco Farmhouse is a private retreat surrounded by thousands of acres of preserved farmland and woodlands. Just 45 minutes from Annapolis and Easton, and a quick 10-minute drive to Washington College and the vibrant, waterfront town of Chestertown, this property offers the perfect balance of seclusion and convenience. Step inside this custom-built home and be greeted by 2,476 square feet of thoughtfully designed living space. The main level features an inviting living room, a gourmet kitchen complete with a peninsula for casual dining or meal prep, and a dining area warmed by a wood stove'ideal for unwinding after a long day. The screened porch opens to the home with its fold out glass doors and bathes the home in natural light, and offers breathtaking views of the expansive yard, making it a year-round haven. The primary suite, conveniently located on the main level, is a serene retreat with its own private porch and an outdoor hot tub, perfect for relaxation. Upstairs, you'll find three generously sized bedrooms and a full bath, ensuring ample space for family or guests. But the charm doesn't stop there. Just steps from the main house is "The Ponderosa," a workshop/party barn that offers endless possibilities and an additional 1300 square feet of space. Whether you dream of running a home-based business, need a space for creative projects, or want to host gatherings, this versatile structure is equipped with a bar, wood stove, and plenty of storage. With room for a pool, chickens, or even fainting goats, the possibilities for this property are as vast as the landscape that surrounds it. Chestertown itself is a gem, offering a delightful blend of history and modern amenities. Explore the historic district with its charming shops and restaurants, visit the renowned farmers market, or take part in the town's annual festivals that celebrate the area's rich heritage. For outdoor enthusiasts, the nearby Chester River offers opportunities for boating and fishing, while the town's vibrant arts scene and close-knit community provide a warm welcome to newcomers. Whether you're seeking a peaceful retreat, a place to grow your own garden, or the perfect spot to run a home business, 1316 Ewingtown Rd offers it all. Don't miss the chance to make this unique property your own slice of paradise. * Sale to include the adjacent lot with Street Address: 101 1st Street Chestertown, MD 21620. Buyer to pay transfer taxes on assessed value of lot. Lot is non-buildable.

Welcome to your dream home in the charming sought after community of Chester Harbor! This delightful property boasts 3 spacious bedrooms and 2 full updated bathrooms, perfectly designed for comfort and modern living. Step into the huge master bedroom, perfect for all buyers. The finished basement provides versatile additional living space'ideal for a family room, home office, or play area. The recently renovated kitchen is a culinary enthusiast's dream, featuring contemporary finishes and high-end appliances that make meal prep a pleasure. Outside, the great yard is perfect for entertaining, gardening, or simply enjoying the serene surroundings. Enjoy the HUGE garage located in the rear of the property. Chester Harbor Community has a voluntary HOA ($30/year), which offers water access, a beach, community events, and a playground. Just around the corner is Round Top Park offering tennis, pickleball, and basket ball courts, a playground, and pavilion. Minutes from Chestertown's historic waterfront, restaurants, shopping, and marinas

Conveniently located between Church Hill and Chestertown this home sits on a quiet cul de sac with 1.25 acre lot backing to farm fields. Fenced rear yard is great for 2 or 4 legged family members and provides ample room to play, garden, or just relax. Inside features over 1400 SQFT of finished space with 3 bedrooms, 2.5 bathrooms and great lower level family room with walk out to rear yard and garage, plus cozy electric fireplace in the living room. Hardwood floors, granite counter tops, and stainless steel appliances. Enjoy quiet evenings on the upper level deck overlooking back yard. Just a hop skip and jump from historic Chestertown, for shopping, farmer's market, and local points of interest. Rt 213 south takes you to Church Hill and the beautiful County Park and State Wildlife management area, or keep driving and you are just minutes from Centreville. Boat ramps and Chester River fishing close by. Come check it out. You will not be disappointed. OPEN HOUSE SAT 10 - 12 NOON.

Welcome to this delightful brick rancher, offering over 1500 square feet of living space. This home features 3 spacious bedrooms and 2 full baths, perfect for accommodating a variety of lifestyles. The living room showcases a beautiful brick fireplace enhancing the open floor plan's charm and creating a warm and welcoming focal point. Country kitchen with island, separate pantry and tons of storage makes meal preparation a breeze. At the back of the house, the primary suite serves as a private retreat with an ensuite that has a recently updated shower. The original hardwood floors, elegant and timeless, flow throughout the home, adding warmth and character to every room. Newer windows and encapsulated crawl space enhance energy efficiency and fill the home with abundance of natural light. An separate mud room/laundry area and attached one-car drive-thru garage offers convenience and functionality, with added versatility perfect for busy families and car enthusiasts alike. Additionally, the separate workshop shed, 18x22, includes a garage door and is ideal for hobbyists. Outside you will find a relaxing patio and mature plantings that create a tranquil escape to unwind in after a long day. The lot backs to farmland, offering unmatched privacy and scenic views. A 2-car drive pad provides ample parking for you and your guests, ensuring convenience for family gatherings and visitors. A rear enclosed porch with heat is perfect for year-round enjoyment, a versatile space for relaxation. With its serene location, layout, and inviting outdoor spaces, it's the perfect place to create lasting memories. Meticulously maintained - Roof-septic-2009/Crawl space encapsulation-2012/Fireplace serviced 2023/Furnace serviced 2023 A few short miles south or north will take you to downtown Chestertown or Rock Hall, offering walking trails, playgrounds, River fun, specialty shops, exquisite dining, renowned Farmers Markets, nature parks and famous festivals. Don't miss your chance to make this charming brick rancher your own!

RARE AND UNIQUE CUSTOM BUILT CONTEMPORARY on a corner .37acre lot in the highly desirable neighborhood of Mile Tree Village. This gorgeous, meticulously maintained home offers all on one floor living in light-filled, easy care, open floor plan comfort. Features include cathedral and vaulted ceilings in the main living area and master bedroom; handsome light-toned maple flooring throughout the central living area; a glass doored corner gas fireplace in the living room; ample cabinet, pantry, storage and closet space; an oversized attached two car garage; roofed, sitably sized front and side porches; a lovely large rear patio with awning; and a custom-built stone terrace with a waterfall fountain. Additional household amenities are extensive, including like-new stainless kitchen appliances; induction cooktop and double wall ovens; a kitchen prep sink; custom granite and Corian counters in the kitchen and bathrooms, a soaking tub and glass walled walk-in shower in the Primary Bathroom ; hardwired home security and fire alarm and sprinkler systems ; A whole house generator, a surround sound system in the Den; a central vacuum system; multiple phone lines; automatic garage door; invisible fencing for pets, and the list goes on. The house has two sets of solar panels installed on the rear roof: one owned by the Sellers and the other subject to a power purchase agreement with TESLA. Both sets of panels convey with the house. Sellers are billed monthly for power generated by the TESLA owned system and receive approximately $6o/year from SOLSYSTEMS for power generated by the panels they own. Professionally maintained landscaping that includes a variety of lovely mature flowering shrubs, perennials and trees and an in-ground watering system surround the house. A trim lockable garden shed sited in a wooded area at the back of the house provides out of the way storage for lawn mowers and garden equipment and supplies. In addition to its many on-site pluses, this wonderful home offers convenient, quick and easy access to Washington college, area schools, parks, doctors, churches, Historic downtown Chestertown, waterfront recreational facilities and shopping centers. PRICE JUST REDUCED OVER $10K!

First time to ever be offered on the market. Nestled in a picturesque neighborhood, this contemporary home is a testament to luxury and functionality. Spanning over 3,400 square feet, this meticulously maintained home has so much to offer. Spacious Living Areas: Open-concept layout with hard wood floors, high ceilings and abundant natural light, complemented by 2 gas fireplaces for cozy evenings . Gourmet Kitchen: Chef's delight with stainless steel appliances, granite countertops, and ample storage space. Luxurious Bedrooms: Featuring a first-floor primary suite with new carpet (2023), walk-in closet, and a spa-like ensuite bathroom. Additional Features include: Tankless water heater for efficiency, whole house generator for peace of mind, recently renovated garage highlighting ample storage and recently new roof (2 years old) with a 30-year shingle warranty. The stunning backyard offers a true outdoor retreat with curb appeal enhanced by a Japanese maple and meticulously landscaped surroundings. Enjoy a propane-heated concrete pool with a 6-foot deep end and built-in love seat, professionally maintained. The composite deck is ideal for outdoor entertainment and relaxation. Don't miss the chance to own this exceptional home! Contact me today to arrange a private viewing.

Nestled in a prime suburban commercial zone, this versatile property offers 1,300 sq ft of living space, perfect for both residential and/or commercial use. The freshly resealed driveway accommodates up to 6+ vehicles, with the potential for parking lot expansion, ensuring ample space for guests or clients. The property features two inviting front entries: one through an 8x16 sunporch, ideal for enjoying morning coffee or greeting visitors, and another through the welcoming living room with a large bay window that floods the space with natural light. The rear entry provides convenient access to the kitchen and basement. The kitchen is equipped with all essential appliances and features laminate countertops and durable vinyl flooring. A pass-through window connects the kitchen to the sunroom, enhancing the open and airy feel of the building. The basement, with its poured concrete floor and perimeter trench leading to the sump pump, offers potential for additional storage or workspace. The single level structure includes a spacious full bath and three generously sized bedrooms, perfect for a family or for converting into office spaces. This property blends functionality and charm, making it a unique opportunity for those looking to live and work in a suburban setting.

Built in 2005, this like-new home boasts an open floor plan with inviting, bright spaces. The residence features 3 bedrooms, 2.5 bathrooms, and 1,222 square feet of low-maintenance living. Enjoy the convenience of two dedicated parking spots right in front of the home, as well as no outside maintenance. The half bath comes equipped with a stacked washer and dryer for added ease. The spacious living room and dining room seamlessly flow to a sliding door that opens to a rear porch and common grounds, perfect for relaxing or entertaining. Located in Chestertown, this home is in close proximity to Washington College, Chester River Hospital Center, and the Chestertown walking trail, making it an ideal location for both convenience and leisure.

Charming Historic Chestertown investment opportunity! Once updated this building can accommodate two street-front shops and a spacious apartment upstairs. The back of the building has extra living space with a private entrance and full bathroom. The attic is flooded with natural light! One could use the attic as-is for extra storage, or it could be renovated, adding additional living space. Back deck overlooks sweet courtyard, perfect for relaxing. GREAT location and tons of character - enjoy the Chestertown Farmer's Market year round, the Chester River just a few blocks away, shops and restaurants right down the street - you cannot beat this Historic District location and opportunity. Seller has removed plaster walls downstairs and updated the electric. Other updates include: exterior painting, new metal roof and a new deck with entry to second floor apartment.

Welcome to your private oasis! This charming home boasts mature landscaping that provides both beauty and privacy on a large corner lot. . Custom built Cape Cod offers a first floor primary suite, living room with fireplace and built ins, formal dining room and a kitchen with granite counters and updated appliances. There's an open area on the 2nd level ideal for reading or watching TV. Plus 2 more bedrooms and an office. Enjoy the serene ambiance from the large deck, overlooking a picturesque pond with not one, but two enchanting waterfalls. The soothing sound of cascading water creates a tranquil atmosphere, perfect for relaxation and unwinding. This property is a true retreat, offering an idyllic escape right in your backyard. Located just minutes from the Chester River and Chestertown's historic district.

Spec home located in small 12 home development (to be built). Prestwick offers the best in eastern shore living with the small town charm of Chestertown, MD, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington, DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board or kayak at the new town marina or the many county owned ramps. Design and build the home you want with one of the area's finest builders

Park like setting with natural beauty all around you, take a quite day with very nice outdoor den . Watch the herons, eagles, ducks and geese search for food or take a leisurely kayak cruise down Mill Creek to the Chesapeake Bay. Conveniently located a short distance from Worton Creek Marina, Restaurants, Resort Style Marinas, Historic Chestertown, Parks and much more. Chesapeake Landing Offers water access with 2 marinas, boat slips and docks. A perfect location to keep for a weekend away on the beautiful Eastern Shore or primary residence.

Completely remodeled, this three-bedroom waterfront home boasts a charming front porch and enormous back porch - your private space overlooking the river - along with an enclosed sunroom featuring gorgeous river views through walls of windows. Enjoy abundant outdoor areas and stunning water views from nearly every room. The dock features 3+ feel MLW, with slips available for purchase. This condominium embodies the ideal waterfront living experience. Located in the heart of historic Chestertown, this unique property includes off-street parking and provides the convenience of walking into town for dining and shopping. Situated on Maryland's scenic Eastern Shore, it's less than 85 miles from Washington D.C. and Philadelphia, making it a perfect meeting spot for those in the Mid-Atlantic region.

Discover the epitome of luxury living in this exquisite townhome nestled within the prestigious water-oriented community of Chester River Landing. Designed with elegance and comfort in mind, this residence offers an unparalleled lifestyle that combines sophistication with the serene beauty of waterfront community living. The heart of the home, the open kitchen is designed for both functionality and style. It features sleek countertops, ample cabinet space, and a large island that doubles as a breakfast bar, making it perfect for meal preparation and casual dining. Enjoy the convenience and efficiency of top-of-the-line appliances throughout the home, including a stainless steel refrigerator, oven and dishwasher. Open room on first floor could be used for a third bedroom for guests. Enjoy the sunset from the upper deck or below on the screened in porch by the pond with fountain. The porch was renovated this spring with high tech flex screens and ceiling was waterproofed providing for increased time for usage while keeping the area dry. Chester River Landing is nestled along the serene Chester River, this charming waterfront community exudes a perfect blend of relaxation and recreational opportunities. The centerpiece of the community is a picturesque floating pier that gently sways with the rhythm of the water. This well-maintained pier offers numerous available slips, making it an ideal haven for boating enthusiasts who enjoy easy access to their watercraft. Enjoy the community pool during the day then take in the sunset on the pier with picnic tables and a gas grille. As the day transitions into evening, the fire pit area becomes a popular gathering spot. Encircled by cozy adirondack chairs, the fire pit offers a warm and inviting ambiance, perfect for sharing stories, roasting marshmallows, and enjoying the company of neighbors under the starlit sky. All of this while located in the Historic Town of Chestertown, known for its waterfront charm, restaurants, and weekend festivals! Don't miss your chance to make this remarkable property your own!

Welcome home to this 3 BR 2 bath home in Kingstown Manor, situated on 1/2 acre just seconds from the Chester River. Newly refinished flooring throughout! The gorgeous, custom tiled backsplash, updated kitchen includes stainless steel appliances and is open to the dining area with built in bench seating. From the dining area you can exit the rear door onto the patio overlooking the fenced backyard with mature trees. Cased openings separate the kitchen and dining from the living room with adjoining office. Both the primary and hall baths are updated with custom tiled showers. Updates to the home also include roof, septic, HVAC, windows, doors and water softener with reverse osmosis.

Where Shore living begins! Welcome to 201 Princess Anne. Located on the Queen Anne's County side of the Chester River Bridge, this well maintained home is established on just over 3/4 of an acre within the quiet subdivision of Kingstowne Manor. Offering 3 bedrooms and 2 baths, this home also comes equipped with a fully floored attic for all of your storage needs! A new roof system was installed April of 2024. This system has a transferable 10 year warranty! The asphalt driveway will ensure a smooth transition home and offer plenty of area for parking. The attached garage provides ample space to keep your vehicles, toys or projects out of the weather and well protected. Equipped with a propane heater and 220 AMP service, you can comfortably stay busy year round. The spacious kitchen provides under cabinet lightening, beautifully crafted seamless quartz countertops and conveys all kitchen appliances. The Living Room and Primary Bedroom are both generous with the space they provide and new carpeting in Primary was installed April of 2024. All 3 bedrooms have desirably spacious closets with ceiling fans throughout. Stepping outside, you'll find plenty of backyard seating and shade underneath the recently installed gazebo. The patio here will also provide ample space for grilling and gathering. The fenced in back yard offers a worry free option of allowing your children (four legged or two) to play freely. Home is equipped with top of the line Fiber Optic Internet services. The Septic System has also been updated with an additional 80' drain field to support any of your in home services.

Come By this brand new Cape Cod nestled in charming Pear Tree Point! This 3-bedroom, 3-bathroom haven offers the tranquility of coastal living with the ease of new construction. Step inside and discover the warmth of this open floor plan luxury vinyl plank flooring flowing throughout the main level. Unwind in the light-filled living area, perfect for entertaining, or retreat to the inviting main-floor primary bedroom suite, designed for ultimate relaxation. This private sanctuary boasts an attached bathroom with modern fixtures and finishes, and spacious walk-in closets. Unleash your inner chef in the stunning kitchen, featuring stylish shaker cabinets, gleaming granite countertops, and a suite of stainless-steel appliances. Extend your living space onto the expansive patio, perfect for al fresco dining or simply soaking up the tranquility of your waterfront surroundings. Modern finishes throughout and ample storage space completes this lovely home. But the best part? Pear Tree Point offers a vibrant community atmosphere with water access, marinas, and nearby parks. Don't miss this opportunity to own a brand-new waterfront haven! Contact us today to schedule your private showing .****Special Discounted Financing in available for this home, with rates in the low 5's are available**** Contact for details, rates subject to change, subject to loan qualification.

Welcome to 101 Landing Lane, an exquisite residence offering exceptional living in the prestigious Chester River Landing Community. Boasting an expansive 3,300 square feet of meticulously designed living space, this home features luxurious amenities and elegant finishes across three levels, ensuring comfort and style at every turn. Step inside to discover the warmth of hardwood floors that flow seamlessly throughout the home. The main level features a spacious guest bedroom and a full bath, perfect for accommodating visitors with style and ease. A well-appointed study on this level offers a quiet retreat for work or relaxation, ensuring a versatile and functional living space. The lower-level deck is perfect for relaxing with a good book, overlooking the scenic community pond, and the attached one-car garage provides parking and storage space. The second level's open floor plan integrates the kitchen, living room, and dining room, creating an inviting space ideal for modern living and entertaining, with hardwood floors throughout. The gourmet kitchen is a chef's dream, showcasing rich wood cabinets, stone countertops, and stainless steel appliances. The living and dining areas extend effortlessly to an upper-level balcony, perfect for al fresco dining and providing serene views of the community pond. The primary bedroom on this level offers a luxurious sanctuary with a large walk-in closet and beautifully finished bathroom The third level is designed for leisure and entertainment. Here, you'll find an additional bedroom and a versatile game room, perfect for family fun or casual get-togethers. The game room can be adapted to suit your lifestyle needs, whether as a media room, playroom, or hobby space. Residents enjoy easy water access and exclusive use of the community's private dock and swimming pool. The swimming pool offers a refreshing escape during the warmer months, perfect for relaxation and recreation. Experience the epitome of elegant living in a vibrant and friendly community in this move-in ready home. Don't miss the opportunity to make 101 Landing Lane yours. Schedule a private tour today and discover all the exceptional features this property has to offer.

Looking for something truly special? Don't miss this unique offering, located in the vibrant heart of Chestertown's Historic and Arts & Entertainment Districts! Boasting a legacy of over half a century under the stewardship of one devoted family, this multi-family property presents a rare opportunity for visionary investors and passionate renovators alike. Situated on a generous lot, steeped in the rich history of Chestertown and prominently featured on historic maps as the Laurence Lots, this property offers a canvas brimming with potential. Whether you envision revitalizing it into a majestic single-family residence or retaining its current configuration with a townhouse on one side and two apartments on the other, the possibilities are boundless. While the property stands as a testament to enduring charm and character, it's essential to note that significant settling has occurred over the years. As such, unlocking its full potential will necessitate considerable renovation efforts. This property is a bona fide fixer-upper and is exclusively offered in its current "as is" condition, awaiting the transformative touch of its next custodian. With its prime location , this property represents not only an investment opportunity but a chance to become part of Chestertown's storied legacy. Located squarely in the Arts & Entertainment District and Enterprise Zone, both residential and commercial uses are permitted. Seize the chance to breathe new life into this home and craft a future brimming with possibility. Embrace the challenge, unleash your creativity, and make your mark on Chestertown's captivating tapestry of history and culture. Schedule your viewing today and prepare to embark on an unforgettable journey of restoration and renewal!

Come see it TODAY! Just over 1500 sq' - Three (3) bedrooms and Two and a half (2.5) baths. Water views of the Chester River and an open-concept layout. Stainless steel appliances in the kitchen, a main-level master suite with a walk-in closet and ensuite. Upstairs, you'll find two more generously sized bedrooms and an additional full bathroom. High speed internet is available. The home is located at the end of a quiet, private street. Queen Anne's County Impact Fees have been paid by the Seller.