Chestertown MD Real Estate & Homes for Sale

Where Shore living begins! This well maintained home is established within the quiet subdivision of Kingstowne Manor. Located just on the Queen Anne's County side of the Chester River Bridge, this location offers opportunities from both Kent and Queen Anne's Counties. Just minutes from the heart of Historic Chestertown where you'll find plenty to discover through the Local Shops & Restaurants, weekly Farmers Market, Parks for Recreation and many Events throughout the year. You can fly your flag proudly as you pull into 201 Princess Anne. The asphalt drive will provide a smooth transition home and offer you plenty of area for parking. Bring your boat for quick access to the serene Chester River. By either remote or mobile app, you can open the overhead door to access this homes attached garage. It will provide 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. Stepping inside, the home offers over 2,000 square feet with 3 bedrooms, 2 baths and is established on over 3/4 of an acre. This spacious kitchen provides under cabinet lightening, beautifully crafted seamless quartz countertops and conveys all kitchen appliances. The Living Room and Primary Bedroom both provide options for electric baseboard heat. New carpeting in Primary was installed April of 2024. Stepping outside, you'll be offered plenty of backyard seating and privacy from mature surrounding trees. Relax from your day underneath the recently installed gazebo. The patio here will provide ample space for grilling and gathering. Fenced in back yard provides a worry free option to allow your children (four legged or two) to play freely. A new roof system was installed April of 2024. This system has a transferable 10 year warranty! Home is equipped with top of the line Fiber Optic Internet services. The Septic System has been updated with an additional 80' drain field to support any of your in home services.

Charming Renovated Ranch Home in Tolchester Estates Welcome to this beautifully renovated ranch home nestled in Tolchester Estates. Recently updated, this home offers a perfect blend of modern amenities and tranquil surroundings. As you step inside, you'll notice the new flooring throughout and fresh paint that creates a bright and inviting atmosphere. The remodeled kitchen is a chef's delight, featuring brand new cabinets, elegant granite countertops, and sparkling stainless steel appliances. The spacious master bedroom boasts an en suite bathroom, providing a private retreat within your own home. Both bathrooms have been tastefully updated with contemporary fixtures and finishes. Additional recent upgrades include a new roof, ensuring peace of mind for years to come, and a new heater and air conditioner for ultimate comfort throughout the seasons. Situated in a secluded setting, this property offers privacy, perfect for relaxation and enjoying the natural surroundings. Its proximity to the water adds to the appeal, making it ideal for water enthusiasts or those seeking a serene coastal lifestyle. Don't miss out on the opportunity to make this renovated ranch home yours. Schedule a showing today and envision yourself living in this peaceful retreat in Tolchester Estates.

Beautifully maintained home tucked away on a quiet cul-de-sac but still within walking distance to downtown shops, restaurants, and riverfront. Open floor plan with 9ft ceilings in the living room. 3 bedrooms and 2 full bath with a 2 car attached garage. Covered front porch, secluded screened-in rear porch. Nicely landscaped. Schedule your personal tour!

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? SPECIAL FINANCING options with discounted interest rates, low monthly payments, and low-down payment options make this dream a reality! 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.

Looking for extra space? This home has a large extra room that could be a primary bedroom & bath with walk in closet, a den/playroom, office with a separate private entrance, gym or whatever your lifestyle is in need of! The original primary bedroom includes an attached half bath and the original hardwood floors gleam throughout most of the home! Easy access to multiple public ramps & just a short drive to Downtown Chestertown, this .55 acre home is ready for you to make it your own! *Current HVAC needs refrigerant, a Bryant 15 seer 3 ton AC is estimated to be $9,000! Credit for cost to replace or a reduction in price can be neogtiated*

Investor Alert! A rare opportunity to own a piece of History in down town Chestertown! This home has been a very lucrative rental for the past 10 years which you can easily add to your portfolio or rennovate and bring it back to its glory! One of the few homes on High Street to come with off street parking (up to 4 spaces) accessed by alley way in back. Partially fenced in back yard with privacy and open sunny deck. Nice covered front porch. Inside is boasting with original charm! Original wood floors throughout most rooms. A large eat in kitchen with breakfast nook , overlooking private back yard. Original Sash windows, cedar shingles, and metal roof. Lead Paint Certification. This home has so much potential!

This beautiful custom home on an acre of land has 4 Beds and 2.5 baths. There is an eat-in-Kitchen with granite countertops that is completed by the Maple Wood Island, Gas cooking, and stainless steel appliances, soft close cabinets and 2 pantry's. This home has a Large living and Dining room too! The 'Florida Sunroom' allows could be an office or a place to read a book in the sunshine and the double doors lead out to your fenced in yard. Acacia hardwood floors throughout! This home boasts a new water treatment system (owned) and gutter guard system so you don't have to worry about all the trees that make this home your private oasis in the woods. Upstairs the primary bedroom has a beautiful ensuite bath with separate jetted tub, shower and a double vanity. It also has walk in closest with a window as well as an additional large closet. There is a dedicated laundry room upstairs, ample closet space and 3 other bedrooms that share an updated bathroom. Don't forget the garage and storage room with 2 decks outside! Schedule your showing today!

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 chefâs 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, youâll 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 communityâs 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. Donât 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. 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!

Well maintained Cape Cod in the sought after Coventry Farms subdivision in Chestertown - 1st Floor Master Bedroom includes a spacious walk in closet and a large Full Bath with Walk in Shower â 4 bedrooms, 2.5 baths, a spacious living room, and a large kitchen makes this home irresistible â Be sure to step outside from the dining room through the sliding glass door into the large screened-in deck - Perfect for outdoor entertaining or sitting comfortably and enjoying the secluded backyard greenery.

Construction will be done in 3 weeks, but come see it TODAY! Just over 1500 sq' - Three (3) bedrooms and Two and a half (2.5) baths. It boasts water views of the Chester River and an open-concept layout. The kitchen has stainless steel appliances, and the main-level master suite has 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.

Welcome to a captivating opportunity to reside in the idyllic neighborhood of The Grove in picturesque Queen Anne's County. Prepare to be enchanted by this charming abode, where every detail exudes warmth and comfort. Step inside and be greeted by the timeless elegance of hardwood floors and plush carpeting, inviting you to kick off your shoes and make yourself at home. The heart of the main floor boasts a cozy gas fireplace, creating a cozy ambiance perfect for intimate gatherings or quiet evenings curled up with a good book. With four bedrooms and 2.5 baths, there's ample space for your family to spread out and relax. The open floor plan seamlessly connects the living spaces, allowing for effortless flow and easy entertaining. The kitchen, a culinary haven, beckons with its modern amenities and ample counter space, inspiring culinary creativity and culinary delights. Recent updates abound in this haven of comfort and style, including new skylights that bathe the interiors in natural light, and a spacious deck where you can savor morning coffee or evening cocktails while overlooking your fenced backyard and the serene vistas of rolling farmlands. Venture downstairs to discover a sprawling recreation room, offering endless possibilities for entertainment and relaxation. Whether you envision a home theater, a game room, or a fitness area, this versatile space is ready to fulfill your every need. A separate office provides a quiet retreat for work or study, while an additional bedroom offers flexibility for guests or extended family. Storage woes are a thing of the past, with plenty of space to stow away your belongings or unleash your creativity to reimagine the possibilities of each room. Embrace the quintessential charm of country living while still enjoying the convenience of modern amenities. The Grove offers a tranquil escape from the hustle and bustle of city life, with its tree-lined streets and sense of community. Don't miss your chance to make this enchanting retreat your own. Schedule a viewing today and embark on a journey to a life of comfort, convenience, and timeless elegance in The Grove.

Step inside this stately brick colonial to see and feel the quality of this stunning renovation in Chestertown's vibrant historic district! From the five piece luxury bath in the owner's suite, to the full guest apartment on the third floor, no detail was overlooked. A beautiful view of the meticulous campus green at Washington College invites a walk to downtown, and provides a front row seat to college activities and events like the National Music Festival. A desirable rear alley, leads to the home's private off-street parking spaces and the carriage-styled garage, which can accommodate an SUV. Located on the first floor off the center hall,Âis the living room, dining room, kitchen, den/office, half bath, all- season sun room, and inside stairs to the full high ceilinged basement (which also has an outside entry door.) The new custom kitchen showcases an individually handcrafted brick floor, imported Spanish tiled backsplash, and gourmet appliances and fixtures. Wrap around natural lighting, open shelving, oversized island and walk in-pantry make this kitchen one of a kind, and completes the first floor. The second floor begins with the original grand stairway and a cozy sitting area in the window nook at the end of the catwalk. The primary bedroom comes with a five piece luxury en-suite bath, while two additional bedrooms share a full bathroom off the landing. The dedicated laundry room, also on the second floor, has storage cabinets, room for ironing and folding and a cleaning supply niche. The third floor garret-studio apartment completes the living areas inside this home. This spacious studio has a full bathroom, dedicated cooking & eating area and independent climate control. A comfortable sitting area and separate sleeping space, and separate desk space round out this studio. There is also a Âfull basement of approximately 1100 square ft with both interior access and a highly coveted exterior access. 7.5 foot high basement ceilings, provide an excellent opportunity to design an additional apartment, fitness studio, family room, wood shop etc. Exterior and mechanical upgrades include: a new roof, gutters & downspouts, a new front landing with oversized walkways and raised brick landscape beds. Significant wiring upgrades include a new electrical service and wiring for new electrical components. Plumbing upgrades include a new main shut off valve and a new water line between the house and street. Replacement of most of the interior plumbing was done to accommodate updated fixtures. The one-car, carriage styled garage has been placed for optimum versatility. It makes a charming extension of the outdoor entertaining space to effortlessly plan for changeable Chesapeake-country weather. Simply move the car, open the barn doors, turn on the the oversized crystal chandelier and the tone is set for gatherings protected from the elements! With the double barn doors opened, Âthe terraced courtyard can be incorporated into any event. This property is fully fenced & gated providing privacy for outdoor activities and security for family pets. This brick center-hall colonial Âhas been extensively renovated and is turn-key! Square footage is estimated: buyer to verify. A complete upgrade record is available upon request. Talk to your agent about possible owner financing on this home.

Welcome home to this stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. This exquisite three-bedroom, two-and-a-half-bath home offers luxurious living and breathtaking views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious, open floorplan layout provides ample room for relaxation and entertaining. With high-end finishes including granite countertops, luxury vinyl and tile flooring, Hardie plank siding, stainless steel appliances, etc. and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Welcome home to this stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. This exquisite three-bedroom, two-and-a-half-bath home offers luxurious living and breathtaking views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious, open floorplan layout provides ample room for relaxation and entertaining. With high-end finishes including granite countertops, luxury vinyl and tile flooring, Hardie plank siding, stainless steel appliances, etc. and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Welcome home to this stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. This exquisite three-bedroom, two-and-a-half-bath home offers luxurious living and breathtaking views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious, open floorplan layout provides ample room for relaxation and entertaining. With high-end finishes including granite countertops, luxury vinyl and tile flooring, Hardie plank siding, stainless steel appliances, etc. and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Welcome home to this stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. This exquisite three-bedroom, two-and-a-half-bath home offers luxurious living and breathtaking views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious, open floorplan layout provides ample room for relaxation and entertaining. With high-end finishes including granite countertops, luxury vinyl and tile flooring, Hardie plank siding, stainless steel appliances, etc. and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

This circa 2011, white brick house was built to celebrate the expansive views over the Chester River Yacht &Country Club golf course to the Chester River. There is an attractive patio at one end and a screened porch off the owner's suite. The landscaping around the circular driveway is lovely; the garage is set on an angle as to be unobtrusive from the road and the house entrance. Inside, all the rooms enjoy the views; the glassed in sun room being the most spectacular. Beautiful flooring, oversize crown molding, chair rails, accent & recessed lighting and painted paneling throughout. New A/C handler, Rinnai system with boosters (to reach around this 4,000+ sq. ft. house), foam insulation underground and up the walls, crawl space encapsulated, 3 temperature zones and audio wired surround sound. The kitchen and owner's suite are too great to try to describe, for instance, the marble came directly from Italy and no longer available. Laundry and "mud kitchen" are between the owner's suite and garage. Take a golf cart to the club, ride a bike into town or just sit and watch the tall ships go by.

Wonderful renovation, modern, efficient, and move in ready! Home features vaulted ceilings with open flexible floorplan and 2 brand new luxury bathrooms. Energy efficient instant hot water heater. Large side deck, plenty of parking, small storage shed, and updated BAT system septic. Spacious yard for a garden and family events. Can't pass up this AFFORDABLE price point for like new construction, but not a townhouse!

Rare opportunity in a great residential location. Spacious, situated on a half acre triangular lot. Check out the many possibilities for this property. Great investor opportunity in a beautiful neighborhood. Zoned residential, buyer to confirm all plans with Kent County Planning & Zoning. Residential home must be built to obtain town water/ sewer.

A stately 1800âs waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own ground level storage. This is a unique setting offering waterfront living in downtown historic Chestertown and includes off street parking. Walk to downtown restaurants and shops. Beautiful southeast views of the Chester River with spectacular sunrises and plenty of year-round sunshine. Take in the all of the nearly year-round waterfront activities from your own back yard, including Chestertown Tea Party, 4th of July fireworks and Sultana down rigging weekend. Located on Marylandâs scenic eastern shore less than 85 miles from Washington DC to the south or Philadelphia to the north, this home is the perfect meeting spot for those living in the Mid-Atlantic region. This unit offers a 1 Bed 1 bath has a brand new kitchen, with island, and upgraded bathroom along with up and down river views.

A stately 1800âs waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own ground level storage. This is a unique setting offering waterfront living in downtown historic Chestertown and includes off street parking. Walk to downtown restaurants and shops. Beautiful southeast views of the Chester River with spectacular sunrises and plenty of year-round sunshine. Take in the all of the nearly year-round waterfront activities from your own back yard, including Chestertown Tea Party, 4th of July fireworks and Sultana down rigging weekend. Located on Marylandâs scenic eastern shore less than 85 miles from Washington DC to the south or Philadelphia to the north, this home is the perfect meeting spot for those living in the Mid-Atlantic region. This unit offers a 2 Bed 1 bath has a brand new kitchen, with island and upgraded bathroom along with up and down river views. Now with one slip available for purchase

A stately 1800âs waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own ground level storage. This is a unique setting offering waterfront living in downtown historic Chestertown and includes off street parking. Walk to downtown restaurants and shops. Beautiful southeast views of the Chester River with spectacular sunrises and plenty of year-round sunshine. Take in the all of the nearly year-round waterfront activities from your own back yard, including Chestertown Tea Party, 4th of July fireworks and Sultana down rigging weekend. Located on Marylandâs scenic eastern shore less than 85 miles from Washington DC to the south or Philadelphia to the north, this home is the perfect meeting spot for those living in the Mid-Atlantic region. This unit offers a 1 Bed 1 bath has a brand new kitchen, with island, and upgraded bathroom along with up and down river views.

Beautifully renovated waterfront on the Chester River, located between historic downtown Chestertown and the Chester River Yacht and Country Club. Renovations include including new kitchen and bathrooms. This property boasts a deep water dock with lift for your boating, swimming and fishing pleasures. Come and enjoy all the Chestertown has to offer with just a short walk to down town shops, restaurants and parks..

Every so often a property like 240 Round Top Landing Road, Chestertown hits the market that checks all the boxes. This Chester River waterfront estate is situated on 10 acres , offering deep water, pier, 25' x 50 ' in-ground pool, screened porch , 3 bedroom/3.5 bath main house and a carriage house. The architectural design and the superb craftsmanship are evident as soon as you enter the driveway. Beautiful trees(Peach,Pear, Pines, Poplars, Sycamores, Magnolias' Crepe Myrtles) enhance the park-like setting. Notable features are geo-thermal heat; gas and wood burning fireplaces, chef's kitchen; first floor spacious primary bedroom suite , and open living areas. As far as the exterior, the stucco siding is either over brick or block so no stucco is over frame. Some poplar siding on main house and cedar siding on carriage house.