Chestertown MD Real Estate & Homes for Sale

This Colonial has had a kitchen update 4+/- years ago with granite counters, breakfast bar and a propane gas stove and lots of cabinets. The main floor bath was updated 3+/- years ago with handicap toilet and walk-in shower. Having a main floor bedroom is a huge plus! Most of the main level has bamboo flooring installed. There are 3 additional bedrooms on the second floor, two of which are quite large. The interior has been freshly repainted. All screens have been replaced. A rear deck a with ramp and patio overlook a fenced backyard and there is outdoor lighting! There is even electric hookup for your motor home. Add the fact that Chesapeake Landing has community water access, then what else could you ask for?

Not your average floor plan. This home features three levels, with a family/play/game room downstairs, two options of storage or make one an exercise area! The main level has a study/bar area just to the left of the front door, and a formal dining room on the right, with a two-story foyer that leads back to the great room and a beautiful kitchen. Featured in the kitchen is a breakfast bar area, an island, a coffee "station" and loads of storage. The great room has nice light coming in from the windows overlooking a barbecue deck, a patio area, and the back yard is fenced in for your four-legged friends! Still more to come on the main level though! There is a breakfast area with plenty of room for a large table and /or cabinets and breakfront style furniture. Down the hallways is the powder room, which is generous in size, a large laundry/storage room, and an office for those of us who LOVE to work from home. The hallway door leads to the two-car garage. Upstairs is a beautiful owner suite and owner bathroom that has everything you need or could want, also featured is a large walk-in closet. Three other nice sized bedrooms and an overlook into the foyer completes the upstairs level. Don't miss it! Unique home with loads of space! The patio and deck were added in 2021, and new flooring on the main floor was installed October 2020. They used ThinkBig for internet (which is fiber)

A kodak moment! Picture yourself and your family in this spotless 4 BR, 2.5 BA Colonial on a quiet street in Chesapeake Landing within walking distance of Worton Creek and the marina. With hardwood floors, eat-in kitchen, covered front porch, fully fenced back yard, attached 1 car garage and a lot more. Voluntary Community Association with water privileges! All you need now is a kayak and/or paddle board!

Welcome to one of the largest homes in Coventry Farms Section II. Featuring three floors of spacious living area, there is plenty of room for work, play, and relaxed community living. Yet... Nature is just a few steps from this lovely home. This is the most unusual lot in the community and backs to the woods and if you love nature--you must see this home! One of the grandest features of this home is the bright and airy sunroom, which gives a prominent view of the woods, giving you a front-row seat to enjoy watching nature up close. If you paint or enjoy wildlife photography, this is the perfect studio to perfect your craft. Home backs to woods and also adjoins an overgrown former horse pasture that allows deer and turkeys to safely feed in daylight hours. Deer and turkeys regularly come into this yard and also feed along the property rear going to feed in the field across the road and on their return in the morning to bed in the deep woods behind this home. The owners have had flocks of turkeys, mother turkeys and their young polts(babies), and herds of deer(including some nice bucks) visit this yard. And foxes, squirrels, rabbits, robins, bluejays, cardinals, and many other birds also visit frequently. Bald eagles, ospreys, owls, and hawks fly over the woods and pasture. The large master suite is really grand, with a lit tray ceiling and ceiling fan, an oversized bathroom with a shower, and also a separate jetted tub for relaxing. From the master bedroom, one can also enjoy a grandstand view of the pasture behind and wildlife coming and going. Two walk-in closets complete this spacious oasis. First-floor features include beautiful hardwood floors, granite counters, two-story entry foyer, and a gourmet kitchen with stainless steel appliances(refrigerator replaced in 2021 and dishwasher in 2022). If you work from home, the first-floor office offers plenty of ambient light and space for the largest desk. The basement has lots of natural light with a set of French doors and a wide external staircase for moving furniture in and out. The 5th large bedroom in the back is super spacious and could be a pool room, office, or bedroom(prior to closing an exit window will be installed by the seller). There is an unfinished room with an exit window and insulation that could be finished for a 6th bedroom, office, or a recording/social media studio. There is plenty of interior storage that could also be finished or converted into cedar closets or workshop space. The refrigerator was replaced in 2021, the dishwasher was replaced in 2022, and the first floor/basement air handler was also replaced in 2022. The owner is a licensed real estate salesperson.

Just in time for Summer! This cottage is located a stones throw away from the Chester River and public landing - Deep Landing. Fun in the sun awaits you in this 400 sqft cottage. Tucked within the trees that provide a shady location, this is a true one room cottage with kitchen and bath. The main room is a multipurpose room for dining, living and sleeping. Pull down stairs to the attic space also have been used for an additional sleep area by the current owner, however no fix stairs in place and the roof pitch would only accommodate the small in stature as the head room is limited. The space works well for additional storage. The patio area on the rear of the cottage is covered with the same pitch roof, perhaps you may consider enclosing if allowed to give more living space. Lot is .29 acres and seller is selling an adjoining lot .36 acres on the corner of Hoffman and Deep Landing for an additional fee. Live in the cottage as you build on the lot next door. Cottage would made a great vacation rental with just a few improvements or a place to park your boat or RV. Ask about the contents of the cottage....all must go and seller willing to negotiate. Older well and septic in place. County record are limited. Replacement may be needed, contact the county for more information. Selling AS IS.

Brick home was originally built by a local contractor to serve as his primary residence. In recent years the present owner has made renovations to include new tilt wash windows, wood floor refinishing, new master bath with a large tiled double-head shower stall, soaking tub and blue tooth outlet. The kitchen is quite large offering spacious granite countertop work space including an island, built-in wooden shelves matching cabinetry and a built-in charcoal grille encased within an arched kitchen brick wall along with the new double oven. Living room offers a wood-burning fireplace. The home has a great front porch as well as a rear screened porch that accesses out onto a patio of the rear yard that is bordered with trees offering privacy. Since recent home renovation, the owners have used an original family room as a bedroom however could be used as an office with the room having an exterior door.

Beautiful and quiet setting. Lots of grass, fields, privacy and all the natural life Eastern Shore has to offer. Don't miss this opportunity to own this unique 4 bedroom, 2 bathroom home with over 2,600 sqft. of living space that sits on 4.5 acres of land. The home features a central vacuum system, a whole house generator, attached 3 car garage with hydraulic auto lift and oil pit. Paved driveway with plenty of space for parking. This property has endless opportunities! Minutes from downtown Chestertown. Close to local waterfront dining, entertaining, parks and schools.

Tremendous price improvement! Only a few minutes drive to Deep Landing boat ramp on the Chester River, this lovely location nestled among the trees provides a wonderful backdrop for your new home. Just finished, this total renovation contains great room sizes and a floor plan that is smart and functional.

Nestled on a little over 2 acres, this charming home has had many wonderful updates throughout! The large, screened-in front porch will be the perfect spot to entertain guests or drink your first cup of coffee each morning. The main level of the home is bright & airy, and features a living room, full bathroom with shower, laundry/mud room, bedroom and gorgeous kitchen. The kitchen updates include modern cabinetry, upgraded stone countertops, stainless steel appliances and large island. The primary suite is just up the stairs, and has a cathedral ceiling, office area (or maybe your new walk-in closet!), and stunning bathroom. Also located on the 2nd level is a fully updated hallway bathroom and additional bedroom. The top floor features a large bonus space, just waiting for you to design for your family room, craft/hobby room, or office. The Chestertown area feels tucked away from it all, with beautiful farm and forest views along with your commute home. Looking for a delicious meal or sweet treat? Consider visiting Get the Scoop for a sundae, Watermanâs Crab House for your crab fix, Java Rock for a coffee, or maybe enjoy the outdoor dining at Harbor Shack. There are plenty of marinas nearby if you are an avid boater, or maybe take classes at the Delmarva Sailing School if it is a hobby you have been wanting to get into! Sale is As- IS seller will not make repairs but is willing to offer a credit for roof repair!

Just listed on Coventry!! Move in ready home! On the main level, there are formal living and dining rooms and a kitchen that is adjacent to a beautiful breakfast room. You will enjoy lots of light streaming into the first floor. The kitchen has loads of storage with pantry and lots of upper and lower cabinets. The dining room offers a tray ceiling, and plenty of room for your dining room furniture. Upper level boasts of 4 large bedrooms and two full size bathrooms. The backyard has a freshly painted fence, and lots of room for your furry friends. The house has freshly painted exteriors and is nicely landscaped. The basement is large and a clean slate, that you can certainly finish. The two car garage has lots of space for storage. The home overlooks the main park and is centrally located.

Adorable and Affordable - c1934, this cottage is walking distance to the water, restaurants, parks, shopping, live theatre, art galleries, and the everything else Chestertown has to offer! 3 bedrooms, 1 bathroom, original built-ins, wood-burning fireplace, hardwood flooring throughout the 1st and 2nd floors, and large unfinished basement.

WOW! THIS HOME HAS SPACE FOR EVERYONE! It features over 5000 sf of living space, with a guest bedroom and a bathroom on the first floor, and on the second floor is an extraordinary primary bedroom suite that has a walk in closet, sitting area, and an impressive bath. Plus, there are 4 more bedrooms with 2 full baths. The full walkout basement has over 2000 sf of unfinished space. There are tons of possibilities here, and all on 1.25 acres on a quiet cul de sac about 4 miles outside of Chestertown, in Queen Anne's County.

Spacious rancher on nearly 5 acres. 3 bedrooms and 3 full baths. 2 of the bedrooms have en suite baths. Open floor plan with great kitchen. Vaulted ceilings in the living room. Large laundry room off the kitchen with washer, dryer, utility sink and pantry. Den with vaulted ceilings could be used as a 4th bedroom or craft room. Partially finished basement with another room that could also be used as an additional bedroom or hobby room. Large unfinished area in basement with plenty of room for storage and has an additional washer and dryer. Screened in porch off the kitchen and owner's suite. Small green house for the aspiring gardener. Lovely view of the surrounding farmland. Peaceful country living but less than 10 minutes to Chestertown. Interior pictures coming soon!

Affordable investment opportunity in Downtown Chestertown! Great layout with large room sizes, hardwood floors, private backyard and off street parking via rear alleyway. Home may need some updates, but still very habitable. May not qualify for all loan types, cash or conventional financing will work. Walking distance of everything going on in Downtown, come check it out!

This 1,961 Sq. Ft. Brick Ranch residence is in excellent condition and has more than enough room to spread out... 3 bedrooms, 2 bathrooms, living room, dining room, den/family room with egress to rear deck, kitchen open to the dining room and den with fireplace. The laundry/mud room is conveniently located between the foyer and large garage. HVAC is 4-5 years old, New water/sewer lines to the street... walk to the water, restaurants, shops, college, hospital if you need to...

Buying a new home in historic Chestertown continues to be the best option on the Eastern Shore for those looking to retire or start a new family surrounded by the tranquility of upper shore living. This is a unique opportunity to buy an affordable, yet brand new home located centrally in town a short walking distance to local stores, restaurants and the new YMCA. Your new home is a short drive from Washington College and Chestertown's historic waterfront district. This NEW CONSTRUCTION single story 3 BR duplex style townhome is complete and ready to move-in with no HOA fees or regulations. This end unit home has a private front, back and side yard with off street driveway. Inside, a modern open concept floor plan, upgraded stainless steel appliances, granite countertops and bright white cabinetry are a welcome invitation to comfortable living. There is a separate laundry room and multiple linen and storage closets to keep your living area organized. All living areas have easy to clean and maintain durable vinyl plank flooring. This single story townhome has 3 generous bedrooms and 2 full bathrooms including a master bath. Both bathrooms have matching granite countertops in modern design which coordinate with the main living area. This private end lot offers a back porch with oversized private storage closet.

Water, water everywhere! This incredibly unique property is situated on a sheltered deep-water creek offering a westerly, southwesterly exposure with uncompromised sunsets. Fairlee Creek offers one of the most convenient boating accesses on the upper Chesapeake Bay. This 1.9 acre property comes improved with 2 homes, a deep water dock with 5-6' depth, an outdoor barbeque patio overlooking the creek, and 575+/- feet of secure shoreline. One of the two homes on this spectacular property is conte-levered above the water offering the feeling of being on a yacht with panoramic views from every room. The second home is a three bedroom, comfortable, one floor rambler with lovely screen porch overlooking the creek. The location of this property is notable in that it is centrally located in unspoiled Kent County and convenient to both historic Chestertown and the bayfront town of Rock Hall. Great Oak Marina and Resort is a short stroll of golf cart ride away where the residents of Great Oak Estates may share in the use of the establishment's facilities including the pool, restaurant, beach, and 9-hole golf course. Great Oak Estates is a fun-filled neighborhood where the residents interact well together and the spirits are active in the summertime and peaceful in the wintertime!

Beautiful, elevated views of Fairlee Creek from this enjoyable home, situated out of the flood zone, in a quiet country setting. The private dock has deeper-water, plus there is a very convenient public boat ramp very close to the property. From this protected location, you can boat out to the Chesapeake Bay in just minutes. Gourmet kitchen with an over-sized quartz island and countertops, open to both the dining and living area, as well as the water views, perfect for entertaining. There are two bedroom suites on the first floor, as well as a third bedroom and bonus room on the second. Hardwood floors throughout. Brick-floored porch faces the water to enjoy the view. A delightful screened porch on the other side of the house will become another favorite spot. Just minutes to downtown Rock Hall and Chestertown. Under two hours from Philadelphia, South Jersey, DE or DC;. Don't miss this comfortable waterfront property, perfect as a family retreat or retirement destination.

Don't want the hassle of going up & down stairs but still want house space? This is not your ordinary rancher - it's oversized 30ft wide with over 2700sqft of living space and there's no other like it in the sought after Coventry Farms. This home is one of the larger lots from the original building development sitting on just over a half acre. Hardwood floors & 9ft ceilings. New roof in 2019. Energy efficient 22-seer dual-stage hybrid-heat pump HVAC system. Never run out of hot water with the Navian tankless hot water heater. Always wash with clean water from the whole-house water filtration system. Always drink clean water from the reverse osmosis system at the kitchen sink. Oversized 2 car garage, 25x30 with 12 ft ceilings that can fit a car lift. Lofts for extra storage space. Attic can be used as storage OR can be finished to add another 1,000+ of living space. Living space includes a Great Room with lots of natural light. Kitchen includes stainless steel appliances. Master bedroom with large walk-in closet. Sunroom & back deck lead out to a wide open backyard. Low maintenance landscaping. No HOA. Only minutes to downtown Chestertown, restaurants, shopping and marinas. Room Measurements Garage 25'x30' ceiling 11' Kitchen 17'x 15' Dining room 13'x15' Living room 17'x 19' Front sitting room 13'x15' Master bedroom 17'x15' Bedroom 2 13'x11' Bedroom 3 13'x11' Sunroom 16'x17'

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.

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 Chester River get-a-way with extensive accessible river frontage. Private setting with approximately 3-4 acres of solid ground with 12-14 acres of marshland which offers excellent waterfowl hunting! Included is a 2 bedroom, 1 1/2 bath elevated, (over a 3-car garage) ranch style home. Views of unspoiled farmland across the river. These types of properties are hard to find and rarely come on the market! Deep Landing public boat ramp located is just down the road. Located in Queen Anne County just minutes to downtown Chestertown and easy access to Rt 301. Waterfowl shoreline permit in documents.

New Construction 2 story 3 BR 1.5 BA duplex style townhome available in historic Chestertown. Townhome will be completed and ready for move in February 2022. Modern open concept floor plan with ample living and kitchen areas. Kitchen upgraded stainless steel appliances, granite countertops and bright white cabinetry. Durable vinyl plank flooring throughout home with plush carpet in bedrooms. All bathrooms with modern fixtures and granite topped vanities. Plenty of closet storage including private storage unit on covered back porch. This is a unique opportunity to own a brand new home on Maryland's Eastern Shore. The property is conveniently located a short walking distance to local stores, restaurants and Kent County's brand new YMCA; a short drive from Washington College and Chestertown's historic waterfront district.

Waterfront Lot with dilapidated residence. Existing well and septic.