Chestertown MD Real Estate & Homes for Sale

Get the best of both worlds with this adorable renovated 2 Bedroom 1 bath home in Tolchester Estates. Tastefully upgraded with pergo wood flooring, upgraded tile bathroom, cozy family room and kitchen. Perfect for the first time home buyer and just two blocks from the Chesapeake Bay. Tolchester Estates offers a community beach and Tolchester Marina offers the Shanty Beach Bar. Come and take a look.

Beautiful and well maintained home in Chestertown's College Heights, close to the college and all that Chestertown has to offer. Even provides quick access to route 213 for commuters. Possibilities are endless for this 1960's Rancher, could be your home or a solid investment for a lifetime. It's built like a rock and offers gleaming hardwood flooring, refinished bathrooms, large master bedroom, exceptional wood burning fireplace, and a full basement that could add another level to its beauty.

Three bedroom ranch home located in HEATHER HEIGHTS, south of Chestertown, near Chester River Yacht and Country Club and a short walk to the Chester River. Large lot that backs up to open space and privacy.

Own this home less than the cost to rent! 3 bedrooms, a remodeled full bathroom, living room, office, and wood floors complete the main level. The lower level features a spacious kitchen opening to the family room, another full bathroom, laundry room and ceramic tile floors. Outside is a driveway for off street parking, a fully fenced backyard, and large shed with workbench and electric. Within walking distance to Downtown, Washington College, the hospital, and the Chestertown dog park, this is a great home for first time home buyers or investors looking for great return!

Don't miss this 3BR, 2BA charming home with open country kitchen, large living room, den and spacious master bedroom with master bathroom and walk-in closet. Nicely situated with front and backyard overlooking farmland. Freshly painted, new septic and new HVAC! Just minutes to everything Chestertown has to offer; Washington College, restaurants, local shops, new marina and much more.

Hidden away in a private park-like setting, this wonderful waterfront retreat is ideally situated to take advantage of panoramic views and access to Worton Creek and the Bay beyond. This parcel is on a point of land with about 1000 feet of water frontage. The gracious Main House sits on the high ground of the property with the quaint and charming 2 BR 2 Bath Guest House below at waters edge - making it a great rental cottage. The main house consists of about 3500 sf and the guest house has about 1200 sf. Both have separate private lanes and easy access to the dock with boat lift and 3-4 MLW. When you enter the custom built main house, you are immediately drawn into the dramatic vaulted great room, designed like the bow of a ship, with water views all around plus an impressive wood burning fireplace. Glass doors open out to the wrap-around deck. Just off the great room is the expansive kitchen with center island, separate gas fireplace, and informal dining area with more windows framing the incredible views. The spacious separate dining room offers plenty of room for entertaining friends and family. The Master Bedroom with two closets and ensuite (radiant floor heat), adjoining screened porch and Hobby Room are all ideally located at one end of the home - well situated to take advantage of the water views. Three additional bedrooms plus office and two full baths are located at the other end of the home - also offering beautiful nature scenes and water views. Additionally, there are closets galore plus an oversized two car garage, lovely grounds, privacy and incredible water views - what more could you want? This is a one of a kind property - private but not isolated. In boating season, you can cruise right across to the Harbor House Restaurant for waterfront dining or over to fuel up your boat at the dock and head out for a day on the Bay and Worton Marina. By car, it is just 15 minutes from either Historic Chestertown or Rock Hall on the Bay - both towns offering a wide variety of dining, shopping and entertainment opportunities. BE SURE TO CLICK ON VIRTUAL TOUR ICON TO SEE INTERACTIVE FLOOR PLANS FOR HOUSE & GUEST HOUSE PLUS ADDITIONAL PHOTOS!

Great opportunity for someone wanting professional office space or would like to convert into a residence! RB professional zoning permits both! Was used as a law office for many years and would be ideal for the lawyer who is ready to branch out on their own. Recently has had mold remediation, documentation is available. The off street parking included is a premium in this location with 4+/- spaces available. Conveniently located in downtown Historic Chestertown and within the historic district. Formal appraisal completed in fall of 2019 and is currently listed under the appraised value.

Welcome to 118 Little Harbor Way, Unit 300 in Chester River Landing in Chestertown Maryland. This one of a kind Penthouse unit has panoramic views of the Chester River and Chester River Bridge. Enjoy your afternoon or evening relaxing on one of the two balconies facing the Chester River. The elevator will raise you to your Penthouse unit and open into the most beautiful condo that you will see. The open, bright floor plan featuring hardwood flooring , spacious rooms, beautiful crown moldings and wainscoting and so much more will cater to everyone's taste. The gourmet kitchen featuring granite counters, stainless appliances and enough storage to meet the needs of a professional chef won't disappoint. Awake in your Master Suite overlooking the river and the wildlife that the area has to offer. The walk-in dressing area and Master Bath are extremely large and beautifully designed. This home also includes a 30' boat slip in the community marina and also a single car detached garage .You must take a tour of this one of a kind Penthouse

Welcome Home to 22428 Great Oak Landing. Pull up to your very welcoming driveway complete with mature landscaping, room for boat, RV, and/or extra cars. Open concept floor plan and an updated kitchen with space to accommodate an eat in table. The beautiful kitchen overlooks the expanded dining area and large living room showcasing the vaulted ceilings and gorgeous beams that warm the space along with the fireplace and add character. The outdoors is sure to entertain with a screened in porch, inground swimming pool & patio, oversized shed all situated on a 1 acre lot. Schedule your showing today and move into this beautiful new home before throwing a housewarming pool party bash with your friends and family!

Bungalow in the town of Fairlee. Cozy home with nice wood floors. Knotty Pine kitchen cabinets. Large lot has old shed/chicken coop and plenty of room for a large garden. No city taxes, but you have the benefit of public water and sewer. Easy to see.

Shows great! Nice hardwood floors, beautiful millwork, built ins were custom made, granite counter tops, open floor plan, living room has a gas fireplace, private master bedroom suite with an electric fireplace and beautiful water views. Both bedrooms have a private bath, and there is a nice office with custom built ins. Beautiful Chester River water views from master suite, living room, kitchen and dining area. Walk out French doors to a private covered deck, overlooking the river, and a fire pit. Quality construction. There is a common propane tank that services the units through Peninsula Gas. Public water cost is covered thru condo fees. Locked common entrance/foyer is well decorated. Correct square footage is 1563

Wonderful home in water privileged Chester Harbor community with a detached 2-car garage! With 3 bedrooms and 2 full baths, this nicely updated ranch-style home offers a large eat-in kitchen with elevated breakfast bar that opens to the living room with a cozy fireplace. The property features extensive hardscaping and nice, mature landscaping as well as a completed fenced rear yard!

Lovingly renovated home in the heart of historic Chestertown, just walking distance to all the shops and restaurants. Original details have been retained throughout the home, including original windows, beams, hardwood floors, bookcases, and more. 3 spacious bedrooms, all with restored hardwoods, master with ensuite bathroom (a rare find in a historic home)! Further family bathroom offering double vanities and tub/shower. Laundry and half bath on main level. Large great room addition on the back of the house, with sliders to deck, overlooking private back yard. Home was just completely renovated in 2019 including new 2 x Zone heat pump with central A/C, tankless hot water (propane), complete new wiring, new kitchen and baths, new windows, new stainless appliances, new/restored floors, and more!

Town-home located in Oak Hollow, a well managed town-home community. This unit is brick fronted with a one car garage. The master bedroom has a cathedral ceiling with large bath with separate shower and tub. There are 2 additional bedrooms on the upper level. The middle level has kitchen with sliders to a rear deck and a living room. The lower level has the garage and an additional room ready for you to finish the way you want it. Close to shopping and restaurants!

This home looks like it has never been lived in!!!. When you enter the two story entrance foyer (pease take off your shoes) you will get a sense of what a new home looks like. The kitchen has wood floors and the dining room has tray ceilings. The family room has a wood burning fireplace that has never been used) and a stylish ceiling fan. There is even a tidy living room on the main level. The upper level has an owners suite and 3 additional bedrooms. The lower level overs a recreation room and a game room. Hunter Douglas insulated blinds are at most windows. This property backs to woods but has a front view of one of the larger community areas. The 2 car garage caps off one of the best homes and locations in Coventry Farms!

Spacious multilevel home with 2 story entrance foyer. Recently updated kitchen with Quartz counters, newer looking cabinets and new stainless steel appliances. New flooring in the family room with wood burning fireplace. There is also a living room with a wood burning fireplace. There is a formal dining room and a rear screened porch. The laundry room is huge and has an additional refrigerator. The HVAC is all new as well!! Property backs to woods and farm land. The garage has space for a small workshop. One of the best locations in Orchard Hill!

You will appreciate peaceful living in this waterfront community on the Chester River just minutes from historic Chestertown. A light-filled and spacious open floor plan is wonderful for enjoying the elegant interior amenities. You will also want to sun bathe or swim in the lovely pool, walk the shell walking paths throughout the community and along the shoreline, go kayaking from the community launching area, or take a bike ride or walk into town. Lots of ways to enjoy the care-free Eastern Shore lifestyle!

Just on the market, two story contemporary home located in water community area. Over 2,000 sq. ft., walk to beach and launching area and waterview. 4 BR, 2 BA with dining room and kitchen area, over a half an acre of ground, has a 40 X 24 ft. workshop with electric, and deck on the back of house, seller is offering new buyer's a home warranty.

Super cute cape cod! Great condition! hardwood throughout except for kitchen and 1 bedroom, new counter tops, kitchen floor, stainless steel appliances, new HVAC. Newer roof! Large fenced yard with deck and shed! Super cute curb appeal!! Great value at 215K

Middle Plantation Circa 1856, better known as Running Fox Farm, is one of the finest hunting farms in Kent County, Maryland - abundant deer, Canada and Snow geese, dove and turkey. The residence has been meticulously renovated, an extensive, well-documented project that includes upgrades such as 400 amp electric service and wiring, updated plumbing, custom restorations true to the period, and more. 213 acres with 166.6 prime soils, 60.5acres in CRP... all on FIVE 30+ acre subdivided, perc-approved lots.

This in town location is perfect - walk to shops and restaurants and enjoy all the activities that Chestertown has to offer. The home is in good condition with new carpet on the first floor. Updated kitchen as well. Come take a look!

This property checks all the boxes! Fantastic location, convenient to Chestertown, with a private, partially wooded lot backing to trees, with no HOA! The 3 bedroom, 2 bathroom ranch-style home offers an updated kitchen with durable composite tile floors, wood cabinets, Corian counters, stainless steel appliances, and a large kitchen island with wood top. The kitchen and dining areas open to the huge living room with beautiful hardwood floors and a wood burning fireplace. Refinished hardwood floors continue down the hall and into each of the bedrooms. The master suite offers an updated bathroom with ceramic tile flooring, double vanity with quartz counters, and a tiled shower with marble floor. A full, unfinished basement adds additional storage and usable space, while the carport offers covered parking. Freshly painted and landscaped, this property is move-in ready!

An exceptional architect-designed 6,105 square foot home perched 100 feet-high on a bluff overlooking the Chesapeake Bay - the Chesapeake/Delaware shipping channel in full view. Included in the sale is the adjacent .66 acre parcel, "LOT PAR 1-2 ON A PL S/S MONTGOMERY AVE." You'll never tire of watching the ships and daily sunsets through the floor to ceiling windows. Floors throughout are finished in quarter-sawn red oak. Bluestone surrounds the house and continues into the entryway that provides a dramatic dining space with a 17-foot ceiling and a waterview as the backdrop. Sweeping open floor plan is graceful and elegant in its simplicity - full of light, angles, white walls and stunning views from every window. Plenty of gallery-like spaces to display your art. A chef-designed gourmet kitchen is a cook's dream, complete with a Thermador gas cooktop and electric double oven, two Subzero refrigerators, a Subzero freezer, under-counter Subzero refrigerator drawers, granite counters, and adjoining butler's pantry and many more custom features. A must see. First floor master suite has two luxurious master bathrooms finished in limestone and two custom designed walk-in closets with built-ins. Nationally known artisan-designed cherry stair rail leads to the guest floor with four bedrooms, three full baths and a huge bonus room, which could make a wonderful studio or game room. There are never-ending bay views from almost every room in the house. Heating and cooling is provided by a geothermal system. A three-car garage continues the house exterior design with matching trim and cedar shingles. Dock your boat at the premier marina just a three minute drive away. Nearby is Rock Hall with more marinas, shops, restaurants, and a world-class jazz venue called the Mainstay. Twelve miles away is historic Chestertown with Washington College and more shops and restaurants. Within two hours to Philadelphia, Baltimore and DC. By appointment only. This is one of the finest designed homes on the Eastern Shore. Be sure to allow plenty of time for your tour.

Buy this lovely one-level home in Queen Anne's County for less than you would rent. Better than new! No wait for permits, weather and contractors etc., no upcharge for option-add-ons. Landscaping is already established, there is already a deck , a shed and concrete driveway, and all the kinks are worked out. Very nice, dark, wood floors in the main living area, Laundry and Utility room. Large master with walk-in closet and en suite master bath with tub and separate shower. Spacious, dark, wood cabinets and warm, granite countertops and pantry. Water Softener. Slider to the rear deck. Attached 2 car garage. Alarm pre-wired. Additionally included: firepit and a new outdoor tent. The boat-ramp and the Chester River are about 150 yards walking distance. Centreville is about 20-25 minutes, the Bay Bridge is approximately 30-35 minutes away. This is a great home for anyone who wants to start homeownership, downsize or just relocate. *** Please take off shoes upon entering ***

Looking for single floor living in Chestertown? Look no further! Well maintained handsome ranch in original section of Coventry Farm. New roof, updated appliances, newer systems, screened in porch, nicely landscaped with mature trees on .71 acre. 3 bedrooms, 2 full bathrooms, living room, separate dinning room and kitchen/family room. Attached 2 car garage. Public water and sewer with no deferred sewer charges. Close to shopping, restaurants, Washington College and the Historic District of Chestertown.