Chestertown MD Real Estate & Homes for Sale

Welcome home!! Check out this adorable 4 bed, 2 bath cozy house located at the end of a cul-de-sac, walking distance from the water. Here you will enjoy an updated modern kitchen that provides a welcoming space to relax. It is well-maintained, featuring a living room with a beautiful fireplace and 2 bedrooms on the main floor. Upstairs you have 2 large bedrooms with another full bath. The basement provides high ceilings and great storage space. This wooded lot has so many opportunities for entertaining. Enjoy kayaking or fishing at the pier! Very close to Chestertown and a short ride to Centreville. Perfect home for the first-time or move-up buyer! Come check it out!

This pristine 4BR, 2BA brick rancher in Kingstown Manor is ready for it's new owners. 1,792 sq ft finished living space - glowing hardwood floors throughout - updated bathrooms with travertine tile backsplash & flooring - new HVAC 2021 - dry bar - meticulusly maintained - The large living room is warm and inviting open to the formal dining room. A spacious breakfast area looks out to the backyard and flows into the kitchen where youâll find lots of counter space, moveable island, granite countertops, stainless steel appliances and nice pantry. 2 car attached Garage with inside access - asphalt driveway - 2 large utility/storage sheds with electric - NO HOA - Walking or biking distance to downtown Chestertown; Farmers Market every Saturday morning, Arts & Entertainment district, Washington College, restaurants, local shops, and much more.

Wonderful turn key living in Chestertown. Whether it is year round or long weekends, Tolchester Village makes it easy to enjoy all the area has to offer. There are plenty of fishing and boating options nearby or take a 25 min ride over to visit Eastern Neck Island to enjoy multiple viewing, hiking and water activities. So close to Rock Hall and several Marina's with Tolchester Marina just 1.8 miles away. Maybe a day in town suits you perusing the quaint shops and or dining at one of numerous options. Then there is always the possibility of relaxing on your very own patio which backs up to protected forest land. Once home, you have a fully renovated 2 bed 1 bath on two levels with L shaped kitchen including laundry and Dining/Living combo leading to patio with in ground fire pit and large outdoor storage closet. Let this be your village!!!

This move-in ready Verona boasting 2,302 square feet is a three-story home that offers five bedrooms, and three and a half bathrooms. This well-designed home has an inviting foyer that opens to the spacious family room. The family room is open to the dining space and the family-friendly kitchen with stainless steel appliances, a large corner pantry and a peninsula with additional room for seating. A powder room is conveniently located on the first floor tucked away in a private nook. This roomy floor plan allows the entire family to live comfortably with the ideal amount of space and room for flexibility. The upstairs owner's bedroom with an en suite bathroom and a walk-in closet sit in the back of the home for privacy. There are three additional bedrooms and a secondary bathroom on the second floor. The third floor offers the fifth bedroom and a third full bathroom, as well as an option flex or storage room. The Verona includes the exclusive D.R. Horton Smart Home® Package through ADT giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

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 at the lovely pool, stroll the shell walking paths throughout the community and along the shoreline, go kayaking from the community dock, or just sit back and relax while enjoying the Eastern Shore lifestyle.

Motivated Sellers!!! Encouraging Buyers to Make Offers!! Great Value for this like new Rancher in Chestertown, Queen Annes County! Built in 2018 this lovely home has 3 bedrooms and 2 full baths. The owner's suite is secluded on the left side of the home to provide privacy and the other 2 bedrooms are on the right side with a hall bath. Owners' suite includes a generous walk in closet and large bath with double vanity and tiled walk-in shower. Carpets keep the bedrooms cozy while the Open Plan Living Area showcases beautiful Hardwood floors and a Vaulted Ceiling that makes this home have a wonderful spacious feeling! The Kitchen has beautiful white soft close cabinets with granite counters, an Island with seating, matching white appliances and opens to the Dining and Living rooms. Great for entertaining! Slider doors open to the back yard and shows views of trees and pasture. New Landscaping and trees with a beautiful lawn and a garden shed out back to hold your tools. Two car garage has been updated with insulation, drywall, storage shelves and an epoxy floor. There is a water softener (owned) and an encapsulated crawl space. Just down the street is the Deep Landing Boat Ramp. This 0.65-acre facility on the Chester River has a 14-foot-wide boat launching ramp. This landing is one of the premier boat ramps on the Queen Anneâs County side of the upper Chester River. The cement ramp is adequate for vessels up to 25 feet. No HOA means you can store your boat at home. Beautifully maintained and still like new, this home is move in ready!

The Paige is a gorgeous 1,646 square foot two-story home, that features three bedrooms, and two and a half bathrooms. You will immediately feel at home as you enter the foyer with a coat closet and make your way into the spacious family room. With its open concept, the family room is open to the dining area and the kitchen. The well-designed kitchen offers stylish white cabinets, stainless steel appliances, a peninsula island with additional room for seating and a large corner pantry. The private powder room is down the hall along with the utility closet. Upstairs you will find the spacious owner's suite complete with its private, double bowl vanity bathroom and walk-in closet. The sizeable three secondary bedrooms share a secondary bathroom and allow for everyone in your household to have their own space. The second-floor laundry room comes complete with a washer and dryer and is located near the hall linen closet. The Paige includes a white window treatment package and the exclusive Smart Home® Package giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

Come by this lovely BRAND NEW home in Chestertown, available in Spring 2023. Last one available until later in the Summer of 2023 This home features Luxury Vinyl Flooring throughout, White Cabinets, Granite Counters, Spacious Living Room, Eat in Kitchen area, covered patio off the kitchen, spacious bedrooms including a large primary bedroom suite and much more! These homes are selling faster than they can be built, so come by today and take advantage of this opportunity while it lasts. Special financing programs available, including Zero Down payment loans and closing costs assistance programs so you can own this home for less than renting.

Ready for a January move-in, the Sidney is a 1,849 square-foot two-story home that features four bedrooms, and two and a half bathrooms. A welcoming foyer with a coat closet greets you as you enter your home from the cozy front porch. This open floorplan allows you and your loved ones to spend quality time together while in the spacious family room, casual dining area and kitchen. The well-appointed kitchen showcases an abundance of beautiful white cabinetry, a sizeable peninsula island, stainless steel appliances and a large corner pantry. The laundry room with included washer and dryer is conveniently located off the kitchen on the first floor. Exit through the sliding glass doors in the dining room to enjoy your quiet patio at the back of the home. Also located on the first floor are the powder room, storage closet and an additional coat closet. Upstairs you will find the owner's suite complete with its private, double bowl vanity bathroom and walk-in closet. The additional three bedrooms allow for everyone in your family to have their own space. The Sidney includes a white window treatment package and the exclusive Smart Home® Package giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

This move-in ready Verona, a 2,302 square foot, three-story home, offers five bedrooms, and three and a half bathrooms. This well-designed home has an inviting foyer that opens to the spacious family room. The family room is open to the dining space and the family-friendly kitchen with stainless steel appliances, beautiful white cabinets, a large corner pantry and a peninsula with additional room for seating. A powder room is conveniently located on the first floor tucked away in a private nook. This roomy floor plan allows you to live comfortably with the ideal amount of space and room for flexibility. The upstairs owner's bedroom with an en suite bathroom and a walk-in closet sits in the back of the home for privacy. There are three additional bedrooms and a secondary bathroom on the second floor. The third floor offers the fifth bedroom and a third full bathroom, as well as a finished flex room. The Verona includes a washer and dryer, a white window treatment package, and the exclusive Smart Home® Package giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

The Sidney is a 1,849 square-foot move-in ready two-story home that features four bedrooms, and two and a half bathrooms. A welcoming foyer with a coat closet greets you as you enter your home from the cozy front porch. This open floorplan allows you and your loved ones to spend quality time together in the spacious family room, casual dining area, and kitchen. The well-appointed kitchen showcases an abundance of sarsaparilla cabinetry, a sizeable peninsula island, stainless steel appliances and a large corner pantry. The laundry room is conveniently located off the kitchen on the first floor. Exit through the sliding glass doors in the dining room to enjoy your quiet patio at the back of the home. Also located on the first floor are the powder room, storage closet and an additional coat closet. Upstairs you will find the owner's suite complete with its private, double bowl vanity bathroom and walk-in closet. The additional three bedrooms allow for everyone in your family to have their own space. The Sidney includes a white window treatment package and the exclusive Smart Home® Package giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

Available move-in ready home in The Village at Chestertown! The Verona, a 2,302 square foot, three-story home, offers five bedrooms, and three and a half bathrooms. This well-designed home has an inviting foyer that opens to the spacious family room. The family room is open to the dining space and the family-friendly kitchen with stylish gray cabinets, stainless steel appliances, a large corner pantry and a peninsula with additional room for seating. A powder room is conveniently located on the first floor tucked away in a private nook. This roomy floor plan allows the entire family to live comfortably with the ideal amount of space and room for flexibility. The upstairs owner's bedroom with an en suite bathroom and a walk-in closet sits in the back of the home for privacy. There are three additional bedrooms and a secondary bathroom on the second floor. The third floor offers a fifth bedroom and a third full bathroom, as well as a flex room that could be used for storage. The Verona includes a washer and dryer, a white window treatment package, and the exclusive Smart Home® Package giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

This move-in ready Paige is a 1,646 square foot two-story home, that features three bedrooms, and two and a half bathrooms. You will immediately feel at home as you enter the foyer with a coat closet and make your way into the spacious family room. With its open concept, the family room is open to the dining area and the kitchen. The well-designed kitchen offers stainless steel appliances, classic white cabinets, a peninsula island with additional room for seating and a large corner pantry. The private powder room is down the hall along with the utility closet. Upstairs you will find the spacious owner's suite complete with its private, double bowl vanity bathroom and walk-in closet. The sizeable three secondary bedrooms share a secondary bathroom and allow for everyone in your household to have their own space. The second-floor laundry room comes complete with a washer and dryer and is located near the hall linen closet. The Paige includes a white window treatment package and the exclusive Smart Home® Package giving you complete peace of mind living in your new home.

A unique opportunity! This charming brick building was originally built in the 1800s as a chapel named Mowbray Chapel, eventually abandoned and then the interior was completely rebuilt in 2021 with electric, utilities, a new well and septic. A SIMPLY STUNNING light filled space that has been used as a residence and entertaining venue. Completed with the highest quality of materials and a brand new kitchen, full bath room and laundry room as well as a gas wood stove yet blended with the large windows, gorgeous brick walls, high ceilings and substantial woodwork. A true blend of old world elegance and modern amenities. Nestled among the mature trees on a 3+ acre property, there is also good outdoor space with a lawn, woods and a pond combined to offer spectacular outdoor areas year round.

This listing offers the unique opportunity to own two waterfront parcels, one improved by a beautiful 3-4 bedroom cape, and an adjacent perc approved lot all located less than a mile from Chestertown. The addresses are 121 Lyons Ln. which is 1.9 acres, 118 Lyons Ln. which is 1.2 acres and 117 Lyons Ln. which is .44 for a total of 3.5 acres. They are being sold together and the tax information is for all three lots. The cape is on the 1.9 acre wooded lot and features premium materials and finishes. There are yellow pine floors reclaimed from Camden Yards, crown moulding, wainscoting, panel doors, fireplace, sun room and a master bedroom on the first floor. The second floor has two bedroom and a third room which could be a bedroom, office or 2nd floor family room. The second floor bathroom is huge and has just been remodeled. There is also a separate studio or home office, also recently remodeled, in the rear yard with AC/Heat. A Williamsburg inspired garden surrounds the studio and the rear yard is partially fenced. The waterfront is a quiet creek right across the Chester River from the historic district. The owners have a permit for a new dock and it will convey. By the water is a large screened in Gazebo perfect for crab feasts or for enjoying the abundant wildlife. The second waterfront lot is 1.2 acres, not buildable, but it does allow for more water access. The third lot is .44 acres, perc approved, level, cleared but with some mature trees . A second home could be built for a family compound or a carriage house, guest house or barn. Or, simply hold on to it as an investment. Lots of options so come take a look!

Brand New Home.....3 bedroom, 2 bath contemporary rancher on 1 acre, gorgeous stylish kitchen with Island/breakfast bar, primary bedroom with full bath and walk-in closet, family room overlooking 12x23 back patio and separate laundry room. Upgrades include large primary walk-in closet with built-ins, custom entry storage, floating shelves, pella windows and gutter guards. Beautiful private country setting with lots of wildlife. MHBR #9045

Lovely rancher on over 3/4 of an acre. Private country settling but only 10 minutes to town. Bedrooms are split with the owner's suite on one side and the two additional bedrooms on the other side. Nice wood stove in the living room for a warm, cozy heat during the winter. Beautiful hardwood floors throughout most of the house. Formal dining room. Deck off the living room with pretty views of the back yard. Large uninished basement. $300 road maintenance fee.

Welcome to 626 High St, she is just adorable. The hardwood floors throughout this 3 level home have withstood the test of time and are gorgeous! You immediately feel at home! Lovely fixtures, which are probably original to this home add to the charm. The dining room is very generous in size. The main level has an office, powder room, a nice kitchen with an eat in breakfast bar. There are four bedrooms, and 1.5 baths all total. This home has been a rental for a few years, but the owners have maintained it very well. There are just a couple of tweaks to be made, and the owners are working on that as well. The owner has explored the possibility of a possible building lot on the Lynchburg side. There may be a possibility of that with local zoning approval. Nothing is set in stone, but the new owner could explore further, if desired. In the historic district, four blocks to downtown, but close to Chestertown's Rail for Trails, which is a nice, paved path through Chestertown. Enjoy Washington College and all it has to offer to the community, local restaurants, a thriving artists community, music, the farmer's market, artisans, charming shops, and friendly welcoming people! There is a health food store, coffee shops, two grocery stores, hardware store, a local golf course at Chester River Yacht and County Club, bocci and pickle ball teams you can join! Like to kayak and canoe? You can easily do both on the Chester River, or Radcliffe Creek.

Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away.

Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away.

Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. A short walk to downtown shops and restaurants.

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! THE SELLER JUST REPLACED THE WHOLE ROOF AND MORE. Sale is As-IS

Completely renovated 4 bedroom waterfront condominium located in the heart of historic Chestertown adjacent to Wilmer Park. Completely new community dock with two deeded boat slips and new boat lifts. Easily walkable to the main commerce area of the town including shopping and restaurants. Condominium renovations include but not limited to new kitchen, new baths, hardwood floors throughout, new dock, recently replaced roof, new HVAC systems . The perfect blend of waterfront/in town living.

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.

Waterfront Lot with dilapidated residence. Existing well and septic.