This gem just outside of Chestertown will be active mid-April. New HVAC, new roof, new flooring and other upgrades! Great living space with a front porch and back patio. Large backyard that overlooks beautiful farm fields. There is a one car detached insulated garage. This home offers close proximity to Rock Hall and all downtown Chestertown amenities, schools, and parks and is only 25 minutes to Middletown's shopping, dining, and entertainment options. Don't miss the opportunity to make this delightful rancher your own. Schedule a private showing today and envision the possibilities of living on the Eastern Shore!
This waterfront farmette is a rare find just a few minutes from downtown Chestertown and features extensive updating. The new kitchen, 2 new full bathrooms, and new roof all from 2024 just to name a few have you set up for many years to come. Most of the property is cleared and grassy making it perfect for your equestrian retreat on the water. A detached 2 car garage is perfect for vehicles or water toys. The river room is flooded with natural night and offers prime views of the surrounding wildlife. Stay cozy with the wood burning fireplace. Fishing and hunting are prime in this location. Feel a sense of peace and tranquility on this very private 9 acres while being able to drive to the historic district for the shops, art galleries, theatre, and restaurants in less than 10 minutes. Chestertown is located just 1.5 hours from Washington DC, Philadelphia, and Baltimore.
Welcome to 100 Little Harbor Way, a charming home nestled in the desirable Chestertown community of Chester River Landing. This 2 bedroom, 2 1/2 bath home offers the perfect blend of comfort and modern living and is ideal for both quiet relaxation and entertaining alike. Situated in a tranquil neighborhood, you'll find yourself within easy reach of local amenities, including parks and trails, the Chester River Yacht & Country Club, the community deep water marina and yet only minutes to downtown Chestertown and Rock Hall. For those who cherish their time spent boating, there is a community marina and you will have your own PRIVATE DEEDED boat slip which conveys with this home, and provides easy access to all surrounding areas from the Chester River. As you approach this beautiful home, you’ll be greeted by a welcoming covered front porch. Once you enter the foyer, you'll be attracted to water views from many of the windows and love the spacious and open floorplan, simply flooding the home with natural light! Take special note of the gorgeous bamboo flooring, the fresh paint and new carpet found throughout the home. The spacious living room features high ceilings and a cozy fireplace, creating the perfect atmosphere for gatherings. The space seamlessly flows into the dining area and kitchen, which boasts stainless steel appliances, quartz countertops, and a fabulous kitchen island with bar seating for casual meals or allowing guests to gather around. The kitchen also includes a pantry, double ovens, gas (propane) cooking and fabulous counter space, making it easy to entertain guests. A sliding glass door off the dining room leads to the private deck, ideal for enjoying the outdoors and overlooking the peaceful neighborhood, complete with water views! This level also features a home office space with French doors, a convenient powder room and main level laundry room. The upper level is home to the spacious primary suite, which offers a peaceful retreat with a large walk-in closet and an en suite bath with modern finishes. There is an expansive deck off the primary bedroom with a spiral staircase to the lower level deck. This creates a wonderful space for intimate evenings or morning coffee while enjoying your own slice of nature! An additional well-sized bedroom and a full bath are located on this level, providing ample space for family or guests. There is a perfectly placed loft area for reading, crafting or a great second office space, if needed. The upper level family room is nothing short of phenomenal, as it can easily double as a 3rd bedroom, is beautifully suited as a TV room and could readily be used as two separate spaces because of its generous size! The community offers a variety of amenities that make this location truly special. While not a waterfront property, the home is just a short distance from the beautiful Waterfront Fire-Pit Park and the Can Shell Garden Path. Enjoy the picturesque walking paths and serene outdoor spaces, perfect for enjoying the natural beauty of the area. ** Monthly condo fees include $594.67 for the association, $41.14 for the garage, and $94.49 for the boat slip. The condo fee includes access to these wonderful amenities, and the property is conveniently located close to shopping, dining, and historical sites in Chestertown. With easy access to major routes, this home offers the perfect blend of peaceful living and convenient access to all that the area has to offer. Don’t miss your chance to own this beautiful home in an exceptional location—schedule your tour today!
This is a stunning property! It combines elegance and functionality with its spacious layout, beautiful finishes, and thoughtful details. The open floor plan, combined with the cozy living room, pocket doors, and built-ins, creates a welcoming atmosphere. The kitchen, with its quartz countertops and wood floors, is a great space for cooking and entertaining. The main-level split bedroom floor plan offers great privacy, especially with the large owner’s suite and the nearby laundry room. The screened porch with its cathedral wood ceiling and skylights is a fantastic spot to relax and enjoy the private backyard. The upstairs family area is a perfect place to unwind, with the wood flooring and built-ins adding warmth and character. The two additional bedrooms are also generously sized, and the shared bathroom with double sinks and a walk-in shower is a great touch. Plenty of storage with the walk-in attic. Plus, the oversized two-car garage with room for a small workshop is a bonus for hobbyists or those needing extra storage space. Being just a mile from Historic Downtown Chestertown and close to the Chester River Yacht and Country Club adds so much appeal to this home. It really is a one-of-a-kind find.
Welcome to 129 N. Queen Street situated in one of Historic Chestertown's most desirable and sought after locations. Nestled among multiple other restored and renovated residences, this home itself has undergone a tasteful and remarkable transformation. The entire interior has been completely renovated over the past several years utilizing many new modern materials blended with some original existing charm of days before. Upgraded features include a new open floor plan with newer HVAC, new windows, renovated kitchen featuring maple soft close dovetail cabinets, stainless steel appliances strategically situated within the butcher block and decorative concrete countertops, new refreshing tiled bathrooms, a dream laundry room, and a primary bedroom with cathedral ceiling and exposed beams. Classic old school wood floors and antique banister retain the feel of yesteryear. There is a quaint perfect sized rear yard, Three porches, a walk up attic for storage or fourth bedroom potential and much more! Don't miss out on the opportunity to be a member of Chestertown's community with a short stroll to delicious restaurants, boutique shopping, art galleries, cultural festivals/concerts and especially Downtown's renowned farmers market, all of which is just one block from the scenic Chester River!
Big, bold, and beautiful! This wonderfully updated 2 story brick colonial in Chestertown is just minutes walking to the shops, restaurants, college, and waterfront. The first floor is enhanced with a finished sunroom with mini split, well appointed full bathroom adjacent to the office, and the kitchen of your dreams. Traditional aspects remain with a spacious dining room with built ins and living room with fireplace. The upstairs has 4 bedrooms including the primary suite with dressing room, private balcony and en suite bathroom equipped with radiant floor heat. Half of the third floor is finished as well with a mini split and skylights for hobbies while the other half is perfect for storage. Not that storage is a issue with this full basement including a workout room and dance studio as well. The lush grass yard is tastefully landscaped and easily enjoyed with privacy on your rear deck. Keep your cars and favorite toys clean with the 3 car garage. Spare no detail and live luxuriously in this Eastern Shore gem.
A One-of-a-Kind Historic Treasure Reimagined for Modern Living Step into history with this extraordinary Greek Revival chapel, originally built in 1865 as Walton Chapel and later renamed Mowbray Chapel. Nestled on 3.22 picturesque acres in Chestertown’s serene Quaker Neck community, this stunning brick structure has been thoughtfully restored and modernized, seamlessly blending old-world charm with contemporary luxury. Once abandoned, Mowbray Chapel has undergone a breathtaking transformation. In 2021, the entire interior was rebuilt, preserving its soaring ceilings, grand arched windows, and rich brick walls while incorporating high-end finishes and modern conveniences to create a truly one-of-a-kind living space. The fully renovated kitchen and bath provide modern amenities while maintaining historic character, and a gas wood stove and substantial woodwork enhance the warmth and charm of the space. A new well and an advanced ATU/BAT septic system rated for a 4-bedroom home offer long-term comfort and expansion potential. With new high-speed internet connectivity, you can stay connected while enjoying the serenity of this unique retreat. Set on over three acres, the property offers lush green lawns, mature trees, and a peaceful pond, providing an enchanting backdrop for year-round enjoyment. Whether you're hosting intimate gatherings or simply unwinding in the tranquil surroundings, this setting is pure magic. Mowbray Chapel presents endless opportunities, whether as a private residence, a sought-after Airbnb rental, or a charming event or wedding venue. The potential to expand or build additional structures makes this an incredible investment. Located just ten minutes from historic downtown Chestertown, you’ll enjoy easy access to boutique shopping, waterfront dining, farmers' markets, art galleries, and cultural festivals. Explore the scenic Chester River, visit Washington College, or indulge in local seafood at charming restaurants. Don’t miss this rare opportunity to own a piece of history while embracing modern luxury and investment potential. Whether you dream of a peaceful retreat, a thriving Airbnb, or a breathtaking event venue, Mowbray Chapel is ready to make your vision a reality.
Experience the waterfront lifestyle like never before in this stunning mid-century modern home, which seamlessly hangs cliffside over the serene waters of the Chesapeake Bay's Fairlee Creek. Offering unparalleled privacy and exclusivity, this extraordinary residence evokes the sensation of floating on a boat, where every moment feels like an escape to a tranquil paradise. The unique design and architecture of this home harmoniously blend with the natural landscape, offering expansive views of the surrounding water and wildlife from nearly every room. Set on a generous almost 2-acre parcel, the property includes not only the main residence but also a second residence, making it the perfect retreat for families or guests. Together, the two homes boast five spacious bedrooms, providing ample room for relaxation and privacy. Whether you’re hosting family gatherings or enjoying peaceful solitude, the expansive living areas, large windows, and open floor plans invite you to savor the beauty of the bay from within the comfort of your home. Step outside, and you’ll find a private beach perfect for sunbathing, swimming, or launching kayaks and paddleboards into the calm waters of Fairlee Creek. The home also includes its own private dock, offering easy access for boating enthusiasts to explore the Bay’s stunning waterways. For those seeking a sense of community, this property provides access to the neighboring Safe Harbor Great Oak Landing, where residents can enjoy a wealth of amenities, including a marina, pool, golf course, dining at waterfront restaurants, and a lively beach bar—ideal for casual gatherings or sunset cocktails. This home is not just a property; it's a lifestyle—a rare and exclusive opportunity to immerse yourself in the beauty and serenity of waterfront living, with all the modern conveniences and luxury amenities you could desire. Whether you’re looking for a full-time residence or a vacation getaway, this mid-century modern home offers the perfect blend of style, comfort, and natural beauty.
Welcome to this move-in ready home, situated on a premium corner lot in The Village at Chestertown! This charming 1,742 square foot, two-story home offers the perfect blend of comfort and style. The inviting front porch is an ideal spot to unwind with your morning coffee, enjoy the view of the open fields, and watch the clouds drift by. Inside, the well-designed layout begins with a foyer and convenient coat closet, offering a warm welcome as you step into the spacious, open-concept family room that seamlessly connects to the dining area and kitchen. The kitchen features plenty of classic cabinetry, a peninsula island, stainless steel appliances, and a large corner pantry to keep everything organized. A private powder room and utility closet are tucked down the hall for added convenience. Upstairs, you'll find a generous owner's suite complete with a dual vanity bathroom and walk-in closet. Two additional, sizable bedrooms share a full bathroom, and there's also a nearby linen closet in the hall for extra storage. The second-floor laundry room, equipped with a washer and dryer, adds to the home's practicality. This property came with the added benefit of a Smart Home Package through ADT, offering convenience and peace of mind. The fully fenced backyard provides a safe, private space for children and pets to play, while the 8' x 10' shed is perfect for storing lawn equipment, bikes, and more. The homeowner has also upgraded the property with a 12' x 24' garage, complete with electricity and bonus features! This stunning home with well-designed architectural elevations is sited on a premium lot with views of open fields; it is just minutes from downtown Chestertown, known for its charming shops, restaurants, parks, and Washington College. This thoughtfully planned community is complete, offering a fantastic opportunity to become part of it. Don’t miss your chance to make this wonderful home your own!
Opportunity knocks! This 3-bedroom, 1.5-bath rancher sits on a spacious 2-acre lot in Queen Anne’s County. Enjoy the convenience of high-speed internet while taking in the peaceful surroundings. The home features an unfinished basement, offering potential for extra storage or future living space. With some vision and TLC, this property could shine—whether you're looking to renovate or start fresh. Adding to the value is a 2 bay carport and detached workshop! A great investment! Being sold "as-is". The home is a Gibralter model.
Historic charm with a modern floor plan. Live just around the corner walking to the shops, galleries, and restaurants of downtown Chestertown in this beautifully updated Victorian on quiet Mill Street. High end appliances such as Miele and Bosch adorn the kitchen and laundry. Easily converted back into a 3 bedroom. The backyard is well landscaped, has a covered outdoor living space, and a spacious detached hobby shed or office space. This low maintenance property with walkable lifestyle works perfectly for a weekend retreat or year round residence. Chestertown is located less than 1.5 hours from Washington D.C, Philadelphia, and Baltimore.
Do your investments offer these dividends? A premier waterfront location in a premier condominium community and one of the few remaining to-be-built homes! Enjoy broad water views from this new construction two story, free-standing home which offers all of the sought after amenities of waterfront living including breathtaking sunrises over the Chester River, first floor porch and second floor deck. Deep water boat slips available for lease or purchase. Communities features include two docks, pool, grilling and outdoor dining area right on the water, large firepit, area to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more. More information on the construction options available. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club with golf course.
Your home sweet home retreat - a gorgeous 3 Bedroom 2 Full Bathroom Rancher with attached carport and unfinished basement is available to tour! Major renovations in 2020 and maintained to pristine condition. If you are looking for a place to come home and relax - this is the one! Sit on the front porch and enjoy the afternoon sun, calm surroundings or listen to the birds actively chirping. Head out back to a beautiful recently installed large patio with picture frame accent and plenty of room for all your patio furniture, picnic tables, grills and smokers! Tinker in your outdoor shed with separate electric or craft and create in the unfinished basement with large work bench and plenty of unfinished space. Inside boasts an open floor plan, hardwood floors, fireplace, huge separate laundry room / mudroom, picturesque bathrooms and a true primary suite. Putting your mind at ease.. this home has a whole home generator, so you'll never be without power. Moments to downtown Chestertown or Rock Hall. Festivals, Farmer's Markets, Boutiques, Fine Dining and Small Town Living at it's finest!!!
All one floor living on quiet street with large fenced yard and mature trees close to the bay! Lovely renovations and brand new kitchen with solid white shaker cabinetry including soft close dovetailed drawers and new stainless steel appliances PLUS BRAND NEW ROOF! ABSOLUTE MUST SEE HOME!
Welcome to this beautifully updated end-unit townhouse in the heart of Chestertown! Featuring 3 bedrooms and 2.5 bathrooms, this home is fresh, bright, and ready for you to move right in. The kitchen shines with freshly painted cabinets and brand-new appliances, while new flooring throughout adds a modern touch. Enjoy the convenience of a patio out back—perfect for relaxing or entertaining. Located just minutes from town, you’ll love the easy access to shopping, dining, and everything Chestertown has to offer. Easy to show—schedule your tour today!
This is your chance to own one of the most prominent homes in Chestertown's Historic District already completely upgraded and finished to suit. The Tilley Residence was rebuilt in 1863 and celebrates the Second Empire style reminiscent of the Champs-Élysées in Paris. The neighboring properties on this sought after corner are some of the area's most important including Widehall and the Custom House which was one of the original British Royal Ports of Entry to the Americas. The current owners include one of Kent County's renowned builders and craftsmen who decided to take on this restoration as a passion project to honor its beauty and significance in the community. The home was completely updated in 2024 with new HVAC, Electrical, Plumbing, roofing, and wood flooring. The floor plan was opened up to accommodate your lifestyle in 2025. New bathrooms and kitchen were custom designed. A grand 3 story staircase greets you at the foyer along with arched entryways to introduce you to the level of detail to be found throughout. The front porch allows you to sit back to watch everything happening in town or simply admire the water. The updated layout is designed for optimal flow and natural light. The primary suite captivates you with a fireplace, spacious walk in closet, and tiled shower room with views of the water from two sides. The Mansard roof allows for the full third floor. In the basement there is a partially finished space perfect for your wine cellar along with extra unfinished tidy space for storage. There is also a fenced in rear yard perfect for intimate gatherings, pets, and gardening. Off street parking is a huge plus as well with a detached garage connecting to the rear yard. Due to this property's grandeur and scope of work, the sellers are going to let you decide on some finishes to make you feel you spend wisely. Allowance lists to be provided to interested parties. Turn this important and updated piece of Chestertown History into your Legacy property.
Welcome to The Grove in Chestertown, a picturesque location in Queen Anne's county, located just a short drive from Chesapeake College and historic Chestertown. 130 Sheaffer Road offers peaceful living on over an acre of land with highlights such as main level bedrooms, an expansive fenced in backyard, two car garage, large shed for additional storage, and more! As you enter through the front doors, you're greeted by a large living room with a hallway that takes you to the heart of the home in the kitchen and open concept dining area. Off the kitchen you'll find a potential mudroom that provides access to the backyard, garage, and a separate entrance from the front of the house. Two bedrooms and a full bathroom are located on the first level, with two more bedrooms and a shared bathroom on the second level. Schedule your tour today to experience the peace and lifestyle provided by The Grove in Chestertown!
Two bedroom/one bath dwelling located within the town limits of Chestertown zoned RB offers great investment potential. Very large garage with three sections.
Step into this nearly new, impeccably maintained two-bedroom townhouse located in the highly desirable Chester River Landing community. Recent upgrades make this home truly turn-key, perfect for those seeking comfort and style. Relax and entertain all summer long on the beautifully designed screened-in porch, ideal for enjoying warm evenings and gentle breezes. On the second floor, the spacious primary deck boasts expansive views of the Chestertown skyline and treats you to breathtaking summer sunsets—your personal oasis in this vibrant community. Just a short stroll away, you'll find the charm of Historic Downtown Chestertown and the scenic Wilmer Park, offering the perfect blend of convenience and lifestyle. Chester River Landing is a coveted water-access community offering a host of amenities, including an in-ground pool, two grilling and dining areas, and ample community space. Enjoy the large community dock with boat slips available for sale or lease—a dream for boating enthusiasts. Don't miss this opportunity to own a piece of Chester River Landing paradise!
Your Dream Eastern Shore Retreat Awaits! Welcome to this meticulously maintained home, where charm and comfort blend seamlessly. Whether you're savoring peaceful nights or hosting lively gatherings, this home offers the perfect setting. Step into the breathtaking four-seasons room, where natural light pours in, highlighting an authentic reclaimed barn wood accent wall—crafted from the family’s 1930s farm in Kennedyville. Just beyond, a spacious two-car garage provides convenience, while the backyard invites endless enjoyment with an above-ground pool, a deck, and a cozy fire pit. Inside, the galley kitchen boasts white cabinetry, granite countertops, and stainless steel appliances. Adjacent to the kitchen, a warm and inviting den features a wood stove, abundant natural light, and a spiral staircase leading to the private owner’s suite. The front of the home offers a welcoming sitting room, along with three comfortable bedrooms, a full hall bath, and a convenient laundry closet—all on the first floor. Upstairs, the expansive owner’s suite is a true sanctuary. Enter through a charming foyer into a space filled with natural light from grand portrait windows. Enjoy the oversized walk-in closet, vaulted ceilings, and a private balcony, plus a versatile nook ideal for a desk, workout space, or cozy reading corner. The ensuite bath is a spa-like retreat, featuring a jacuzzi tub, separate shower, dual sinks, and soaring ceilings. This Eastern Shore gem offers a lifestyle of comfort, character, and unforgettable moments. Don’t miss your chance to make it yours! Walk to the water, spend weekends in downtown Chestertown at the famous farmers market, shops or restaurants. Watch a game at Washington College, take a kayak out on the river or make a day trip to Easton, St. Michaels, Chesapeake City or Delaware. This property has everything you could want and No HOA. We have a quote for an alternate staircase install if the spiral staircase isn't your style. Seller is motivated and ready to pass this well maintained home to the next owners just in time for summer!
Lovely 4 bedroom, 2 bath Cape Cod located in College Heights. The house has been freshly painted inside and out and has a new roof. Mostly wood floors throughout the house. Living room has a fireplace but the fireplace is not in working order. The kitchen/dining combo has parquet wood floors. There is a full unimproved basement that was waterproofed sometime in the past and has both inside and outside access. Hot water baseboard heat and one wall A/C unit for heating and cooling. Mostly private backyard.
**Seller is motivated and ready to make a deal – bring your offer today!** Welcome to 314 Devon Dr, Chestertown, MD 21620—an elegant 4-bedroom, 3.5-bath home offering spacious living areas and thoughtful upgrades. The grand foyer leads to a beautifully designed kitchen with a large island, perfect for cooking and entertaining. The expansive master suite features a spa-like bath with a soaking tub, separate shower, and double vanity. The fully finished basement provides additional living space, complete with a full bathroom, making it ideal for guests, a recreation area, or a home theater. Select furnishings in basement are available to convey. Outside, enjoy a fenced-in backyard with a deck leading to a patio, ideal for outdoor gatherings. Conveniently located near downtown Chestertown, this home offers easy access to shopping, dining, and waterfront activities. Schedule your showing today!
Charming & Move-In Ready Discover this beautifully maintained end-unit townhome just minutes from downtown Chestertown! This home has been loved and cared for by the original owners. Offering updated hardwood flooring, carpeting on stairs, fresh paint in the primary living space, a new roof, this ensuring peace of mind for years to come. The spacious master suite features vaulted ceilings, a stall shower and a soaking tub. Additional roomy bedroom on this level with washer and dryer in between Primary bedrooms. Enjoy 10-foot ceilings on the second floor, Living room, dining and Kitchen area with a walk-out second-story deck, Main level as you can enter into the oversized garage with a workshop, perfect for storage or projects. On the ground level, you find a bonus room which is the perfect study /office all ready for you to decide. Powder room on each level. For relaxing and fresh air you have both a deck and patio, this home is again move-in ready. Updatd HVAC unit is another positive and reflection of how the home has been maintained and cared . As an end-unit, it benefits from an abundance of natural light, enhancing its warmth and charm. Conveniently located near shopping, dining, and entertainment, this home is perfect for both weekend getaways and year-round living. Don't miss out on this incredible opportunity—schedule your showing today!
Newly finished 3 Bedroom townhouses with nearly all the desired attributes of town living, with harbor and marina views and access from the marina on one side and waterfront park on the other. A short walk to downtown shops and restaurants. No short term rental restrictions.
Exceptional Chester River Landing townhome with elevated views of the Chester River. Enjoy sunrises over the Chester from the balcony and living space. Beautiful views any time of year. A deep water boat slip is included in the sale. The living room offers, cozy gas fireplace, has beautiful water views all year. This condo boast an open floor plan with tons of natural light, ample room for entertaining and family gatherings. The gourmet kitchen with stainless appliances leads to the dining space which has nice views of the Chester River and community. Upstairs you’ll find the riverfront primary bedroom, there’s even a view from the soaking tub. Additionally, there are two bedrooms that share a full bath. On the first level there is an office space that could also be used as extra sleeping sleeping space. The large two car garage has enough room for two vehicles and additional storage for all your water toys. Enjoy the luxuries of the Chester River Landing community, including a pool, community beach, walking paths, beautifully landscaped communal area, waterfront bbq area and much more. Chester River Landing is located just minutes from Historic Chestertown, with many restaurants, shops and entertainment.
Chestertown is located in Maryland. Chestertown, Maryland has a population of 5,557. Chestertown is less family-centric than the surrounding county with 10.61% of the households containing married families with children. The county average for households married with children is 15.86%.
The median household income in Chestertown, Maryland is $44,665. The median household income for the surrounding county is $64,451 compared to the national median of $69,021. The median age of people living in Chestertown is 39.1 years.
The average high temperature in July is 87 degrees, with an average low temperature in January of 25.4 degrees. The average rainfall is approximately 45.1 inches per year, with 13.9 inches of snow per year.
