Welcome to 119 Darden Road, a lovely ranch-style home nestled in Chestertown, MD. This charming residence offers 3 cozy bedrooms and 2 bathrooms across 1,424 square feet of living space, perfect for comfortable living. The eat-in kitchen, complete with a handy stove, sets the stage for delightful meals and gatherings. Enjoy the warm ambiance of a fireplace in the spacious living room, enhanced by recessed lighting. Step outside to a large deck overlooking a 15,000 square foot lot, perfect for relaxation and entertainment. This home features a playground and tennis court access for leisurely afternoons. With an attached garage, air conditioning, and in-building laundry, convenience is at your fingertips. Water enthusiasts will appreciate the nearby water access, while pickleball fans can enjoy a game on the community court. Situated in a friendly neighborhood, this home combines comfort with a variety of amenities to suit your lifestyle. Whether you’re cozying up by the fireplace or exploring the outdoors, 119 Darden Road is ready to welcome you home!
109 South Water, along with the historic Custom House, is a bookend to a small, but iconic, cluster of historic (c1900) townhouses that give pause to every passer-by, especially those equipped with a lens. Beautifully designed and maintained block-wide landscaping, individually maintained, provides exceptional street appeal. The smallest (2064 square feet) of the four clapboard houses, all with engaging front porches, has the benefit of additional light from its' six southern facing windows overlooking the waterside lawn, with sculpture, of the historic residence of the President of Washington College. Two quaint river side porches, one screened, guarantee that calm, cool, collected vibe. In 2024, a substantial restoration effort focused on new mechanical systems (including electrical) kitchen and laundry appliances, rebuilt front porch and roof, and the opening up of the two third-floor bedrooms into a beautiful street to riverside space, currently a tech-heavy creative office space but could be earmarked for an amazing primary suite. For the future-minded, well-funded buyer(s), a flawless expansion plan, with HDC approvals, by architect John Hutchinson, are available for use.
Welcome to your private Eastern Shore retreat on 1.37 acres. Built in 2018, this beautiful custom one-level home is thoughtfully designed for relaxed, everyday living and effortless entertaining. Sun-filled and inviting, the open layout creates a warm, comfortable atmosphere—perfect for gathering with family and friends or enjoying quiet moments at home. The home features 3 bedrooms, 2.5 baths, and a flexible bonus room or home office, ideal for today’s lifestyle. At the heart of the home, the gourmet kitchen impresses with granite countertops, rich Java-colored cabinetry, a weathered gray coffee bar with wine/beverage cooler, an oversized island, and stainless-steel appliances. The open kitchen and dining area make both casual meals and entertaining a pleasure and open to the large light filled family room. Both areas have vaulted ceilings. Step outside to a spacious backyard with patio and updated landscaping, offering endless opportunities for outdoor dining, entertaining, or simply enjoying the privacy and open space. A 14×14 shed adds additional storage, while the attached two-car garage with shelving and a workbench provides convenience and functionality. Just a short drive away, enjoy Chestertown’s waterfront lifestyle, including restaurants, a farmers' market, parks, festivals, river cruises, and the vibrant presence of Washington College. Tucked just minutes from Route 301, this property offers a rare balance of peaceful rural living with convenient access to Middletown, Dover, and historic Chestertown. Plus, conveniently located approximately 90 minutes from Washington, D.C. and Philadelphia. This is more than a home—it’s a lifestyle. Schedule your private showing and discover all that this special property has to offer.
Welcome to Chester Harbor. This one level home offers 3 bedroom 2 baths with LVP flooring in living room, kitchen and dining area. Fenced in backyard and a detached Garage/shop. Currently set up as a "Zen Den" offering electric and heat/air from own mini split. Could be converted back to garage if desired. Photos to be taken 1/13
One level rancher with new HVAC, new 200 amp electric panel. The water conditioner is owned, and the water heater is about 2 years old. There is a wall mounted propane heater, but with the new HVAC this can be removed if desired. The current owner says the wall unit heated the entire home for him. The home has beautiful farmland views, mature trees, and has a lovely cottage feel. Last sold in 2001, this property has been updated with an enclosed porch, a trex deck, and a patio area. Just enough room for efficient and tidy living. Very well maintained! Easy to show - location is about 8 to10 minutes outside of Chestertown. The one car garage has a workshop area, and for the summer months there is a ceiling mounted exhaust fan which makes for comfortable workspace.
An amazing home located just a few blocks from Washington College! This mostly brick Cape Cod has 4 bedrooms, 3 full baths, formal dining room, living room with fireplace, first floor primary bedroom with cathedral ceiling, Florida room, full basement with fireplace and a 2 car attached garage. The primary bath and Florida room both have radiant floor heating. The 3 bedrooms on the second level are spacious and offer built-ins. There is even a family room with built-ins! The kitchen has all of the major appliances and granite counters. This home has wood floors throughout most of the house. Oil heat, heat pump and central A/C provide for indoor comfort year round. A rear deck provides for outdoor enjoyment. There is a shed for additional storage. This home is situated on a corner and just a short distance to shopping, hospital and downtown Historic Chestertown.
INTOWN Investor Special! This 4-bedroom, 1.5-bath bungalow is full of potential and ready for your vision. Situated on a large, private lot at the end of a quiet street, the home offers solid bones and a detached garage/workshop area that is hard to find! Located just minutes from Chestertown and Washington College. Plenty of space and character, it’s a rare opportunity to create something special in a desirable location. Adjacent to the The Wayne Gilchrest Trail , which is a popular walking trail in Chestertown, MD, also known as the Chestertown Rail Trail. It's a paved, multi-use path that follows the route of a former railway line, connecting various parts of the town. The trail offers scenic views of the Chester River and surrounding areas, and it's a great place for walking, biking, and enjoying nature. Whether you're looking to flip, rent, or restore and make it your own, this property has endless possibilities. The layout provides room to reimagine the interior, while the surrounding lot offers privacy/seclusion for your outdoor events. Enjoy the charm of nearby Chestertown with its shops, dining, waterfront, and vibrant community. With its location, lot size, and upside potential, this diamond in the rough is a smart investment you won't want to miss. Sold AS – IS… Major Rehab Needed...
Fully remodeled by reputable licensed contractor and subcontractors, 104 Iris has had a glow-up and is ready for showing! The clean lines of the new quartz countertops, the weight of soft golden Amerock hardware, Moen fixtures, Wolf two-tone shaker style cabinetry and well-appointed subway tile set the stage in the beautiful new Kitchen and bathrooms. Where a modern feel is met with the softness and simplicity of Neutrals as you move throughout the rooms that offer a timeless yet 2026 vibe! High-quality, low-maintenance LVP flooring has been installed in all high-traffic areas, along with carpet to quiet the bedroom spaces. Many new energy-saving features include architectural shingles, R38 insulation in the attic, crawl encapsulation, new HVAC unit & dehumidifier. Entry from the rear deck and hall to the large laundry area, is conveniently located adjacent to the hub of the home; the kitchen, where it balances aesthetics with functionality. Ample storage, Stainless steel appliances, an "L" shaped counter with seating area, giving all the practical space for your family's needs on one level. Electric has been modernized with new fixtures, premium touch mirrors, multiple remote-operated ceiling fans, USB outlets & recessed lighting. New doors, hardware and keypad entry locks, round out another set of upgrades. Solar lighting, fresh landscaping, and new treated decking enhance the exterior. It's large lot with mature trees, sits back off the road, in a quiet cul-de-sac, offering privacy, safety, and comfort. Backing up to acres of farmland, an extended outdoor living space great for entertaining also provides opportunity for viewing wildlife and sunsets alike. 104 Iris brings rural community living with the convenience of being close to town. Located in the Chester Harbor community in Queen Anne's county, where a 5-minute drive will have you centered in the town of Chestertown, known for its historic charm, river access, and boating opportunities, offering convenient commutes and amenities. Within walking distance of a private community water access and playground, this home has every detail ironed out and waiting for you! Easy to show! Join the Community Association, which is very reasonable and provides water access.
Welcome to 24775 Langford Rd, a quiet countryside retreat just minutes from downtown Chestertown. This well-maintained three-bedroom, one-bath home sits on 1.27 acres and offers a peaceful setting with ample outdoor space. The property features a generously sized three-car detached garage/workshop and a large Trex deck with hot tub, ideal for relaxing or entertaining. In 2018, the home underwent a comprehensive renovation, with all major upgrades completed at that time, including the roof, windows, siding, gutters, storm doors HVAC system, well, and full crawl space encapsulation. The interior was also updated in 2018, highlighted by refinished original hardwood floors and a remodeled kitchen with all-wood cherry cabinets and stainless-steel appliances. With extensive updates already done, this property combines rural privacy with convenient access to town. Be sure to schedule your appointment today!
Welcome to peaceful country living with modern comfort. This beautifully updated 3-bedroom, 2-full-bath home sits on a private 2-acre lot with mature trees lining the property and a cornfield backdrop for exceptional privacy. Thoughtfully designed for everyday living and entertaining, the home features a spacious rear deck, perfect for hosting family and friends in a quiet, serene setting. Inside, you’ll find a renovated kitchen, remodeled bathrooms, updated windows, freshly painted and primed interior, new doors, and a newer washer and dryer. Major system upgrades include a newer HVAC, updated septic system, and a whole-home water filtration system. Solar panels help keep electric bills lower than average, offering long-term savings. The property also includes an oversized 2-car garage with two new garage doors and openers, plus a separate shed for additional storage. Enjoy the best of Eastern Shore living just ½ mile from Fairlee Creek, where you can take advantage of boating, fishing, and swimming. Easy to show—schedule your private tour online today and experience the space, privacy, and lifestyle this home offers. Motivated sellers, move in ready!
Discover an incredible opportunity in the highly sought-after Coventry Farms community—one of the rare chances to get into this neighborhood for under $500K. This inviting Colonial offers the perfect blend of comfort, charm, and value, with plenty of room to make it your own and build equity over time. Step inside to a warm and welcoming layout featuring thoughtfully designed accent walls, a formal dining room, and a bright breakfast room off the kitchen—perfect for both everyday meals and special gatherings. The kitchen includes stainless steel appliances and generous cabinet space, making meal prep simple and convenient. Upstairs, the primary bedroom features bamboo flooring, a walk-in closet, and an attached bath with a double vanity. Three additional bedrooms offer comfortable, flexible space for guests, hobbies, or a home office. The finished basement is a major bonus, providing expanded living space ideal for a playroom, media room, home gym, or whatever suits your needs. Set on a corner lot with a fenced yard and a large back patio, this home is perfect for outdoor enjoyment. A side-entry garage and off-street parking add even more convenience. With strong bones, great space, clean functionality, and an unbeatable price for Coventry Farms, this home is ideal for buyers who want to move in comfortably now and personalize over time. Don’t miss your chance to secure a fantastic property—and instant equity—in one of the area’s most desirable neighborhoods.
Great rancher in Chester Harbor on the Queen Anne's County side of Chestertown. Fresh paint and carpet throughout. Both bathrooms are completely remodeled. The kitchen could use updating, but the space is great and the appliances are in excellent condition. Plenty of room to add a kitchen island and still have space for a table. Nice 2 car detached "pole barn" style garage. Fenced back yard. This property has a lot to offer!
Picture Perfect Colonial in Coventry Farms – Chestertown, Maryland Welcome to 218 Camelot Drive, stunning colonial 3,932 total square feet of maintained living Situated on a beautifully landscaped corner lot in the established Coventry Farms community, this home features a fenced backyard with vinyl fencing—ideal for privacy, pets, and play. A brick paver patio with pergola and a creates multiple outdoor living zones perfect for entertaining, with direct access from the breakfast room. Inside, a light filled two story foyer welcomes you with elegant architectural details including crown molding, chair rail, wainscoting, turned stair railings, and hardwood floors throughout the main level. Neutral paint enhances the home’s timeless appeal. The gourmet kitchen is designed for both everyday living and entertaining, featuring stainless steel appliances (including a French door refrigerator), custom cabinetry, pantry, granite countertops, tile backsplash, and a center island with breakfast bar. The adjoining breakfast room or bonus space, framed by picture windows and a cathedral ceiling, is perfect for morning coffee or hosting holiday celebrations. The main level offers formal living and dining rooms, a convenient powder room, and a spacious family room highlighted by a floor to ceiling stone, wood burning fireplace with raised hearth and custom stone mantel—an inviting gathering space for family and friends. Upstairs, the primary suite is thoughtfully positioned for privacy and boasts double door entry, a walk-in closet plus an additional closet, and a luxurious ensuite bath with dual vanity, soaking tub, and stall shower. Three additional generously sized bedrooms and a full hall bath complete the upper level. The finished walk out lower level expands your living space with a large recreation area, a possible fifth bedroom, full bath with stall shower, a finished bonus room ideal for a fitness area or media room, and an oversized laundry, utility, and storage area with abundant space for seasonal and long-term storage. Conveniently located just minutes from shopping and local dining favorites, and a short drive to Historic Chestertown along the Chester River, you’ll enjoy easy access to charming boutiques, restaurants, galleries, Washington College, and rich cultural and historical attractions.
Great Chestertown location in College Heights. Large corner lot consisting of .51 acres. This home needs to be remodeled but has great potential and a lot of floor area. The old carpet has been removed down to sub flooring. Lovely sunporch, garage, off street driveway, and entrance courtyard are just a few features! Spacious rooms too! Close to Washington College, Downtown Chestertown, and Shopping Centers.
Brand new home in Historic Chestertown available for move-in Right Now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Additional highlights include exclusive financing opportunities with zero down payment loans, paid closing cost programs, and discounted interest rates—making it possible to own this home for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown's most historic locations.
Discover this well-maintained 2004 rancher located in a water-privileged community with access to the Chesapeake Bay. This charming home offers 3 bedrooms, 2 full baths, and beautiful wood floors throughout. The full unfinished basement is already roughed in for a future bathroom, giving you outstanding potential for added living space. A floored walk-up attic provides even more room for storage or expansion. Additional features include an attached garage and a screened porch perfect for enjoying the outdoors. Tolchester Estates offers the relaxed Eastern Shore lifestyle buyers love—quiet streets and access to the Bay.
**To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to a private second floor balcony. There are two additional bedrooms that share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.
**To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to a private balcony. There are two additional bedrooms that share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.
**To be built! Welcome to this beautifully designed 2,784 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 4 bedrooms and 3.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. There is a first floor primary bedroom for one-floor living options. Upstairs, the second primary suite features a spa-like bath, large walk-in closet, and access to the private balcony. Two additional bedrooms share a full bathroom. Catch a glimpse of the Chester River from the front porch or upper covered balcony, the perfect place to enjoy morning coffee or evening cocktails. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club. Listing Office
**To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space for guests. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and sliding doors to the second floor balcony. There are two additional bedrooms, each with their own full bathroom. the upstairs is complemented by a convenient second-floor laundry. This home is designed with future needs in mind, offering the option of a residential elevator for effortless access to all levels. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.
**To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to the private balcony. Two additional bedrooms share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. Catch a glimpse of the Chester River from the front porch or upper covered balcony, the perfect place to enjoy morning coffee or evening cocktails. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.
**To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath and large walk-in closet. There are two additional bedrooms that share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.
*Days on Market Reporting Incorrectly- Property listed Oct 30, 2025* Nestled just outside of historic Chestertown, minutes from farmers market, waterfront park and local shops and eateries. This home offers the best of small-town living with modern updates at every turn. Step inside to discover wood floors, a private home office, and an inviting open-concept kitchen featuring luxury countertops and a sunroom bump-out with ample natural light—ideal for morning coffee, reading, or cozy dinners. Upstairs, the spacious primary suite offers a true retreat with a walk-in closet, en suite bathroom, and the convenience of an upstairs laundry room. The fully finished basement adds exceptional versatility, featuring its own private entrance, kitchenette, full bath with steam sauna, and open-concept living/bedroom area—perfect for guests, or entertaining. A dedicated workroom completes the lower level, ready for projects or hobbies. Outside, enjoy your fenced-in backyard oasis complete with a deck. This home has been meticulously cared for and thoughtfully updated, including: New roof, gutters, and gutter covers (2025) New HVAC system – furnace and A/C (2024) New 80-gallon water heater (2022) Fully renewed basement (2022) with new flooring, carpet, paint, and dual sump pumps Finished garage (2022) Ornamental Fence (2020) Furnishings Negotiable .
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.
