This masterpiece is finally complete. Rebuilt in 1863, the Tilley Residence showcases classic Second Empire style on one of Chestertown’s most prominent corners, neighboring Widehall and the Custom House. Expertly restored in 2024–2025 by one of Kent County’s premier builders, the home offers new HVAC, electrical, plumbing, roofing, flooring, and a refreshed open layout. Custom kitchen and baths balance modern comfort with timeless character. A grand three-story staircase and arched entryways welcome you inside. The front porch overlooks town and offers water views. The primary suite includes a fireplace, walk-in closet, and a tiled shower room with views from two sides. The Mansard roof provides a full third floor, and the basement includes a great wine cellar opportunity plus ample storage. A fenced rear yard, off-street parking, and a detached garage complete this rare offering—historic charm blended with modern amenities.
This 2-bedroom, 1.5-bath bungalow offers a bright, open layout with updates throughout. The home features a sun-filled front room, an eat-in kitchen with new butcher block seating and updated appliances, and a fully renovated bathroom with new tile and a modern vanity. A rear utility room with laundry provides extra storage and access to a small backyard—perfect for gardening or relaxing outdoors. Located within walking distance to Downtown Chestertown’s restaurants, shops, farmers market, and waterfront, this property is a great opportunity to enjoy convenient in-town living.
**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 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.
HIGHLY MOTIVATED SELLERS- DON'T MISS THIS OPPORTUNITY! This historic 1916 home is charming inside and out. They don’t build houses like this anymore! Featuring 4 bedrooms and 2 full baths, this home is adjacent to Washington College and a short stroll to downtown Chestertown. Three finished levels and high ceilings make the home feel roomier than the square footage suggests. Gorgeous original heart-pine hardwood floors and beautiful molding run throughout. The mahogany-floored porch has interchangeable screens and windows, easily converting from a screen porch into a sunroom. New 6’ pressure-treated pine fence provides privacy in the backyard, perfect for children or pets to enjoy. Adjacent to the fence, the lot also has a driveway with off-street parking for two vehicles. Calling those with green thumbs - a separate fenced garden is ready for your flowers, fruits, and veggies to be planted this spring! In summer 2025, owners completed $60,000 in updates, including a new roof and fully updated electrical wiring as well as fresh interior paint. (As the electrician noted, much to his chagrin, this house is SOLIDLY built - plaster walls were difficult to get through - and have since been professionally patched!) All upgrades were intended to be enjoyed by current homeowners, but they are regretfully moving to be closer to a new job. After updates, home appraised for over $500,000. Instant equity for a lucky buyer!
**To be built! Welcome to this beautifully designed 2,231 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 ,to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, walk-in closets, and doors to the private waterfront deck. Two additional bedrooms share a full bath. the upstairs is complemented by a convenient second-floor laundry. Enjoy broad water views and breathtaking sunrises over the Chester River. The covered porch and expansive windows create a seamless connection to the outdoors, enhancing the waterfront lifestyle of this sought-after 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! Nestled in the sought-after Chester River Landing community, 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.
Turnkey Perfection! Fully Renovated Ranch Home in Desirable Fairlee! Prepare to be impressed by this stunning ranch home that has undergone a complete, top-to-bottom renovation! Offering 1800 sq. ft. of newly renovated finished interior space, this property is much bigger than it looks and provides true move-in ready convenience with zero deferred maintenance. Upgrades Inside & Out! Enjoy peace of mind knowing the entire house has been meticulously updated with major systems and aesthetic finishes, including: Exterior: New Roof, New Siding, New Windows, and a crisp, modern look. Mechanicals: Brand New Heater, New Central A/C, New Plumbing, New Electrical Service, and a New Hot Water Heater. Interior Finishes: New Flooring and fresh, tasteful New Paint throughout. The heart of the home is the all-new, open-concept kitchen, perfect for entertaining and daily life: New Cabinets, Granite Countertops, Tile Backsplash, Stainless Steel Appliance Package. The fully renovated bathroom shines with a new tub/shower featuring elegant tiled walls and floor, new fixtures, and a stylish new vanity. A separate, dedicated laundry room within the house provides excellent convenience and extra storage space, a powder room or second full bath could be easily added to this room as well. The versatile layout includes a second living area that can easily be utilized as a Fourth Bedroom or a dedicated Home Office, adapting to your needs. Out back, you'll find: A beautiful Paver Patio for outdoor dining and relaxation. Plenty of room for parking. A Large, Detached Two-Car Garage is a massive bonus! The garage has its own new roof, siding, windows, electric, and new electric doors, making it perfect for a workshop, home business, hobbyist, or simply superior storage. Don't lift a finger—simply turn the key and start living! This is an unparalleled opportunity for a like-new home in a great Fairlee location. Note: Seller is a licensed Maryland Realtor. Schedule your showing today!
NO HOA OR FRONT FEES: Welcome to 251 Devon Drive located in the desirable Coventry Farms neighborhood. When entering the paved circular driveway, you will find the property meticulously landscaped. The inviting curb appeal welcomes you into the home's foyer where you will find a living room to the left and formal dining room to the right. The foyer then leads you into a spacious kitchen that features a peninsula island with a breakfast bar and cabinetry that offers ample storage and workspace including a separate pantry. Off from the kitchen is a room overlooking the back yard that offers access to the back yard. The primary suite is privately located in rear of home being complete with shower stall, tub, large vanity as well as a linen closet. The two additional bedrooms are located on the opposite wing of home offering separation. The finished basement is quite a highlight with a six-foot glass walk-out door onto the large rear private patio that overlooks an open wooded area that features mature trees, flowering shrubs and perennials. The pleasure of seeing deer and wild turkey stroll through and the morning sound of birds offers a peaceful retreat. Now to come back inside the basement, you will find it amazing. The main room coming in is very large being open to a kitchenette. The large room having a gas fireplace is presently used as a game room. The game room opens to a sitting room with half-bath access. There are additional rooms in the basement that includes a large workshop and another sizable room that could be used as a theatre room, work-out room or for whatever the need may be. The stairs from the basement up into the main level includes a chair lift. The home has a generator and solar panels for energy efficiency, as well as a yard sprinkler system and soaker hoses to keep the landscaping looking its best. This home being located in the historic town of Chestertown offers convenience to the Chester River, cultural festivities, waterfront parks, rail-trail, The Farmers Market, YMCA, hospital, shops and Washington College. The public record reflects the main level being 2135 SF with the lower level being 1800 S.F.
Chester River Charm: Your Gateway to Eastern Shore Living Completely Renovated Cottage with River Views & Endless Possibilities Discover the perfect blend of modern comfort and Eastern Shore tranquility at this beautifully transformed 3-bedroom, 1-bath cottage just minutes from historic Chestertown and the pristine Chester River. Whether you're seeking a weekend escape, investment opportunity, or year-round retreat, this property delivers on every front. The Perfect Package Step into a home that's been thoughtfully reimagined from top to bottom. The open, light-filled interior showcases luxury vinyl plank flooring, fresh paint throughout, and new lighting that creates an inviting atmosphere perfect for both relaxation and entertaining. The updated kitchen features brand-new stainless steel Frigidaire appliances, while plantation shutters and custom window treatments add elegant touches throughout. Every comfort has been considered with new Mitsubishi mini-split heating and cooling systems ensuring year-round efficiency, plus a cutting-edge Stiebel Eltron tankless water heater and energy-saving solar panels that make this home as smart as it is beautiful. Outdoor Living at Its Finest The real magic happens outside, where mature gardens tell the story of seasons past and future. Dogwoods and cherry blossoms frame slate walkways and stone borders, creating a landscape that's both sophisticated and naturally beautiful. The 12x16 treated lumber deck provides the perfect spot for morning coffee with river glimpses, while the 10x12 shed offers excellent storage with its updated siding and metal roof. Location Advantages Position yourself in one of Maryland's most coveted regions, where the Chester River's calm waters offer world-class fishing, kayaking, and boating just 2 miles away at Deep Landing Boat Ramp. Historic Chestertown brings year-round culture with festivals like the famous Tea Party celebration, Saturday farmers markets, vibrant arts scenes, and waterfront dining that draws visitors from across the region. The strategic location offers quick access to major corridors—25 minutes to the Chesapeake Bay Bridge opens up Baltimore and Washington DC markets, while Delaware's beaches and Middletown are equally close.
Chester River Views from Every Angle! Welcome to this stunning Colonial located on the Queen Anne’s County side of Chestertown, offering unmatched views of the Chester River and serene waterfront living. This spacious home features 4 large bedrooms, 2.5 bathrooms, and gorgeous hardwood floors throughout. Enjoy cozy nights by the wood-burning fireplace in the living room and enjoy entertaining in the massive kitchen, which boasts a large eat-in area and picture-perfect views of the river and backyard. The main level also includes a huge laundry room and a 2-car attached garage for convenience. Step outside to your beautiful back deck and large yard, where you can relax, entertain, and soak in the breathtaking water views that make this home truly special. If you're looking for space, charm, and waterfront serenity, this Chester River gem is it!
**Price increase due to the home’s expanded footprint—over 1,200 additional square feet!** **To be built! Welcome to this beautifully designed 3,540 sq. ft. home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The standard floor plan includes 4 bedrooms and 3.5 baths, with the option to expand to 5 bedrooms and 4.5 baths by adding a first-floor guest suite. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath and walk-in closet, complemented by a convenient second-floor laundry. Designed with future needs in mind, this home also offers the option of a residential elevator for effortless access across all levels. Enjoy broad water views and breathtaking sunrises over the Chester River. The covered porches and expansive windows create a seamless connection to the outdoors, enhancing the waterfront lifestyle of this sought-after community. Deep water boat slips are available for lease or purchase. The community amenities 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! Nestled in the sought-after Chester River Landing community, 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.
Welcome to this charming 3-bedroom, 2-bath rancher offering comfortable one-level living in the desirable Chester Harbor community. Set on a spacious 0.76-acre lot on the Queen Anne’s side of the Chester River, this home is nestled in a water-oriented neighborhood—ideal for boating enthusiasts and nature lovers alike. Inside, you’ll find a generously sized primary bedroom featuring a private en-suite bath with a walk-in shower and an impressive walk-in closet complete with a cedar section for added warmth and storage. The kitchen and dining area showcase newer flooring installed just two years ago, creating a modern and inviting space for everyday meals and gatherings. Updated appliances add both style and functionality to the kitchen. Stay cozy and energy-efficient during cooler months with the wood stove, and enjoy comfortable summers with large window units that effectively cool the home. Outside, the fenced yard—installed just four years ago—offers a secure and spacious area perfect for children and pets to play and explore. A detached two-car garage provides ample storage for vehicles, tools, or all your boating and water toys. This inviting property combines comfort, convenience, and a sought-after waterfront lifestyle—an excellent opportunity to enjoy life near the Chester River.
A Rare Opportunity in the Heart of Historic Chestertown Discover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage. Brimming with character and potential, the property currently features a townhouse on one side and two apartments on the other, offering a flexible layout ideal for renovation, income generation, or a creative reimagining. Whether you're envisioning a stately single-family residence, a dynamic live/work space, or a thoughtfully restored multi-unit investment, the possibilities are as expansive as the lot itself. That said, this is not a turnkey property. Significant settling has occurred over the years, and a substantial renovation will be required to bring it back to life. Offered strictly as-is, this is a true fixer-upper for the visionary buyer ready to take on a transformative project. Situated within both the Arts & Entertainment District and Enterprise Zone, this location supports both residential and business uses—making it an ideal candidate for those looking to merge lifestyle, business, and history. Bring your vision, creativity, and tools—and seize the chance to breathe new life into a piece of Chestertown’s storied past. Opportunities like this don’t come along often. Schedule your showing today and imagine the future you can build here. **See updated zoning info from the town in documents
Chestertown is located in Maryland. Chestertown, Maryland 21620has a population of 5,557. Chestertown 21620 is more family-centric than the surrounding county with 21.45% 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 21620 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 21620 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.
