Chestertown MD Real Estate & Homes for Sale

Low maintenance, coastal cottage in Tolchester on nearly a half acre. Only 2 blocks from the community beach. House was completely renovated inside and out, including the 16 x 20 barn. Three bedrooms, 1 1/2 bathrooms. Start enjoying Summers by the Bay!

Lovely countryside Cape Cod on over 3 private acres. Sit on the front porch and enjoy the summer breeze or grill off the back deck and watch the deer in the woods. This home has been meticulously cared for and features a first floor primary bedroom with walk-in closet and ensuite bath with a massive ceramic tile shower. Large formal living room with brick fireplace flows into the kitchen / dining room combo behind with sun-room and back deck. Recent upgrades include: crawl space encapsulation, stainless steel kitchen appliances, downstairs heat pump, backyard fence, solid wood plantation shutters, automatic retractable blinds and more. Quick drive to historic downtown Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market, and a brand new YMCA. Enjoy easy country living on the Eastern Shore. More info and photos to come.

Step into the charm of historic Chestertown with this 2BR/1BA home full of potential. Featuring a screened front porch, spacious layout, and rear alley access, this property is perfect for investors or visionary buyers. Located just blocks from Washington College, the Chester River, downtown shopping, and restaurants, this home offers the ideal setting for a full-time residence, Airbnb, or long-term rental. With some renovation, you can restore it's original character and create serious value in a highly walkable, waterfront community. Sold as-is. No repairs will be made by Seller. Bring your contractor and your imagination- historic opportunity awaits!

Priced To Sell Fast! Renovate & Resell or Buy & Hold, Desirable 2 Level Colonial, Spacious Kitchen, Spacious Bedrooms, Covered Front Porch, Much More!! Just Waiting For Your Personal Cosmetics and Renovations to Make it Shine. Close to Schools, Shopping and Commuter Routes. This Will Not Last! Sold As-Is.

ALL BUYERS, PLEASE DO NOT PROCEED DOWN THE PRIVATE DRIVEWAY WITHOUT AN APPOINTMENT! THANK YOU!! Centrally located between historic Chestertown MD and Rock Hall, enjoy this 3.5 acre property to explore, ride 4 wheelers, have horses, chickens & more! Great hunting, lots of deer and wild turkey! 3 bedrooms, 2 full baths in this cute recently updated ranch home. The kitchen is very spacious and has beautiful quartz countertops and stainless appliances. Eat on counter as well with room for 4 stools. Dark wood LVP floors throughout make this home shine! Washer and Dryer convey with the purchase and a beautiful fireplace as well! Outside you have the very newly build detached garage! Garage is 30 x 40, a total of 1200 square feet with 15 ceilings! It is equipped with electric and a wood burning fireplace. Perfect for all big trucks, big boats and all kinds of ATVs! Nature is all around you at the beautiful home! Call Lori today to make an appointment!

Discover the luxury of coastal living with this masterpiece waterfront property located in a much sought-after location on the Chester River. When entering the home, youre immediately greeted in the elegant foyer that opens to a formal dining room to the right, and an office to the left that could easily be converted to a first floor bedroom. The fully renovated chefs kitchen features state-of-the-art appliances, a spacious island, and ample cabinetry, making it perfect for hosting both large parties and intimate gatherings. The expansive living room features a fireplace and full views of the sparkling waterfront. This meticulously renovated home features 3 bedrooms, each with an en suite bath. The second floor boasts a relaxing combination of a screened porch and an open deck spanning the full front of the house and overlooking the river. The very large primary suite, with it's pampering bath, also has an entrance to the inviting screened porch. When stepping outside, the gracious landscaping calls for you to unwind on the open deck and work on your tan, or step onto your own private dock and explore the river a bit. There is also a covered brick patio, perfect for firing up the grill and eating al-fresco. Located just minutes from local shopping and schools, this paradise offers you a life of convenience, without compromising privacy and luxury.

**OPEN HOUSE JUNE 14TH** Situated on a generous 0.653-acre lot just outside of Chestertown, this property offers the best of both worlds-proximity to town amenities with the added benefit of space and privacy. This well-maintained home features 3 bedrooms and 2.5 bathrooms, including two recently updated baths. The interior boasts a welcoming entryway, formal dining room, and a spacious kitchen equipped with an island, gas cooktop, and a cozy breakfast nook. You'll also find a dedicated laundry room with a convenient side entrance. Flooring throughout the home includes a mix of wood, tile, and carpet, while the living room offers a comfortable gathering space anchored by a working fireplace. Step outside to enjoy the expansive backyard, perfect for entertaining or relaxing. The detached two-car garage includes an additional space ideal for a workshop or home office, plus a loft area with endless possibilities. Don't miss this opportunity to enjoy country-style living just minutes from downtown Chestertown!

Super clean, well-maintained and move-in ready! This charming 3-bedroom, 2.5-bath townhouse offers affordable, low-maintenance living. The main level features a bright kitchen, convenient half bath, in-unit laundry, a spacious living room, and an open dining area with sliding doors leading to a private patio and beautifully maintained common grounds. High Speed internet available. HOA covers lawn care and exterior upkeep-no mowing or yard work required! Ideally located just minutes from town. With current rental rates, why rent when you can own?

Fabulous location in the Chestertown Historic District with lots of room for expansion among brand new luxury homes! 420 Cannon sits on a 5,000 square foot lot that fronts on historic Cannon Street and is surrounded by the new Cannon Square development. Enjoy it in comfort now with plenty of room for new equity over time: Maybe double the house? Add a first floor bedroom suite? A garage? (As always, buyer to verify feasibility of their building plans) Beautiful Kitchen with 42 inch cabinets, granite counters, under cabinet lighting, reverse osmosis water filtration, Rennai tankless water heater and stainless appliances! One full bath on main floor & one on second floor. The friendly front porch welcomes you home after a walk to the Natural Food Store or many other in-town amenities! Walk to your boat, the Farmers Market, shops, restaurants, the Lawrence Preserve, and the serene Chester River waterfront. The bike/walk trail runs right behind Cannon Square from the waterfront to the water tower and Washington College. Some renovations in the home are started & just awaiting final completion by new owner so priced accordingly. Choose & install your own finishing touches! The beautiful large stones out back are historic original curbing that was recovered from the front & moved to the rear. These stones already have a new home to go to unless the buyer expresses an interest in keeping them. This home has been owned & maintained by licensed contractor for 25 years. Ask your agent for the full Seller's Disclosure and plat available in documents.

Buyer Financing fell through, so their loss is your gain! Ideally situated in Chestertowns sought-after Historic District, this charming 1-bedroom, 1-bathroom cottage offers comfort, convenience, and plenty of potential. Enjoy a low-maintenance lifestyle just steps from downtown shops, restaurants, waterfront parks, and Washington College. The home features a bright and efficient layout, perfect for a weekend retreat, investment property, or full-time residence. A fully fenced rear yard provides a private outdoor space for relaxing, gardening, or entertaining. Whether you're looking to settle into Chestertown or searching for a smart investment in a prime location, this cottage is a rare find with room to make it your own.

Looking for that off the beaten path property, here it is! Property located in a water privileged community on the Chester River, access at end of road. Home offers a 1/2 acre lot with mature trees. Property backs to Duck Neck Campground. Subject is sold in as is condition, seller nor buyer can make any repairs. Property is owned by the US Dept. of HUD, HUD Case #241-770004. Insurability Code: UI. Seller makes no representations or warranties as to property condition and HUD Homes are sold â??AS-ISâ? only. Seller may contribute up to 3% for buyers closing costs, upon buyer request. EHO

Charming Chesapeake Bay Home with Stunning Water Views and Incredible Sunsets! Living space is 2699 and the unfinished basement is 1948. Additional guest house adds additional square footage, a kitchen/bath/sleeping area and living room. Discover the beauty of waterfront living in this exquisite home featuring panoramic views of the Chesapeake Bay. Having undergone a comprehensive renovation in 2022-2023, this property continues to impress with ongoing enhancements. The large deck overlooking the pool is the latest improvement. Inside the main house, the open-concept design flows effortlessly from the expansive living room area, and dining area that has nonstop water views. Amazing renovation of the kitchen is a standout feature. The kitchen is equipped with stainless steel appliances, a spacious kitchen island, and ample storage, its perfect for culinary enthusiasts. The primary bedroom offers a luxurious retreat, complete with a large step-in shower and a two-person vanity, showcasing thoughtful design throughout. A charming book nook with access to the water views and landscaping provides an ideal spot for morning coffee. The design includes a walk-in closet, a custom designed ceiling and luxury vinyl tile continued. Throughout the home, the nautical theme is evident with lighting and ceiling fan fixtures. It just won't disappoint. The basement has even more storage and plenty of room for a workout area. Total square footage for the main level is 2569 and Unfinished basement area is 1948 sq. feet Guest House & Garage: Guests will appreciate the new two-car garage that includes a well-appointed guest house upstairs, featuring modern appliances and a balcony that showcases beautiful water views. This space combines privacy with luxury, ensuring a comfortable stay for visitors. Outdoor Oasis: Step onto the covered porch, designed for all-weather enjoyment, and take in the breathtaking vistas of the Chesapeake Bay. The outdoor space is further complemented by a brand-new custom-built deck that offers direct access from the bedrooms, perfect for entertaining. The Gunite pool, complete with a tanning ledge and seating, invites relaxation and fun and water views of the Chesapeake Bay. A convenient changing room and storage for pool toys are located in the garage of the guest house, which also features its own cozy covered porch area providing coverage from any inclement weather The guest house has a a kitchen/and full bath along with a combined living and sleeping area. Additional Features: This home also boasts a walk-in closet and exquisite landscaping that enhances its picturesque setting. Notable renovations include a geothermal well and HVAC system, Hardie Plank siding, and a 320-gallon propane tank that services both the main house and guest house which is leased through Dixie Land. Electric/plumbing/ New foam and spray insulation in exterior walls have all been updated, and a new grinder pump is in place. Additionally, an extra parcel with sewer allocation is included with sewer allocation billed quarterly-check with Kent County for further details. Footprint for a new build would possibly be 2000 SQ feet with the ability to build up. Verify with Planning and Zoning This home is a true gem, offering the perfect blend of luxury, comfort, and stunning natural beauty. Dont miss your chance to own a slice of paradise on the Chesapeake Bay! Whether you are looking for a second home to relax and enjoy or live here year around. It's an incredible home, not overwhelming in upkeep! Turnkey living with amazing water views and incredible sunsets!

Priced over $50,000 below recent appraised value! Perched above the peaceful waters of Rosin Creek, this charming waterfront cottage offers a rare opportunity to create your dream retreat. Whether you are searching for a cozy weekend getaway, a lucrative short-term rental, or a serene place to call home, this diamond in the rough is full of potential. Just a stones throw from historic Chestertown, the property combines seclusion with convenience-making it the perfect canvas for your vision. The large, wooded lot offers privacy, but still allows for beautiful views of Rosin Creek. The existing dock is in need to repair, but is a perfect spot to launch kayaks and paddle boards. With loads of potential, this home is being sold As Is. Information from the contractor retained by the previous owner on work previously performed on the house is available in the documents and a quote for a full remodel is available on request. In addition, a new well pump was installed in 2025. Please do not walk the property without an appointment.

BACK ON THE MARKET due to financing. 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 Chestertowns 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, youll 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. Dont 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.

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.

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, youll 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-�lysées 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.

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 familys 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 owners 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 owners 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. Dont 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!

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.

Three bedroom/one bath rancher located in a water-oriented community just minutes from Chestertown. There is a Home Owners Association; however, is not mandatory to join. Home is being sold as is.

MOVE IN READY!! Adorable, Affordable, move in ready & two blocks from the Chesapeake Bay! Appliances, roof, flooring recently upgraded, beautifully tiled bathroom, Pergo wood flooring. Bright and inviting updated kitchen, Spacious Dining/family rm with vaulted ceilings fireplace, ceiling fan. Enjoy fishing or relaxing at the private community beach or head over to Tolchester Marina & The Shanty Beach Bar. just a very quick trip to entertainment, dining or boating. Great location, just 10 minutes from downtown Chestertown or Rock Hall where you can enjoy shops, marinas, dining and regular events. Level lot with plenty of potential.

Designed by noted architectural historian and restoration consultant, Michael Bourne, Highfield exemplifies a deep appreciation and intimate knowledge of historic architectural composition and its elements. With its steep pitch hip roof, catslide roof slope on one end, tall chimney, and enclosed front entry, in form and style, Highfield is reminiscent of the vernacular farmhouses of southeastern England. Outstanding historic architectural details have been incorporated throughout the houses interior and include a Hamstone fireplace surround and hearth (imported from Somerset, England) in the formal Living Room, antique doors fitted with both original antique and fine reproduction hardware, and a number of custom lighting fixtures. Together, these important details create an inviting warmth and add to its unique character. Highfield is a rare find! The handsome two-story, many-paned window of the Great Room faces SSE and looks out over a stone patio and well-established perennial beds. Additionally, it provides a significant amount of passive solar gain keeping energy costs low - a compliment to the six-zone heating system. The more formal Living Room offers windows on the west gable that afford views of the surrounding fields, expansive grounds and woods. French doors on the south side lead to an ample screened, flagstone-floored porch. The large open Chefs Kitchen, Den/Office, Mudroom, and half-bath complete the first floor. At the top of the stair, a balcony leads across the Great Room to the Master Suite where design details include a tray ceiling, built-in cupboards, dressing room, and spacious bath with separate vanities, shower, and soaking tub with Portuguese tile accents. The second bedroom with full bath is located at the east end of the balcony where a stair leads to the third-floor bedroom with walk-in closets. Access to the attic is found here. Accessible from the mudroom, the full basement includes a large ante-space, spacious laundry, playroom, and workshop. An unusual â??bakeryâ? building with wood-fired brick oven, walk-in refrigerator, and half-bath stands nearby. An additional utility shed is included. See summary of features in Documents Folder.The private 5-acre property is located only 3 miles from Chestertown which uniquely offers swift access to this historic, vibrant town. Chestertown, located in the County of Kent on Marylands Eastern Shore, is home to Washington College, tenth oldest college in America, the Schooner Sultana, a strong arts community, and live theater. This area is known worldwide for its beautiful Chester River, sailing, wildfowl, and agriculture. All, a short drive to four major airports, New York, Annapolis, Baltimore and Philadelphia.Additionally, Sellers are willing to contribute $10,000 toward central air conditioning upgrade.

SINGLE FAMILY HOME built just 2 years ago! Clean lines and neutral tones make this an easy move-in with nothing to do! Just across the Vintage Chester River Bridge, you will enter a charming little town that surrounds Washington College that has all sorts of new centers and places to go and things to do! The home offers a modern, open-concept layout with plenty of space and style. Large covered front porch with room for seating, plank flooring throughout the main level, lots a light and a bright kitchen equipped with stainless steel appliances and a convenient side breakfast bar. Craftsman-style doors add a touch of elegance throughout the home The spacious primary suite includes a walk-in closet, accessible through your private bathroom, providing a comfortable and functional retreat. Upper-level laundry and abundant closet space make everyday living a breeze With being so new... you should have low maintenance living for quite awhile! This one is worth a visit.