Chestertown MD Real Estate & Homes for Sale

Nestled in the water-access community of Chesapeake Landing, this charming Cape Cod-style home offers a perfect blend of classic character and modern comfort. With over 2,100 square feet of finished living space, the home features four spacious bedrooms and three full bathrooms, ideal for flexible living arrangements. Inside, youll find a freshly painted bright and open layout with beautiful bamboo flooring, a thoughtfully designed kitchen with durable Meganite countertops, brand new stainless steel appliances, and updated mechanical systems including a high-efficiency water heater and forced-air heat pump for year-round comfort. The main level provides easy access with a bedroom and full bath, offering convenience for guests or multi-generational living. Outside, the property has been enhanced with fresh landscaping and a brand-new gravel driveway, creating an inviting first impression. The private deck overlooks nearly an acre of serene, wooded surroundings, offering a peaceful retreat. Residents of Chesapeake Landing enjoy access to community water privileges, including a boat ramp and dock-perfect for those who love to spend time on the water. With no town taxes, a low annual HOA fee, and just a short drive to historic downtown Chestertown, this home is a wonderful opportunity to enjoy the best of Eastern Shore living.

Charming Rancher with Private Backyard Oasis in Byford Estates-Dont miss your opportunity to own this beautifully maintained ranch-style home tucked within the highly sought-after neighborhood of Byford Estates-just a short stroll to historic downtown Chestertown! With 3 spacious bedrooms, 2 full baths, and multiple living spaces, this property offers comfort, privacy, and the kind of charm thats hard to find. Inside you will discover sun-filled interiors, gleaming hardwood floors, and custom built-ins that add both character and functionality. The home flows effortlessly with a traditional yet open feel, featuring a formal dining area, a cozy breakfast room, and a welcoming living room. A bonus room off the primary suite is perfect for a home office, studio, or quiet reading nook. Enjoy the peaceful privacy of your professionally landscaped backyard, a true oasis with travertine pavers, lush native Maryland plantings, and an inground pool-ideal for entertaining or unwinding in solitude. The only known Katsura tree in Chestertown adds a touch of rarity and beauty to this one-of-a-kind property. The primary suite is your personal retreat with a walk-in closet, ensuite, and serene backyard views. On the opposite wing of the home, two additional bedrooms and a full bath offer separation and comfort for guests or family members. With three separate entrances to the rear patio, theres a natural indoor-outdoor flow perfect for gatherings. Upgrades include a 40-year architectural shingle roof, newer HVAC system with a 10 year warranty, a meticulously landscaped backyard custom designed to offer low maintenance for lasting appeal. Located within walking distance to downtown Chestertown where you can enjoy the nationally acclaimed Farmers Market, Walking Trails, Parks, Boutique Shops, Restaurants, Entertainment and of course the Chester River. Don't miss your opportunity, schedule a showing today!

Gently used 2 bedroom townhome in sought after Tolchester Village! Features a terrific open kitchen with all major appliances, nice living room/dining room combination with a slider to the patio. Bedrooms are good sized and have vaulted ceilings! Tolchester Village is a quaint community that underwent a complete renovation in 2021. Public water and sewer! Thoughtfully remodeled and it shows like new! Common areas include a playground. Affordable, beautiful, and low maintenance!! What could be better?

Why settle for outdated or overpriced when you can own brand-new construction in a waterfront community just minutes from historic Chestertown? This 3-bed, 2.5-bath Cape Cod in Chesapeake Landing is designed for easy, elegant living-featuring an open floor plan, main-level primary suite with walk-in closet and attached bath, and luxe finishes throughout. Enjoy luxury vinyl plank flooring, granite counters, white shaker cabinets, and stainless steel appliances. Upstairs offers two oversized bedrooms and a full bath-perfect for guests or family. Located in a water-access community with walking trails and clubhouse. Just minutes to marinas, waterfront dining, and Chestertowns vibrant downtown with its shops, galleries, cafes, farmers market, and historic charm. No renovations, no compromises-just move in and enjoy the lifestyle you deserve.

Welcome to this cute-as-a-button home in the water-access community of Chester Harbor! Whether you're starting out, downsizing, or simply looking to simplify your lifestyle, this move-in ready gem offers the perfect balance of comfort, convenience, and charm. Set on a spacious third of an acre lot, this home offers just the right amount of space-three bedrooms, one full bath, and room to grow both inside and out. Recent updates over the past few years take the worry out of homeownership: enjoy low maintenance living with newer flooring throughout, a durable and stylish metal standing seam roof, a generously sized HVAC system for year-round comfort, and freshly sealed asphalt driveway. Step out back to a deck thats just calling for summer barbecues, crab feasts, or quiet evenings under the stars. A large two-bay shed with electric is the perfect place to store tools, bikes, or gear for all your hobbies. The manageable yard offers green space without hours of upkeep-ideal for pets, gardening, or a game of catch. Located just minutes from downtown Chestertown, shops, restaurants, and the water, this home blends quiet community living with everyday convenience. Best of all, there's no HOA-giving you flexibility and freedom without extra fees. Dont miss this opportunity to own your own home in a well-loved neighborhood at an approachable price point. Low maintenance, move-in ready, and full of potential-this is the one you've been waiting for!

Nestled in the tranquil Chesapeake Landing community. This large three bedroom, two bathroom contemporary rancher offers 1978 square feet of comfortable one-level living. This home is situated on a 0.33 acre corner lot with direct access to Worton Creek, minutes from downtown Chestertown. It has an open -concept floor plan with cathedral ceilings. Many upgrades have been done to this house since purchasing. Enjoy the spacious backyard with a fenced in yard.

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.

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!

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. Investors this property could possibly make a great Airbnb property to add to the portfolio. 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.

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.

$20,000 Price Reduction! 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. Seller Financing is available if needed.

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!

Pricing reflects the property fully finished and professionally cleaned. This is a rare chance to own a completely restored Second Empire home on Chestertown Historic Districts most prominent corner. Water views are appreciated from two sides. Great balance of modern amenities and layout matched with historic design elements and style. The builders who took on this passion project are some of the most renowned in Kent County. 30-60 day estimated timeframe to complete upon contract acceptance. The detached garage is a huge plus with highly sought after off street parking.

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.