Chestertown MD Real Estate & Homes for Sale

This home is a must see! Join the Chester Harbor Community. A charming home in a lovely neighborhood on Maryland's Eastern Shore. Welcome to Chester Harbor, Queen Anne's County. Only minutes from historic Chestertown, this three bedroom, two bath home offers one-level living and an appealing owner's suite. The expansive, fully fenced backyard is easily accessed from the private deck off of the kitchen. Extend your entertaining outside! Two sheds provide outside storage for your toys, and the patio is the perfect location to enjoy those Maryland Crabs. Roundtop Park is 20 acres of outdoor fun within the community. Located at the head of Rosin Creek, you can picnic, grill, play multiple sports and enjoy the playground as you get to know your neighbors or enjoy a family reunion at the pavilion. Storage is plentiful throughout and includes a large kitchen pantry. The wood-burning fireplace sets the tone for a cozy evening, and the multiple ceiling fans bring pleasure year round. Recent updates include a new AC unit in 2021, new bedroom carpets in 2022, a new furnace in 2023, as well as new flooring in the dining room and kitchen in 2024. Don't let this one slip by, schedule your appointment today!

A sleek, thoughtfully executed renovation with clean lines and a minimalist aesthetic-sure to impress even the most discerning buyer... Located in Chestertown's coveted Mile Tree Village community, this newly updated 3-bedroom, 2-bath rancher with oversized 2-car garage features a new roof with 50-year shingles and a transferable warranty, new water and sewer lines to the street (2022), EV charger, new duct work, and more... A home that combines comfort, convenience, and peace of mind is an opportunity you don't want to miss and trust me, it won't last long!

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.

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.

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.

This gem just outside of Chestertown will be active mid-April. New HVAC, new roof, new flooring and other upgrades! Great living space with a front porch and back patio. Large backyard that overlooks beautiful farm fields. There is a one car detached insulated garage. This home offers close proximity to Rock Hall and all downtown Chestertown amenities, schools, and parks and is only 25 minutes to Middletown's shopping, dining, and entertainment options. Don't miss the opportunity to make this delightful rancher your own. Schedule a private showing today and envision the possibilities of living on the Eastern Shore!

Welcome to 100 Little Harbor Way, a charming home nestled in the desirable Chestertown community of Chester River Landing. This 2 bedroom, 2 ½ bath home offers the perfect blend of comfort and modern living and is ideal for quiet relaxation and entertaining alike. Situated in a tranquil neighborhood, you'll find yourself within easy reach of local amenities, including parks and trails, the Chester River Yacht & Country Club, the community deep water marina and yet only minutes to downtown Chestertown and Rock Hall. For those who cherish their time spent boating, there is a community marina where you will have your own PRIVATE DEEDED 30 ft boat slip (C1). This slip, which conveys with the purchase of this home, is ideally located closest to the river and is the last slip on C dock, providing easy access to all surrounding areas from the Chester River. As you approach this beautiful home, youll be greeted by a welcoming covered front porch. Once you enter the foyer, you'll be attracted to water views from many of the windows and love the spacious and open floorplan, simply flooding the home with natural light! Take special note of the gorgeous bamboo flooring, the fresh paint and new carpet found throughout the home. The spacious living room features high ceilings and a cozy fireplace, creating the perfect atmosphere for gatherings. The space seamlessly flows into the dining area and kitchen, which boasts stainless steel appliances, quartz countertops, and a fabulous kitchen island with bar seating for casual meals or allowing guests to gather around. The kitchen also includes a pantry, double ovens, gas (propane) cooking and fabulous counter space, making it easy to entertain guests. A sliding glass door off the dining room leads to the private deck, ideal for enjoying the outdoors and overlooking the peaceful neighborhood, complete with water views! This level also features a home office space with French doors, a convenient powder room and main level laundry room. The upper level is home to the spacious primary suite, which offers a peaceful retreat with a large walk-in closet and an en suite bath with modern finishes. There is an expansive deck off the primary bedroom with a spiral staircase to the lower level deck. This creates a wonderful space for intimate evenings or morning coffee while enjoying your own slice of nature! An additional well-sized bedroom and a full bath are located on this level, providing ample space for family or guests. There is a perfectly placed loft area for reading, crafting or a great second office space, if needed. The upper level family room is nothing short of phenomenal, as it can easily double as a 3rd bedroom, is beautifully suited as a TV room and could readily be used as two separate spaces because of its generous size! The community offers a variety of amenities that make this location truly special. While not a waterfront property, the home is just a short distance from the beautiful Waterfront Fire-Pit Park and the Can Shell Garden Path. Enjoy the picturesque walking paths and serene outdoor spaces, perfect for enjoying the natural beauty of the area. ** Monthly condo fees include $594.67 for the association, $41.14 for the garage, and $94.49 for the boat slip. The condo fee includes access to these wonderful amenities, and the property is conveniently located close to shopping, dining, and historical sites in Chestertown. With easy access to major routes, this home offers the perfect blend of peaceful living and convenient access to all that the area has to offer. Dont miss your chance to own this beautiful home in an exceptional location-schedule your tour today!

Welcome to 129 N. Queen Street situated in one of Historic Chestertown's most desirable and sought after locations. Nestled among multiple other restored and renovated residences, this home itself has undergone a tasteful and remarkable transformation. The entire interior has been completely renovated over the past several years utilizing many new modern materials blended with some original existing charm of days before. Upgraded features include a new open floor plan with newer HVAC, new windows, renovated kitchen featuring maple soft close dovetail cabinets, stainless steel appliances strategically situated within the butcher block and decorative concrete countertops, new refreshing tiled bathrooms, a dream laundry room, and a primary bedroom with cathedral ceiling and exposed beams. Classic old school wood floors and antique banister retain the feel of yesteryear. There is a quaint perfect sized rear yard, Three porches, a walk up attic for storage or fourth bedroom potential and much more! Don't miss out on the opportunity to be a member of Chestertown's community with a short stroll to delicious restaurants, boutique shopping, art galleries, cultural festivals/concerts and especially Downtown's renowned farmers market, all of which is just one block from the scenic Chester River!

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.

Experience the waterfront lifestyle like never before in this stunning mid-century modern home, which seamlessly hangs cliffside over the serene waters of the Chesapeake Bay's Fairlee Creek. Offering unparalleled privacy and exclusivity, this extraordinary residence evokes the sensation of floating on a boat, where every moment feels like an escape to a tranquil paradise. The unique design and architecture of this home harmoniously blend with the natural landscape, offering expansive views of the surrounding water and wildlife from nearly every room. Set on a generous almost 2-acre parcel, the property includes not only the main residence but also a second residence, making it the perfect retreat for families or guests. Together, the two homes boast five spacious bedrooms, providing ample room for relaxation and privacy. Whether youre hosting family gatherings or enjoying peaceful solitude, the expansive living areas, large windows, and open floor plans invite you to savor the beauty of the bay from within the comfort of your home. Step outside, and youll find a private beach perfect for sunbathing, swimming, or launching kayaks and paddleboards into the calm waters of Fairlee Creek. The home also includes its own private dock, offering easy access for boating enthusiasts to explore the Bays stunning waterways. For those seeking a sense of community, this property provides access to the neighboring Safe Harbor Great Oak Landing, where residents can enjoy a wealth of amenities, including a marina, pool, golf course, dining at waterfront restaurants, and a lively beach bar-ideal for casual gatherings or sunset cocktails. This home is not just a property; it's a lifestyle-a rare and exclusive opportunity to immerse yourself in the beauty and serenity of waterfront living, with all the modern conveniences and luxury amenities you could desire. Whether youre looking for a full-time residence or a vacation getaway, this mid-century modern home offers the perfect blend of style, comfort, and natural beauty.

Welcome to this move-in ready home, situated on a premium corner lot in The Village at Chestertown! This charming 1,742 square foot, two-story home offers the perfect blend of comfort and style. The inviting front porch is an ideal spot to unwind with your morning coffee, enjoy the view of the open fields, and watch the clouds drift by. Inside, the well-designed layout begins with a foyer and convenient coat closet, offering a warm welcome as you step into the spacious, open-concept family room that seamlessly connects to the dining area and kitchen. The kitchen features plenty of classic cabinetry, a peninsula island, stainless steel appliances, and a large corner pantry to keep everything organized. A private powder room and utility closet are tucked down the hall for added convenience. Upstairs, you'll find a generous owner's suite complete with a dual vanity bathroom and walk-in closet. Two additional, sizable bedrooms share a full bathroom, and there's also a nearby linen closet in the hall for extra storage. The second-floor laundry room, equipped with a washer and dryer, adds to the home's practicality. This property came with the added benefit of a Smart Home Package through ADT, offering convenience and peace of mind. The fully fenced backyard provides a safe, private space for children and pets to play, while the 8' x 10' shed is perfect for storing lawn equipment, bikes, and more. The homeowner has also upgraded the property with a 12' x 24' garage, complete with electricity and bonus features! This stunning home with well-designed architectural elevations is sited on a premium lot with views of open fields; it is just minutes from downtown Chestertown, known for its charming shops, restaurants, parks, and Washington College. This thoughtfully planned community is complete, offering a fantastic opportunity to become part of it. Dont miss your chance to make this wonderful home your own!

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.

All one floor living on quiet street with large fenced yard and mature trees close to the bay! Lovely renovations and brand new kitchen with solid white shaker cabinetry including soft close dovetailed drawers and new stainless steel appliances PLUS BRAND NEW ROOF! Brand New septic system to be installed by settlement! ABSOLUTE MUST SEE HOME!

Welcome to this beautifully updated end-unit townhouse in the heart of Chestertown! Featuring 3 bedrooms and 2.5 bathrooms, this home is fresh, bright, and ready for you to move right in. The kitchen shines with freshly painted cabinets and brand-new appliances, while new flooring throughout adds a modern touch. Enjoy the convenience of a patio out back-perfect for relaxing or entertaining. Located just minutes from town, 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!

Lovely 4 bedroom, 2 bath Cape Cod located in College Heights. The house has been freshly painted inside and out and has a new roof. Mostly wood floors throughout the house. Living room has a fireplace but the fireplace is not in working order. The kitchen/dining combo has parquet wood floors. There is a full unimproved basement that was waterproofed sometime in the past and has both inside and outside access. Hot water baseboard heat and one wall A/C unit for heating and cooling. Mostly private backyard.

**Seller is motivated and ready to make a deal - bring your offer today!** Welcome to 314 Devon Dr, Chestertown, MD 21620-an elegant 4-bedroom, 3.5-bath home offering spacious living areas and thoughtful upgrades. The grand foyer leads to a beautifully designed kitchen with a large island, perfect for cooking and entertaining. The expansive master suite features a spa-like bath with a soaking tub, separate shower, and double vanity. The fully finished basement provides additional living space, complete with a full bathroom, making it ideal for guests, a recreation area, or a home theater. Select furnishings in basement are available to convey. Outside, enjoy a fenced-in backyard with a deck leading to a patio, ideal for outdoor gatherings. Conveniently located near downtown Chestertown, this home offers easy access to shopping, dining, and waterfront activities. Schedule your showing today!

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.

HIGHFIELD, has been home to the renown architectural historian Michael Bourne and his family for almost forty-years. Mr. Bourne who authored the important Historic Houses of Kent County and guided the restorations of over 400 historic structures in the mid-Atlantic, together with his wife, Ann, created a home that reflects their deep appreciation for the refined beauty of historic architecture and preservation. HIGHFIELD, reflects the Bournes sophisticated taste and serious attention to every detail. With its steep pitch hip roof, catslide roof slope on one end, tall chimney, and enclosed front entry, HIGHFIELD is definitely reminiscent of the vernacular farmhouses of Suffolk County, England where they visited often. Outstanding historic architectural details have been incorporated throughout the house. From the Hamstone fireplace surround and hearth (actually imported from Somerset, England) in the formal Living Room, to the use of antique doors to many of the rooms fitted with both original antique and fine reproduction hardware, HIGHFIELD is a rare find! These most important details create an inviting warmth and add to its unique character. The handsome two-story, many-paned window of the Great Room faces SSE. While looking out over a stone patio and well-established perennial beds, it provides a significant amount of passive solar gain keeping energy costs low - a compliment to the six-zone heating system. As a design and practical feature, a blue enameled Lange wood stove stands proudly in the Great Room. A 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. Additionally, the first floor includes the large open Chefs Kitchen, Den/Office, Mudroom, and half-bath. 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, soaking tub, and 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, laundry room, 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.

SINGLE FAMILY HOME (tax record is incorrect) in quaint little spot in Chestertown. Nearly new, beautiful home in the quaint town surrounding Washington College. The moment you cross the vintage Chester River Bridge, it's as if you are entering a completely different world. The gorgeous little town 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. The main level features laminate plank flooring throughout and a bright, white 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 Don't miss this one!