Chestertown MD Real Estate & Homes for Sale

Almost new home in Chestertown! Modern three bed, two bath rancher with split floor plan. Open kitchen living space features LVP flooring, kitchen island, stainless steel appliances, and large windows with lots of sunlight streaming in! Come check it out today!

From the moment you drive up to this beautiful home, you are struck by the beautiful landscaping that complements the home, includes a rain garden, cutting garden, wildflower garden and a walkway that leads to an outdoor patio that provides such a great space for outdoor living. The orchard has peaches, plum, apple trees as well as berries and grapes. The enclosed screen porch overlooks the patio and provides a great space to enjoy the outdoors. There is a 2.11 additional parcel, deeded separately surrounding the property that has walking paths. Hunting is allowed, or just enjoy the beauty and solace of a forest walk. Wildlife is plentiful. Quaker Neck Landing is about 1.5 miles away on the Chester River and offers docks and a boat launch. Continuing inside, there is a covered porch at the entrance and the gracious foyer showcases the open living space that is so welcoming. The kitchen is open to the living room, the dining area, but there is a tucked away office providing another getaway area. Two bedrooms, one full bath on the main level, an amazing kitchen with all the bells and whistles, a laundry room complete with a kitchen garden window, and a screened in porch. This home offers a second level with a primary bedroom, walk in closets, additional walk in storage areas and an amazing master bath. The den/library is just waiting for you to appreciate! Improvements include a fully inspected and pumped BAT system in 2024, There is a new Trane high efficiency heat pump, a new electric water heater and a whole house Generac generator. The crawl space has been fully encapsulated and there is a dehumidifier in the crawl space. The 20x40 Amish built pole barn/garage boasts a wood working shop, two garage spaces, RV doors and tons of storage in the loft area, accessed by steps. This home with all the amenities is a must see, just minutes from Chestertown, but such a peaceful setting.

Great opportunity to own in the College Heights subdivision across from Washington College. A few improvements would make this rancher a cozy home. One level living offers a living room, kitchen, 3 bedrooms and 1 bathroom. 2 enclosed porches present additional living space for an office, family room or game room. The exterior is brick with a newer roof. The home is situated on a large, level lot, partially fenced. A $175 fee will be charged to the buyers agent at settlement. Escrow money should be 1% of the sale price or a minimum of $2,000. All offers are to be submitted online directly to prop offers. Lock box is located on the side door. Please make sure the home is locked when leaving.

Welcome to this lovely home with a detached garage in the community of Woods Edge in Kent County! The home features three spacious bedrooms with built-in closets, a full bath with dual vanities and a soaking tub, a family room with a fireplace that opens to the kitchen with appliances and wooden cabinets, and a sunroom with tiled floors and a sliding door that leads to the backyard. The home is located near the Chesapeake Bay and is just a 10-minute drive to the beaches and marina. Additionally, it is 9 minutes away from the ACME market and local restaurants.

Great investment property, currently rented with long term tenants. Located in town with schools nearby. Being sold as is, needs some tlc.

Step into this beautifully renovated 1,416 sq. ft., 2 bedrooms, 1.5 bath home in the heart of Chestertown. The building operated as the Johnson General Store into the 1950s and this home now offers the perfect blend of historical charm and modern conveniences. Fully restored in 2017 down to the studs, this home retains its rich heritage while boasting high-end updates throughout. As you enter through the front door, you'll be greeted by the original wood floors in the spacious living room that preserve the home's classic character. The fully remodeled kitchen is a chefâs dream, complete with stainless steel appliances, gas stove, and stunning quartz countertops and tile backsplash. The kitchen flows into the dining area, offering a perfect spot for both everyday meals and entertaining. Relax on the rear brick patio, a quiet sitting area where you can sip your morning coffee or unwind in the evenings. Upstairs, the primary bedroom includes a charming loft area, perfect for reading, relaxing, or creating your own personal retreat. The second-story bathroom has been thoughtfully updated with a deep soaking tub, new counters, and built-in storage, offering a spa-like experience right at home. Located in a prime in-town location, this home is within walking distance of local attractions including the farmers market, in-town events, and the Garfield Center for the Arts. Enjoy the vibrant community and convenience of being just steps away from everything Chestertown has to offer. This home is truly a rare findâcombining historical charm with modern-day amenities, and a location thatâs hard to beat. Don't miss your chance to own a piece of history! Additional photos coming soon.

Great opportunity to own a quality built home by Coldwell Builders. Larger than average lot for the community so room to grow on this one. New home features open design with large central kitchen, dining, living area and split bedroom design. Quartz counters and stainless steel appliances in the kitchen, carpet in bedrooms and LVP everywhere else. Large yard affords many uses. Community has water access with membership in the Voluntary HOA $25/year. Close to Chestertown but still in QAC public school system. MHBR #3717 Weekend Open House to be announced. Professional Pics to come.

Come check out this Modern Split Level home just built and finished in Nov 2021. This 3 bedroom 2.5 bath has tons of living & entertainment space, and a wonderful open layout. The Cathedral Ceilings, Hardwood floors, and spacious kitchen with Granite counters and Stainless appliances, many upgrades above and beyond builder grade to include shower doors, Tile in master, larger vanities, water softener, ceiling fans, bump out making for larger rooms and oversized two car garage, etc. New deck on the back of house just added. Master Bedroom with attached bath and jetted tub. Huge lower level for extra living space or bedroom. All located in a peaceful setting. Call today for more info!

This fabulous craftsman style 3 bedroom home, is perfectly situated to enjoy the beauty and tranquility of the East fork of Langford Creek/Bay with approximately 150' of shoreline and sandy beach. Great room was added in 2001, with a loft and cat walk to offer added living area. Updated kitchen in 2022 The subject property is one of 5 waterfront properties that belong in the Cacaway Farm Cooperative Housing Corporation, an exclusive farm housing community. Experience the same benefits of a fee simple ownership but share the cost of expenses. Enjoy privacy and the use of your own waterfront with sandy beach by way of a gentle slope to the water, launching kayaks or canoes while deep water slip at the community dock is also included. A south facing direction on the water side offers wonderful & welcoming breezes throughout the summer. It is improved by 2 car heated garage built in 2006 plus a smaller area for storage with a bonus area above. The area above has radiant floor heat. A BAT septic was installed in last 4 years, with a new shared sewage disposal area maintained by the county. Please do not drive down Cacaway Farm Lane without an appointment. This is a private lane.

Ranch home located in Primrose Point neighborhood( Queen Anne's County with Chestertown address), only ten minutes from downtown Chestertown. This home offers large rooms that could be modified to create a formal dining room and seperate family room if desired. The swimming pool has not been used for two years. This property is being sold "AS-IS". Sign posted.

Tucked away in a wooded setting in a quiet neighborhood just a block off the Chester River you will find this well built welcoming home. The well designed main floor layout includes a living room, dining room, and eat in kitchen plus a year round spacious sunroom overlooking the back yard and the open space beyond. This split level has the ideal arrangement with just 3 steps down to the lower level with family room, laundry room and full bath and just 9 steps up to the bedroom level with 3 bedrooms and full Jack and Jill style bath between Primary Bedroom and the hallway to the other 2 bedrooms. The home has been well maintained with recent updates including a new roof, new water heater, and an encapsulated crawl space complete with dehumidifier. Outside you will find numerous shade trees, native plantings and brick pathways that lead you through the fenced yard. There is even a chicken coop out back if you want to have fresh eggs every day! Less than a 5 minute drive to Historic downtown Chestertown with its unique shops, dining options, and numerous activities!

This charming 2-bedroom, 1-bath villa was beautifully renovated in 2020 and offers low-maintenance living on one-level. Step onto the welcoming front porch and enjoy the oversized corner lot with a fenced-in backyard, perfect for outdoor relaxation. With ample storage space and a deeded parking spot, this home is both practical and inviting. Located just 5 minutes from Rock Hall and close to the Chesapeake Bay and Tolchester Marina, this property is a fantastic opportunity in Kent County for under $200K. Don't miss out on this gem!

Beautiful cape in the coveted Mile Tree Village with a lovely in-ground pool surrounded by a spacious patio. Large flowing rooms with lots of built-ins. Half bath on the main floor. Second floor has 4 bedrooms, 2 baths, laundry, and an unfinished bonus or storage room. Home needs some finishing touches from its new owners but a little effort will yield big rewards with this property. Mature landscaping and nice hardscaping. Screened-in porch overlooking the pool and yard. 2 car attached garage.

This charming Cape Cod is situated on a desirable corner lot in Kingstown, from here you can walk or bike ride from historic Chestertown. The home features a modernized kitchen, a spacious living room, and a dining/family room, along with a convenient first-floor bedroom. The second-floor houses two additional bedrooms and a full bath. Outdoors, you can unwind on a 14 x 10 deck, set in a private backyard enclosed by a privacy fence. An oversized three-car detached garage offers approximately 900 sq ft of space, complete with a storage loft andelectricity.. Although the property has a Chestertown address, it is actually on Queen Anneâs County side of the Chester River. The area is rich with activities, including a weekly farmers market, local events, boating opportunities, dining, shopping, and access to the YMCA. Plus, it is close to Washington College, adding to the areaâs vibrant community life. Electric to Garage applied for and awaiting final permit. Seller offering $2,500 for carpet replacement

Chester River Waterfront with dock and 4-5â water depth. Enjoy sunsets and western views over the upper Chester River while having the opportunity to crab and fish from your own Dock! 5 bedroom and 3 full baths, sunroom, spacious kitchen with island, and spacious lot. Reasonably priced waterfront under $500,000.00. Great vacation home opportunity! All improvements being sold in "AS-IS" condition.

Discover your dream home perched on a tranquil hill in Chestertown, Maryland. This beautiful 3-bedroom, 2.5-bathroom residence features lush landscaping and a welcoming front porch, ideal for enjoying scenic views. Inside, the open floor plan is filled with natural light, showcasing a spacious living room with a cozy fireplace and a gourmet kitchen thatâs perfect for entertaining. The master suite offers luxury with an en-suite bathroom and walk-in closet, along with two additional bedrooms for guests or flexibility. Step outside to an expansive backyard, perfect for outdoor gatherings while taking in picturesque surroundings. This home is located in a family-friendly neighborhood with easy access to parks, shops, and dining, making it a perfect blend of suburban charm. Schedule your private showing today and experience the beauty and comfort of 126 Hilltop Drive - your future home awaits!

Now offered at $789,000, this coastal waterfront condo with expansive views of the river is located in Kent County's coveted Chester River Landing where homeowners enjoy exclusive amenities such as a private marina, community pool, fire pit, gas grills, and kayak launch. If you like entertaining, you will LOVE the spacious kitchen with LARGE center island. This turn-key unit is upgraded throughout and offers a deeded deep water boat slip, 2-car garage, and 2 covered balconies! Make the most of Downrigging weekend this year by enjoying the festivalâs fleet of Tall Ships from your very own home. A mere 3/4 mile away is Chestertown's historic downtown, host to our local speakeasy, nationally recognized farmers' & artisans' market, fine dining, walking/jogging path, eclectic shops, a plethora of activities and events throughout the year, and so much more. Summer is just around the corner and there is no better place to be than here on The Chester.

Welcome to 116 Pine Chip Road, a beautifully renovated Cape Cod in the heart of Chestertown, MD, Queen Anne's County. This 3-bedroom, 1 1/2-bathroom home has undergone a complete transformation, boasting new siding, windows, doors, and drywall throughout. The modern upgrades continue inside, where you'll find stunning LVP flooring on all three levels. The main level features two spacious bedrooms, each with double closets, and a full bathroom. The custom kitchen is a chef's dream, featuring a gas stove, upgraded quartz countertops, solid wood cabinets, and stylish open shelving. Upstairs, the primary bedroom offers a private retreat with a mini-split AC/heat unit, a large dressing room, and a convenient 1/2 bath. The finished basement is perfect for entertaining, complete with surround sound, a laundry room, and a utility room. The outdoor space is equally impressive, with a newly installed privacy fence surrounding the backyard. The fence includes three personal gates and one large gate for vehicle access. Additionally, the property features a shed and a detached garage, providing ample storage and workspace. This home is move-in ready and offers a perfect blend of modern amenities and classic charm. Don't miss the opportunity to make 116 Pine Chip Road your new home!

Welcome to your dream home in the charming sought after community of Chester Harbor! This delightful property boasts 3 spacious bedrooms and 2 full updated bathrooms, perfectly designed for comfort and modern living. Step into the huge master bedroom, perfect for all buyers. The finished basement provides versatile additional living spaceâideal for a family room, home office, or play area. The recently renovated kitchen is a culinary enthusiastâs dream, featuring contemporary finishes and high-end appliances that make meal prep a pleasure. Outside, the great yard is perfect for entertaining, gardening, or simply enjoying the serene surroundings. Enjoy the HUGE garage located in the rear of the property. Chester Harbor Community has a voluntary HOA ($30/year), which offers water access, a beach, community events, and a playground. Just around the corner is Round Top Park offering tennis, pickleball, and basket ball courts, a playground, and pavilion. Minutes from Chestertown's historic waterfront, restaurants, shopping, and marinas

Price Improvement - Welcome to this delightful brick rancher, offering over 1,500 square feet of comfortable, inviting living space. This home boasts 3 spacious bedrooms and 2 full baths, perfectly designed to accommodate a variety of lifestyles. Step inside and be greeted by the open floor plan, where the brick fireplace in the living room adds both charm and warmthâan ideal gathering spot for cozy nights. The country kitchen features a large island, separate pantry, and plenty of storage, making meal prep a breeze. At the rear of the house, youâll find the primary suiteâa private retreat with an ensuite that includes a newly updated shower. Original hardwood floors, elegant and timeless, flow throughout the home, adding warmth and character to every room. Newer windows and an encapsulated crawl space boost energy efficiency while filling the home with natural light. This home also includes a mudroom/laundry area and an attached one-car drive-thru garage for added convenienceâperfect for busy families or car enthusiasts. Additionally, the property features a separate workshop shed (18x22) with a garage door, ideal for hobbyists and extra storage. Out back, relax on the patio surrounded by mature plantings, providing a peaceful escape with scenic views of the farmland behind the home. For added convenience, the property offers a 2-car drive pad for ample guest parking, and the rear enclosed porch with heat is perfect for year-round enjoymentâa versatile space for relaxation or entertaining.

UNIQUE 4 BEDROOM/3 BATH CUSTOM BUILT CONTEMPORARY on a corner .37acre lot in the highly desirable neighborhood of Mile Tree Village. This gorgeous, meticulously maintained home offers all on one floor living in light-filled, easy care, open floor plan comfort. Features include cathedral and vaulted ceilings in the main living area and master bedroom; handsome light-toned maple flooring throughout the central living area; a glass doored corner gas fireplace in the living room; ample cabinet, pantry, storage and closet space; an oversized attached two car garage; roofed, sitably sized front and side porches; a lovely large rear patio with awning; and a custom-built stone terrace with a waterfall fountain. Additional household amenities are extensive, including like-new stainless kitchen appliances; induction cooktop and double wall ovens; a kitchen prep sink; custom granite and Corian counters in the kitchen and bathrooms, a soaking tub and glass walled walk-in shower in the Primary Bathroom ; hardwired home security and fire alarm and sprinkler systems ; a whole house generator, a surround sound system; a central vacuum system; multiple phone lines; automatic garage door; invisible fencing for pets, and the list goes on. The house has two sets of solar panels installed on the rear roof: one owned by the Sellers and the other subject to a power purchase agreement with TESLA. Both sets of panels convey with the house. Sellers are billed monthly for power generated by the TESLA owned system and receive approximately $6o/year from SOLSYSTEMS for power generated by the panels they own. Professionally maintained landscaping that includes a variety of lovely mature flowering shrubs, perennials and trees and an in-ground watering system surround the house. A trim lockable garden shed sited in a wooded area at the back of the house provides out of the way storage for lawn mowers and garden equipment and supplies. In addition to its many on-site pluses, this wonderful home offers convenient, quick and easy access to Washington college, area schools, parks, doctors, churches, Historic downtown Chestertown, waterfront recreational facilities and shopping centers. MOTIVATED OWNERS!

Charming house in Country Club Estates. Located on the 14th hole with views of the Chester River. 3 beds and 2.5 baths. Potential for a 4th bedroom and potential for a first-floor bedroom. Lovely landscaping and cedar shake roof. Traditional floorplan. Beautiful wood floors throughout. Screened in porch and lovely brick patio. The perfect blend of classic architecture and modern convenience. Close to downtown historic Chestertown. This would be an amazing place to call home.

Nestled in a prime suburban commercial zone, this versatile property offers 1,300 sq ft of living space, perfect for both residential and/or commercial use. The freshly resealed driveway accommodates up to 6+ vehicles, with the potential for parking lot expansion, ensuring ample space for guests or clients. The property features two inviting front entries: one through an 8x16 sunporch, ideal for enjoying morning coffee or greeting visitors, and another through the welcoming living room with a large bay window that floods the space with natural light. The rear entry provides convenient access to the kitchen and basement. The kitchen is equipped with all essential appliances and features laminate countertops and durable vinyl flooring. A pass-through window connects the kitchen to the sunroom, enhancing the open and airy feel of the building. The basement, with its poured concrete floor and perimeter trench leading to the sump pump, offers potential for additional storage or workspace. The single level structure includes a spacious full bath and three generously sized bedrooms, perfect for a family or for converting into office spaces. This property blends functionality and charm, making it a unique opportunity for those looking to live and work in a suburban setting.

Built in 2005, this like-new home boasts an open floor plan with inviting, bright spaces. The residence features 3 bedrooms, 2.5 bathrooms, and 1,222 square feet of low-maintenance living. Enjoy the convenience of two dedicated parking spots right in front of the home, as well as no outside maintenance. The half bath comes equipped with a stacked washer and dryer for added ease. The spacious living room and dining room seamlessly flow to a sliding door that opens to a rear porch and common grounds, perfect for relaxing or entertaining. Located in Chestertown, this home is in close proximity to Washington College, Chester River Hospital Center, and the Chestertown walking trail, making it an ideal location for both convenience and leisure.

Charming Historic Chestertown investment opportunity! Once updated this building can accommodate two street-front shops and a spacious apartment upstairs. The back of the building has extra living space with a private entrance and full bathroom. The attic is flooded with natural light! One could use the attic as-is for extra storage, or it could be renovated, adding additional living space. Back deck overlooks sweet courtyard, perfect for relaxing. GREAT location and tons of character - enjoy the Chestertown Farmer's Market year round, the Chester River just a few blocks away, shops and restaurants right down the street - you cannot beat this Historic District location and opportunity. Seller has removed plaster walls downstairs and updated the electric. Other updates include: exterior painting, new metal roof and a new deck with entry to second floor apartment.