Chestertown MD Real Estate & Homes for Sale

Adorable and Affordable in Chester Harbor community! This 4-bedroom 2 bath home is ready for you! situated on a .8-acre level lot that backs to trees and open fields, this home offers a private retreat in a sought-after Water oriented community. There is a large Country Kitchen with room for table and chairs. Laundry in Kitchen is convenient and easy to access. Main level has two bedrooms and 2 baths while the finished lower level offers plenty of space and 2 bedrooms. Come and enjoy the tranquil and walkable neighborhood that is close to Chestertown and offers Queen Annes County Schools!

An adorable cottage with water views of the Chester River! Nicely maintained cottage featuring 3 bedrooms, 2 full baths with all the big ticket items completed. Newer Well and Septic, HVAC and newer Metal Roof just leaves you with finishing touches on the interior as you see fit. Currently used as a rental. Also features a detached workshop and detached garage. If you are a boater, bring your boat and the Deep Landing Boat Ramp is just minutes away . Very affordable home in our area, don't wait on this one!

Built in 2005, this beautifully maintained home offers modern comforts and an inviting atmosphere. The open floor plan on the main level features bright, airy spaces that seamlessly connect to a charming brick patio via sliding glass doors. With 3 bedrooms, 2.5 bathrooms, and 1,222 square feet of low-maintenance living, this home is designed for ease and comfort. Enjoy the convenience of two dedicated parking spaces right at your doorstep and the peace of mind that comes with no outdoor upkeep. The spacious living and dining areas flow effortlessly to the rear porch and shared common grounds, creating the perfect setting for relaxation or entertaining. Nestled in Chestertown, this home is ideally located near Washington College, Chester River Hospital Center, and the Chestertown walking trail, offering easy access to both local amenities and recreational opportunities.

This meticulously maintained 3-bedroom, 2-bathroom ranch-style home offers the perfect blend of comfort and modern features. Located in a tranquil setting that backs to farmland, it boasts an open floor plan with cathedral ceilings, creating a spacious and airy atmosphere throughout. The upgraded kitchen with stainless steel appliances that make it ideal for both cooking and entertaining. The upgraded flooring adds elegance and durability to the home, while the energy-efficient tankless water heater ensures a continuous supply of hot water. Whether you're relaxing in the living area, enjoying the views of the surrounding farmland, or hosting guest in the open space, this home is designed for modern living. It's truly a must-see for anyone seeking a move-in ready home. 1 acre lot

Welcome to Chester Harbor - a family oriented place to live! The Chester Harbor Community has a voluntary HOA of $30/year, which offers water access, a beach, community events, and a playground. Close by is Round Top Park offering tennis, pickleball, and basketball courts, a playground, and a pavilion. Minutes from Chestertown's historic waterfront, restaurants, shopping, and marinas. Queen Annes County Schools! Comfortable serene and convenient - this well cared for home has hardwood floors and a new hot water heater and water tank on 3/11/2023 and an attached workshop!

Brand New Gorgeous Custom Home ready in December. Fall in love with the 1st floor bedroom/bath/WIC, 2 car garage, gourmet kitchen with large island, cathedral ceilings, huge family room, 1st floor laundry, front porch, sky-basement on 2nd floor for storage, 2 large bedrooms and full bath on second floor. This great floor plan is hard to find with all of these upgrades and is perfectly situated on an acre lot in a beautiful country setting. Relax and watch the sun rise or set as you boast to your family & friends about this amazing house you just bought. Professional pictures coming soon! Won't last long! Co-owner/RE agent.

This home is located on a quiet Cul-de-sac in a water access community of Chester Harbor on the Queen Anne's side of the Chester River. Recent improvements include, fresh paint, new carpet on the second level, dry lock on basement walls, sunroom being improved with new windows, water heater to be installed, and newer roof with the garage roof installed in 2024. Main floor has wood floors, brick fireplace in Living room with wood stove insert, eat in kitchen, dining room, den/office and full bath. Second floor has three good sized bedrooms and full hall bath. Primary bedroom has plenty of closet space including a cedar closet. Full unfinished basement houses the washer and dryer. Backyard has ample space for the play, pets and outdoor entertaining on the brick patio. The attached garage provides parking for two and additional storge above. Professional photos to be uploaded soon.

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

Rare end unit townhome in Oak Hollow. Close to shopping and college. Spacious rooms. Open kitchen with granite counters and a kitchen island. Sliders to patio and to upper level deck. Large yard. Half bath on the main floor. 3 bedrooms and 2 full baths on the upper floor. Family room in the basement as well as an oversized 1 car garage with lots of storage. Roof has recently been replaced. Overall, a great unit in a great location!

This charming 3-bedroom, 2-bath rancher nestled in a serene setting of Quaker Estates is a gem you won't want to miss! This modern 2018 home offers a perfect blend of comfort and style on a back corner lot with scenic trees on two sides. The perfect split bedroom design with large open central living room, kitchen, and dining with generous space perfect for gatherings. Durable vinyl laminate flooring with the exception of the two smaller bedrooms are carpet. The primary bedroom is a peaceful retreat with an en-suite bathroom, offering privacy and convenience. Enjoy time outside on the expansive 16 x 32 deck for outdoor gatherings and relaxation. Two nice storage sheds for your lawnmower and tools, raised garden bed, play area and a separate spot for your camper. This home shows like new and won't last long. This home offers close proximity to all downtown 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 in this beautiful home! Private well and public sewer.

Welcome to your serene getaway nestled on 2.62 acres of partially wooded land on Urieville Lake! This stunning 4-bedroom, 3.5-bathroom home offers the perfect blend of comfort and privacy, making it an ideal retreat for families and nature enthusiasts alike. With an option of a first floor bedroom there are currently three bedrooms on the second floor and one unofficial bedroom in the basement, thereâs plenty of space for family and guests. The open-concept living area is perfect for gatherings, featuring ample natural light and gorgeous views of the surrounding landscape & lake! Enjoy convenience and comfort with two full bathrooms on the second, one full bath on the lower level and an additional half bath on the first, designed with modern fixtures and finishes. The finished walk-out basement provides excellent additional living space, bath/bedroom & perfect for a game room, entertainment area, or a private office. It also offers direct access to the beautiful outdoors. The property spans 2.62 acres, providing ample room for outdoor activities, gardening, or simply unwinding in nature. The partially wooded area enhances your privacy while allowing for serene nature walks right in your backyard & along the Lakes edge! Located on Urieville Lake, enjoy fishing, boating, and other recreational activities just moments from your doorstep. This private setting is perfect for those looking to escape the hustle and bustle of city life. Urieville Lake is about 35 acres in size and is shaped like the letter Y. The average depth is about 3 feet and supports a standard bass/bluegill fishery and is managed accordingly. Anglers may also occasionally catch other species including pumpkinseed sunfish, brown bullhead catfish, golden shiners and common carp. Interior pictures and layout coming soon!

Nestled on 10 scenic acres just outside of Chestertown, this spacious 3,280 sq ft home offers incredible potential for those looking to earn a little sweat equity. This home is ready for a buyer looking to uncover its true potential. Boasting 3 large bedrooms, a very large room on 2nd level could be a bedroom ? game room ? you decide, 3 flexible spaces that can be used as offices, dens, or multi-purpose rooms, and oversized rooms throughout that offer endless possibilities for customization. Rich hardwood floors and custom doors and woodwork add character and charm, while a full-length sunroom across the front of the house provides stunning views of the surrounding landscape. The spacious kitchen features Amish-built cabinetry, offering both craftsmanship and timeless appeal, along with a large pantry for added storage. The generously sized laundry room offers added convenience. There is so much storage space offered throughout this home. walk in closets, etc. The property includes an outdoor wood furnace (central boiler system), a whole-house propane generator, a shed, large circular driveway and several outbuildings one with small studio space providing ample space for storage, workshops, or hobbies. There is also future development potential with upcoming zoning changes from Rural Character to Community Residential - think subdivision . Please verify all zoning and development opportunities directly with the County. This is a unique opportunity to invest in a property with endless potentialâ??whether you're looking for a personal retreat , a large piece of land to call your own, or a long-great investment. Donâ??t miss your chance to make this property your own! Home is being sold AS IS.

This impeccably maintained home is a true standout and has it ALL! With 5 spacious bedrooms - with both main level & upper level primary suites - and 3.5 baths, including a main level primary suite with a walk-in closet featuring a premium wood built-in system, dual vanity, and a double-headed walk-in tiled shower. This home offers both luxury and convenience. The updated kitchen is an ideal space, with granite countertops, stainless steel appliances, a stylish tile backsplash, and 2015 KraftMaid cabinetry in a stunning navy blue. Every room is thoughtfully painted and wallpapered, adding character to the gleaming hardwood floors and plush, high-quality carpets throughout. The home also boasts an updated HVAC system and a brand new asphalt driveway. The finished basement includes a rec room and ample storage space, while the expansive 0.8-acre lot overlooks serene pastoral farmland, with a beautiful hardscaped patio perfect for outdoor entertaining. Best of all, this home is located under 1.5 miles from the heart of downtown Chestertown, so youâre just minutes away from shopping, dining, and all the charm the town has to offer.

A highly coveted Chester River waterfront just minutes from Historic Downtown Chestertown. This large home has an ample sunroom overlooking the yard to the Riverfront, an in-ground pool within the 100' buffer, a dock with 3+ MLW, an expansive primary suite with sweeping water views, a private space for a home office, playroom, or in-law suite, and a detached three car garage for toys, vehicles, and storage. All situated on almost one full acre. Brand new upgrades since Sept '24 include central AC, roof, refinished hardwood floors, and paint throughout. With easy access to Morgnec Rd, Rt. 301 is only 12 minutes away... which leaves you only an hour's drive from Wilmington, DE or Philadelphia, PA. And into the heart of NYC in less than three hours. Escape to the Eastern Shore lifestyle!

Welcome home this beautiful end unit townhome in the newer community of The Village At Chestertown. This 3 bedroom, 2.5 bath townhome looks out over the beautiful pond with fountain, and a great walking path around the pond and community. Furry friends are welcome at the nearby dog park as well. This home is less than a year old and has had some upgrades added since the purchase, such as the maintenance free fully fenced back yard, ceiling fans, upgraded light fixtures, upgraded bathroom vanities, kitchen faucet, hardware, and more! Easy commute to Rt. 301, and the brand new YMCA is right around the corner! Enjoy Chestertown with it's small town charm, great restaurants, artistic venues, and close to Washington College. Schedule your tour today!

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

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.

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!

Exciting Price Improvement Reduced $10,000 plus Seller to install new carpet. 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. Garage has newly installed electric.

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!

CUSTOM - BUILT 4 BEDROOM/3 BATH CUSTOM BUILT CONTEMPORARY on a corner .37acre lot in the desirable neighborhood of Mile Tree Village. This gorgeous, meticulously maintained home offers all on one floor living in light-filled open floor plan comfort. Features include cathedral and vaulted ceilings in the main living area and master bedroom; handsome maple flooring throughout the central living area; a remote controlled 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 large rear patio with automated awning; and a custom-built stone terrace with a waterfall fountain. Additional household amenities include 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/fire alarm and sprinkler systems ; Generac generator, surround sound system; 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. Professionally maintained landscaping that includes mature flowering shrubs, perennials and trees and an in-ground watering system surround the house. A lockable garden shed sited in a wooded area at the back of the house provides out of the way storage for lawn 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. If you're looking for exceptional comfort and convenience, look no further!

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.

Welcome to your private oasis! This charming home boasts mature landscaping that provides both beauty and privacy on a large corner lot. . Custom built Cape Cod offers a first floor primary suite, living room with fireplace and built ins, formal dining room and a kitchen with granite counters and updated appliances. Thereâs an open area on the 2nd level ideal for reading or watching TV. Plus 2 more bedrooms and an office. Enjoy the serene ambiance from the large deck, overlooking a picturesque pond with not one, but two enchanting waterfalls. The soothing sound of cascading water creates a tranquil atmosphere, perfect for relaxation and unwinding. This property is a true retreat, offering an idyllic escape right in your backyard. Located just minutes from the Chester River and Chestertownâs historic district.

Spec home located in small 12 home development (to be built). Prestwick offers the best in eastern shore living with the small town charm of Chestertown, MD, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington, DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board or kayak at the new town marina or the many county owned ramps. Design and build the home you want with one of the area's finest builders