Chestertown MD Real Estate & Homes for Sale

Lovely all one floor living in quiet neighborhood with updated features throughout! Brand new gorgeous kitchen with white shaker cabinetry featuring dovetail construction soft close drawers, solid butcher block countertops, tile backsplash, large island, brand new stainless steel appliances and much more! eng hardwood flooring, recessed lighting, vertical custom ship lap, gas fireplace, screened porch opportunity and much much more! ABSOLUTE MUST SEE MOVE IN READY HOME!

Welcome to 10705 Millbrook Drive, a charming Cape Cod-style home located in the desirable Chesapeake Landing community. This 3-bedroom, 2-bathroom residence offers comfortable living with modern updates, including bamboo flooring and a high-efficiency water heater. The open floor plan is perfect for entertaining, with a spacious living area and well-appointed kitchen featuring Meganite countertops. Enjoy the tranquility of the surrounding area from the private deck, or take advantage of the community amenities, including a boat ramp, dock, and water privileges. The home also features a basement with a sump pump, a gravel driveway for off-street parking, and a private well and septic system. Just minutes from the heart of Chestertown, this home is a perfect blend of convenience, comfort, and nature.

Prime Investment Opportunity in Chestertown with Leases In Place!!! This duplex property offers versatility, upgrades, and endless potential in a central Chestertown location. Conveniently situated across from Kent Plaza Shopping Center, near Washington College, and just minutes from the YMCA. This property is perfect for live-in owners, investors, or those seeking multi-use functionality .Excellent potential for a home business, in-law suite, or rental income from one or both units! With a prime location, countless upgrades, and flexibility, this diamond in the rough is ready to shine. Don't miss the opportunity to make it yours! Unit A: Bright & Spacious 2 Bed / 1 Bath This well-appointed 2-bedroom unit offers a comfortable and inviting living space. Large Living Room Area Updated kitchen with new Vinyl flooring and fixtures, perfect for cooking and separate Dining area. Convenient in-unit laundry with a stackable washer/dryer to simplify daily life. Refinished oak floors complemented by new ceiling fans, faucets, lights, receptacles and Freshly Painted for a polished look. Recently upgraded bathroom featuring Vinyl floor and a fresh design. Dedicated front parking for convenient and private access. Unit B: Modern 1 Bath Studio with Private Access This updated studio unit is ideal for a tenant seeking comfort, privacy, and convenience. With thoughtful renovations and modern upgrades. Private parking area with a safety light for added security and convenience. Dedicated side entrance featuring a new porch with safety rails and a durable cement base. Vinyl flooring throughout for a fresh and modern feel. Fully renovated kitchenette and bathroom, providing all the essentials in a sleek design. Exterior Highlights Newly installed apron driveway allows for seamless in-and-out access and parking around the house. Regraded landscaping with underground drainage ensures quick water management. New siding, trim, and gutter-guard gutters offer low-maintenance protection. Dependable pest/termite policy transferable to the new owner. Shed for additional storage Septic pumped and Well sealed in January 2025 for peace of mind. Registered with separate addresses for county emergency services. A wall divides the units but includes an existing door for easy conversion back to a single-family home if desired. Excellent potential for a home business, in-law suite, or rental income from one or both units!

Nestled along the tranquil western shore of the Chester River, this beautiful townhome in Chester River Landing offers an unparalleled waterfront living experience with direct water access and captivating water views. Just a short stroll from the historic heart of Chestertown, MD, it combines modern luxury with timeless charm. This elegant 3-bedroom, 2.5-bath residence is designed to maximize comfort and style. The spacious living areas are bathed in natural light, enhancing the serene ambiance of this waterfront haven. The open-plan living and dining areas flow seamlessly into the well-appointed kitchen, equipped with top-of-the-line appliances and ample storage. The master bedroom is a true retreat, with easterly river views and an ensuite bath. The additional bedrooms are generously sized, perfect for family or guests. The 3.5 baths are elegantly designed, featuring modern fixtures and finishes. One of the standout features of this home is its perfect vantage point for watching the daily sunrise. Imagine starting your day with a cup of coffee on the balcony, as the first light of dawn reflects off the calm waters of the Chester River while rowing teams begin their daily workout. Whether you're seeking a peaceful waterfront retreat or a picturesque spot to entertain, this townhome offers it all. The community amenities of Chester River Landing further enhance the lifestyle, with walking paths, swimming pool, private pier with available boat slips for purchase or lease, outdoor grilling and beautifully landscaped common areas. Discover the unique blend of history, luxury, and natural beauty at this waterfront home on the Chester River.

Discover the perfect blend of modern design and rustic charm at 204 Pine Cove Lane, a stunning 3-bedroom, 2.5-bathroom home built in 2021. Tucked away on a secluded lot and surrounded by picturesque farmland, this property offers unparalleled privacy and tranquilityâ??a true sanctuary for those seeking a peaceful retreat. Step inside to be greeted by a thoughtfully designed interior, featuring sleek, contemporary finishes and an open-concept layout that effortlessly combines style and functionality. Expansive windows frame the idyllic countryside views, filling the home with natural light and creating a warm, inviting atmosphere. Situated just minutes from Chestertownâ??s historic downtown, with its charming shops, restaurants, and waterfront attractions, this home perfectly balances rural serenity with modern convenience. Experience the beauty of country living with all the modern comforts you desire at 204 Pine Cove Laneâ??a home where every day feels like a retreat.

Charming, very well-maintained home located just outside historic Chestertown. The side entrance has a spacious deck and ramp that leads to a full blacktop driveway. Unique split level back entrance. 1.3 grassy acres. Large unfinished basement for extra living space. Hardwood flooring beneath the carpet. Updates include recent paint in interior rooms, (except Kitchen), new paint basement, new lumber on flat deck, washer and dryer, survey, new back door and storm door, new screen/storm door - front, purchased propane tank, new Bryant inverter heat pump, new roof, new Purfect water system, basement dehumidifier, new sump pumps and water discharge and alarm system. Move in condition!

Welcome to 105 Justin Buch Drive, a delightful single-family home nestled in a quiet community on the Queen Anne's side of Chestertown, MD. This charming residence offers 3 spacious bedrooms and 2 full bathrooms, providing ample space for comfortable living. Buy with ease with this recently renovated home within the last 3 years, to include a new roof, HVAC, Kitchen backsplash, new garage door, new 20x12 maintenence free deck, landscaping, Vapor barrier and more, all situated on a large lot just under an acre. Located in a peaceful neighborhood, this home is just a short drive from downtown Chestertown, where you can enjoy local shops, restaurants, the Chester River attractions and more. With its blend of comfort, convenience, and charm, 105 Justin Buch Drive is the perfect place to call home. Don't miss out on this wonderful opportunity! Contact us today to schedule a viewing. Sellers have found their home of choice and are motivated!

Welcome to this charming 3-bedroom, 2-bathroom rancher, offering the perfect blend of comfort and convenience with one-level living in the desirable Chester Harbor community. Set on a spacious .76-acre lot on the Queen Anne's side of the Chester River, this home is ideally situated in a water-oriented neighborhood, perfect for boating enthusiasts and nature lovers alike. The home boasts a large primary bedroom with its own private bath and an impressive walk-in closet, which includes a cedar section for added storage and warmth. The kitchen and dining area, featuring newer flooring (installed just two years ago), create a modern, inviting space for meals and family gatherings. The kitchen is equipped with updated appliances, ensuring a functional and stylish area for cooking. Outside, the fenced yardâ??perfect for both kids (two- or four-legged)â??provides a safe and spacious environment to play and explore. The fence, installed just four years ago, adds a secure touch to the property. Additionally, the detached two-car garage offers ample storage for vehicles, tools, or water toys.

Come By this brand new Cape Cod nestled in charming Pear Tree Point! This 3-bedroom, 3-bathroom haven offers the tranquility of coastal living with the ease of new construction. Step inside and discover the warmth of this open floor plan luxury vinyl plank flooring flowing throughout the main level. Unwind in the light-filled living area, perfect for entertaining, or retreat to the inviting main-floor primary bedroom suite, designed for ultimate relaxation. This private sanctuary boasts an attached bathroom with modern fixtures and finishes, and spacious walk-in closets. Unleash your inner chef in the stunning kitchen, featuring stylish shaker cabinets, gleaming granite countertops, and a suite of stainless-steel appliances. Extend your living space onto the expansive patio, perfect for al fresco dining or simply soaking up the tranquility of your waterfront surroundings. Modern finishes throughout and ample storage space completes this lovely home. But the best part? Pear Tree Point offers a vibrant community atmosphere with water access, marinas, and nearby parks. Don't miss this opportunity to own a brand-new oriented haven! Contact us today to schedule your private showing .****Special Discounted Financing in available for this home, with rates are available**** Contact for details, rates subject to change, subject to loan qualification.

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 spaceâ??ideal for a family room, home office, or play area. The recently renovated kitchen is a culinary enthusiastâ??s 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

Need additional space, no problem! This home has a sunken den with a brick wood fireplace off the main living room that could be used as an office and a humongous 23â??8 X 18â??4 family room currently used as the Billards room hosting a 9ft pool table/gym off the kitchen/dinning room that was added in 2021! This room is great for entertaining & hosting large parties and could be a fantastic place to have a daycare! A voluntary HOA allows access to the communities private beach, dock and playground all located on Rosin Creek with access to the Chester River! Va loan has an assemble low interest rate for those who qualify for VA!

Welcome to Chester Harbor. Great starter or downsizer, 3 bed 2 bath rancher awaits new owners. The floor plan includes generous Eat -in kitchen and large living room, separate laundry, and a huge screened in porch for picking crabs, parties, or just relaxing. New flooring , fresh paint, and new kitchen counters are a few of the recent updates. Tree lined rear yard and front holly hedge provide surprising privacy. Close to Historic Chestertown and many local points of interest. Easy drive to tax free DE shopping. Voluntary HOA is $25 a year and provides for community water access and park privileges. Shed is " AS IS".

Discover serenity in this charming 2-bedroom, 2-bath oasis with 1,272 sq ft of living space. Nestled in the Chesapeake Landing community, enjoy proximity to Worton Creek's stunning views and easy access to the Chesapeake Bay. This home boasts enchanting features, including a captivating spiral staircase and elegant galvanized tray ceilings that enhance the vibrant, light-filled living area. Relax on the easterly front porch or open side deck, surrounded by nature's beauty and wildlife. With a fully encapsulated crawlspace, tankless hot water heater, and a well-equipped kitchen, this home is truly move-in ready for your peaceful Eastern Shore retreat.

Brick rancher located on the corner of Greenwood and Glen Street in College Heights offers a large screened porch, eat-in kitchen and dining room. Home is convenient to downtown historic Chestertown , Washington College and hospital. Property is served with public water/sewer. Underground oil tank has been removed and the crawlspace is encapsulated.

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! Back on the market at no fault of the seller! Schedule your showing today!

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 completed & ready for a family to start their next adventure. Fall in love with the 1st floor bedroom/bath/WIC, 2 car garage, gourmet kitchen with large island & granite counters, 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. Great country location near the Chester River, boat ramps, beaches, parks, hospitals, restaurants, shopping. Convenient to the beaches, Dover, Middletown, Annapolis & DC/Balt. Co-owner/RE agent. All reasonable offers considered although priced to sell.

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, thereâ??s 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!

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 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 youâ??re 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 to 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!

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.

**Exclusive Waterfront Craftsman Home with Sandy Beach â?? A Rare Opportunity** Nestled on the serene East Fork of Langford Creek/Bay, this stunning 3-bedroom Craftsman- style home offers the perfect blend of comfort, privacy, and natural beauty. With approximately 150 feet of shoreline and a sandy beach, this property is a true waterfront gem. **Key Features:** - **Spacious Great Room**: Added in 2001, the great room boasts expansive living space with vaulted ceilings, a loft, and a catwalk for a unique and inviting atmosphere. - **Updated Kitchen**: In 2022, the kitchen was beautifully remodeled to include modern finishes and appliances, making it the perfect space for entertaining. - **Exclusive Community**: Located within the Cacaway Farm Cooperative Housing Corporation, this home is part of a select group of 5 waterfront properties. Enjoy ownership in a corporation with the added benefit of sharing common expenses for a lower cost of living. - **Private Waterfront**: A gentle slope leads you to your own piece of paradise with a sandy beach, ideal for launching kayaks or canoes. Plus, the deep-water slip at the community dock provides the perfect spot for boat owners. - **South-Facing Exposure**: Enjoy breathtaking water views and refreshing summer breezes from your south-facing waterfront. - **Heated Garage & Bonus Area**: The property includes a 2-car heated garage, built in 2006, with a separate storage area and a bonus space aboveâ??complete with radiant floor heat for year- round comfort. - **Modern Infrastructure**: A new BAT septic system was installed in the past 4 years, and the shared sewage disposal area is maintained by the county for worry-free living. This property offers the rare combination of privacy, community, and stunning waterfront access. Don't miss out on this incredible opportunity to own a piece of paradise. The south-facing orientation of the property offers a natural advantage when it comes to the climate and the breezes that sweep across the waterfront. Because of its position, the home is perfectly situated to catch the prevailing summer winds from the south, which are often cool and refreshing. These gentle breezes help to moderate the temperature, creating a comfortable, airy atmosphere throughout the warmer months. Whether you're relaxing on the deck, enjoying the beach, or sitting inside with the windows open, the breezes will bring a pleasant, natural ventilation, keeping things cool and comfortable even on the hottest days. The south-facing exposure also ensures you have plenty of sunshine throughout the day, adding to the overall warmth and welcoming feel of the space. This combination of sunlight and breeze provides a wonderful outdoor living experience, whether youâ??re lounging on the waterfront or enjoying an evening dinner on the deck with the gentle breeze in the air. Itâ??s the kind of peaceful, tranquil environment that enhances the feeling of living in harmony with nature. **Please note**: Cacaway Farm Lane is a private road, so appointments are required to view the property. Schedule a showing today and make this dream home yours!

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!