**MOTIVATED SELLERS, BRING ALL OFFERS** Situated on a generous 0.653-acre lot just outside of Chestertown, this property offers the best of both worlds—proximity to town amenities with the added benefit of space and privacy. This well-maintained home features 3 bedrooms and 2.5 bathrooms, including two recently updated baths. The interior boasts a welcoming entryway, formal dining room, and a spacious kitchen equipped with an island, gas cooktop, and a cozy breakfast nook. You'll also find a dedicated laundry room with a convenient side entrance. Flooring throughout the home includes a mix of wood, tile, and carpet, while the living room offers a comfortable gathering space anchored by a working fireplace. Step outside to enjoy the expansive backyard, perfect for entertaining or relaxing. The detached two-car garage includes an additional space ideal for a workshop or home office, plus a loft area with endless possibilities. Don't miss this opportunity to enjoy country-style living just minutes from downtown Chestertown!
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 Encapsulated Crawl Space, 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 an upgraded insulation package with Delmarva Power - approved improvements - qualifies under current 2025 energy efficiency guidelines... 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!
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.
**Price increase due to the home’s expanded footprint—over 1,200 additional square feet!** **To be built! Welcome to this beautifully designed 3,540 sq. ft. home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The standard floor plan includes 4 bedrooms and 3.5 baths, with the option to expand to 5 bedrooms and 4.5 baths by adding a first-floor guest suite. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath and walk-in closet, complemented by a convenient second-floor laundry. Designed with future needs in mind, this home also offers the option of a residential elevator for effortless access across all levels. Enjoy broad water views and breathtaking sunrises over the Chester River. The covered porches and expansive windows create a seamless connection to the outdoors, enhancing the waterfront lifestyle of this sought-after community. Deep water boat slips are available for lease or purchase. The community amenities 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! Nestled in the sought-after Chester River Landing community, this home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.
Pricing reflects the property fully finished and professionally cleaned. This is a rare chance to own a completely restored Second Empire home on Chestertown Historic District’s most prominent corner. Water views are appreciated from two sides. Great balance of modern amenities and layout matched with historic design elements and style. The builders who took on this passion project are some of the most renowned in Kent County. 30-60 day estimated timeframe to complete upon contract acceptance. The detached garage is a huge plus with highly sought after off street parking.
Step into this nearly new, impeccably maintained two-bedroom townhouse located in the highly desirable Chester River Landing community. Recent upgrades make this home truly turn-key, perfect for those seeking comfort and style. Relax and entertain all summer long on the beautifully designed screened-in porch, ideal for enjoying warm evenings and gentle breezes. On the second floor, the spacious primary deck boasts expansive views of the Chestertown skyline and treats you to breathtaking summer sunsets—your personal oasis in this vibrant community. Just a short stroll away, you'll find the charm of Historic Downtown Chestertown and the scenic Wilmer Park, offering the perfect blend of convenience and lifestyle. Chester River Landing is a coveted water-access community offering a host of amenities, including an in-ground pool, two grilling and dining areas, and ample community space. Enjoy the large community dock with boat slips available for sale or lease—a dream for boating enthusiasts. Don't miss this opportunity to own a piece of Chester River Landing paradise!
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.
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.
Welcome to this beautiful 3-level Colonial in the sought-after Chester Harbor community on the Queen Anne’s County side! Nestled on a private lot, this home offers timeless charm, modern updates, and access to the water. Inside, you'll find three spacious bedrooms with newer carpeten upstairs with a full bathroom, while the main level features a large kitchen, dining room, and a cozy sitting area with a wood-burning fireplace. A second full bathroom on the main level adds convenience, and the home boasts gleaming hardwood floors and fresh paint throughout. The full basement provides ample storage or the potential for additional living space, and the 2-car garage offers plenty of room for vehicles and gear. Located in the water-oriented Chester Harbor community, this neighborhood surrounds the Chester River and offers fantastic amenities, including boat ramps for easy water access, a community pier for fishing and relaxation, and a park with picnic tables. Enjoy the peaceful setting while remaining just minutes from major routes, shopping, and dining. Don’t miss out on this incredible home—schedule your tour today!
Imagine waking up to gentle breezes and the promise of waterfront living. That's what awaits you in this brand-new home nestled within the peaceful Worton Creek community of Chesapeake Landing. Forget the cramped feeling of renting – here, you'll find space to breathe and room to grow. Picture yourself hosting friends and family in the bright, open living areas. The kitchen, with its crisp white cabinets and gleaming granite counters, is just waiting for you to create delicious memories. And with a main-level primary suite, complete with its own full bath, you'll have a true retreat at the end of each day. We know buying a home can feel overwhelming, especially if you're a first-time buyer. That's why we're thrilled to offer special financing programs that can make your dream of homeownership a reality. Imagine owning this brand-new home with zero down payment and closing cost assistance! It's truly an opportunity to build your future, not just pay someone else's mortgage. Think of the joy of exploring the waterfront, enjoying community events, and creating a life you love in Chesapeake Landing. This isn't just a house; it's a place where you can truly feel at home.
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!
Welcome to this charming 3-bedroom, 2-bath rancher offering comfortable one-level living in the desirable Chester Harbor community. Set on a spacious 0.76-acre lot on the Queen Anne’s side of the Chester River, this home is nestled in a water-oriented neighborhood—ideal for boating enthusiasts and nature lovers alike. Inside, you’ll find a generously sized primary bedroom featuring a private en-suite bath with a walk-in shower and an impressive walk-in closet complete with a cedar section for added warmth and storage. The kitchen and dining area showcase newer flooring installed just two years ago, creating a modern and inviting space for everyday meals and gatherings. Updated appliances add both style and functionality to the kitchen. Stay cozy and energy-efficient during cooler months with the wood stove, and enjoy comfortable summers with large window units that effectively cool the home. Outside, the fenced yard—installed just four years ago—offers a secure and spacious area perfect for children and pets to play and explore. A detached two-car garage provides ample storage for vehicles, tools, or all your boating and water toys. This inviting property combines comfort, convenience, and a sought-after waterfront lifestyle—an excellent opportunity to enjoy life near the Chester River.
Rare lake front property in Kent County! 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 bedroom in the walk out basement, there’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, kayaking 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. Welcome home!
Don’t let the outside fool you—this beautifully renovated 3-bedroom, 1.5-bathroom home offers three levels of living space, with over 2,200 sq. ft. above ground and an additional 550 sq. ft. below ground! Every inch of this home has been thoughtfully updated to blend modern comfort with timeless charm. Step inside to discover a stunning custom kitchen, a true chef’s dream featuring a gas stove, upgraded quartz countertops, solid wood cabinetry, and stylish open shelving—perfect for both cooking and entertaining. The spacious living areas boast brand-new LVP flooring, fresh finishes, and an inviting atmosphere throughout. Upstairs, the primary bedroom is a private retreat, complete with a mini-split AC/heat unit, a large dressing room, and a convenient half bath. Head downstairs to a versatile lower level, where an open-concept space offers endless possibilities—whether you need a media room, game area, crafting space, or home gym. The large laundry area and utility room provide added functionality. Step outside to your own backyard oasis, enclosed by a beautiful privacy fence. Enjoy the spacious patio, detached garage/barn, and storage shed—ideal for hobbies, storage, or workshop space. This home is completely move-in ready and packed with upgrades—all it needs is you! Don’t miss your chance to see this hidden gem—schedule your private showing today!
Completely remodeled, this three-bedroom waterfront home boasts a charming front porch and enormous back porch - your private space overlooking the river - along with an enclosed sunroom featuring gorgeous river views through walls of windows. Enjoy abundant outdoor areas and stunning water views from nearly every room. The dock features 3+ feel MLW, with slips available for purchase. This condominium embodies the ideal waterfront living experience. Located in the heart of historic Chestertown, this unique property includes off-street parking and provides the convenience of walking into town for dining and shopping. Situated on Maryland's scenic Eastern Shore, it's less than 85 miles from Washington D.C. and Philadelphia, making it a perfect meeting spot for those in the Mid-Atlantic region.
A Rare Opportunity in the Heart of Historic Chestertown Discover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage. Brimming with character and potential, the property currently features a townhouse on one side and two apartments on the other, offering a flexible layout ideal for renovation, income generation, or a creative reimagining. Whether you're envisioning a stately single-family residence, a dynamic live/work space, or a thoughtfully restored multi-unit investment, the possibilities are as expansive as the lot itself. That said, this is not a turnkey property. Significant settling has occurred over the years, and a substantial renovation will be required to bring it back to life. Offered strictly as-is, this is a true fixer-upper for the visionary buyer ready to take on a transformative project. Situated within both the Arts & Entertainment District and Enterprise Zone, this location supports both residential and business uses—making it an ideal candidate for those looking to merge lifestyle, business, and history. Bring your vision, creativity, and tools—and seize the chance to breathe new life into a piece of Chestertown’s storied past. Opportunities like this don’t come along often. Schedule your showing today and imagine the future you can build here. **See updated zoning info from the town in documents
A stately 1800’s waterfront Victorian home, rich in history enters a new chapter in life with 6 condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. This unit offers a 2 Bed 1 bath has a brand new kitchen, with island and upgraded bathroom along with up and down river views. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own ground level storage. Deeded slips are also available for purchase, with boat lifts! This is a unique setting offering waterfront living in downtown historic Chestertown and includes off street parking. Walk to downtown restaurants and shops. Beautiful southeast views of the Chester River with spectacular sunrises and plenty of year-round sunshine. Take in the all of the nearly year-round waterfront activities from your own back yard, including Chestertown Tea Party, 4th of July fireworks and Sultana down rigging weekend. Located on Maryland’s scenic eastern shore less than 85 miles from Washington DC to the south or Philadelphia to the north, this home is the perfect meeting spot for those living in the Mid-Atlantic region.
Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away.
Chestertown is located in Maryland. Chestertown, Maryland has a population of 5,557. Chestertown is less family-centric than the surrounding county with 10.61% of the households containing married families with children. The county average for households married with children is 15.86%.
The median household income in Chestertown, Maryland is $44,665. The median household income for the surrounding county is $64,451 compared to the national median of $69,021. The median age of people living in Chestertown is 39.1 years.
The average high temperature in July is 87 degrees, with an average low temperature in January of 25.4 degrees. The average rainfall is approximately 45.1 inches per year, with 13.9 inches of snow per year.
