73 properties for sale in Chesapeake Landing, District 3 Worton

Brand new construction in Chesapeake Landing, and the primary suite is on the main level full bath, walk-in closet, no stairs at the end of the day. That one detail is what most buyers spend months searching for and rarely find at this price. Roughly 1,600 square feet, laid out so the main floor handles everything: an open living room, a kitchen with shaker cabinets, granite counters and stainless steel appliances, plus laundry and a half bath. Luxury vinyl plank runs throughout the kind of floor that still looks right after wet boat shoes and muddy paws. Upstairs, two additional bedrooms share a full bath. Guests, an office, a hobby room tucked away from the main living space so the first floor stays yours. The lot is a third of an acre with a private driveway, giving you real yard on all sides rather than a strip of grass between neighbors. Chesapeake Landing is a waterfront community with a clubhouse, walking trails and community water access. Membership in the community association

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

Welcome to a breathtaking country estate where modern elegance, architectural grandeur, and total sanctuary converge across 2.23 serene acres. Spanning over 4,000 square feet of meticulously refined living space, this extraordinary five-bedroom residence has been thoughtfully crafted to offer both lavish entertaining possibilities and effortless multi-generational comfort. Upon arrival, the welcoming foyer makes a memorable first impression, framed by detailed custom millwork and flanked by a private executive office and a sophisticated study or formal dining space. Moving inward, the magnificent two-story great room commands attention with its soaring ceilings and a cozy gas fireplace crowned by a classic raised brick hearth. At the heart of the main level lies a gourmet kitchen designed for grand gatherings, showcasing fresh luxury vinyl flooring, select new appliances, and a stunning quartz-topped center island with a prep sink that easily reconfigures for multi-purpose hosting. Sun

Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs youll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertowns most historic locations

A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial. Full finished basement. More details and pictures coming soon!

Embrace Eastern Shore living in this beautifully designed Oak Hollow townhome. Offering 1,900 square feet of spacious, three-level living, this property is perfectly positioned just minutes from historic downtown Chestertown, local schools, and the YMCAblending everyday convenience with a welcoming community atmosphere. Enter through the ground floor, where a flexible bonus room and one-car garage offer endless possibilities for a home office, gym, or recreation space. The heart of the home sits on the main level, featuring a generous living room and an eat-in kitchen that opens to a private rear deckthe perfect spot to unwind and look out at the wooded backdrop. Upstairs, you will find three comfortable bedrooms, including a primary suite with a private bath, alongside a dedicated laundry area. Turn-key and low-maintenance, this property is a fantastic opportunity for first-time buyers, downsizers, and investors alike

Price Reduction! VERY motivated selleropen to all reasonable offers. Welcome to this beautifully maintained 4-bedroom, 2.5-bath home built in 2022, offering the perfect blend of modern comfort and peace of mind. Freshly painted with brand new carpet, this home features a bright, open floor plan ideal for both everyday living and entertaining. Enjoy the benefits of newer constructionmajor systems like the roof, HVAC, and water heater are all just a few years old, giving you confidence and low maintenance for years to come. Located in a desirable community with an affordable HOA that includes lawn mowing, youll appreciate easy, low-maintenance living. Conveniently situated just minutes from shopping centers, restaurants, and everyday amenities. This move-in ready home is truly a must-see!

Light-filled home with glowing wood floors, exposed beams, skylights, and open living space. This one-level home is nestled on just under two acres! The expansive yard offers room for many activities and provides scenic views from the home. Inside, the open living space is bright and airy, with skylights, bay windows, and vaulted ceilings with exposed beams. The large kitchen has beautiful updated granite countertops, a large pantry, kitchen island with seating, and ample cabinet space. From the dining room you can explore the raised deck with a hot tub! Or enjoy meals on the screened porch, finished with water and electricity. This one-level home boasts 3 spacious bedrooms and 2.5 bathrooms. The primary bedroom has a walk-in closet and opens to a sun-filled studio or office space, which has access to the raised deck. There is an attached two-car garage with ample storage space, which could also make a great workshop. Under 15 minutes to downtown Chestertown and less than an hour to Mi

Situated on. 97 acres in Worton, this versatile property offers plenty of space and possibilities with two utility buildings, public water, and public sewer. The main home features an open floor plan highlighted by a custom wooden kitchen bar that provides generous counter space and creates a natural gathering spot for entertaining. A separate shop building adds even more functionality and is equipped with an oil furnace and air conditioning, making it comfortable for year-round use. Whether youre looking for workshop space, storage, a hobby area, or room for your next project, this property offers flexibility that's hard to find. Conveniently located in Worton with nearly an acre of land, public utilities, and multiple buildings, this property is ready for its next owner to make it their own

A rare opportunity to own a classic two-story split-level home in Chestertown set on a large, shaded corner lot just a few miles to Downtown Chestertown, Washington College, the weekly farmers market, the town's annual festivals, and only steps to locally loved restaurants and everyday conveniences. This is the kind of home that simply isn't built anymore: classic lines, original details, and the quiet character that comes from decades of careful ownership. Step inside and the home tells its story with original trim, classic proportions and timeless architectural touches. The two-story split-level floor plan offers a thoughtful separation of living and sleeping spaces, with a sun-filled sunroom that works beautifully as a screened porch when the doors are all open or as extra living space during the shoulder seasons. Two of the bedrooms sit on the upper level, while two large bedrooms flow comfortably below. Out back, the large, gently sloped corner lot offers privacy, mature trees, an

Move-in ready and packed with updates, this 3-bedroom, 1-bath home offers an affordable opportunity to enjoy Eastern Shore living without a long list of projects waiting for you. Major improvements include a newer roof, HVAC system, water heater, stainless steel appliances, luxury vinyl plank flooring, carpet, fresh paint, recessed lighting, plus a vapor barrier and insulation in the crawlspace. Inside, the home feels bright, clean, and refreshed, making it an easy choice for buyers looking for comfort, convenience, and low-maintenance living. The location makes it even better. In approximately 12 minutes, you can be exploring historic Chestertown, spending the day at Betterton Beach, or enjoying waterfront dining, boating, and sunsets at Great Oak Landing. With its extensive updates, convenient location, and newly improved price, this home offers a lot of value for buyers

Professional Pictures Coming Soon! Fantastic opportunity to own a beautifully maintained 3-bedroom, 2.5-bath townhome in The Village of Chestertown, offered at a price that is. Below market value! Only 3 years young and in excellent condition, this home offers the benefits of newer construction. Conveniently located with an easy commute to Route 301 and just around the corner from the newer YMCA. Enjoy all that Chestertown has to offer, from its charming small-town atmosphere and wonderful restaurants to artistic venues, community events, and Washington College. A must-see for buyers looking for a newer home, excellent condition, and exceptional value in a great location!

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 9/15/2026, 10:00 AM. Bidding ends 9/17/2026, 12:40 PM. The list price is the suggested opening bid. Deposit: $15,000. This auction takes place on the Ashland Auction Group Website Bidding Platform. Pre-auction offers may be accepted. Located along Marylands Eastern Shore in Kent County, this single-family home offers approximately 1,896 square feet of living area on a 0.51 acre lot. The home is situated along Worton Road, approximately five miles north of historic Chestertown. The location provides convenient access to shopping, dining, employment centers, recreational amenities, and the surrounding waterfront communities of Kent County. Maryland Route 297 provides connectivity throughout the Worton and Chestertown areas, while nearby routes offer access toward Rock Hall, Betterton, Cecil County, and Delaware. Each person entering the property is required to complete a right o

Welcome to this beautifully crafted home in the water-oriented community of Great Oak Estates, just outside of Chestertown on Marylands Eastern Shore. Nestled in a peaceful setting that backs to woods alive with songbirds and butterflies, this high-quality residence offers an easy-flow floor plan designed for both lively gatherings and quiet private moments. A soaring two-story foyer greets guests and opens to the living room and family room, the latter featuring built-in cherry cabinets and a cozy propane fireplace. The formal dining room connects seamlessly to the kitchen and an additional casual dining space, making entertaining effortless. The kitchen showcases handmade cherry cabinetry and a brand-new refrigerator. Hardwood floors run throughout the main living areas, while brand-new carpeting softens every bedroom. On the main level, the primary suite includes its own bathroom, a walk-in closet, and plantation shutters. A second main-floor bedroom (ideal as a guest room or home o

Price Improvement! Now offered at $239,900 Welcome to 104 Conley Drive in the heart of Chestertown! This move-in ready 3-bedroom, 1.5-bath townhome offers comfortable, low-maintenance living with a spacious layout and fenced rear yard. The main level features a bright living room, an eat-in kitchen with ample dining space, and a convenient half bath. Upstairs, youll find three bedrooms and a full bath. Notable updates include a new HVAC system installed in 2020 and a sewer line replacement completed approximately four years ago, providing added peace of mind for the next owner. Enjoy outdoor entertaining, gardening, or relaxing in the private fenced backyard. Conveniently located near shopping, dining, schools, parks, the YMCA, and historic downtown Chestertown, this home is an excellent opportunity for first-time buyers, downsizers, or investors alike. Schedule your showing today!

Welcome to 25133 Smithville Rd. This spacious 4-bedroom, 3-bath traditional Colonial offers comfortable living with plenty of room to spread out. The main level features a desirable primary suite with a private full bath, along with an inviting eat-in kitchen and formal dining room perfect for everyday living and entertaining. Step outside to enjoy the spacious, level backyard with fencing for added privacy. There is plenty of room for entertaining, family gatherings, kids, pets, outdoor activities, and moreall while enjoying your own private outdoor space. With its spacious layout, convenient main-level primary suite, and private backyard, this home offers a wonderful opportunity to make it your own. Come see all that 25133 Smithville Rd. Has to offer and make this home yours!

Built in 1780/1-, Highcroft' is in the heart of the Historic District near the Chester River. A rare in-town property that offers a 2-car garage with a second floor and a long driveway for tons of off-street parking. 3 bedrooms, 4 full baths and 1 half bath. Primary bedroom has his and hers private baths. 8.2 kw solar array on the garage. EV level 2 charger. Easy room flow from front to back for entertaining. Just steps to restaurants, bars, and shops. This is an ultra efficient'green' house

Investor Special Charming Colonial in Prime Chestertown Location! Welcome to 234 N College Ave, an adorable colonial full of character and potential, nestled in the heart of historic Chestertown. This short sale opportunity is a rare find for savvy investors or buyers ready to bring their vision to life. With classic colonial charm, this property offers the perfect canvas for renovation or restoration. Located near downtown Chestertowns shops, restaurants, and waterfront, the location cant be beat. Original architectural details, a cozy layout, and timeless curb appeal make this home a standout gem waiting to be polished. Don't miss your chance to invest in one of Marylands most beloved small towns. Sold as-is. Cash or renovation loans preferred

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 9/15/2026, 10:00 AM. Bidding ends 9/17/2026, 12:45 PM. The list price is the suggested opening bid. Deposit: $15,000. This auction takes place on the Ashland Auction Group Website Bidding Platform. Pre-auction offers may be accepted. Located along Marylands Eastern Shore in Kent County, this single-family home offers approximately 1,056 square feet of living area on a 0.46 acre lot. The home is situated along Worton Road, approximately five miles north of historic Chestertown. The location provides convenient access to shopping, dining, employment centers, recreational amenities, and the surrounding waterfront communities of Kent County. Maryland Route 297 provides connectivity throughout the Worton and Chestertown areas, while nearby routes offer access toward Rock Hall, Betterton, Cecil County, and Delaware. Each person entering the property is required to complete a right o

Historic Charm in the Heart of Downtown Chestertown Step back in time and discover the character, craftsmanship, and endless potential of this circa-1820 historic home. Nestled in the heart of downtown Chestertown, this property is filled with the original architectural details and timeless charm that historic home lovers dream about. Featuring 2 spacious bedrooms with the potential for a 3rd, 3 full bathrooms, a welcoming kitchen with an eat-in area, and a generously sized dining room, this home offers a solid foundation for restoration and reimagining. While the property is in need of some repairs and renovation, it presents an incredible opportunity for the buyer who has always dreamed of owning a piece of history; or the savvy investor looking for their next restoration project. Outside, escape to your own private backyard sanctuary complete with a brick patio, fountain, and peaceful garden setting, an unexpected retreat right in town. Please note that the home is currently furnish

Welcome to this beautifully renovated 2-bedroom, 1-bath townhome offering the perfect blend of comfort, style, and convenience. Completely updated from top to bottom, this move-in-ready home features brand-new luxury vinyl plank flooring, fresh paint throughout, quartz countertops, an updated bathroom, and several new appliances. The fully equipped kitchen opens to a comfortable living and dining area, where a sliding glass door leads to your own private concrete patio; perfect for enjoying your morning coffee or relaxing outdoors. Upstairs, you'll find two generously sized bedrooms, a full bathroom, and additional storage space. All appliances convey, making this home truly turnkey. Nestled in a peaceful, wooded setting between Rock Hall and Chestertown, you'll enjoy a serene atmosphere while being just minutes from schools, shopping, beaches, marinas, and local dining. Whether you're a first-time homebuyer, looking to downsize, or searching for your next investment property, this bea

Seller is offering a 1 year home warranty with acceptable offer. Welcome to Tolchester Estates, a charming community near the Chesapeake Bay. This 3-bedroom, 2-bath rancher features updated HVAC, gas cooking, an upgraded propane hot water heater, and a recently replaced roof system in March 2026. The property is served by public sewer for added ease and reliability. Step outside to a large rear deck, perfect for entertaining or relaxing while enjoying the peaceful surroundings. The home also offers plenty of storage space in the attic, providing added convenience and functionality. Residents enjoy access to a private community beach and boat ramp. Also conveniently located within walking distance to Tolchester Marina and Shanty Beach Bar, offering outdoor entertainment throughout the summer months. Approximately 10 minutes to Rock Hall and 20 minutes to Chestertown, this home offers the perfect blend of comfort and rural living. Enjoy all that Tolchester has to offer at 8706 Elm

Welcome home to relaxed Eastern Shore living in the waterfront community of Chesapeake Landing. This beautifully updated 2,140 sq ft Cape Cod offers the perfect blend of charm and modern comfort with 3 bedrooms, 2.5 baths, and a welcoming floor plan designed for everyday life. The main level features new flooring throughout, a spacious living area, formal dining room, and a renovated country kitchen with new appliances, new counters, and plenty of space for gathering. A main-level bedroom adds flexibility for guests or one-level living. Enjoy morning coffee or evening sunsets on the back deck overlooking the open, cleared 0.39-acre lotperfect for gardening or outdoor fun. Additional highlights include a 2-car garage and access to community amenities with a beach, fishing pier, and pavilion. Just minutes from historic downtown Chestertown, youll love being close to local shops, dining, marinas, and all the charm of Eastern Shore living

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted