90 properties for sale in Lees Corner, Chestertown town District 4 Chestertown Kent County Maryland

Welcome to 11029 Brindley Drive that is move-in ready with new flooring, heat/air and has been freshly painted. The open floor plan offers great family time and the back yard backs to trees which now offers privacy and shade for picnics and play. Convenient to Parks and Recreation with a public beach only minutes away

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

Fully renovated from top to bottom, this charming 3-bedroom, 1.5-bath townhome in the heart of downtown Chestertown offers the perfect blend of modern updates and convenience. Step inside to find new flooring, new carpet, fresh paint throughout, updated molding, and a beautifully renovated kitchen featuring white cabinetry, new countertops, and new appliances. Both bathrooms have been completely updated with all new fixtures and finishes. The main level offers ample living space, dinging room and new kitchen and laundry. Upstairs you will find three bedrooms and a full bathroom, with access from the primary bedroom as well. Outside, enjoy a newly fenced backyard, updated shed, and an extra-deep lot offering the potential for additional rear parking. A new roof installed in 2024 adds even more value and peace of mind. Boasting generous space and extensive upgrades throughout, this home presents an exceptional opportunity for a primary residence, weekend getaway, or investment property.

Gorgeous house on River Rd in the Queen Anne's County side of Chestertown. 3 total bedrooms and 2.5 baths. The main bedroom is on the first floor. Stunning sun room, patio and pool. 2 car garage. Living room and den

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 home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Looking for peaceful country living? The search is over! Nestled on 1.66 acres, this beautifully renovated 3-bedroom, 1.5-bath home offers the perfect blend of comfort, functionality, and privacy with NO HOA! In addition, there's a versatile bonus/flex room that is ideal for a home office, hobby area, or even a potential 4th bedroom to suit your needs. All on the convenience of one-level living. Step inside to discover a bright, inviting interior featuring brand-new luxury vinyl plank flooring and carpet, fresh paint throughout, and a thoughtfully updated kitchen complete with new butcher block countertops, brand-new stainless-steel appliances, and ample cabinet space. A new HVAC system, brand-new roof, and a ONE-YEAR HOME WARRANTY provide peace of mind, allowing you to move in and enjoy your new home from day one. Outside, the expansive 1.66-acre lot offers endless opportunities for gardening, entertaining, recreation, or simply enjoying the tranquility of nature. A storage shed provi

Welcome to 25003 Heather Ln! This well maintained 3 bedroom, 2 full bath home offers the ease of first floor living in a quiet neighborhood. Inside, you'll find an open concept layout with high ceilings that create a bright, spacious feel, along with modern finishes throughout. Outside, the huge yard provides plenty of room for entertaining, gardening, pets, or simply enjoying the outdoors. Move in ready and conveniently located, this home is one you won't want to miss. Schedule your showing today!

This cute as a button downtown stunner is recently updated and ready for the next owner to fall in love with the lifestyle that comes with living in the Historic District. Located on a quiet side street just a block from Chestertown's dining, shopping, and galleries, this is the perfect blend of social and tranquil. This means that walking down to Evergrain or Modern Stone Age Kitchen for a croissant and cappuccino before a morning stroll along the waterfront promenade could become part of your morning routine. The thoughtful updates over the years have opened the floor plan and allowed for a modern layout. Many serious upgrades have occurred in the past year including the kitchen and electrical service. The wood burning stove, basement for storage, and garden building are amazing benefits. Invest wisely in an amazing home while improving your quality of life in this incredible community on the water less than 2 hours from Washington DC, Philadelphia, and Baltimore

Charming Brick Rancher Near the Chester River This custom-built brick rancher sits in a nice Chestertown neighborhood with excellent curb appeal, a classic hipped roof, and a convenient circular driveway. The drive runs under a gable-roofed breezeway that connects to an oversized 26x40 two-car garage, which will soon have brand-new garage doors. Coming into the Home. Living Room: Walk along the cobblestone slate path and pass through the new, classic front door into a spacious living room featuring hardwood floors that run throughout the entire house. Dining & Kitchen: A curved archway leads from the living room directly into the dining room. The dining room has an entryway to the kitchen, which could easily be opened up for an even more open feel. Porch: The dining room leads right out to a comfortable porchthe perfect spot to relax and enjoy this nice, quiet neighborhood. Mudroom & Back Entry: An oversized back entry from the breezeway leads into a large mudroom and utility space. Fe

Prime location in Downtown Chestertowns Historic District offering approximately 1,785 square feet of practical living space on three levels with 4 off-street parking spaces. The RB zoning also provides flexibility for live/work arrangements, and the property has rare building expansion potential to accommodate family and/or business growth

Nestled in the desirable Crestview neighborhood, this beautifully maintained rancher built by respected local builder KRM Construction offers the perfect blend of quality craftsmanship, comfort, and modern convenience. Built in 2017, this 3 bedroom, 2 bathroom home features an inviting open layout with luxury plank hardwood flooring throughout the main living areas, granite countertops, abundant cabinet storage, and a cozy propane fireplace. The spacious primary suite includes a large walk-in closet and a luxurious en-suite bath complete with a soaking tub and separate shower. Enjoy relaxing mornings on the screened porch or unwind evenings around the fire pit on the paver patio just off the living room. Additional highlights include a 2-car attached garage, sprinkler system, hot water on demand, new propane furnace installed in 2026, and new dryer in 2025. Conveniently located close to all of Chestertown amenities, with a voluntary HOA of just $100/year. Showings begin 5/22 this is on

Welcome to the epitome of Eastern Shore waterfront luxury, offered for the first time in almost 60 years. This stunning 11-acre estate offers an unparalleled lifestyle, featuring 560 feet of prime water frontage on the Chester River and a private 140-foot dock with 7 feet of mean low water, perfect for all your adventures. The heart of this property is the beautifully renovated 3-bedroom, 2 full bath, 2 half bath main home, meticulously remodeled in 2018 with the highest quality materials and fixtures. The residence boasts sweeping water views from nearly every room, allowing you to enjoy picturesque sunrises Chester River. As you enter, you are greeted by a grand living room featuring a striking five-foot fireplace set within a soaring vaulted ceiling, creating a warm and inviting atmosphere. Expansive windows frame the breathtaking views and fill the space with natural light, enhancing the open-concept design that is perfect for both relaxing and entertaining. The gourmet kitchen is

Move-in ready and priced to sell, this 3-bedroom, 2.5-bath end-unit townhouse offers the perfect blend of value, comfort, and natural light. Tucked alongside community open space, this home lives larger than expected with added privacy and bright, airy interiors. Inside, youll find upgraded flooring and modern lighting throughout, creating a clean, updated feel from the moment you walk in. Two designated parking spaces included. As an added bonus, most furnishings convey, making this an easy, turnkey option for buyers looking to settle in quickly. Opportunities like this dont come along oftenespecially at this price point!

Searching for a home with peaceful country views and a beautifully designed interior? This meticulously maintained property offers the perfect blend of modern style, comfort and functionality. Inside, youll find cathedral ceilings with a beautiful wood accent beam, gorgeous LVP flooring throughout and a light, airy feel created by the neutral color palette and crisp white trim. The open floorplan is ideal for both everyday living and entertaining, centered around a stunning kitchen featuring custom tile backsplash, black farmhouse accents, matching stainless steel appliances, gas range, recessed lighting and a large center island with pendant lighting above. The spacious primary suite includes a walk in closet and private bath complete with dual vanity, standing shower and linen closet. Outside, the fully fenced backyard overlooks wide open farmland views and includes a charming shed with covered front porch, creating the perfect place to sit back, relax and enjoy peaceful surroundings

To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to the private balcony. Two additional bedrooms share a full bathroom. The upstairs is complemented by a convenient second-floor laundry. Catch a glimpse of the Chester River from the front porch or upper covered balcony, the perfect place to enjoy morning coffee or evening cocktails. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, ca

Newly constructed three-bedroom townhome with fantastic water views from the living level and bedrooms! Spacious open living space featuring a gourmet kitchen; 5-burner induction range, ample cabinet space, and a large island for entertaining. The home is filled with natural light and boasts multiple balconies and a front porch for relaxing. You'll love the warm hardwood floors throughout the home. On the second level you'll find two bedrooms and two bathrooms. The third bedroom encompasses the entire third floor and has a great view of the Chester River. You'll enjoy the large back balcony with views of historic Chestertown. The third level could be used as the primary bedroom; there is a large full bathroom and closet. The townhomes have a private driveway, so you'll never worry about finding a parking space. Take advantage of the easy access to Wilmer Park and Chestertown Marina, located just across the street. This townhouse is located in the heart of all Chestertown has to offer!

This charming 1916 home in Chestertown's historic district is in a quiet neighborhood next to Washington College, just a short walk from downtown and the waterfront. Three finished levels and high ceilings plus bright, natural light make the home feel airy and spacious. Historic features include original heart-pine hardwood floors and beautiful molding throughout. The first floor includes an adorable kitchen with butcher block countertops, as well as a living room, dining room, and 3/4 bathroom. Upstairs, youll find three bedrooms, a full bath, and a walk-in closet. The third floor offers a lofted bedroom and bonus room. Perfect for a playroom, office, or workout room. The mahogany-floored porch has interchangeable screens and windows, converting easily from a screen porch into a sunroom. Outside, a new six-foot pressure-treated pine fence provides privacy for the backyard, with an extra fenced garden area. The driveway has off-street parking for two vehicles. Additional home updates i

Welcome to this sweet ranch-style home in Worton, Maryland, tucked into a quiet little neighborhood of Knight’s Landing surrounded by beautiful farmland. It’s the perfect spot if you’re looking for peaceful living without feeling far from everything—just under five minutes to the local high school, community center, and park. Cozy, convenient, and easy on the budget, this home offers small-town vibes with everyday essentials close by. Seller is offering a $5,000 credit to the buyer! Property sold AS.is seller will make no repairs

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 2B. Listed for $350,000: a one bedroom, one bath w

Coventry FarmsReduced to Sell, Offers Encouraged Located in the highly desirable Coventry Farms community, this home presents a wonderful opportunity for its next owner to bring fresh vision and personal touches. With the seller preparing for a move out of the area, the property has been reduced to reflect its current condition and to encourage a timely sale. Inside, youll find generous living space and a functional layout ready to be reimagined. Updates such as new flooring, fresh paint, and cosmetic improvements will make an immediate impact and allow you to truly make this home your own. Whether youre looking to settle into a sought-after neighborhood or invest in long-term value, the potential here is undeniable. Coventry Farms is known for its appeal, convenience, and strong sense of communitymaking opportunities like this especially rare. Seller is ready to consider strong offers. Bring your ideas, add your style, and take advantage of this chance to create something special in a

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 2B. Listed for $350,000: a one bedroom, one bath w

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 1B – Listed $200,000: the most cozy setting! One b

103 Sutton is perfectly situated just a stone’s throw from the vibrant heart of Downtown Chestertown. This exquisite 4+ bedroom residence is designed to cater to the diverse needs of today’s Buyers, offering a harmonious blend of comfort, style, and functionality. This home is ideal for those upsizing or seeking multi-generational living. Originally built as the community model home – and meticulously maintained since – it has ALL the extras: generous breakfast nook bump out, gas fireplace, gleaming hardwood floors, upgraded carpet, oversized windows, granite countertops, stainless appliances, dedicated home office, and a finished basement with a full bath and expansive wet bar. As you step inside, you’ll be greeted by a two-story foyer flooded with light, dining room and den or family room. The gourmet kitchen that is a chef’s paradise, featuring high-end appliances, custom hardwood cabinetry, and a small island for an ideal triangle of space for meal prep. The open concept layout flo

Listing price is for ALL FOUR available units for sale as an investment package! Pricing for each unit and their details are below. 117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all