229 houses for sale in Kennedyville, District 2 Kennedyville Kent County Maryland

Vintage home with lots of original details retained. 3 Staircases, 3 original fireplaces and a very grand front foyer and staircase give this home so much character! Current owners have updated it lovingly throughout. Enter through the spacious back yard, into a welcoming mudroom with a full bath on the main floor to your left and then into the updated and cozy kitchen with new dishwasher, LVP flooring, complete with the cutest back stair case! The staircase leads up to a separate home office, craft room, den, or 4th bedroom. Also downstairs is a main floor bedroom, a nice size dining room with decorative fireplace and parquet flooring, and a Living room with new carpet, and a new pellet stove to keep you warm on those chilly nights. On the 2nd level are 2 bedrooms plus the office, and a full bathroom. Full stairs to the 3rd floor leads to 2 additional rooms that could easily be finished into more living space. Since 2018 the current owners have updated the home to include: New Roof on

Price improvement: Colonial in Kennedyville overlooking the pond. Situated on a corner lot with a private driveway behind the house. 2 car attached garage, 4 bedrooms and 2.5 baths. Gas fireplace. Large mudroom with laundry. Partially finished basement with new carpeting. Lovely front porch for relaxing and enjoying the view

Buyer's remorse means this house is again available at an amazing price! Spacious home in Kenndyville with lots of amenities. Featuring 4 bedrooms and 2.5 baths with a large kitchen with granite countertops, living room with gas fireplace, 2-car detached garage, and a huge unfinished basement. Plenty of storage. Deck off the living room leads to a partially fenced back yard. Just a short drive to downtown Chestertown

Charming home nestled on a spacious lot in the Rock Hall area. This property offers comfortable single-level living with a functional layout, generous outdoor space, and plenty of room to enjoy the peaceful surroundings. Conveniently located near local amenities, marinas, and the Chesapeake Bay, this home presents an excellent opportunity for year-round living, a weekend retreat, or investment potential. Don't miss the chance to make this Eastern Shore property your own! Sold as is

Reice reduced! Completely renovated from the studs up, this beautifully updated 3-story home offers 2,200 square feet of thoughtfully designed living space just outside of Rock Hall. Featuring 3 spacious bedrooms and 3 full bathrooms — one on each level — this home provides flexibility and comfort for everyday living or guests. The open-concept main floor showcases luxury flooring, brand-new stainless steel appliances, and abundant natural light throughout. A convenient rear mudroom leads to a covered porch. Upstairs, you’ll find generously sized bedrooms with large windows, while the third floor offers an additional expansive sitting area — perfect for a home office, media room, or bonus living space. Brand-new carpeting adds warmth and comfort to the upper levels. The current owners have incorporated thoughtful upgrades and modern features throughout, making this home truly move-in ready. Enjoy the charm of Rock Hall living with the benefit of a fully updated home just minutes from t

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

Tucked away just south of the scenic Chester River and moments from the timeless charm of Chestertown, this inviting home offers a warm and welcoming retreat in the heart of Queen Anne’s County. Surrounded by the natural beauty of Maryland’s Eastern Shore, the setting feels peaceful and relaxed—where quiet mornings and golden sunsets become part of everyday life. Inside, the home is designed for comfort and easy living, featuring a desirable first-floor primary suite that provides both privacy and convenience. The spacious family room, anchored by a cozy gas fireplace, creates the perfect gathering space, while the rear screened-in porch invites you to unwind and enjoy the tranquil surroundings. Upstairs, you’ll find two additional bedrooms along with a versatile bonus room—ideal as a home office, playroom, or craft space—plus walk-in attic storage for added functionality. Outdoor living shines with a brand new deck complete with a hot tub, perfect for relaxing or entertaining under th

Multiple offers received-deadline is 3/24 at 11am*. Welcome to this beautifully updated historic gem in the heart of Sudlersville! Offering 3 bedrooms and 2 bathrooms, this home perfectly blends timeless character with modern upgrades. The majority of the home has been thoughtfully renovated including the entire main level with a renovated full bath, new drywall, plumbing, electrical, and windows. Comfort is key with efficient mini-splits providing heating and cooling throughout, plus the added charm of cozy oil heat & an inviting pellet stove. The stunning, fully renovated gourmet kitchen is truly a showstopper & the heart of the homegorgeous, functional, gas cooking, stainless steel appliances, and ready to impress anyone who loves to cook or entertain. A brand-new roof was installed in the winter of 2025 for added peace of mind. This home was not a flip & the owners made renovations with intention & care for design and livability. Upstairs, renovations are only partially complete, o

Reice reduced! Completely renovated from the studs up, this beautifully updated 3-story home offers 2,200 square feet of thoughtfully designed living space just outside of Rock Hall. Featuring 3 spacious bedrooms and 3 full bathrooms one on each level this home provides flexibility and comfort for everyday living or guests. The open-concept main floor showcases luxury flooring, brand-new stainless steel appliances, and abundant natural light throughout. A convenient rear mudroom leads to a covered porch. Upstairs, youll find generously sized bedrooms with large windows, while the third floor offers an additional expansive sitting area perfect for a home office, media room, or bonus living space. Brand-new carpeting adds warmth and comfort to the upper levels. The current owners have incorporated thoughtful upgrades and modern features throughout, making this home truly move-in ready. Enjoy the charm of Rock Hall living with the benefit of a fully updated home just minutes from town, ma

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!

Lovely 4 Bedroom home with 1 and 1/2 baths located just outside of town. This home has 2 separate entrances at the front of the house. One can be entered and separated from the whole house living space. Great for an office with 1/2 bath or used as another bedroom if you need 4. Kitchen leads to separate laundry and mud room and exits to the back yard with a view of acres of open space fields

Move in ready! Adorable, Affordable, move in ready & two blocks from the Chesapeake Bay! Appliances, roof, waterproof vinyl plank flooring, stove, dishwasher recently upgraded, beautifully tiled bathroom flooring. Freshly painted, Bright and inviting updated kitchen, Spacious Diningu002Ffamily rm with vaulted ceilings, ceiling fan. Enjoy fishing or relaxing at the private community beach or head over to Tolchester Marina & The Shanty Beach Bar, dining & shopping. Just a very quick trip to entertainment, or boating. Great location, private lot 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 sweet ranch-style home in Worton, Maryland, tucked into a quiet little neighborhood of Knights Landing surrounded by beautiful farmland. Its the perfect spot if youre looking for peaceful living without feeling far from everythingjust 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

Absolutely Stunning Custom-Built Home! A Rare Opportunity You Won't Want to Miss! Welcome to this exceptional home offering nearly 3,000 square feet of beautifully designed living space, where luxury, comfort, and style come together effortlessly. Showcasing outstanding craftsmanship, thoughtful design, and high-end finishes throughout, every detail has been carefully curated to create a home that is both elegant and inviting. Featuring 4 bedrooms and 2.5 baths, this home is perfectly situated on a level 1 acre lot directly across from the scenic Chester River. From the moment you step inside, you’ll love the expansive open-concept layout, soaring ceilings, and upscale finishes throughout. The gourmet kitchen is a true showstopper, complete with a large island, sleek quartz countertops, and a hidden pantryu002Fworkstation designed for both beauty and function. The inviting stone fireplace creates the perfect focal point for gathering and entertaining. Additional highlights include spac

Introducing 106 Charles St in Sudlersville, MD a fully renovated, turn-key property offering a rare opportunity for Assisted Living, Transitional Housing, or Specialty Care operations. Formerly licensed and now newly approved by the Town of Sudlersville for a 16-bed Assisted Living Facility, this building is ready for launch by a first-time operator, an expanding provider, or a real estate investor seeking strong cash flow. This expansive facility includes 12 bedrooms, 3 full baths, 2 half baths, and is fully equipped with fire suppression (sprinkler) and fire alarm systems for safety and compliance. A commercial kitchen, large recreation/activity room, and multiple communal spaces create an ideal resident experience. A key highlight is the separate 2-bedroom apartment with its own kitchen and bathroomperfect for an on-site caregiver, staff suite, or premium private living area. Additional features include, Large rear deck for outdoor enjoyment, Full basement for storage, Parking for 8

Move in ready! Adorable, Affordable, move in ready & two blocks from the Chesapeake Bay! Appliances, roof, waterproof vinyl plank flooring, stove, dishwasher recently upgraded, beautifully tiled bathroom flooring. Freshly painted, Bright and inviting updated kitchen, Spacious Dining/family rm with vaulted ceilings, ceiling fan. Enjoy fishing or relaxing at the private community beach or head over to Tolchester Marina & The Shanty Beach Bar, dining & shopping. Just a very quick trip to entertainment, or boating. Great location, private lot 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 one of Sudlersville's most extraordinary heritage homes, a magnificent Queen Anne Victorian that beautifully honors its historic character while embracing the comforts of modern living. Following an extensive 2019 renovation that left virtually no system untouched, this remarkable residence has been thoughtfully reimagined for today's lifestyle while preserving the timeless architectural details that make it truly one of a kind. Set on more than an acre beneath majestic centuries-old shade trees, this magical family estate commands attention with its soaring turret, five striking bay windows, and deep, sweeping wraparound porch that invites you to slow down and savor every season. Overlooking the neighborhood park, the setting is as enchanting as the home itself, nestled within the quintessential Hallmark town of Sudlersville, where the historic train station now serves as a museum and the soft rumble of the grain train passing through town a few times each week provides a n

Discover this beautiful 3-bedroom Cape Cod home in the heart of Worton, Maryland, conveniently located near local amenities and scenic Eastern Shore attractions. Thoughtfully updated with over $20,000 in upgrades, this residence effortlessly blends classic charm with modern comfort. The inviting living spaces feature abundant natural light and elegant finishes throughout. The upgraded kitchen is perfect for both cooking and entertaining, while the spacious bedrooms offer comfort and tranquility. Step outside to a lovely yard with a recently installed privacy fence, ideal for family, pets, evening gatherings, or enjoying your morning coffee. This home offers the perfect combination of charm, comfort, and value. Dont miss the opportunity to make this beautifully upgraded Cape Cod your new home

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

There is so much potential for this 3 bedroom, 1 bath ranch, in need of a little updating, with attached carport located in Chester Harbor. There is a full unfinished basement and a 3 car detached garage all situated on 2 parcels that include 5 lots. Chester harbor offers water access to Rosin Creek

Nestled among the farmland and waterways in Kent County is a cul de sac of new homes on Bottom Road just outside of Chestertown. The new 2 bedroom/2 bath single family home in a quiet, serene enclave is a perfect spot for your new home! This fresh and modern home offers glossy granite counters, SS appliances, and a trendy color palette. The quality of this new construction shows in the engineered wood flooring and upgraded 5' baseboards and moldings. The primary bedroom is appointed with a walk-in closet and a shiny new full bath equipped with a double bowl sink/vanity. 1 additional bedroom adds options for an office or study. Enjoy the views of nature with your evening cocktail from the rear deck. Chestertown is a quaint, historic district on the Eastern Shore with an active art community and active boating society. The vast tributaries of the Chesapeake Bay and unspoiled land offer endless possibilities for hunting, fishing, kayaking, and canoeing. There is a front foot fee of $5,000

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

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

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