Chestertown MD Real Estate & Homes for Sale

Looking for that quiet location in a water access community? You will feel right at home in this 3 bedroom, 2 bath cape in Chesapeake Landing just minutes outside Chestertown and Rock Hall. From the front door to the back deck, the owners have taken great care and it shines through. Easy to maintain LVP flooring runs throughout the main floor. There's a bedroom and full bath as well as the kitchen with table space, dinging room with barn doors and a nice size living room, all located on the main floor. Two large bedrooms and hall bath are located on the second floor. Outdoors you will find a nice back yard for play and an abundance of parking including the electrical hook up for that RV. The storage shed is the perfect spot to keep the toys, lawn tools and equipment. Join the voluntary community association and enjoy the water access with the marinas and boat launch.

The BEST of in-town Chestertown living! Single level living in this open floor plan, custom built home. Gleaming hardwood floors, spacious primary suite with walk-in closet, large outdoor deck with fire pit patio, fully fenced back yard, wired for Talkie Fios internet, impeccably maintained. Two blocks from Washington College & Kent County Middle School, one block from Baily Park Dog Park & just steps from the walking loop, a short jaunt into Downtown Chestertown restaurants, shops, & the waterfront.

Whether you envision building your dream home or are seeking a hunting retreat, this secluded lot offers options. Situated on 42.598 acres of select cut woodland, this property is a nature lover's dream, offering endless outdoor recreation possibilities and abundant wildlife. Existing house and barns are tear downs, do not enter. Make it yours today!

Welcome to Your Forever Home! Step into luxury with over 3,000 sqft of living space, and that's just the beginning. As you explore this exquisite property, you'll discover an almost fully finished basement that adds an additional 1,300 sqft of potential. Upon entering, be greeted by the elegance of the entry level, which boasts an office, a charming dining room, a well-appointed kitchen, and a spacious Great room. Venture upstairs, where you'll find three generously sized bedrooms in one direction, and in the other, a massive primary bedroom that will sweep you off your feet. The grand primary bathroom and walk-in closet are sure to captivate you and make you feel right at home. But that's not all â head down to the almost fully finished basement, which could easily be a home of its own. With a game room, a comfortable bedroom, a well-appointed bathroom, and a cozy family room, it's the perfect space for an in-law suite. This is more than a house; it's a place where memories are made, and dreams come true. Welcome to your forever home.

This spacious Colonial home in Coventry Farms is within the town limits of Historical Chestertown in Kent County on the Eastern Shore of Maryland. Its location is conveniently located to many waterways for watercraft pleasure, marinas, public beach, dining, cultural activities and Washington College. The two-story open front foyer home of over 3000 SF offers an open floor plan which includes a sun room with an abundance of natural light overlooking the in-ground pool in the fenced rear yard. The home also offers a separate/formal dining room, finished rec room on the lower level and a 2-car attached garage. This three bedroom, two and one-half bath home is the perfect space for family and entertaining friends.

This contemporary waterfront property offers the perfect blend of modern living and waterfront serenity. The open floor plan affords views of Mill Creek from every room. The first floor features a three sided fireplace, a gorgeous great room with floor to ceiling windows/doors, gourmet kitchen which opens to the dining area, plus two bedrooms and two full baths. Upstairs you have a cozy loft area perfect for curling up with a book or for tv. There's also another bedroom and full bath and an office with a balcony looking over Mill Creek. Most of the furniture will convey! If you enjoy outdoor living this property is for you. There's a screened porch - the perfect setting for a crab feast! Plus a wrap around deck for relaxing and entertaining. The property includes private access to Mill Creek, making it perfect for boating, kayaking, and other water activities. And for those needing deeper water you will find Worton Creek Marina right around the bend! UPDATE: The health department has confirmed that it is possible to put a garage on the parcel where the septic system is located

Kent County Health Dept has no record of perc

Estate sale - Investor alert- major rehab needed - sold strictly AS IS - price to sell quickly- country location with in minutes of Chestertown - NO Well or Septic records on file - contact county for more information.

Great location, CLEAN & ready to go! Must have a minimum credit score of 635 & no delinquent accounts in the last two years. no more then 4 persons to occupy the home & preferably no pets. Anyone over the age of 18 living in the home must apply (application & credit check) and it's $30/person. You will be sent a quarterly statement to pay water and sewer directly to Landlord.

Custom built house on the East Fork of Langford Creek set on 8+ acres with a private dock. This is the first time the house has been for sale; original owners. It was built by Patrick Jones and designed by architects Dunning & Dunning from Swathmore, PA. Beautiful sunsets. It captures the lay out of the property and celebrates the water from every window. There is deep water (4.5 MLW, buyer to verify). 7-ton boat lift. Sunken living room with vaulted ceiling. White Oak floors through much of the house. Designed for outdoor living. There is a Deck, screened in porch, covered front porch. 2 car garage off the kitchen. Storage area above the garage with separate outside access. Huge basement, partially finished. Plenty of room for guests, a workshop, and a garage door for all the toys. Shown by appointment only. No drive by's please. High speed internet.

Nestled within the desirable community of College Heights, this charming Colonial-style home offers the perfect blend of classic design and modern convenience. Step inside to discover a well-designed floor plan that seamlessly integrates both form and function. The spacious living room features hardwood floors, large windows that flood the space with natural light, and a cozy fireplace that's perfect for chilly evenings. The updated kitchen offers an abundance of storage and prep space and opens to the formal dining room, both with original hardwood floors. Retreat to the three generous bedrooms, each designed to offer a peaceful haven for rest and relaxation. The master suite features a private bathroom two closets. This property also includes a two-car garage, dual zone heating and cooling, and a basement that offers ample storage space or potential for customization to fit your needs, as well as a screened back porch and large deck area, and a fenced back yard. This home has been lovingly cared for, with updates that blend seamlessly with its classic character. You'll find peace of mind in knowing that it's move-in ready.

Three bedroom ranch home in very desirable neighborhood. Located in between downtown Chestertown and the Country Club.

Come by this lovely BRAND NEW middle unit home in a Triplex in Historic Chestertown, available for move in in October. This home features Luxury Vinyl Flooring throughout, White Shaker Cabinets, Granite Counters, Spacious Living Room, Eat in Kitchen area, covered patio off the kitchen, spacious bedrooms including a large primary bedroom suite and much more! These homes are selling faster than they can be built, so come by today and take advantage of this opportunity while it lasts. There are only a few of these homes left ! Special financing programs available, including Zero Down payment loans and closing costs assistance programs so you can own this home for less than renting. Home is delivered at the asking price the way you see it in the photos with the exception of the siding color, which may be different.

Bask in the beauty of this incredible 1920s home in downtown Chestertown! At 2890 square feet, this freshly painted 5 bedroom, 3.5 bathroom property has tons of space and an oversized lot featuring a secluded backyard with mature trees, fire pit, and off-street parking, most of which are very rare to find downtown! The many updates include a brand new HVAC system and hot water heater; updated electric, new slider doors, cooktop, combination wall ovens, dishwasher, and 2nd floor bath fixtures along with a meticulously restored stairway in the entry hall. Other features include original hardwood floors on the first floor & stairway & newel post, some original windows, refinished floors on first floor, original hardwood floors on the second floor, freshly painted and repaired dormers, privacy fence, revitalized front door, and much more! Aside from the fantastic interior space, you'll fall in love with the charming front porch and lovely balcony off the second story primary bedroom. The exterior is further improved with new topsoil, grass seed, fertilizer, straw, and flowers. 204 N Mill is located on a quiet street close to downtown shops, Washington College, waterfront, restaurants, farmer's market and shopping. Whether a residence or an AirBnb, this home has endless possibilities!

Classic 2 story located in Chestertown Historic District steps away from downtown shopping and restaurants ! Deep back yard with large shade tree. Large kitchen, separate dining room, and front living room just off the front porch. 2 or 3 bedrooms possible. Very aggressive pricing for historic district !

MOVE IN READY!! Adorable, Affordable & 2 Blocks from the Chesapeake Bay! You don't want to miss this 2 Bedroom, 1 Bathroom home in Tolchester Estates! Featuring a Brand New Roof (2022), New Dishwasher (2023), New Washer (2022), beautifully updated, tiled Bathroom, lovely pergo wood flooring, bright & inviting Kitchen & cozy Family Room. Enjoy fishing or relaxing at the Private Community Beach or head over to Tolchester Marina & The Shanty Beach Bar right down the road for entertainment, dining and boating! Great location just 10 minutes from downtown Chestertown or Rock Hall, where you can enjoy tons of marinas, restaurants, shops & regular events! Not a thing to do but move in and enjoy everything this home and location has to offer! Whether this is your full time residence or 2nd home this adorable home has so much to offer! Come see for yourself!

This property is perc approved and ready for your fresh ideas. With 2 different zonings you can turn your dreams into a reality! This almost 6-acre parcel located on the corner of RT 544 and Pine Tree Rd has so many possibilities. With Suburban Estate and Village Center zoning here are just a few things you could envision on this large parcel of land. This property is approved for 2, you saw that right, 2 four-bedroom homes! Just think you could live in one, rent the other or have a mini family compound. Don't want to build 2 homes? That's okay the property also allows for a commercial zoning, ever thought of starting your own business? You could build your dream home and walk to your business all on the same property! But don't wait, properties like this don't come around often. Set your appointment to see this one today!

Priced To Sell Fast! Charming Updated 1 Level Rambler, Spacious Kitchen with QUARTZ Counters, Stainless Steel Appliances, Spacious Bedrooms, New Custom Paint, Updated Bathrooms, New Flooring, New Lighting, Fenced Backyard, Storage Shed, Much More!! Close to Schools, Shopping, and Commuter Routes. This Will Not Last!

INVESTOR ALERT!!! Bring all offers! You definitely want a property in the highly sought-after Chester Harbor community, located in historic Chestertown, home of Washington College! Portions of this community are waterfront and waterview. Use the beauty of your imagination to renovate this home into an income producing AirBnb, long-term rental, or to use as your vacation home oasis where you can enjoy kayaking or fishing at the pier! Very close to parks and recreation and a short ride to Centreville and Kingstown.

This charming three-bedroom rancher sounds like the perfect home for those who love to entertain guests. The split bedroom concept, open floor plan, and large backyard make it an excellent choice for hosting gatherings. The separate laundry room is a convenient feature, and the kitchen's great looking counters and island add a touch of elegance. The front door is located on the west/northwest side, and there is a ramp to the side door for easy accessibility. Plus, being just minutes from downtown historic Chestertown and historic Washington College makes this property an ideal location for those who appreciate history and culture. While it looks great, it's important to note that the property is being sold in as-is condition.

Build on almost an acre with the water & sewer allocation paid for & just steps away from the public ramp at Fairlee Creek! Trailer your toy & enjoy the perfect spot for tubing, skiing, wakeboarding, knee boarding, kayaking, paddle boarding, crabbing or whatever your heart desires. Great Oak Marina & Jelly Fish Joelâs sits at the head of the creek with easy access to the Chesapeake Bay! Enjoy the public beach where you can swim, eat, drink & listen to a band! Anchor out for the day or dock at Jellyâs! Rock Hall & Historic Chestertown are just a short drive away. * 45 minutes to Middletown DE * 1 hour to Easton MD * 1 hr 20 minutes to Philadelphia Airport * 1 hr 45 minutes to BWI Airport

THIS CHARMING HOME OFFERS A COZY LIVING SPACE THAT MAXIMIZES EFFICIENCY! Its modern 2023 renovations provide an inviting atmosphere with plenty of natural lighting throughout! The home features a primary bedroom with attached bath, kitchen with plenty of storage space, and a back yard patio, great for relaxing or entertaining! Minutes from local Rock Hall marinas, Waterman's Crab House, Harbor Shack, and other dining, this home is perfect for a full-time residence or vacation home.

21123 Montana Avenue is located in a Chesapeake Bay water oriented community on the Eastern Shore . You can make this a full time residence or your get away space. You have water views as you drive up and enter your driveway. In Tolchester Estates you will have access to the private community beach, boat ramp and you will be welcomed to the community center that holds a variety of events through out the year. All ready to move into and you can be in to enjoy the Fall season. This home offers a split floor plan. Main bedroom and full bath on the left as you come in the front door and then two bedrooms and full bath to the right. Open living room, kitchen, eat in kitchen and extended bar for stools. Out back you have a deck and the back door where you can enter into the mud room/laundry room. The screen porch will let you relax looking out into a nice size private back yard with mature trees and deer to watch. Home is being sold as is.

One of the last buildable lots in Chestertown with public sewer and water hookup available. Cleared and ready to build your dream home. No historic district regulations. Rear lot line was adjusted in 2021 allowing 16 more feet to build behind the beautiful Japanese Maple tree. Just a few minutes walk to the heart of downtown. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Wonder at the historic architecture and enjoy local shopping, restaurants, art galleries, music stores, and waterfront walkways and parks. Chestertown is home to many festivals and the local Farmer's Market on Saturdays. 30 minutes to Middletown, Delaware and tax-free shopping. 90 minutes to Baltimore and/or Washington, D.C. 60 minutes to Philadelphia. 90 minutes to Delaware Beaches. Survey from 2021 on file.

Chesapeake Landing has a voluntary Home Owners Association which offers access to Worton Creek. Parcel has failed perc.