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24607 Chestertown Rd, Chestertown
$365,000
3 Beds ⋅ 3 Baths
Enjoy the best of both worlds with this well-maintained home situated on a generous 0.653-acre lot just outside of Chestertown! Offering the space and privacy of country living while remaining just minutes from downtown amenities, this 3-bedroom, 2.5-bath home has plenty to offer. **A brand-new well and septic system have just been installed**, providing an important recent improvement for the next owner. Inside, you'll find a welcoming entryway, formal dining room, and spacious kitchen featuring an island, gas cooktop, and cozy breakfast nook. The dedicated laundry room offers convenient access to the side yard, while the comfortable living room provides a warm gathering space centered around a working fireplace. A mix of wood, tile, and carpet flooring adds character throughout the home, and two bathrooms have been recently updated. Outside, enjoy the expansive backyard with room to relax, entertain, or simply take in the extra space. The detached two-car garage offers additional flexibility with a separate area ideal for a workshop, home office, or hobby space, along with a loft ready for your ideas. With a new well and septic system and a convenient location just outside of town, this property offers space, versatility, and the opportunity to enjoy Eastern Shore living close to everything Chestertown has to offer!

24607 Chestertown Rd, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

8901 S Bayview Dr, Chestertown
$525,000
3 Beds ⋅ 3 Baths
The Perfect Maryland Retreat with Chesapeake Bay Views Close By. Experience the quality of a custom-built Cape Cod crafted by a reputable local builder. Lovingly maintained by its original owner, this home is completely move-in ready and features a freshly painted interior throughout. Whether you are looking for a full-time residence, a weekend getaway, or a holiday retreat, this property offers a peaceful escape. The home features a Chestertown address but sits closer to Rock Hall, giving you the absolute best of both worlds. You are perfectly positioned to enjoy the vibrant Rock Hall festivities and marinas, while still being just a short drive from the famous Chestertown Farmers Market and Historic Downtown, with their variety of Festivals and events throughout the Year. Arrive via the welcoming, roomy front porch, an inviting space to sit, relax, and take in the quiet surroundings. Inside, the main level features an open floor plan where the living room, anchored by a cozy propane fireplace, flows beautifully into the dining area to make the space feel inviting and roomy. The eat-in kitchen opens directly onto a back deck, making outdoor grilling and relaxation easy. The highly sought-after primary bedroom is conveniently located on the main level for easy first-floor living. Upstairs includes additional bedrooms, plenty of easy-access storage space, and a versatile, fully finished bonus room over the garage with a convenient interior entrance—ideal for a home office, hobby room, or guest suite. For hobbies and storage, the property excels. The oversized garage offers ample room for parking plus a dedicated project/workshop space. Below, a partial walk-out basement provides exterior access, making it incredibly easy to store gear or access the home's systems. Situated in a desirable water-oriented community, you will enjoy peekaboo views of the Chesapeake Bay right from the house. Best of all, the neighborhood features its own small private beach for easy enjoyment, making it effortless to relax by the water and perfect for collecting sea glass, beachcombing, and watching the sunset. This classic, beautifully refreshed home is ready for its next chapter!

8901 S Bayview Dr, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

21338 Virginia Ave, Chestertown
$400,000
2 Beds ⋅ 2 Baths
Nestled in the quiet Tolchester Estates, this charming new construction home, completed in 2026, embodies the pinnacle of low maintenance living. This well-built ranch-style residence offers a harmonious blend of modern living space and coastal charm, perfectly situated approximately 800 feet from the breathtaking Chesapeake Bay. Step inside to discover an open-concept layout that seamlessly integrates the kitchen, dining, and living areas, creating an inviting space ideal for both entertaining and everyday living. The interior features luxury vinyl plank flooring that exudes sophistication while ensuring durability and ease of maintenance. The thoughtfully designed kitchen is a cook's dream, equipped with new appliances including a built-in microwave, dishwasher, stove, and refrigerator, all complemented by a sleek exhaust fan. The combination of functionality and style makes this kitchen the heart of the home. With two spacious bedrooms and a beautifully appointed full bathroom, this residence offers comfort and privacy. The main floor laundry adds convenience to your daily routine, while the attached side-entry garage provides easy access and additional storage options. Step outside onto the expansive deck, where you can bask in the serene views of the bay, perfect for morning coffee or evening gatherings under the stars. The outdoor space is an extension of the easy lifestyle this home offers, allowing you to enjoy the tranquility of nature right at your doorstep. The property is not just a home; it's a lifestyle. Living in Tolchester Estates means embracing a community that values both privacy and connection, with the Chesapeake Bay as your backdrop. Enjoy leisurely strolls along the water, or indulge in water-oriented activities that the bay has to offer. This home is designed for those who appreciate easy living, with a commitment to quality evident in every detail. From the excellent condition of the property to the thoughtful selection of materials, this residence is a jewel. Don't miss the opportunity to own a piece of paradise in this exclusive bay block location. Experience the luxury, comfort, and lifestyle that await you in this remarkable home. Your dream of coastal living starts here. Within 5 minutes of a full-service marina and "The Shanty" for fun entertainment located on a beach right in front of the Chesapeake Bay. There are also community beaches, one is about two minutes from this cottage!

21338 Virginia Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

106 Harlan Loop, Chestertown
$425,000
4 Beds ⋅ 3 Baths
Nestled in Coventry Farms II, this exquisite Colonial-style residence offers a harmonious blend of Space, Convenience and comfort, perfect for those who appreciate the finer things in life. Built in 2009, this stunning home boasts 3,165 square feet of meticulously designed living space, ensuring ample room for both relaxation and entertainment. Step inside to discover an inviting interior adorned with high-end finishes and thoughtful details. The spacious family room, seamlessly connected to the kitchen, is perfect for gatherings, while the formal dining room sets the stage for elegant dinner parties. The gourmet kitchen is a chef's dream, featuring a generous island, stainless steel appliances, and a convenient pantry, all bathed in natural light from the double-pane windows. Enjoy casual meals in the cozy breakfast area, where morning sunlight creates a warm ambiance. Retreat to the luxurious primary suite, complete with a walk-in closet with an additional closet and a spa-like bathroom featuring a walk-in shower and double sinks. Each of the additional three bedrooms offers generous space and comfort and large closets, ensuring everyone has their own sanctuary. Recessed lighting and ceiling fans throughout enhance the home's inviting atmosphere, while plush carpeting and laminate flooring provide a perfect balance of style and practicality. The partially finished basement offers endless possibilities, whether you envision a home theater, gym, or additional living space. The basement even has a rough in for an additional bathroom. With interior access and heating, this area is ready to be transformed into your personal oasis. Outside, the property sits on a 0.28-acre lot that backs to serene trees, while the front over looks the large common area providing a tranquil backdrop for outdoor living. The expansive deck invites you to unwind and entertain, while the attached garage and ample driveway space accommodate all your vehicles with ease. This home is not just a residence; it's a lifestyle. Enjoy the peace of mind that comes with living in a well-established community, where every detail has been considered for your comfort and enjoyment. Experience the perfect blend of luxury, convenience, and nature in this exceptional Coventry Farms II gem that is "Move In Ready". Enjoy a walk in Downtown Historical Chestertown which is on the Chester River. Explore many events that the town has such as Saturday morning Farmers Markets, The Annual Tea Party, Downrigging Festival, Fourth of July Fireworks, tours on the Sultana and River Packet and Dickens of a Christmas or just relax on a bench by the River or Wilmer Park. Don't miss the opportunity to make this dream home your reality! Chestertown is a great place to call Home!

106 Harlan Loop, Chestertown

Listing courtesy of Douglas Realty LLC. Contact:

8986 Orchard Dr, Chestertown
$679,900
3 Beds ⋅ 4 Baths
Welcome to 8986 Orchard Drive, tucked away in the sought-after Orchard Hill neighborhood just outside of Chestertown! This move-in-ready home offers comfortable one-level living with 3 bedrooms, 2 bathrooms, and a partially finished basement with endless possibilities. Enjoy a spacious living room with recessed ceilings, an inviting primary suite with a jetted soaking tub, and updates throughout, including a new roof in 2025 and an efficient HVAC system upgraded in 2022. The partially finished basement features a private, ground-level walkout entrance, studio-style living space with a pool table, an efficient mini-split system, and plenty of additional storage or workshop space. French drains and an automatic sump pump add peace of mind. Outside, enjoy multiple spaces to relax and entertain, including a screened-in porch, open deck, patio with a hot tub that conveys, and a partially fenced backyard surrounded by beautiful crepe myrtles. Additional highlights include a two-car garage, a large floored attic for extra storage, and a solar system installed in August 2025. Conveniently located within 10 minutes of Chestertown's everyday amenities, shopping, dining, and more, this property offers the perfect blend of comfort, flexibility, and convenience. Come see all that this home has to offer! *Sellers offering credit towards painting*

8986 Orchard Dr, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

234 N Kent St, Chestertown
$325,000
5 Beds ⋅ 2 Baths
Some houses are finished. This one is full of opportunity. Built circa 1920, this Victorian sits in one of Downtown Chestertown's most desirable neighborhoods — and it's waiting for someone who can see what it is meant to become. The hard work and the expensive work have already been done: new cedar siding, blown-in insulation, and original hardwood floors throughout. What remains is the fun part. The kitchen and baths are a genuine blank slate, ready for your design, your finishes, your vision. And the bones… remarkable. Solid construction, generous proportions, and historic detail at every turn — the kind of craftsmanship that simply isn't built anymore, and can't be bought back once it's gone. Start with a house of real character and your renovation adds value instead of merely keeping up. Upstairs, five generous bedroom and two full baths. A rare third-floor primary suite offers space and privacy set apart from the rest of the home — a true owner's retreat, a guest wing, or a quiet work-from-home floor of its own. Outside, a fully fenced backyard is ready for pets, play, and entertaining, a large shed could easily become a garage, studio, or workshop. The driveway provides off-street parking, a definite bonus for Chestertown. And the location is the whole point. You're roughly three blocks from everything Chestertown offers — the shops, restaurants and galleries along High Street, the Chester River waterfront, the farmers market, and the historic charm of one of the Eastern Shore's best-loved small towns. Bring your contractor, or be your own. Come see the possibility.

234 N Kent St, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact:

8820 Cumberland St, Chestertown
$312,500
3 Beds ⋅ 2 Baths
Discover relaxed Eastern Shore living at 8820 Cumberland Street, a charming three-bedroom, two-full-bath home offering the ease and convenience of single-level living in the peaceful water-privileged community of Tolchester Beach. Built in 2006, this inviting residence combines a comfortable floor plan, desirable outdoor space, and an attached two-car garage with a setting that encourages you to slow down and enjoy the best of Maryland's Eastern Shore. The thoughtfully designed interior provides an easy flow for everyday living, with three well-proportioned bedrooms and two full baths all conveniently located on one level. Whether you're entertaining, working from home, or simply enjoying a quiet evening, the home's practical layout offers flexibility for a variety of lifestyles. Step outside to the rear deck, where a wooded backdrop creates a tranquil setting for morning coffee, outdoor dining, or relaxing at the end of the day. The surrounding natural scenery adds a welcome sense of privacy and peacefulness. The community's water-oriented amenities add to the appeal, with opportunities to enjoy the community beach, fishing, local marina, and the laid-back lifestyle that makes the Eastern Shore so desirable. Ideally positioned between historic Chestertown and waterfront Rock Hall, the home places shopping, dining, marinas, boating, and local recreation within convenient reach. Whether you're seeking a full-time residence, weekend retreat, or low-maintenance Eastern Shore escape, 8820 Cumberland Street offers an appealing blend of comfort, convenience, and coastal lifestyle. This property is being sold as-is, property is lender-owned and U.S. Bank National Association is making no representations or warranties. U.S. Bank National Association may have financing options available.

8820 Cumberland St, Chestertown

Listing courtesy of RE/MAX Advantage Realty. Contact:

Little Harbor Way Unit 1, Chestertown
$1,800,000
4 Beds ⋅ 4 Baths
**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.

Little Harbor Way Unit 1, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

103 Metcalf Rd, Chestertown
$259,900
3 Beds ⋅ 3 Baths
Ask about our SELLER-PAID RATE BUYDOWN — the builder is paying to permanently lower your interest rate when you finance with our preferred lender, who is also contributing toward your closing costs. The result: a dramatically lower monthly payment on a brand-new home, saving you well over a hundred dollars every month — even more on lower-down-payment financing. This is real payment relief in today's market — often the difference between watching and owning. Brand-new construction in the heart of Chestertown. Buydown applies with use of preferred lender; see agent for details. 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 you’ll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Additional highlights include exclusive financing opportunities with zero down payment loans, paid closing cost programs, and discounted interest rates—making it possible to own this home for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown’s most historic locations. Ask about Special Financing Offers and how to get $7,500 or more in closing help from the builder's preferred lender and on select models, while they last!

103 Metcalf Rd, Chestertown

Listing courtesy of Real Broker, LLC - Chester. Contact:

896 Washington Ave, Chestertown
$325,000
A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial. Fully finished basement. Plenty of parking. A great place for a centrally located home or office.

896 Washington Ave, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

10 Cedar Chase Ct, Chestertown
$495,000
3 Beds ⋅ 3 Baths
Beautiful waterviews of the Chester River set the stage for this special Chestertown property, located in desirable Mile Tree Village and just a short walk from the Historic District. Set on .53 acres, the home offers 1,656 square feet of finished living space on the main level, with 3 bedrooms and 2 full baths, plus an unfinished lower level with a half bath and one-and-a-half-car garage. An upper-level deck, accessible from the living room, dining room, and primary suite, provides the perfect spot to enjoy the river views and the easy Eastern Shore lifestyle. The home is ready for a fresh vision and offers tremendous potential to become a luxury waterview residence. Thoughtful updating could transform the existing spaces into a home that takes full advantage of the setting. Within a short walk or bike ride to Chestertown's Historic District for dinner, shopping, galleries, and Annual Festivals, while the Chester River provides a beautiful backdrop to everyday life. Bring your vision and create a truly special waterview home and experience the Eastern Shore Lifestyle at its finest!

10 Cedar Chase Ct, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

6324 Quaker Neck Rd, Chestertown
$2,895,000
5 Beds ⋅ 4 Baths
Discover 6324 Quaker Neck Road, an exceptional waterfront estate spanning over 5 acres along the East Fork of Langford Creek offering over 5 feet of water at low tide. Over 5,900 square feet of refined living space with 5 bedrooms and 4 baths, designed for elegant Shore entertaining and everyday ease. A new private pier with swim platform and boat lift, plus your private beach, extends living outdoors — complemented by a detached garage with carriage house and a pole building. Minutes to Chestertown, yet quietly removed — a distinguished Quaker Neck offering for the buyer who wants it all.

6324 Quaker Neck Rd, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

22974 Bay Shore Rd, Chestertown
$315,000
2 Beds ⋅ 2 Baths
Welcome to this charming farmhouse-style home in Fairlee! Completely renovated in 2023, this home is move-in ready and offers a comfortable mix of modern updates and farmhouse charm. Inside, you’ll find an open floor plan with luxury vinyl plank flooring throughout the main living areas. The living room offers a cozy space to relax and unwind. The updated kitchen is the heart of the home and features beautiful finishes and newer appliances, making it a great space for cooking and gathering. The home features two bedrooms, including a spacious primary bedroom, and two full bathrooms that have both been nicely updated. The spacious laundry room/mudroom provides plenty of room and adds everyday convenience. Enjoy your morning coffee or unwind at the end of the day on the inviting front porch, a great spot to sit back and enjoy the peaceful surroundings. Outside, you’ll find a large half-acre lot that backs to farmland, offering a beautiful setting. There’s plenty of room to enjoy the outdoors, garden, or let the kids and pets play. The gravel driveway provides parking for up to four vehicles. If you’re looking for a home that has been beautifully updated while still keeping that cozy farmhouse feel, this one is worth a look. Come see everything this Fairlee home has to offer!

22974 Bay Shore Rd, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

105 N Water St Unit 3, Chestertown
$459,000
2 Beds ⋅ 2 Baths
Second story, waterfront condo in historic Chestertown. Comes with a private boat slip at the end of the dock. 2 bedrooms and 2 full baths. Spacious patio with a stunning view of the Chester River. One of the most coveted streets in historic Chestertown!

105 N Water St Unit 3, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

8732 Elm Rd, Chestertown
$289,000
3 Beds ⋅ 2 Baths
Located in Tolchester Estates, this well maintained ranch style home sits on a lovely tree shaded lot. There are three bedrooms, two bathrooms and an open kitchen, dining and living room area. The back deck with a built in bench is just perfect for relaxing, entertaining and watching the abundant wildlife. This water oriented, water access community offers a community beach on the Chesapeake Bay, a boat ramp and a community hall for gatherings and events. Tolchester Marina, a full service operation, and The Shanty Beach Bar, "Best Kept Secret on the Bay", are just a short walk or golf cart ride away. This low maintenance home can easily be a primary resident, second home or investment property. Enjoy the easy pace and the stunning sunsets this community has to offer (some interior images were virtually staged using AI - these images do not represent the property's current furnishings or decor).

8732 Elm Rd, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

104 Maple Ave, Chestertown
$1,050,000

104 Maple Ave, Chestertown

Listing courtesy of Real Broker, LLC - Annapolis. Contact:

329 Union Church Rd, Chestertown
$549,900
4 Beds ⋅ 3 Baths
Opportunities like this don't come along every day! Welcome to 329 Union Church Road, tucked away in a highly sought-after neighborhood in Queen Anne’s County where homes rarely become available.—a home with plenty of space, useful updates, and room to truly make it your own! Situated on just over an acre, this 4-bedroom, 2.5-bath home offers 2,464 square feet of living space, a paved driveway, attached garage, and a large detached pole barn with loft—providing plenty of room for storage, hobbies, a workshop, or all the extras. Inside, you’ll find a spacious and functional layout ready for its next owners to settle in and make it feel like home. The kitchen features updated appliances, including a new refrigerator, new stove, microwave, oven, and dishwasher in 2026, while new LVP flooring upstairs adds a fresh look. All toilets throughout the home have also been replaced. Major mechanical updates include the upstairs HVAC system replaced in 2023 and the downstairs HVAC system replaced in 2026. The crawlspace has also been professionally serviced by DriGuys Restoration, including the installation of a new vapor barrier. The completed work comes with a transferable one-year warranty, providing additional peace of mind for the next owners. Outside, the 1.03-acre property gives you room to spread out, enjoy the outdoors, and create a space that fits the way you want to live. The detached pole barn adds even more versatility, while the attached and detached garage spaces provide plenty of options for parking, storage, projects, and more. Additional features include a tankless gas water heater, private well and septic, and an owned water-filtration system. Whether you’re looking for more room inside, space for your hobbies and projects, or simply a place you can put your own stamp on, 329 Union Church Road offers the space and flexibility to make it your own. Come take a look and imagine making this Queen Anne’s County property your next home!

329 Union Church Rd, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

Chestertown
$695,000
Rarely do vacant parcels like this become available so close to historic Chestertown! Offering approximately 43 acres, this exceptional property presents a unique opportunity to create your own private estate while enjoying outstanding recreational and hunting opportunities. The current owners have strategically developed and maintained the property for exceptional deer and turkey hunting through their partnership with HuntingPlots.com. Thoughtful habitat and land management includes established travel corridors, bedding areas, food plots, an artificial water pond, and carefully planned tree management, creating an ideal environment for wildlife. The property is subject to a Maryland Environmental Trust conservation easement; however, the easement permits the construction of one homestead, offering the opportunity to build a private residence surrounded by acreage and natural beauty. Please refer to the Kent County Health Department percolation letter and additional easement information included in the documents. Location is truly a standout feature of this rare offering. Situated within approximately 1.5 miles of downtown Chestertown, the property provides convenient access to Chester River boat ramps, Washington College, the Chester River Yacht & Country Club, shopping, dining, and all that Chestertown has to offer. Included are 3 Ten Point box deer stands, several tacticam deer cameras, and several other ladder stands. A rare combination of acreage, privacy, recreational value, and proximity to town, an exceptional opportunity on Maryland’s Upper Eastern Shore.

Chestertown

Listing courtesy of Select Land & Homes, LLC. Contact:

Towhee Road, Chestertown
$40,000
This property, situated on a 0.55-acre lot, offers a blank canvas for your vision. Located in Kent County, this property presents endless possibilities for the right buyer. Take advantage of the spacious lot size, perfect for outdoor activities or future expansion plans. Buyers are encouraged to perform their own due diligence to verify property details.

Towhee Road, Chestertown

Listing courtesy of The Parker Group. Contact:

7415 Wilkins Ln, Chestertown
$222,000
3 Beds ⋅ 1 Baths
This 3-bedroom, 1-bathroom ranch-style home in Quaker Estates offers a solid investment opportunity with a total finished area of 936 sq ft. Built in 1963, the property features essential appliances including a refrigerator and stove, ensuring immediate functionality for tenants or future buyers. The average condition of the home allows for potential value-add renovations, which can significantly increase rental income or resale value. The spacious 0.34-acre lot provides ample outdoor space, while off-street and driveway parking enhances convenience for residents. A shed on the property offers additional storage options, appealing to renters seeking practicality. With no pool maintenance costs and a straightforward layout, this property is low-maintenance, making it an attractive option for investors looking to maximize returns. The combination of location, features, and potential for appreciation makes this property a compelling addition to any real estate portfolio.

7415 Wilkins Ln, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

24775 Langford Rd, Chestertown
$305,000
3 Beds ⋅ 1 Baths
PRICE IMPROVEMENT!! Here is 24775 Langford Road, a well-maintained 3-bedroom, 1-bath home situated on 1.27 acres in a peaceful country setting just minutes from downtown Chestertown. The property features a spacious two to three-car detached garage/workshop, offering plenty of room for vehicles, storage, hobbies, or projects. A large Trex deck provides additional outdoor living and entertaining space. The home underwent extensive renovations in 2018, including the roof, windows, siding, gutters, storm doors, HVAC system, the Well was done in 2021, and partial crawl space encapsulation. Interior improvements included refinishing of the original hardwood floors and a remodeled kitchen featuring all-wood cherry cabinetry and stainless-steel appliances. With numerous major improvements already completed, garage and workshop space, and over an acre of property, this home offers comfortable country living with convenient access to Chestertown, Rock Hall and surrounding areas. Call to set up an appointment!

24775 Langford Rd, Chestertown

Listing courtesy of RE/MAX Chesapeake. Contact:

104 Lincoln Dr, Chestertown
$275,000
3 Beds ⋅ 1 Baths
**NEW PRICE! MOTIVATED SELLER WILLING TO CONSIDER BUYER CLOSING COST ASSISTANCE OR INTEREST RATE BUYDOWN!** Here's an opportunity worth a second look! With a fresh price improvement and a seller ready to make a move, now is the time to explore the possibilities. Imagine settling into your new home before the holidays and potentially making your first mortgage payment in 2027! This charming Chestertown rancher offers bright, updated interiors, comfortable single-level living, a spacious corner lot, newer paver patio, fenced backyard and no community HOA. Whether you're purchasing your first home, looking to simplify or searching for an easy-to-maintain property, there's plenty to love here. Schedule your tour, bring your offer and let's make a move!

104 Lincoln Dr, Chestertown

Listing courtesy of RE/MAX Executive. Contact:

300 And 302 S Mill St, Chestertown
$1,195,000
Remarkable 1 acre downtown Chestertown development opportunity outside the Historic District. Incredible potential for a builder or a unique property for a private homesite. Directly adjacent to the Chestertown walking rail trail and just steps from downtown Chestertown while overlooking the Lawrence Wetland Preserve, rolling meadows and Radcliffe Creek behind. Sale includes two parcels - 300 S Mill (.55 acres) and 302 S Mill (.55 acres) - totaling approximately 1 acre. 300 is unimproved and 302 has a 1960s brick home on it. R:6 Traditional Neighborhood Development Zoning permits a wide range of dense residential development opportunities. Maximum residential density is limited to 42 bedrooms which could be single family homes, multi-family, apartments, townhouses, rowhouses, condos, and others. Smaller commercial options available as well. Public water and sewer is on site and additional allocations are available. Entire site is usable. Property is partially wooded with several large mature Oak Trees. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market. Additional information available upon request. Buyer to perform own due diligence. Do not enter property without an appointment.

300 And 302 S Mill St, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

212 Washington Ave, Chestertown
$675,000
5 Beds ⋅ 3 Baths
This charming American Four Square has been meticulously maintained and is located 1 block from Washington College’s campus and near Chestertown’s Historic District’s shops and restaurants. All of the key features of this architectural style are evident - two and a half stories high, hipped slate roof with a distinctive dormer at the front of the house, spacious four-room plan and full front porch with mahogany flooring with a depth that makes it a wonderful outdoor room. The American Four-Square was designed for narrow urban lots and this property’s bonus is its deep lot that easily accommodated an addition of a kitchen-family room opening onto a deck and a deep rear fully fenced back yard that offers safe play for children and pets. Another bonus is a two-car garage. From the foyer, the “U” shaped artisan stair rises to the third floor and the main floor’s living room, dining room, bathroom and library are seamlessly connected to maximize the rooms’ sizes. The rear addition of an open plan kitchen-family room has easy indoor-outdoor flow to the adjacent deck. The second floor contains 3 bedrooms and 2 full baths as well as the laundry. The third floor contains two additional bedrooms. Throughout the house, details of original wood floors, moldings and trim, corner guards and bespoke millwork evoke an earlier era of gracious living. A uniquely American architectural style, with an addition and updates for today’s family lifestyle; freshly painted exterior, meticulous mature landscaping, fenced rear yard that is a verdant oasis, two-car garage - who could ask for anything more?

212 Washington Ave, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

8184 Rock Hall Rd, Chestertown
$38,200,000
4 Beds ⋅ 2 Baths
Tulip Forest, a farm defined by scale, stewardship, and long-term value. Recognized as a premier sporting estate, this legacy holding property is the kind of asset that seldom comes to market on Maryland's Upper Eastern Shore. 1,054 +/- acres held intact under one ownership: 680 tillable acres, 272 acres of timber, 5 ponds, 3 impoundments, 26.75-acre wetlands restoration project, 45 acres CRP, a 3.75 mile interior gravel road system, 3 residences, and multiple farm outbuildings. At its center stands Caulk's Field House, circa 1743, a remarkably preserved residence on the ground recognized among Maryland's best-preserved War of 1812 sites. Nearly four miles of farm roads reach every corner of the property, and the ponds, impoundments, and mature timber hold waterfowl, whitetail and countless other game species. Also included beyond the farming operation: 7 acres zoned commercial, additional parcels zoned Village, and four sewer allocations secured along Georgetown Road. A working farm today, with room to grow, suited to farmers, sportsmen, conservation buyers, and investors.

8184 Rock Hall Rd, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

300 And 302 S Mill St, Chestertown
$1,195,000
2 Beds ⋅ 1 Baths
Remarkable 1 acre downtown Chestertown development opportunity outside the Historic District. Incredible potential for a builder or a unique property for a private homesite. Directly adjacent to the Chestertown walking rail trail and just steps from downtown Chestertown while overlooking the Lawrence Wetland Preserve, rolling meadows and Radcliffe Creek behind. Sale includes two parcels - 300 S Mill (.55 acres) and 302 S Mill (.45 acres) - totaling 1 acre. 300 is unimproved and 302 has a 1960s brick home on it. R:6 Traditional Neighborhood Development Zoning permits a wide range of dense residential development opportunities. Maximum residential density is limited to 42 bedrooms which could be single family homes, multi-family, apartments, townhouses, rowhouses, condos, and others. Smaller commercial options available as well. Public water and sewer is on site and additional allocations are available. Entire site is usable. Property is partially wooded with several large mature Oak Trees. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market. Additional information available upon request. Buyer to perform own due diligence. Do not enter property without an appointment.

300 And 302 S Mill St, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

123 Trafford Dr, Chestertown
$370,000
4 Beds ⋅ 3 Baths
Space, convenience, and value just minutes from downtown Chestertown! This spacious 4-bedroom, 2.5-bath Colonial in Coventry Farms checks the boxes for buyers looking for room to spread out without giving up convenience. The main level features a comfortable living room, dining area, kitchen, and half bath. Upstairs, you’ll find four bedrooms, including a spacious primary suite with a walk-in closet and en suite bath with dual vanities. Need even more space? The mostly finished basement adds approximately 600 sq. ft. of flexible living space. Plus the attached two car garage with plenty of room to park your vehicle and still have storage space. Outside, enjoy a stamped-concrete patio and fenced backyard—perfect for relaxing and entertaining. Recent updates include HVAC replaced in 2021, upgraded bathrooms, and additional cabinets and counter space in the kitchen. Just under 2 miles from historic downtown Chestertown, you’ll be close to restaurants, shopping, festivals, walking trail, the waterfront park, and everything town has to offer.

123 Trafford Dr, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

115 Chester Arms Dr, Chestertown
$259,000
3 Beds ⋅ 2 Baths
Welcome to 115 Chester Arms in Chestertown, MD! This 3-bedroom, 2-bath home offers a comfortable and functional layout with plenty of potential to make it your own. The home provides a nice combination of living space, comfortable bedrooms, and the convenience of two full bathrooms. Whether you're a first-time buyer, looking to downsize, or simply searching for a home in the Chestertown area, this property is worth a look. Conveniently located near downtown Chestertown, local shopping, dining, and everyday amenities. Some listing photos have been digitally enhanced for presentation purposes. Certain furnishings and décor may have been virtually modified or added. No material structural features of the property have been altered

115 Chester Arms Dr, Chestertown

Listing courtesy of Samson Properties. Contact:

101 S College Ave, Chestertown
$359,000
2 Beds ⋅ 2 Baths
This lovely 1920 Chestertown colonial is full of character, charm and artistic detail. Thoughtfully updated, the home offers a bright, open floor plan that highlights its handcrafted touches. The living room features re-stored hardwood floors and a cozy gas fireplace, creating a warm cozy space. Natural light pours into the open and airy kitchen with newer painted cabinets, stenciled floors, shiplap walls, and a laundry/half bath just off kitchen. From the kitchen step straight into the private fenced courtyard, your own peaceful retreat. With a large brick patio, privacy plantings, and ample garden space to create your own haven. Upstairs you'll find two nice sized bedrooms, re-finished hardwood floors and a good size full bath with walk in shower. If you're looking for that quiet oasis in a downtown location, this is it!

101 S College Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Cannon Street, Chestertown
$281,000
Significant price correction! Package offering for two adjacent lots in historic Chestertown. The combined package is for over a quarter of an acre, zoned R-5, within walking distance of downtown Chestertown. The convenient in-town location offers excellent potential for development, with the opportunity to build a single family home, townhouses or apartments. Plans available for proposed townhouses. Backing up to the Rail Trail, this lot enjoys easy access to local shops, restaurants, waterfront activities, and all that historic Chestertown has to offer. Water and sewer hookups available. No property address has yet been assigned to the 9,381 sq ft lot; the 3,097 parcel is designated as 620 Cannon Street. Buyer to verify zoning, permitted uses, building requirements, and utility availability. Each lot is listed separately in separate listings.

Cannon Street, Chestertown

Listing courtesy of Taylor Properties. Contact:

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