Chestertown Real Estate

Chestertown Real Estate

Welcome to Chestertown, Maryland – a picturesque gem nestled along the banks of the Chester River. This charming town, founded in the 18th century, boasts a rich tapestry of history, culture, and natural beauty. With its tree-lined streets, historic architecture, and vibrant waterfront, Chestertown is a delightful blend of small-town charm and modern amenities.

As you stroll through the town, you’ll discover a variety of boutique shops, art galleries, and cozy cafes, each offering a unique taste of local flavor. The annual Chestertown Tea Party Festival, celebrating the town's revolutionary history, draws visitors from near and far, showcasing the community's spirit and creativity.

Nature enthusiasts will find solace in the scenic beauty surrounding Chestertown. The nearby Chesapeake Bay offers ample opportunities for boating, fishing, and kayaking, while the lush landscapes invite hiking and biking adventures. The town is also home to Washington College, a liberal arts institution that enriches the community with cultural events and academic pursuits.

Chestertown’s location provides easy access to major cities like Baltimore and Washington, D.C., while maintaining its serene, rural charm. With a strong sense of community and a commitment to preserving its historic roots, Chestertown is not just a place to live; it’s a place to thrive. Whether you’re looking for a serene retreat or an active lifestyle, Chestertown welcomes you with open arms. Come explore the possibilities and discover why so many have chosen to call this enchanting town home!

Newest Listings in Chestertown

$659,999
3 Beds ⋅ 4 Baths
Live where you play at 7712 Waterview Lane in sought-after Country Club Estates. Situated on just under an acre of land, this wonderfully renovated and well-maintained cape cod is a quick bike ride to downtown Chestertown or an easy walk to the Chester River Yacht and Country Club. Timeless interior features, a main floor primary suite and practical indoor / outdoor living spaces make this the perfect home for everyday living or a weekend retreat. The well-designed first floor - featuring hardwoods, and baseboard and crown moldings throughout - is anchored by the open concept kitchen and living room spaces which flow naturally to the back sunroom and exterior deck. The renovated kitchen now features solid wood cabinets, quartz countertops, stainless steel appliances, recessed lighting, and overhanging bar seating. Cozy up with a book by the living room brick fireplace with propane insert encircled by classic built-in bookshelves. Passing through the back sliding doors you will be greeted by the sunroom and oversized back deck: each perfect for crab feasts and summer bbq's. Enjoy summer evenings while overlooking the private backyard which is fully fenced-in and has plenty of space for dogs and children. Further complementing the main floor is the primary bedroom with an ensuite bath and a large walk-in closet. The renovated primary bath now features ceramic tile, a standing stall shower, wainscoting, double vanity, and new lights and toilet. A dining room off the kitchen with a lovely bay window flows through a pocket door into the formal living room with built-in bookcases. The main floor is finished by a renovated powder room and laundry room just off the kitchen. Moving upstairs one will find two more generously sized bedrooms, a full shared bath and a potential 4th bedroom or office space for those that can work from home. An attached two-car garage has another half bat and additional storage and work spaces for those that like to tinker. Mature trees provide lots of shade and privacy around the meticulously maintained front and back yards: A generously sized storage shed is perfect for garden tools and the lawnmower. Located on a quiet, dead-end street; the neighborhood is great for dog walkers and evening strolls. Improvements made by current owner: whole kitchen remodel including cabinets, countertops, appliances, hardwood floors (2019); primary bathroom and powder room remodel including ceramic tile, standing shower stall, toilets, wainscoting, double vanity, fixtures (2017), 14 windows replaced with double-pane insulated (2017); Carrier HVAC (2017); whole house water filter and well pressure tank (2022); crawl space improvement (2016); and professional landscaping. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic architecture, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market and a laid back lifestyle with an endless number of social or volunteer activities. Less than 90 minutes to Washington D.C. or Philadelphia. Enjoy country living on the Eastern Shore. Professional photos to come!

7712 Waterview Ln, Chestertown

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

$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.

8732 Elm Rd, Chestertown

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

$1,050,000

104 Maple Ave, Chestertown

Listing courtesy of Real Broker, LLC - Annapolis. Contact: 8554500442
$1,295,000
4 Beds ⋅ 4 Baths
Step into your own private world, just 2.75 miles from Historic Downtown Chestertown. Tucked away at the rear of a mostly wooded 19+/- acre parcel, this exceptionally well-maintained property offers a rare combination of privacy, space, versatility, and convenience. At the heart of the property is a beautifully maintained brick residence overlooking a picturesque private pond, creating a peaceful setting that feels worlds away while remaining just minutes from town. The thoughtfully designed home is move-in ready and offers a comfortable, functional layout with quality finishes and inviting living spaces throughout. The first floor features a welcoming entry, upgraded gourmet kitchen with adjoining dining area, a spacious primary suite, and comfortable living areas that open to an expansive deck overlooking the pond. Whether enjoying a quiet morning or entertaining family and friends, the views and setting provide a stunning backdrop. Upstairs, you'll find three additional generously sized bedrooms and two full baths, providing plenty of room for family and guests. The finished walkout lower level adds another dimension to the home and offers tremendous flexibility as a game room, recreation space, home theater, gym, or private retreat, with direct access to the grounds and pond beyond. Adding even more value are two substantial, well-constructed outbuildings, each offering an incredible range of possibilities. Whether envisioned as a home office, woodworking or mechanical shop, hobby space, equipment storage, studio, or a combination of uses, these buildings make the property especially well-suited for someone seeking room to live, work, create, and store, all in one location. Surrounded by mature woods, expansive lawn, and the tranquil pond, the property offers a wonderful sense of seclusion without sacrificing proximity to the shops, restaurants, waterfront, and charm of Historic Chestertown. Properties offering this combination of acreage, privacy, substantial improvements, and proximity to town rarely become available. This is truly a one-of-a-kind Eastern Shore property that must be experienced in person to fully appreciate all it has to offer.

8276 Broad Neck Rd, Chestertown

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956
$200,000
4 Beds ⋅ 1 Baths
Investors, contractors & handy buyers—this is the fixer-upper opportunity you’ve been waiting for! This downtown Chestertown diamond in the rough offers strong ARV potential and an opportunity for a fix & flip, long-term rental, or short-term rental. Located just steps from Washington College and an easy walk to historic downtown shops, restaurants, and the waterfront. Currently occupied, but in need of a full renovation, this is a true value-add opportunity in a highly desirable location. Cash or renovation financing only—will not qualify for traditional financing. Priced to move!

223 Mount Vernon Ave, Chestertown

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

$568,900
4 Beds ⋅ 3 Baths
Welcome to 329 Union Church Road in Chestertown, located in Queen Anne’s County—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 stove, microwave, oven, and dishwasher in 2026, while new LVP flooring upstairs adds a fresh look. Major mechanical updates include the upstairs HVAC system replaced in 2023 and the downstairs HVAC system replaced in 2026. 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:

$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: (410) 708-0956
$50,000
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 Rd, Chestertown

Listing courtesy of The Parker Group. Contact: 3022176692
$89,000
Very private 5+ acre parcel with well and perc approved septic. Just minutes from Chestertown and very easy access to points north and south via route 301

27942 Old Morgnec Rd, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$229,000
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:

$275,000
3 Beds ⋅ 1 Baths
Welcome home! This beautifully maintained and updated property sits on a generous .45-acre lot in a lovely, quiet neighborhood, with a peaceful, wooded backdrop for added privacy. Renovated in 2017, this home offers numerous upgrades and thoughtful improvements, including hardwood floors, newer windows and doors, updated HVAC, and a newer roof. The kitchen features 42-inch cabinetry, granite countertops, and stainless steel appliances, while the custom ceramic-tile bath adds an extra touch of style. Enjoy the best of outdoor living from the fabulous screened-in porch and deck, perfect for relaxing, entertaining, or simply enjoying the tranquil surroundings. A large parking area provides plenty of space for family and guests, and the partial basement offers additional storage or flexible-use space. With so many major updates already completed, there is little left to do but move in, relax, and enjoy! A wonderful opportunity for anyone looking for a move-in-ready home with space, privacy, and a great neighborhood setting. Location is a bonus! Just minutes from historic downtown Chestertown, offering convenient access to local shopping, restaurants, movies, and a variety of waterfront activities. Enjoy the peaceful feel of a quiet neighborhood while being close to everything Chestertown has to offer. Schedule your tour today!

7482 Poplar Ave, Chestertown

Listing courtesy of Taylor Properties. Contact:

$315,000
3 Beds ⋅ 1 Baths
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.

24775 Langford Rd, Chestertown

Listing courtesy of RE/MAX Chesapeake. Contact:

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