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

7570 Muirfield Dr, Chestertown
$895,000
4 Beds ⋅ 3 Baths
Elegant Golf Course Living on Maryland’s Eastern shore. Experience the understated elegance of Eastern Shore living in this beautifully crafted, custom-built residence overlooking the 10th tee and fairway of the Chester River Yacht & Country Club. Set on 1.45 acres of thoughtfully landscaped grounds in the desirable Prestwick community, this exceptional property offers privacy, timeless craftsmanship, and the ease of single-level living. Custom-built by Alton Darling, the approximately 2,500-square-foot home features an inviting, open floor plan with hardwood floors, elegant crown molding, and generously proportioned rooms designed for comfortable everyday living and effortless entertaining. The spacious primary suite provides a peaceful retreat with two walk-in closets and a beautifully appointed bath featuring dual vanities with quartz countertops, an oversized walk-in shower. Two additional bedrooms, thoughtfully situated in a separate wing, offer privacy for family and guests. A formal dining room, breakfast room, and versatile office or 4th bedroom space provide flexibility for today’s lifestyles. The kitchen features granite countertops, updated appliances, and convenient access to the home’s gathering spaces. Freshly painted interiors and numerous system improvements further enhance the property’s appeal. Beyond the interiors, the home’s setting truly distinguishes it. A screened porch overlooks mature landscaping and the picturesque golf course, creating an inviting place to enjoy morning coffee, entertain friends, or simply appreciate the peaceful surroundings. A new hot tub and outdoor gathering area offer additional opportunities for relaxation. An attached two-car garage, generous storage, and extensive mechanical and safety improvements complete this thoughtfully maintained residence. Appliances 2024, washer/dryer 2025 More upgrades in the document section.

7570 Muirfield Dr, Chestertown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

818 High St, Chestertown
$3,300,000
Prime Commercial Opportunity in Chestertown!! The Brian E. Bainbridge Health Building is a prominent, three-story commercial property offers 23,000 square feet of versatile space perfectly situated on High Street. Known locally as the home of the premier Aqua Fit Health Center, this highly functional multi-floor building features an excellent mix of large-scale operational facilities and multiple private office suites. The ground level boasts extensive infrastructure, including a custom-built aquatic center with a heated saltwater pool, expansive weight/cardio rooms, and physical therapy areas. The upper floors offer a flexible layout of professional office spaces, ideal for medical practices, wellness professionals, or traditional corporate tenants. Complete with an elevator, high-visibility street presence, and a dedicated customer/tenant parking lot, this unique asset is a turnkey opportunity for an investor or an owner-user looking to establish a major presence in Kent County.

818 High St, Chestertown

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

111 Kent St S, Chestertown
$450,000
2 Beds ⋅ 3 Baths
Nestled in the heart of the Chestertown Historic District, this exquisite residence offers a harmonious blend of traditional charm and modern luxury. Built in 2008, this detached home stands as a testament to meticulous craftsmanship and thoughtful design, ensuring an exceptional living experience. Step inside to discover an open floor plan that invites natural light to dance across the spacious interiors. The heart of the home features a cozy gas fireplace, perfect for creating warm, inviting gatherings. The well-appointed kitchen is a culinary enthusiast's dream, equipped with high-end appliances including a built-in range, microwave, and dishwasher, all seamlessly integrated for both functionality and style. The stacked washer and dryer add convenience, making laundry days a breeze. With two generously sized bedrooms and two and a half elegantly designed bathrooms, this home provides ample space for relaxation and rejuvenation. Each bathroom boasts modern fixtures and finishes, ensuring a spa-like experience at home. The attic space while unfinished, has the ability to be finished for additional living space, if desired. The exterior of the property is equally captivating, featuring beautifully maintained sidewalks and exterior lighting that enhances the home's curb appeal. Enjoy serene evenings on the private patio, where you can unwind and soak in the tranquil surroundings. The lot, spanning 1,330 square feet, offers a manageable outdoor space that complements the busy lifestyle of today's homeowner. Located in a vibrant community, this residence is not just a home; it's a lifestyle. The Chestertown Historic District is renowned for its rich history and picturesque streets, providing a unique backdrop for your daily life. Enjoy leisurely strolls through charming neighborhoods, explore local boutiques, or indulge in the culinary delights of nearby restaurants. This property is more than just a dwelling; it's an opportunity to embrace a luxurious lifestyle in a historic setting. With its impeccable condition and high-end features, this home is ready to welcome you into a world of comfort and elegance. Don't miss your chance to own a piece of this exclusive community-schedule your private tour today and experience the allure of this remarkable residence for yourself.

111 Kent St S, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

403 Calvert St, Chestertown
$135,000
3 Beds ⋅ 2 Baths
INVESTOR OPPORTUNITY! Come see this 3-bedroom, 1.5-bath townhome offering great potential to add to your portfolio! Recent improvements include drywall replacement, newly renovated bathrooms, light fixtures, fresh paint, trim, new wall to wall carpet, and LVP flooring. Buyers should independently verify achievable rents, however it should be noted recently rented townhomes in the area have ranged from $1,800-$2,000. Conveniently located near Washington College, Chestertown's shops, restaurants, and local amenities. Independent appraisal on file showing strong ARV potential. Property is being sold strictly as-is.

403 Calvert St, Chestertown

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

201 Garland Way, Chestertown
$375,000
4 Beds ⋅ 3 Baths
Discover a prime investment opportunity in the sought-after Coventry Farms subdivision! This charming Colonial-style home, built in 2010, boasts 2,886 square feet of potential, featuring 4 spacious bedrooms and 2.5 bathrooms. With an good property condition, this residence is a blank canvas ready for your personal touch or strategic upgrades, ensuring a strong return on investment. The property includes a walkout basement with outside entrance, offering additional space that can be transformed into a rental unit or recreational area, significantly increasing its value. The cozy gas fireplace adds warmth and charm, making it an inviting space for future tenants or buyers. Situated on a generous 0.27-acre corner lot, this home provides ample outdoor space for entertaining or future enhancements, such as landscaping or outdoor living areas. The attached garage and driveway parking for four vehicles enhance convenience, appealing to a broad range of potential renters or buyers. With a low association fee covering common area maintenance, you can enjoy hassle-free ownership while benefiting from the community's amenities. The location offers easy access to local attractions, ensuring high demand for rental opportunities. Invest in a property that not only promises comfort and style but also the potential for significant financial returns. This home is a great way to buy low and make it your own. Certainly is not beyond homeowner fixes. Don't miss out on this exceptional opportunity to grow your real estate portfolio in a thriving neighborhood!

201 Garland Way, Chestertown

Listing courtesy of ERA Martin Associates. Contact:

108 N Water St, Chestertown
$1,125,000
5 Beds ⋅ 4 Baths
This 1925 classic colonial, three story residence, with both front and back gardens, is uniquely situated in the center of the favored 100 block of North Water Street, in historic Chestertown. The formal main entry, with dual brick steps approaches a generous landing, faces away from the street. At first a curiosity until you learn that a prominent family discovered the architectural plans for their "dream house" would not fit horizontally to face the prized road. During its' 100-plus years of life, the front porch (or was it the side?) was converted to a remarkable library, with requisite bookcases, and enjoys light from three sides. The formal parlor, with wood-burning fireplace and reclaimed 19th century moldings and mantle, is left of the straight-through center hall with classic black and white porcelain tiles. The intimate, yet well-proportioned dining room enhances the exceptional flow of the first-floor public rooms. A discreetly positioned powder room and butler's pantry with window and original cabinetry is conveniently placed before entering the large and sunny kitchen with premium custom cabinetry, appliances and finishes from a 2012 renovation. Two distinct patios, one screened and accessed from the dining room and the other from kitchen, overlook the large, rear garden with mature trees and landscaping. The center stairs, with a palladium window bathing light onto the steps, takes you to the first of two oversized landings that have served many lifestyle-uses over the years. The water view primary suite was renovated in 2022 by locally acclaimed Taylor Loughry LLC and boasts a timeless, luxurious aesthetic with custom built closets and Waterwork bath fixtures. Two additional bedrooms and refreshed bath with Restoration Hardware finishes, occupy the second floor. The third floor, with its own generous landing gives access to an ensuite bedroom with walk-in windowed closet (perfect for a future cedar lined closet) and a substantial sized fifth bedroom or multi-purpose space facing the Chester River and exquisite neighboring architecture. Rear yard might accommodate a pool.

108 N Water St, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

317 Rolling Rd, Chestertown
$229,900
3 Beds ⋅ 2 Baths
Located in the College Heights neighborhood of Chestertown, this 3-bedroom, 2-bath home is situated on a .34± acre lot and is full of potential! Enjoy the convenience of stepping right out your back door to the dog park, all while being within walking distance of downtown Chestertown’s shops, restaurants, and waterfront. With a little TLC and your personal touch, this property is a great opportunity to make a home your own in a fantastic location!

317 Rolling Rd, Chestertown

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

7545 Quaker Neck Rd, Chestertown
$175,000
3 Beds ⋅ 1 Baths
Needs work. Sold as is

7545 Quaker Neck Rd, Chestertown

Listing courtesy of Thurston Wyatt Real Estate, LLC. Contact:

501 High St, Chestertown
$349,900
Investor Alert in Historic Downtown Chestertown! Fully Occupied Triplex. Units offer hardwood floors, mini splits to units 1 and 2, a new bathroom in unit 3 and kitchen upgrades n unit 2 including new counter tops and flooring

501 High St, Chestertown

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

8668 Elm Rd, Chestertown
$349,900
4 Beds ⋅ 2 Baths
Brand new construction in water oriented Tolchester Estates located on the Chesapeake Bay. 4 Bedroom, 2 bath Cape Cod on a wooded lot and quiet neighborhood. Community offer private beach and boat ramp access. Rear private deck.

8668 Elm Rd, Chestertown

Listing courtesy of Kevin Dey Realty. Contact:

7655 James Ln, Chestertown
$519,900
3 Beds ⋅ 3 Baths
Enjoy a peaceful country setting at 7655 James Lane. Situated on a two-acre lot along a quiet cul-de-sac street, this well-maintained ranch home offers approximately 2,475 square feet of living space, three bedrooms, and two-and-a-half bathrooms, complemented by mature landscaping and a scenic farmland backdrop. A cozy front porch welcomes you inside to a spacious layout featuring separate living and family rooms, a formal dining area, and an eat-in country-style kitchen with rich wood cabinetry and stainless steel appliances. Flowing through the main living area are hardwood floors leading to a large and bright sunroom. The sunroom, complete with skylights offers an inviting space to relax and enjoy the surroundings, with a dedicated mini-split providing heating and cooling for year-round comfort. Just off the sunroom, a deck extends the living space outdoors, while a fenced portion of the yard offers additional flexibility for outdoor enjoyment. The attached two-car garage provides convenient parking and storage. A standout feature of this property is the large pole building, measuring approximately 40' by 22', with a heated shop and two tall doors—one at the front and another on the side—for RV or boat storage. This versatile building offers valuable space for projects, equipment, and recreational vehicles, along with a mezzanine storage loft above the shop. The rear of the building provides additional unfinished storage space with separate access. Located approximately 10 minutes from Chestertown, Rock Hall, and the public boat launch at Broadneck Landing, this property pairs a peaceful rural setting with convenient access to nearby shops, dining, and boating. Schedule your tour today!

7655 James Ln, Chestertown

Listing courtesy of RE/MAX Advantage Realty. Contact:

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:

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