Chestertown Homes with Public Parking features

Nestled along the banks of the Chester River in Kent County, Maryland, Chestertown is a charming town that beautifully blends history with modern living. With its picturesque streets lined with 18th-century architecture, vibrant arts scene, and a rich maritime heritage, Chestertown offers a unique lifestyle that appeals to both families and retirees alike. The town’s commitment to preserving its historical character is evident in its well-maintained buildings and inviting public spaces, making it a delightful place to explore on foot.

One of the many advantages of living in Chestertown is the accessibility it offers. Homes in this quaint town often come with the added benefit of public parking, ensuring that residents and their guests can easily navigate the area. Whether you’re heading out for a day of shopping at local boutiques, dining at one of the many acclaimed restaurants, or enjoying a leisurely stroll along the riverfront, you’ll find that convenience is at your doorstep.

Chestertown is also home to a thriving community, with events such as the Chestertown Tea Party Festival and the annual Arts & Entertainment District activities, fostering a strong sense of belonging among its residents. The town’s proximity to both the Chesapeake Bay and major cities like Baltimore and Washington, D.C., further enhances its appeal, offering a perfect balance of small-town charm and urban accessibility.

If you’re seeking a home in a picturesque setting with the convenience of public parking, Chestertown is the ideal place to call home. Experience the warmth and community spirit of this delightful town, where every day feels like a step back in time.

Newest Chestertown Homes with Public Parking features

$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:

$1,300,000

Mixed-use commercial property in charming historic Chestertown. 327 Cannon was newly constructed in 2006, yet is perfectly situated in bustling historic district. Offering historic charm without the extra maintenance. The building contains two large units with many possibilities. The first level is outfitted with a commercial kitchen and large dining space overlooking Cannon St. Over 1300 sq ft of professional kitchen space, an office, and dining area. The space has many possibilities for a restaurant or other commercial business in the future. Currently, this unit is leased to Occasions Catering. The upstairs apartment is inviting and spacious, offering two bedrooms each with an ensuite full bathroom. The living space is open and airy, with ample natural light, vaulted ceilings, hardwood floors and a gas fireplace. The large loft could be an office, den, or creative studio space. The walk-in attic provides additional storage. An ideal investment in historic Chestertown.

327 Cannon St, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

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