Downtown Chestertown Real Estate

Downtown Chestertown Real Estate

Welcome to Downtown Chestertown, a picturesque gem nestled in the heart of Kent County, Maryland. This charming riverside community is rich in history and brimming with character, making it a perfect destination for those seeking a vibrant and welcoming atmosphere.

Downtown Chestertown offers a delightful blend of historic architecture and modern conveniences. Stroll along the tree-lined streets and admire the beautifully preserved 18th-century buildings that house an array of boutique shops, art galleries, and delightful eateries. The town’s waterfront location along the Chester River provides a serene backdrop for leisurely walks and outdoor activities, inviting residents and visitors alike to soak in the natural beauty.

As a hub of cultural activity, Downtown Chestertown hosts numerous events throughout the year, including the renowned Chestertown Tea Party Festival and the Chestertown Jazz Festival. These community gatherings foster a strong sense of belonging and provide opportunities to connect with neighbors and make lasting memories.

For those who appreciate the arts, the area is home to the Garfield Center for the Arts, where you can enjoy live performances and exhibitions that showcase local talent. The nearby Washington College adds to the lively atmosphere, bringing in students and academics who contribute to the town's vibrant energy.

Whether you’re looking to settle down in a historic home, enjoy waterfront living, or simply explore the charm of a small town, Downtown Chestertown offers a unique lifestyle that beautifully balances history, culture, and community. Come discover the enchanting allure of this remarkable Maryland town!

Newest Listings in Downtown Chestertown

$2,300,000
A rare turnkey, profitable, investment property in downtown Chestertown. Renovated to the studs in 2022, 200-202-204 High Street has 5 apartments and 3 storefronts and since renovations has had no vacancies, with solid leases in place. During the renovations every major system in the building was replaced, including new electric service, meters and new wiring throughout, all new plumbing using PEX, new water and septic service lines to the building, new energy efficient water heaters and appliances, rebuilt foundation, new Jeldwen Auralast windows, insulation and air sealing, new roof on rear portions of building (front 50-year cedar roof was replaced in early 2000s), new rear egress, a monitored fire alarm system and much more. Two of the storefronts are rented to a local arts non-profit and a yoga/pilates studio recently moved into the third commercial space. The 5 apartments consist of two 2-bedroom units and three 1-bedroom apartments. The steady income stream from the units is complemented by a generous property tax credit through 2032 (buyer to verify transferability). The property also has a Limited Lead-Free certificate, which requires only an exterior visual inspection every two years, and exempts the owner from MDE registration requirements. Complete income and expense information available after signing a confidentiality agreement. Limited photos posted for tenants' privacy. Contact for a private tour today. Please do not disrupt the businesses, they are tenants and the businesses are not part of the sale.

200 High St, Chestertown

Listing courtesy of Taylor Properties. Contact:

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