Downtown Chestertown Real Estate

Downtown Chestertown Real Estate

Welcome to Downtown Chestertown, a charming and vibrant subdivision nestled in the heart of Kent County, Maryland. This picturesque area is steeped in history, showcasing a delightful blend of colonial architecture and modern conveniences. As you stroll along the tree-lined streets, you’ll be captivated by the beautiful waterfront views of the Chester River, which provide a serene backdrop to this quaint community.

Downtown Chestertown is not only a feast for the eyes but also a hub for culture and creativity. The area boasts an array of local shops, art galleries, and eateries that highlight the town's rich heritage and culinary delights. From cozy coffee shops to fine dining establishments, there’s something to satisfy every palate. The local farmers' market, held weekly, is a must-visit for fresh produce and artisanal goods, fostering a strong sense of community among residents and visitors alike.

For those who appreciate the outdoors, Downtown Chestertown offers ample opportunities for exploration. Take a leisurely walk along the riverfront or enjoy a picnic in one of the nearby parks. The town is also home to several historic landmarks, including the beautiful Chestertown Historic District, where you can immerse yourself in the area’s storied past.

Whether you’re looking to settle down in a charming home or seeking an investment opportunity, Downtown Chestertown is a hidden gem that combines small-town charm with a lively atmosphere. Come and experience the warmth and community spirit that makes this subdivision a wonderful place to call home!

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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