Historic luxury townhouse in the heart of downtown Chestertown

Historic Luxury Townhouse on High Street – Heart of Downtown Chestertown

Welcome to 125 High Street—an exquisitely renovated, sun-filled brick townhouse nestled in the heart of historic downtown Chestertown, Maryland. Steps from the river, surrounded by charming restaurants, cafes, galleries, and boutiques, this home offers a one-of-a-kind blend of modern luxury and timeless Eastern Shore character. Whether you’re here for a romantic getaway, family vacation, or a relaxing solo retreat, this property promises comfort, style, and walkable convenience like no other.

The Space: Where History Meets High-End Living

Originally built in the 1800s, this beautifully restored home retains its historic charm with exposed original brickwork throughout, thoughtfully paired with state-of-the-art upgrades to provide a truly special stay.

-Bedrooms & Comfort: Each bedroom is outfitted with luxury bedding and ultra-comfortable mattresses, curated for restful sleep. Whether you’re traveling with family or friends, you’ll enjoy hotel-quality linens and serene design in each sleeping space.
• Marble Spa Bathroom: Step into elegance in the stunningly upgraded bathroom, featuring high-end marble finishes, a spa-like walk-in shower, and sleek modern fixtures. It’s the perfect way to unwind after a day exploring town or kayaking along the Chester River.

-Chef’s Kitchen: Cook up a storm (or reheat your gourmet leftovers from one of the nearby restaurants) in the chef’s kitchen, complete with top-of-the-line stainless steel appliances, induction cook top, granite countertops, and all the cookware and utensils you need. High-quality appliances ensure every meal prep feels easy and indulgent.

-Living Room: Relax in the stylish and cozy living area, which features a blend of antique touches and modern design. Enjoy streaming your favorite shows, reading a book by the window, or planning your next adventure in town.

-Historic Details: Original exposed brick walls run throughout the house, adding warmth and texture to every room. The hardwood floors and preserved architectural details offer a nod to the past while blending seamlessly with the updated, designer interiors.

Unbeatable Location: Downtown Chestertown at Your Doorstep

You quite literally cannot stay in a better location in Chestertown. Step out the front door and you’re just a block from the water, where the Chester River glistens in the sunlight. Take a morning stroll to the town marina and watch the boats, or sip coffee on a bench by the riverfront.

-Dining & Cafes: Some of the Eastern Shore’s best restaurants, bakeries, and wine bars are just steps away. From fresh local seafood to warm croissants and artisan espresso, you’ll find culinary gems at every turn.

-Shops & Galleries: Explore local boutiques, art galleries, and bookstores—many of which are housed in historic buildings. The town’s walkable charm makes it easy to discover something new every day.

-Marina & Waterfront: The Chestertown Marina is just a block away. Enjoy breathtaking sunsets, rent a kayak, or simply watch the tide roll in. The proximity to the water adds a serene, coastal energy to your stay.

-Cultural Events & Farmers Market: Chestertown is known for its vibrant calendar of events—from the weekly Saturday Farmer’s Market to First Fridays, jazz festivals, and tall ship visits. And you’re right in the middle of it all.

Why You’ll Love Staying Here
• Location, location, location – it doesn’t get better.
• A rare combination of historic charm and modern luxury.
• Comfort-forward design: plush beds, quiet nights, and natural light.
• Easy parking and quick access to nature, water, and culture.

Perfect For:
• Weekend escapes from D.C., Baltimore, or Philadelphia
• Wedding weekends, family gatherings, or small group getaways
• Writers, artists, and creatives seeking inspiration in a beautiful place
• Professionals looking for a peaceful and luxurious remote work setting