217 Philosophers Terrace Chestertown, MD

$325,000

Price

3

Beds

2

Baths

1,404

Sq. Ft.

.25

Acres

Charming and full of potential, this 3-bedroom, 1.5-bath Cape Cod home offers a prime in-town Chestertown location with thoughtful updates already in place!

New roof (December 2025), heat pump (2022), and new carpet upstairs provide peace of mind, while classic features like hardwood floors, abundant natural light, and a wood-burning fireplace add warmth and character. The flexible layout includes a main-level bedroom and full bath, a formal dining room, and a bright living room. Upstairs, two additional bedrooms and a half bath, easily converted back to a full, offer room to grow. A bonus room off the main level is perfect for a home office, mudroom expansion, or hobby space. The sunroom connects seamlessly to a private backyard. A sizable driveway and detached garage offer ample off-street parking. Architectural plans for a full renovation and addition are available with an acceptable offer. This is an incredible opportunity to customize and add value in a sought-after location. Just a short stroll to Downtown Chestertown, Washington College, and the Chester River, this home offers both convenience and long-term potential.

Floor Plans

Courtney Chipouras, Eastern Shore Realtor

I’m Courtney, and I’m proud to live and work on Maryland’s Eastern Shore.

I’ve spent my whole life in this region, and I genuinely enjoy helping people find a place that feels like home. Whether you’re drawn to quiet waterfront living, small-town charm, or a home that gives you room to grow, I’m here to guide you through the process with honesty, care, and local insight.

If you’re exploring life on the Shore and want something who truly understands the area, I’d be happy to help you get started.

Recent Listings

View More Listings

217 Philosophers Terrace Chestertown, MD

217 Philosophers Terrace Chestertown, MD

3 BD | 2 BA | 1,404 SQFT | .25 ACRES
21235 Rock Hall Ave Rock Hall, MD

21235 Rock Hall Ave Rock Hall, MD

3 BD | 2 BA | 1,364 SQFT | .17 ACRES
21103 Striper Run Rock Hall, MD

21103 Striper Run Rock Hall, MD

3 BD | 2.5 BA | 1,628 SQFT
5135 Crosby Road Rock Hall, Maryland

5135 Crosby Road Rock Hall, Maryland

6 BD | 4 1/2 BA | 4,214 SQFT | 212.88 ACRES
No results found.

Picture Yourself Here?

Let's schedule a private showing to experience this home in person and discover what truly makes it exceptional.