Homes for Sale in Chestertown, MD with 2-Bedrooms

Great opportunity to own a small cottage in Chestertown. Right next to, and with direct access to the walking trails, this end of road 2 bedroom home comes with an extra lot, currently used for parking, but could also possibly be built on. Buyer to verify with county Expected on Market May 8th. More Photos to come!

Michele Palmer Doug Ashley Realtors, LLC

Investor Special – Charming Colonial in Prime Chestertown Location! Welcome to 234 N College Ave, an adorable colonial full of character and potential, nestled in the heart of historic Chestertown. This short sale opportunity is a rare find for savvy investors or buyers ready to bring their vision to life. With classic colonial charm, this property offers the perfect canvas for renovation or

Anastasia Zivkovic Palmer Cummings & Co. Realtors

This 2-bedroom, 1.5-bath bungalow offers a bright, open layout with updates throughout. The home features a sun-filled front room, an eat-in kitchen with new butcher block seating and updated appliances, and a fully renovated bathroom with new tile and a modern vanity. A rear utility room with laundry provides extra storage and access to a small backyard—perfect for gardening or relaxing

Hayley Norris Select Land & Homes, LLC

Welcome to 24295 Langford Road in Chestertown, Maryland—a rare opportunity to own a peaceful slice of the countryside on 2 beautiful acres surrounded by farmland. Just minutes from downtown Chestertown, this property offers the perfect balance of privacy and convenience. If you’ve been searching for a home away from the hustle and bustle, this is the one. The classic brick rancher features over

Amy Larrauri Chesapeake Real Estate Associates, LLC

MOTIVATED SELLER - BRING OFFERS. Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable waterfront community of Chester River Landing. Just a short walk or bike ride into downtown Chestertown, this elegant, turn-key home offers maintenance-free living, great amenities, and easy water access to the Chester River. The welcoming foyer seamlessly flows into the

Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

MOVE IN READY!! Adorable, Affordable, move in ready & two blocks from the Chesapeake Bay! Appliances, roof, waterproof vinyl plank flooring, stove, dishwasher recently upgraded, beautifully tiled bathroom flooring. Freshly painted, Bright and inviting updated kitchen, Spacious Dining/family rm with vaulted ceilings, ceiling fan. Enjoy fishing or relaxing at the private community beach or head

Terry Catalano RE/MAX Leading Edge

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects

Liddy Campbell TTR Sotheby's International Realty