Chestertown, MD 1-Story Homes for Sale

Welcome to Tolchester Estates, a charming community near the Chesapeake Bay. This 3-bedroom, 2-bath rancher features updated HVAC, gas cooking, an upgraded propane hot water heater, and a recently replaced roof system in March 2026. The property is served by public sewer for added ease and reliability. Step outside to a large rear deck, perfect for entertaining or relaxing while enjoying the

Andrew Meikle Doug Ashley Realtors, LLC

Charming 3-bedroom, 2-bath rancher in the desirable Chester Harbor community. Situated on a spacious 0.76-acre lot, this home offers comfortable one-level living with a bright layout, private primary suite, and plenty of outdoor space to enjoy. Detached two-car garage provides ample storage and parking. Conveniently located just minutes from historic downtown Chestertown, marinas, shops, and

Amy Larrauri Chesapeake Real Estate Associates, 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

Practically brand new and just 2 years young, this beautifully maintained home is perfectly situated in a desirable water-oriented community—offering the best of Eastern Shore living! Located in the Queen Anne’s County school district and just minutes from downtown Chestertown, you’ll love the convenience paired with the peaceful setting.Enjoy easy access to the Chester River—you can drive

Erin Anderson Chesapeake Real Estate Associates, LLC

Previous Buyer failed to perform - Your opportunity has come around again - Don't miss out this time. FULL RENOVATION PROJECT - Prime Chestertown Location Priced for Immediate Equity Creation. This 3-bedroom, 1-bath single-family home at $115,000 represents a clear value-add opportunity in one of Chestertown’s most “walkable” corridors. With estimated renovation investment of $60K-$80K+,

David Moore Real Broker, LLC

Charming and inviting! Welcome to 139 Prospect St., a delightful 3-bedroom, 1-bath rancher offering approximately 1,200 square feet of comfortable living space. This well-maintained home features thoughtful updates to the kitchen and bath, blending modern touches with classic appeal. Step onto the inviting front porch and into a spacious living room that flows seamlessly into the eat-in

Barbara McCaffrey Redfin Corp

Discover this beautifully renovated ranch-style home (2023), offering 1,152 square feet of thoughtfully updated living space. The open floor plan creates a seamless flow between the living, dining, and kitchen areas — ideal for both everyday living and entertaining.The spacious kitchen features a central island, stainless steel appliances, and ample cabinetry, making it as functional as it is

Heather Dolan Chesapeake Real Estate Associates, LLC

Welcome to 208 Central Drive, located in the desirable Chester Harbor community just minutes from historic Chestertown. This charming 3-bedroom, 1-bath home offers a wonderful blend of comfort, convenience, and value. It sits on 3 lots totaling approximately 0.55 acres, surrounded by mature trees and landscaping. Step inside to a bright, move-in-ready interior featuring brand-new wood flooring

Jennifer Pogoda Redfin Corp

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

If you're looking for that secluded spot, with land, room to grow and stretch, and don't mind a project, look no further! Dream location on a private road, backing to farmland, and yet just a few miles outside of downtown Chestertown! The house is midway through a full renovation. Walls are in place, electric run, plumbing roughed-in, new siding and a brand New HVAC! All the hard stuff is done!

Michele Palmer Doug Ashley Realtors, LLC

Currently used as a church and in the Downtown Residential R-5 zoning. This sale also includes 5 additional residential lots.

John Ford RE/MAX Associates-Hockessin

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

New price, same stunning home!!! Stop scrolling — this beauty is ready for new owners to move in and make lasting memories! Welcome to this exceptional custom-built home offering nearly 3,000 sq. ft. of beautifully designed living space where luxury, comfort, and style come together effortlessly. Featuring 4 bedrooms and 2.5 baths, this home is perfectly situated on a level 1 acre lot directly

Karen Clark Clark & Co Realty, LLC