Use our convenient guide for finding real estate for the entire Chestertown area.

Including houses, condos, duplexes, commercial real estate, land and other property opportunities.

2060 SqFt House In Byford Court
	2060 SqFt House In Byford Court Chestertown, MD $399,900 Homes for Sale Circa 1870 home with Chester River views situated on an acre-plus just blocks from downtown Chestertown and Washington College. Enjoy the private, park-like setting of this hilltop property located......

1568 SqFt House In Quaker Estates
	1568 SqFt House In Quaker Estates Chestertown, MD $149,900 Homes for Sale This property is Real Estate Owned, or REO. The property was foreclosed and repossessed by a lender when the owner failed to make payments. A bank is now the owner. Since banks are not in business......

1108 SqFt House In Chestertown
	1108 SqFt House In Chestertown Chestertown, MD $118,000 Homes for Sale The house needs work, but it sits on over 2 acres just outside of Fairlee. Classic knotty pine paneling, hardwood floors, two bedrooms and a bathroom with a walk in tub. Large detached garage has......

Waterfront House With Fireplace
	Waterfront House With Fireplace Chestertown, MD $835,000 Homes for Sale Interior photos will be posted next week. This waterfront condo has the wow factor! As you enter your eye is drawn to the Chester River. The living area is cozy with a gas fireplace. Fabulous......

2942 SqFt House In Chestertown
	2942 SqFt House In Chestertown Chestertown, MD $349,000 Homes for Sale One of the few properties in Chestertown on a full acre of land! The solid brick home has undergone an extensive renovation to include a gourmet kitchen, new HVAC and windows, and hardwood floors.......

Updated 4-Bedroom House In Tolchester Estates
	Updated 4-Bedroom House In Tolchester Estates Chestertown, MD $279,900 Homes for Sale Hot New Listing in Tolchester!!! Check out this 4 Bedroom 2.5 bath home with approx 1936 sq ft in Tolchester Estates. Recently Updated . This is a quality stick built home with an attached 1 car......

1485 SqFt House In Chestertown
	1485 SqFt House In Chestertown Chestertown, MD $210,000 Homes for Sale A peaceful setting for this classic brick cape cod just outside of Chestertown. Enjoy a picnic on the porch or a dip in the pool - there's plenty of room to play on this more than 1/2 acre lot. The......

1600 SqFt Condo In Chester River Landing
	1600 SqFt Condo In Chester River Landing Chestertown, MD $600,000 Condos for Sale This 1,600 sf ritzy waterfront suite simply exudes class. The unobstructed panoramic views of the Chester to the Bridge serve as living art bringing the River into the home. Well-appointed......

1008 SqFt House In Chester Harbor
	1008 SqFt House In Chester Harbor Chestertown, MD $138,000 Homes for Sale *INVESTOR ALERT!* Opportunity awaits in Chester Harbor - This is a cute 2 bedroom, 1 bath rancher with a full basement and is priced to sell. This could be turned into a 3 bedroom rancher. Home has......

1222 SqFt House In Chester Harbor
	1222 SqFt House In Chester Harbor Chestertown, MD $215,000 Homes for Sale REMARKABLE RENOVATED RANCH ! NEW HVAC, ROOF, WINDOWS, KITCHEN AND APPLIANCES, BATHS, PAINT AND FLOORING. WHITE KITCHEN WITH GRANITE COUNTERTOPS OPENS TO LARGE TABLE SPACE. WOOD-LIKE FLOORING......

Lot In Chestertown
	Lot In Chestertown Chestertown, MD $67,900 Land for Sale Bring your plans to build a home or modular home to one of the last lots available in this neighborhood. You will have plenty of space on over 1.3 acres of land. This is part of the Historic......

Lot In Chestertown
	Lot In Chestertown Chestertown, MD $69,500 Land for Sale One of the last lots available in this beautiful community. Flat, square, and perc approved lot ready for you to build your dream home. Lot over looks farm land and trees. Just off of 213 and only......

1500 SqFt House In Millbrook Of Chesapeake Landing
	1500 SqFt House In Millbrook Of Chesapeake Landing Chestertown, MD $214,900 Homes for Sale  NEW! BRAND NEW CONSTRUCTION 3 BR Cape Cod in quiet, waterfront community of Chesapeake Landing located just off Worton Creek in beautiful, historic Chestertown. A short drive to the restaurants and......

4446 SqFt House In Chestertown
	4446 SqFt House In Chestertown Chestertown, MD $955,000 Homes for Sale  NEW! Looking for a family compound? This wonderful setting captures the beauty and tranquility of the East fork of Langford Creek/Bay with the house nicely tucked away in a cove. The subject property is......

1591 SqFt House In Byford
	1591 SqFt House In Byford Chestertown, MD $246,900 Homes for Sale  NEW! Spacious rancher on quiet street in College Heights! Home features wood and ceramic flooring, wood burning fireplace and exposed beams. Split floor plan with master suite tucked away from the rest......

Updated Riverfront House
	Updated Riverfront House Chestertown, MD $242,000 Homes for Sale  NEW! Great downtown Chestertown location! Recently updated home is set in the Historic District and is just a walk away from Washington College, the University of Maryland Medical Center, the Chester......

Waterfront House With Fireplace
	Waterfront House With Fireplace Chestertown, MD $799,000 Homes for Sale  NEW! Enjoy panoramic views of the Chester River from this tastefully finished waterfront condo in Historic Chestertown. Decks on all three levels provide a great space to relax while enjoying the......

1756 SqFt House In Crestview
	1756 SqFt House In Crestview Chestertown, MD $249,500 Homes for Sale  NEW! Move in condition Cape Cod Home in Crestview. Near Washington Square Shopping Center, Churches, Washington College and a mile from downtown Historic Chestertown. Master bedroom on the first floor,......

1310 SqFt House In Chestertown
	1310 SqFt House In Chestertown Chestertown, MD $254,900 Homes for Sale  NEW! New construction to be built. 3 Bedrooms, 2 Full Baths. Modern open floor plan. Master suite with separate shower and jetted soaking tub. Hardwood floors. Cathedral ceilings. Granite counter tops.......

2596 SqFt House In Langford Bay Estates
	2596 SqFt House In Langford Bay Estates Chestertown, MD $950,000 Homes for Sale  NEW! Eastern Shore Waterfront Home with commanding views of Langford Bay and the Chester River is set in a quiet, rural community just 15 minutes from historic Chestertown. Enjoy boating and water......

2664 SqFt House In College Heights
	2664 SqFt House In College Heights Chestertown, MD $275,000 Homes for Sale  NEW! Spacious brick rancher in College Heights. Remodeled kitchen and gleaming hardwood floors. Finished lower level adds an additional bedroom and bath as well as a large family room. Ample room in the......

1297 SqFt House In Chestertown
	1297 SqFt House In Chestertown Chestertown, MD $425,000 Homes for Sale  NEW! 19.33 Acres of riverfront property on the Chester! Private and peaceful wooded setting ideal for the outdoors sportsman, hunters, boaters & outdoor enthusiasts! T-dock 100' +/- with 2 mooring......

Lot In Chestertown
	Lot In Chestertown Chestertown, MD $5,000 Land for Sale  NEW! ONLINE AUCTION!!Bidding Opens: Thursday, March 5, 2020 at 12:00 AMBidding Closes: Monday, March 9, 2020 at 12:00 PMA $2,500 deposit, or ten percent (10%) of the Purchase Price (whichever is......

Updated 3-Bedroom House In Buck Neck Of Chesapeake Landing
	Updated 3-Bedroom House In Buck Neck Of Chesapeake Landing Chestertown, MD $199,900 Homes for Sale  NEW! Updated three bedroom, 2 bath home in a semi private .41 acre lot. New flooring throughout, kitchen has been updated, deck, two storage shed, landscaped lot, one bedroom on the first floor and two......

2492 SqFt House In Chestertown
	2492 SqFt House In Chestertown Chestertown, MD $440,000 Homes for Sale This home features the charm of a historic home with the amenities and energy efficiency of a modern home. There are beautiful hardwood floors throughout. The first floor flows nicely from the......

Lot In Chestertown
	Lot In Chestertown Chestertown, MD $115,000 Land for Sale Large home site just 3 miles from Chestertown. Walk to the Chester River at Buckingham Wharf. Build your home - a great building with well is already there for your tools & toys!...

960 SqFt House In Chestertown
	960 SqFt House In Chestertown Chestertown, MD $125,000 Homes for Sale Adorable 3 bedroom, 1 bath ranch with original hardwood floors on a corner lot in the quaint town of Fairlee. Side porch with energy efficient windows. Public water & sewer..Year Built: 1979....

960 SqFt House In Chestertown
	960 SqFt House In Chestertown Chestertown, MD $249,900 Homes for Sale  NEW! YOU WILL LOVE THIS HOME! Just step inside and explore all the space for everyone! The original ranch home has been expanded to over 1,800+ sq ft with room for everyone in any stage of life! A......

Restored Private House
	Restored Private House Chestertown, MD $529,000 Homes for Sale  NEW! 204 NORTH WATER is the perfect marriage between early 20th century and 21st century. The era in which it was built featured many gracious details all retained and meticulously restored. One is......

1545 SqFt House In Millbrook Of Chesapeake Landing
	1545 SqFt House In Millbrook Of Chesapeake Landing Chestertown, MD $650,000 Homes for Sale  NEW! As soon as you enter, you will notice the expansive views of Worton Creek. Beautifully situated on an elevated location. Newly constructed and renovated in 2013 with highest quality finishes, such......

1588 SqFt House In Country Club Estates
	1588 SqFt House In Country Club Estates Chestertown, MD $425,000 Homes for Sale  NEW! Easy one floor living in Country Club Estates. Lovely views of the golf course with the Chester River in the distance from the family room and screened-in porch. Attached one car garage. New......

Lot In Chestertown
	Lot In Chestertown Chestertown, MD $100,000 Land for Sale  NEW! Prime building lot in Historic District of Chestertown.Building plans are subject to Historic Commission review. Build a new house here in this Colonial town; a short distance to town center....

1790 SqFt House In The Flyway
	1790 SqFt House In The Flyway Chestertown, MD $349,000 Homes for Sale  NEW! Custom built quality rancher by Stansbury & Sons on a 1+\- acre corner lot in the Flyways. House will feature tiled bathroom, granite countertops in kitchen and bath, LVT flooring, stainless......

2350 SqFt House In College Heights
	2350 SqFt House In College Heights Chestertown, MD $179,000 Homes for Sale  NEW! Nice brick rancher, in town location, close to College and shopping, nice starter home for anyone, easy to show, lockbox, call agent for combo..Year Built: 1967....

Lot In Chestertown
	Lot In Chestertown Chestertown, MD $345,000 Land for Sale  NEW! EXCEPTIONAL DEVELOPMENT OPPORTUNITY! Completely set up with all infrastructure needed to start building: water, sewer, electric... over $80,000 worth of work has already been completed. Build to......

1568 SqFt House In Quaker Estates
	1568 SqFt House In Quaker Estates Chestertown, MD $149,900 Homes for Sale One level home with some handicapped accessibility features including front ramp, wide doorways in master bedroom and bath with room for wheelchair, although not specifically a roll-in or lipless......

Lot In Chestertown
	Lot In Chestertown Chestertown, MD $14,500 Land for Sale Now available in Chesapeake Landing, this peaceful wooded lot is the perfect place to build your new permanent or vacation home. The property is level and situated on a quiet street with several......

Upgraded 2-Bedroom House In Chestertown
	Upgraded 2-Bedroom House In Chestertown Chestertown, MD $124,900 Homes for Sale Get the best of both worlds with this adorable renovated 2 Bedroom 1 bath home in Tolchester Estates. Tastefully upgraded with pergo wood flooring, upgraded tile bathroom, cozy family room and......

1720 SqFt House In College Heights
	1720 SqFt House In College Heights Chestertown, MD $224,000 Homes for Sale Beautiful and well maintained home in Chestertown's College Heights, close to the college and all that Chestertown has to offer. Even provides quick access to route 213 for commuters. Possibilities......

1398 SqFt House In Chester Harbor
	1398 SqFt House In Chester Harbor Chestertown, MD $110,500 Homes for Sale Nicely landscaped & located on a corner lot in Chester Harbor, this home is ready to be loved once again! Hardwood floors, central A/C and an addition which can serve as office space, play room ,......