Consider our listings of homes for sale in Chestertown and nearby areas.
You may filter our residential listings by specifying price ranges of houses, number of bedrooms and baths, as well as by the total square footage. Let your search for new homes for sale for Chestertown begin here!
2060 SqFt House In Byford Court |
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2060 SqFt House In Byford CourtChestertown, MD$399,900
Homes for Sale NEW!
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 |
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1568 SqFt House In Quaker EstatesChestertown, MD$149,900
Homes for Sale NEW!
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 |
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1108 SqFt House In ChestertownChestertown, MD$118,000
Homes for Sale NEW!
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 |
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Waterfront House With FireplaceChestertown, MD$835,000
Homes for Sale NEW!
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 |
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2942 SqFt House In ChestertownChestertown, MD$349,000
Homes for Sale NEW!
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 |
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Updated 4-Bedroom House In Tolchester EstatesChestertown, MD$279,900
Homes for Sale NEW!
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 |
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1485 SqFt House In ChestertownChestertown, MD$210,000
Homes for Sale NEW!
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...... | |
1008 SqFt House In Chester Harbor |
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1008 SqFt House In Chester HarborChestertown, MD$138,000
Homes for Sale NEW!
*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 |
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1222 SqFt House In Chester HarborChestertown, MD$215,000
Homes for Sale NEW!
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...... | |
1500 SqFt House In Millbrook Of Chesapeake Landing |
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1500 SqFt House In Millbrook Of Chesapeake LandingChestertown, MD$214,900
Homes for Sale
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 |
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4446 SqFt House In ChestertownChestertown, MD$955,000
Homes for Sale
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 |
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1591 SqFt House In ByfordChestertown, MD$246,900
Homes for Sale
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 |
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Updated Riverfront HouseChestertown, MD$242,000
Homes for Sale
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 |
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Waterfront House With FireplaceChestertown, MD$799,000
Homes for Sale
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 |
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1756 SqFt House In CrestviewChestertown, MD$249,500
Homes for Sale
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 |
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1310 SqFt House In ChestertownChestertown, MD$254,900
Homes for Sale
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 |
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2596 SqFt House In Langford Bay EstatesChestertown, MD$950,000
Homes for Sale
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 |
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2664 SqFt House In College HeightsChestertown, MD$275,000
Homes for Sale
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 |
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1297 SqFt House In ChestertownChestertown, MD$425,000
Homes for Sale
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...... | |
Updated 3-Bedroom House In Buck Neck Of Chesapeake Landing |
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Updated 3-Bedroom House In Buck Neck Of Chesapeake LandingChestertown, MD$199,900
Homes for Sale
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 |
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2492 SqFt House In ChestertownChestertown, 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...... | |
960 SqFt House In Chestertown |
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960 SqFt House In ChestertownChestertown, 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 |
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960 SqFt House In ChestertownChestertown, 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 |
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Restored Private HouseChestertown, 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 |
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1545 SqFt House In Millbrook Of Chesapeake LandingChestertown, 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 |
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1588 SqFt House In Country Club EstatesChestertown, 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...... | |
1790 SqFt House In The Flyway |
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1790 SqFt House In The FlywayChestertown, 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 |
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2350 SqFt House In College HeightsChestertown, 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.... | |
1568 SqFt House In Quaker Estates |
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1568 SqFt House In Quaker EstatesChestertown, 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...... | |
Upgraded 2-Bedroom House In Chestertown |
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Upgraded 2-Bedroom House In ChestertownChestertown, 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 |
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1720 SqFt House In College HeightsChestertown, 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 |
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1398 SqFt House In Chester HarborChestertown, 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 ,...... | |
1592 SqFt House In Chestertown |
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1592 SqFt House In ChestertownChestertown, MD$219,900
Homes for Sale
Don't miss this 3BR, 2BA charming home with open country kitchen, large living room, den and spacious master bedroom with master bathroom and walk-in closet. Nicely situated with front and backyard...... |
1487 SqFt House In Chestertown |
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1487 SqFt House In ChestertownChestertown, MD$297,000
Homes for Sale
Welcome Home to 22428 Great Oak Landing. Pull up to your very welcoming driveway complete with mature landscaping, room for boat, RV, and/or extra cars. Open concept floor plan and an updated...... |
3008 SqFt House In Chestertown |
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3008 SqFt House In ChestertownChestertown, MD$1,650,000
Homes for Sale
Hilltop Farm C. 1810 in historic Chestertown includes 113 acres with waterfront on Langford Creek off the Chester River. Property includes large 8 feet deep fresh water pond and impoundment.Perc...... |
1012 SqFt House In Chestertown |
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1012 SqFt House In ChestertownChestertown, MD$37,000
Homes for Sale
This is a HUD Home that the government's Department of Housing and Urban Development foreclosed on after the original owner stopped making payments. This home is sold via an auction process whereby...... |
934 SqFt House In Chestertown |
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934 SqFt House In ChestertownChestertown, MD$539,000
Homes for Sale
Shows great! Nice hardwood floors, beautiful millwork, built ins were custom made, granite counter tops, open floor plan, living room has a gas fireplace, private master bedroom suite with an...... |
832 SqFt House In Chester Harbor |
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832 SqFt House In Chester HarborChestertown, MD$189,900
Homes for Sale
Cute as a button cottage! Wood flooring, beautifully updated with a wonderful gas fireplace, built in cabinets and shelving. Lots of thought went into this home. All on one level, the crawlspace...... |
1584 SqFt House In Chestertown |
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1584 SqFt House In ChestertownChestertown, MD$325,000
Homes for Sale
Lovingly renovated home in the heart of historic Chestertown, just walking distance to all the shops and restaurants. Original details have been retained throughout the home, including original...... | |
2200 SqFt House In Chestertown |
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2200 SqFt House In ChestertownChestertown, MD$599,900
Homes for Sale
You will appreciate peaceful living in this waterfront community on the Chester River just minutes from historic Chestertown. A light-filled and spacious open floor plan is wonderful for enjoying...... |