Chestertown MD Real Estate & Homes for Sale

112 Properties Found

The median home value in Chestertown, MD is $214,250. This is higher than the county median home value of $180,000. The national median home value is $177,414. The average price of homes sold in Chestertown, MD is $214,250. Approximately 37.21% of Chestertown homes are owned, compared to 43.01% rented, while 19.78% are vacant. Chestertown real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you see a property you’re interested in, contact a Chestertown real estate agent to arrange a tour today!
Learn more about Chestertown Real Estate.


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$650,000

310 Hickory Lane Chestertown, MD 21620

Beds:
3
Baths:
3.00
Sq.Ft.:
3,300
Status:
NEW LISTING
MLS#:
QA9842553
Type:
Single Family
Subdivision:
Pheasant
Lot size:
20 Acres
Year built:
2002
A broker reciprocity listing Courtesy: Keller Williams Flagship of Maryland
View additional info

Custom home situated on 20 acres. 600' of River front property with permittable Boardwalk and Pier. Every window provides a fantastic view. Three River rooms (one on each floor) provide amazing views of the Chester River and the areas Wildlife. Home offers charm with many wood accents throughout. Adjacent wetlands ; the opposite side of the river cannot be developed.

$225,000

211 Waldo Drive Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
KE9838024
Type:
Single Family
Subdivision:
Byford Development
Lot size:
0.34 Acres
Year built:
1982
A broker reciprocity listing Courtesy: Rosendale Realty
View additional info

So close to all Chestertown's quaint attractions yet still has the neighborhood feel. Cozy home with beautiful brick fireplace, Exposed Beams, High Ceilings with sky lights! Open concept Kitchen, Hardwood floors, large deck off back Sunroom along with the attached garage and separate -Laundry/Mudd room make this house a must see! Make your appointment soon!

$359,000

204 Birch Run Road Chestertown, MD 21620

Beds:
3
Baths:
3.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
KE9833432
Type:
Single Family
Subdivision:
Mile Tree Village
Lot size:
0.45 Acres
Year built:
1988
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Co
View additional info

Mile Tree Village is a special place; a private quiet Cul-de-Sac. Walk into Chestertown, Washington College or the Chester River. Nicely fenced large rear yard with views of the large deck, sunny Florida room and the Chester river.This cape has wood floors, 2 fireplaces, attached garage and a first floor master. Just enjoy the serenity of this great spot.

$159,000

109 Pine Street Chestertown, MD 21620

Beds:
3
Baths:
1.00
Sq.Ft.:
1,200
Status:
NEW LISTING
MLS#:
KE9841067
Type:
Single Family
Subdivision:
College Heights
Lot size:
0.22 Acres
Year built:
1953
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
View additional info

Adorable & Affordable! Close to the College and just a short walk to downtown Chestertown, this cozy cottage sits on .22 acres and boasts a heart pine accent wall, further accented by a wood burning fireplace, hardwood floors and other original details that compliment its retro charm. The large rear deck off of the kitchen expands the living space to the outdoors, which is ideal for entertaining.

$149,500

120 Queen Street Chestertown, MD 21620

Beds:
4
Baths:
2.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
KE9840459
Type:
Single Family
Subdivision:
Historic Chestertown
Lot size:
0.11 Acres
Year built:
1920
A broker reciprocity listing Courtesy: Select Land & Homes, LLC
View additional info

This house is a great renovation project with a fantastic location. Located in Historic Downtown Chestertown, this house is an easy walk to restaurants, shops and the water. The property has a unique backyard and offers off street private parking.

$300,000

25155 Chestertown Road Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
1,456
Status:
NEW LISTING
MLS#:
KE9840426
Type:
Single Family
Subdivision:
Fannels Meadow
Lot size:
4.16 Acres
Year built:
1920
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Co
View additional info

Wonderful farmhouse with new upgraded kitchen -- granite counter tops and island with breakfast bar. First floor master can be used as dining or 2nd living. Pellet stove on first level keeps whole house toasty. Small barn with horse stall and shed for potting or storage. Raised garden beds with easy access to water pump. Fenced in yard with dog house.

$69,900

23412 Sandpiper Road Chestertown, MD 21620

Beds:
2
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9837875
Type:
Single Family
Subdivision:
Tbd
Lot size:
0.34 Acres
Year built:
1995
A broker reciprocity listing Courtesy: Village Real Estate Company LLC
View additional info

Value priced home in water access community. Don't let the work scare you away, this home is just waiting for the savvy buyer to turn their sweat into real EQUITY! Large home with plenty of potential, deck, paved driveway, hot tub, and cathedral ceilings. Community features boat ramp and small pier on Worton Creek. Come take a look TODAY!

$165,000

314 Hilltop Lane Chestertown, MD 21620

Beds:
3
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9837579
Type:
Townhouse
Subdivision:
Tim Dills Sub
Lot size:
0.08 Acres
Year built:
2005
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Co
View additional info

Best Townhouse in Hilltop. Owner had Wood floors installed on first floor. Quiet, end unit with views of farmland behind unit. Open floor plan. Small patio in rear for your BBQ and space for a small garden. Very well maintained. Convenient to everything Chestertown!

$99,900

220 Burchard Sawmill Road Chestertown, MD 21620

Beds:
3
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA9835126
Type:
Single Family
Subdivision:
None
Lot size:
0.96 Acres
Year built:
1979
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
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3 bedroom/1 bath rambler on almost an acre with rear porch. Living room, separate dining room. Large detached garage. Sold as-is. Seller makes no guarantees or warranties. Buyer's agent is to pay a $150 offer management fee at closing of any accepted offer. All offers must be submitted via PropOffers.

$279,000

208 Leeds Court Chestertown, MD 21620

Beds:
4
Baths:
3.00
Sq.Ft.:
1,860
Status:
Active
MLS#:
KE9834820
Type:
Single Family
Subdivision:
Coventry Farms
Lot size:
0.5 Acres
Year built:
2001
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
View additional info

Spacious and open Cape Cod w/ both an attached 2-car & a detached 2-car garage w/upstairs rec room! Florida room offers views of the secluded backyard that is enclosed by a privacy fence and trex deck. 4 bedrooms, 3 full bathrooms, wood floors throughout the interior and situated on a cul-de-sac in Coventry Farms with No HOA Fee and No Front Foot Fee! Owner will consider renting for $1,800/mo

$119,900

141 Snyder Lane Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA9833630
Type:
Single Family
Subdivision:
Double Creek Woods
Lot size:
0.58 Acres
Year built:
1994
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
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Very affordable home on a wooded cul-de-sac. Furnace was new in the past couple years. Living room and dining room are open to the kitchen with some newer appliances. There is a one car garage with electric and an additional shed. There is even a small deck to enjoy relaxing on.

$189,900

7571 Quaker Neck Road Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9833440
Type:
Single Family
Subdivision:
Quaker Estates
Lot size:
0.37 Acres
Year built:
1962
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

Renovations are 99%+/- complete! Updates and upgrades include new Bryant HVAC, renovated tiled baths, kitchen w/granite counters and tiled floors, all new kitchen appliances, new tiled entrance, open floor plan,new lighting & plumbing fixtures throughout, family room with tray ceiling, recessed lighting, refinished wood floors in living room and bedrooms and so much more! Looks absolutely amazing!

$175,000

203 Cedar Street Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9824971
Type:
Single Family
Subdivision:
College Heights
Lot size:
0.41 Acres
Year built:
1963
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
View additional info

Well maintained traditional brick home has GREAT bones! Great room addition has a wood stove for warmth & ambiance, screened porch, finished basement w/ kitchenette, roof & A/C are ~10 years new, fully fenced yard with dog run & storage shed, two bay attached carport... in the desirable neighborhood of College Heights! Only a few minutes from downtown, stores & just three blocks from the college!

$585,000

5179 Quaker Neck Road Chestertown, MD 21620

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9831975
Type:
Single Family
Subdivision:
In Heart Of Kent County Farms
Lot size:
3.22 Acres
Year built:
1890
A broker reciprocity listing Courtesy: Maryland Heritage Properties
View additional info

INTRIGUING OPPORTUNITY! This lovely old brick chapel, ca.1890, was built and used as a Methodist Chapel. Never to be used again as a house of worship, it is now offered to a fortunate person to design a weekend or year-round treasure. Pastor Mowbray, a mason, is credited with the construction. Approved for septic. Please call for commission schedule.

$270,000

503 Cannon Street Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9828680
Type:
Single Family
Subdivision:
Historic Chestertown
Lot size:
0.17 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Co
View additional info

Great house on desirable Cannon St. Many original details including trim, moldings, Fireplace mantel, and a grand staircase! Wood floors complete this gem. Kitchen and bathrooms need some updating, but work fine. Lovely front porch with porch swing that is screened. Deep back yard with Gazebo and shed. Off street parking! Walk to everything downtown Chestertown!

$569,000

117 Water Street Chestertown, MD 21620

Beds:
7
Baths:
7.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9826371
Type:
Single Family
Subdivision:
Chestertown
Lot size:
0.33 Acres
Year built:
1885
A broker reciprocity listing Courtesy: Long & Foster Real Estate, Inc.
View additional info

Outstanding Opportunity! Seven unit apartment building located in historic Chestertown on the Chester River. Live in the first floor owners suite with screened in porch and rent the other six units, ample parking. All within easy access to shops, restaurants, galleries, docks and Washington College. Generous yard, patio and gardens overlooking the water. Wait list for rental units.

$53,900

206 Lincoln Drive Chestertown, MD 21620

Beds:
3
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9826007
Type:
Single Family
Subdivision:
Washington Park
Lot size:
0.52 Acres
Year built:
1965
A broker reciprocity listing Courtesy: Village Real Estate Company LLC
View additional info

Great investment opportunity at an affordable price. Half acre lot with mature shade tree in the backyard, newer siding, roof, and windows. Community park located right around the corner. Call today!

$125,000

111 College Avenue Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9825837
Type:
Single Family
Subdivision:
Chestertown
Lot size:
0.07 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Village Real Estate Company LLC
View additional info

Located in historic downtown Chestertown. Walking distance to Washington College, shopping, local restaurants, arts and entertainment, winery and distillery all just a short stroll away. Just near the new Chestertown Police Station. Preview this ideal home today!

$19,000

24590 Willow Oak Lane Chestertown, MD 21620

Beds:
2
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9825150
Type:
Single Family
Subdivision:
Chestertown
Lot size:
1 Acres
Year built:
1920
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

Great secluded location. House is a tear down. Well and septic on property but condition unknown. I acre, some wooded and some cleared area. Minutes from downtown Chestertown, Bring your plans!

$533,000

105 Queen Street S Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
2,456
Status:
Active
MLS#:
KE9824983
Type:
Single Family
Subdivision:
Historic Chestertown
Lot size:
0.09 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Maryland Heritage Properties
View additional info

Inviting & comfortable residence. Wrap-around porch. Tree-line street immediate to shops, cultural events & Chester River. Professionally designed renovations. Lovely kitchen/family room overlooking a garden. Perfect location for a potential master bath. Drawings available. Within Historic District & A&E District. Just blocks from Washington College. NOTE: Please do not park neighbors' driveway!

$99,500

2201 Pondtown Road Chestertown, MD 21620

Beds:
3
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA9824907
Type:
Single Family
Subdivision:
None
Lot size:
1 Acres
Year built:
1955
A broker reciprocity listing Courtesy: CR Realty
View additional info

Great starter home, backs to woods for extra privacy. Easy commute to many locations just off of 301. New roof in 2015. Central heat and air condition, large kitchen. Laundry room. Needs some cosmetics, but should pass VA, FHA, USDA loans. Call today

$69,500

409 Calvert Street Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9823741
Type:
Townhouse
Subdivision:
Calvert Homes
Lot size:
0.05 Acres
Year built:
1992
A broker reciprocity listing Courtesy: Sommers Enterprises, Inc.
View additional info

Low maintenance, interior town home close enough to walk to all Chestertown amenities. Recent upgrades of interior painting, laminate floor installation, kitchen cabinet redo., tree trimming. Park off street in rear. Consistent market rental history for investor buyers.

$89,900

8915 Georgetown Road Chestertown, MD 21620

Beds:
2
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9822977
Type:
Single Family
Subdivision:
Chestertown
Lot size:
0.33 Acres
Year built:
1948
A broker reciprocity listing Courtesy: W.F. Beauchamp Realty
View additional info

COMPLETELY RENOVATED ALL BRICK RANCHER FOR UNDER 150K!!! NEW KITCHEN, NEW BATHS, NEW WINDOWS, NEW FLOORING, NEW ROOF, NEW PAINT, NEW TRIM, NEW FIXTURES, NEW WATER HEATER!! IT'S ALL NEW!!DON'T MISS IT BEFORE IT'S GONE!!!

$139,900

Shortal Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
1,232
Status:
Active
MLS#:
KE9821421
Type:
Single Family
Subdivision:
Quaker Estates
Lot size:
0.34 Acres
A broker reciprocity listing Courtesy: Rosendale Realty
View additional info

TO BE BUILT. ANOTHER GREAT STICK BUILT HOME AT AN AFFORDABLE PRICE. 1232 SQFT RANCHER COMPLETE 90-120 FROM PERMIT. GREAT OPEN KITCHEN AND LIVING ROOM, NICE APPLIANCE PACKAGE, STILL TIME TO PICK FLOOR PLAN, CABINETS, COUNTERS, FLOORING, AND COLOR. THIS PROPERTY IS A GREAT OPTION FOR MOST ANY BUYER. OTHER LOTS AND PLANS AVAILABLE. LOT 38 PIC IS AN ARTIST RENDITION. MHBR #3717

$319,900

515 Cannon Street Chestertown, MD 21620

Beds:
3
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE9818795
Type:
Single Family
Subdivision:
Chestertown
Lot size:
0.15 Acres
Year built:
2016
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

Almost finished!! Construction should be completed by January 2017. The Hardiplank siding has already been started and the wood flooring will be finished soon. Amazing 2" x 6" exterior wall construction with a concrete crawl space, fire suppression system, open floor plan and small back porch. Master bedroom on the main level with double vanities and walk in closet. Shared driveway. MHBR #846

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The data on this web site comes in part from Metropolitan Regional Information Systems (MRIS). The listings presented on behalf of MRIS may come from many different brokers but all MRIS listings may not be visible on this site. Information is believed to be reliable, but not guaranteed.

Chestertown MD Real Estate Listings Provided By:

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