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Chestertown MD Real Estate & Homes for Sale

120 Properties Found

The median home value in Chestertown, MD is $236,000 This is higher than the county median home value of $183,500. The national median home value is $185,800. The average price of homes sold in , is $. Approximately 41.87% of Chestertown homes are owned, compared to 42.32% rented, while 15.82% 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 Chestertown real estate agent to arrange a tour today !
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$309,900

241 Devon Drive Chestertown, MD 21620

Beds:
4
Baths:
4.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
KE10087768
Type:
Single Family
Subdivision:
Coventry Farms
Lot size:
0.259 Acres
Year built:
2006
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Beautiful home with gracious open floor plan. This property offers 4 bedrooms with 4 full baths, attached garage, and finished basement with a full bath and potential for further bedrooms or theater room. Conveniently located with a short drive to shopping and easy access to Rt. 301 and Rt. 50.

$667,500

219 Water Street UNIT 3 Chestertown, MD 21620

Beds:
4
Baths:
4.00
Sq.Ft.:
2,800
Status:
NEW LISTING
MLS#:
KE10086646
Type:
Condo/Townhouse
Subdivision:
Scott's Point
Year built:
2008
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Fabulous Townhouse in desirable Scott's Point. Great waterviews of the Chester River & Wilmer Park. 2 deeded boat slips. Open Floor plan is enhanced by beautiful wood floors and cabinets. Wonderful Gormet Kitchen opens to dining and living area. Balconies on each floor. First Floor Den options as bedroom. Large open airy rooms gives simple elegance with light. Walkable to everything downtown!

$75,000

8858 Georgetown Road Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
KE10086557
Type:
Single Family
Subdivision:
Georgetown
Lot size:
1 Acres
Year built:
1920
A broker reciprocity listing Courtesy: The Hogans Agency
View additional info

With a little TLC this home could be great again. Within a 10 min drive to downtown Chestertown, Rock Hall and Betterton.

$39,900

8891 Georgetown Road Chestertown, MD 21620

Beds:
4
Baths:
1.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
KE10085565
Type:
Single Family
Subdivision:
None
Lot size:
2.1 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Champion Realty, Inc.
View additional info

investor alert! Rehab opportunity sitting on over 2 acreas

$99,900

421 Calvert Street Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
KE10085462
Type:
Townhouse
Subdivision:
Calvert Homes
Lot size:
0.0462 Acres
Year built:
1992
A broker reciprocity listing Courtesy: RE/MAX Sails Inc.
View additional info

MOVE IN READY TOWNHOME WITH COVERED PARKING! Newly updated w/ new carpet and paint throughout, spacious living room, eat-in kitchen w/ sliders to rear yard, main level half bath, Master bedroom w/ dual entry bath, and 2 additional bedrooms, large rear fenced yard, and off street parking with carport!

$234,900

105 Pine Cove Lane Chestertown, MD 21620

Beds:
3
Baths:
3.00
Sq.Ft.:
1,460
Status:
NEW LISTING
MLS#:
QA10084152
Type:
Single Family
Subdivision:
Pine Cove
Lot size:
0.6117 Acres
Year built:
2014
A broker reciprocity listing Courtesy: Coldwell Banker Waterman Realty
View additional info

Beautiful home built in 2014!. Walking distance to the water & public pier. Cathedral ceilings. Wood floors. Master bedroom en suite with full bath. Ceramic tile in bathrooms. Lower level for additional family room or bedroom. Kitchen overlooks main living space for modern open air feel. Lots of windows for sunny natural lighting. Sealed Deck. 2 car garage. Newly painted. Water softener. Shed.

$424,900

520 Morgnec Road Chestertown, MD 21620

Beds:
5
Baths:
4.00
Sq.Ft.:
3,494
Status:
NEW LISTING
MLS#:
KE10078037
Type:
Single Family
Subdivision:
Chestertown
Lot size:
10.92 Acres
Year built:
2004
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Custom built wonderful home in the country, but convenient to everything. Wildlife abundant w/BONUS PARCEL providing 10+ acres. Lower level w/2 BR,1.5BA, den, sep.kitchen/dining space and living areas. Potential in-law space or great entertaining space. Covered porch, wraparound deck w/amazing views. Private drive away from road! High ceilings, 3 zone HVAC, Lots of options for expanded families!

$549,000

209 Rivershore Road Chestertown, MD 21620

Open House:

Saturday, 10/28

Beds:
2
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA10078797
Type:
Single Family
Subdivision:
Chestertown
Lot size:
1.67 Acres
Year built:
1978
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

Chester River Cottage. Beautiful Chester River Views, a pier about 25 feet from this home. Nice water depth, and the house is adorable. Two bedrooms, not counting the loft, 1.5 baths, carport and a full unfinished basement. Charming built in's, a covered porch on the water side of the home. Fantastic opportunity to be five minutes from Chestertown, if that, but in a private location.

$345,000

7 Cedar Chase Court Chestertown, MD 21620

Open House:

Saturday, 10/28 12:00-2:00PM

Beds:
4
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10079626
Type:
Single Family
Subdivision:
Mile Tree Village
Lot size:
0.4817 Acres
Year built:
1985
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

Imagine relaxing on your screened porch or wrap around deck overlooking your own little pond w/views of the Chester River in the distance, in a lazy cul-de sac, in a village setting in Chestertown. Imagine no more! The family room w/wood burning fireplace is just off the kitchen w/wood floors and granite counters. There is even an elevator from basement/garage area to main level. Energy efficient!

$314,995

10310 Hanesville Road Chestertown, MD 21620

Open House:

Saturday, 10/28 12:00-2:00PM

Beds:
4
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10077502
Type:
Single Family
Subdivision:
No
Lot size:
2.05 Acres
Year built:
1989
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

Peaceful living at its best.Only minutes from town ,shopping , parks, and public landings. This home has so much to offer with 2 acres of private, beautifully landscaped yard that is tree lined and partially fenced. Extra garage and barn with lean to in addition to the already attached 2 car garage.Updated appliances in the kitchen in fall 2017. Lots of space inside and out to suite everyone.

$165,000

2605 McGinnes Road Chestertown, MD 21620

Beds:
3
Baths:
1.00
Sq.Ft.:
1,555
Status:
Active
MLS#:
QA10076797
Type:
Single Family
Subdivision:
None
Lot size:
1.02 Acres
Year built:
1957
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Quaint house on 1+ acres with privacy from main road, just waiting for a little TLC. All weather enclosed breezeway with heat and AC. Hardwood floors throughout, built-ins and garage. New pressure tank and water softener in 2017. Property is sold strictly AS IS. More pictures to follow.

$995,000

9559 Chantilly Farm Lane Chestertown, MD 21620

Beds:
4
Baths:
3.00
Sq.Ft.:
3,778
Status:
Active
MLS#:
KE10075510
Type:
Single Family
Subdivision:
Chantilly Farm
Lot size:
30.45 Acres
Year built:
1955
A broker reciprocity listing Courtesy: TTR Sotheby's International Realty
View additional info

SPECTACULAR VIEWS FROM THIS 30 ACRE ESTATE ON THE CHESAPEAKE BAY WITH 1000 ft OF SHORE LINE AND GRADUAL SLOPE TO WATER, SANDY BEACH, GUEST COTTAGE, WINE CELLAR IN LARGE BASEMENT, 3 CAR GARAGE, GENERATOR, UNLIMITED WILDLIFE AND BEAUTY EVERYWHERE! FRESH WATER POND, TROMBE WALL, PASSIVE SOLAR BUILDING DESIGN IN FAMILY ROOM. HOUSE AND PROPERTY HAVE BEEN IMMACULATELY MAINTAINED.

$334,900

209 Birch Run Road Chestertown, MD 21620

Beds:
4
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10071557
Type:
Single Family
Subdivision:
Mile Tree Village
Lot size:
0.5562 Acres
Year built:
1978
A broker reciprocity listing Courtesy: Village Real Estate Company LLC
View additional info

This home has it all!. The gourmet kitchen has professional appliances. The open floor plan has several levels, w/ 4 bedrooms and 3 full baths, dining room, living room, great room and a sunroom that overlooks a shady back yard. The huge garage has a workshop area, built in storage cabinets and shelves. The lovely fenced side yard is a gardening paradise. This is a Fannie Mae Homepath Property.

$41,900

6749 Church Lane Chestertown, MD 21620

Beds:
2
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10071500
Type:
Single Family
Subdivision:
None
Lot size:
0.5 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Village Real Estate Company LLC
View additional info

Country Farmhouse Needing Restoration! Very unique early Kent County residence located on quiet side road. Views of countryside and not far from public landing at Cliffs City. Short drive to historic Chestertown and Washington College. This might make the perfect weekend getaway or investment for folks with vision, so show me the money and let's make a deal!

$283,000

1253 Philosophers Terrace Chestertown, MD 21620

Beds:
4
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10069719
Type:
Single Family
Subdivision:
Philosophers Court
Lot size:
0.168 Acres
Year built:
2007
A broker reciprocity listing Courtesy: Select Land & Homes, LLC
View additional info

This spacious 4BR 3.5BA Chestertown home features Brazilian Cherry wood floors, 1st and 2nd floor masters, two gas fireplaces, a large open family/dining/kitchen combo, insulated basement and updated appliances. Within walking distance to Downtown Chestertown and Washington College this convenient location offers all the benefits of Downtown living! Currently occupied producing $25,200 a year.

$200,000

109 Tamarack Road Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA10068589
Type:
Single Family
Subdivision:
Chester Harbor
Lot size:
0.3444 Acres
Year built:
1987
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

Very nice home, two story, wood floors on the main level, full unfinished basement, a wonderful wooded lot, screened porch, wood burning fireplace in the family room/kitchen combo area. Living room, dining room, three bedrooms, and 2 full baths. A back loading two car garage. Quiet street, near the community park. Lovely area, HOA is not mandatory but recommended! $30.00/year for water access

$169,000

204 Glen Street Chestertown, MD 21620

Beds:
3
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10067840
Type:
Single Family
Subdivision:
College Heights
Lot size:
0.2605 Acres
Year built:
1966
A broker reciprocity listing Courtesy: Champion Realty, Inc.
View additional info

Immaculate well-maintained brick home located in College Heights offers beautiful hardwood flooring, fireplace and carport. Third bedroom is presently being used as a dining room. Home is served with town water and sewer which is the most reasonable utilities in the county. This home is move-in like-new condition.

$140,000

308 Park Row Chestertown, MD 21620

Beds:
2
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10065862
Type:
Duplex
Subdivision:
Historic Chestertown
Lot size:
0.12 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Maryland Heritage Properties
View additional info

Fine location across from Fountain Park in heart of Historic District & A&E District. Advantages for artists A&E District (A&E details available). Perfect artist studio/retail space w/living quarters on 2nd & 3rd levels. Off Street parking plus parking in rear. C-2 zoning offers retail opportunities on 1st floor & apartment as income or living space. Price below accessed value.

$340,000

208 Queen Street S Chestertown, MD 21620

Beds:
2
Baths:
3.00
Sq.Ft.:
1,640
Status:
Active
MLS#:
KE10064553
Type:
Single Family
Subdivision:
Historic District Chestertown
Lot size:
0.0379 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
View additional info

Charming Victorian renovation in the heart of the Historic District located just a few blocks from the Chester River offers an open design, accented by restored wide-plank hardwood flooring and an abundance of natural light. The home features a freshly painted exterior, modern and energy-efficient mechanics/systems and a privacy fence enclosing a rear brick patio, great for entertaining!

$125,000

26712 Morgnec Road Chestertown, MD 21620

Beds:
2
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10060332
Type:
Single Family
Subdivision:
Chestertown
Lot size:
0.35 Acres
Year built:
1951
A broker reciprocity listing Courtesy: Long & Foster Real Estate, Inc.
View additional info

Chestertown - This 2bed/1bath contemporary with large fenced yard, cathedral ceiling, shed and country views. Own instead of rent today! Call for your showing today. Owner/Agent

$1,250,000

406 River Road Chestertown, MD 21620

Beds:
4
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA10056028
Type:
Single Family
Subdivision:
Sarah Skipper Lands
Lot size:
0.611 Acres
Year built:
1995
A broker reciprocity listing Courtesy: The Hogans Agency
View additional info

Located across the river from Historic Chestertown, this private, well landscaped, Dutch Colonial is the perfect getaway! Entertain with ease with the spacious open first floor and french doors leading to the waterfront deck, patio, pool, and hot tub. Sit out on the balcony from any of the 3 adjoining bedrooms and enjoy the views the Chester River has to offer - there is something for everyone!

$297,000

311 South Queen Chestertown, MD 21620

Beds:
3
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10055156
Type:
Condo/Townhouse
Subdivision:
N/A
Lot size:
0.054 Acres
Year built:
1999
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Affordable Chestertown town house with 1st floor bedroom overlooking Wilmer Park and the Chester River,located in town, near shops or restaurants. Nice rear patio or sit on the front porch and watch the boating. Marina near by for your boat. Inside Family room has wood burning fireplace, skylights,raised ceiling & opens to a screened porch overlooking the patio complete with pavers.

$1,250,000

6854 Pentridge Court Chestertown, MD 21620

Beds:
4
Baths:
4.00
Sq.Ft.:
2,940
Status:
Active
MLS#:
KE10055129
Type:
Single Family
Subdivision:
Langford Farm
Lot size:
2.45 Acres
Year built:
1997
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
View additional info

Extraordinary Waterfront WITH Pool Permit! Gourmet kitchen for the culinary artist, well-appointed detail throughout - from heated flooring to imported Mexican tile. 2 screened porches coupled w/ expansive views to the waterfront invite the outdoor tranquility into the residence. The highly efficient mechanics and systems will impress the energy conscious "smart home" buyer.

$124,000

115 Conley Drive Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
1,320
Status:
Active
MLS#:
KE10050834
Type:
Duplex
Subdivision:
Chester Arms
Lot size:
0.0459 Acres
Year built:
1989
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Fresh paint, new carpet, clean as a whistle and ready to move in! Nice glassed in porch overlooks small fenced back yard. Low maintenance both inside and out. Middle unit helps keep utilities low. 3 BD, 1 1/2 BA with lots of closet space. Close to shopping centers, Washington College and the historic district of Chestertown. Come and check it out!

$129,900

610 High Street Chestertown, MD 21620

Beds:
3
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10041501
Type:
Single Family
Subdivision:
Chestertown
Lot size:
0.1104 Acres
Year built:
1900
A broker reciprocity listing Courtesy: The Hogans Agency
View additional info

Spacious and affordable home located near the heart of Chestertown. walking distance to fine arts, restaurants and waterfront. Great location, close to elementary school and Washington College. Hardwood throughout with a large eat-in kitchen and recently renovated bathroom. Sizeable yard and on street parking.

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BRIGHT MLS - All information, regardless of source, should be verified by personal inspection by and/or with the appropriate professional(s). The information is not guaranteed. Measurements are solely for the purpose of marketing, may not be exact, and should not be relied upon for loan, valuation, or other purposes.

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