View 240 Round Top Landing Road Chestertown, MD MLS# MDQA2009012
$3,995,000
3

Beds

3.1

Baths

4,804

Sq.Ft.

240 Round Top Landing Road

Chestertown, MD

Bright
Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY
View 204 Truslow Farm Lane Chestertown, MD MLS# MDQA2009684
$729,000
4

Beds

2.1

Baths

2,945

Sq.Ft.

204 Truslow Farm Lane

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 234 Blakefield Drive Chestertown, MD MLS# MDQA2008918
  • New Construction
1 of 3
$553,500
3

Beds

2.1

Baths

2,400

Sq.Ft.

234 Blakefield Drive

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 112 Sheaffer Road Chestertown, MD MLS# MDQA2009698
  • Virtual Tour
1 of 48
$525,000
4

Beds

2.1

Baths

2,864

Sq.Ft.

112 Sheaffer Road

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View Truslow Farm Lane # LOT 3 Chestertown, MD MLS# MDQA2008922
$519,900
Studio

Beds

0.0

Baths

Truslow Farm Lane # LOT 3

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View Truslow Farm Lane # LOT 4 Chestertown, MD MLS# MDQA2008924
$519,900
Studio

Beds

0.0

Baths

Truslow Farm Lane # LOT 4

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View Truslow Farm Lane # LOT 2 Chestertown, MD MLS# MDQA2008920
$497,000
Studio

Beds

0.0

Baths

Truslow Farm Lane # LOT 2

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 210 Truslow Farm Lane Chestertown, MD MLS# MDQA2008926
$425,000
Studio

Beds

0.0

Baths

210 Truslow Farm Lane

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 231 Blakefield Drive Chestertown, MD MLS# MDQA2008916
  • New Construction
1 of 4
$422,000
3

Beds

2.0

Baths

1,600

Sq.Ft.

231 Blakefield Drive

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 109 Coleman Drive Chestertown, MD MLS# MDQA2009174
  • Virtual Tour
1 of 49
$409,000
4

Beds

3.0

Baths

1,792

Sq.Ft.

109 Coleman Drive

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 481 Pear Tree Point Road Chestertown, MD MLS# MDQA2009262
$399,900
3

Beds

2.1

Baths

1,512

Sq.Ft.

481 Pear Tree Point Road

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 477 Pear Tree Point Road Chestertown, MD MLS# MDQA2009842
$399,900
3

Beds

2.1

Baths

1,512

Sq.Ft.

477 Pear Tree Point Road

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 707 Round Top Road Chestertown, MD MLS# MDQA2008894
$340,000
3

Beds

2.0

Baths

1,296

Sq.Ft.

707 Round Top Road

Chestertown, MD

Bright
Courtesy of THE HOGANS AGENCY
View 120 Edmore Road Chestertown, MD MLS# MDQA2009860
  • Recently Listed
1 of 9
OPEN HOUSE: Friday 5/31 3:30 PM - 6:30 PM
$335,000
3

Beds

1.0

Baths

1,144

Sq.Ft.

120 Edmore Road

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 310 Longfellow Drive Chestertown, MD MLS# MDQA2009320
$329,000
3

Beds

2.0

Baths

1,560

Sq.Ft.

310 Longfellow Drive

Chestertown, MD

Bright
Courtesy of BERKSHIRE HATHAWAY HOMESERVICE HOMESALE REALTY
View 112 Pine Chip Road Chestertown, MD MLS# MDQA2008762
$325,000
3

Beds

1.0

Baths

1,248

Sq.Ft.

112 Pine Chip Road

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 124 Wilton Road Chestertown, MD MLS# MDQA2009548
$289,900
3

Beds

1.0

Baths

1,056

Sq.Ft.

124 Wilton Road

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 729 Rosin Drive Chestertown, MD MLS# MDQA2009822
  • Virtual Tour
1 of 32
$289,900
3

Beds

1.0

Baths

1,056

Sq.Ft.

729 Rosin Drive

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 235 Burchard Sawmill Road Chestertown, MD MLS# MDQA2009482
$289,000
2

Beds

2.0

Baths

864

Sq.Ft.

235 Burchard Sawmill Road

Chestertown, MD

Bright
Courtesy of VILLAGE REAL ESTATE COMPANY LLC
View 332 Truslow Road Chestertown, MD MLS# MDQA2009122
$274,000
2

Beds

1.0

Baths

1,408

Sq.Ft.

332 Truslow Road

Chestertown, MD

Bright
Courtesy of BLACKWELL REAL ESTATE, LLC

About Chestertown

Listings in Chestertown, MD

24

Estimated median home price

$370,950
Chestertown MD Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Chestertown, Maryland real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Chestertown, MD.

Homes for Sale by Price in Chestertown, MD

Price Count
$0 - 100K 2
$100K - 200K 0
$200K - 300K 5
$300K - 400K 7
$400K - 500K 4
$500K - 600K 4
$600K - 700K 0
$700K - 800K 1
$800K - 900K 0
$900K - 1M 0
$1M - Max 1

Homes for Sale by Type in Chestertown, MD

Property Type Count
Single Family 18
Townhouse 0
Condo 0
Commercial 0
Rental 0
Lots and Land 6
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 5/31/2024)

Information deemed reliable but not guaranteed.

Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BrightMLS Broker ReciprocitySM program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Weichert, Realtors® participates, and is provided by BrightMLS through a licensing agreement.

Real estate listings held by brokerage firms other than Weichert, Realtors® are marked with the Broker Reciprocity icon (a little black house) and detailed information about each listing includes the name of the listing broker.

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale.

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