Chestertown

Chestertown Real Estate Listings
101 N Water St, CHESTERTOWN
  • Residential
  • 6 Beds
  • 6 Baths
  • 7,440 SqFt

101 N Water St, CHESTERTOWN

$4,150,000 ↓ $250,000
201 S Water St, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2 Baths
  • 4,452 SqFt

201 S Water St, CHESTERTOWN

$2,100,000
7250 Pentridge Ln, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2.5 Baths
  • 0 SqFt

7250 Pentridge Ln, CHESTERTOWN

$1,450,000 ↓ $200,000
7250 Pentridge Ln, CHESTERTOWN
  • Farm
  • 4 Beds
  • 2.5 Baths
  • 0 SqFt

7250 Pentridge Ln, CHESTERTOWN

$1,450,000 ↓ $200,000
7755 Waterview Ln, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2.5 Baths
  • 4,730 SqFt

7755 Waterview Ln, CHESTERTOWN

$1,350,000
9831 Breezecroft Ln, CHESTERTOWN
  • Residential
  • 3 Beds
  • 3.5 Baths
  • 2,352 SqFt

9831 Breezecroft Ln, CHESTERTOWN

$859,000
954 High St, CHESTERTOWN
  • Residential
  • 6 Beds
  • 6 Baths
  • 6,334 SqFt

954 High St, CHESTERTOWN

$775,000 ↓ $20,000
114 N Water St, CHESTERTOWN
  • Residential
  • 4 Beds
  • 3.5 Baths
  • 3,640 SqFt

114 N Water St, CHESTERTOWN

$749,000
302 Park Row, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2.5 Baths
  • 3,600 SqFt

302 Park Row, CHESTERTOWN

$695,000
10840 Foreston Rd, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2.5 Baths
  • 2,049 SqFt

10840 Foreston Rd, CHESTERTOWN

$599,000
7071 Pomona Rd, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2.5 Baths
  • 2,544 SqFt

7071 Pomona Rd, CHESTERTOWN

$590,000 ↓ $35,000
211 Landing Ln, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2.5 Baths
  • 2,200 SqFt

211 Landing Ln, CHESTERTOWN

$559,000 ↑ $10,000

Chestertown Homes for Sale

All Listings Under $100,000 $100,000 - $200,000
$200,000 - $300,000 $300,000 - $400,000 $400,000 - $500,000
$500,000 - $600,000 $600,000 - $700,000 $700,000 - $800,000
$800,000 - $900,000 Over $1,000,000
209 Landing Ln, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2.5 Baths
  • 2,400 SqFt

209 Landing Ln, CHESTERTOWN

$539,000
105 S Queen St, CHESTERTOWN
  • Residential
  • 3 Beds
  • 1.5 Baths
  • 2,456 SqFt

105 S Queen St, CHESTERTOWN

$520,000
Leverage Rd, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2.5 Baths
  • 1,800 SqFt

Leverage Rd, CHESTERTOWN

$499,900
9540 Fairlee Rd, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2 Baths
  • 2,795 SqFt

9540 Fairlee Rd, CHESTERTOWN

$449,900 ↓ $37,600
109 Lyons Ln, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2.5 Baths
  • 1,944 SqFt

109 Lyons Ln, CHESTERTOWN

$439,000 ↓ $10,000
New
809 S Meadowview Dr, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2.5 Baths
  • 2,592 SqFt

809 S Meadowview Dr, CHESTERTOWN

$399,900
204 David Dr, CHESTERTOWN
  • Residential
  • 4 Beds
  • 1.5 Baths
  • 2,362 SqFt

204 David Dr, CHESTERTOWN

$349,000
213 Byford Dr, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2 Baths
  • 1,277 SqFt

213 Byford Dr, CHESTERTOWN

$330,000
108 Maple Ave, CHESTERTOWN
  • Residential
  • 5 Beds
  • 1.5 Baths
  • 2,460 SqFt

108 Maple Ave, CHESTERTOWN

$329,000
117 Tuxedo Rd, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2 Baths
  • 1,680 SqFt

117 Tuxedo Rd, CHESTERTOWN

$289,000
10561 Millbrook Dr, CHESTERTOWN
  • Residential
  • 3 Beds
  • 1.5 Baths
  • 1,050 SqFt

10561 Millbrook Dr, CHESTERTOWN

$289,000 ↓ $10,000
8990 Georgetown Rd, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2 Baths
  • 1,440 SqFt

8990 Georgetown Rd, CHESTERTOWN

$279,000 ↑ $30,000

Bright MLS Logo© 2022 BRIGHT, All Rights Reserved. Information deemed reliable but not guaranteed. The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Coldwell Banker Chesapeake Real Estate Company participates, and is provided by BRIGHT through a licensing agreement. Real estate listings held by brokerage firms other than Coldwell Banker Chesapeake Real Estate Company are marked with the IDX logo 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 Closed or are no longer being offered for sale. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller.

Listing information last updated on January 20th, 2022 at 11:03am EST.