(443) 480-1181

Chestertown

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

101 N Water St, CHESTERTOWN

$4,400,000
8039 Quaker Neck Rd, CHESTERTOWN
  • Residential
  • 4 Beds
  • 3.5 Baths
  • 3,578 SqFt

8039 Quaker Neck Rd, CHESTERTOWN

$1,480,000 ↓ $70,000
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
9784 White Swan Ct, CHESTERTOWN
  • Residential
  • 5 Beds
  • 5.5 Baths
  • 5,001 SqFt

9784 White Swan Ct, CHESTERTOWN

$1,250,000
7710 Brices Mill Rd, CHESTERTOWN
  • Residential
  • 5 Beds
  • 3.5 Baths
  • 2,808 SqFt

7710 Brices Mill Rd, CHESTERTOWN

$975,000
128 Royston Shores Rd, CHESTERTOWN
  • Residential
  • 3 Beds
  • 3.5 Baths
  • 2,896 SqFt

128 Royston Shores Rd, CHESTERTOWN

$915,000 ↓ $35,000
New
408 Pear Tree Point Rd, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2.5 Baths
  • 2,782 SqFt

408 Pear Tree Point Rd, CHESTERTOWN

$887,000
4652 Cliffs City Rd, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2 Baths
  • 2,691 SqFt

4652 Cliffs City Rd, CHESTERTOWN

$875,000 ↓ $70,000
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

$795,000 ↓ $30,000
New
9036 Point Ln, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2.5 Baths
  • 2,590 SqFt

9036 Point Ln, CHESTERTOWN

$795,000
Next
View All & Refine Results Next

Chestertown Homes for Sale, $200,000 - $300,000

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 $900,000 - $1,000,000 Over $1,000,000
27320 Morgnec Rd, CHESTERTOWN
  • Residential
  • 3 Beds
  • 1.5 Baths
  • 3,724 SqFt

27320 Morgnec Rd, CHESTERTOWN

$299,900 ↓ $40,000
10561 Millbrook Dr, CHESTERTOWN
  • Residential
  • 3 Beds
  • 1.5 Baths
  • 1,050 SqFt

10561 Millbrook Dr, CHESTERTOWN

$299,000 ↓ $20,000
New
N/A, CHESTERTOWN
  • Residential
  • 3 Beds
  • 1.5 Baths
  • 2,300 SqFt

N/A, CHESTERTOWN

$289,000
100 Malone Ave, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2 Baths
  • 2,444 SqFt

100 Malone Ave, CHESTERTOWN

$285,000
105 Lyons Ln, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2 Baths
  • 1,192 SqFt

105 Lyons Ln, CHESTERTOWN

$260,000
106 Riverside Ter, CHESTERTOWN
  • Residential
  • 2 Beds
  • 1 Baths
  • 1,366 SqFt

106 Riverside Ter, CHESTERTOWN

$249,900
7539 Poplar Ave, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2 Baths
  • 1,232 SqFt

7539 Poplar Ave, CHESTERTOWN

$249,900
336 Truslow Rd, CHESTERTOWN
  • Residential
  • 1 Beds
  • 1 Baths
  • 600 SqFt

336 Truslow Rd, CHESTERTOWN

$249,500
New
114 Heath Rd, CHESTERTOWN
  • Residential
  • 3 Beds
  • 1 Baths
  • 1,560 SqFt

114 Heath Rd, CHESTERTOWN

$235,000
New
22402 Cross Rd, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2 Baths
  • 960 SqFt

22402 Cross Rd, CHESTERTOWN

$225,000
New
917 Round Top Rd, CHESTERTOWN
  • Residential
  • 3 Beds
  • 1 Baths
  • 1,008 SqFt

917 Round Top Rd, CHESTERTOWN

$219,500
150 Longfellow Dr, CHESTERTOWN
  • Residential
  • 3 Beds
  • 1 Baths
  • 1,056 SqFt

150 Longfellow Dr, CHESTERTOWN

$219,000

Bright MLS Logo© 2021 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 September 24th, 2021 at 8:17pm EDT.