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
400 River Rd, CHESTERTOWN
  • Residential
  • 5 Beds
  • 5 Baths
  • 7,932 SqFt

400 River Rd, CHESTERTOWN

$1,800,000
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
7755 Waterview Ln, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2.5 Baths
  • 4,730 SqFt

7755 Waterview Ln, CHESTERTOWN

$1,350,000
4652 Cliffs City Rd, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2 Baths
  • 2,691 SqFt

4652 Cliffs City Rd, CHESTERTOWN

$945,000 ↑ $70,000
408 Pear Tree Point Rd, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2.5 Baths
  • 2,782 SqFt

408 Pear Tree Point Rd, CHESTERTOWN

$887,000
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
456 Pear Tree Point Rd, CHESTERTOWN
  • Residential
  • 2 Beds
  • 2 Baths
  • 1,834 SqFt

456 Pear Tree Point Rd, CHESTERTOWN

$750,000
114 N Water St, CHESTERTOWN
  • Residential
  • 4 Beds
  • 3.5 Baths
  • 3,640 SqFt

114 N Water St, CHESTERTOWN

$749,000

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
N/A, CHESTERTOWN
  • Residential
  • 3 Beds
  • 1.5 Baths
  • 2,300 SqFt

N/A, CHESTERTOWN

$284,000 ↓ $5,000
100 Malone Ave, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2 Baths
  • 2,444 SqFt

100 Malone Ave, CHESTERTOWN

$275,000 ↓ $10,000
8891 Georgetown Rd, CHESTERTOWN
  • Residential
  • 5 Beds
  • 3 Baths
  • 1,600 SqFt

8891 Georgetown Rd, CHESTERTOWN

$270,000 ↓ $15,000
9850 Fairlee Rd, CHESTERTOWN
  • Residential
  • 3 Beds
  • 1 Baths
  • 1,120 SqFt

9850 Fairlee Rd, CHESTERTOWN

$264,900
105 Lyons Ln, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2 Baths
  • 1,192 SqFt

105 Lyons Ln, CHESTERTOWN

$260,000
336 Truslow Rd, CHESTERTOWN
  • Residential
  • 1 Beds
  • 1 Baths
  • 600 SqFt

336 Truslow Rd, CHESTERTOWN

$249,500
New
421 Pear Tree Point Rd W, CHESTERTOWN
  • Residential
  • 2 Beds
  • 1 Baths
  • 997 SqFt

421 Pear Tree Point Rd W, CHESTERTOWN

$249,000
8990 Georgetown Rd, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2 Baths
  • 1,440 SqFt

8990 Georgetown Rd, CHESTERTOWN

$249,000
New
917 Round Top Rd, CHESTERTOWN
  • Residential
  • 3 Beds
  • 1 Baths
  • 1,008 SqFt

917 Round Top Rd, CHESTERTOWN

$219,500
153 Longfellow Dr, CHESTERTOWN
  • Residential
  • 3 Beds
  • 1.5 Baths
  • 1,376 SqFt

153 Longfellow Dr, CHESTERTOWN

$215,000

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 October 23rd, 2021 at 4:30am EDT.