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
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
26885 Mallard Rd, CHESTERTOWN
  • Residential
  • 3 Beds
  • 3 Baths
  • 3,135 SqFt

26885 Mallard Rd, CHESTERTOWN

$1,200,000
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
7968 Aldan Dr, CHESTERTOWN
  • Residential
  • 5 Beds
  • 3.5 Baths
  • 5,200 SqFt

7968 Aldan Dr, CHESTERTOWN

$689,000

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
106 Devon Dr, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2.5 Baths
  • 1,700 SqFt

106 Devon Dr, CHESTERTOWN

$374,900 ↓ $5,000
New
112 Holly Ct, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2 Baths
  • 1,890 SqFt

112 Holly Ct, CHESTERTOWN

$325,000
New
107 N Kent St, CHESTERTOWN
  • Residential
  • 2 Beds
  • 1 Baths
  • 1,041 SqFt

107 N Kent St, CHESTERTOWN

$239,900
8926 Fairlee Rd, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2 Baths
  • 1,988 SqFt

8926 Fairlee Rd, CHESTERTOWN

$289,000 ↓ $10,000
302 Park Row, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2.5 Baths
  • 3,600 SqFt

302 Park Row, CHESTERTOWN

$695,000
208 N Queen St, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2.5 Baths
  • 3,240 SqFt

208 N Queen St, CHESTERTOWN

$485,000
105 S Queen St, CHESTERTOWN
  • Residential
  • 3 Beds
  • 1.5 Baths
  • 2,456 SqFt

105 S Queen St, CHESTERTOWN

$520,000
10598 Klamath Rd, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2 Baths
  • 1,499 SqFt

10598 Klamath Rd, CHESTERTOWN

$249,000
8421 Broad Neck Rd, CHESTERTOWN
  • Residential
  • 3 Beds
  • 1.5 Baths
  • 1,680 SqFt

8421 Broad Neck Rd, CHESTERTOWN

$269,000
New
207 Birch Run Rd, CHESTERTOWN
  • Residential
  • 2 Beds
  • 2.5 Baths
  • 1,472 SqFt

207 Birch Run Rd, CHESTERTOWN

$380,000
416 High St, CHESTERTOWN
  • Residential
  • 3 Beds
  • 3 Baths
  • 2,112 SqFt

416 High St, CHESTERTOWN

$495,000
New
8851 Georgetown Rd, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2 Baths
  • 1,500 SqFt

8851 Georgetown Rd, CHESTERTOWN

$279,900

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Listing information last updated on December 2nd, 2021 at 2:03pm EST.