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
New
10743 Millbrook Dr, CHESTERTOWN
  • Residential
  • 4 Beds
  • 3 Baths
  • 2,009 SqFt

10743 Millbrook Dr, CHESTERTOWN

$199,000
New
104 Kennedy Dr, CHESTERTOWN
  • Residential
  • 3 Beds
  • 1.5 Baths
  • 1,152 SqFt

104 Kennedy Dr, CHESTERTOWN

$149,900
9225 Fairlee Rd, CHESTERTOWN
  • Residential
  • 1 Beds
  • 1 Baths
  • 584 SqFt

9225 Fairlee Rd, CHESTERTOWN

$129,900
5713 Johnsontown Rd, CHESTERTOWN
  • Residential
  • 2 Beds
  • 1 Baths
  • 1,400 SqFt

5713 Johnsontown Rd, CHESTERTOWN

$85,000 ↓ $14,000
6769 Quaker Neck Rd, CHESTERTOWN
  • Residential
  • 3 Beds
  • 1 Baths
  • 1,040 SqFt

6769 Quaker Neck Rd, CHESTERTOWN

$59,000 ↓ $23,000

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Listing information last updated on January 20th, 2022 at 11:33am EST.