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

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 $900,000 - $1,000,000 Over $1,000,000
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
7968 Aldan Dr, CHESTERTOWN
  • Residential
  • 5 Beds
  • 3.5 Baths
  • 5,200 SqFt

7968 Aldan Dr, CHESTERTOWN

$689,000
21175 Georgia Ave, CHESTERTOWN
  • Residential
  • 3 Beds
  • 1 Baths
  • 1,718 SqFt

21175 Georgia Ave, CHESTERTOWN

$669,000 ↓ $10,000
0 Muirfield Dr, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2.5 Baths
  • 0 SqFt

0 Muirfield Dr, CHESTERTOWN

$605,000 ↑ $20,000
211 Landing Ln, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2.5 Baths
  • 2,200 SqFt

211 Landing Ln, CHESTERTOWN

$559,000 ↑ $10,000
209 Landing Ln, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2.5 Baths
  • 2,400 SqFt

209 Landing Ln, CHESTERTOWN

$539,000
25320 Fox Chase Drive, CHESTERTOWN
  • Residential
  • 3 Beds
  • 3 Baths
  • 2,160 SqFt

25320 Fox Chase Drive, CHESTERTOWN

$509,000 ↓ $6,000
101 Landing Ln, CHESTERTOWN
  • Residential
  • 3 Beds
  • 3.5 Baths
  • 3,300 SqFt

101 Landing Ln, CHESTERTOWN

$499,900 ↓ $50,100
109 Lyons Ln, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2.5 Baths
  • 1,944 SqFt

109 Lyons Ln, CHESTERTOWN

$449,000
New
113 Church Meadow Ct, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2.5 Baths
  • 1,426 SqFt

113 Church Meadow Ct, CHESTERTOWN

$439,500
New
5645 N Church Hill Rd S, CHESTERTOWN
  • Residential
  • 3 Beds
  • 3 Baths
  • 1,944 SqFt

5645 N Church Hill Rd S, CHESTERTOWN

$439,000

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Listing information last updated on September 24th, 2021 at 7:16pm EDT.