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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
New
7755 Waterview Ln, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2.5 Baths
  • 4,730 SqFt

7755 Waterview Ln, CHESTERTOWN

$975,000
228 S Water St, CHESTERTOWN
  • Residential
  • 3 Beds
  • 3.5 Baths
  • 0 SqFt

228 S Water St, CHESTERTOWN

$950,000
Landing Ln #25, CHESTERTOWN
  • Residential
  • 4 Beds
  • 3.5 Baths
  • 2,784 SqFt

Landing Ln #25, CHESTERTOWN

$949,900
8049 Quaker Neck Rd, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2 Baths
  • 1,660 SqFt

8049 Quaker Neck Rd, CHESTERTOWN

$848,000
Landing Ln #12, CHESTERTOWN
  • Residential
  • 3 Beds
  • 3.5 Baths
  • 2,200 SqFt

Landing Ln #12, CHESTERTOWN

$815,000
Landing Ln #11, CHESTERTOWN
  • Residential
  • 3 Beds
  • 3.5 Baths
  • 2,200 SqFt

Landing Ln #11, CHESTERTOWN

$805,000
Landing Ln #37, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2.5 Baths
  • 1,964 SqFt

Landing Ln #37, CHESTERTOWN

$725,000
106-1/2 Water St N #1/2, CHESTERTOWN
  • Residential
  • 4 Beds
  • 3.5 Baths
  • 2,866 SqFt

106-1/2 Water St N #1/2, CHESTERTOWN

$695,000 ↓ $55,000
118 Westwood Ln, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2 Baths
  • 2,248 SqFt

118 Westwood Ln, CHESTERTOWN

$625,000 ↓ $14,900
New
234 Blakefield Dr, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2.5 Baths
  • 2,400 SqFt

234 Blakefield Dr, CHESTERTOWN

$553,500
New
193 Westwood Ln, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2 Baths
  • 3,572 SqFt

193 Westwood Ln, CHESTERTOWN

$550,000
8757 Orchard Dr, CHESTERTOWN
  • Residential
  • 2 Beds
  • 2.5 Baths
  • 2,210 SqFt

8757 Orchard Dr, CHESTERTOWN

$529,000 ↓ $11,000

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Listing information last updated on April 26th, 2024 at 5:15am EDT.