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
New
10856 Foreston Rd, CHESTERTOWN
  • Residential
  • 2 Beds
  • 1 Baths
  • 1,380 SqFt

10856 Foreston Rd, CHESTERTOWN

$435,000
23430 Cloquet Rd, CHESTERTOWN
  • Residential
  • 4 Beds
  • 4 Baths
  • 3,504 SqFt

23430 Cloquet Rd, CHESTERTOWN

$385,000
113 Trafford Dr, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2.5 Baths
  • 2,490 SqFt

113 Trafford Dr, CHESTERTOWN

$374,900 ↓ $5,000
8656 Maryland Pkwy, CHESTERTOWN
  • Residential
  • 4 Beds
  • 3 Baths
  • 3,806 SqFt

8656 Maryland Pkwy, CHESTERTOWN

$350,000
123 Trafford Dr, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2.5 Baths
  • 2,404 SqFt

123 Trafford Dr, CHESTERTOWN

$339,000
107 Rolling Rd, CHESTERTOWN
  • Residential
  • 4 Beds
  • 3 Baths
  • 1,756 SqFt

107 Rolling Rd, CHESTERTOWN

$337,500
New
205 Princess Anne Dr, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2 Baths
  • 1,492 SqFt

205 Princess Anne Dr, CHESTERTOWN

$329,000
10740 Millbrook Dr, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2.5 Baths
  • 2,570 SqFt

10740 Millbrook Dr, CHESTERTOWN

$325,000
10749 Millbrook Dr, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2.5 Baths
  • 1,344 SqFt

10749 Millbrook Dr, CHESTERTOWN

$310,000 ↓ $19,900
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
New
N/A, CHESTERTOWN
  • Residential
  • 3 Beds
  • 1.5 Baths
  • 2,300 SqFt

N/A, CHESTERTOWN

$289,000

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Listing information last updated on September 24th, 2021 at 8:32pm EDT.