Chestertown

Chestertown Real Estate Listings
7755 Waterview Ln, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2.5 Baths
  • 4,730 SqFt

7755 Waterview Ln, CHESTERTOWN

$1,350,000
22153 1st Point Rd, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2 Baths
  • 3,153 SqFt

22153 1st Point Rd, CHESTERTOWN

$985,000 ↓ $90,000
New
9556 Chantilly Farm Ln, CHESTERTOWN
  • Residential
  • 3 Beds
  • 4 Baths
  • 2,276 SqFt

9556 Chantilly Farm Ln, CHESTERTOWN

$895,000
9831 Breezecroft Ln, CHESTERTOWN
  • Residential
  • 3 Beds
  • 3.5 Baths
  • 2,352 SqFt

9831 Breezecroft Ln, CHESTERTOWN

$835,000
114 N Water St, CHESTERTOWN
  • Residential
  • 4 Beds
  • 3.5 Baths
  • 3,640 SqFt

114 N Water St, CHESTERTOWN

$685,000 ↓ $30,000
106 Goose Roost Ln, CHESTERTOWN
  • Residential
  • 6 Beds
  • 4 Baths
  • 5,366 SqFt

106 Goose Roost Ln, CHESTERTOWN

$600,100
115 Pintail Rd, CHESTERTOWN
  • Residential
  • 2 Beds
  • 1.5 Baths
  • 1,144 SqFt

115 Pintail Rd, CHESTERTOWN

$549,000 ↓ $41,000
311 Mayfair Dr, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2 Baths
  • 2,700 SqFt

311 Mayfair Dr, CHESTERTOWN

$525,000 ↓ $14,000
New
8616 Orchard Dr, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2.5 Baths
  • 2,422 SqFt

8616 Orchard Dr, CHESTERTOWN

$490,000 ↑ $15,000
New
108 Harlan Loop, CHESTERTOWN
  • Residential
  • 5 Beds
  • 2.5 Baths
  • 3,692 SqFt

108 Harlan Loop, CHESTERTOWN

$485,000
300 Gatling Dr, CHESTERTOWN
  • Residential
  • 4 Beds
  • 2 Baths
  • 2,619 SqFt

300 Gatling Dr, CHESTERTOWN

$479,900
New
106 Camelot Dr, CHESTERTOWN
  • Residential
  • 4 Beds
  • 3.5 Baths
  • 3,760 SqFt

106 Camelot Dr, CHESTERTOWN

$439,000

Chestertown Homes for Sale

All Listings $100,000 - $200,000 $200,000 - $300,000
$300,000 - $400,000 $400,000 - $500,000 $500,000 - $600,000
$600,000 - $700,000 $800,000 - $900,000 $900,000 - $1,000,000
Over $1,000,000
105 Snyder Ln, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2 Baths
  • 1,240 SqFt

105 Snyder Ln, CHESTERTOWN

$249,900 ↓ $15,000
107 Chester Arms Dr, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2 Baths
  • 1,140 SqFt

107 Chester Arms Dr, CHESTERTOWN

$229,900
105 Chester Arms Dr, CHESTERTOWN
  • Residential
  • 3 Beds
  • 2 Baths
  • 1,140 SqFt

105 Chester Arms Dr, CHESTERTOWN

$229,900 ↓ $70,000
103 Chester Arms Dr, CHESTERTOWN
  • Residential
  • 3 Beds
  • 1.5 Baths
  • 1,260 SqFt

103 Chester Arms Dr, CHESTERTOWN

$229,900 ↓ $70,000
631 High St, CHESTERTOWN
  • Residential
  • 3 Beds
  • 1.5 Baths
  • 1,234 SqFt

631 High St, CHESTERTOWN

$207,500
336 Truslow Rd, CHESTERTOWN
  • Residential
  • 1 Beds
  • 1 Baths
  • 600 SqFt

336 Truslow Rd, CHESTERTOWN

$199,900 ↓ $29,600
102 Conley Dr, CHESTERTOWN
  • Residential
  • 3 Beds
  • 1.5 Baths
  • 1,280 SqFt

102 Conley Dr, CHESTERTOWN

$184,900
900 Deep Landing Rd, CHESTERTOWN
  • Residential
  • 0 Beds
  • 1 Baths
  • 402 SqFt

900 Deep Landing Rd, CHESTERTOWN

$150,000 ↓ $49,000

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Listing information last updated on June 30th, 2022 at 10:01pm EDT.