Chestertown

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

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$829,000

↓ $36,000

106 Queen St S, CHESTERTOWN

3 Beds 3.5 Baths 2,472 SqFt Residential MLS® # MDKE2006152

Chesapeake Real Estate Associates, LLC

$824,900

8999 Orchard Dr, CHESTERTOWN

5 Beds 3.5 Baths 4,353 SqFt Residential MLS® # MDKE2006786

Coldwell Banker Chesapeake Real Estate Company

$813,900

104 Landing Ln, CHESTERTOWN

3 Beds 3.5 Baths 2,192 SqFt Residential MLS® # MDKE2005952

Gunther-McClary Real Estate

$799,900

106 Landing Ln, CHESTERTOWN

3 Beds 3.5 Baths 2,092 SqFt Residential MLS® # MDKE2005892

Gunther-McClary Real Estate

$799,000

7828 Country Club Ln, CHESTERTOWN

3 Beds 2.5 Baths 2,857 SqFt Residential MLS® # MDKE2006736

Cross Street Realtors LLC

$786,900

#35 Landing Ln, CHESTERTOWN

3 Beds 2.5 Baths 1,964 SqFt Residential MLS® # MDKE2005956

Gunther-McClary Real Estate

$765,900

#37 Landing Ln, CHESTERTOWN

3 Beds 2.5 Baths 1,964 SqFt Residential MLS® # MDKE2005960

Gunther-McClary Real Estate

$753,500

#36 Landing Ln, CHESTERTOWN

3 Beds 2.5 Baths 1,964 SqFt Residential MLS® # MDKE2005958

Gunther-McClary Real Estate

$750,000

↓ $45,000

201 N Lynchburg St, CHESTERTOWN

0 Beds 1 Bath 2,045 SqFt Residential MLS® # MDKE2006142

RE/MAX Associates-Hockessin

$750,000

216 Birch Run Rd, CHESTERTOWN

3 Beds 2.5 Baths 2,176 SqFt Residential MLS® # MDKE2006896

TTR Sotheby's International Realty

$685,000

117 Water St N #1a, CHESTERTOWN

3 Beds 3 Baths 3,000 SqFt Residential MLS® # MDKE2006162

TTR Sotheby's International Realty

Open House

$675,000

212 Washington Ave, CHESTERTOWN

5 Beds 3 Baths 2,838 SqFt Residential

Open House

Sat, Oct 3rd, 2026 @ 10am - 1pm

MLS® # MDKE2007016

Coldwell Banker Chesapeake Real Estate Company

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