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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$295,000

240 Round Top Rd, CHESTERTOWN

3 Beds 2 Baths 1,132 SqFt Residential MLS® # MDQA2018166

Clark & Co Realty, LLC

$289,900

21146 Montana Ave, CHESTERTOWN

2 Beds 1.5 Baths 1,500 SqFt Residential MLS® # MDKE2006858

Cross Street Realtors LLC

Open House

$279,000

10540 Tonopah Rd, CHESTERTOWN

3 Beds 2 Baths 1,404 SqFt Residential

Open House

Sat, Aug 15th, 2026 @ 11am - 1pm

MLS® # MDKE2006880

Doug Ashley Realtors, LLC

$275,000

↓ $24,000

611 Cannon St, CHESTERTOWN

2 Beds 1.5 Baths 920 SqFt Residential MLS® # MDKE2005906

Select Land & Homes, LLC

$275,000

↓ $10,000

956 Washington Ave, CHESTERTOWN

3 Beds 1 Bath 1,248 SqFt Residential MLS® # MDKE2006394

Doug Ashley Realtors, LLC

$275,000

↓ $9,900

104 Acorn Dr, CHESTERTOWN

3 Beds 2.5 Baths 1,900 SqFt Residential MLS® # MDKE2006668

Cross Street Realtors LLC

$264,900

121 Metcalf Rd, CHESTERTOWN

3 Beds 1.5 Baths 0 SqFt Residential MLS® # MDKE2006678

Real Broker, LLC - Chester

Open House

$259,900

115 Metcalf Rd, CHESTERTOWN

3 Beds 1.5 Baths 1,280 SqFt Residential

Open House

Thu, Aug 13th, 2026 @ 5pm - 7pm

MLS® # MDKE2006826

Real Broker, LLC - Chester

$240,000

107 Conley Dr, CHESTERTOWN

3 Beds 1 Bath 1,140 SqFt Residential MLS® # MDKE2006828

Benson & Mangold, LLC

$239,900

↓ $7,100

104 Conley Dr, CHESTERTOWN

3 Beds 1.5 Baths 1,280 SqFt Residential MLS® # MDKE2006686

Cummings & Co. Realtors

New

$225,000

533 Round Top Rd, CHESTERTOWN

4 Beds 1.5 Baths 1,800 SqFt Residential MLS® # MDQA2018038

EXP Realty, LLC

New

$205,000

202 Pine St, CHESTERTOWN

3 Beds 1 Bath 1,341 SqFt Residential MLS® # MDKE2006888

Coldwell Banker Chesapeake Real Estate Company

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