Elevate Property Group
  • Home
  • Explore
    1. All Listings
    2. New & Coming
  • Services
    1. Buyer's Advantage
    2. Seller's Path
  • About
    1. Meet the Team
    2. Connect
  • Home Valuation
  • Mortgage Calculator
Register
/
Sign In
Price
  • Any
  • $ 100,000
  • $ 150,000
  • $ 200,000
  • $ 400,000
  • $ 800,000
  • Any
  • $ 200,000
  • $ 300,000
  • $ 400,000
  • $ 600,000
  • $ 1,000,000
    Beds Tap two numbers to select a range
    Any
    1
    2
    3
    4
    5+
    Baths Tap two numbers to select a range
    Any
    1
    2
    3
    4
    5+
  • List
  • Mixed
  • Map
Neighborhood: Chestertown, Chestertown, MD
Virtual Tour
Map
18 Properties Available In Chestertown

18 Properties Available In Chestertown

  • Default
  • Price-High To Low
  • Price-Low To High
  • Newest Listings
  • Beds (Most)
  • Baths (Most)
  • Year Built (Newest)
  • Square Feet (Biggest)
MD >Chestertown >Chestertown >
Market Insights
115 ACORN DR, Chestertown, MD 21620
1/40
Active

$296,000

2 Beds3 Baths1,864 SqFt

115 ACORN DR, Chestertown, MD 21620

MLS# MDKE2006360

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
108 OAK LEAF DR, Chestertown, MD 21620
1/39
Active

$299,500

2 Beds3 Baths1,867 SqFt

108 OAK LEAF DR, Chestertown, MD 21620

MLS# MDKE2006224

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
103 SUTTON WAY, Chestertown, MD 21620
1/53
Active

$550,000

5 Beds4 Baths3,816 SqFt

103 SUTTON WAY, Chestertown, MD 21620

MLS# MDKE2006344

Listed by TTR Sotheby's International Realty

Bright MLS (BMLS)
202 WALDO DR, Chestertown, MD 21620
1/28
Under Contract

$340,000

3 Beds2 Baths2,055 SqFt

202 WALDO DR, Chestertown, MD 21620

MLS# MDKE2006260

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
301 LINCOLN DR, Chestertown, MD 21620
1/40
Price Dropped by $10K

$299,900

3 Beds2 Baths1,152 SqFt

301 LINCOLN DR, Chestertown, MD 21620

MLS# MDKE2006170

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
231 RICHARD DR, Chestertown, MD 21620
1/51
Price Dropped by $129K

$1,150,000

5 Beds3 Baths2,956 SqFt

231 RICHARD DR, Chestertown, MD 21620

MLS# MDKE2005900

Listed by TTR Sotheby's International Realty

Bright MLS (BMLS)
117 WATER ST N #1A, 1B, 2A, & 2B, Chestertown, MD 21620
1/73
Active

$1,600,000

7 Beds5 Baths5,400 SqFt

117 WATER ST N #1A, 1B, 2A, & 2B, Chestertown, MD 21620

MLS# MDKE2006158

Listed by TTR Sotheby's International Realty

Bright MLS (BMLS)
117 WATER ST N #1A, Chestertown, MD 21620
1/46
Active

$685,000

3 Beds3 Baths3,000 SqFt

117 WATER ST N #1A, Chestertown, MD 21620

MLS# MDKE2006162

Listed by TTR Sotheby's International Realty

Bright MLS (BMLS)
117 WATER ST N #2A, Chestertown, MD 21620
1/24
Active

$375,000

2 Beds1 Bath787 SqFt

117 WATER ST N #2A, Chestertown, MD 21620

MLS# MDKE2006166

Listed by TTR Sotheby's International Realty

Bright MLS (BMLS)
117 WATER ST N #2B, Chestertown, MD 21620
1/23
Active

$350,000

1 Bed1 Bath850 SqFt

117 WATER ST N #2B, Chestertown, MD 21620

MLS# MDKE2006168

Listed by TTR Sotheby's International Realty

Bright MLS (BMLS)
117 WATER ST N #1B, Chestertown, MD 21620
1/20
Active

$200,000

1 Bed1 Bath700 SqFt

117 WATER ST N #1B, Chestertown, MD 21620

MLS# MDKE2006164

Listed by TTR Sotheby's International Realty

Bright MLS (BMLS)
110 TRAFFORD DR, Chestertown, MD 21620
1/22
Price Dropped by $15K

$450,000

4 Beds3 Baths2,880 SqFt

110 TRAFFORD DR, Chestertown, MD 21620

MLS# MDKE2005964

Listed by RE/MAX Advantage Realty

Bright MLS (BMLS)
218 CAMELOT DR, Chestertown, MD 21620
1/45
Price Dropped by $15K

$510,000

5 Beds4 Baths3,932 SqFt

218 CAMELOT DR, Chestertown, MD 21620

MLS# MDKE2005982

Listed by Coldwell Banker Realty

Bright MLS (BMLS)
311 DEVON DR, Chestertown, MD 21620
1/41
Price Dropped by $26K

$499,000

4 Beds3 Baths3,504 SqFt

311 DEVON DR, Chestertown, MD 21620

MLS# MDKE2005930

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
LITTLE HARBOR WAY #1, Chestertown, MD 21620
1/25
Active

$1,459,000

3 Beds3 Baths2,231 SqFt

LITTLE HARBOR WAY #1, Chestertown, MD 21620

MLS# MDKE2005768

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
105 HIGH ST, Chestertown, MD 21620
1/48
Active

$1,395,500

5 Beds5 Baths3,243 SqFt

105 HIGH ST, Chestertown, MD 21620

MLS# MDKE2005890

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
100 ADELA WAY, Chestertown, MD 21620
1/67
Under Contract

$498,500

4 Beds4 Baths3,799 SqFt

100 ADELA WAY, Chestertown, MD 21620

MLS# MDKE2005636

Listed by Berkshire Hathaway HomeServices PenFed Realty

Bright MLS (BMLS)
LITTLE HARBOR WAY #1, Chestertown, MD 21620
1/29
Active

$1,800,000

4 Beds4 Baths3,540 SqFt

LITTLE HARBOR WAY #1, Chestertown, MD 21620

MLS# MDKE2004992

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
  • 1

explore listings near Chestertown

  • Open House
  • Price Reduced
  • Virtual Tour
  • 3D Tour
default
    • Home
      About
      1. Meet the Team
      2. Connect
    • Explore
      1. All Listings
      2. New & Coming
      Home Valuation
    • Services
      1. Buyer's Advantage
      2. Seller's Path
      Mortgage Calculator
Elevate Property Group
Elevate Property Group

+1(240) 737-5000 info@welcomefromelevate.com

1441 McCormick Dr STE 1020, Upper Marlboro, MD, 20774, USA

Get My App

Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.
QUICK SEARCH
  • Asheville, NC For Sale
  • A O Dille Farm, Upper Marlboro, MD For Sale
  • Balmoral, Upper Marlboro, MD For Sale
  • Beacon Hill, Upper Marlboro, MD For Sale
  • Beech Tree North Village, Upper Marlboro, MD For Sale
  • Belmont Crest, Upper Marlboro, MD For Sale
  • Brock Hall, Upper Marlboro, MD For Sale
  • Brock Hall, Upper Marlboro, MD For Sale
default
    • Home
      About
      1. Meet the Team
      2. Connect
    • Explore
      1. All Listings
      2. New & Coming
      Home Valuation
    • Services
      1. Buyer's Advantage
      2. Seller's Path
      Mortgage Calculator
Elevate Property Group
Elevate Property Group

+1(240) 737-5000 info@welcomefromelevate.com

1441 McCormick Dr STE 1020, Upper Marlboro, MD, 20774, USA

Get My App

Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.