Honest Real Estate
  • Home
  • Buy
    1. All Listings
    2. Featured Listings
    3. Sold Listings
  • Sell
    1. Sell My Home
    2. Home Valuation
  • Neighborhoods
  • About
    1. About Us
    2. Contact Us
    3. Reviews
  • Market Snapshot
  • Register
  • Sign In
Filters Reset
1 Filter
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
  • Any
  • 1
  • 2
  • 3
  • 4
  • 5
  • Any
  • 1
  • 2
  • 3
  • 4
  • 5
Baths
  • Any
  • 1
  • 2
  • 3
  • 4
  • 5
  • Any
  • 1
  • 2
  • 3
  • 4
  • 5
Reset
1 Filter
1 Filter Applied

Days On Site
Advanced
Less Than
Days
Unit Level

SqFt
Switch to Acre
Sqft
Sqft
Lot Size
Switch to Acre
Sqft
Sqft
Price per Sqft
Monthly HOA Fee
Year Built
Stories
Kitchens
Acres
Full Bathrooms
Half Bathrooms
Frontage
Tax Amount
Land Lease Fee
Keyword
Maintenance Fee
Assessed Value

Fireplace Number

Parking Space
Garage Space
Carport Spaces

Open House
Has Picture
New
Hot
Virtual Tour
3D Tour
Price Reduced
Save Search (2)
Save your search to get Alerts
38 Properties
Map

38 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
201 BIRCH RUN RD, Chestertown, MD 21620
Open Sat 11AM-1PM

$495,000

201 BIRCH RUN RD, Chestertown, MD 21620

3 Beds2 Baths1,588 SqFt

MLS# MDKE2005380

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
103 LANDING LN, Chestertown, MD 21620
Open Sat 11AM-1PM

$569,000

103 LANDING LN, Chestertown, MD 21620

2 Beds3 Baths2,100 SqFt

MLS# MDKE2004972

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
212 LANDING LN, Chestertown, MD 21620
Open Sat 11AM-1PM

$759,000

212 LANDING LN, Chestertown, MD 21620

3 Beds4 Baths

MLS# MDKE2004782

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
206 BARROLL DR, Chestertown, MD 21620
Active

$490,000

206 BARROLL DR, Chestertown, MD 21620

3 Beds2 Baths1,820 SqFt

MLS# MDKE2005094

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
624 HIGH ST, Chestertown, MD 21620
Active

$240,000

624 HIGH ST, Chestertown, MD 21620

2 Beds1 Bath1,290 SqFt

MLS# MDKE2005274

Listed by Tesla Realty Group, LLC

Bright MLS (BMLS)
132 PROSPECT ST, Chestertown, MD 21620
Price Dropped by $5K

$74,900

132 PROSPECT ST, Chestertown, MD 21620

2 Beds1 Bath910 SqFt

MLS# MDKE2005276

Listed by ANR Realty, LLC

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

$1,459,000

LITTLE HARBOR WAY #1, Chestertown, MD 21620

3 Beds3 Baths2,315 SqFt

MLS# MDKE2004992

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
300 HILLTOP LN, Chestertown, MD 21620
Price Dropped by $15K

$220,000

300 HILLTOP LN, Chestertown, MD 21620

3 Beds3 Baths1,200 SqFt

MLS# MDKE2005004

Listed by Coldwell Banker Chesapeake Real Estate Company

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

$1,395,500

105 HIGH ST, Chestertown, MD 21620

5 Beds5 Baths3,243 SqFt

MLS# MDKE2005002

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
226 S WATER ST, Chestertown, MD 21620
Active

$998,000

226 S WATER ST, Chestertown, MD 21620

3 Beds4 Baths3,782 Sqft Lot

MLS# MDKE2004940

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
110 FLYING CLOUD COURT, Chestertown, MD 21620
Active

$349,900

110 FLYING CLOUD COURT, Chestertown, MD 21620

3 Beds3 Baths1,856 SqFt

MLS# MDKE2004850

Listed by Berkshire Hathaway HomeServices Homesale Realty

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

$725,000

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

3 Beds3 Baths

MLS# MDKE2004206

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
349 HIGH ST, Chestertown, MD 21620
Active

$395,000

349 HIGH ST, Chestertown, MD 21620

7 Beds4 Baths3,664 SqFt

MLS# MDKE2004076

Listed by Coldwell Banker Chesapeake Real Estate Company

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

$399,000

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

2 Beds1 Bath787 SqFt

MLS# MDKE2003742

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
117 N WATER ST N #3B, Chestertown, MD 21620
Price Dropped by $48K

$299,900

117 N WATER ST N #3B, Chestertown, MD 21620

1 Bed1 Bath652 SqFt

MLS# MDKE2003722

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
228 S WATER ST, Chestertown, MD 21620
Price Dropped by $52K

$898,000

228 S WATER ST, Chestertown, MD 21620

3 Beds4 Baths2,592 Sqft Lot

MLS# MDKE2001612

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
114 CONLEY DR, Chestertown, MD 21620
New

$1,700

114 CONLEY DR, Chestertown, MD 21620

3 Beds2 Baths1,280 SqFt

MLS# MDKE2005304

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
201 N LYNCHBURG ST, Chestertown, MD 21620
Active

$995,000

201 N LYNCHBURG ST, Chestertown, MD 21620

3,527 SqFt

MLS# MDKE2005278

Listed by RE/MAX Associates-Hockessin

Bright MLS (BMLS)
128 N QUEEN ST #4, Chestertown, MD 21620
Active

$1,450

128 N QUEEN ST #4, Chestertown, MD 21620

1 Bed1 Bath1,455 SqFt

MLS# MDKE2005242

Listed by Brenton Realty Group

Bright MLS (BMLS)
329 HIGH ST, Chestertown, MD 21620
Active

$1,250,000

329 HIGH ST, Chestertown, MD 21620

4,500 SqFt

MLS# MDKE2005172

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
CROMWELL CLARK RD, Chestertown, MD 21620
Active

$3,000,000

CROMWELL CLARK RD, Chestertown, MD 21620

87.34 Acres

MLS# MDKE2005156

Listed by The Land Group

Bright MLS (BMLS)
120 SPEER RD, Chestertown, MD 21620
Active

$1,250,000

120 SPEER RD, Chestertown, MD 21620

9,604 SqFt

MLS# MDKE2005054

Listed by Mackenzie Commercial R E SVCS, LLC

Bright MLS (BMLS)
HAACKE DRIVE LOT 3, Chestertown, MD 21620
Price Dropped by $93K

$225,000

HAACKE DRIVE LOT 3, Chestertown, MD 21620

0.96 Acres

MLS# MDKE2004648

Listed by Select Land & Homes, LLC

Bright MLS (BMLS)
SCHEELER ROAD LOT 2, Chestertown, MD 21620
Price Dropped by $99K

$250,000

SCHEELER ROAD LOT 2, Chestertown, MD 21620

0.93 Acres

MLS# MDKE2004650

Listed by Select Land & Homes, LLC

Bright MLS (BMLS)
  • 1
  • 2

explore listings near Chestertown

  • Open House
  • Price Reduced
  • Virtual Tour
  • 3D Tour
default
Honest Real Estate

Scott Kelly License ID: 371332

+1(267) 340-1034 scott@honestrealestate.com

12320 Academy Rd, Philadelphia, PA, 19154-1928, USA
    • Home
      About
      1. About Us
      2. Contact Us
      3. Reviews
    • Buy
      1. All Listings
      2. Featured Listings
      3. Sold Listings
      Market Snapshot
    • Sell
      1. Sell My Home
      2. Home Valuation

Get My App

Powered by Lofty Inc. Copyright 2025. 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.
default
Honest Real Estate

Scott Kelly License ID: 371332

+1(267) 340-1034 scott@honestrealestate.com

12320 Academy Rd, Philadelphia, PA, 19154-1928, USA
    • Home
      About
      1. About Us
      2. Contact Us
      3. Reviews
    • Buy
      1. All Listings
      2. Featured Listings
      3. Sold Listings
      Market Snapshot
    • Sell
      1. Sell My Home
      2. Home Valuation

Get My App

Powered by Lofty Inc. Copyright 2025. 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.