LPT Realty
  • Home
  • Buy
    1. View All Listings
    2. Steps to Buying Your Home
  • Sell
    1. Steps to Sell Your Home
    2. Home Valuation
    3. Sold Listings
  • About
    1. Contact Us
    2. About
  • Neighborhoods
  • Renovate Now
  • Simply Elite Exclusives
    1. Client Events
    2. Testimonials
    3. Military Relocation
    4. 30 Day Guarantee
    5. VIP Buyer Program
    6. Referrals
    7. Our Preferred Partners
    8. Market Reports
  • Join Us At LPT
    1. Learn More About LPT
  • Register
  • Sign In
Filters Reset
1 Filter
Kitchens
Reset
1 Filter
1 Filter Applied

New Construction
Price
  • Any
  • $ 100,000
  • $ 150,000
  • $ 200,000
  • $ 400,000
  • $ 800,000
  • Any
  • $ 200,000
  • $ 300,000
  • $ 400,000
  • $ 600,000
  • $ 1,000,000
Days On Site
Advanced
Less Than
Days
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
Unit Level

Exterior Stories
Main Level Bedrooms
Frontage
Age Restriction
Maintenance
Unit Floor Number
Keyword
Price per Sqft
Tax Amount
Stories
Num Of Pets
Full Bathrooms
Half Bathrooms
Condo Fee
Num of Units
Acres
SqFt
Switch to Acre
Sqft
Sqft
Lot Size
Switch to Acre
Sqft
Sqft
Year Built
Monthly HOA Fee
Land Lease Fee
Maintenance Fee
Assessed Value

Fireplace Number

Parking Space
Carport Spaces
Garage Space

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

37 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
304 HILLTOP LN, Chestertown, MD 21620
New

$209,900

304 HILLTOP LN, Chestertown, MD 21620

3 Beds3 Baths1,199 SqFt

MLS# MDKE2005440

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
132 PROSPECT ST, Chestertown, MD 21620
New

$69,900

132 PROSPECT ST, Chestertown, MD 21620

2 Beds1 Bath910 SqFt

MLS# MDKE2005444

Listed by ANR Realty, LLC

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

$699,000

206 S WATER ST, Chestertown, MD 21620

4 Beds4 Baths2,008 SqFt

MLS# MDKE2005362

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
201 BIRCH RUN RD, Chestertown, MD 21620
Active

$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)
206 BARROLL DR, Chestertown, MD 21620
Price Dropped by $10K

$480,000

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)
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)
103 LANDING LN, Chestertown, MD 21620
Active

$569,000

103 LANDING LN, Chestertown, MD 21620

2 Beds3 Baths2,100 SqFt

MLS# MDKE2004972

Listed by Gunther-McClary Real Estate

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)
212 LANDING LN, Chestertown, MD 21620
Active

$759,000

212 LANDING LN, Chestertown, MD 21620

3 Beds4 Baths

MLS# MDKE2004782

Listed by Gunther-McClary Real Estate

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)
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)
128 N QUEEN ST #3, Chestertown, MD 21620
New

$1,450

128 N QUEEN ST #3, Chestertown, MD 21620

1 Bed1 Bath900 SqFt

MLS# MDKE2005464

Listed by Brenton Realty Group

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
defaultUntitled design (99)New-MRP-Logojpg-removebg-preview (1)
      Home
      Buy
      1. View All Listings
      2. Steps to Buying Your Home
      Sell
      1. Steps to Sell Your Home
      2. Home Valuation
      3. Sold Listings
      About
      1. Contact Us
      2. About
      Renovate Now
      Simply Elite Exclusives
      1. Client Events
      2. Testimonials
      3. Military Relocation
      4. 30 Day Guarantee
      5. VIP Buyer Program
      6. Referrals
      7. Our Preferred Partners
      8. Market Reports
      Join Us At LPT
      1. Learn More About LPT
LPT Realty

Joseph & Danielle Dedekind

+1(703) 244-8787 joe@simplyelitehometeam.com

TREC Consumer Protection Notice

TREC Information About Brokerage Services

Get My App

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

Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

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.
defaultUntitled design (99)New-MRP-Logojpg-removebg-preview (1)
      Home
      Buy
      1. View All Listings
      2. Steps to Buying Your Home
      Sell
      1. Steps to Sell Your Home
      2. Home Valuation
      3. Sold Listings
      About
      1. Contact Us
      2. About
      Renovate Now
      Simply Elite Exclusives
      1. Client Events
      2. Testimonials
      3. Military Relocation
      4. 30 Day Guarantee
      5. VIP Buyer Program
      6. Referrals
      7. Our Preferred Partners
      8. Market Reports
      Join Us At LPT
      1. Learn More About LPT
LPT Realty

Joseph & Danielle Dedekind

+1(703) 244-8787 joe@simplyelitehometeam.com

TREC Consumer Protection Notice

TREC Information About Brokerage Services

Get My App

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

Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

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.