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Chestertown, MD
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127 Properties Available

127 Properties Available

The average price in the selected areas has remained stable. Learn more
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  • Newest Listings
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  • Baths (Most)
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129 PARMA RD, Chestertown, MD 21620
1/5
Coming Soon

$330,000

3 Beds2 Baths1,170 SqFt

129 PARMA RD, Chestertown, MD 21620

MLS# MDQA2015862

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
10800 CLIFF RD, Chestertown, MD 21620
1/94
New

$1,495,000

5 Beds4 Baths5,241 SqFt

10800 CLIFF RD, Chestertown, MD 21620

MLS# MDKE2005898

Listed by Taylor Properties

Bright MLS (BMLS)
141 PROSPECT ST, Chestertown, MD 21620
1/16
New

$165,000

4 Beds2 Baths1,156 SqFt

141 PROSPECT ST, Chestertown, MD 21620

MLS# MDKE2006036

Listed by Taylor Properties

Bright MLS (BMLS)
201 GREENWOOD AVE, Chestertown, MD 21620
1/62
Under Contract

$495,000

4 Beds3 Baths3,984 SqFt

201 GREENWOOD AVE, Chestertown, MD 21620

MLS# MDKE2006030

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
24775 LANGFORD RD, Chestertown, MD 21620
1/36
Active

$319,900

3 Beds1 Bath1,008 SqFt

24775 LANGFORD RD, Chestertown, MD 21620

MLS# MDKE2005992

Listed by RE/MAX 1st Choice - Middletown

Bright MLS (BMLS)
6746 QUAKER NECK RD, Chestertown, MD 21620
1/50
Active

$445,000

5 Beds3 Baths3,371 SqFt

6746 QUAKER NECK RD, Chestertown, MD 21620

MLS# MDKE2006014

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
104 IRIS RD, Chestertown, MD 21620
1/36
Active

$379,000

3 Beds2 Baths1,700 SqFt

104 IRIS RD, Chestertown, MD 21620

MLS# MDQA2015798

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
110 TRAFFORD DR, Chestertown, MD 21620
1/26
Active

$475,000

4 Beds3 Baths2,880 SqFt

110 TRAFFORD DR, Chestertown, MD 21620

MLS# MDKE2005964

Listed by RE/MAX Advantage Realty

Bright MLS (BMLS)
22481 GOOSE HOLLOW DR, Chestertown, MD 21620
1/18
Price Dropped by $29K

$379,500

3 Beds2 Baths1,296 SqFt

22481 GOOSE HOLLOW DR, Chestertown, MD 21620

MLS# MDKE2006012

Listed by Realty Mark Cityscape

Bright MLS (BMLS)
218 CAMELOT DR, Chestertown, MD 21620
1/45
Active

$525,000

5 Beds4 Baths3,932 SqFt

218 CAMELOT DR, Chestertown, MD 21620

MLS# MDKE2005982

Listed by Coldwell Banker Realty

Bright MLS (BMLS)
303 CEDAR ST, Chestertown, MD 21620
1/26
Under Contract

$333,900

3 Beds3 Baths2,577 SqFt

303 CEDAR ST, Chestertown, MD 21620

MLS# MDKE2005970

Listed by Select Land & Homes, LLC

Bright MLS (BMLS)
596 CHESTERTOWN ST, Gaithersburg, MD 20878
1/73
Active

$835,000

4 Beds4 Baths2,540 SqFt

596 CHESTERTOWN ST, Gaithersburg, MD 20878

MLS# MDMC2210282

Listed by Coester Real Estate Services, LLC

Bright MLS (BMLS)
21111 TEXAS AVE, Chestertown, MD 21620
1/16
Under Contract

$370,000

3 Beds2 Baths1,680 SqFt

21111 TEXAS AVE, Chestertown, MD 21620

MLS# MDKE2005932

Listed by Keller Williams Select Realtors of Easton

Bright MLS (BMLS)
109 METCALF RD, Chestertown, MD 21620
1/27
Active

$264,900

3 Beds2 Baths1,280 SqFt

109 METCALF RD, Chestertown, MD 21620

MLS# MDKE2005968

Listed by Real Broker, LLC

Bright MLS (BMLS)
676 DEEP LANDING RD, Chestertown, MD 21620
1/24
Under Contract

$315,000

3 Beds3 Baths1,468 SqFt

676 DEEP LANDING RD, Chestertown, MD 21620

MLS# MDQA2015466

Listed by Cross Street Realtors LLC

Bright MLS (BMLS)
#25 LANDING LN, Chestertown, MD 21620
1/22
Active

$1,099,900

4 Beds4 Baths2,784 SqFt

#25 LANDING LN, Chestertown, MD 21620

MLS# MDKE2005954

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
102 LITTLE HARBOR WAY, Chestertown, MD 21620
1/23
Active

$839,500

3 Beds3 Baths1,964 SqFt

102 LITTLE HARBOR WAY, Chestertown, MD 21620

MLS# MDKE2005950

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
104 LANDING LN, Chestertown, MD 21620
1/24
Active

$813,900

3 Beds4 Baths2,192 SqFt

104 LANDING LN, Chestertown, MD 21620

MLS# MDKE2005952

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
#35 LANDING LN, Chestertown, MD 21620
1/26
Active

$786,900

3 Beds3 Baths1,964 SqFt

#35 LANDING LN, Chestertown, MD 21620

MLS# MDKE2005956

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
#37 LANDING LN, Chestertown, MD 21620
1/24
Active

$765,900

3 Beds3 Baths1,964 SqFt

#37 LANDING LN, Chestertown, MD 21620

MLS# MDKE2005960

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
#36 LANDING LN, Chestertown, MD 21620
1/26
Active

$753,500

3 Beds3 Baths1,964 SqFt

#36 LANDING LN, Chestertown, MD 21620

MLS# MDKE2005958

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
213 CENTRAL DR, Chestertown, MD 21620
1/23
Open Sun 12PM-2PM

$314,900

3 Beds2 Baths1,232 SqFt

213 CENTRAL DR, Chestertown, MD 21620

MLS# MDQA2015648

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
7521 PINE AVE, Chestertown, MD 21620
1/24
Under Contract

$250,000

3 Beds1 Bath1,040 SqFt

7521 PINE AVE, Chestertown, MD 21620

MLS# MDKE2005920

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
204 ROLLING RD, Chestertown, MD 21620
1/31
Open Sat 11AM-1PM

$345,000

3 Beds2 Baths2,296 SqFt

204 ROLLING RD, Chestertown, MD 21620

MLS# MDKE2005896

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
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Coldwell Banker Premier

CB Premier

+1(540) 269-5683 cbpadmin@premiermove.com

1682 S Pleasant Valley Rd, Winchester, VA, 22601, United States

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Steve DuBrueler, Broker

16 Offices Serving VA, WV, DC, MD, DE, PA, and NC

1682 S. Pleasant Valley Road, Winchester, VA 22601 

14 E. Piccadilly Street, Winchester, VA 22601

115 Aikens Center, Suite 21, Martinsburg, WV 25404 

415 South Street Suite C, Front Royal, VA 22630 

116 East German Street, Shepherdstown, WV 25443

1618 Orkney Grade, Suite A, Basye, VA 22810

200 S. Washington Street, Berkeley Springs, WV 25411

1950 Evelyn Byrd Avenue, Suite A, Harrisonburg, VA 22801

20184 Coastal Highway, Rehoboth Beach, DE 19971

800 Kings Highway, Lewes, DE 19958

22350 Sussex Highway, Seaford, DE 19973

711 N. DuPont Boulevard, Milford, DE 19963

4460 Corporation Lane, Virginia Beach, VA 23462

129 S. Juliana Street, Bedford, PA 15522

110 W. Main Street, Everett, PA 15537

131 N. Centre Street, Cumberland, MD 21502

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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.
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default
Coldwell Banker Premier

CB Premier

+1(540) 269-5683 cbpadmin@premiermove.com

1682 S Pleasant Valley Rd, Winchester, VA, 22601, United States

    • Home
      Sell
      1. Sell My Home
      2. Home Valuation
      Commercial
      Market Snapshot
      About
      1. Meet Our Team
      2. Delaware Offices
      3. Virginia Offices
      4. West Virginia Offices
      5. Maryland Offices
      6. About Us
      7. Contact Us
    • Careers
      1. Careers
      2. How to Get Your Real Estate License
      Rentals
      Property Management
      1. VA, WV, MD, PA Property Management
      2. Delaware Rentals & Leasing
      Move Meter
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    • Buy
      1. Why Buy From Us?
      2. All Listings
      3. Featured Listings
      4. Sold Listings
      Vacation Rentals
      1. DE Vacation Rentals
      2. LIST YOUR RENTAL PROPERTY
      3. SEASONAL RENTALS
      4. WINTER RENTALS
      5. YEAR ROUND RENTALS
      Neighborhoods
      1. Basye
      2. Ashburn
      3. Shepherdstown
      4. Martinsburg
      5. Berkeley Springs
      6. Falling Waters
      7. Stephens City
      8. Edinburg
      9. Harrisonburg
      10. Strasburg
      11. Mount Jackson
      12. Staunton
      13. Front Royal
      14. New Market
      15. Harrisonburg
      16. Charlottesville
      17. Winchester
      18. Waynesboro
      19. Stephenson
      20. Harpers Ferry
      Our Blog

Get My App

Steve DuBrueler, Broker

16 Offices Serving VA, WV, DC, MD, DE, PA, and NC

1682 S. Pleasant Valley Road, Winchester, VA 22601 

14 E. Piccadilly Street, Winchester, VA 22601

115 Aikens Center, Suite 21, Martinsburg, WV 25404 

415 South Street Suite C, Front Royal, VA 22630 

116 East German Street, Shepherdstown, WV 25443

1618 Orkney Grade, Suite A, Basye, VA 22810

200 S. Washington Street, Berkeley Springs, WV 25411

1950 Evelyn Byrd Avenue, Suite A, Harrisonburg, VA 22801

20184 Coastal Highway, Rehoboth Beach, DE 19971

800 Kings Highway, Lewes, DE 19958

22350 Sussex Highway, Seaford, DE 19973

711 N. DuPont Boulevard, Milford, DE 19963

4460 Corporation Lane, Virginia Beach, VA 23462

129 S. Juliana Street, Bedford, PA 15522

110 W. Main Street, Everett, PA 15537

131 N. Centre Street, Cumberland, MD 21502

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.