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23 Properties

23 Properties Available In Chestertown

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MD >Chestertown >
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21082 WYOMING AVE, Chestertown, MD 21620
1/63 63

$1,550,000

Open Sat 11AM-2PM

Single Family Home

3 Beds 4 Baths 2,699 SqFt

21082 WYOMING AVE, Chestertown, MD 21620

Charming Chesapeake Bay Home with Stunning Water Views and Incredible Sunsets! Living space is 2699 and the unfinished...

MLS# MDKE2005016

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
811 S MEADOWVIEW DR, Chestertown, MD 21620
3D

$459,000

Pending

Single Family Home

3 Beds 2 Baths 2,064 SqFt

811 S MEADOWVIEW DR, Chestertown, MD 21620

Charming and Immaculately Maintained One-Level Home<br><br>Step onto the inviting front porch of this meticulously cared...

MLS# MDKE2005086

Listed by Redfin Corp

Bright MLS (BMLS)
7961 QUAKER NECK RD, Chestertown, MD 21620
1/95 95

$1,495,000

Pending

Single Family Home

5 Beds 4 Baths 4,167 SqFt

7961 QUAKER NECK RD, Chestertown, MD 21620

Highest and Best Offers due by 7pm on Friday, 5/9. Open House - Cancelled.<br><br>**Exquisite Waterfront Retreat on Ches...

MLS# MDKE2005090

Listed by Compass

Bright MLS (BMLS)
9050 POINT LN, Chestertown, MD 21620
1/71 71

$745,000

Under Contract

Single Family Home

4 Beds 3 Baths 3,166 SqFt

9050 POINT LN, Chestertown, MD 21620

Welcome to this beautifully maintained 4-bedroom, 3-bath home offering serene views of the Chesapeake Bay in the quiet a...

MLS# MDKE2005102

Listed by Coldwell Banker Chesapeake Real Estate Company

Bright MLS (BMLS)
7988 ALDAN DR, Chestertown, MD 21620
1/56 56

$749,900

Under Contract

Single Family Home

5 Beds 3 Baths 3,394 SqFt

7988 ALDAN DR, Chestertown, MD 21620

This is a stunning property! It combines elegance and functionality with its spacious layout, beautiful finishes, and th...

MLS# MDKE2004966

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
5179 QUAKER NECK RD, Chestertown, MD 21620
1/48 48

$579,900

Active

Single Family Home

1 Bath 1,148 SqFt

5179 QUAKER NECK RD, Chestertown, MD 21620

BACK ON THE MARKET due to financing. <br>A One-of-a-Kind Historic Treasure Reimagined for Modern Living<br>Step into his...

MLS# MDKE2005028

Listed by Hyatt & Company Real Estate, LLC

Bright MLS (BMLS)
22153 1ST POINT RD, Chestertown, MD 21620
1/87 87

$1,200,000

Under Contract

Single Family Home

5 Beds 6 Baths 3,078 SqFt

22153 1ST POINT RD, Chestertown, MD 21620

Experience the waterfront lifestyle like never before in this stunning mid-century modern home, which seamlessly hangs c...

MLS# MDKE2004460

Listed by TTR Sotheby's International Realty

Bright MLS (BMLS)
216 SILVER HEEL RD, Chestertown, MD 21620
1/32 32

$364,900

Under Contract

Single Family Home

3 Beds 3 Baths 1,724 SqFt

216 SILVER HEEL RD, Chestertown, MD 21620

Welcome to this move-in ready home, situated on a premium corner lot in The Village at Chestertown! This charming 1,742 ...

MLS# MDKE2005024

Listed by CENTURY 21 New Millennium

Bright MLS (BMLS)
7483 SHORTALL ST, Chestertown, MD 21620
1/37 37

$285,000

Under Contract

Single Family Home

3 Beds 2 Baths 1,232 SqFt

7483 SHORTALL ST, Chestertown, MD 21620

Discover this delightful, move-in-ready ranch-style home in a peaceful Chestertown setting. Featuring three bedrooms and...

MLS# MDKE2004948

Listed by RE/MAX Executive

Bright MLS (BMLS)
128 EDMORE RD, Chestertown, MD 21620
1/57 57

$425,000

Price Dropped by $15K

Single Family Home

4 Beds 2 Baths 2,568 SqFt

128 EDMORE RD, Chestertown, MD 21620

Your Dream Eastern Shore Retreat Awaits!<br><br>Welcome to this meticulously maintained home, where charm and comfort bl...

MLS# MDQA2012546

Listed by Berkshire Hathaway HomeServices PenFed Realty

Bright MLS (BMLS)
306 CEDAR ST, Chestertown, MD 21620
1/42 42

$319,000

Under Contract

Single Family Home

4 Beds 2 Baths 1,404 SqFt

306 CEDAR ST, Chestertown, MD 21620

Lovely 4 bedroom, 2 bath Cape Cod located in College Heights. The house has been freshly painted inside and out and has...

MLS# MDKE2004954

Listed by Doug Ashley Realtors, LLC

Bright MLS (BMLS)
314 DEVON DR, Chestertown, MD 21620
1/45 45

$499,900

Price Dropped by $14K

Single Family Home

4 Beds 4 Baths 3,420 SqFt

314 DEVON DR, Chestertown, MD 21620

Welcome to 314 Devon Drive in Chestertown—a beautifully designed 4-bedroom, 3.5-bath home where comfort meets style in e...

MLS# MDKE2004946

Listed by The Parker Group

Bright MLS (BMLS)
110 FLYING CLOUD COURT, Chestertown, MD 21620
1/17 17

$349,900

Active

Single Family Home

3 Beds 3 Baths 1,856 SqFt

110 FLYING CLOUD COURT, Chestertown, MD 21620

SINGLE FAMILY HOME built just 2 years ago! Clean lines and neutral tones make this an easy move-in with nothing to do! ...

MLS# MDKE2004850

Listed by Berkshire Hathaway HomeServices Homesale Realty

Bright MLS (BMLS)
109 WILTON RD, Chestertown, MD 21620
1/30 30

$349,900

Active

Single Family Home

3 Beds 2 Baths 1,392 SqFt

109 WILTON RD, Chestertown, MD 21620

Welcome to this charming 3-bedroom, 2-bathroom rancher, offering the perfect blend of comfort and convenience with one-l...

MLS# MDQA2011782

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
23393 CACAWAY FARM LN, Chestertown, MD 21620
1/44 44

$1,450,000

Active

Condo

3 Beds 4 Baths 4,446 SqFt

23393 CACAWAY FARM LN, Chestertown, MD 21620

**Exclusive Waterfront Craftsman Home with Sandy Beach – A Rare Opportunity**<br>Nestled on the serene East Fork of Lang...

MLS# MDKE2004002

Listed by Gunther-McClary Real Estate

Bright MLS (BMLS)
136 TRUSLOW FARM LN, Chestertown, MD 21620
1/12 12

$575,000

New

Vacant Land

3.01 Acres

136 TRUSLOW FARM LN, Chestertown, MD 21620

Don't miss this rare opportunity to own one of the only waterfront lots still available on the Chester River! Perfectly ...

MLS# MDQA2013478

Listed by Chesapeake Real Estate Associates, LLC

Bright MLS (BMLS)
870 HIGH ST, Chestertown, MD 21620
1/72 72

$1,870,000

Active

Commercial

16,977 SqFt

870 HIGH ST, Chestertown, MD 21620

Radcliffe Mill presents an exceptional opportunity for a savvy investor looking for value and a one-of-a-kind investment...

MLS# MDKE2004140

Listed by Taylor Properties

Bright MLS (BMLS)
860 HIGH ST, Chestertown, MD 21620
1/38 38

$860,000

Active

Commercial

3,114 SqFt

860 HIGH ST, Chestertown, MD 21620

The Annex/Seed House at Radcliffe Mill is a stunning, one of a kind space. Fully restored in 2007, with additional work...

MLS# MDKE2004138

Listed by Taylor Properties

Bright MLS (BMLS)
860 & 870 HIGH ST, Chestertown, MD 21620
1/92 92

$2,400,000

Price Dropped by $300K

Commercial

16,977 SqFt

860 & 870 HIGH ST, Chestertown, MD 21620

Now be offered with a price improvement, Radcliffe Mill presents an exceptional opportunity for a savvy investor looking...

MLS# MDKE2003850

Listed by Taylor Properties

Bright MLS (BMLS)
870 HIGH ST #INDIVIDUAL OFFICES, Chestertown, MD 21620
1/30 30

$425

Active

Commercial

16,977 SqFt

870 HIGH ST #INDIVIDUAL OFFICES, Chestertown, MD 21620

Individual office for rents, ranging from private office suites, private offices to cubicles. All utilities, including...

MLS# MDKE2004432

Listed by Taylor Properties

Bright MLS (BMLS)
870 HIGH ST #2-3, Chestertown, MD 21620
1/55 55

$18

Active

Commercial

16,977 SqFt

870 HIGH ST #2-3, Chestertown, MD 21620

Three floors of premium office space are available for lease at Radcliffe Mill. This listing encompasses the top three f...

MLS# MDKE2003776

Listed by Taylor Properties

Bright MLS (BMLS)
870 HIGH ST #2, Chestertown, MD 21620
1/35 35

$18

Active

Commercial

16,977 SqFt

870 HIGH ST #2, Chestertown, MD 21620

Strategically positioned at the head of the Rail Trail leading to downtown Chestertown and Washington College, and on th...

MLS# MDKE2003772

Listed by Taylor Properties

Bright MLS (BMLS)
870 HIGH ST #3, Chestertown, MD 21620
1/36 36

$18

Active

Commercial

16,977 SqFt

870 HIGH ST #3, Chestertown, MD 21620

Strategically positioned at the head of the Rail Trail leading to downtown Chestertown and Washington College, and on th...

MLS# MDKE2003766

Listed by Taylor Properties

Bright MLS (BMLS)
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eXp Realty LLC

Laurie Dau License ID: RS315078

+1(215) 782-6087 laurie@lauriedauteam.com

77 N Broad Street , Doylestown, Pennsylvania 18901 USA

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LDRET + eXp Logo - White on Black png
eXp Realty LLC

Laurie Dau License ID: RS315078

+1(215) 782-6087 laurie@lauriedauteam.com

77 N Broad Street , Doylestown, Pennsylvania 18901 USA

    • Home
      About
      1. My Team
      2. About Us
      3. Contact Us
      4. 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.