Country Homes for Sale in Chester, MD

33 Homes for Sale

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3D Tour

Photo 3 of Single family home for sale at 162 Kirwans Landing Ln, Chester, MD 21619 | MLS# MDQA2018812 | Listing updated on 2026-10-10

Photo 1 of Single family home for sale at 162 Kirwans Landing Ln, Chester, MD 21619 | MLS# MDQA2018812 | Listing updated on 2026-10-10

Photo 2 of Single family home for sale at 162 Kirwans Landing Ln, Chester, MD 21619 | MLS# MDQA2018812 | Listing updated on 2026-10-10

$1,199,900

5Bds

3Ba

3,000sqft

Single family home for sale

162 Kirwans Landing Ln, CHESTER, MD 21619

Next Step Realty

Hot

Photo 3 of Single family home for sale at 113 Bentons Pleasure Rd, Chester, MD 21619 | MLS# MDQA2018142 | Listing updated on 2026-10-10

Photo 1 of Single family home for sale at 113 Bentons Pleasure Rd, Chester, MD 21619 | MLS# MDQA2018142 | Listing updated on 2026-10-10

Photo 2 of Single family home for sale at 113 Bentons Pleasure Rd, Chester, MD 21619 | MLS# MDQA2018142 | Listing updated on 2026-10-10

$829,000

4Bds

3Ba

3,168sqft

Single family home for sale

113 Bentons Pleasure Rd, CHESTER, MD 21619

Cummings & Co. Realtors

Price Drop: $215K

Photo 3 of Single family home for sale at 300 Woods Point Rd, Chester, MD 21619 | MLS# MDQA2017820 | Listing updated on 2026-10-09

Photo 1 of Single family home for sale at 300 Woods Point Rd, Chester, MD 21619 | MLS# MDQA2017820 | Listing updated on 2026-10-09

Photo 2 of Single family home for sale at 300 Woods Point Rd, Chester, MD 21619 | MLS# MDQA2017820 | Listing updated on 2026-10-09

$2,625,000

3Bds

2Ba

2,000sqft

Single family home for sale

300 Woods Point Rd, CHESTER, MD 21619

Tidewater Properties

Photo 3 of Condo for sale at 208 Widgeon Way, Chester, MD 21619 | MLS# MDQA2018920 | Listing updated on 2026-10-09

Photo 1 of Condo for sale at 208 Widgeon Way, Chester, MD 21619 | MLS# MDQA2018920 | Listing updated on 2026-10-09

Photo 2 of Condo for sale at 208 Widgeon Way, Chester, MD 21619 | MLS# MDQA2018920 | Listing updated on 2026-10-09

$599,900

3Bds

4Ba

2,100sqft

Condo for sale

208 Widgeon Way, CHESTER, MD 21619

Re/Max Leading Edge

Photo 3 of Condo for sale at 1010 Auckland Way, Chester, MD 21619 | MLS# MDQA2018726 | Listing updated on 2026-10-08

Photo 1 of Condo for sale at 1010 Auckland Way, Chester, MD 21619 | MLS# MDQA2018726 | Listing updated on 2026-10-08

Photo 2 of Condo for sale at 1010 Auckland Way, Chester, MD 21619 | MLS# MDQA2018726 | Listing updated on 2026-10-08

$595,000

3Bds

4Ba

2,100sqft

Condo for sale

1010 Auckland Way, CHESTER, MD 21619

Berkshire Hathaway Homeservices Homesale Realty

3D Tour

Photo 3 of Single family home for sale at 223 Evelyne St, Chester, MD 21619 | MLS# MDQA2018948 | Listing updated on 2026-10-08

Photo 1 of Single family home for sale at 223 Evelyne St, Chester, MD 21619 | MLS# MDQA2018948 | Listing updated on 2026-10-08

Photo 2 of Single family home for sale at 223 Evelyne St, Chester, MD 21619 | MLS# MDQA2018948 | Listing updated on 2026-10-08

$799,000

3Bds

3Ba

2,575sqft

Single family home for sale

223 Evelyne St, CHESTER, MD 21619

Samson Properties

Photo 3 of Single family home for sale at 205 Anchor Ln, Chester, MD 21619 | MLS# MDQA2017856 | Listing updated on 2026-10-07

Photo 1 of Single family home for sale at 205 Anchor Ln, Chester, MD 21619 | MLS# MDQA2017856 | Listing updated on 2026-10-07

Photo 2 of Single family home for sale at 205 Anchor Ln, Chester, MD 21619 | MLS# MDQA2017856 | Listing updated on 2026-10-07

$500,000

4Bds

3Ba

3,000sqft

Single family home for sale

205 Anchor Ln, CHESTER, MD 21619

Samson Properties

Price Drop: $39.9K

Photo 3 of Condo for sale at 5011 Bridgepointe Dr, Chester, MD 21619 | MLS# MDQA2017274 | Listing updated on 2026-10-07

Photo 1 of Condo for sale at 5011 Bridgepointe Dr, Chester, MD 21619 | MLS# MDQA2017274 | Listing updated on 2026-10-07

Photo 2 of Condo for sale at 5011 Bridgepointe Dr, Chester, MD 21619 | MLS# MDQA2017274 | Listing updated on 2026-10-07

$315,000

3Bds

3Ba

1,302sqft

Condo for sale

5011 Bridgepointe Dr, CHESTER, MD 21619

Keller Williams Realty Centre

3D Tour

Photo 3 of Townhouse for sale at 512 Auckland Way, Chester, MD 21619 | MLS# MDQA2018750 | Listing updated on 2026-10-03

Photo 1 of Townhouse for sale at 512 Auckland Way, Chester, MD 21619 | MLS# MDQA2018750 | Listing updated on 2026-10-03

Photo 2 of Townhouse for sale at 512 Auckland Way, Chester, MD 21619 | MLS# MDQA2018750 | Listing updated on 2026-10-03

$375,000

3Bds

4Ba

1,899sqft

Townhouse for sale

512 Auckland Way, CHESTER, MD 21619

Long & Foster Real Estate, Inc.

Price Drop: $7.5K

Photo 3 of Sale Pending at 114 Merganser Ct, Chester, MD 21619 | MLS# MDQA2016968 | Listing updated on 2026-10-01

Photo 1 of Sale Pending at 114 Merganser Ct, Chester, MD 21619 | MLS# MDQA2016968 | Listing updated on 2026-10-01

Photo 2 of Sale Pending at 114 Merganser Ct, Chester, MD 21619 | MLS# MDQA2016968 | Listing updated on 2026-10-01

$287,500

2Bds

2Ba

1,069sqft

Sale Pending

114 Merganser Ct, CHESTER, MD 21619

Benson & Mangold, Llc

Photo 3 of Condo for sale at 510 Auckland Way, Chester, MD 21619 | MLS# MDQA2018734 | Listing updated on 2026-09-29

Photo 1 of Condo for sale at 510 Auckland Way, Chester, MD 21619 | MLS# MDQA2018734 | Listing updated on 2026-09-29

Photo 2 of Condo for sale at 510 Auckland Way, Chester, MD 21619 | MLS# MDQA2018734 | Listing updated on 2026-09-29

$410,000

3Bds

3Ba

1,899sqft

Condo for sale

510 Auckland Way, CHESTER, MD 21619

Engel & Volkers Annapolis

Price Drop: $25.1K

Photo 3 of Sale Pending at 313 Thomas White Blvd, Chester, MD 21619 | MLS# MDQA2018144 | Listing updated on 2026-09-28

Photo 1 of Sale Pending at 313 Thomas White Blvd, Chester, MD 21619 | MLS# MDQA2018144 | Listing updated on 2026-09-28

Photo 2 of Sale Pending at 313 Thomas White Blvd, Chester, MD 21619 | MLS# MDQA2018144 | Listing updated on 2026-09-28

$799,900

4Bds

3Ba

3,291sqft

Sale Pending

313 Thomas White Blvd, CHESTER, MD 21619

Monument Sotheby'S International Realty

Hot

Photo 3 of Single family home for sale at 228 Bayberry Dr, Chester, MD 21619 | MLS# MDQA2018728 | Listing updated on 2026-10-06

Photo 1 of Single family home for sale at 228 Bayberry Dr, Chester, MD 21619 | MLS# MDQA2018728 | Listing updated on 2026-10-06

Photo 2 of Single family home for sale at 228 Bayberry Dr, Chester, MD 21619 | MLS# MDQA2018728 | Listing updated on 2026-10-06

$665,000

2Bds

3Ba

1,993sqft

Single family home for sale

228 Bayberry Dr, CHESTER, MD 21619

Long & Foster Real Estate, Inc.

Photo 3 of Single family home for sale at 402 Macum Crk Dr, Chester, MD 21619 | MLS# MDQA2018418 | Listing updated on 2026-10-07

Photo 1 of Single family home for sale at 402 Macum Crk Dr, Chester, MD 21619 | MLS# MDQA2018418 | Listing updated on 2026-10-07

Photo 2 of Single family home for sale at 402 Macum Crk Dr, Chester, MD 21619 | MLS# MDQA2018418 | Listing updated on 2026-10-07

$789,000

3Bds

3Ba

2,787sqft

Single family home for sale

402 Macum Crk Dr, CHESTER, MD 21619

Samson Properties

Photo 3 of Single family home for sale at 200 Church St, Chester, MD 21619 | MLS# MDQA2018584 | Listing updated on 2026-09-16

Photo 1 of Single family home for sale at 200 Church St, Chester, MD 21619 | MLS# MDQA2018584 | Listing updated on 2026-09-16

Photo 2 of Single family home for sale at 200 Church St, Chester, MD 21619 | MLS# MDQA2018584 | Listing updated on 2026-09-16

$350,000

2Bds

2Ba

1,274sqft

Single family home for sale

200 Church St, CHESTER, MD 21619

Re/Max Executive

3D Tour

Photo 3 of Single family home for sale at 233 Cross Creek Ct, Chester, MD 21619 | MLS# MDQA2018296 | Listing updated on 2026-09-14

Photo 1 of Single family home for sale at 233 Cross Creek Ct, Chester, MD 21619 | MLS# MDQA2018296 | Listing updated on 2026-09-14

Photo 2 of Single family home for sale at 233 Cross Creek Ct, Chester, MD 21619 | MLS# MDQA2018296 | Listing updated on 2026-09-14

$569,900

4Bds

3Ba

2,332sqft

Single family home for sale

233 Cross Creek Ct, CHESTER, MD 21619

Rory S. Coakley Realty, Inc.

3D Tour

Photo 3 of Single family home for sale at 1717 Harbor Dr, Chester, MD 21619 | MLS# MDQA2018534 | Listing updated on 2026-09-21

Photo 1 of Single family home for sale at 1717 Harbor Dr, Chester, MD 21619 | MLS# MDQA2018534 | Listing updated on 2026-09-21

Photo 2 of Single family home for sale at 1717 Harbor Dr, Chester, MD 21619 | MLS# MDQA2018534 | Listing updated on 2026-09-21

$1,250,000

3Bds

3Ba

2,742sqft

Single family home for sale

1717 Harbor Dr, CHESTER, MD 21619

Chesapeake Real Estate Associates, Llc

Photo 3 of Single family home for sale at 148 Elinor St, Chester, MD 21619 | MLS# MDQA2018244 | Listing updated on 2026-08-26

Photo 1 of Single family home for sale at 148 Elinor St, Chester, MD 21619 | MLS# MDQA2018244 | Listing updated on 2026-08-26

Photo 2 of Single family home for sale at 148 Elinor St, Chester, MD 21619 | MLS# MDQA2018244 | Listing updated on 2026-08-26

$899,000

3Bds

3Ba

2,464sqft

Single family home for sale

148 Elinor St, CHESTER, MD 21619

Samson Properties

Photo 3 of Sale Pending at 193 Spinnaker Wy, Chester, MD 21619 | MLS# MDQA2018122 | Listing updated on 2026-08-10

Photo 1 of Sale Pending at 193 Spinnaker Wy, Chester, MD 21619 | MLS# MDQA2018122 | Listing updated on 2026-08-10

Photo 2 of Sale Pending at 193 Spinnaker Wy, Chester, MD 21619 | MLS# MDQA2018122 | Listing updated on 2026-08-10

$856,000

3Bds

3Ba

2,527sqft

Sale Pending

193 Spinnaker Wy, CHESTER, MD 21619

Long & Foster Real Estate, Inc.

Photo 3 of Single family home for sale at 124 Riverside Dr, Chester, MD 21619 | MLS# MDQA2017718 | Listing updated on 2026-07-26

Photo 1 of Single family home for sale at 124 Riverside Dr, Chester, MD 21619 | MLS# MDQA2017718 | Listing updated on 2026-07-26

Photo 2 of Single family home for sale at 124 Riverside Dr, Chester, MD 21619 | MLS# MDQA2017718 | Listing updated on 2026-07-26

$499,000

4Bds

3Ba

1,979sqft

Single family home for sale

124 Riverside Dr, CHESTER, MD 21619

Douglas Realty Llc

3D Tour

Photo 3 of Condo for sale at 29 Queen Mary Ct, Chester, MD 21619 | MLS# MDQA2017974 | Listing updated on 2026-07-18

Photo 1 of Condo for sale at 29 Queen Mary Ct, Chester, MD 21619 | MLS# MDQA2017974 | Listing updated on 2026-07-18

Photo 2 of Condo for sale at 29 Queen Mary Ct, Chester, MD 21619 | MLS# MDQA2017974 | Listing updated on 2026-07-18

$359,000

3Bds

3Ba

1,440sqft

Condo for sale

29 Queen Mary Ct, CHESTER, MD 21619

Rosendale Realty

3D Tour

Photo 3 of Single family home for sale at 108 Carriage Heath, Chester, MD 21619 | MLS# MDQA2017422 | Listing updated on 2026-07-07

Photo 1 of Single family home for sale at 108 Carriage Heath, Chester, MD 21619 | MLS# MDQA2017422 | Listing updated on 2026-07-07

Photo 2 of Single family home for sale at 108 Carriage Heath, Chester, MD 21619 | MLS# MDQA2017422 | Listing updated on 2026-07-07

$1,199,000

5Bds

4Ba

4,334sqft

Single family home for sale

108 Carriage Heath, CHESTER, MD 21619

Coldwell Banker Realty

3D Tour

Photo 3 of Single family home for sale at 200 Newtown Rd, Chester, MD 21619 | MLS# MDQA2016754 | Listing updated on 2026-06-27

Photo 1 of Single family home for sale at 200 Newtown Rd, Chester, MD 21619 | MLS# MDQA2016754 | Listing updated on 2026-06-27

Photo 2 of Single family home for sale at 200 Newtown Rd, Chester, MD 21619 | MLS# MDQA2016754 | Listing updated on 2026-06-27

$420,000

3Bds

3Ba

1,296sqft

Single family home for sale

200 Newtown Rd, CHESTER, MD 21619

Samson Properties

3D Tour

Photo 3 of Single family home for sale at 132 Kestrel Ln, Chester, MD 21619 | MLS# MDQA2015732 | Listing updated on 2026-06-11

Photo 1 of Single family home for sale at 132 Kestrel Ln, Chester, MD 21619 | MLS# MDQA2015732 | Listing updated on 2026-06-11

Photo 2 of Single family home for sale at 132 Kestrel Ln, Chester, MD 21619 | MLS# MDQA2015732 | Listing updated on 2026-06-11

$945,000

4Bds

4Ba

3,634sqft

Single family home for sale

132 Kestrel Ln, CHESTER, MD 21619

Ttr Sotheby'S International Realty

Photo 3 of Single family home for sale at 126 Claiborne St, Chester, MD 21619 | MLS# MDQA2017106 | Listing updated on 2026-06-02

Photo 1 of Single family home for sale at 126 Claiborne St, Chester, MD 21619 | MLS# MDQA2017106 | Listing updated on 2026-06-02

Photo 2 of Single family home for sale at 126 Claiborne St, Chester, MD 21619 | MLS# MDQA2017106 | Listing updated on 2026-06-02

$775,000

3Bds

3Ba

2,276sqft

Single family home for sale

126 Claiborne St, CHESTER, MD 21619

Samson Properties

3D Tour

Photo 3 of Sale Pending at 1363 Calvert Rd, Chester, MD 21619 | MLS# MDQA2015954 | Listing updated on 2026-04-14

Photo 1 of Sale Pending at 1363 Calvert Rd, Chester, MD 21619 | MLS# MDQA2015954 | Listing updated on 2026-04-14

Photo 2 of Sale Pending at 1363 Calvert Rd, Chester, MD 21619 | MLS# MDQA2015954 | Listing updated on 2026-04-14

$501,200

3Bds

2Ba

1,400sqft

Sale Pending

1363 Calvert Rd, CHESTER, MD 21619

Revol Real Estate, Llc

Photo 3 of Single family home for sale at 102 Carriage Heath, Chester, MD 21619 | MLS# MDQA2016726 | Listing updated on 2026-04-08

Photo 1 of Single family home for sale at 102 Carriage Heath, Chester, MD 21619 | MLS# MDQA2016726 | Listing updated on 2026-04-08

Photo 2 of Single family home for sale at 102 Carriage Heath, Chester, MD 21619 | MLS# MDQA2016726 | Listing updated on 2026-04-08

$950,000

4Bds

4Ba

2,940sqft

Single family home for sale

102 Carriage Heath, CHESTER, MD 21619

Wilson Realty & Staging Llc

Photo 3 of Single family home for sale at 2613 Cecil Dr, Chester, MD 21619 | MLS# MDQA2016320 | Listing updated on 2026-04-07

Photo 1 of Single family home for sale at 2613 Cecil Dr, Chester, MD 21619 | MLS# MDQA2016320 | Listing updated on 2026-04-07

Photo 2 of Single family home for sale at 2613 Cecil Dr, Chester, MD 21619 | MLS# MDQA2016320 | Listing updated on 2026-04-07

$949,900

5Bds

4Ba

2,496sqft

Single family home for sale

2613 Cecil Dr, CHESTER, MD 21619

Benson & Mangold, Llc

Photo 3 of Sale Pending at 1401 Calvert Rd, Chester, MD 21619 | MLS# MDQA2014504 | Listing updated on 2026-03-22

Photo 1 of Sale Pending at 1401 Calvert Rd, Chester, MD 21619 | MLS# MDQA2014504 | Listing updated on 2026-03-22

Photo 2 of Sale Pending at 1401 Calvert Rd, Chester, MD 21619 | MLS# MDQA2014504 | Listing updated on 2026-03-22

$454,900

2Bds

2Ba

1,444sqft

Sale Pending

1401 Calvert Rd, CHESTER, MD 21619

Coldwell Banker Waterman Realty

Photo 3 of Condo for sale at 204 Ringneck Ct, Chester, MD 21619 | MLS# MDQA2015908 | Listing updated on 2026-03-19

Photo 1 of Condo for sale at 204 Ringneck Ct, Chester, MD 21619 | MLS# MDQA2015908 | Listing updated on 2026-03-19

Photo 2 of Condo for sale at 204 Ringneck Ct, Chester, MD 21619 | MLS# MDQA2015908 | Listing updated on 2026-03-19

$324,900

--Bds

--Ba

1,747sqft

Condo for sale

204 Ringneck Ct, CHESTER, MD 21619

Cummings & Co. Realtors

3D Tour

Photo 3 of Sale Pending at 1870 Harbor Dr, Chester, MD 21619 | MLS# MDQA2015064 | Listing updated on 2026-03-17

Photo 1 of Sale Pending at 1870 Harbor Dr, Chester, MD 21619 | MLS# MDQA2015064 | Listing updated on 2026-03-17

Photo 2 of Sale Pending at 1870 Harbor Dr, Chester, MD 21619 | MLS# MDQA2015064 | Listing updated on 2026-03-17

$320,000

2Bds

1Ba

832sqft

Sale Pending

1870 Harbor Dr, CHESTER, MD 21619

Re/Max Executive

3D Tour

Photo 3 of Sale Pending at 49 Queen Guinevere Way, Chester, MD 21619 | MLS# MDQA2013390 | Listing updated on 2026-03-15

Photo 1 of Sale Pending at 49 Queen Guinevere Way, Chester, MD 21619 | MLS# MDQA2013390 | Listing updated on 2026-03-15

Photo 2 of Sale Pending at 49 Queen Guinevere Way, Chester, MD 21619 | MLS# MDQA2013390 | Listing updated on 2026-03-15

$519,499

2Bds

3Ba

1,600sqft

Sale Pending

49 Queen Guinevere Way, CHESTER, MD 21619

Realty Navigator

3D Tour

Photo 3 of Condo for sale at 402 Blenny Ln, Chester, MD 21619 | MLS# MDQA2015934 | Listing updated on 2026-03-14

Photo 1 of Condo for sale at 402 Blenny Ln, Chester, MD 21619 | MLS# MDQA2015934 | Listing updated on 2026-03-14

Photo 2 of Condo for sale at 402 Blenny Ln, Chester, MD 21619 | MLS# MDQA2015934 | Listing updated on 2026-03-14

$399,000

3Bds

4Ba

1,747sqft

Condo for sale

402 Blenny Ln, CHESTER, MD 21619

Long & Foster Real Estate, Inc.

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Chester, MD Housing Market Overview

Chester is a balanced market, giving buyers and sellers room to negotiate. With 3.1 months of supply and homes averaging 116 days on the market, you can make decisions without the pressure of a highly competitive market.

Status

Balanced Market

Days on Market

116

Inventory

Sep 2021Mar 2024Mar 2026

Median Home Price

$446,000 0.16%

In Mar 2026 · YoY

Sep 2021Mar 2024Mar 2026

Mortgage Rates 30-Yr Fixed

6.23% 0.58%

Current rate · YoY

Loan Type

30-Year Fixed

Housing Supply

Homes For Sale: 43 Down 0.00%
Newly Listed Homes: 26 Up 0.24%
Months of Supply: 3.1 Down 0.00%

Housing Demand

Homes Sold: 14 Down 0.00%
Sale-to-List Ratio: 98.8% Up 1.10%
Homes Sold Above List: 21.4% Up 7.14%

30-yr fixed rate 6.23% · Data as of Mar 2026 · Source: Houzeo Research.

View Full Chester Market Report

No. of Homes

Homes for Sale in Chester With AC

147

Houses for Sale in Chester With Pool

103

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1 Bedroom Homes for Sale in Chester, MD

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Based on information from Bright MLS through Oct 11, 2026, 6:00 AM. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. © 2026 Bright MLS, Inc. All Rights Reserved. Click here for more information