Movoto Real Estate

Chester Real Estate & Chester, MD Homes For Sale | Page 2

138 Homes
 
202 Claiborne St, Chester, MD 21619
  • $915,000
  • 4Bd
  • 4Ba
  • 3,424 Sq Ft
223 Evelyne St, Chester, MD 21619
  • $799,000
  • 3Bd
  • 3Ba
  • 2,575 Sq Ft
2011 Stevens Dr, Chester, MD 21619
  • $489,900
  • 3Bd
  • 2Ba
  • 1,663 Sq Ft
830 Warbler Way #2824, Chester, MD 21619
  • $749,990
  • 3Bd
  • 3Ba
  • 2,602 Sq Ft
1351 Calvert Rd, Chester, MD 21619
  • $645,000
  • 6Bd
  • 3Ba
  • 2,700 Sq Ft
402 Macum Creek Dr, Chester, MD 21619
  • $789,000
  • 3Bd
  • 3Ba
  • 2,787 Sq Ft
200 Church St, Chester, MD 21619
  • $350,000
  • 2Bd
  • 2Ba
  • 1,274 Sq Ft
641 Warbler Way, Chester, MD 21619
  • $599,990
  • 2Bd
  • 2Ba
  • 1,690 Sq Ft
275 Warbler Way, Chester, MD 21619
  • $930,000
  • 3Bd
  • 3Ba
  • 2,761 Sq Ft
736 Warbler Way #2733, Chester, MD 21619
  • $719,990
  • 2Bd
  • 3Ba
  • 1,900 Sq Ft
315 Bentons Pleasure Rd, Chester, MD 21619
  • $599,900
  • 3Bd
  • 2Ba
  • 1,688 Sq Ft
$30K
102 Boatswain Way #2932, Chester, MD 21619
  • $809,990
  • 2Bd
  • 3Ba
  • 1,900 Sq Ft
$10K
134 Richard Ingle Way, Chester, MD 21619
  • $739,000
  • 4Bd
  • 4Ba
  • 2,185 Sq Ft
$10K
230 Switchgrass Way #12, Chester, MD 21619
  • $499,000
  • 2Bd
  • 3Ba
  • 2,003 Sq Ft
$10.9K
300 Woods Point Rd, Chester, MD 21619
  • $2,625,000
  • 3Bd
  • 2Ba
  • 2,000 Sq Ft
$215K
102 Boatswain Way #2933, Chester, MD 21619
  • $809,990
  • 2Bd
  • 3Ba
  • 1,900 Sq Ft
$10K
830 Warbler Way UNIT 43, Chester, MD 21619
  • $789,990
  • 2Bd
  • 3Ba
  • 1,900 Sq Ft
$29.8K
830 Warbler Way UNIT 33, Chester, MD 21619
  • $689,990
  • 2Bd
  • 3Ba
  • 1,900 Sq Ft
$28.4K
1000 Herons Nest Way #43, Chester, MD 21619
  • $595,000
  • 2Bd
  • 3Ba
  • 1,832 Sq Ft
Open SUN 1-3
807 Auckland Way, Chester, MD 21619
  • $425,500
  • 3Bd
  • 4Ba
  • 2,100 Sq Ft
232 Evelyne St, Chester, MD 21619
  • $825,000
  • 4Bd
  • 4Ba
  • 3,312 Sq Ft
$15K
106 Bodys Neck Rd, Chester, MD 21619
  • $429,900
  • 3Bd
  • 3Ba
  • 1,595 Sq Ft
$5.1K
102 Boatswain Way UNIT 43, Chester, MD 21619
  • $909,990
  • 2Bd
  • 3Ba
  • 1,900 Sq Ft
$10K
5011 Bridgepointe Dr, Chester, MD 21619
  • $315,000
  • 3Bd
  • 3Ba
  • 1,302 Sq Ft
$39.9K
54 D Queen Caroline Ct, Chester, MD 21619
  • $299,900
  • 3Bd
  • 3Ba
  • 1,440 Sq Ft
$10K
45 G Queen Neva Ct, Chester, MD 21619
  • $318,500
  • 2Bd
  • 3Ba
  • 1,312 Sq Ft
$31K
54 Queen Caroline Ct # F, Chester, MD 21619
  • $349,900
  • 3Bd
  • 3Ba
  • 1,440 Sq Ft
$10K
2855 Cox Neck Rd, Chester, MD 21619
  • $1,125,000
  • 4Bd
  • 5Ba
  • 4,413 Sq Ft
$70K
102 Boatswain Way UNIT 32, Chester, MD 21619
  • $809,990
  • 2Bd
  • 3Ba
  • 1,900 Sq Ft
$10K
102 Boatswain Way UNIT 33, Chester, MD 21619
  • $809,990
  • 2Bd
  • 3Ba
  • 1,900 Sq Ft
$10K
215 Kingfisher Ln, Chester, MD 21619
  • $995,000
  • 5Bd
  • 5Ba
  • 3,225 Sq Ft
$54.5K
1000 Herons Nest Way #22, Chester, MD 21619
  • $485,000
  • 2Bd
  • 3Ba
  • 1,900 Sq Ft
$3K
4000 Herons Nest Way #22, Chester, MD 21619
  • $492,500
  • 2Bd
  • 3Ba
  • 1,900 Sq Ft
$6.5K
131 Flycatcher Way, Chester, MD 21619
  • $669,990
  • 2Bd
  • 2Ba
  • 1,993 Sq Ft
$25K
131 Flycatcher Way, Chester, MD 21619
  • $702,990
  • 2Bd
  • 2Ba
  • 2,010 Sq Ft
$3K
131 Flycatcher Way, Chester, MD 21619
  • $822,990
  • 3Bd
  • 3Ba
  • 2,789 Sq Ft
$3K
131 Flycatcher Way, Chester, MD 21619
  • $886,990
  • 4Bd
  • 3Ba
  • 3,512 Sq Ft
$25K
131 Flycatcher Way, Chester, MD 21619
  • $712,990
  • 2Bd
  • 2Ba
  • 2,143 Sq Ft
$3K
131 Flycatcher Way, Chester, MD 21619
  • $883,990
  • 4Bd
  • 3Ba
  • 3,601 Sq Ft
$25K
131 Flycatcher Way, Chester, MD 21619
  • $858,990
  • 3Bd
  • 3Ba
  • 2,930 Sq Ft
$25K
131 Flycatcher Way, Chester, MD 21619
  • $701,990
  • 4Bd
  • 3Ba
  • 2,791 Sq Ft
$25K
131 Flycatcher Way, Chester, MD 21619
  • $851,990
  • 5Bd
  • 4Ba
  • 3,225 Sq Ft
$3K
131 Flycatcher Way, Chester, MD 21619
  • $599,990
  • 3Bd
  • 2Ba
  • 2,602 Sq Ft
$800K
131 Flycatcher Way, Chester, MD 21619
  • $519,990
  • 2Bd
  • 2Ba
  • 1,900 Sq Ft
$800K
131 Flycatcher Way, Chester, MD 21619
  • $519,990
  • 2Bd
  • 2Ba
  • 2,003 Sq Ft
$800K
3000 Herons Nest Way #11, Chester, MD 21619
  • $460,000
  • 2Bd
  • 3Ba
  • 2,003 Sq Ft
$38.4K
1757 Harbor Dr, Chester, MD 21619
  • $1,198,800
  • 4Bd
  • 4Ba
$4K
1405 Little Creek Rd, Chester, MD 21619
  • $19,500
  • 2Bd
  • 1Ba
  • 764 Sq Ft
1340 Queen Anne Dr, Chester, MD 21619
  • $439,900
  • 3Bd
  • 2Ba
  • 1,248 Sq Ft
$10K
Parks Road, Chester, MD 21619
  • $275,000
  • 0.68 Acre
$25K
51 - 100 of 138 Homes for sale in Chester, MD
1 2 3
By entering my info and clicking Submit below, I am providing my e-signature and express written consent to receive marketing emails, calls, and texts (including via automatic telephone dialing systems, AI generative, artificial or pre-recorded voice technology) relating to my inquiry from Movoto (and parties calling/messaging on their behalf) even if my number appears on the company, state, or national Do Not Call Registry. You also agree to ourTerms and Conditions and Privacy Policy. Consent not required to receive services (call 1-844-420-1270 to be connected without providing consent).

Explore nearby locations

The prices shown are the median list prices.

Narrow your search

Chester, MD real estate market trends

Statistics as of October 2026
$719K
Avg. list price
$323/Sqft
Avg. price/sqft
144
Homes for sale
2,010 Sqft
Avg. home size
78 Days
Avg. days on market
Movoto makes it easy to track market trends in Chester, MD. Whether you’re entering the market or planning your next move, understanding these key metrics can guide smart decisions. Looking for more detailed housing market stats in Chester, MD?
Schools
Chester, MD Schools. Ratings provided by great school See all…

Frequently Asked Questions about Chester, MD

Meet with a real estate agent today (844) 417-0593
  • Movoto Logo
  • Download IOS APP Download Android APP
The multiple listing information is provided by . 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. Buyer to verify all information. The information provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing information updated every 15 minutes. Terms of use & Privacy Policy, California Privacy Info. Copyright © 2005 - 2026 Movoto, Inc. All rights reserved. Equal Housing Opportunity CalDRE CalDRE #01517281
Movoto Real Estate is committed to ensuring accessibility for individuals with disabilities. We are continuously working to improve the accessibility of our web experience for everyone. We welcome feedback and accommodation requests, please submit them here.
© 2026 BRIGHT, All Rights Reserved
Information Deemed Reliable But Not Guaranteed
The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Movoto participates, and is provided by BRIGHT through a licensing agreement.The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated: 10/15/2026. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closedor are no longer being offered for sale. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. This home sale information is not to be construed as an appraisal and may not be used as such for any purpose. BRIGHTMLS is the (or a) provider of this home sale information and has compiled content from various sources. Some properties represented may not have actually solddue to reporting errors.
Requests for information regarding mortgage products will be directed to Movoto.com affiliate, Lower, LLC - a licensed Mortgage Lender (NMLS #1124061), or, based on your location, may be redirected to a participating mortgage marketing partner that may pay Lower, LLC for any consumer contact information provided through this site.