New50$769,900
2 bd · 3 ba · 2,014 sqft
168 Redstart Dr, Chester, MD
Carol L Tinnin · RE/MAX Leading Edge
Homes for Sale in Chester, MD
Hide MapHomes for Sale in Chester, MD
24 of 62 Listings
New50$769,900
2 bd · 3 ba · 2,014 sqft
168 Redstart Dr, Chester, MD
Carol L Tinnin · RE/MAX Leading Edge
25$999,990
3 bd · 3 ba · 2,772 sqft
114 Kinglet Ct, Chester, MD
David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP
27$899,990
3 bd · 3 ba · 2,772 sqft
247 Redstart Dr, Chester, MD
David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP
25$969,990
2 bd · 3 ba · 2,010 sqft
118 Kinglet Ct, Chester, MD
David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP
45$635,000
5 bd · 3 ba · 2,818 sqft
1616 Postal Rd, Chester, MD
Carol Eaton · Coldwell Banker Realty
31$410,000
3 bd · 3 ba · 1,899 sqft
510 Auckland Way, Chester, MD
Dawn Haskins Smith · Engel & Volkers Annapolis
49$539,000
2 bd · 3 ba · 1,680 sqft
15-E Queen Anne Way #E, Chester, MD
Jason French · Benson & Mangold, LLC
90$859,900
3 bd · 2 ba · 2,331 sqft
320 Bayberry Dr, Chester, MD
Carol L Tinnin · RE/MAX Leading Edge
34$599,900
3 bd · 4 ba · 2,076 sqft
1012 Auckland Way, Chester, MD
Jerrise Spencer · Redfin Corp
45$595,000
3 bd · 4 ba · 2,100 sqft
1010 Auckland Way, Chester, MD
Lori G Woods-Fortney · Berkshire Hathaway HomeServices Homesale Realty
56$665,000
2 bd · 3 ba · 1,993 sqft
228 Bayberry Dr, Chester, MD
Amy B Faust · Long & Foster Real Estate, Inc.
38$329,000
2 bd · 3 ba · 1,440 sqft
53-E Queen Caroline Ct, Chester, MD
Tammy Studebaker · EXP Realty, LLC
54$349,000
3 bd · 3 ba · 1,302 sqft
6005 Bridgepointe Dr, Chester, MD
Megan E Rosendale · Rosendale Realty
56$550,000
2 bd · 3 ba · 1,616 sqft
47-F Queen Anne Way, Chester, MD
Debra P Noone · Northrop Realty
Price Reduced23$639,990
2 bd · 2 ba · 1,690 sqft
641 Warbler Way, Chester, MD
David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP
28$350,000
2 bd · 2 ba · 1,274 sqft
200 Church St, Chester, MD
Darlene L Winegardner · RE/MAX Executive
48$400,000
5 bd · 4 ba · 3,250 sqft
1868 Roberta Dr, Chester, MD
Carley R. Cooper · Alex Cooper Auctioneers, Inc.
Price Reduced83$525,000
5 bd · 4 ba · 3,552 sqft
326 Castle Marina Rd, Chester, MD
Virginia Elizabeth Dauses · Coldwell Banker Waterman Realty
77$1,250,000
3 bd · 3 ba · 2,742 sqft
1717 Harbor Dr, Chester, MD
Samantha A Grimes · Chesapeake Real Estate Associates, LLC
47$719,990
2 bd · 3 ba · 1,900 sqft
736 Warbler Way #2733, Chester, MD
David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP
Price Reduced26$379,900
3 bd · 3 ba · 1,899 sqft
108 Blenny Ln, Chester, MD
Carol L Tinnin · RE/MAX Leading Edge
96$819,900
3 bd · 3 ba · 2,479 sqft
207 Thomas White Blvd, Chester, MD
Tim Karns · RE/MAX Components
91$789,000
3 bd · 3 ba · 2,787 sqft
402 Macum Creek Dr, Chester, MD
Tara Trout · Samson Properties
39$660,000
2 bd · 2 ba · 2,473 sqft
118 Broadwater Dr, Chester, MD
Ralph S. Kennedy · RE/MAX Executive
Bright MLSSource: HJN community data
August 2026
Selling at 99.4% of asking price
Buyers here are paying below asking. MLS · 15 sales · as of Aug 26, 2026