90$859,900
3 bd · 2 ba · 2,331 sqft
320 Bayberry 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 68 Listings
90$859,900
3 bd · 2 ba · 2,331 sqft
320 Bayberry Dr, Chester, MD
Carol L Tinnin · RE/MAX Leading Edge
51$375,000
3 bd · 4 ba · 1,899 sqft
512 Auckland Way, Chester, MD
Lawrence Doyle · Long & Foster Real Estate, Inc.
36$599,900
3 bd · 4 ba · 2,076 sqft
1012 Auckland Way, Chester, MD
Jerrise Spencer · Redfin Corp
28$570,000
2 bd · 2 ba · 1,380 sqft
34 Queen Anne Way #a, Chester, MD
Jennifer Anne Thomas · RE/MAX Executive
55$595,000
3 bd · 4 ba · 2,100 sqft
1010 Auckland Way, Chester, MD
Lori G Woods-Fortney · Berkshire Hathaway HomeServices Homesale Realty
38$329,000
2 bd · 3 ba · 1,440 sqft
53-E Queen Caroline Ct, Chester, MD
Tammy Studebaker · EXP Realty, LLC
47$689,990
2 bd · 3 ba · 1,900 sqft
830 Warbler Way #2833, Chester, MD
David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP
56$665,000
2 bd · 3 ba · 1,993 sqft
228 Bayberry Dr, Chester, MD
Amy B Faust · Long & Foster Real Estate, Inc.
Price Reduced49$795,000
4 bd · 3 ba · 2,870 sqft
231 Evelyne St, Chester, MD
Tricia Z Wilson · Wilson Realty & Staging LLC
Price Reduced54$324,000
3 bd · 3 ba · 1,302 sqft
6005 Bridgepointe Dr, Chester, MD
Megan E Rosendale · Rosendale Realty
42$790,000
3 bd · 2 ba · 2,331 sqft
117 Harrier Way, Chester, MD
Jennifer Anne Thomas · RE/MAX Executive
Price Reduced83$499,000
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
Price Reduced37$364,900
3 bd · 3 ba · 1,899 sqft
108 Blenny Ln, Chester, MD
Carol L Tinnin · RE/MAX Leading Edge
Price Reduced48$645,000
2 bd · 2 ba · 2,473 sqft
118 Broadwater Dr, Chester, MD
Ralph S. Kennedy · RE/MAX Executive
Price Reduced68$874,000
3 bd · 3 ba · 2,745 sqft
214 Bayberry Dr, Chester, MD
James C Corson · Benson & Mangold, LLC
Price Reduced123$737,900
4 bd · 3 ba · 3,142 sqft
209 Harrier Way, Chester, MD
Violeta I Aguirre · Long & Foster Real Estate, Inc.
Price Reduced53$829,000
4 bd · 3 ba · 3,168 sqft
113 Bentons Pleasure Rd, Chester, MD
Temple H Peirce Jr. · Cummings & Co. Realtors
Price Reduced47$809,990
2 bd · 3 ba · 1,900 sqft
102 Boatswain Way #2932, Chester, MD
David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP
Price Reduced47$909,990
2 bd · 3 ba · 1,900 sqft
102 Boatswain Way #2943, Chester, MD
David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP
56$998,000
3 bd · 3 ba · 2,602 sqft
111 Marshgrass Way #41, Chester, MD
Margaret W Moran · Long & Foster Real Estate, Inc.
Price Reduced47$809,990
2 bd · 3 ba · 1,900 sqft
102 Boatswain Way #2933, Chester, MD
David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP
Price Reduced63$739,000
4 bd · 4 ba · 2,185 sqft
134 Richard Ingle Way, Chester, MD
Barbara A McCaffrey · Redfin Corp
Price Reduced23$499,000
2 bd · 3 ba · 2,003 sqft
230 Switchgrass Way #12, Chester, MD
David J. Moore · Real Broker, LLC - Chester
Bright MLSSource: HJN community data
September 2026
Selling at 99.0% of asking price
Buyers here are paying below asking. MLS · 16 sales · as of Sep 30, 2026