New48$400,000
5 bd · 4 ba · 3,250 sqft
1868 Roberta Dr, Chester, MD
Carley R. Cooper · Alex Cooper Auctioneers, Inc.
Homes for Sale in Chester, MD
Hide MapHomes for Sale in Chester, MD
24 of 67 Listings
New48$400,000
5 bd · 4 ba · 3,250 sqft
1868 Roberta Dr, Chester, MD
Carley R. Cooper · Alex Cooper Auctioneers, Inc.
54$629,990
2 bd · 3 ba · 2,003 sqft
110 Boatswain Way #3012, Chester, MD
David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP
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
46$569,900
4 bd · 3 ba · 2,332 sqft
233 Cross Creek Ct, Chester, MD
Christopher B Nagel · Rory S. Coakley Realty, Inc.
Price Reduced60$1,290,000
5 bd · 2 ba · 2,700 sqft
2513 Cecil Dr, Chester, MD
David J. Moore · Real Broker, LLC - Chester
Price Reduced26$789,990
2 bd · 3 ba · 2,010 sqft
536 Warbler Way, Chester, MD
David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP
26$389,900
3 bd · 3 ba · 1,899 sqft
108 Blenny Ln, Chester, MD
Carol L Tinnin · RE/MAX Leading Edge
82$819,900
3 bd · 3 ba · 2,479 sqft
207 Thomas White Blvd, Chester, MD
Tim Karns · RE/MAX Components
68$924,000
3 bd · 3 ba · 2,745 sqft
214 Bayberry Dr, Chester, MD
James C Corson · Benson & Mangold, LLC
35$859,500
3 bd · 3 ba · 2,602 sqft
201 Switchgrass Way #34, Chester, MD
Bradley R Kappel · TTR Sotheby's International Realty
25$1,200,000
3 bd · 4 ba · 2,930 sqft
117 Flycatcher Way, Chester, MD
David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP
26$1,100,000
3 bd · 3 ba · 2,789 sqft
123 Flycatcher Way, Chester, MD
David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP
25$1,200,000
5 bd · 5 ba · 3,225 sqft
111 Flycatcher Way, Chester, MD
David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP
66$899,000
3 bd · 3 ba · 2,464 sqft
148 Elinor St, Chester, MD
Tara Trout · Samson Properties
79$897,750
3 bd · 2 ba · 2,331 sqft
320 Bayberry Dr, Chester, MD
Jeremy Michael McDonough · Mr. Lister Realty
39$825,000
4 bd · 3 ba · 3,291 sqft
313 Thomas White Blvd, Chester, MD
Carol Snyder · Monument Sotheby's International Realty
123$747,900
4 bd · 3 ba · 3,142 sqft
209 Harrier Way, Chester, MD
Violeta I Aguirre · Long & Foster Real Estate, Inc.
2$868,000
4 bd · 3 ba · 3,168 sqft
113 Bentons Pleasure Rd, Chester, MD
Temple H Peirce Jr. · Cummings & Co. Realtors
Price Reduced47$819,990
2 bd · 3 ba · 1,900 sqft
102 Boatswain Way #2932, Chester, MD
David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP
Price Reduced47$919,990
2 bd · 3 ba · 1,900 sqft
102 Boatswain Way #2943, Chester, MD
David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP
63$989,800
5 bd · 4 ba · 3,036 sqft
203 Riverside Dr, Chester, MD
Christine Schultz · Long & Foster Real Estate, Inc.
49$345,000
3 bd · 2 ba · 1,080 sqft
1609 Crab Alley Dr, Chester, MD
DeAnna W Miller · Paul Wesley Real Estate
56$998,000
3 bd · 3 ba · 0 sqft
111 Marshgrass Way #41, Chester, MD
Margaret W Moran · Long & Foster Real Estate, Inc.
Price Reduced56$619,990
2 bd · 3 ba · 2,003 sqft
102 Boatswain Way #2911, Chester, MD
David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP
Bright MLSSource: HJN community data
August 2026 · This period is still settling
Selling at 99.4% of asking price
Buyers here are paying below asking. MLS · 15 sales · as of Aug 26, 2026