26$275,000
2 bd · 2 ba · 1,069 sqft
101 Bufflehead Ct, Chester, MD
Kevin McDermott · The KW Collective
Condos in Chester, MD
Hide MapCondos in Chester, MD
24 of 28 Listings
26$275,000
2 bd · 2 ba · 1,069 sqft
101 Bufflehead Ct, Chester, MD
Kevin McDermott · The KW Collective
51$749,990
3 bd · 3 ba · 2,602 sqft
830 Warbler Way #2824, Chester, MD
David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP
47$789,990
2 bd · 3 ba · 1,900 sqft
830 Warbler Way #2843, Chester, MD
David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP
53$599,900
3 bd · 4 ba · 2,100 sqft
208 Widgeon Way, Chester, MD
Carol L Tinnin · RE/MAX Leading Edge
37$744,900
2 bd · 3 ba · 1,900 sqft
111 Marshgrass Way #43, Chester, MD
Jimmy J White Jr. · Long & Foster Real Estate, Inc.
39$549,950
2 bd · 3 ba · 2,000 sqft
630 Warbler Way #12, Chester, MD
Ralph S. Kennedy · RE/MAX Executive
39$499,000
2 bd · 3 ba · 1,680 sqft
7-B Queen Victoria Way #B, Chester, MD
Christina Sousa · RE/MAX Allegiance
31$410,000
3 bd · 3 ba · 1,899 sqft
510 Auckland Way, Chester, MD
Dawn Haskins Smith · Engel & Volkers Annapolis
51$539,000
2 bd · 3 ba · 1,680 sqft
15-E Queen Anne Way #E, Chester, MD
Jason French · Benson & Mangold, LLC
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
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
Price Reduced37$369,900
3 bd · 3 ba · 1,899 sqft
108 Blenny Ln, Chester, MD
Carol L Tinnin · RE/MAX Leading Edge
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 Reduced23$499,000
2 bd · 3 ba · 2,003 sqft
230 Switchgrass Way #12, Chester, MD
David J. Moore · Real Broker, LLC - Chester
Price Reduced50$595,000
2 bd · 3 ba · 1,832 sqft
1000 Herons Nest Way #43, Chester, MD
Dee Dee R McCracken · Coldwell Banker Realty
Price Reduced48$429,900
3 bd · 3 ba · 1,595 sqft
106 Bodys Neck Rd, Chester, MD
William Warren Longest Jr. · Realty Navigator
40$585,000
2 bd · 3 ba · 2,003 sqft
129 Wheelhouse Way #11, Chester, MD
Jennifer Anne Thomas · RE/MAX Executive
Price Reduced46$315,000
3 bd · 3 ba · 1,302 sqft
5011 Bridgepointe Dr, Chester, MD
Nickolaus B Waldner · Keller Williams Realty Centre
Price Reduced40$318,500
2 bd · 3 ba · 1,312 sqft
45-G Queen Neva Ct, Chester, MD
John V Freeman · Coldwell Banker Realty
Condos in Chester, MD: 28 active listings as of .
Bright MLSSource: HJN community data
September 2026 · This period is still settling
Selling at 99.0% of asking price
Buyers here are paying below asking. MLS · 16 sales · as of Sep 30, 2026