New56$599,990
2 bd · 3 ba · 2,003 sqft
148 Flagstaff Way #2312, Chester, MD
David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP
Homes for Sale in Chester, MD
Hide MapHomes for Sale in Chester, MD
24 of 74 Listings
New56$599,990
2 bd · 3 ba · 2,003 sqft
148 Flagstaff Way #2312, Chester, MD
David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP
35$979,990
4 bd · 4 ba · 3,512 sqft
727 Warbler Way, Chester, MD
David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP
52$675,000
3 bd · 3 ba · 2,602 sqft
190 Harrier Way #24, Chester, MD
Dee Dee R McCracken · Coldwell Banker Realty
65$559,900
3 bd · 2 ba · 1,640 sqft
200 Anchor Ln, Chester, MD
Jennifer Norfolk · Coldwell Banker Waterman Realty
Price Reduced76$698,000
2 bd · 3 ba · 1,900 sqft
121 Switchgrass Way #42, Chester, MD
Steven Knopf · Engel & Volkers Annapolis
3$199,900
3 bd · 2 ba · 1,080 sqft
406 Dominion Rd, Chester, MD
Daniel J. Demers · Sell Your Home Services
45$699,000
3 bd · 2 ba · 1,584 sqft
2627 Cecil Dr, Chester, MD
Linda L Austin · Long & Foster Real Estate, Inc.
33$396,900
3 bd · 2 ba · 1,116 sqft
1837 Harbor, Chester, MD
Norma L Coursey · Benson & Mangold, LLC
50$559,900
3 bd · 3 ba · 2,062 sqft
227 Gibson Cir, Chester, MD
Pamela Doll · RE/MAX Executive
57$700,000
2 bd · 2 ba · 2,025 sqft
244 Warbler Way, Chester, MD
Tara Trout · Samson Properties
30$349,900
3 bd · 3 ba · 1,899 sqft
107 Widgeon Way, Chester, MD
Carol L Tinnin · RE/MAX Leading Edge
Price Reduced26$250,000
2 bd · 2 ba · 1,069 sqft
101 Bufflehead Ct, Chester, MD
Kevin McDermott · The KW Collective
42$699,000
3 bd · 3 ba · 1,560 sqft
2703 Sherman Dr, Chester, MD
Tammy D Rosendale · Rosendale Realty
26$400,000
2 bd · 2 ba · 1,260 sqft
1-F Queen Victoria Ct, Chester, MD
Doris Williams · Douglas Realty LLC
42$545,000
3 bd · 3 ba · 2,100 sqft
100 Schooner Way, Chester, MD
Lauren Matera · LPT Realty, LLC
Price Reduced20$305,000
3 bd · 1 ba · 960 sqft
107 Lee Rd, Chester, MD
Verria Hairston · Open Door Brokerage, LLC
Price Reduced47$779,990
2 bd · 3 ba · 1,900 sqft
830 Warbler Way #2843, Chester, MD
David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP
53$1,350,000
4 bd · 3 ba · 3,680 sqft
1509 Calvert Rd, Chester, MD
Jimmy J White Jr. · Long & Foster Real Estate, Inc.
22$300,000
3 bd · 2 ba · 1,160 sqft
205 Dominion Ln, Chester, MD
Jonathan C Nicholls · EXP Realty, LLC
Price Reduced50$749,900
2 bd · 3 ba · 2,014 sqft
168 Redstart Dr, Chester, MD
Carol L Tinnin · RE/MAX Leading Edge
36$744,900
2 bd · 3 ba · 1,900 sqft
111 Marshgrass Way #43, Chester, MD
Jimmy J White Jr. · Long & Foster Real Estate, Inc.
44$599,000
5 bd · 3 ba · 1,852 sqft
231 Dominion Rd, Chester, MD
Dane P Ways · Long & Foster Real Estate, Inc.
60$1,399,000
3 bd · 3 ba · 2,601 sqft
129 Wheelhouse Way #21, Chester, MD
Christina L Eury · Rise Real Estate, LLC
44$549,950
2 bd · 3 ba · 2,000 sqft
630 Warbler Way #12, Chester, MD
Ralph S. Kennedy · RE/MAX Executive
Bright MLSSource: HJN community data
October 2026 · This period is still settling
Selling at 100.0% of asking price
Sales here are closing essentially at asking. MLS · 14 sales · as of Oct 30, 2026