Listings in 21620 - QUEENANNES County, Maryland
Displaying 1 – 200 of 217 Real estate listings
8620 PARK DRIVE
CHESTERTOWN, MD | Active
Listed: Oct, 25, 2025
Price: $499,900
Living Area: 2,524 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Oct, 25, 2025
Price: $499,900
Living Area: 2,524 Sq. Ft.
8293 BRICES MILL ROAD
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $799,999
Living Area: 2,836 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $799,999
Living Area: 2,836 Sq. Ft.
225 DUKE OF KENT STREET
CHESTERTOWN, MD | Closed
Listed: Aug, 26, 2025
Price: $399,900
Living Area: 1,850 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Aug, 26, 2025
Price: $399,900
Living Area: 1,850 Sq. Ft.
103 ADELA WAY
CHESTERTOWN, MD | Closed
Listed: Aug, 18, 2025
Price: $595,000
Living Area: 5,576 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Aug, 18, 2025
Price: $595,000
Living Area: 5,576 Sq. Ft.
126 METCALF ROAD
CHESTERTOWN, MD | Closed
Listed: Sep, 24, 2025
Price: $230,000
Living Area: 1,140 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Sep, 24, 2025
Price: $230,000
Living Area: 1,140 Sq. Ft.
349 HIGH STREET
CHESTERTOWN, MD | Active Under Contract
Listed: Jun, 03, 2024
Price: $395,000
Living Area: 3,664 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Jun, 03, 2024
Price: $395,000
Living Area: 3,664 Sq. Ft.
7483 SHORTALL STREET
CHESTERTOWN, MD | Closed
Listed: Aug, 28, 2025
Price: $290,000
Living Area: 1,232 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Aug, 28, 2025
Price: $290,000
Living Area: 1,232 Sq. Ft.
907 N MEADOWVIEW DRIVE
CHESTERTOWN, MD | Closed
Listed: Aug, 04, 2025
Price: $410,000
Living Area: 1,842 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Aug, 04, 2025
Price: $410,000
Living Area: 1,842 Sq. Ft.
25195 LOVERS LANE
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $350,000
Living Area: 1,002 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $350,000
Living Area: 1,002 Sq. Ft.
300 HILLTOP LANE
CHESTERTOWN, MD | Closed
Listed: Nov, 26, 2025
Price: $2,000
Living Area: 1,200 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Nov, 26, 2025
Price: $2,000
Living Area: 1,200 Sq. Ft.
203 HILLTOP LANE
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $115,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $115,000
Living Area: 0 Sq. Ft.
2007 PONDTOWN ROAD
CHESTERTOWN, MD | Closed
Listed: Jan, 24, 2019
Price: $35,000
Living Area: 448 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 24, 2019
Price: $35,000
Living Area: 448 Sq. Ft.
101 RIVER ROAD
CHESTERTOWN, MD | Closed
Listed: Sep, 23, 2019
Price: $248,000
Living Area: 2,304 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Sep, 23, 2019
Price: $248,000
Living Area: 2,304 Sq. Ft.
509 FEY ROAD
CHESTERTOWN, MD | Closed
Listed: Aug, 21, 2019
Price: $599,000
Living Area: 2,906 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Aug, 21, 2019
Price: $599,000
Living Area: 2,906 Sq. Ft.
21341 PERSIMMON DRIVE 17
CHESTERTOWN, MD | Closed
Listed: Dec, 04, 2023
Price: $157,000
Living Area: 1,269 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Dec, 04, 2023
Price: $157,000
Living Area: 1,269 Sq. Ft.
5700 JOHNSONTOWN ROAD
CHESTERTOWN, MD | Closed
Listed: Aug, 10, 2025
Price: $110,000
Living Area: 1,144 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Aug, 10, 2025
Price: $110,000
Living Area: 1,144 Sq. Ft.
508 CANNON STREET
CHESTERTOWN, MD | Closed
Listed: May, 11, 2025
Price: $150,000
Living Area: 2,240 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: May, 11, 2025
Price: $150,000
Living Area: 2,240 Sq. Ft.
603 ROUND TOP ROAD
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $179,987
Living Area: 1,250 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $179,987
Living Area: 1,250 Sq. Ft.
304 PRINCESS ANNE DRIVE
CHESTERTOWN, MD | Closed
Listed: Jul, 10, 2019
Price: $299,000
Living Area: 1,722 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jul, 10, 2019
Price: $299,000
Living Area: 1,722 Sq. Ft.
123 HEATH ROAD
CHESTERTOWN, MD | Closed
Listed: Aug, 21, 2021
Price: $235,000
Living Area: 1,792 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Aug, 21, 2021
Price: $235,000
Living Area: 1,792 Sq. Ft.
105 LYONS LANE
CHESTERTOWN, MD | Closed
Listed: Sep, 15, 2021
Price: $260,000
Living Area: 1,192 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Sep, 15, 2021
Price: $260,000
Living Area: 1,192 Sq. Ft.
10145 3RD POINT ROAD
CHESTERTOWN, MD | Closed
Listed: Jul, 24, 2021
Price: $400,000
Living Area: 3,292 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jul, 24, 2021
Price: $400,000
Living Area: 3,292 Sq. Ft.
102 TAMARACK ROAD
CHESTERTOWN, MD | Closed
Listed: Jun, 11, 2023
Price: $2,000
Living Area: 1,150 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 11, 2023
Price: $2,000
Living Area: 1,150 Sq. Ft.
101 BIRCH RUN ROAD
CHESTERTOWN, MD | Closed
Listed: Oct, 12, 2025
Price: $499,999
Living Area: 1,961 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Oct, 12, 2025
Price: $499,999
Living Area: 1,961 Sq. Ft.
206 VALLEY
CHESTERTOWN, MD | Closed
Listed: Sep, 30, 2025
Price: $615,000
Living Area: 2,869 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Sep, 30, 2025
Price: $615,000
Living Area: 2,869 Sq. Ft.
10425 BUNTING ROAD
CHESTERTOWN, MD | Closed
Listed: Oct, 23, 2019
Price: $188,000
Living Area: 1,456 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Oct, 23, 2019
Price: $188,000
Living Area: 1,456 Sq. Ft.
216 BLAKEFIELD DRIVE
CHESTERTOWN, MD | Active
Listed: Nov, 02, 2025
Price: $559,000
Living Area: 2,400 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Nov, 02, 2025
Price: $559,000
Living Area: 2,400 Sq. Ft.
108 PRIMROSE ROAD
CHESTERTOWN, MD | Closed
Listed: Oct, 06, 2025
Price: $375,000
Living Area: 1,722 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Oct, 06, 2025
Price: $375,000
Living Area: 1,722 Sq. Ft.
105 PEARL CREEK LANE
CHESTERTOWN, MD | Active Under Contract
Listed: Jan, 21, 2026
Price: $449,000
Living Area: 1,961 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Jan, 21, 2026
Price: $449,000
Living Area: 1,961 Sq. Ft.
100 METCALF ROAD
CHESTERTOWN, MD | Closed
Listed: Aug, 28, 2025
Price: $245,000
Living Area: 1,140 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Aug, 28, 2025
Price: $245,000
Living Area: 1,140 Sq. Ft.
HOFFECKER ROAD
CHESTERTOWN, MD | Pending
Listed: Jan, 15, 2026
Price: $212,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: Jan, 15, 2026
Price: $212,000
Living Area: 0 Sq. Ft.
OLD MORGNEC ROAD
CHESTERTOWN, MD | Active
Listed: Mar, 25, 2025
Price: $59,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 25, 2025
Price: $59,000
Living Area: 0 Sq. Ft.
25800 COLLINS AVENUE
CHESTERTOWN, MD | Closed
Listed: Aug, 28, 2025
Price: $435,000
Living Area: 2,162 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Aug, 28, 2025
Price: $435,000
Living Area: 2,162 Sq. Ft.
5179 QUAKER NECK ROAD
CHESTERTOWN, MD | Closed
Listed: May, 17, 2025
Price: $559,900
Living Area: 1,148 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: May, 17, 2025
Price: $559,900
Living Area: 1,148 Sq. Ft.
110 S MILL STREET
CHESTERTOWN, MD | Closed
Listed: Aug, 19, 2025
Price: $745,000
Living Area: 2,492 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Aug, 19, 2025
Price: $745,000
Living Area: 2,492 Sq. Ft.
23620 LANDS END ROAD
CHESTERTOWN, MD | Closed
Listed: May, 21, 2025
Price: $4,850,000
Living Area: 9,852 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: May, 21, 2025
Price: $4,850,000
Living Area: 9,852 Sq. Ft.
CAULKS FIELD ROAD
CHESTERTOWN, MD | Active
Listed: Apr, 26, 2025
Price: $150,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Apr, 26, 2025
Price: $150,000
Living Area: 0 Sq. Ft.
ELM ROAD
CHESTERTOWN, MD | Active Under Contract
Listed: Jul, 29, 2024
Price: $40,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Jul, 29, 2024
Price: $40,000
Living Area: 0 Sq. Ft.
7844 CHESTER COURT
CHESTERTOWN, MD | Active
Listed: Oct, 23, 2025
Price: $745,000
Living Area: 3,248 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Oct, 23, 2025
Price: $745,000
Living Area: 3,248 Sq. Ft.
7521 PINE AVENUE
CHESTERTOWN, MD | Closed
Listed: Nov, 17, 2025
Price: $250,000
Living Area: 1,040 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Nov, 17, 2025
Price: $250,000
Living Area: 1,040 Sq. Ft.
107 MALONE AVENUE
CHESTERTOWN, MD | Closed
Listed: Oct, 01, 2025
Price: $290,000
Living Area: 1,200 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Oct, 01, 2025
Price: $290,000
Living Area: 1,200 Sq. Ft.
7653 BROAD NECK ROAD
CHESTERTOWN, MD | Closed
Listed: Sep, 25, 2025
Price: $375,000
Living Area: 1,790 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Sep, 25, 2025
Price: $375,000
Living Area: 1,790 Sq. Ft.
10230 JOHN CARVILL ROAD
CHESTERTOWN, MD | Closed
Listed: Nov, 03, 2025
Price: $750,000
Living Area: 2,350 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Nov, 03, 2025
Price: $750,000
Living Area: 2,350 Sq. Ft.
129 PARMA ROAD
CHESTERTOWN, MD | Active
Listed: Jan, 09, 2026
Price: $330,000
Living Area: 1,170 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jan, 09, 2026
Price: $330,000
Living Area: 1,170 Sq. Ft.
LOT 24 & 25 BUCK NECK ROAD
CHESTERTOWN, MD | Closed
Listed: Feb, 05, 2025
Price: $8,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Feb, 05, 2025
Price: $8,000
Living Area: 0 Sq. Ft.
300 HICKORY LANE
CHESTERTOWN, MD | Closed
Listed: Jun, 19, 2025
Price: $1,198,000
Living Area: 3,640 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 19, 2025
Price: $1,198,000
Living Area: 3,640 Sq. Ft.
204 ROLLING ROAD
CHESTERTOWN, MD | Active Under Contract
Listed: Nov, 07, 2025
Price: $345,000
Living Area: 2,296 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Nov, 07, 2025
Price: $345,000
Living Area: 2,296 Sq. Ft.
213 CENTRAL DRIVE
CHESTERTOWN, MD | Active Under Contract
Listed: Dec, 01, 2025
Price: $314,900
Living Area: 1,232 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Dec, 01, 2025
Price: $314,900
Living Area: 1,232 Sq. Ft.
#35 LANDING LANE
CHESTERTOWN, MD | Active
Listed: Dec, 04, 2025
Price: $786,900
Living Area: 1,964 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Dec, 04, 2025
Price: $786,900
Living Area: 1,964 Sq. Ft.
LITTLE HARBOR WAY 1
CHESTERTOWN, MD | Active
Listed: Nov, 10, 2025
Price: $1,459,000
Living Area: 2,231 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Nov, 10, 2025
Price: $1,459,000
Living Area: 2,231 Sq. Ft.
LITTLE HARBOR WAY 1
CHESTERTOWN, MD | Active
Listed: Apr, 03, 2025
Price: $1,800,000
Living Area: 3,540 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Apr, 03, 2025
Price: $1,800,000
Living Area: 3,540 Sq. Ft.
106 LANDING LANE
CHESTERTOWN, MD | Active
Listed: Nov, 10, 2025
Price: $799,900
Living Area: 2,092 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Nov, 10, 2025
Price: $799,900
Living Area: 2,092 Sq. Ft.
GEORGETOWN ROAD
CHESTERTOWN, MD | Active
Listed: Nov, 19, 2025
Price: $89,500
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Nov, 19, 2025
Price: $89,500
Living Area: 0 Sq. Ft.
23069 RALEIGH ROAD
CHESTERTOWN, MD | Pending
Listed: Jun, 25, 2025
Price: $175,000
Living Area: 1,160 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: Jun, 25, 2025
Price: $175,000
Living Area: 1,160 Sq. Ft.
109 WATER STREET
CHESTERTOWN, MD | Pending
Listed: Jan, 17, 2026
Price: $650,000
Living Area: 2,064 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: Jan, 17, 2026
Price: $650,000
Living Area: 2,064 Sq. Ft.
311 DEVON DRIVE
CHESTERTOWN, MD | Active
Listed: Nov, 21, 2025
Price: $580,000
Living Area: 3,504 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Nov, 21, 2025
Price: $580,000
Living Area: 3,504 Sq. Ft.
FISH HATCHERY ROAD
CHESTERTOWN, MD | Active
Listed: Jan, 03, 2025
Price: $5,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jan, 03, 2025
Price: $5,000
Living Area: 0 Sq. Ft.
21111 TEXAS AVENUE
CHESTERTOWN, MD | Pending
Listed: Nov, 20, 2025
Price: $370,000
Living Area: 1,680 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: Nov, 20, 2025
Price: $370,000
Living Area: 1,680 Sq. Ft.
134 CHAR NOR MANOR BOULEVARD
CHESTERTOWN, MD | Closed
Listed: Jul, 09, 2025
Price: $279,000
Living Area: 1,128 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jul, 09, 2025
Price: $279,000
Living Area: 1,128 Sq. Ft.
423 CALVERT STREET
CHESTERTOWN, MD | Pending
Listed: Sep, 26, 2025
Price: $135,000
Living Area: 1,136 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: Sep, 26, 2025
Price: $135,000
Living Area: 1,136 Sq. Ft.
101 PINE TREE ROAD
CHESTERTOWN, MD | Active Under Contract
Listed: Feb, 17, 2026
Price: $480,000
Living Area: 1,848 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Feb, 17, 2026
Price: $480,000
Living Area: 1,848 Sq. Ft.
132 PROSPECT STREET
CHESTERTOWN, MD | Active
Listed: Feb, 12, 2026
Price: $199,885
Living Area: 910 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Feb, 12, 2026
Price: $199,885
Living Area: 910 Sq. Ft.
MELITOTA ROAD
CHESTERTOWN, MD | Active Under Contract
Listed: May, 18, 2025
Price: $29,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: May, 18, 2025
Price: $29,000
Living Area: 0 Sq. Ft.
141 PROSPECT STREET
CHESTERTOWN, MD | Pending
Listed: Jan, 06, 2026
Price: $165,000
Living Area: 1,156 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: Jan, 06, 2026
Price: $165,000
Living Area: 1,156 Sq. Ft.
112 METCALF ROAD
CHESTERTOWN, MD | Active
Listed: Jan, 24, 2026
Price: $249,500
Living Area: 1,280 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jan, 24, 2026
Price: $249,500
Living Area: 1,280 Sq. Ft.
BUCK NECK LANDING ROAD
CHESTERTOWN, MD | Active
Listed: Jun, 01, 2024
Price: $9,500
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jun, 01, 2024
Price: $9,500
Living Area: 0 Sq. Ft.
FISH HATCHERY ROAD
CHESTERTOWN, MD | Active
Listed: Jul, 02, 2023
Price: $37,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jul, 02, 2023
Price: $37,000
Living Area: 0 Sq. Ft.
BUCK NECK LANDING ROAD
CHESTERTOWN, MD | Active
Listed: Aug, 15, 2025
Price: $10,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Aug, 15, 2025
Price: $10,000
Living Area: 0 Sq. Ft.
MONTGOMERY AVENUE
CHESTERTOWN, MD | Active
Listed: Dec, 08, 2023
Price: $40,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Dec, 08, 2023
Price: $40,000
Living Area: 0 Sq. Ft.
128 EDMORE ROAD
CHESTERTOWN, MD | Closed
Listed: Mar, 23, 2025
Price: $415,000
Living Area: 2,568 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Mar, 23, 2025
Price: $415,000
Living Area: 2,568 Sq. Ft.
7989 QUAKER NECK ROAD
CHESTERTOWN, MD | Active
Listed: Aug, 27, 2025
Price: $2,500,000
Living Area: 4,305 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Aug, 27, 2025
Price: $2,500,000
Living Area: 4,305 Sq. Ft.
HAACKE DRIVE LOT 3
CHESTERTOWN, MD | Pending
Listed: Dec, 01, 2024
Price: $225,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: Dec, 01, 2024
Price: $225,000
Living Area: 0 Sq. Ft.
SCHEELER ROAD LOT 2
CHESTERTOWN, MD | Pending
Listed: Nov, 20, 2024
Price: $250,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: Nov, 20, 2024
Price: $250,000
Living Area: 0 Sq. Ft.
611 CANNON STREET
CHESTERTOWN, MD | Active
Listed: Nov, 11, 2025
Price: $299,000
Living Area: 920 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Nov, 11, 2025
Price: $299,000
Living Area: 920 Sq. Ft.
201 BOUNDARY AVENUE
CHESTERTOWN, MD | Closed
Listed: Jul, 20, 2025
Price: $449,000
Living Area: 3,096 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jul, 20, 2025
Price: $449,000
Living Area: 3,096 Sq. Ft.
302 PARK ROW OFFICE 2
CHESTERTOWN, MD | Active
Listed: Aug, 20, 2025
Price: $600
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Aug, 20, 2025
Price: $600
Living Area: 0 Sq. Ft.
101 METCALF ROAD
CHESTERTOWN, MD | Closed
Listed: Nov, 04, 2025
Price: $264,900
Living Area: 1,280 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Nov, 04, 2025
Price: $264,900
Living Area: 1,280 Sq. Ft.
GEORGETOWN ROAD SE
CHESTERTOWN, MD | Active
Listed: Apr, 23, 2025
Price: $150,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Apr, 23, 2025
Price: $150,000
Living Area: 0 Sq. Ft.
251 DEVON DRIVE
CHESTERTOWN, MD | Active
Listed: Aug, 04, 2025
Price: $595,000
Living Area: 3,935 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Aug, 04, 2025
Price: $595,000
Living Area: 3,935 Sq. Ft.
206 CANNON STREET
CHESTERTOWN, MD | Closed
Listed: Feb, 23, 2024
Price: $1,150,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Feb, 23, 2024
Price: $1,150,000
Living Area: 0 Sq. Ft.
201 GREENWOOD AVENUE
CHESTERTOWN, MD | Active Under Contract
Listed: Jan, 05, 2026
Price: $495,000
Living Area: 3,984 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Jan, 05, 2026
Price: $495,000
Living Area: 3,984 Sq. Ft.
23055 OLD FAIRLEE ROAD
CHESTERTOWN, MD | Coming Soon
Listed: Jan, 17, 2026
Price: $330,000
Living Area: 1,628 Sq. Ft.
CHESTERTOWN, MD | Coming Soon
Listed: Jan, 17, 2026
Price: $330,000
Living Area: 1,628 Sq. Ft.
109 METCALF ROAD
CHESTERTOWN, MD | Active
Listed: Dec, 09, 2025
Price: $264,900
Living Area: 1,280 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Dec, 09, 2025
Price: $264,900
Living Area: 1,280 Sq. Ft.
302 ROSIN DRIVE
CHESTERTOWN, MD | Closed
Listed: Oct, 26, 2025
Price: $574,000
Living Area: 3,877 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Oct, 26, 2025
Price: $574,000
Living Area: 3,877 Sq. Ft.
119 HIGH STREET
CHESTERTOWN, MD | Closed
Listed: Sep, 28, 2025
Price: $1,250,000
Living Area: 4,409 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Sep, 28, 2025
Price: $1,250,000
Living Area: 4,409 Sq. Ft.
212 LANDING LANE
CHESTERTOWN, MD | Closed
Listed: Feb, 04, 2025
Price: $759,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Feb, 04, 2025
Price: $759,000
Living Area: 0 Sq. Ft.
600 ROSIN DRIVE
CHESTERTOWN, MD | Closed
Listed: Oct, 02, 2025
Price: $415,000
Living Area: 1,300 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Oct, 02, 2025
Price: $415,000
Living Area: 1,300 Sq. Ft.
8951 ORCHARD DRIVE
CHESTERTOWN, MD | Closed
Listed: Oct, 21, 2025
Price: $695,000
Living Area: 3,735 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Oct, 21, 2025
Price: $695,000
Living Area: 3,735 Sq. Ft.
CHURCH HILL ( LOT 2) ROAD
CHESTERTOWN, MD | Closed
Listed: Jul, 10, 2025
Price: $165,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jul, 10, 2025
Price: $165,000
Living Area: 0 Sq. Ft.
517 HIGH STREET
CHESTERTOWN, MD | Closed
Listed: Sep, 25, 2025
Price: $389,900
Living Area: 1,728 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Sep, 25, 2025
Price: $389,900
Living Area: 1,728 Sq. Ft.
200 WASHINGTON AVENUE
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $495,000
Living Area: 2,915 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $495,000
Living Area: 2,915 Sq. Ft.
200 WASHINGTON AVENUE
CHESTERTOWN, MD | Pending
Listed: Aug, 05, 2025
Price: $695,000
Living Area: 2,917 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: Aug, 05, 2025
Price: $695,000
Living Area: 2,917 Sq. Ft.
492 PEAR TREE POINT ROAD
CHESTERTOWN, MD | Closed
Listed: Oct, 07, 2025
Price: $875,000
Living Area: 3,720 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Oct, 07, 2025
Price: $875,000
Living Area: 3,720 Sq. Ft.
6970 POMONA ROAD
CHESTERTOWN, MD | Closed
Listed: Nov, 21, 2019
Price: $1,650,000
Living Area: 3,008 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Nov, 21, 2019
Price: $1,650,000
Living Area: 3,008 Sq. Ft.
510 CANNON STREET
CHESTERTOWN, MD | Closed
Listed: Jul, 30, 2020
Price: $1,200
Living Area: 1,120 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jul, 30, 2020
Price: $1,200
Living Area: 1,120 Sq. Ft.
116 EAST STREET
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $112,500
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $112,500
Living Area: 0 Sq. Ft.
213 BYFORD DRIVE
CHESTERTOWN, MD | Closed
Listed: Jul, 12, 2022
Price: $336,500
Living Area: 1,277 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jul, 12, 2022
Price: $336,500
Living Area: 1,277 Sq. Ft.
508 CANNON STREET
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $1,200
Living Area: 1,120 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $1,200
Living Area: 1,120 Sq. Ft.
510 CANNON STREET
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $1,200
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $1,200
Living Area: 0 Sq. Ft.
105 HOLLY COURT
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $254,900
Living Area: 2,285 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $254,900
Living Area: 2,285 Sq. Ft.
917 ROUND TOP ROAD
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $169,990
Living Area: 1,008 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $169,990
Living Area: 1,008 Sq. Ft.
206 PINE STREET
CHESTERTOWN, MD | Closed
Listed: Aug, 05, 2021
Price: $249,900
Living Area: 1,616 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Aug, 05, 2021
Price: $249,900
Living Area: 1,616 Sq. Ft.
421 CALVERT STREET
CHESTERTOWN, MD | Closed
Listed: Jul, 09, 2019
Price: $975
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jul, 09, 2019
Price: $975
Living Area: 0 Sq. Ft.
7071 POMONA ROAD
CHESTERTOWN, MD | Closed
Listed: Feb, 10, 2022
Price: $590,000
Living Area: 2,544 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Feb, 10, 2022
Price: $590,000
Living Area: 2,544 Sq. Ft.
Lot 9 PRESTWICK DRIVE
CHESTERTOWN, MD | Active Under Contract
Listed: May, 05, 2024
Price: $185,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: May, 05, 2024
Price: $185,000
Living Area: 0 Sq. Ft.
302 PARK ROW BASEMENT OFFICE 3
CHESTERTOWN, MD | Active
Listed: Jan, 15, 2026
Price: $475
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jan, 15, 2026
Price: $475
Living Area: 0 Sq. Ft.
303 E CAMPUS AVENUE
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $280,000
Living Area: 1,532 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $280,000
Living Area: 1,532 Sq. Ft.
303 E CAMPUS AVENUE
CHESTERTOWN, MD | Closed
Listed: Oct, 25, 2025
Price: $363,000
Living Area: 1,532 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Oct, 25, 2025
Price: $363,000
Living Area: 1,532 Sq. Ft.
218 CAMELOT DRIVE
CHESTERTOWN, MD | Active
Listed: Dec, 14, 2025
Price: $525,000
Living Area: 3,932 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Dec, 14, 2025
Price: $525,000
Living Area: 3,932 Sq. Ft.
EAST STREET
CHESTERTOWN, MD | Active Under Contract
Listed: Nov, 14, 2025
Price: $88,900
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Nov, 14, 2025
Price: $88,900
Living Area: 0 Sq. Ft.
112 SILVER HEEL DRIVE
CHESTERTOWN, MD | Closed
Listed: Nov, 03, 2025
Price: $369,900
Living Area: 2,615 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Nov, 03, 2025
Price: $369,900
Living Area: 2,615 Sq. Ft.
303 CEDAR STREET
CHESTERTOWN, MD | Closed
Listed: Dec, 18, 2025
Price: $333,900
Living Area: 2,577 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Dec, 18, 2025
Price: $333,900
Living Area: 2,577 Sq. Ft.
165 CHAR NOR MANOR BOULEVARD
CHESTERTOWN, MD | Closed
Listed: Jul, 06, 2025
Price: $409,900
Living Area: 2,258 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jul, 06, 2025
Price: $409,900
Living Area: 2,258 Sq. Ft.
104 IRIS ROAD
CHESTERTOWN, MD | Closed
Listed: Jan, 03, 2026
Price: $379,000
Living Area: 1,700 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 03, 2026
Price: $379,000
Living Area: 1,700 Sq. Ft.
404 SPRING ROAD
CHESTERTOWN, MD | Active Under Contract
Listed: Sep, 26, 2025
Price: $19,500
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Sep, 26, 2025
Price: $19,500
Living Area: 0 Sq. Ft.
10121 FAIRLEE ROAD
CHESTERTOWN, MD | Closed
Listed: Oct, 23, 2025
Price: $2,350,000
Living Area: 4,954 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Oct, 23, 2025
Price: $2,350,000
Living Area: 4,954 Sq. Ft.
8833 GEORGETOWN ROAD
CHESTERTOWN, MD | Closed
Listed: Sep, 30, 2025
Price: $364,000
Living Area: 1,625 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Sep, 30, 2025
Price: $364,000
Living Area: 1,625 Sq. Ft.
222 DUTCHESS ROAD
CHESTERTOWN, MD | Active
Listed: Oct, 10, 2025
Price: $320,000
Living Area: 1,096 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Oct, 10, 2025
Price: $320,000
Living Area: 1,096 Sq. Ft.
108 LITTLE HARBOR WAY
CHESTERTOWN, MD | Active
Listed: Nov, 13, 2025
Price: $635,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Nov, 13, 2025
Price: $635,000
Living Area: 0 Sq. Ft.
102 LITTLE HARBOR WAY
CHESTERTOWN, MD | Active
Listed: Dec, 04, 2025
Price: $839,500
Living Area: 1,964 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Dec, 04, 2025
Price: $839,500
Living Area: 1,964 Sq. Ft.
108 FLYING CLOUD DRIVE
CHESTERTOWN, MD | Pending
Listed: Nov, 19, 2025
Price: $364,900
Living Area: 1,936 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: Nov, 19, 2025
Price: $364,900
Living Area: 1,936 Sq. Ft.
100 ADELA WAY
CHESTERTOWN, MD | Active
Listed: Aug, 29, 2025
Price: $500,000
Living Area: 3,799 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Aug, 29, 2025
Price: $500,000
Living Area: 3,799 Sq. Ft.
234 N COLLEGE AVENUE
CHESTERTOWN, MD | Pending
Listed: Jul, 10, 2025
Price: $164,000
Living Area: 1,296 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: Jul, 10, 2025
Price: $164,000
Living Area: 1,296 Sq. Ft.
24775 LANGFORD ROAD
CHESTERTOWN, MD | Active
Listed: Dec, 27, 2025
Price: $319,900
Living Area: 1,008 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Dec, 27, 2025
Price: $319,900
Living Area: 1,008 Sq. Ft.
119 DARDEN ROAD
CHESTERTOWN, MD | Pending
Listed: Feb, 03, 2026
Price: $275,000
Living Area: 1,424 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: Feb, 03, 2026
Price: $275,000
Living Area: 1,424 Sq. Ft.
107 OAK LEAF DRIVE
CHESTERTOWN, MD | Coming Soon
Listed: Feb, 12, 2026
Price: $295,000
Living Area: 1,947 Sq. Ft.
CHESTERTOWN, MD | Coming Soon
Listed: Feb, 12, 2026
Price: $295,000
Living Area: 1,947 Sq. Ft.
127 WOOD DUCK LANE
CHESTERTOWN, MD | Active
Listed: Oct, 11, 2025
Price: $185,000
Living Area: 1,666 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Oct, 11, 2025
Price: $185,000
Living Area: 1,666 Sq. Ft.
CAULKS FIELD ROAD
CHESTERTOWN, MD | Closed
Listed: Jul, 02, 2023
Price: $28,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jul, 02, 2023
Price: $28,000
Living Area: 0 Sq. Ft.
515 WASHINGTON AVENUE
CHESTERTOWN, MD | Active
Listed: Aug, 21, 2024
Price: $899,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Aug, 21, 2024
Price: $899,000
Living Area: 0 Sq. Ft.
601 WASHINGTON AVENUE
CHESTERTOWN, MD | Active
Listed: Dec, 20, 2024
Price: $2,864
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Dec, 20, 2024
Price: $2,864
Living Area: 0 Sq. Ft.
7729 COUNTRY CLUB LANE
CHESTERTOWN, MD | Closed
Listed: Aug, 07, 2025
Price: $635,000
Living Area: 2,280 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Aug, 07, 2025
Price: $635,000
Living Area: 2,280 Sq. Ft.
136 TRUSLOW FARM LANE
CHESTERTOWN, MD | Closed
Listed: May, 29, 2025
Price: $575,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: May, 29, 2025
Price: $575,000
Living Area: 0 Sq. Ft.
24415 CHESTERTOWN ROAD
CHESTERTOWN, MD | Closed
Listed: Aug, 27, 2025
Price: $264,900
Living Area: 1,110 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Aug, 27, 2025
Price: $264,900
Living Area: 1,110 Sq. Ft.
124 CHAR NOR MANOR BOULEVARD
CHESTERTOWN, MD | Closed
Listed: Sep, 09, 2025
Price: $245,000
Living Area: 1,024 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Sep, 09, 2025
Price: $245,000
Living Area: 1,024 Sq. Ft.
23628 CANVASBACK ROAD
CHESTERTOWN, MD | Closed
Listed: Sep, 15, 2025
Price: $15,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Sep, 15, 2025
Price: $15,000
Living Area: 0 Sq. Ft.
105 PARMA ROAD
CHESTERTOWN, MD | Closed
Listed: Aug, 24, 2025
Price: $326,500
Living Area: 1,232 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Aug, 24, 2025
Price: $326,500
Living Area: 1,232 Sq. Ft.
10050 FORREST LANE
CHESTERTOWN, MD | Closed
Listed: Oct, 09, 2025
Price: $899,000
Living Area: 1,820 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Oct, 09, 2025
Price: $899,000
Living Area: 1,820 Sq. Ft.
349 & 351 HIGH STREET
CHESTERTOWN, MD | Active Under Contract
Listed: Apr, 19, 2024
Price: $395,000
Living Area: 3,664 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Apr, 19, 2024
Price: $395,000
Living Area: 3,664 Sq. Ft.
201 RADCLIFFE DRIVE
CHESTERTOWN, MD | Closed
Listed: Sep, 26, 2025
Price: $795,000
Living Area: 2,736 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Sep, 26, 2025
Price: $795,000
Living Area: 2,736 Sq. Ft.
8992 S BAYVIEW DRIVE
CHESTERTOWN, MD | Closed
Listed: Sep, 22, 2025
Price: $144,000
Living Area: 1,320 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Sep, 22, 2025
Price: $144,000
Living Area: 1,320 Sq. Ft.
JOHNSONTOWN ROAD
CHESTERTOWN, MD | Active Under Contract
Listed: Aug, 05, 2025
Price: $35,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Aug, 05, 2025
Price: $35,000
Living Area: 0 Sq. Ft.
Parcel BUCK NECK LDG ROAD
CHESTERTOWN, MD | Active
Listed: Apr, 15, 2025
Price: $10,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Apr, 15, 2025
Price: $10,000
Living Area: 0 Sq. Ft.
326 ROLPHS WHARF ROAD
CHESTERTOWN, MD | Closed
Listed: Mar, 21, 2022
Price: $119,000
Living Area: 1,568 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Mar, 21, 2022
Price: $119,000
Living Area: 1,568 Sq. Ft.
105 HIGH STREET
CHESTERTOWN, MD | Active
Listed: Nov, 07, 2025
Price: $1,395,500
Living Area: 3,243 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Nov, 07, 2025
Price: $1,395,500
Living Area: 3,243 Sq. Ft.
101 MORGNEC ROAD
CHESTERTOWN, MD | Active
Listed: Jan, 11, 2023
Price: $1,300
Living Area: 785 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jan, 11, 2023
Price: $1,300
Living Area: 785 Sq. Ft.
105 FLYING CLOUD DRIVE
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $335,000
Living Area: 1,849 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $335,000
Living Area: 1,849 Sq. Ft.
204 PINE COVE LANE
CHESTERTOWN, MD | Closed
Listed: Feb, 19, 2025
Price: $395,000
Living Area: 2,167 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Feb, 19, 2025
Price: $395,000
Living Area: 2,167 Sq. Ft.
130 SHEAFFER ROAD
CHESTERTOWN, MD | Closed
Listed: Mar, 30, 2025
Price: $434,500
Living Area: 1,766 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Mar, 30, 2025
Price: $434,500
Living Area: 1,766 Sq. Ft.
205 PRINCESS ANNE DRIVE
CHESTERTOWN, MD | Closed
Listed: Sep, 24, 2021
Price: $329,000
Living Area: 1,492 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Sep, 24, 2021
Price: $329,000
Living Area: 1,492 Sq. Ft.
120 SPEER ROAD
CHESTERTOWN, MD | Closed
Listed: Apr, 09, 2025
Price: $1,250,000
Living Area: 9,604 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Apr, 09, 2025
Price: $1,250,000
Living Area: 9,604 Sq. Ft.
421 CALVERT STREET
CHESTERTOWN, MD | Closed
Listed: Dec, 26, 2020
Price: $79,900
Living Area: 1,136 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Dec, 26, 2020
Price: $79,900
Living Area: 1,136 Sq. Ft.
214 DOUBLE CREEK ROAD
CHESTERTOWN, MD | Closed
Listed: Jun, 28, 2021
Price: $325,000
Living Area: 1,344 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 28, 2021
Price: $325,000
Living Area: 1,344 Sq. Ft.
23110 OLD FAIRLEE ROAD
CHESTERTOWN, MD | Active
Listed: Sep, 10, 2025
Price: $339,900
Living Area: 1,805 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Sep, 10, 2025
Price: $339,900
Living Area: 1,805 Sq. Ft.
CROMWELL CLARK ROAD
CHESTERTOWN, MD | Active
Listed: May, 07, 2025
Price: $3,000,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: May, 07, 2025
Price: $3,000,000
Living Area: 0 Sq. Ft.
411 GREENWOOD AVENUE
CHESTERTOWN, MD | Closed
Listed: Oct, 16, 2025
Price: $419,000
Living Area: 1,676 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Oct, 16, 2025
Price: $419,000
Living Area: 1,676 Sq. Ft.
26933 MALLARD ROAD
CHESTERTOWN, MD | Closed
Listed: Jul, 10, 2025
Price: $625,000
Living Area: 1,600 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jul, 10, 2025
Price: $625,000
Living Area: 1,600 Sq. Ft.
6746 QUAKER NECK ROAD
CHESTERTOWN, MD | Active
Listed: Jan, 02, 2026
Price: $445,000
Living Area: 3,371 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jan, 02, 2026
Price: $445,000
Living Area: 3,371 Sq. Ft.
6746 QUAKER ROAD
CHESTERTOWN, MD | Active
Listed: Jan, 02, 2026
Price: $445,000
Living Area: 3,371 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jan, 02, 2026
Price: $445,000
Living Area: 3,371 Sq. Ft.
860 & 870 HIGH STREET
CHESTERTOWN, MD | Closed
Listed: Apr, 22, 2024
Price: $375,000
Living Area: 16,977 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Apr, 22, 2024
Price: $375,000
Living Area: 16,977 Sq. Ft.
860 HIGH STREET STUDIO
CHESTERTOWN, MD | Closed
Listed: Nov, 06, 2024
Price: $1,700
Living Area: 16,977 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Nov, 06, 2024
Price: $1,700
Living Area: 16,977 Sq. Ft.
860 HIGH STREET CAFE
CHESTERTOWN, MD | Closed
Listed: Jun, 17, 2024
Price: $1,500
Living Area: 16,977 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 17, 2024
Price: $1,500
Living Area: 16,977 Sq. Ft.
201 N LYNCHBURG STREET
CHESTERTOWN, MD | Active
Listed: Jan, 22, 2026
Price: $795,000
Living Area: 3,527 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jan, 22, 2026
Price: $795,000
Living Area: 3,527 Sq. Ft.
203 HIGH STREET 2
CHESTERTOWN, MD | Active Under Contract
Listed: Jan, 05, 2026
Price: $1,600
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Jan, 05, 2026
Price: $1,600
Living Area: 0 Sq. Ft.
SHELDRAKE DRIVE
CHESTERTOWN, MD | Active
Listed: Aug, 08, 2022
Price: $15,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Aug, 08, 2022
Price: $15,000
Living Area: 0 Sq. Ft.
676 DEEP LANDING ROAD
CHESTERTOWN, MD | Closed
Listed: Nov, 28, 2025
Price: $315,000
Living Area: 1,468 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Nov, 28, 2025
Price: $315,000
Living Area: 1,468 Sq. Ft.
222 MOUNT VERNON AVENUE
CHESTERTOWN, MD | Active
Listed: Nov, 02, 2025
Price: $449,999
Living Area: 1,656 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Nov, 02, 2025
Price: $449,999
Living Area: 1,656 Sq. Ft.
7961 QUAKER NECK ROAD
CHESTERTOWN, MD | Closed
Listed: May, 10, 2025
Price: $1,550,000
Living Area: 4,167 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: May, 10, 2025
Price: $1,550,000
Living Area: 4,167 Sq. Ft.
611 CANNON STREET
CHESTERTOWN, MD | Closed
Listed: May, 26, 2023
Price: $240,000
Living Area: 920 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: May, 26, 2023
Price: $240,000
Living Area: 920 Sq. Ft.
2010 MCGINNES ROAD
CHESTERTOWN, MD | Closed
Listed: Sep, 23, 2025
Price: $359,900
Living Area: 1,253 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Sep, 23, 2025
Price: $359,900
Living Area: 1,253 Sq. Ft.
221 OLD BRIDGE ROAD
CHESTERTOWN, MD | Closed
Listed: Sep, 17, 2025
Price: $369,900
Living Area: 1,851 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Sep, 17, 2025
Price: $369,900
Living Area: 1,851 Sq. Ft.
10761 KASOTA ROAD
CHESTERTOWN, MD | Closed
Listed: Sep, 17, 2025
Price: $895,000
Living Area: 2,582 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Sep, 17, 2025
Price: $895,000
Living Area: 2,582 Sq. Ft.
23393 CACAWAY FARM LANE
CHESTERTOWN, MD | Closed
Listed: Sep, 29, 2024
Price: $1,195,000
Living Area: 4,446 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Sep, 29, 2024
Price: $1,195,000
Living Area: 4,446 Sq. Ft.
LOTS 253-254 CARIMON ROAD
CHESTERTOWN, MD | Active Under Contract
Listed: Dec, 17, 2024
Price: $9,500
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Dec, 17, 2024
Price: $9,500
Living Area: 0 Sq. Ft.
22681 WOOD YARD LANE
CHESTERTOWN, MD | Active
Listed: Jan, 05, 2026
Price: $15,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jan, 05, 2026
Price: $15,000
Living Area: 0 Sq. Ft.
315 CANNON STREET
CHESTERTOWN, MD | Active
Listed: Feb, 06, 2026
Price: $2,200
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Feb, 06, 2026
Price: $2,200
Living Area: 0 Sq. Ft.
#37 LANDING LANE
CHESTERTOWN, MD | Active
Listed: Dec, 04, 2025
Price: $765,900
Living Area: 1,964 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Dec, 04, 2025
Price: $765,900
Living Area: 1,964 Sq. Ft.
#36 LANDING LANE
CHESTERTOWN, MD | Active
Listed: Dec, 04, 2025
Price: $753,500
Living Area: 1,964 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Dec, 04, 2025
Price: $753,500
Living Area: 1,964 Sq. Ft.
10751 MILLBROOK DRIVE
CHESTERTOWN, MD | Active
Listed: Sep, 01, 2025
Price: $350,000
Living Area: 1,942 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Sep, 01, 2025
Price: $350,000
Living Area: 1,942 Sq. Ft.
ELM ROAD
CHESTERTOWN, MD | Active Under Contract
Listed: Mar, 11, 2024
Price: $20,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Mar, 11, 2024
Price: $20,000
Living Area: 0 Sq. Ft.
228 S WATER ST
CHESTERTOWN, MD | Active
Listed: Oct, 16, 2025
Price: $878,000
Living Area: 2,310 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Oct, 16, 2025
Price: $878,000
Living Area: 2,310 Sq. Ft.
104 LITTLE HARBOR WAY
CHESTERTOWN, MD | Active
Listed: Nov, 10, 2025
Price: $849,900
Living Area: 1,980 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Nov, 10, 2025
Price: $849,900
Living Area: 1,980 Sq. Ft.
200 HIGH STREET
CHESTERTOWN, MD | Active
Listed: Jan, 29, 2026
Price: $2,300,000
Living Area: 6,918 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jan, 29, 2026
Price: $2,300,000
Living Area: 6,918 Sq. Ft.
116 HARLAN LOOP
CHESTERTOWN, MD | Active
Listed: Aug, 22, 2025
Price: $509,000
Living Area: 4,067 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Aug, 22, 2025
Price: $509,000
Living Area: 4,067 Sq. Ft.
206 S WATER STREET
CHESTERTOWN, MD | Active
Listed: Jan, 14, 2026
Price: $549,000
Living Area: 2,008 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jan, 14, 2026
Price: $549,000
Living Area: 2,008 Sq. Ft.
118 LITTLE HARBOR WAY 202
CHESTERTOWN, MD | Active
Listed: Oct, 08, 2025
Price: $695,000
Living Area: 1,600 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Oct, 08, 2025
Price: $695,000
Living Area: 1,600 Sq. Ft.
104 LANDING LANE
CHESTERTOWN, MD | Active
Listed: Dec, 04, 2025
Price: $813,900
Living Area: 2,192 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Dec, 04, 2025
Price: $813,900
Living Area: 2,192 Sq. Ft.
