Listings in 21620 - QUEENANNES County, Maryland
Displaying 1 – 200 of 234 Real estate listings
624 HIGH STREET
CHESTERTOWN, MD | Active
Listed: Jun, 06, 2025
Price: $240,000
Living Area: 1,290 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jun, 06, 2025
Price: $240,000
Living Area: 1,290 Sq. Ft.
110 PHILOSOPHERS TERRACE
CHESTERTOWN, MD | Closed
Listed: Mar, 27, 2025
Price: $199,900
Living Area: 896 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Mar, 27, 2025
Price: $199,900
Living Area: 896 Sq. Ft.
6339 QUAKER NECK ROAD
CHESTERTOWN, MD | Closed
Listed: Jul, 10, 2025
Price: $2,500
Living Area: 1,908 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jul, 10, 2025
Price: $2,500
Living Area: 1,908 Sq. Ft.
10705 MILLBROOK DRIVE
CHESTERTOWN, MD | Closed
Listed: Jun, 20, 2025
Price: $399,900
Living Area: 2,106 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 20, 2025
Price: $399,900
Living Area: 2,106 Sq. Ft.
24576 LANGFORD ROAD
CHESTERTOWN, MD | Closed
Listed: Mar, 03, 2025
Price: $799,000
Living Area: 4,023 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Mar, 03, 2025
Price: $799,000
Living Area: 4,023 Sq. Ft.
114 CONLEY DRIVE
CHESTERTOWN, MD | Closed
Listed: Jun, 12, 2025
Price: $1,700
Living Area: 1,280 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 12, 2025
Price: $1,700
Living Area: 1,280 Sq. Ft.
MILLBROOK DRIVE
CHESTERTOWN, MD | Closed
Listed: May, 14, 2025
Price: $12,500
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: May, 14, 2025
Price: $12,500
Living Area: 0 Sq. Ft.
126 CHAR NOR MANOR BOULEVARD
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2025
Price: $224,999
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2025
Price: $224,999
Living Area: 0 Sq. Ft.
22681 WOOD YARD LANE
CHESTERTOWN, MD | Active
Listed: May, 01, 2025
Price: $15,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: May, 01, 2025
Price: $15,000
Living Area: 0 Sq. Ft.
201 N LYNCHBURG STREET
CHESTERTOWN, MD | Active
Listed: Jun, 09, 2025
Price: $850,000
Living Area: 3,527 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jun, 09, 2025
Price: $850,000
Living Area: 3,527 Sq. Ft.
11040 KYLIE LANE
CHESTERTOWN, MD | Active
Listed: May, 16, 2025
Price: $649,000
Living Area: 3,684 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: May, 16, 2025
Price: $649,000
Living Area: 3,684 Sq. Ft.
7483 SHORTALL STREET
CHESTERTOWN, MD | Pending
Listed: Aug, 28, 2025
Price: $290,000
Living Area: 1,232 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: Aug, 28, 2025
Price: $290,000
Living Area: 1,232 Sq. Ft.
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.
101 BIRCH RUN ROAD
CHESTERTOWN, MD | Active
Listed: Oct, 12, 2025
Price: $499,999
Living Area: 1,961 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Oct, 12, 2025
Price: $499,999
Living Area: 1,961 Sq. Ft.
206 S WATER STREET
CHESTERTOWN, MD | Active
Listed: Oct, 22, 2025
Price: $619,000
Living Area: 2,008 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Oct, 22, 2025
Price: $619,000
Living Area: 2,008 Sq. Ft.
8293 BRICES MILL ROAD
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2025
Price: $799,999
Living Area: 2,836 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2025
Price: $799,999
Living Area: 2,836 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.
204 ROLLING ROAD
CHESTERTOWN, MD | Coming Soon
Listed: Nov, 07, 2025
Price: $370,000
Living Area: 2,296 Sq. Ft.
CHESTERTOWN, MD | Coming Soon
Listed: Nov, 07, 2025
Price: $370,000
Living Area: 2,296 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.
10230 JOHN CARVILL ROAD
CHESTERTOWN, MD | Active
Listed: Nov, 03, 2025
Price: $750,000
Living Area: 2,350 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Nov, 03, 2025
Price: $750,000
Living Area: 2,350 Sq. Ft.
109 WILTON ROAD
CHESTERTOWN, MD | Active
Listed: Jan, 20, 2025
Price: $344,900
Living Area: 1,392 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jan, 20, 2025
Price: $344,900
Living Area: 1,392 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.
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.
5700 JOHNSONTOWN ROAD
CHESTERTOWN, MD | Active
Listed: Aug, 10, 2025
Price: $110,000
Living Area: 1,144 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Aug, 10, 2025
Price: $110,000
Living Area: 1,144 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.
206 VALLEY
CHESTERTOWN, MD | Pending
Listed: Sep, 30, 2025
Price: $615,000
Living Area: 2,869 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: Sep, 30, 2025
Price: $615,000
Living Area: 2,869 Sq. Ft.
907 N MEADOWVIEW DRIVE
CHESTERTOWN, MD | Active Under Contract
Listed: Aug, 04, 2025
Price: $410,000
Living Area: 1,842 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Aug, 04, 2025
Price: $410,000
Living Area: 1,842 Sq. Ft.
7653 BROAD NECK ROAD
CHESTERTOWN, MD | Active Under Contract
Listed: Sep, 25, 2025
Price: $375,000
Living Area: 1,790 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Sep, 25, 2025
Price: $375,000
Living Area: 1,790 Sq. Ft.
201 BIRCH RUN ROAD
CHESTERTOWN, MD | Active
Listed: Jun, 30, 2025
Price: $470,000
Living Area: 1,588 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jun, 30, 2025
Price: $470,000
Living Area: 1,588 Sq. Ft.
7521 PINE AVENUE
CHESTERTOWN, MD | Coming Soon
Listed: Nov, 17, 2025
Price: $265,000
Living Area: 1,040 Sq. Ft.
CHESTERTOWN, MD | Coming Soon
Listed: Nov, 17, 2025
Price: $265,000
Living Area: 1,040 Sq. Ft.
100 METCALF ROAD
CHESTERTOWN, MD | Active
Listed: Aug, 28, 2025
Price: $245,000
Living Area: 1,140 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Aug, 28, 2025
Price: $245,000
Living Area: 1,140 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.
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.
21111 TEXAS AVENUE
CHESTERTOWN, MD | Coming Soon
Listed: Nov, 20, 2025
Price: $370,000
Living Area: 1,680 Sq. Ft.
CHESTERTOWN, MD | Coming Soon
Listed: Nov, 20, 2025
Price: $370,000
Living Area: 1,680 Sq. Ft.
112 METCALF ROAD
CHESTERTOWN, MD | Active
Listed: Jul, 28, 2025
Price: $249,950
Living Area: 1,280 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jul, 28, 2025
Price: $249,950
Living Area: 1,280 Sq. Ft.
216 BLAKEFIELD DRIVE
CHESTERTOWN, MD | Active
Listed: Nov, 02, 2025
Price: $579,000
Living Area: 2,400 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Nov, 02, 2025
Price: $579,000
Living Area: 2,400 Sq. Ft.
23069 RALEIGH ROAD
CHESTERTOWN, MD | Active
Listed: Jun, 25, 2025
Price: $175,000
Living Area: 1,160 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jun, 25, 2025
Price: $175,000
Living Area: 1,160 Sq. Ft.
118 TUXEDO ROAD
CHESTERTOWN, MD | Closed
Listed: Mar, 07, 2025
Price: $274,000
Living Area: 1,056 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Mar, 07, 2025
Price: $274,000
Living Area: 1,056 Sq. Ft.
21363 INDIANA AVENUE
CHESTERTOWN, MD | Closed
Listed: Jun, 10, 2025
Price: $299,900
Living Area: 896 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 10, 2025
Price: $299,900
Living Area: 896 Sq. Ft.
128 N QUEEN STREET 3
CHESTERTOWN, MD | Closed
Listed: Jul, 18, 2025
Price: $1,450
Living Area: 900 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jul, 18, 2025
Price: $1,450
Living Area: 900 Sq. Ft.
114 RYAN COURT
CHESTERTOWN, MD | Closed
Listed: Apr, 24, 2025
Price: $399,000
Living Area: 1,496 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Apr, 24, 2025
Price: $399,000
Living Area: 1,496 Sq. Ft.
10578 TONOPAH ROAD
CHESTERTOWN, MD | Closed
Listed: Jun, 19, 2025
Price: $335,000
Living Area: 1,500 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 19, 2025
Price: $335,000
Living Area: 1,500 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.
300 HICKORY LANE
CHESTERTOWN, MD | Active
Listed: Jun, 19, 2025
Price: $1,198,000
Living Area: 3,640 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jun, 19, 2025
Price: $1,198,000
Living Area: 3,640 Sq. Ft.
7425 WILKINS LANE
CHESTERTOWN, MD | Closed
Listed: Jul, 04, 2025
Price: $320,000
Living Area: 1,341 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jul, 04, 2025
Price: $320,000
Living Area: 1,341 Sq. Ft.
24543 CHESTERTOWN ROAD
CHESTERTOWN, MD | Pending
Listed: Jan, 08, 2025
Price: $425,000
Living Area: 3,280 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: Jan, 08, 2025
Price: $425,000
Living Area: 3,280 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.
10670 TINTAH ROAD
CHESTERTOWN, MD | Closed
Listed: Jun, 05, 2025
Price: $315,000
Living Area: 1,404 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 05, 2025
Price: $315,000
Living Area: 1,404 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.
114 DARDEN ROAD
CHESTERTOWN, MD | Closed
Listed: Mar, 31, 2025
Price: $269,900
Living Area: 1,056 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Mar, 31, 2025
Price: $269,900
Living Area: 1,056 Sq. Ft.
304 HILLTOP LANE
CHESTERTOWN, MD | Closed
Listed: Jul, 17, 2025
Price: $209,900
Living Area: 1,199 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jul, 17, 2025
Price: $209,900
Living Area: 1,199 Sq. Ft.
8978 ORCHARD DRIVE
CHESTERTOWN, MD | Closed
Listed: Aug, 19, 2025
Price: $675,000
Living Area: 3,820 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Aug, 19, 2025
Price: $675,000
Living Area: 3,820 Sq. Ft.
104 MAPLE AVENUE
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2025
Price: $725,000
Living Area: 5,472 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2025
Price: $725,000
Living Area: 5,472 Sq. Ft.
104 MAPLE AVENUE
CHESTERTOWN, MD | Closed
Listed: Aug, 18, 2025
Price: $2,175
Living Area: 1,200 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Aug, 18, 2025
Price: $2,175
Living Area: 1,200 Sq. Ft.
127 CHAR NOR MANOR BOULEVARD
CHESTERTOWN, MD | Closed
Listed: Aug, 28, 2025
Price: $329,900
Living Area: 832 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Aug, 28, 2025
Price: $329,900
Living Area: 832 Sq. Ft.
23620 LANDS END ROAD
CHESTERTOWN, MD | Pending
Listed: May, 21, 2025
Price: $4,850,000
Living Area: 9,852 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: May, 21, 2025
Price: $4,850,000
Living Area: 9,852 Sq. Ft.
23065 OLD FAIRLEE ROAD
CHESTERTOWN, MD | Closed
Listed: Sep, 19, 2025
Price: $149,000
Living Area: 1,176 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Sep, 19, 2025
Price: $149,000
Living Area: 1,176 Sq. Ft.
143 CHAR NOR MANOR BOULEVARD
CHESTERTOWN, MD | Closed
Listed: Aug, 04, 2025
Price: $868,000
Living Area: 2,073 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Aug, 04, 2025
Price: $868,000
Living Area: 2,073 Sq. Ft.
423 CALVERT STREET
CHESTERTOWN, MD | Active
Listed: Sep, 26, 2025
Price: $165,000
Living Area: 1,136 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Sep, 26, 2025
Price: $165,000
Living Area: 1,136 Sq. Ft.
26889 MORGNEC ROAD
CHESTERTOWN, MD | Closed
Listed: Jun, 10, 2025
Price: $699,000
Living Area: 1,966 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 10, 2025
Price: $699,000
Living Area: 1,966 Sq. Ft.
10165 JOHN CARVILL ROAD
CHESTERTOWN, MD | Closed
Listed: Aug, 09, 2025
Price: $549,000
Living Area: 2,774 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Aug, 09, 2025
Price: $549,000
Living Area: 2,774 Sq. Ft.
134 CHAR NOR MANOR BOULEVARD
CHESTERTOWN, MD | Active
Listed: Jul, 09, 2025
Price: $285,000
Living Area: 1,128 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jul, 09, 2025
Price: $285,000
Living Area: 1,128 Sq. Ft.
132 PROSPECT STREET
CHESTERTOWN, MD | Active
Listed: Jul, 14, 2025
Price: $62,400
Living Area: 910 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jul, 14, 2025
Price: $62,400
Living Area: 910 Sq. Ft.
221 RICHARD DRIVE
CHESTERTOWN, MD | Closed
Listed: Sep, 17, 2025
Price: $385,000
Living Area: 1,711 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Sep, 17, 2025
Price: $385,000
Living Area: 1,711 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.
LOT 24 & 25 BUCK NECK ROAD
CHESTERTOWN, MD | Active Under Contract
Listed: Feb, 05, 2025
Price: $8,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Feb, 05, 2025
Price: $8,000
Living Area: 0 Sq. Ft.
110 TUXEDO ROAD
CHESTERTOWN, MD | Active
Listed: Sep, 09, 2025
Price: $269,000
Living Area: 1,664 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Sep, 09, 2025
Price: $269,000
Living Area: 1,664 Sq. Ft.
7844 CHESTER COURT
CHESTERTOWN, MD | Active
Listed: Oct, 23, 2025
Price: $770,000
Living Area: 3,248 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Oct, 23, 2025
Price: $770,000
Living Area: 3,248 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.
107 MALONE AVENUE
CHESTERTOWN, MD | Active
Listed: Oct, 01, 2025
Price: $290,000
Living Area: 1,200 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Oct, 01, 2025
Price: $290,000
Living Area: 1,200 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.
GEORGETOWN RD & CROSS ROAD
CHESTERTOWN, MD | Active
Listed: Apr, 16, 2025
Price: $120,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Apr, 16, 2025
Price: $120,000
Living Area: 0 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.
CAULKS FIELD ROAD
CHESTERTOWN, MD | Active
Listed: Jul, 02, 2023
Price: $28,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jul, 02, 2023
Price: $28,000
Living Area: 0 Sq. Ft.
5117 DEEP POINT DRIVE A
CHESTERTOWN, MD | Closed
Listed: Jun, 24, 2025
Price: $3,200
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 24, 2025
Price: $3,200
Living Area: 0 Sq. Ft.
24095 CHESTERTOWN ROAD
CHESTERTOWN, MD | Closed
Listed: Jun, 10, 2025
Price: $310,000
Living Area: 1,104 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 10, 2025
Price: $310,000
Living Area: 1,104 Sq. Ft.
206 SILVER HEEL DRIVE
CHESTERTOWN, MD | Closed
Listed: Jul, 07, 2025
Price: $375,000
Living Area: 2,302 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jul, 07, 2025
Price: $375,000
Living Area: 2,302 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.
119 DARDEN ROAD
CHESTERTOWN, MD | Active
Listed: Sep, 12, 2025
Price: $315,000
Living Area: 1,424 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Sep, 12, 2025
Price: $315,000
Living Area: 1,424 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.
128 N QUEEN STREET 4
CHESTERTOWN, MD | Closed
Listed: May, 28, 2025
Price: $1,450
Living Area: 1,455 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: May, 28, 2025
Price: $1,450
Living Area: 1,455 Sq. Ft.
22570 BAY SHORE ROAD
CHESTERTOWN, MD | Closed
Listed: Jun, 07, 2025
Price: $435,000
Living Area: 1,788 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 07, 2025
Price: $435,000
Living Area: 1,788 Sq. Ft.
23370 LOVELY LANE
CHESTERTOWN, MD | Closed
Listed: Jul, 29, 2025
Price: $309,000
Living Area: 1,680 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jul, 29, 2025
Price: $309,000
Living Area: 1,680 Sq. Ft.
206 BARROLL DRIVE
CHESTERTOWN, MD | Closed
Listed: Jun, 16, 2025
Price: $438,000
Living Area: 1,820 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 16, 2025
Price: $438,000
Living Area: 1,820 Sq. Ft.
21317 PERSIMMON DRIVE
CHESTERTOWN, MD | Closed
Listed: Jun, 20, 2025
Price: $195,000
Living Area: 1,269 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 20, 2025
Price: $195,000
Living Area: 1,269 Sq. Ft.
110 FLYING CLOUD COURT
CHESTERTOWN, MD | Closed
Listed: Feb, 22, 2025
Price: $334,900
Living Area: 1,856 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Feb, 22, 2025
Price: $334,900
Living Area: 1,856 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.
224 VALLEY ROAD
CHESTERTOWN, MD | Closed
Listed: Aug, 05, 2025
Price: $450,000
Living Area: 1,886 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Aug, 05, 2025
Price: $450,000
Living Area: 1,886 Sq. Ft.
119 HIGH STREET
CHESTERTOWN, MD | Pending
Listed: Sep, 28, 2025
Price: $1,250,000
Living Area: 4,409 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: Sep, 28, 2025
Price: $1,250,000
Living Area: 4,409 Sq. Ft.
10121 FAIRLEE ROAD
CHESTERTOWN, MD | Active
Listed: Oct, 28, 2025
Price: $2,350,000
Living Area: 4,954 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Oct, 28, 2025
Price: $2,350,000
Living Area: 4,954 Sq. Ft.
10121 FAIRLEE ROAD
CHESTERTOWN, MD | Active
Listed: Oct, 23, 2025
Price: $2,350,000
Living Area: 4,954 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Oct, 23, 2025
Price: $2,350,000
Living Area: 4,954 Sq. Ft.
165 CHAR NOR MANOR BOULEVARD
CHESTERTOWN, MD | Active
Listed: Jul, 06, 2025
Price: $429,999
Living Area: 2,258 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jul, 06, 2025
Price: $429,999
Living Area: 2,258 Sq. Ft.
CHURCH HILL ( LOT 2) ROAD
CHESTERTOWN, MD | Active Under Contract
Listed: Jul, 10, 2025
Price: $165,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Jul, 10, 2025
Price: $165,000
Living Area: 0 Sq. Ft.
8951 ORCHARD DRIVE
CHESTERTOWN, MD | Pending
Listed: Oct, 21, 2025
Price: $695,000
Living Area: 3,735 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: Oct, 21, 2025
Price: $695,000
Living Area: 3,735 Sq. Ft.
118 LITTLE HARBOR WAY 201
CHESTERTOWN, MD | Active
Listed: Sep, 14, 2025
Price: $675,000
Living Area: 1,550 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Sep, 14, 2025
Price: $675,000
Living Area: 1,550 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.
101 METCALF ROAD
CHESTERTOWN, MD | Pending
Listed: Nov, 04, 2025
Price: $264,900
Living Area: 1,280 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: Nov, 04, 2025
Price: $264,900
Living Area: 1,280 Sq. Ft.
304 HADAWAY DRIVE
CHESTERTOWN, MD | Active
Listed: Nov, 01, 2025
Price: $425,000
Living Area: 1,325 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Nov, 01, 2025
Price: $425,000
Living Area: 1,325 Sq. Ft.
112 SILVER HEEL DRIVE
CHESTERTOWN, MD | Active
Listed: Nov, 03, 2025
Price: $369,900
Living Area: 2,615 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Nov, 03, 2025
Price: $369,900
Living Area: 2,615 Sq. Ft.
212 LANDING LANE
CHESTERTOWN, MD | Active Under Contract
Listed: Feb, 04, 2025
Price: $759,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Feb, 04, 2025
Price: $759,000
Living Area: 0 Sq. Ft.
8833 GEORGETOWN ROAD
CHESTERTOWN, MD | Active
Listed: Sep, 30, 2025
Price: $314,000
Living Area: 1,625 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Sep, 30, 2025
Price: $314,000
Living Area: 1,625 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.
108 S KENT STREET
CHESTERTOWN, MD | Active
Listed: Jul, 26, 2025
Price: $315,000
Living Area: 936 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jul, 26, 2025
Price: $315,000
Living Area: 936 Sq. Ft.
303 E CAMPUS AVENUE
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2025
Price: $280,000
Living Area: 1,532 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2025
Price: $280,000
Living Area: 1,532 Sq. Ft.
303 E CAMPUS AVENUE
CHESTERTOWN, MD | Active Under Contract
Listed: Oct, 25, 2025
Price: $363,000
Living Area: 1,532 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Oct, 25, 2025
Price: $363,000
Living Area: 1,532 Sq. Ft.
212 CENTRAL DRIVE
CHESTERTOWN, MD | Closed
Listed: Jun, 05, 2025
Price: $294,000
Living Area: 1,104 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 05, 2025
Price: $294,000
Living Area: 1,104 Sq. Ft.
304 HADAWAY DRIVE
CHESTERTOWN, MD | Closed
Listed: Jul, 12, 2025
Price: $249,900
Living Area: 1,325 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jul, 12, 2025
Price: $249,900
Living Area: 1,325 Sq. Ft.
209 RIVER ROAD
CHESTERTOWN, MD | Closed
Listed: Jun, 12, 2025
Price: $135,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 12, 2025
Price: $135,000
Living Area: 0 Sq. Ft.
10715 KASOTA ROAD
CHESTERTOWN, MD | Closed
Listed: Jun, 23, 2025
Price: $975,000
Living Area: 3,401 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 23, 2025
Price: $975,000
Living Area: 3,401 Sq. Ft.
200 WASHINGTON AVENUE
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2025
Price: $495,000
Living Area: 2,915 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2025
Price: $495,000
Living Area: 2,915 Sq. Ft.
Lot 9 PRESTWICK DRIVE
CHESTERTOWN, MD | Active
Listed: May, 05, 2024
Price: $185,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: May, 05, 2024
Price: $185,000
Living Area: 0 Sq. Ft.
21217 TEXAS AVENUE
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2025
Price: $99,900
Living Area: 912 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2025
Price: $99,900
Living Area: 912 Sq. Ft.
9190 N BAYVIEW AVENUE
CHESTERTOWN, MD | Closed
Listed: Aug, 01, 2025
Price: $319,500
Living Area: 1,160 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Aug, 01, 2025
Price: $319,500
Living Area: 1,160 Sq. Ft.
209 RIVERSHORE ROAD
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2025
Price: $549,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2025
Price: $549,000
Living Area: 0 Sq. Ft.
300 HILLTOP LANE
CHESTERTOWN, MD | Closed
Listed: Mar, 29, 2025
Price: $220,000
Living Area: 1,200 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Mar, 29, 2025
Price: $220,000
Living Area: 1,200 Sq. Ft.
9194 N BAYVIEW AVENUE
CHESTERTOWN, MD | Closed
Listed: Aug, 03, 2025
Price: $698,000
Living Area: 1,460 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Aug, 03, 2025
Price: $698,000
Living Area: 1,460 Sq. Ft.
127 WOOD DUCK LANE
CHESTERTOWN, MD | Active
Listed: Oct, 11, 2025
Price: $215,000
Living Area: 1,666 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Oct, 11, 2025
Price: $215,000
Living Area: 1,666 Sq. Ft.
234 N COLLEGE AVENUE
CHESTERTOWN, MD | Active Under Contract
Listed: Jul, 10, 2025
Price: $164,000
Living Area: 1,296 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Jul, 10, 2025
Price: $164,000
Living Area: 1,296 Sq. Ft.
404 SPRING ROAD
CHESTERTOWN, MD | Active
Listed: Sep, 26, 2025
Price: $19,500
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Sep, 26, 2025
Price: $19,500
Living Area: 0 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.
600 ROSIN DRIVE
CHESTERTOWN, MD | Active Under Contract
Listed: Oct, 02, 2025
Price: $415,000
Living Area: 1,300 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Oct, 02, 2025
Price: $415,000
Living Area: 1,300 Sq. Ft.
100 ADELA WAY
CHESTERTOWN, MD | Active
Listed: Aug, 29, 2025
Price: $515,000
Living Area: 3,799 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Aug, 29, 2025
Price: $515,000
Living Area: 3,799 Sq. Ft.
302 ROSIN DRIVE
CHESTERTOWN, MD | Active Under Contract
Listed: Oct, 26, 2025
Price: $574,000
Living Area: 3,877 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Oct, 26, 2025
Price: $574,000
Living Area: 3,877 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.
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.
10781 FERMOY ROAD
CHESTERTOWN, MD | Active
Listed: Oct, 23, 2025
Price: $449,900
Living Area: 2,160 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Oct, 23, 2025
Price: $449,900
Living Area: 2,160 Sq. Ft.
517 HIGH STREET
CHESTERTOWN, MD | Active Under Contract
Listed: Sep, 25, 2025
Price: $389,900
Living Area: 1,728 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Sep, 25, 2025
Price: $389,900
Living Area: 1,728 Sq. Ft.
492 PEAR TREE POINT ROAD
CHESTERTOWN, MD | Active Under Contract
Listed: Oct, 07, 2025
Price: $875,000
Living Area: 3,720 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Oct, 07, 2025
Price: $875,000
Living Area: 3,720 Sq. Ft.
109 S COLLEGE AVENUE
CHESTERTOWN, MD | Active
Listed: Oct, 25, 2025
Price: $449,900
Living Area: 1,216 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Oct, 25, 2025
Price: $449,900
Living Area: 1,216 Sq. Ft.
206 CANNON STREET
CHESTERTOWN, MD | Pending
Listed: Feb, 23, 2024
Price: $1,150,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: Feb, 23, 2024
Price: $1,150,000
Living Area: 0 Sq. Ft.
206 CANNON STREET
CHESTERTOWN, MD | Pending
Listed: Feb, 23, 2024
Price: $1,150,000
Living Area: 1,588 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: Feb, 23, 2024
Price: $1,150,000
Living Area: 1,588 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.
108 FLYING CLOUD DRIVE
CHESTERTOWN, MD | Active
Listed: Nov, 19, 2025
Price: $375,000
Living Area: 1,936 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Nov, 19, 2025
Price: $375,000
Living Area: 1,936 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.
200 WASHINGTON AVENUE
CHESTERTOWN, MD | Active
Listed: Aug, 05, 2025
Price: $695,000
Living Area: 2,917 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Aug, 05, 2025
Price: $695,000
Living Area: 2,917 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.
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.
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.
120 SPEER ROAD
CHESTERTOWN, MD | Active
Listed: Apr, 09, 2025
Price: $1,250,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Apr, 09, 2025
Price: $1,250,000
Living Area: 0 Sq. Ft.
10575 HYALA COURT
CHESTERTOWN, MD | Closed
Listed: Jun, 11, 2025
Price: $359,000
Living Area: 1,978 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 11, 2025
Price: $359,000
Living Area: 1,978 Sq. Ft.
7682 WATERVIEW LANE
CHESTERTOWN, MD | Closed
Listed: Jul, 07, 2025
Price: $655,000
Living Area: 2,240 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jul, 07, 2025
Price: $655,000
Living Area: 2,240 Sq. Ft.
JOHNSONTOWN ROAD
CHESTERTOWN, MD | Active
Listed: Aug, 05, 2025
Price: $35,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Aug, 05, 2025
Price: $35,000
Living Area: 0 Sq. Ft.
329 HIGH STREET
CHESTERTOWN, MD | Active
Listed: May, 09, 2025
Price: $1,250,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: May, 09, 2025
Price: $1,250,000
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.
10175 JOHN CARVILL ROAD
CHESTERTOWN, MD | Closed
Listed: May, 13, 2025
Price: $625,000
Living Area: 3,155 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: May, 13, 2025
Price: $625,000
Living Area: 3,155 Sq. Ft.
21082 WYOMING AVENUE
CHESTERTOWN, MD | Closed
Listed: Apr, 30, 2025
Price: $1,550,000
Living Area: 2,699 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Apr, 30, 2025
Price: $1,550,000
Living Area: 2,699 Sq. Ft.
209 RIVERSHORE ROAD
CHESTERTOWN, MD | Closed
Listed: Jul, 02, 2025
Price: $815,000
Living Area: 1,401 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jul, 02, 2025
Price: $815,000
Living Area: 1,401 Sq. Ft.
925 ROUND TOP ROAD
CHESTERTOWN, MD | Closed
Listed: Jun, 10, 2025
Price: $300,000
Living Area: 1,056 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 10, 2025
Price: $300,000
Living Area: 1,056 Sq. Ft.
205 PINE STREET
CHESTERTOWN, MD | Closed
Listed: Jul, 25, 2025
Price: $325,000
Living Area: 2,212 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jul, 25, 2025
Price: $325,000
Living Area: 2,212 Sq. Ft.
515 N KENT STREET
CHESTERTOWN, MD | Active
Listed: Aug, 24, 2025
Price: $499,900
Living Area: 2,220 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Aug, 24, 2025
Price: $499,900
Living Area: 2,220 Sq. Ft.
200 FEY ROAD
CHESTERTOWN, MD | Closed
Listed: Aug, 21, 2025
Price: $374,900
Living Area: 1,572 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Aug, 21, 2025
Price: $374,900
Living Area: 1,572 Sq. Ft.
103 LANDING LANE
CHESTERTOWN, MD | Active
Listed: Sep, 10, 2025
Price: $559,000
Living Area: 2,100 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Sep, 10, 2025
Price: $559,000
Living Area: 2,100 Sq. Ft.
111 CEE JAY ROAD
CHESTERTOWN, MD | Closed
Listed: Sep, 04, 2025
Price: $359,900
Living Area: 1,400 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Sep, 04, 2025
Price: $359,900
Living Area: 1,400 Sq. Ft.
116 HARLAN LOOP
CHESTERTOWN, MD | Active
Listed: Aug, 22, 2025
Price: $519,000
Living Area: 4,067 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Aug, 22, 2025
Price: $519,000
Living Area: 4,067 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.
103 METCALF RD
CHESTERTOWN, MD | Active
Listed: Sep, 12, 2025
Price: $259,900
Living Area: 1,280 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Sep, 12, 2025
Price: $259,900
Living Area: 1,280 Sq. Ft.
23043 BAY SHORE SPUR
CHESTERTOWN, MD | Active
Listed: Aug, 28, 2025
Price: $325,000
Living Area: 2,630 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Aug, 28, 2025
Price: $325,000
Living Area: 2,630 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.
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.
8750 GEORGETOWN ROAD
CHESTERTOWN, MD | Active
Listed: Oct, 16, 2025
Price: $339,000
Living Area: 1,900 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Oct, 16, 2025
Price: $339,000
Living Area: 1,900 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.
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.
411 GREENWOOD AVENUE
CHESTERTOWN, MD | Pending
Listed: Oct, 16, 2025
Price: $419,000
Living Area: 1,676 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: Oct, 16, 2025
Price: $419,000
Living Area: 1,676 Sq. Ft.
121 PRIMROSE ROAD
CHESTERTOWN, MD | Active
Listed: Nov, 12, 2025
Price: $399,000
Living Area: 2,034 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Nov, 12, 2025
Price: $399,000
Living Area: 2,034 Sq. Ft.
222 MOUNT VERNON AVENUE
CHESTERTOWN, MD | Active
Listed: Nov, 02, 2025
Price: $470,000
Living Area: 1,656 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Nov, 02, 2025
Price: $470,000
Living Area: 1,656 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.
26933 MALLARD ROAD
CHESTERTOWN, MD | Pending
Listed: Jul, 10, 2025
Price: $625,000
Living Area: 1,600 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: Jul, 10, 2025
Price: $625,000
Living Area: 1,600 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.
118 LITTLE HARBOR WAY 202
CHESTERTOWN, MD | Coming Soon
Listed: Oct, 08, 2025
Price: $695,000
Living Area: 1,600 Sq. Ft.
CHESTERTOWN, MD | Coming Soon
Listed: Oct, 08, 2025
Price: $695,000
Living Area: 1,600 Sq. Ft.
