Listings in 21620 - KENT County, Maryland
Displaying 1 – 200 of 248 Real estate listings
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.
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.
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.
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.
216 BLAKEFIELD DRIVE
CHESTERTOWN, MD | Active Under Contract
Listed: Nov, 02, 2025
Price: $559,000
Living Area: 2,400 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Nov, 02, 2025
Price: $559,000
Living Area: 2,400 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.
4671 CLIFFS CITY ROAD
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $800,000
Living Area: 1,783 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $800,000
Living Area: 1,783 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.
213 CENTRAL DRIVE
CHESTERTOWN, MD | Closed
Listed: Dec, 01, 2025
Price: $314,900
Living Area: 1,232 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Dec, 01, 2025
Price: $314,900
Living Area: 1,232 Sq. Ft.
23069 RALEIGH ROAD
CHESTERTOWN, MD | Closed
Listed: Jun, 25, 2025
Price: $175,000
Living Area: 1,160 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 25, 2025
Price: $175,000
Living Area: 1,160 Sq. Ft.
112 METCALF ROAD
CHESTERTOWN, MD | Active Under Contract
Listed: Jan, 24, 2026
Price: $249,500
Living Area: 1,280 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Jan, 24, 2026
Price: $249,500
Living Area: 1,280 Sq. Ft.
148 STEP ROAD
CHESTERTOWN, MD | Active Under Contract
Listed: Feb, 24, 2026
Price: $369,000
Living Area: 1,400 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Feb, 24, 2026
Price: $369,000
Living Area: 1,400 Sq. Ft.
109 WILTON ROAD
CHESTERTOWN, MD | Active
Listed: Mar, 09, 2026
Price: $344,900
Living Area: 1,392 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 09, 2026
Price: $344,900
Living Area: 1,392 Sq. Ft.
108 PRIMROSE ROAD
CHESTERTOWN, MD | Closed
Listed: Mar, 26, 2026
Price: $2,500
Living Area: 1,722 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Mar, 26, 2026
Price: $2,500
Living Area: 1,722 Sq. Ft.
106 QUEEN STREET S
CHESTERTOWN, MD | Active
Listed: Mar, 19, 2026
Price: $865,000
Living Area: 2,472 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 19, 2026
Price: $865,000
Living Area: 2,472 Sq. Ft.
OLD MORGNEC ROAD
CHESTERTOWN, MD | Active Under Contract
Listed: Mar, 25, 2025
Price: $59,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Mar, 25, 2025
Price: $59,000
Living Area: 0 Sq. Ft.
129 PARMA ROAD
CHESTERTOWN, MD | Closed
Listed: Jan, 09, 2026
Price: $330,000
Living Area: 1,170 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 09, 2026
Price: $330,000
Living Area: 1,170 Sq. Ft.
21324 PERSIMMON DRIVE
CHESTERTOWN, MD | Active
Listed: Mar, 04, 2026
Price: $136,800
Living Area: 1,232 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 04, 2026
Price: $136,800
Living Area: 1,232 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.
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.
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.
#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.
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.
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.
141 PROSPECT STREET
CHESTERTOWN, MD | Closed
Listed: Jan, 06, 2026
Price: $165,000
Living Area: 1,156 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 06, 2026
Price: $165,000
Living Area: 1,156 Sq. Ft.
109 WATER STREET
CHESTERTOWN, MD | Closed
Listed: Jan, 17, 2026
Price: $650,000
Living Area: 2,064 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 17, 2026
Price: $650,000
Living Area: 2,064 Sq. Ft.
423 CALVERT STREET
CHESTERTOWN, MD | Closed
Listed: Sep, 26, 2025
Price: $135,000
Living Area: 1,136 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Sep, 26, 2025
Price: $135,000
Living Area: 1,136 Sq. Ft.
21111 TEXAS AVENUE
CHESTERTOWN, MD | Closed
Listed: Nov, 20, 2025
Price: $370,000
Living Area: 1,680 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Nov, 20, 2025
Price: $370,000
Living Area: 1,680 Sq. Ft.
HOFFECKER ROAD
CHESTERTOWN, MD | Closed
Listed: Jan, 15, 2026
Price: $212,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 15, 2026
Price: $212,000
Living Area: 0 Sq. Ft.
104 GARLAND AVENUE
CHESTERTOWN, MD | Active Under Contract
Listed: Feb, 25, 2026
Price: $440,000
Living Area: 1,734 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Feb, 25, 2026
Price: $440,000
Living Area: 1,734 Sq. Ft.
513 ROUND TOP ROAD
CHESTERTOWN, MD | Active Under Contract
Listed: Mar, 11, 2026
Price: $225,000
Living Area: 1,248 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Mar, 11, 2026
Price: $225,000
Living Area: 1,248 Sq. Ft.
311 DEVON DRIVE
CHESTERTOWN, MD | Active
Listed: Nov, 21, 2025
Price: $525,000
Living Area: 3,504 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Nov, 21, 2025
Price: $525,000
Living Area: 3,504 Sq. Ft.
7501 CHURCH HILL ROAD 5
CHESTERTOWN, MD | Active
Listed: Mar, 05, 2026
Price: $1,900
Living Area: 1,000 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 05, 2026
Price: $1,900
Living Area: 1,000 Sq. Ft.
204 ROLLING ROAD
CHESTERTOWN, MD | Closed
Listed: Nov, 07, 2025
Price: $345,000
Living Area: 2,296 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Nov, 07, 2025
Price: $345,000
Living Area: 2,296 Sq. Ft.
11040 KYLIE LANE
CHESTERTOWN, MD | Active Under Contract
Listed: May, 16, 2025
Price: $649,000
Living Area: 3,684 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: May, 16, 2025
Price: $649,000
Living Area: 3,684 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.
GEORGETOWN ROAD
CHESTERTOWN, MD | Active
Listed: Nov, 19, 2025
Price: $90,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Nov, 19, 2025
Price: $90,000
Living Area: 0 Sq. Ft.
509 CANNON STREET
CHESTERTOWN, MD | Closed
Listed: Mar, 03, 2026
Price: $1,400
Living Area: 624 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Mar, 03, 2026
Price: $1,400
Living Area: 624 Sq. Ft.
SCHEELER ROAD LOT 2
CHESTERTOWN, MD | Active
Listed: Mar, 26, 2026
Price: $250,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 26, 2026
Price: $250,000
Living Area: 0 Sq. Ft.
HAACKE DRIVE LOT 3
CHESTERTOWN, MD | Active
Listed: Mar, 26, 2026
Price: $225,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 26, 2026
Price: $225,000
Living Area: 0 Sq. Ft.
0 ROUND TOP ROAD
CHESTERTOWN, MD | Active
Listed: Mar, 20, 2026
Price: $200,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 20, 2026
Price: $200,000
Living Area: 0 Sq. Ft.
105 PEARL CREEK LANE
CHESTERTOWN, MD | Closed
Listed: Jan, 21, 2026
Price: $449,000
Living Area: 1,961 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 21, 2026
Price: $449,000
Living Area: 1,961 Sq. Ft.
144 CHAR NOR MANOR BOULEVARD
CHESTERTOWN, MD | Active Under Contract
Listed: Mar, 27, 2026
Price: $55,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Mar, 27, 2026
Price: $55,000
Living Area: 0 Sq. Ft.
107 LONGFELLOW DRIVE
CHESTERTOWN, MD | Active
Listed: Apr, 03, 2026
Price: $295,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Apr, 03, 2026
Price: $295,000
Living Area: 0 Sq. Ft.
117 WATER STREET N 2B
CHESTERTOWN, MD | Active
Listed: Mar, 01, 2026
Price: $350,000
Living Area: 850 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 01, 2026
Price: $350,000
Living Area: 850 Sq. Ft.
132 PROSPECT STREET
CHESTERTOWN, MD | Active
Listed: Feb, 12, 2026
Price: $157,400
Living Area: 910 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Feb, 12, 2026
Price: $157,400
Living Area: 910 Sq. Ft.
25475 TURNBERRY COURT
CHESTERTOWN, MD | Coming Soon
Listed: Apr, 06, 2026
Price: $867,000
Living Area: 4,145 Sq. Ft.
CHESTERTOWN, MD | Coming Soon
Listed: Apr, 06, 2026
Price: $867,000
Living Area: 4,145 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.
10584 KLAMATH ROAD
CHESTERTOWN, MD | Coming Soon
Listed: Mar, 31, 2026
Price: $319,900
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Coming Soon
Listed: Mar, 31, 2026
Price: $319,900
Living Area: 0 Sq. Ft.
107 CONLEY DRIVE
CHESTERTOWN, MD | Active Under Contract
Listed: Mar, 16, 2026
Price: $170,000
Living Area: 1,140 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Mar, 16, 2026
Price: $170,000
Living Area: 1,140 Sq. Ft.
109 S COLLEGE AVENUE
CHESTERTOWN, MD | Active
Listed: Mar, 20, 2026
Price: $419,900
Living Area: 1,216 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 20, 2026
Price: $419,900
Living Area: 1,216 Sq. Ft.
107 METCALF ROAD
CHESTERTOWN, MD | Active
Listed: Mar, 04, 2026
Price: $259,900
Living Area: 1,200 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 04, 2026
Price: $259,900
Living Area: 1,200 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.
7844 CHESTER COURT
CHESTERTOWN, MD | Active
Listed: Oct, 23, 2025
Price: $695,000
Living Area: 3,248 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Oct, 23, 2025
Price: $695,000
Living Area: 3,248 Sq. Ft.
21217 TEXAS AVENUE
CHESTERTOWN, MD | Active
Listed: Apr, 09, 2026
Price: $265,000
Living Area: 912 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Apr, 09, 2026
Price: $265,000
Living Area: 912 Sq. Ft.
113 PEAR TREE POINT ROAD
CHESTERTOWN, MD | Active
Listed: Mar, 13, 2026
Price: $250,000
Living Area: 1,296 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 13, 2026
Price: $250,000
Living Area: 1,296 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.
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.
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.
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.
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.
108 FLYING CLOUD DRIVE
CHESTERTOWN, MD | Closed
Listed: Nov, 19, 2025
Price: $364,900
Living Area: 1,936 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Nov, 19, 2025
Price: $364,900
Living Area: 1,936 Sq. Ft.
611 CANNON STREET
CHESTERTOWN, MD | Active
Listed: Nov, 11, 2025
Price: $275,000
Living Area: 920 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Nov, 11, 2025
Price: $275,000
Living Area: 920 Sq. Ft.
200 WASHINGTON AVENUE
CHESTERTOWN, MD | Closed
Listed: Aug, 05, 2025
Price: $695,000
Living Area: 2,917 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Aug, 05, 2025
Price: $695,000
Living Area: 2,917 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.
100 ADELA WAY
CHESTERTOWN, MD | Active Under Contract
Listed: Aug, 29, 2025
Price: $498,500
Living Area: 3,799 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Aug, 29, 2025
Price: $498,500
Living Area: 3,799 Sq. Ft.
302 PARK ROW BASEMENT OFFICE 3
CHESTERTOWN, MD | Active
Listed: Jan, 15, 2026
Price: $445
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jan, 15, 2026
Price: $445
Living Area: 0 Sq. Ft.
119 DARDEN ROAD
CHESTERTOWN, MD | Closed
Listed: Feb, 03, 2026
Price: $275,000
Living Area: 1,424 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Feb, 03, 2026
Price: $275,000
Living Area: 1,424 Sq. Ft.
515 N KENT STREET
CHESTERTOWN, MD | Active Under Contract
Listed: Mar, 12, 2026
Price: $495,000
Living Area: 2,220 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Mar, 12, 2026
Price: $495,000
Living Area: 2,220 Sq. Ft.
24775 LANGFORD ROAD
CHESTERTOWN, MD | Active Under Contract
Listed: Dec, 27, 2025
Price: $319,900
Living Area: 1,008 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Dec, 27, 2025
Price: $319,900
Living Area: 1,008 Sq. Ft.
234 N COLLEGE AVENUE
CHESTERTOWN, MD | Active
Listed: Jul, 10, 2025
Price: $130,000
Living Area: 1,296 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jul, 10, 2025
Price: $130,000
Living Area: 1,296 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.
117 WATER STREET N 2A
CHESTERTOWN, MD | Active
Listed: Mar, 01, 2026
Price: $375,000
Living Area: 787 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 01, 2026
Price: $375,000
Living Area: 787 Sq. Ft.
231 RICHARD DRIVE
CHESTERTOWN, MD | Active
Listed: Mar, 02, 2026
Price: $1,279,000
Living Area: 2,956 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 02, 2026
Price: $1,279,000
Living Area: 2,956 Sq. Ft.
112 ELM STREET
CHESTERTOWN, MD | Active Under Contract
Listed: Mar, 06, 2026
Price: $269,900
Living Area: 1,356 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Mar, 06, 2026
Price: $269,900
Living Area: 1,356 Sq. Ft.
103 SUTTON WAY
CHESTERTOWN, MD | Active
Listed: Apr, 03, 2026
Price: $550,000
Living Area: 3,816 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Apr, 03, 2026
Price: $550,000
Living Area: 3,816 Sq. Ft.
217 PHILOSOPHERS TERRACE
CHESTERTOWN, MD | Active Under Contract
Listed: Apr, 01, 2026
Price: $325,000
Living Area: 1,404 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Apr, 01, 2026
Price: $325,000
Living Area: 1,404 Sq. Ft.
201 BIRCH RUN ROAD
CHESTERTOWN, MD | Active
Listed: Mar, 30, 2026
Price: $435,000
Living Area: 1,588 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 30, 2026
Price: $435,000
Living Area: 1,588 Sq. Ft.
704 TRUSLOW ROAD
CHESTERTOWN, MD | Active
Listed: Mar, 26, 2026
Price: $440,000
Living Area: 2,060 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 26, 2026
Price: $440,000
Living Area: 2,060 Sq. Ft.
21125 IOWA AVENUE
CHESTERTOWN, MD | Active
Listed: Mar, 10, 2026
Price: $339,900
Living Area: 1,294 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 10, 2026
Price: $339,900
Living Area: 1,294 Sq. Ft.
10087 JOHN CARVILL ROAD
CHESTERTOWN, MD | Coming Soon
Listed: Apr, 02, 2026
Price: $695,000
Living Area: 1,566 Sq. Ft.
CHESTERTOWN, MD | Coming Soon
Listed: Apr, 02, 2026
Price: $695,000
Living Area: 1,566 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.
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.
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.
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.
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.
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.
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.
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.
7989 QUAKER NECK ROAD
CHESTERTOWN, MD | Active
Listed: Aug, 27, 2025
Price: $2,400,000
Living Area: 4,305 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Aug, 27, 2025
Price: $2,400,000
Living Area: 4,305 Sq. Ft.
302 PARK ROW OFFICE 2
CHESTERTOWN, MD | Closed
Listed: Aug, 20, 2025
Price: $600
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Aug, 20, 2025
Price: $600
Living Area: 0 Sq. Ft.
23055 OLD FAIRLEE ROAD
CHESTERTOWN, MD | Pending
Listed: Jan, 17, 2026
Price: $330,000
Living Area: 1,628 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: Jan, 17, 2026
Price: $330,000
Living Area: 1,628 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.
SCHEELER ROAD LOT 2
CHESTERTOWN, MD | Active
Listed: Mar, 26, 2026
Price: $250,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 26, 2026
Price: $250,000
Living Area: 0 Sq. Ft.
870 HIGH STREET INDIVIDUAL OFFICES
CHESTERTOWN, MD | Active
Listed: Mar, 25, 2026
Price: $250
Living Area: 15,986 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 25, 2026
Price: $250
Living Area: 15,986 Sq. Ft.
101 COLEMAN DRIVE
CHESTERTOWN, MD | Active
Listed: Mar, 26, 2026
Price: $524,900
Living Area: 2,268 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 26, 2026
Price: $524,900
Living Area: 2,268 Sq. Ft.
107 OAK LEAF DRIVE
CHESTERTOWN, MD | Closed
Listed: Feb, 12, 2026
Price: $295,000
Living Area: 1,947 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Feb, 12, 2026
Price: $295,000
Living Area: 1,947 Sq. Ft.
302 PARK ROW BASEMENT 2
CHESTERTOWN, MD | Active
Listed: Mar, 16, 2026
Price: $395
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 16, 2026
Price: $395
Living Area: 0 Sq. Ft.
115 ACORN DRIVE
CHESTERTOWN, MD | Coming Soon
Listed: Apr, 09, 2026
Price: $296,000
Living Area: 1,864 Sq. Ft.
CHESTERTOWN, MD | Coming Soon
Listed: Apr, 09, 2026
Price: $296,000
Living Area: 1,864 Sq. Ft.
720 DEEP LANDING ROAD
CHESTERTOWN, MD | Active
Listed: Apr, 03, 2026
Price: $369,999
Living Area: 1,271 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Apr, 03, 2026
Price: $369,999
Living Area: 1,271 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.
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.
2032 PONDTOWN ROAD
CHESTERTOWN, MD | Active
Listed: Mar, 27, 2026
Price: $325,000
Living Area: 1,120 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 27, 2026
Price: $325,000
Living Area: 1,120 Sq. Ft.
206 FLYWAY LANE
CHESTERTOWN, MD | Closed
Listed: Mar, 07, 2026
Price: $499,900
Living Area: 3,000 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Mar, 07, 2026
Price: $499,900
Living Area: 3,000 Sq. Ft.
21217 TEXAS AVENUE
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $99,900
Living Area: 912 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $99,900
Living Area: 912 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.
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.
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 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.
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.
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.
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.
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.
201 N LYNCHBURG STREET
CHESTERTOWN, MD | Active
Listed: Feb, 25, 2026
Price: $795,000
Living Area: 2,045 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Feb, 25, 2026
Price: $795,000
Living Area: 2,045 Sq. Ft.
201 N LYNCHBURG STREET
CHESTERTOWN, MD | Active
Listed: Feb, 27, 2026
Price: $795,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Feb, 27, 2026
Price: $795,000
Living Area: 0 Sq. Ft.
TONOPAH RD.
CHESTERTOWN, MD | Active Under Contract
Listed: Aug, 12, 2025
Price: $40,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Aug, 12, 2025
Price: $40,000
Living Area: 0 Sq. Ft.
301 LINCOLN DRIVE
CHESTERTOWN, MD | Active
Listed: Mar, 03, 2026
Price: $309,900
Living Area: 1,152 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 03, 2026
Price: $309,900
Living Area: 1,152 Sq. Ft.
206 BURCHARD SAWMILL ROAD
CHESTERTOWN, MD | Active
Listed: Mar, 17, 2026
Price: $29,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 17, 2026
Price: $29,000
Living Area: 0 Sq. Ft.
23110 OLD FAIRLEE ROAD
CHESTERTOWN, MD | Closed
Listed: Sep, 10, 2025
Price: $339,900
Living Area: 1,805 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Sep, 10, 2025
Price: $339,900
Living Area: 1,805 Sq. Ft.
136 HILLTOP DRIVE
CHESTERTOWN, MD | Coming Soon
Listed: Apr, 06, 2026
Price: $366,000
Living Area: 1,432 Sq. Ft.
CHESTERTOWN, MD | Coming Soon
Listed: Apr, 06, 2026
Price: $366,000
Living Area: 1,432 Sq. Ft.
327 CANNON STREET
CHESTERTOWN, MD | Active
Listed: Apr, 06, 2026
Price: $1,300,000
Living Area: 3,740 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Apr, 06, 2026
Price: $1,300,000
Living Area: 3,740 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.
8276 BROAD NECK ROAD
CHESTERTOWN, MD | Active
Listed: Mar, 14, 2026
Price: $1,495,000
Living Area: 3,383 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 14, 2026
Price: $1,495,000
Living Area: 3,383 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.
8750 GEORGETOWN ROAD
CHESTERTOWN, MD | Closed
Listed: Oct, 16, 2025
Price: $334,000
Living Area: 1,900 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Oct, 16, 2025
Price: $334,000
Living Area: 1,900 Sq. Ft.
222 MOUNT VERNON AVENUE
CHESTERTOWN, MD | Active
Listed: Nov, 02, 2025
Price: $439,999
Living Area: 1,656 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Nov, 02, 2025
Price: $439,999
Living Area: 1,656 Sq. Ft.
108 PINE STREET
CHESTERTOWN, MD | Pending
Listed: Mar, 31, 2026
Price: $115,000
Living Area: 910 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: Mar, 31, 2026
Price: $115,000
Living Area: 910 Sq. Ft.
226 S WATER STREET
CHESTERTOWN, MD | Active
Listed: Apr, 08, 2026
Price: $898,000
Living Area: 2,172 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Apr, 08, 2026
Price: $898,000
Living Area: 2,172 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.
