Listings in 21620 - KENT County, Maryland
Displaying 1 – 200 of 250 Real estate listings
104 GARLAND AVENUE
CHESTERTOWN, MD | Closed
Listed: Feb, 25, 2026
Price: $440,000
Living Area: 1,734 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Feb, 25, 2026
Price: $440,000
Living Area: 1,734 Sq. Ft.
1 REED COURT
CHESTERTOWN, MD | Closed
Listed: May, 06, 2024
Price: $379,000
Living Area: 1,854 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: May, 06, 2024
Price: $379,000
Living Area: 1,854 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.
513 ROUND TOP ROAD
CHESTERTOWN, MD | Closed
Listed: Mar, 11, 2026
Price: $225,000
Living Area: 1,248 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Mar, 11, 2026
Price: $225,000
Living Area: 1,248 Sq. Ft.
8706 ELM ROAD
CHESTERTOWN, MD | Active
Listed: Apr, 16, 2026
Price: $320,000
Living Area: 1,232 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Apr, 16, 2026
Price: $320,000
Living Area: 1,232 Sq. Ft.
148 STEP ROAD
CHESTERTOWN, MD | Closed
Listed: Feb, 24, 2026
Price: $369,000
Living Area: 1,400 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Feb, 24, 2026
Price: $369,000
Living Area: 1,400 Sq. Ft.
110 WILTON ROAD
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $110,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $110,000
Living Area: 0 Sq. Ft.
11040 KYLIE LANE
CHESTERTOWN, MD | Closed
Listed: May, 16, 2025
Price: $649,000
Living Area: 3,684 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: May, 16, 2025
Price: $649,000
Living Area: 3,684 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.
128 N QUEEN STREET 1
CHESTERTOWN, MD | Closed
Listed: Apr, 17, 2026
Price: $1,000
Living Area: 500 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Apr, 17, 2026
Price: $1,000
Living Area: 500 Sq. Ft.
208 CENTRAL DRIVE
CHESTERTOWN, MD | Active
Listed: Apr, 15, 2026
Price: $299,000
Living Area: 1,120 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Apr, 15, 2026
Price: $299,000
Living Area: 1,120 Sq. Ft.
107 METCALF ROAD
CHESTERTOWN, MD | Closed
Listed: Mar, 04, 2026
Price: $259,900
Living Area: 1,200 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Mar, 04, 2026
Price: $259,900
Living Area: 1,200 Sq. Ft.
25475 TURNBERRY COURT
CHESTERTOWN, MD | Closed
Listed: Apr, 06, 2026
Price: $867,000
Living Area: 4,145 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Apr, 06, 2026
Price: $867,000
Living Area: 4,145 Sq. Ft.
7844 CHESTER COURT
CHESTERTOWN, MD | Active Under Contract
Listed: Oct, 23, 2025
Price: $670,000
Living Area: 3,248 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Oct, 23, 2025
Price: $670,000
Living Area: 3,248 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.
25750 COLLINS AVENUE
CHESTERTOWN, MD | Active
Listed: Jun, 12, 2026
Price: $468,000
Living Area: 3,262 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jun, 12, 2026
Price: $468,000
Living Area: 3,262 Sq. Ft.
102 FLYING CLOUD DRIVE
CHESTERTOWN, MD | Active
Listed: May, 20, 2026
Price: $329,900
Living Area: 1,896 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: May, 20, 2026
Price: $329,900
Living Area: 1,896 Sq. Ft.
205 RIVER ROAD
CHESTERTOWN, MD | Closed
Listed: Jun, 06, 2026
Price: $869,900
Living Area: 2,877 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 06, 2026
Price: $869,900
Living Area: 2,877 Sq. Ft.
304 HADAWAY DRIVE
CHESTERTOWN, MD | Active Under Contract
Listed: May, 14, 2026
Price: $309,900
Living Area: 1,325 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: May, 14, 2026
Price: $309,900
Living Area: 1,325 Sq. Ft.
240 MERGANSER DRIVE
CHESTERTOWN, MD | Active
Listed: Apr, 13, 2026
Price: $365,000
Living Area: 1,120 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Apr, 13, 2026
Price: $365,000
Living Area: 1,120 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.
103 METCALF RD
CHESTERTOWN, MD | Active
Listed: Apr, 21, 2026
Price: $259,900
Living Area: 1,280 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Apr, 21, 2026
Price: $259,900
Living Area: 1,280 Sq. Ft.
10584 KLAMATH ROAD
CHESTERTOWN, MD | Pending
Listed: Mar, 31, 2026
Price: $319,900
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: Mar, 31, 2026
Price: $319,900
Living Area: 0 Sq. Ft.
SANDY BOTTOM ROAD
CHESTERTOWN, MD | Active
Listed: May, 14, 2026
Price: $59,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: May, 14, 2026
Price: $59,000
Living Area: 0 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.
#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.
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.
112 METCALF ROAD
CHESTERTOWN, MD | Closed
Listed: Jan, 24, 2026
Price: $249,500
Living Area: 1,280 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 24, 2026
Price: $249,500
Living Area: 1,280 Sq. Ft.
101 PINE TREE ROAD
CHESTERTOWN, MD | Closed
Listed: Feb, 17, 2026
Price: $480,000
Living Area: 1,848 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Feb, 17, 2026
Price: $480,000
Living Area: 1,848 Sq. Ft.
107 LONGFELLOW DRIVE
CHESTERTOWN, MD | Closed
Listed: Apr, 03, 2026
Price: $295,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Apr, 03, 2026
Price: $295,000
Living Area: 0 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.
132 PROSPECT STREET
CHESTERTOWN, MD | Closed
Listed: Feb, 12, 2026
Price: $157,400
Living Area: 910 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Feb, 12, 2026
Price: $157,400
Living Area: 910 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.
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.
107 CONLEY DRIVE
CHESTERTOWN, MD | Closed
Listed: Mar, 16, 2026
Price: $170,000
Living Area: 1,140 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Mar, 16, 2026
Price: $170,000
Living Area: 1,140 Sq. Ft.
23416 CLOQUET ROAD
CHESTERTOWN, MD | Closed
Listed: Jul, 02, 2020
Price: $224,900
Living Area: 1,512 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jul, 02, 2020
Price: $224,900
Living Area: 1,512 Sq. Ft.
102 CONLEY DRIVE
CHESTERTOWN, MD | Closed
Listed: Jun, 14, 2022
Price: $184,900
Living Area: 1,280 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 14, 2022
Price: $184,900
Living Area: 1,280 Sq. Ft.
111 CHESTER ARMS DRIVE
CHESTERTOWN, MD | Closed
Listed: Oct, 20, 2022
Price: $229,900
Living Area: 1,140 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Oct, 20, 2022
Price: $229,900
Living Area: 1,140 Sq. Ft.
126 CHAR NOR MANOR BOULEVARD
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $224,999
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $224,999
Living Area: 0 Sq. Ft.
113 PEAR TREE POINT ROAD
CHESTERTOWN, MD | Closed
Listed: Mar, 13, 2026
Price: $250,000
Living Area: 1,296 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Mar, 13, 2026
Price: $250,000
Living Area: 1,296 Sq. Ft.
8796 MARYLAND PARKWAY
CHESTERTOWN, MD | Active
Listed: May, 28, 2026
Price: $1,650,000
Living Area: 4,776 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: May, 28, 2026
Price: $1,650,000
Living Area: 4,776 Sq. Ft.
100 PROSPECT STREET
CHESTERTOWN, MD | Active Under Contract
Listed: May, 12, 2026
Price: $215,000
Living Area: 1,373 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: May, 12, 2026
Price: $215,000
Living Area: 1,373 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.
216 BLAKEFIELD DRIVE
CHESTERTOWN, MD | Closed
Listed: Nov, 02, 2025
Price: $559,000
Living Area: 2,400 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Nov, 02, 2025
Price: $559,000
Living Area: 2,400 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.
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.
109 2ND STREET
CHESTERTOWN, MD | Active
Listed: May, 09, 2026
Price: $135,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: May, 09, 2026
Price: $135,000
Living Area: 0 Sq. Ft.
104 MAPLE AVENUE
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $725,000
Living Area: 5,472 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $725,000
Living Area: 5,472 Sq. Ft.
104 MAPLE AVENUE 3
CHESTERTOWN, MD | Closed
Listed: Apr, 16, 2026
Price: $1,520
Living Area: 800 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Apr, 16, 2026
Price: $1,520
Living Area: 800 Sq. Ft.
8796 MARYLAND PARKWAY
CHESTERTOWN, MD | Active
Listed: Jun, 02, 2026
Price: $1,650,000
Living Area: 5,000 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jun, 02, 2026
Price: $1,650,000
Living Area: 5,000 Sq. Ft.
21324 PERSIMMON DRIVE
CHESTERTOWN, MD | Closed
Listed: Mar, 04, 2026
Price: $124,900
Living Area: 1,232 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Mar, 04, 2026
Price: $124,900
Living Area: 1,232 Sq. Ft.
234 N COLLEGE AVENUE
CHESTERTOWN, MD | Active
Listed: Jun, 12, 2026
Price: $100,000
Living Area: 1,296 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jun, 12, 2026
Price: $100,000
Living Area: 1,296 Sq. Ft.
202 VALLEY ROAD
CHESTERTOWN, MD | Closed
Listed: May, 12, 2026
Price: $325,000
Living Area: 1,427 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: May, 12, 2026
Price: $325,000
Living Area: 1,427 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.
522 HIGH STREET
CHESTERTOWN, MD | Active
Listed: May, 30, 2026
Price: $399,900
Living Area: 1,518 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: May, 30, 2026
Price: $399,900
Living Area: 1,518 Sq. Ft.
10781 FERMOY ROAD
CHESTERTOWN, MD | Active
Listed: Jun, 05, 2026
Price: $429,900
Living Area: 2,160 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jun, 05, 2026
Price: $429,900
Living Area: 2,160 Sq. Ft.
109 S COLLEGE AVENUE
CHESTERTOWN, MD | Closed
Listed: Mar, 20, 2026
Price: $419,900
Living Area: 1,216 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Mar, 20, 2026
Price: $419,900
Living Area: 1,216 Sq. Ft.
103 MAPLE AVENUE
CHESTERTOWN, MD | Active Under Contract
Listed: Jun, 15, 2026
Price: $615,000
Living Area: 4,536 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Jun, 15, 2026
Price: $615,000
Living Area: 4,536 Sq. Ft.
118 GRANT COURT
CHESTERTOWN, MD | Closed
Listed: Jun, 24, 2020
Price: $305,350
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 24, 2020
Price: $305,350
Living Area: 0 Sq. Ft.
7501 CHURCH HILL ROAD 5
CHESTERTOWN, MD | Active
Listed: Mar, 05, 2026
Price: $1,800
Living Area: 1,000 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 05, 2026
Price: $1,800
Living Area: 1,000 Sq. Ft.
23416 CLOQUET ROAD
CHESTERTOWN, MD | Closed
Listed: Apr, 30, 2026
Price: $384,000
Living Area: 1,512 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Apr, 30, 2026
Price: $384,000
Living Area: 1,512 Sq. Ft.
311 DEVON DRIVE
CHESTERTOWN, MD | Active Under Contract
Listed: Nov, 21, 2025
Price: $475,000
Living Area: 3,504 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Nov, 21, 2025
Price: $475,000
Living Area: 3,504 Sq. Ft.
21217 TEXAS AVENUE
CHESTERTOWN, MD | Active Under Contract
Listed: Apr, 09, 2026
Price: $244,500
Living Area: 912 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Apr, 09, 2026
Price: $244,500
Living Area: 912 Sq. Ft.
144 PROSPECT STREET
CHESTERTOWN, MD | Closed
Listed: May, 02, 2026
Price: $159,000
Living Area: 1,082 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: May, 02, 2026
Price: $159,000
Living Area: 1,082 Sq. Ft.
101 S MILL STREET
CHESTERTOWN, MD | Active
Listed: Jun, 12, 2026
Price: $515,000
Living Area: 1,476 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jun, 12, 2026
Price: $515,000
Living Area: 1,476 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.
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.
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.
23055 OLD FAIRLEE ROAD
CHESTERTOWN, MD | Closed
Listed: Jan, 17, 2026
Price: $330,000
Living Area: 1,628 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 17, 2026
Price: $330,000
Living Area: 1,628 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.
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.
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.
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.
515 N KENT STREET
CHESTERTOWN, MD | Closed
Listed: Mar, 12, 2026
Price: $495,000
Living Area: 2,220 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Mar, 12, 2026
Price: $495,000
Living Area: 2,220 Sq. Ft.
719 ROUND TOP ROAD
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $105,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $105,000
Living Area: 0 Sq. Ft.
201 GREENWOOD AVENUE
CHESTERTOWN, MD | Closed
Listed: Jan, 05, 2026
Price: $495,000
Living Area: 3,984 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 05, 2026
Price: $495,000
Living Area: 3,984 Sq. Ft.
113 HILLTOP DRIVE
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $319,000
Living Area: 2,406 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $319,000
Living Area: 2,406 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.
10087 JOHN CARVILL ROAD
CHESTERTOWN, MD | Closed
Listed: Apr, 02, 2026
Price: $695,000
Living Area: 1,566 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Apr, 02, 2026
Price: $695,000
Living Area: 1,566 Sq. Ft.
704 TRUSLOW ROAD
CHESTERTOWN, MD | Active Under Contract
Listed: Mar, 26, 2026
Price: $440,000
Living Area: 2,060 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Mar, 26, 2026
Price: $440,000
Living Area: 2,060 Sq. Ft.
2032 PONDTOWN ROAD
CHESTERTOWN, MD | Closed
Listed: Mar, 27, 2026
Price: $325,000
Living Area: 1,120 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Mar, 27, 2026
Price: $325,000
Living Area: 1,120 Sq. Ft.
25416 COMMERCE LANE
CHESTERTOWN, MD | Active
Listed: Jun, 10, 2026
Price: $1,100,000
Living Area: 5,600 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jun, 10, 2026
Price: $1,100,000
Living Area: 5,600 Sq. Ft.
24581 WILLOW OAK LANE
CHESTERTOWN, MD | Active Under Contract
Listed: Apr, 24, 2026
Price: $229,990
Living Area: 1,352 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Apr, 24, 2026
Price: $229,990
Living Area: 1,352 Sq. Ft.
201 BIRCH RUN ROAD
CHESTERTOWN, MD | Closed
Listed: Mar, 30, 2026
Price: $435,000
Living Area: 1,588 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Mar, 30, 2026
Price: $435,000
Living Area: 1,588 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.
218 CAMELOT DRIVE
CHESTERTOWN, MD | Active
Listed: Dec, 14, 2025
Price: $499,999
Living Area: 3,932 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Dec, 14, 2025
Price: $499,999
Living Area: 3,932 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.
215 FAIRVIEW DRIVE
CHESTERTOWN, MD | Active Under Contract
Listed: May, 01, 2026
Price: $425,000
Living Area: 1,784 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: May, 01, 2026
Price: $425,000
Living Area: 1,784 Sq. Ft.
128 N QUEEN STREET 3
CHESTERTOWN, MD | Active
Listed: May, 18, 2026
Price: $1,450
Living Area: 900 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: May, 18, 2026
Price: $1,450
Living Area: 900 Sq. Ft.
8886 GEORGETOWN ROAD
CHESTERTOWN, MD | Active
Listed: Jun, 05, 2026
Price: $80,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jun, 05, 2026
Price: $80,000
Living Area: 0 Sq. Ft.
221 DUTCHESS ROAD
CHESTERTOWN, MD | Active Under Contract
Listed: Jun, 16, 2026
Price: $228,000
Living Area: 2,260 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Jun, 16, 2026
Price: $228,000
Living Area: 2,260 Sq. Ft.
720 DEEP LANDING ROAD
CHESTERTOWN, MD | Closed
Listed: Apr, 03, 2026
Price: $369,900
Living Area: 1,271 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Apr, 03, 2026
Price: $369,900
Living Area: 1,271 Sq. Ft.
112 ELM STREET
CHESTERTOWN, MD | Closed
Listed: Mar, 06, 2026
Price: $269,900
Living Area: 1,356 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Mar, 06, 2026
Price: $269,900
Living Area: 1,356 Sq. Ft.
9816 FAIRLEE ROAD
CHESTERTOWN, MD | Pending
Listed: May, 01, 2026
Price: $535,000
Living Area: 1,624 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: May, 01, 2026
Price: $535,000
Living Area: 1,624 Sq. Ft.
104 ACORN DRIVE
CHESTERTOWN, MD | Active
Listed: Jun, 12, 2026
Price: $284,900
Living Area: 1,900 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jun, 12, 2026
Price: $284,900
Living Area: 1,900 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.
407 HIGH STREET
CHESTERTOWN, MD | Active Under Contract
Listed: May, 03, 2026
Price: $798,000
Living Area: 3,047 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: May, 03, 2026
Price: $798,000
Living Area: 3,047 Sq. Ft.
351 CALVERT STREET
CHESTERTOWN, MD | Active
Listed: Jun, 29, 2026
Price: $2,000
Living Area: 1,122 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jun, 29, 2026
Price: $2,000
Living Area: 1,122 Sq. Ft.
22470 FAIRGALE FARM LANE
CHESTERTOWN, MD | Active
Listed: May, 19, 2026
Price: $1,450,000
Living Area: 4,257 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: May, 19, 2026
Price: $1,450,000
Living Area: 4,257 Sq. Ft.
7761 BROAD NECK ROAD
CHESTERTOWN, MD | Closed
Listed: May, 24, 2026
Price: $1,500,000
Living Area: 2,700 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: May, 24, 2026
Price: $1,500,000
Living Area: 2,700 Sq. Ft.
231 RICHARD DRIVE
CHESTERTOWN, MD | Closed
Listed: Mar, 02, 2026
Price: $1,150,000
Living Area: 2,956 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Mar, 02, 2026
Price: $1,150,000
Living Area: 2,956 Sq. Ft.
1014 TWIN COURT
CHESTERTOWN, MD | Closed
Listed: May, 08, 2026
Price: $499,000
Living Area: 1,817 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: May, 08, 2026
Price: $499,000
Living Area: 1,817 Sq. Ft.
611 CANNON STREET
CHESTERTOWN, MD | Active Under Contract
Listed: Nov, 11, 2025
Price: $275,000
Living Area: 920 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Nov, 11, 2025
Price: $275,000
Living Area: 920 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.
7989 QUAKER NECK ROAD
CHESTERTOWN, MD | Active
Listed: Aug, 27, 2025
Price: $2,200,000
Living Area: 4,305 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Aug, 27, 2025
Price: $2,200,000
Living Area: 4,305 Sq. Ft.
114 CHESTER VW
CHESTERTOWN, MD | Closed
Listed: Jun, 17, 2026
Price: $1,650,000
Living Area: 2,064 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 17, 2026
Price: $1,650,000
Living Area: 2,064 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.
101 COLEMAN DRIVE
CHESTERTOWN, MD | Active
Listed: Mar, 26, 2026
Price: $519,900
Living Area: 2,268 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 26, 2026
Price: $519,900
Living Area: 2,268 Sq. Ft.
202 ROYSTON SHORES ROAD
CHESTERTOWN, MD | Active Under Contract
Listed: Jun, 01, 2026
Price: $1,200,000
Living Area: 2,292 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Jun, 01, 2026
Price: $1,200,000
Living Area: 2,292 Sq. Ft.
21363 LYNN LANE
CHESTERTOWN, MD | Closed
Listed: May, 15, 2026
Price: $205,000
Living Area: 1,314 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: May, 15, 2026
Price: $205,000
Living Area: 1,314 Sq. Ft.
521 N KENT STREET
CHESTERTOWN, MD | Active Under Contract
Listed: Jul, 06, 2026
Price: $385,000
Living Area: 1,934 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Jul, 06, 2026
Price: $385,000
Living Area: 1,934 Sq. Ft.
107 FLYING CLOUD DRIVE
CHESTERTOWN, MD | Active
Listed: May, 06, 2026
Price: $375,000
Living Area: 2,534 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: May, 06, 2026
Price: $375,000
Living Area: 2,534 Sq. Ft.
217 PHILOSOPHERS TERRACE
CHESTERTOWN, MD | Closed
Listed: Apr, 01, 2026
Price: $325,000
Living Area: 1,404 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Apr, 01, 2026
Price: $325,000
Living Area: 1,404 Sq. Ft.
111 RIVERVIEW POINT
CHESTERTOWN, MD | Closed
Listed: Apr, 21, 2026
Price: $3,000
Living Area: 1,600 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Apr, 21, 2026
Price: $3,000
Living Area: 1,600 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.
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.
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.
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.
100 ADELA WAY
CHESTERTOWN, MD | Closed
Listed: Aug, 29, 2025
Price: $498,500
Living Area: 3,799 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Aug, 29, 2025
Price: $498,500
Living Area: 3,799 Sq. Ft.
109 METCALF ROAD
CHESTERTOWN, MD | Closed
Listed: Dec, 09, 2025
Price: $264,900
Living Area: 1,280 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Dec, 09, 2025
Price: $264,900
Living Area: 1,280 Sq. Ft.
108 OAK LEAF DRIVE
CHESTERTOWN, MD | Closed
Listed: Apr, 16, 2026
Price: $299,500
Living Area: 1,867 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Apr, 16, 2026
Price: $299,500
Living Area: 1,867 Sq. Ft.
10594 MILLBROOK DRIVE
CHESTERTOWN, MD | Closed
Listed: Apr, 13, 2026
Price: $329,000
Living Area: 1,499 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Apr, 13, 2026
Price: $329,000
Living Area: 1,499 Sq. Ft.
213 BYFORD DRIVE
CHESTERTOWN, MD | Active
Listed: Jun, 03, 2026
Price: $380,000
Living Area: 1,277 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jun, 03, 2026
Price: $380,000
Living Area: 1,277 Sq. Ft.
1010 TWIN COURT
CHESTERTOWN, MD | Active
Listed: May, 28, 2026
Price: $2,400
Living Area: 1,476 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: May, 28, 2026
Price: $2,400
Living Area: 1,476 Sq. Ft.
21125 IOWA AVENUE
CHESTERTOWN, MD | Closed
Listed: Mar, 10, 2026
Price: $339,900
Living Area: 1,294 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Mar, 10, 2026
Price: $339,900
Living Area: 1,294 Sq. Ft.
126 CHAR NOR MANOR BOULEVARD
CHESTERTOWN, MD | Closed
Listed: Apr, 10, 2026
Price: $349,000
Living Area: 1,304 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Apr, 10, 2026
Price: $349,000
Living Area: 1,304 Sq. Ft.
115 ACORN DRIVE
CHESTERTOWN, MD | Closed
Listed: Apr, 09, 2026
Price: $296,000
Living Area: 1,864 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Apr, 09, 2026
Price: $296,000
Living Area: 1,864 Sq. Ft.
23348 VIREO ROAD
CHESTERTOWN, MD | Closed
Listed: Nov, 01, 2019
Price: $189,900
Living Area: 1,404 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Nov, 01, 2019
Price: $189,900
Living Area: 1,404 Sq. Ft.
10594 MILLBROOK DRIVE
CHESTERTOWN, MD | Closed
Listed: Apr, 20, 2020
Price: $224,900
Living Area: 1,500 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Apr, 20, 2020
Price: $224,900
Living Area: 1,500 Sq. Ft.
10593 WATONGA ROAD
CHESTERTOWN, MD | Closed
Listed: Dec, 15, 2020
Price: $235,900
Living Area: 1,512 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Dec, 15, 2020
Price: $235,900
Living Area: 1,512 Sq. Ft.
103 CONLEY DRIVE
CHESTERTOWN, MD | Closed
Listed: May, 03, 2021
Price: $219,900
Living Area: 1,260 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: May, 03, 2021
Price: $219,900
Living Area: 1,260 Sq. Ft.
103 CHESTER ARMS DRIVE
CHESTERTOWN, MD | Closed
Listed: Feb, 02, 2022
Price: $229,900
Living Area: 1,260 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Feb, 02, 2022
Price: $229,900
Living Area: 1,260 Sq. Ft.
105 CHESTER ARMS DRIVE
CHESTERTOWN, MD | Closed
Listed: Jun, 15, 2022
Price: $229,900
Living Area: 1,140 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 15, 2022
Price: $229,900
Living Area: 1,140 Sq. Ft.
107 CHESTER ARMS DRIVE
CHESTERTOWN, MD | Closed
Listed: Aug, 21, 2022
Price: $229,900
Living Area: 1,140 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Aug, 21, 2022
Price: $229,900
Living Area: 1,140 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.
110 S QUEEN STREET
CHESTERTOWN, MD | Pending
Listed: May, 11, 2026
Price: $525,000
Living Area: 778 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: May, 11, 2026
Price: $525,000
Living Area: 778 Sq. Ft.
306 ROOSEVELT DRIVE
CHESTERTOWN, MD | Closed
Listed: Jan, 23, 2024
Price: $250,000
Living Area: 1,152 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 23, 2024
Price: $250,000
Living Area: 1,152 Sq. Ft.
201 RIVER ROAD
CHESTERTOWN, MD | Active Under Contract
Listed: Jun, 16, 2026
Price: $629,900
Living Area: 2,430 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Jun, 16, 2026
Price: $629,900
Living Area: 2,430 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.
104 CONLEY DRIVE
CHESTERTOWN, MD | Active
Listed: Jun, 17, 2026
Price: $239,900
Living Area: 1,280 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jun, 17, 2026
Price: $239,900
Living Area: 1,280 Sq. Ft.
110 PROSPECT STREET
CHESTERTOWN, MD | Active
Listed: Jun, 09, 2026
Price: $89,900
Living Area: 2,210 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jun, 09, 2026
Price: $89,900
Living Area: 2,210 Sq. Ft.
104 MAPLE AVENUE
CHESTERTOWN, MD | Active
Listed: Apr, 17, 2026
Price: $1,350,000
Living Area: 7,296 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Apr, 17, 2026
Price: $1,350,000
Living Area: 7,296 Sq. Ft.
896 WASHINGTON AVENUE
CHESTERTOWN, MD | Active
Listed: Jun, 26, 2026
Price: $325,000
Living Area: 1,000 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jun, 26, 2026
Price: $325,000
Living Area: 1,000 Sq. Ft.
BUCK NECK LANDING ROAD
CHESTERTOWN, MD | Pending
Listed: Aug, 15, 2025
Price: $10,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: Aug, 15, 2025
Price: $10,000
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.
22481 GOOSE HOLLOW DRIVE
CHESTERTOWN, MD | Active
Listed: Jun, 20, 2026
Price: $279,900
Living Area: 1,296 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jun, 20, 2026
Price: $279,900
Living Area: 1,296 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.
109 CEDAR STREET
CHESTERTOWN, MD | Coming Soon
Listed: Jul, 08, 2026
Price: $325,000
Living Area: 1,397 Sq. Ft.
CHESTERTOWN, MD | Coming Soon
Listed: Jul, 08, 2026
Price: $325,000
Living Area: 1,397 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.
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.
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.
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.
23570 CLARISSA ROAD
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $140,400
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 01, 2026
Price: $140,400
Living Area: 0 Sq. Ft.
21217 TEXAS AVENUE
CHESTERTOWN, MD | Closed
Listed: Jul, 10, 2025
Price: $1,600
Living Area: 912 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jul, 10, 2025
Price: $1,600
Living Area: 912 Sq. Ft.
7482 POPLAR AVENUE
CHESTERTOWN, MD | Closed
Listed: Jul, 21, 2020
Price: $170,000
Living Area: 975 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jul, 21, 2020
Price: $170,000
Living Area: 975 Sq. Ft.
103 FLYING CLOUD DRIVE
CHESTERTOWN, MD | Closed
Listed: Mar, 27, 2026
Price: $339,900
Living Area: 1,724 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Mar, 27, 2026
Price: $339,900
Living Area: 1,724 Sq. Ft.
201 N LYNCHBURG STREET
CHESTERTOWN, MD | Active
Listed: Jan, 22, 2026
Price: $750,000
Living Area: 3,527 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jan, 22, 2026
Price: $750,000
Living Area: 3,527 Sq. Ft.
201 N LYNCHBURG STREET
CHESTERTOWN, MD | Active
Listed: Feb, 25, 2026
Price: $750,000
Living Area: 2,045 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Feb, 25, 2026
Price: $750,000
Living Area: 2,045 Sq. Ft.
201 N LYNCHBURG STREET
CHESTERTOWN, MD | Active
Listed: Feb, 27, 2026
Price: $750,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Feb, 27, 2026
Price: $750,000
Living Area: 0 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.
136 HILLTOP DRIVE
CHESTERTOWN, MD | Closed
Listed: Apr, 06, 2026
Price: $366,000
Living Area: 1,432 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Apr, 06, 2026
Price: $366,000
Living Area: 1,432 Sq. Ft.
154 LONGFELLOW DRIVE
CHESTERTOWN, MD | Closed
Listed: Feb, 24, 2026
Price: $299,000
Living Area: 1,408 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Feb, 24, 2026
Price: $299,000
Living Area: 1,408 Sq. Ft.
204 DOUBLE CREEK ROAD
CHESTERTOWN, MD | Active
Listed: Feb, 01, 2026
Price: $565,000
Living Area: 2,927 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Feb, 01, 2026
Price: $565,000
Living Area: 2,927 Sq. Ft.
222 MOUNT VERNON AVENUE
CHESTERTOWN, MD | Active
Listed: Jun, 06, 2026
Price: $2,950
Living Area: 1,656 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jun, 06, 2026
Price: $2,950
Living Area: 1,656 Sq. Ft.
118 LITTLE HARBOR WAY 202
CHESTERTOWN, MD | Closed
Listed: Oct, 08, 2025
Price: $675,000
Living Area: 1,600 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Oct, 08, 2025
Price: $675,000
Living Area: 1,600 Sq. Ft.
301 LINCOLN DRIVE
CHESTERTOWN, MD | Closed
Listed: Mar, 03, 2026
Price: $299,900
Living Area: 1,152 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Mar, 03, 2026
Price: $299,900
Living Area: 1,152 Sq. Ft.
LOTS 253-254 CARIMON ROAD
CHESTERTOWN, MD | Closed
Listed: Dec, 17, 2024
Price: $9,500
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Dec, 17, 2024
Price: $9,500
Living Area: 0 Sq. Ft.
125 CONLEY DRIVE
CHESTERTOWN, MD | Closed
Listed: May, 02, 2019
Price: $129,900
Living Area: 1,280 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: May, 02, 2019
Price: $129,900
Living Area: 1,280 Sq. Ft.
1906 PONDTOWN ROAD
CHESTERTOWN, MD | Active
Listed: Jun, 01, 2026
Price: $110,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jun, 01, 2026
Price: $110,000
Living Area: 0 Sq. Ft.
10572 WATONGA ROAD
CHESTERTOWN, MD | Active Under Contract
Listed: Jun, 05, 2026
Price: $325,000
Living Area: 1,404 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Jun, 05, 2026
Price: $325,000
Living Area: 1,404 Sq. Ft.
104 MAPLE AVENUE 6
CHESTERTOWN, MD | Active
Listed: Apr, 17, 2026
Price: $2,050
Living Area: 900 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Apr, 17, 2026
Price: $2,050
Living Area: 900 Sq. Ft.
110 S QUEEN STREET
CHESTERTOWN, MD | Pending
Listed: May, 08, 2026
Price: $525,000
Living Area: 1,785 Sq. Ft.
CHESTERTOWN, MD | Pending
Listed: May, 08, 2026
Price: $525,000
Living Area: 1,785 Sq. Ft.
104 CEDAR STREET
CHESTERTOWN, MD | Active
Listed: May, 12, 2026
Price: $2,600
Living Area: 2,612 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: May, 12, 2026
Price: $2,600
Living Area: 2,612 Sq. Ft.
MAP 36 PARCEL 80 WATERTOWER ROAD
CHESTERTOWN, MD | Active
Listed: Jan, 01, 2026
Price: $55,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jan, 01, 2026
Price: $55,000
Living Area: 0 Sq. Ft.
127 WOOD DUCK LANE
CHESTERTOWN, MD | Closed
Listed: May, 20, 2026
Price: $138,000
Living Area: 1,666 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: May, 20, 2026
Price: $138,000
Living Area: 1,666 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.
117 WATER STREET N 1A, 1B, 2A, & 2B
CHESTERTOWN, MD | Active
Listed: Mar, 01, 2026
Price: $1,600,000
Living Area: 5,400 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 01, 2026
Price: $1,600,000
Living Area: 5,400 Sq. Ft.
117 WATER STREET N 1B
CHESTERTOWN, MD | Active
Listed: Mar, 01, 2026
Price: $200,000
Living Area: 700 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 01, 2026
Price: $200,000
Living Area: 700 Sq. Ft.
117 WATER STREET N 1A
CHESTERTOWN, MD | Active
Listed: Mar, 01, 2026
Price: $685,000
Living Area: 3,000 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Mar, 01, 2026
Price: $685,000
Living Area: 3,000 Sq. Ft.
203 HIGH STREET 2
CHESTERTOWN, MD | Closed
Listed: Jan, 05, 2026
Price: $1,600
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 05, 2026
Price: $1,600
Living Area: 0 Sq. Ft.
206 S WATER STREET
CHESTERTOWN, MD | Closed
Listed: Jan, 14, 2026
Price: $549,000
Living Area: 2,008 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 14, 2026
Price: $549,000
Living Area: 2,008 Sq. Ft.
23264 CLARISSA ROAD
CHESTERTOWN, MD | Active Under Contract
Listed: Jun, 12, 2026
Price: $365,000
Living Area: 1,248 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Jun, 12, 2026
Price: $365,000
Living Area: 1,248 Sq. Ft.
423 CALVERT STREET
CHESTERTOWN, MD | Closed
Listed: May, 18, 2026
Price: $185,000
Living Area: 1,136 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: May, 18, 2026
Price: $185,000
Living Area: 1,136 Sq. Ft.
515 WASHINGTON AVENUE
CHESTERTOWN, MD | Active
Listed: Dec, 09, 2021
Price: $795,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Dec, 09, 2021
Price: $795,000
Living Area: 0 Sq. Ft.
