Listings in 21620 - QUEENANNES County, Maryland
Displaying 1 – 200 of 324 Real estate listings
132 PROSPECT ST,CHESTERTOWN,MD,21620,KENT
CHESTERTOWN, MD | Expired
Listed: Jul, 14, 2025
Price: $62,400
Living Area: 910 Sq. Ft.
CHESTERTOWN, MD | Expired
Listed: Jul, 14, 2025
Price: $62,400
Living Area: 910 Sq. Ft.
8706 Elm Rd, Chestertown, MD 21620-4200, United States
CHESTERTOWN, MD | Active
Listed: Apr, 15, 2026
Price: $320,000
Living Area: 1,232 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Apr, 15, 2026
Price: $320,000
Living Area: 1,232 Sq. Ft.
9194 BAYVIEW AVE,CHESTERTOWN,MD,21620,KENT
CHESTERTOWN, MD | Closed
Listed: Jun, 02, 2016
Price: $249,999
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 02, 2016
Price: $249,999
Living Area: 0 Sq. Ft.
21217 Texas Ave
Chestertown, MD | Closed
Listed: Apr, 09, 2026
Price: $244,500
Living Area: 912 Sq. Ft.
Chestertown, MD | Closed
Listed: Apr, 09, 2026
Price: $244,500
Living Area: 912 Sq. Ft.
234 N College Ave
Chestertown, MD | Active
Listed: Jun, 12, 2026
Price: $85,000
Living Area: 1,296 Sq. Ft.
Chestertown, MD | Active
Listed: Jun, 12, 2026
Price: $85,000
Living Area: 1,296 Sq. Ft.
10584 Klamath Rd
Chestertown, MD | Closed
Listed: Mar, 30, 2026
Price: $319,900
Living Area: 0 Sq. Ft.
Chestertown, MD | Closed
Listed: Mar, 30, 2026
Price: $319,900
Living Area: 0 Sq. Ft.
Fish Hatchery Rd
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.
903 Washington Ave #4
Chestertown, MD | Active
Listed: Jul, 13, 2026
Price: $1,350
Living Area: 0 Sq. Ft.
Chestertown, MD | Active
Listed: Jul, 13, 2026
Price: $1,350
Living Area: 0 Sq. Ft.
106 Queen St S
Chestertown, MD | Active
Listed: Mar, 19, 2026
Price: $829,000
Living Area: 2,472 Sq. Ft.
Chestertown, MD | Active
Listed: Mar, 19, 2026
Price: $829,000
Living Area: 2,472 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.
208 Central Dr
Chestertown, MD | Withdrawn
Listed: Apr, 15, 2026
Price: $299,000
Living Area: 1,120 Sq. Ft.
Chestertown, MD | Withdrawn
Listed: Apr, 15, 2026
Price: $299,000
Living Area: 1,120 Sq. Ft.
25475 Turnberry Ct
Chestertown, MD | Closed
Listed: Mar, 26, 2026
Price: $867,000
Living Area: 4,145 Sq. Ft.
Chestertown, MD | Closed
Listed: Mar, 26, 2026
Price: $867,000
Living Area: 4,145 Sq. Ft.
103 Metcalf Rd
Chestertown, MD | Pending
Listed: Apr, 01, 2026
Price: $259,900
Living Area: 1,280 Sq. Ft.
Chestertown, MD | Pending
Listed: Apr, 01, 2026
Price: $259,900
Living Area: 1,280 Sq. Ft.
860 High St
Chestertown, MD | Expired
Listed: Jun, 16, 2024
Price: $860,000
Living Area: 3,114 Sq. Ft.
Chestertown, MD | Expired
Listed: Jun, 16, 2024
Price: $860,000
Living Area: 3,114 Sq. Ft.
Little Harbor Way #1
Chestertown, MD | Expired
Listed: Feb, 01, 2025
Price: $1,800,000
Living Area: 3,540 Sq. Ft.
Chestertown, MD | Expired
Listed: Feb, 01, 2025
Price: $1,800,000
Living Area: 3,540 Sq. Ft.
202 Valley Rd
Chestertown, MD | Closed
Listed: May, 05, 2026
Price: $325,000
Living Area: 1,427 Sq. Ft.
Chestertown, MD | Closed
Listed: May, 05, 2026
Price: $325,000
Living Area: 1,427 Sq. Ft.
104 Maple Ave #3
Chestertown, MD | Closed
Listed: Feb, 26, 2026
Price: $1,520
Living Area: 800 Sq. Ft.
Chestertown, MD | Closed
Listed: Feb, 26, 2026
Price: $1,520
Living Area: 800 Sq. Ft.
21324 Persimmon Dr
Chestertown, MD | Closed
Listed: Mar, 03, 2026
Price: $124,900
Living Area: 1,232 Sq. Ft.
Chestertown, MD | Closed
Listed: Mar, 03, 2026
Price: $124,900
Living Area: 1,232 Sq. Ft.
10230 John Carvill Rd
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 Dr
Chestertown, MD | Closed
Listed: Oct, 31, 2025
Price: $559,000
Living Area: 2,400 Sq. Ft.
Chestertown, MD | Closed
Listed: Oct, 31, 2025
Price: $559,000
Living Area: 2,400 Sq. Ft.
141 Prospect St
Chestertown, MD | Closed
Listed: Jan, 05, 2026
Price: $165,000
Living Area: 1,156 Sq. Ft.
Chestertown, MD | Closed
Listed: Jan, 05, 2026
Price: $165,000
Living Area: 1,156 Sq. Ft.
870 High St #individual Offices
Chestertown, MD | Expired
Listed: Sep, 11, 2024
Price: $425
Living Area: 16,977 Sq. Ft.
Chestertown, MD | Expired
Listed: Sep, 11, 2024
Price: $425
Living Area: 16,977 Sq. Ft.
205 River Rd
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.
Preston Lane
Chestertown, MD | Pending
Listed: Jul, 13, 2026
Price: $525,000
Living Area: 2,824 Sq. Ft.
Chestertown, MD | Pending
Listed: Jul, 13, 2026
Price: $525,000
Living Area: 2,824 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.
10705 MILLBROOK DR,CHESTERTOWN,MD,21620,KENT
CHESTERTOWN, MD | Closed
Listed: Jun, 11, 2025
Price: $399,900
Living Area: 2,106 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 11, 2025
Price: $399,900
Living Area: 2,106 Sq. Ft.
100 Prospect St
Chestertown, MD | Closed
Listed: May, 01, 2026
Price: $215,000
Living Area: 1,373 Sq. Ft.
Chestertown, MD | Closed
Listed: May, 01, 2026
Price: $215,000
Living Area: 1,373 Sq. Ft.
201 ROSIN DR,CHESTERTOWN,MD,21620,QUEEN ANNES
CHESTERTOWN, MD | Closed
Listed: May, 09, 2005
Price: $260,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: May, 09, 2005
Price: $260,000
Living Area: 0 Sq. Ft.
233 Merganser Dr
Chestertown, MD | Active
Listed: Jul, 12, 2026
Price: $60,000
Living Area: 0 Sq. Ft.
Chestertown, MD | Active
Listed: Jul, 12, 2026
Price: $60,000
Living Area: 0 Sq. Ft.
101 S Mill St
Chestertown, MD | Active Under Contract
Listed: Jun, 01, 2026
Price: $515,000
Living Area: 1,476 Sq. Ft.
Chestertown, MD | Active Under Contract
Listed: Jun, 01, 2026
Price: $515,000
Living Area: 1,476 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.
106 Landing Ln
Chestertown, MD | Active
Listed: Nov, 07, 2025
Price: $799,900
Living Area: 2,092 Sq. Ft.
Chestertown, MD | Active
Listed: Nov, 07, 2025
Price: $799,900
Living Area: 2,092 Sq. Ft.
#35 Landing Ln
Chestertown, MD | Active
Listed: Dec, 04, 2025
Price: $786,900
Living Area: 1,964 Sq. Ft.
Chestertown, MD | Active
Listed: Dec, 04, 2025
Price: $786,900
Living Area: 1,964 Sq. Ft.
Little Harbor Way #1
Chestertown, MD | Active
Listed: Sep, 30, 2025
Price: $1,459,000
Living Area: 2,231 Sq. Ft.
Chestertown, MD | Active
Listed: Sep, 30, 2025
Price: $1,459,000
Living Area: 2,231 Sq. Ft.
201 N Lynchburg St
Chestertown, MD | Active
Listed: Dec, 31, 2025
Price: $500,000
Living Area: 2,045 Sq. Ft.
Chestertown, MD | Active
Listed: Dec, 31, 2025
Price: $500,000
Living Area: 2,045 Sq. Ft.
104 Maple Ave #4
Chestertown, MD | Active
Listed: Jul, 05, 2026
Price: $1,820
Living Area: 900 Sq. Ft.
Chestertown, MD | Active
Listed: Jul, 05, 2026
Price: $1,820
Living Area: 900 Sq. Ft.
109 Wilton Rd
Chestertown, MD | Expired
Listed: Nov, 22, 2024
Price: $344,900
Living Area: 1,392 Sq. Ft.
Chestertown, MD | Expired
Listed: Nov, 22, 2024
Price: $344,900
Living Area: 1,392 Sq. Ft.
7501 Church Hill Rd #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.
109 S College Ave
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.
23416 Cloquet Rd
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.
109 Wilton Rd
Chestertown, MD | Canceled
Listed: Mar, 02, 2026
Price: $344,900
Living Area: 1,392 Sq. Ft.
Chestertown, MD | Canceled
Listed: Mar, 02, 2026
Price: $344,900
Living Area: 1,392 Sq. Ft.
103 Maple Ave
Chestertown, MD | Active Under Contract
Listed: Jun, 10, 2026
Price: $615,000
Living Area: 4,536 Sq. Ft.
Chestertown, MD | Active Under Contract
Listed: Jun, 10, 2026
Price: $615,000
Living Area: 4,536 Sq. Ft.
Sandy Bottom Rd
Chestertown, MD | Active
Listed: May, 14, 2026
Price: $49,000
Living Area: 0 Sq. Ft.
Chestertown, MD | Active
Listed: May, 14, 2026
Price: $49,000
Living Area: 0 Sq. Ft.
104 Maple Ave
Chestertown, MD | Closed
Listed: Feb, 16, 2022
Price: $725,000
Living Area: 5,472 Sq. Ft.
Chestertown, MD | Closed
Listed: Feb, 16, 2022
Price: $725,000
Living Area: 5,472 Sq. Ft.
144 Prospect St
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.
10781 Fermoy Rd
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.
107 Metcalf Rd
Chestertown, MD | Closed
Listed: Mar, 01, 2026
Price: $259,900
Living Area: 1,200 Sq. Ft.
Chestertown, MD | Closed
Listed: Mar, 01, 2026
Price: $259,900
Living Area: 1,200 Sq. Ft.
113 Pear Tree Point Rd
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.
304 Hadaway Dr
Chestertown, MD | Closed
Listed: Apr, 30, 2026
Price: $300,000
Living Area: 1,325 Sq. Ft.
Chestertown, MD | Closed
Listed: Apr, 30, 2026
Price: $300,000
Living Area: 1,325 Sq. Ft.
860 High St
Chestertown, MD | Expired
Listed: Mar, 22, 2024
Price: $3,000
Living Area: 16,977 Sq. Ft.
Chestertown, MD | Expired
Listed: Mar, 22, 2024
Price: $3,000
Living Area: 16,977 Sq. Ft.
10720 Foreston Rd
Chestertown, MD | Pending
Listed: Jun, 12, 2026
Price: $309,000
Living Area: 1,412 Sq. Ft.
Chestertown, MD | Pending
Listed: Jun, 12, 2026
Price: $309,000
Living Area: 1,412 Sq. Ft.
117 Water St 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.
240 Merganser Dr
Chestertown, MD | Active Under Contract
Listed: Apr, 13, 2026
Price: $365,000
Living Area: 1,120 Sq. Ft.
Chestertown, MD | Active Under Contract
Listed: Apr, 13, 2026
Price: $365,000
Living Area: 1,120 Sq. Ft.
533 Round Top Rd
Chestertown, MD | Coming Soon
Listed: Jul, 19, 2026
Price: $225,000
Living Area: 1,800 Sq. Ft.
Chestertown, MD | Coming Soon
Listed: Jul, 19, 2026
Price: $225,000
Living Area: 1,800 Sq. Ft.
7844 Chester Ct
Chestertown, MD | Closed
Listed: Oct, 08, 2025
Price: $640,000
Living Area: 3,248 Sq. Ft.
Chestertown, MD | Closed
Listed: Oct, 08, 2025
Price: $640,000
Living Area: 3,248 Sq. Ft.
25750 Collins Ave
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.
206 N Mill St
Chestertown, MD | Active
Listed: Jul, 28, 2026
Price: $1,850
Living Area: 1,520 Sq. Ft.
Chestertown, MD | Active
Listed: Jul, 28, 2026
Price: $1,850
Living Area: 1,520 Sq. Ft.
123 Trafford Dr
Chestertown, MD | Coming Soon
Listed: Aug, 12, 2026
Price: $375,000
Living Area: 2,504 Sq. Ft.
Chestertown, MD | Coming Soon
Listed: Aug, 12, 2026
Price: $375,000
Living Area: 2,504 Sq. Ft.
8620 Park Dr
Chestertown, MD | Active
Listed: Oct, 25, 2025
Price: $489,900
Living Area: 2,524 Sq. Ft.
Chestertown, MD | Active
Listed: Oct, 25, 2025
Price: $489,900
Living Area: 2,524 Sq. Ft.
104 Church Aly
Chestertown, MD | Coming Soon
Listed: Aug, 06, 2026
Price: $440,000
Living Area: 1,058 Sq. Ft.
Chestertown, MD | Coming Soon
Listed: Aug, 06, 2026
Price: $440,000
Living Area: 1,058 Sq. Ft.
102 Flying Cloud Dr
Chestertown, MD | Closed
Listed: May, 19, 2026
Price: $329,900
Living Area: 1,896 Sq. Ft.
Chestertown, MD | Closed
Listed: May, 19, 2026
Price: $329,900
Living Area: 1,896 Sq. Ft.
522 High St
Chestertown, MD | Active
Listed: May, 28, 2026
Price: $289,900
Living Area: 1,518 Sq. Ft.
Chestertown, MD | Active
Listed: May, 28, 2026
Price: $289,900
Living Area: 1,518 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.
8796 Maryland Pkwy
Chestertown, MD | Active
Listed: May, 26, 2026
Price: $1,495,000
Living Area: 4,776 Sq. Ft.
Chestertown, MD | Active
Listed: May, 26, 2026
Price: $1,495,000
Living Area: 4,776 Sq. Ft.
8796 Maryland Pkwy
Chestertown, MD | Active
Listed: Jun, 02, 2026
Price: $1,495,000
Living Area: 5,000 Sq. Ft.
Chestertown, MD | Active
Listed: Jun, 02, 2026
Price: $1,495,000
Living Area: 5,000 Sq. Ft.
101 S College Ave
Chestertown, MD | Coming Soon
Listed: Aug, 10, 2026
Price: $369,000
Living Area: 1,036 Sq. Ft.
Chestertown, MD | Coming Soon
Listed: Aug, 10, 2026
Price: $369,000
Living Area: 1,036 Sq. Ft.
10540 Tonopah Rd
Chestertown, MD | Active
Listed: Aug, 01, 2026
Price: $279,000
Living Area: 1,404 Sq. Ft.
Chestertown, MD | Active
Listed: Aug, 01, 2026
Price: $279,000
Living Area: 1,404 Sq. Ft.
202 Pine St
Chestertown, MD | Active Under Contract
Listed: Jul, 28, 2026
Price: $205,000
Living Area: 1,341 Sq. Ft.
Chestertown, MD | Active Under Contract
Listed: Jul, 28, 2026
Price: $205,000
Living Area: 1,341 Sq. Ft.
311 Devon Dr
Chestertown, MD | Closed
Listed: Nov, 21, 2025
Price: $475,000
Living Area: 3,504 Sq. Ft.
Chestertown, MD | Closed
Listed: Nov, 21, 2025
Price: $475,000
Living Area: 3,504 Sq. Ft.
128 N Queen St
Chestertown, MD | Expired
Listed: Apr, 04, 2024
Price: $599,000
Living Area: 3,497 Sq. Ft.
Chestertown, MD | Expired
Listed: Apr, 04, 2024
Price: $599,000
Living Area: 3,497 Sq. Ft.
128 N Queen St
Chestertown, MD | Expired
Listed: Apr, 04, 2024
Price: $599,000
Living Area: 3,497 Sq. Ft.
Chestertown, MD | Expired
Listed: Apr, 04, 2024
Price: $599,000
Living Area: 3,497 Sq. Ft.
128 N Queen St #4
Chestertown, MD | Expired
Listed: Jan, 27, 2025
Price: $1,500
Living Area: 800 Sq. Ft.
Chestertown, MD | Expired
Listed: Jan, 27, 2025
Price: $1,500
Living Area: 800 Sq. Ft.
115 Metcalf Rd
Chestertown, MD | Active
Listed: Jul, 13, 2026
Price: $259,900
Living Area: 1,280 Sq. Ft.
Chestertown, MD | Active
Listed: Jul, 13, 2026
Price: $259,900
Living Area: 1,280 Sq. Ft.
9816 Fairlee Rd, Chestertown, MD 21620-3821, United States
CHESTERTOWN, MD | Closed
Listed: Apr, 23, 2026
Price: $535,000
Living Area: 1,624 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Apr, 23, 2026
Price: $535,000
Living Area: 1,624 Sq. Ft.
200 High St, Chestertown, MD 21620-1586, United States
CHESTERTOWN, MD | Active
Listed: Jul, 12, 2026
Price: $2,300,000
Living Area: 6,918 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jul, 12, 2026
Price: $2,300,000
Living Area: 6,918 Sq. Ft.
102 Little Harbor Way
Chestertown, MD | Active
Listed: Dec, 03, 2025
Price: $839,500
Living Area: 1,964 Sq. Ft.
Chestertown, MD | Active
Listed: Dec, 03, 2025
Price: $839,500
Living Area: 1,964 Sq. Ft.
108 Little Harbor Way
Chestertown, MD | Active
Listed: Nov, 10, 2025
Price: $635,000
Living Area: 0 Sq. Ft.
Chestertown, MD | Active
Listed: Nov, 10, 2025
Price: $635,000
Living Area: 0 Sq. Ft.
8730 Georgetown Rd
Chestertown, MD | Canceled
Listed: Apr, 27, 2007
Price: $125,000
Living Area: 0 Sq. Ft.
Chestertown, MD | Canceled
Listed: Apr, 27, 2007
Price: $125,000
Living Area: 0 Sq. Ft.
870 High St #individual Offices
Chestertown, MD | Active
Listed: Mar, 18, 2026
Price: $250
Living Area: 15,986 Sq. Ft.
Chestertown, MD | Active
Listed: Mar, 18, 2026
Price: $250
Living Area: 15,986 Sq. Ft.
Montgomery Avenue
Chestertown, MD | Active
Listed: Dec, 06, 2023
Price: $40,000
Living Area: 0 Sq. Ft.
Chestertown, MD | Active
Listed: Dec, 06, 2023
Price: $40,000
Living Area: 0 Sq. Ft.
704 Truslow Rd
Chestertown, MD | Closed
Listed: Mar, 26, 2026
Price: $440,000
Living Area: 2,060 Sq. Ft.
Chestertown, MD | Closed
Listed: Mar, 26, 2026
Price: $440,000
Living Area: 2,060 Sq. Ft.
104 Acorn Dr
Chestertown, MD | Active
Listed: Jun, 02, 2026
Price: $275,000
Living Area: 1,900 Sq. Ft.
Chestertown, MD | Active
Listed: Jun, 02, 2026
Price: $275,000
Living Area: 1,900 Sq. Ft.
200 Manor Ave
Chestertown, MD | Active
Listed: Jul, 10, 2026
Price: $325,000
Living Area: 2,198 Sq. Ft.
Chestertown, MD | Active
Listed: Jul, 10, 2026
Price: $325,000
Living Area: 2,198 Sq. Ft.
103 Sutton Way
Chestertown, MD | Active
Listed: Nov, 03, 2025
Price: $550,000
Living Area: 3,816 Sq. Ft.
Chestertown, MD | Active
Listed: Nov, 03, 2025
Price: $550,000
Living Area: 3,816 Sq. Ft.
Georgetown Rd 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.
110 S Queen St
Chestertown, MD | Closed
Listed: May, 04, 2026
Price: $525,000
Living Area: 778 Sq. Ft.
Chestertown, MD | Closed
Listed: May, 04, 2026
Price: $525,000
Living Area: 778 Sq. Ft.
215 Fairview Dr
Chestertown, MD | Closed
Listed: Apr, 25, 2026
Price: $425,000
Living Area: 1,784 Sq. Ft.
Chestertown, MD | Closed
Listed: Apr, 25, 2026
Price: $425,000
Living Area: 1,784 Sq. Ft.
305 Roosevelt Dr
Chestertown, MD | Active
Listed: Jul, 14, 2026
Price: $60,000
Living Area: 0 Sq. Ft.
Chestertown, MD | Active
Listed: Jul, 14, 2026
Price: $60,000
Living Area: 0 Sq. Ft.
407 High St
Chestertown, MD | Pending
Listed: May, 03, 2026
Price: $798,000
Living Area: 3,047 Sq. Ft.
Chestertown, MD | Pending
Listed: May, 03, 2026
Price: $798,000
Living Area: 3,047 Sq. Ft.
21217 Texas Ave
Chestertown, MD | Closed
Listed: Nov, 11, 2015
Price: $99,900
Living Area: 912 Sq. Ft.
Chestertown, MD | Closed
Listed: Nov, 11, 2015
Price: $99,900
Living Area: 912 Sq. Ft.
10087 John Carvill Rd
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.
114 Chester Vw
Chestertown, MD | Closed
Listed: Jun, 03, 2026
Price: $1,650,000
Living Area: 2,064 Sq. Ft.
Chestertown, MD | Closed
Listed: Jun, 03, 2026
Price: $1,650,000
Living Area: 2,064 Sq. Ft.
119 Darden Rd
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.
21363 Lynn Ln
Chestertown, MD | Closed
Listed: Apr, 27, 2026
Price: $205,000
Living Area: 1,314 Sq. Ft.
Chestertown, MD | Closed
Listed: Apr, 27, 2026
Price: $205,000
Living Area: 1,314 Sq. Ft.
24775 Langford Rd
Chestertown, MD | Expired
Listed: Dec, 27, 2025
Price: $319,900
Living Area: 1,008 Sq. Ft.
Chestertown, MD | Expired
Listed: Dec, 27, 2025
Price: $319,900
Living Area: 1,008 Sq. Ft.
119 Darden Rd
Chestertown, MD | Expired
Listed: Sep, 10, 2025
Price: $315,000
Living Area: 1,424 Sq. Ft.
Chestertown, MD | Expired
Listed: Sep, 10, 2025
Price: $315,000
Living Area: 1,424 Sq. Ft.
896 Washington Ave
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.
104 Conley Dr
Chestertown, MD | Active
Listed: Jun, 04, 2026
Price: $239,900
Living Area: 1,280 Sq. Ft.
Chestertown, MD | Active
Listed: Jun, 04, 2026
Price: $239,900
Living Area: 1,280 Sq. Ft.
104 Maple Ave
Chestertown, MD | Active
Listed: Jul, 28, 2026
Price: $650,000
Living Area: 7,296 Sq. Ft.
Chestertown, MD | Active
Listed: Jul, 28, 2026
Price: $650,000
Living Area: 7,296 Sq. Ft.
Lot 9 Prestwick Dr
Chestertown, MD | Pending
Listed: May, 01, 2024
Price: $185,000
Living Area: 0 Sq. Ft.
Chestertown, MD | Pending
Listed: May, 01, 2024
Price: $185,000
Living Area: 0 Sq. Ft.
7903 Radcliffe Rd
Chestertown, MD | Pending
Listed: Jul, 31, 2026
Price: $625,000
Living Area: 4,037 Sq. Ft.
Chestertown, MD | Pending
Listed: Jul, 31, 2026
Price: $625,000
Living Area: 4,037 Sq. Ft.
7828 Country Club Ln
Chestertown, MD | Active
Listed: Jun, 23, 2026
Price: $799,000
Living Area: 2,857 Sq. Ft.
Chestertown, MD | Active
Listed: Jun, 23, 2026
Price: $799,000
Living Area: 2,857 Sq. Ft.
216 Birch Run Rd
Chestertown, MD | Coming Soon
Listed: Jul, 08, 2026
Price: $750,000
Living Area: 2,176 Sq. Ft.
Chestertown, MD | Coming Soon
Listed: Jul, 08, 2026
Price: $750,000
Living Area: 2,176 Sq. Ft.
21324 Persimmon Dr
Chestertown, MD | Active
Listed: Jun, 29, 2026
Price: $189,000
Living Area: 1,232 Sq. Ft.
Chestertown, MD | Active
Listed: Jun, 29, 2026
Price: $189,000
Living Area: 1,232 Sq. Ft.
202 Royston Shores Rd
Chestertown, MD | Closed
Listed: Jun, 01, 2026
Price: $1,200,000
Living Area: 2,292 Sq. Ft.
Chestertown, MD | Closed
Listed: Jun, 01, 2026
Price: $1,200,000
Living Area: 2,292 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.
E GEORGETOWN RD,CHESTERTOWN,MD,21620,KENT
CHESTERTOWN, MD | Active
Listed: May, 21, 2025
Price: $60,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: May, 21, 2025
Price: $60,000
Living Area: 0 Sq. Ft.
221 Dutchess Rd, Chestertown, MD 21620-2211, United States
CHESTERTOWN, MD | Closed
Listed: Jun, 15, 2026
Price: $228,000
Living Area: 2,260 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 15, 2026
Price: $228,000
Living Area: 2,260 Sq. Ft.
213 Byford Dr, Chestertown, MD 21620-1643, United States
CHESTERTOWN, MD | Active
Listed: Jun, 02, 2026
Price: $380,000
Living Area: 1,277 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Jun, 02, 2026
Price: $380,000
Living Area: 1,277 Sq. Ft.
218 CAMELOT DR,CHESTERTOWN,MD,21620,KENT
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.
107 Flying Cloud Dr, Chestertown, MD 21620-1186, United States
CHESTERTOWN, MD | Active Under Contract
Listed: Apr, 25, 2026
Price: $375,000
Living Area: 2,534 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Apr, 25, 2026
Price: $375,000
Living Area: 2,534 Sq. Ft.
315 HIGH ST #201,CHESTERTOWN,MD,21620,KENT
CHESTERTOWN, MD | Active
Listed: Sep, 10, 2024
Price: $2,900
Living Area: 19,416 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Sep, 10, 2024
Price: $2,900
Living Area: 19,416 Sq. Ft.
120 PINE CHIP RD,CHESTERTOWN,MD,21620,QUEEN ANNES
CHESTERTOWN, MD | Closed
Listed: Jan, 03, 2004
Price: $1,100
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jan, 03, 2004
Price: $1,100
Living Area: 0 Sq. Ft.
7464 CEDAR RD,CHESTERTOWN,MD,21620,KENT
CHESTERTOWN, MD | Closed
Listed: Jun, 18, 2004
Price: $110,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jun, 18, 2004
Price: $110,000
Living Area: 0 Sq. Ft.
521 N Kent St
Chestertown, MD | Closed
Listed: May, 13, 2026
Price: $385,000
Living Area: 1,934 Sq. Ft.
Chestertown, MD | Closed
Listed: May, 13, 2026
Price: $385,000
Living Area: 1,934 Sq. Ft.
848 High St
Chestertown, MD | Closed
Listed: Mar, 28, 2006
Price: $850,000
Living Area: 44,000 Sq. Ft.
Chestertown, MD | Closed
Listed: Mar, 28, 2006
Price: $850,000
Living Area: 44,000 Sq. Ft.
870 High St #2-3
Chestertown, MD | Expired
Listed: Mar, 25, 2024
Price: $18
Living Area: 16,977 Sq. Ft.
Chestertown, MD | Expired
Listed: Mar, 25, 2024
Price: $18
Living Area: 16,977 Sq. Ft.
112 Silver Heel Dr
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.
870 High St
Chestertown, MD | Expired
Listed: Jun, 16, 2024
Price: $1,870,000
Living Area: 16,977 Sq. Ft.
Chestertown, MD | Expired
Listed: Jun, 16, 2024
Price: $1,870,000
Living Area: 16,977 Sq. Ft.
10594 Millbrook Dr
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.
304 Hadaway Dr
Chestertown, MD | Withdrawn
Listed: Oct, 28, 2025
Price: $350,000
Living Area: 1,325 Sq. Ft.
Chestertown, MD | Withdrawn
Listed: Oct, 28, 2025
Price: $350,000
Living Area: 1,325 Sq. Ft.
201 River Rd #xx
Chestertown, MD | Canceled
Listed: Oct, 18, 1999
Price: $219,900
Living Area: 0 Sq. Ft.
Chestertown, MD | Canceled
Listed: Oct, 18, 1999
Price: $219,900
Living Area: 0 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.
306 Roosevelt Dr
Chestertown, MD | Closed
Listed: Jan, 16, 2024
Price: $250,000
Living Area: 1,152 Sq. Ft.
Chestertown, MD | Closed
Listed: Jan, 16, 2024
Price: $250,000
Living Area: 1,152 Sq. Ft.
222 Dutchess Rd
Chestertown, MD | Active
Listed: Oct, 03, 2025
Price: $320,000
Living Area: 1,096 Sq. Ft.
Chestertown, MD | Active
Listed: Oct, 03, 2025
Price: $320,000
Living Area: 1,096 Sq. Ft.
201 River Rd
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.
22470 Fairgale Farm Ln
Chestertown, MD | Active
Listed: May, 02, 2026
Price: $1,450,000
Living Area: 4,257 Sq. Ft.
Chestertown, MD | Active
Listed: May, 02, 2026
Price: $1,450,000
Living Area: 4,257 Sq. Ft.
Buck Neck Landing Rd
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.
104 Maple Ave
Chestertown, MD | Canceled
Listed: Mar, 04, 2026
Price: $1,350,000
Living Area: 7,296 Sq. Ft.
Chestertown, MD | Canceled
Listed: Mar, 04, 2026
Price: $1,350,000
Living Area: 7,296 Sq. Ft.
201 Birch Run Rd
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.
720 Deep Landing Rd
Chestertown, MD | Closed
Listed: Apr, 02, 2026
Price: $369,900
Living Area: 1,271 Sq. Ft.
Chestertown, MD | Closed
Listed: Apr, 02, 2026
Price: $369,900
Living Area: 1,271 Sq. Ft.
112 Elm St
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.
7514 Muirfield Dr
Chestertown, MD | Expired
Listed: Jun, 20, 2025
Price: $797,000
Living Area: 2,522 Sq. Ft.
Chestertown, MD | Expired
Listed: Jun, 20, 2025
Price: $797,000
Living Area: 2,522 Sq. Ft.
121 Metcalf Rd
Chestertown, MD | Active
Listed: Jun, 15, 2026
Price: $264,900
Living Area: 0 Sq. Ft.
Chestertown, MD | Active
Listed: Jun, 15, 2026
Price: $264,900
Living Area: 0 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.
1010 Twin Ct
Chestertown, MD | Active
Listed: May, 28, 2026
Price: $2,250
Living Area: 1,476 Sq. Ft.
Chestertown, MD | Active
Listed: May, 28, 2026
Price: $2,250
Living Area: 1,476 Sq. Ft.
21125 Iowa Ave
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.
115 Acorn Dr
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.
126 Char Nor Manor Blvd
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.
Buck Neck Landing Rd
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.
351 Calvert St
Chestertown, MD | Closed
Listed: Jun, 29, 2026
Price: $2,000
Living Area: 1,122 Sq. Ft.
Chestertown, MD | Closed
Listed: Jun, 29, 2026
Price: $2,000
Living Area: 1,122 Sq. Ft.
109 Metcalf Rd
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.
108 Oak Leaf Dr
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.
2032 Pondtown Rd
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.
101 Coleman Dr
Chestertown, MD | Canceled
Listed: Mar, 25, 2026
Price: $519,900
Living Area: 2,268 Sq. Ft.
Chestertown, MD | Canceled
Listed: Mar, 25, 2026
Price: $519,900
Living Area: 2,268 Sq. Ft.
Fish Hatchery Rd
Chestertown, MD | Active
Listed: Jun, 21, 2023
Price: $37,000
Living Area: 0 Sq. Ft.
Chestertown, MD | Active
Listed: Jun, 21, 2023
Price: $37,000
Living Area: 0 Sq. Ft.
1014 Twin Ct
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.
7761 Broad Neck Rd
Chestertown, MD | Closed
Listed: Feb, 26, 2026
Price: $1,500,000
Living Area: 2,700 Sq. Ft.
Chestertown, MD | Closed
Listed: Feb, 26, 2026
Price: $1,500,000
Living Area: 2,700 Sq. Ft.
103 Trafford Dr
Chestertown, MD | Withdrawn
Listed: Apr, 17, 2026
Price: $399,900
Living Area: 1,944 Sq. Ft.
Chestertown, MD | Withdrawn
Listed: Apr, 17, 2026
Price: $399,900
Living Area: 1,944 Sq. Ft.
8886 Georgetown Rd
Chestertown, MD | Active
Listed: May, 31, 2026
Price: $69,900
Living Area: 0 Sq. Ft.
Chestertown, MD | Active
Listed: May, 31, 2026
Price: $69,900
Living Area: 0 Sq. Ft.
25416 Commerce Ln
Chestertown, MD | Active
Listed: Dec, 06, 2025
Price: $1,100,000
Living Area: 5,600 Sq. Ft.
Chestertown, MD | Active
Listed: Dec, 06, 2025
Price: $1,100,000
Living Area: 5,600 Sq. Ft.
24295 Langford Rd
Chestertown, MD | Hold
Listed: Apr, 09, 2026
Price: $430,000
Living Area: 1,857 Sq. Ft.
Chestertown, MD | Hold
Listed: Apr, 09, 2026
Price: $430,000
Living Area: 1,857 Sq. Ft.
231 Richard Dr
Chestertown, MD | Closed
Listed: Nov, 08, 2025
Price: $1,150,000
Living Area: 2,956 Sq. Ft.
Chestertown, MD | Closed
Listed: Nov, 08, 2025
Price: $1,150,000
Living Area: 2,956 Sq. Ft.
117 Water St 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.
240 Round Top Rd
Chestertown, MD | Coming Soon
Listed: Aug, 05, 2026
Price: $295,000
Living Area: 1,132 Sq. Ft.
Chestertown, MD | Coming Soon
Listed: Aug, 05, 2026
Price: $295,000
Living Area: 1,132 Sq. Ft.
129 Trafford Dr
Chestertown, MD | Expired
Listed: Sep, 06, 2019
Price: $324,900
Living Area: 3,001 Sq. Ft.
Chestertown, MD | Expired
Listed: Sep, 06, 2019
Price: $324,900
Living Area: 3,001 Sq. Ft.
129 Trafford Dr
Chestertown, MD | Expired
Listed: Nov, 06, 2019
Price: $319,900
Living Area: 3,001 Sq. Ft.
Chestertown, MD | Expired
Listed: Nov, 06, 2019
Price: $319,900
Living Area: 3,001 Sq. Ft.
129 Trafford Dr
Chestertown, MD | Active
Listed: Jul, 29, 2026
Price: $480,000
Living Area: 3,176 Sq. Ft.
Chestertown, MD | Active
Listed: Jul, 29, 2026
Price: $480,000
Living Area: 3,176 Sq. Ft.
129 Trafford Dr
Chestertown, MD | Expired
Listed: Sep, 25, 2019
Price: $324,900
Living Area: 3,001 Sq. Ft.
Chestertown, MD | Expired
Listed: Sep, 25, 2019
Price: $324,900
Living Area: 3,001 Sq. Ft.
129 Trafford Dr
Chestertown, MD | Expired
Listed: Oct, 10, 2019
Price: $319,900
Living Area: 3,001 Sq. Ft.
Chestertown, MD | Expired
Listed: Oct, 10, 2019
Price: $319,900
Living Area: 3,001 Sq. Ft.
129 Trafford Dr
Chestertown, MD | Closed
Listed: Dec, 22, 2019
Price: $314,900
Living Area: 3,001 Sq. Ft.
Chestertown, MD | Closed
Listed: Dec, 22, 2019
Price: $314,900
Living Area: 3,001 Sq. Ft.
611 Cannon St
Chestertown, MD | Active Under Contract
Listed: Nov, 05, 2025
Price: $275,000
Living Area: 920 Sq. Ft.
Chestertown, MD | Active Under Contract
Listed: Nov, 05, 2025
Price: $275,000
Living Area: 920 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.
110 Prospect St
Chestertown, MD | Pending
Listed: Jun, 08, 2026
Price: $54,900
Living Area: 2,210 Sq. Ft.
Chestertown, MD | Pending
Listed: Jun, 08, 2026
Price: $54,900
Living Area: 2,210 Sq. Ft.
24581 Willow Oak Ln
Chestertown, MD | Pending
Listed: Apr, 01, 2026
Price: $229,990
Living Area: 1,352 Sq. Ft.
Chestertown, MD | Pending
Listed: Apr, 01, 2026
Price: $229,990
Living Area: 1,352 Sq. Ft.
110 S Mill St
Chestertown, MD | Expired
Listed: Aug, 13, 2025
Price: $745,000
Living Area: 2,492 Sq. Ft.
Chestertown, MD | Expired
Listed: Aug, 13, 2025
Price: $745,000
Living Area: 2,492 Sq. Ft.
21425 Belair Ave
Chestertown, MD | Closed
Listed: Aug, 14, 2026
Price: $765,000
Living Area: 2,758 Sq. Ft.
Chestertown, MD | Closed
Listed: Aug, 14, 2026
Price: $765,000
Living Area: 2,758 Sq. Ft.
7989 Quaker Neck Rd
Chestertown, MD | Closed
Listed: Aug, 27, 2025
Price: $2,200,000
Living Area: 4,305 Sq. Ft.
Chestertown, MD | Closed
Listed: Aug, 27, 2025
Price: $2,200,000
Living Area: 4,305 Sq. Ft.
109 Cedar St
Chestertown, MD | Closed
Listed: Jul, 08, 2026
Price: $325,000
Living Area: 1,397 Sq. Ft.
Chestertown, MD | Closed
Listed: Jul, 08, 2026
Price: $325,000
Living Area: 1,397 Sq. Ft.
