Listings in 21620 - Kent County, Maryland
Displaying 201 – 400 of 334 Real estate listings
Fish Hatchery Rd
Chestertown, MD | Active
Listed: Jun, 21, 2023
Price: $18,500
Living Area: 0 Sq. Ft.
Chestertown, MD | Active
Listed: Jun, 21, 2023
Price: $18,500
Living Area: 0 Sq. Ft.
8276 Broad Neck Rd
Chestertown, MD | Hold
Listed: Sep, 14, 2026
Price: $1,295,000
Living Area: 3,383 Sq. Ft.
Chestertown, MD | Hold
Listed: Sep, 14, 2026
Price: $1,295,000
Living Area: 3,383 Sq. Ft.
204 S Water St
Chestertown, MD | Active Under Contract
Listed: Mar, 10, 2025
Price: $565,000
Living Area: 1,306 Sq. Ft.
Chestertown, MD | Active Under Contract
Listed: Mar, 10, 2025
Price: $565,000
Living Area: 1,306 Sq. Ft.
1003 Twin Ct
Chestertown, MD | Canceled
Listed: Aug, 19, 2026
Price: $499,900
Living Area: 2,076 Sq. Ft.
Chestertown, MD | Canceled
Listed: Aug, 19, 2026
Price: $499,900
Living Area: 2,076 Sq. Ft.
104 Maple Ave #3
Chestertown, MD | Closed
Listed: Sep, 09, 2026
Price: $1,495
Living Area: 600 Sq. Ft.
Chestertown, MD | Closed
Listed: Sep, 09, 2026
Price: $1,495
Living Area: 600 Sq. Ft.
203 Manor Ave
Chestertown, MD | Active
Listed: Oct, 11, 2026
Price: $296,000
Living Area: 1,248 Sq. Ft.
Chestertown, MD | Active
Listed: Oct, 11, 2026
Price: $296,000
Living Area: 1,248 Sq. Ft.
10 Cedar Chase Ct
Chestertown, MD | Active
Listed: Sep, 22, 2026
Price: $495,000
Living Area: 1,656 Sq. Ft.
Chestertown, MD | Active
Listed: Sep, 22, 2026
Price: $495,000
Living Area: 1,656 Sq. Ft.
329 Union Church Rd
Chestertown, MD | Active
Listed: Sep, 02, 2026
Price: $568,900
Living Area: 2,464 Sq. Ft.
Chestertown, MD | Active
Listed: Sep, 02, 2026
Price: $568,900
Living Area: 2,464 Sq. Ft.
8820 Cumberland St
Chestertown, MD | Active
Listed: Oct, 01, 2026
Price: $312,500
Living Area: 1,080 Sq. Ft.
Chestertown, MD | Active
Listed: Oct, 01, 2026
Price: $312,500
Living Area: 1,080 Sq. Ft.
200 Manor Ave
Chestertown, MD | Active Under Contract
Listed: Jul, 10, 2026
Price: $325,000
Living Area: 2,198 Sq. Ft.
Chestertown, MD | Active Under Contract
Listed: Jul, 10, 2026
Price: $325,000
Living Area: 2,198 Sq. Ft.
1010 Twin Ct
Chestertown, MD | Expired
Listed: Mar, 19, 2026
Price: $2,500
Living Area: 1,476 Sq. Ft.
Chestertown, MD | Expired
Listed: Mar, 19, 2026
Price: $2,500
Living Area: 1,476 Sq. Ft.
1010 Twin Ct
Chestertown, MD | Pending
Listed: May, 28, 2026
Price: $2,100
Living Area: 1,476 Sq. Ft.
Chestertown, MD | Pending
Listed: May, 28, 2026
Price: $2,100
Living Area: 1,476 Sq. Ft.
24775 Langford Rd
Chestertown, MD | Active
Listed: Sep, 01, 2026
Price: $305,000
Living Area: 1,008 Sq. Ft.
Chestertown, MD | Active
Listed: Sep, 01, 2026
Price: $305,000
Living Area: 1,008 Sq. Ft.
7452 POPLAR AVE,CHESTERTOWN,MD,21620,KENT
CHESTERTOWN, MD | Closed
Listed: Apr, 12, 2004
Price: $89,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Apr, 12, 2004
Price: $89,000
Living Area: 0 Sq. Ft.
7456 SHORTALL ST,CHESTERTOWN,MD,21620,KENT
CHESTERTOWN, MD | Closed
Listed: Mar, 21, 2005
Price: $79,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Mar, 21, 2005
Price: $79,000
Living Area: 0 Sq. Ft.
110 S Queen St
Chestertown, MD | Canceled
Listed: May, 08, 2026
Price: $525,000
Living Area: 1,785 Sq. Ft.
Chestertown, MD | Canceled
Listed: May, 08, 2026
Price: $525,000
Living Area: 1,785 Sq. Ft.
22681 Wood Yard Ln
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.
21172 Wyoming Ave
Chestertown, MD | Canceled
Listed: Jun, 05, 2026
Price: $200,000
Living Area: 2,920 Sq. Ft.
Chestertown, MD | Canceled
Listed: Jun, 05, 2026
Price: $200,000
Living Area: 2,920 Sq. Ft.
21172 Wyoming Ave
Chestertown, MD | Closed
Listed: Dec, 06, 1999
Price: $99,500
Living Area: 0 Sq. Ft.
Chestertown, MD | Closed
Listed: Dec, 06, 1999
Price: $99,500
Living Area: 0 Sq. Ft.
#36 Landing Ln
Chestertown, MD | Active
Listed: Dec, 04, 2025
Price: $753,500
Living Area: 1,964 Sq. Ft.
Chestertown, MD | Active
Listed: Dec, 04, 2025
Price: $753,500
Living Area: 1,964 Sq. Ft.
#37 Landing Ln
Chestertown, MD | Active
Listed: Dec, 04, 2025
Price: $765,900
Living Area: 1,964 Sq. Ft.
Chestertown, MD | Active
Listed: Dec, 04, 2025
Price: $765,900
Living Area: 1,964 Sq. Ft.
104 Little Harbor Way
Chestertown, MD | Active
Listed: Nov, 07, 2025
Price: $849,900
Living Area: 1,980 Sq. Ft.
Chestertown, MD | Active
Listed: Nov, 07, 2025
Price: $849,900
Living Area: 1,980 Sq. Ft.
#25 Landing Ln
Chestertown, MD | Active
Listed: Dec, 03, 2025
Price: $1,099,900
Living Area: 2,784 Sq. Ft.
Chestertown, MD | Active
Listed: Dec, 03, 2025
Price: $1,099,900
Living Area: 2,784 Sq. Ft.
104 Landing Ln
Chestertown, MD | Active
Listed: Dec, 03, 2025
Price: $813,900
Living Area: 2,192 Sq. Ft.
Chestertown, MD | Active
Listed: Dec, 03, 2025
Price: $813,900
Living Area: 2,192 Sq. Ft.
201 N Lynchburg St #lots 4, 5, 6 & 7
Chestertown, MD | Active
Listed: Dec, 31, 2025
Price: $300,000
Living Area: 0 Sq. Ft.
Chestertown, MD | Active
Listed: Dec, 31, 2025
Price: $300,000
Living Area: 0 Sq. Ft.
Tonopah Rd.
Chestertown, MD | Active Under Contract
Listed: Aug, 11, 2025
Price: $40,000
Living Area: 0 Sq. Ft.
Chestertown, MD | Active Under Contract
Listed: Aug, 11, 2025
Price: $40,000
Living Area: 0 Sq. Ft.
101 Morgnec Rd
Chestertown, MD | Active
Listed: Feb, 25, 2019
Price: $1,300
Living Area: 785 Sq. Ft.
Chestertown, MD | Active
Listed: Feb, 25, 2019
Price: $1,300
Living Area: 785 Sq. Ft.
Map 36 Parcel 80 Watertower Rd
Chestertown, MD | Active
Listed: May, 18, 2026
Price: $55,000
Living Area: 0 Sq. Ft.
Chestertown, MD | Active
Listed: May, 18, 2026
Price: $55,000
Living Area: 0 Sq. Ft.
Cromwell Clark Rd
Chestertown, MD | Pending
Listed: Apr, 28, 2025
Price: $3,000,000
Living Area: 0 Sq. Ft.
Chestertown, MD | Pending
Listed: Apr, 28, 2025
Price: $3,000,000
Living Area: 0 Sq. Ft.
205 River Rd
Chestertown, MD | Canceled
Listed: Mar, 24, 2026
Price: $899,500
Living Area: 2,877 Sq. Ft.
Chestertown, MD | Canceled
Listed: Mar, 24, 2026
Price: $899,500
Living Area: 2,877 Sq. Ft.
129 Trafford Dr
Chestertown, MD | Expired
Listed: Dec, 05, 2019
Price: $317,500
Living Area: 3,001 Sq. Ft.
Chestertown, MD | Expired
Listed: Dec, 05, 2019
Price: $317,500
Living Area: 3,001 Sq. Ft.
1906 Pondtown Rd
Chestertown, MD | Active
Listed: May, 30, 2026
Price: $110,000
Living Area: 0 Sq. Ft.
Chestertown, MD | Active
Listed: May, 30, 2026
Price: $110,000
Living Area: 0 Sq. Ft.
110 Trafford Dr
Chestertown, MD | Expired
Listed: Dec, 04, 2025
Price: $450,000
Living Area: 2,880 Sq. Ft.
Chestertown, MD | Expired
Listed: Dec, 04, 2025
Price: $450,000
Living Area: 2,880 Sq. Ft.
24607 Chestertown Rd
Chestertown, MD | Expired
Listed: May, 18, 2025
Price: $365,000
Living Area: 2,294 Sq. Ft.
Chestertown, MD | Expired
Listed: May, 18, 2025
Price: $365,000
Living Area: 2,294 Sq. Ft.
116 Harlan Loop
Chestertown, MD | Canceled
Listed: Aug, 18, 2025
Price: $509,000
Living Area: 4,067 Sq. Ft.
Chestertown, MD | Canceled
Listed: Aug, 18, 2025
Price: $509,000
Living Area: 4,067 Sq. Ft.
Haacke Drive Lot 3
Chestertown, MD | Active
Listed: Mar, 23, 2026
Price: $225,000
Living Area: 0 Sq. Ft.
Chestertown, MD | Active
Listed: Mar, 23, 2026
Price: $225,000
Living Area: 0 Sq. Ft.
25440 Learman Rd
Chestertown, MD | Closed
Listed: Apr, 29, 2026
Price: $3,000,000
Living Area: 3,142 Sq. Ft.
Chestertown, MD | Closed
Listed: Apr, 29, 2026
Price: $3,000,000
Living Area: 3,142 Sq. Ft.
1904 Pondtown Rd
Chestertown, MD | Closed
Listed: May, 30, 2026
Price: $265,000
Living Area: 1,967 Sq. Ft.
Chestertown, MD | Closed
Listed: May, 30, 2026
Price: $265,000
Living Area: 1,967 Sq. Ft.
8890 Fairlee Rd
Chestertown, MD | Closed
Listed: Jun, 25, 2026
Price: $2,300
Living Area: 1,232 Sq. Ft.
Chestertown, MD | Closed
Listed: Jun, 25, 2026
Price: $2,300
Living Area: 1,232 Sq. Ft.
601 Washington Ave
Chestertown, MD | Expired
Listed: Nov, 21, 2024
Price: $2,864
Living Area: 13,500 Sq. Ft.
Chestertown, MD | Expired
Listed: Nov, 21, 2024
Price: $2,864
Living Area: 13,500 Sq. Ft.
21146 Montana Ave
Chestertown, MD | Closed
Listed: Jul, 28, 2026
Price: $289,900
Living Area: 1,500 Sq. Ft.
Chestertown, MD | Closed
Listed: Jul, 28, 2026
Price: $289,900
Living Area: 1,500 Sq. Ft.
204 Double Creek Rd
Chestertown, MD | Active Under Contract
Listed: Feb, 01, 2026
Price: $545,000
Living Area: 2,927 Sq. Ft.
Chestertown, MD | Active Under Contract
Listed: Feb, 01, 2026
Price: $545,000
Living Area: 2,927 Sq. Ft.
896 Washington Ave
Chestertown, MD | Active
Listed: Sep, 28, 2026
Price: $325,000
Living Area: 2,000 Sq. Ft.
Chestertown, MD | Active
Listed: Sep, 28, 2026
Price: $325,000
Living Area: 2,000 Sq. Ft.
8999 Orchard Dr
Chestertown, MD | Active Under Contract
Listed: Jul, 20, 2026
Price: $824,900
Living Area: 4,353 Sq. Ft.
Chestertown, MD | Active Under Contract
Listed: Jul, 20, 2026
Price: $824,900
Living Area: 4,353 Sq. Ft.
104 Flying Cloud Dr
Chestertown, MD | Expired
Listed: Mar, 01, 2026
Price: $394,900
Living Area: 2,535 Sq. Ft.
Chestertown, MD | Expired
Listed: Mar, 01, 2026
Price: $394,900
Living Area: 2,535 Sq. Ft.
132 PROSPECT ST,CHESTERTOWN,MD,21620,KENT
CHESTERTOWN, MD | Expired
Listed: Apr, 22, 2025
Price: $99,900
Living Area: 910 Sq. Ft.
CHESTERTOWN, MD | Expired
Listed: Apr, 22, 2025
Price: $99,900
Living Area: 910 Sq. Ft.
132 PROSPECT ST,CHESTERTOWN,MD,21620,KENT
CHESTERTOWN, MD | Expired
Listed: Jun, 06, 2025
Price: $74,900
Living Area: 910 Sq. Ft.
CHESTERTOWN, MD | Expired
Listed: Jun, 06, 2025
Price: $74,900
Living Area: 910 Sq. Ft.
222 Mount Vernon Ave
Chestertown, MD | Withdrawn
Listed: May, 30, 2026
Price: $2,950
Living Area: 1,656 Sq. Ft.
Chestertown, MD | Withdrawn
Listed: May, 30, 2026
Price: $2,950
Living Area: 1,656 Sq. Ft.
214 Silver Heel Rd
Chestertown, MD | Active Under Contract
Listed: May, 04, 2026
Price: $340,000
Living Area: 1,972 Sq. Ft.
Chestertown, MD | Active Under Contract
Listed: May, 04, 2026
Price: $340,000
Living Area: 1,972 Sq. Ft.
201 N Lynchburg St
Chestertown, MD | Active
Listed: Dec, 31, 2025
Price: $750,000
Living Area: 2,045 Sq. Ft.
Chestertown, MD | Active
Listed: Dec, 31, 2025
Price: $750,000
Living Area: 2,045 Sq. Ft.
201 N Lynchburg St
Chestertown, MD | Active
Listed: Dec, 31, 2025
Price: $750,000
Living Area: 3,527 Sq. Ft.
Chestertown, MD | Active
Listed: Dec, 31, 2025
Price: $750,000
Living Area: 3,527 Sq. Ft.
201 N Lynchburg St
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.
202 Waldo Dr
Chestertown, MD | Canceled
Listed: Mar, 23, 2026
Price: $340,000
Living Area: 2,055 Sq. Ft.
Chestertown, MD | Canceled
Listed: Mar, 23, 2026
Price: $340,000
Living Area: 2,055 Sq. Ft.
23043 Bay Shore Spur
Chestertown, MD | Active
Listed: Aug, 01, 2025
Price: $385,000
Living Area: 2,630 Sq. Ft.
Chestertown, MD | Active
Listed: Aug, 01, 2025
Price: $385,000
Living Area: 2,630 Sq. Ft.
139 Prospect St
Chestertown, MD | Closed
Listed: Mar, 13, 2026
Price: $198,000
Living Area: 1,200 Sq. Ft.
Chestertown, MD | Closed
Listed: Mar, 13, 2026
Price: $198,000
Living Area: 1,200 Sq. Ft.
860-Studio High St
Chestertown, MD | Closed
Listed: Jun, 16, 2024
Price: $1,700
Living Area: 16,977 Sq. Ft.
Chestertown, MD | Closed
Listed: Jun, 16, 2024
Price: $1,700
Living Area: 16,977 Sq. Ft.
860-Cafe High St
Chestertown, MD | Closed
Listed: Jun, 16, 2024
Price: $1,500
Living Area: 16,977 Sq. Ft.
Chestertown, MD | Closed
Listed: Jun, 16, 2024
Price: $1,500
Living Area: 16,977 Sq. Ft.
860 & 870 High St
Chestertown, MD | Closed
Listed: Apr, 19, 2024
Price: $375,000
Living Area: 16,977 Sq. Ft.
Chestertown, MD | Closed
Listed: Apr, 19, 2024
Price: $375,000
Living Area: 16,977 Sq. Ft.
870 High St #2
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.
327 Cannon St
Chestertown, MD | Active
Listed: Feb, 04, 2026
Price: $1,300,000
Living Area: 3,740 Sq. Ft.
Chestertown, MD | Active
Listed: Feb, 04, 2026
Price: $1,300,000
Living Area: 3,740 Sq. Ft.
515 Washington Ave
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.
228 Merganser Dr
Chestertown, MD | Closed
Listed: May, 13, 2026
Price: $59,999
Living Area: 0 Sq. Ft.
Chestertown, MD | Closed
Listed: May, 13, 2026
Price: $59,999
Living Area: 0 Sq. Ft.
104 Maple Ave #6
Chestertown, MD | Closed
Listed: Apr, 17, 2026
Price: $1,920
Living Area: 900 Sq. Ft.
Chestertown, MD | Closed
Listed: Apr, 17, 2026
Price: $1,920
Living Area: 900 Sq. Ft.
212 Byford Dr
Chestertown, MD | Closed
Listed: Aug, 13, 2015
Price: $319,000
Living Area: 1,596 Sq. Ft.
Chestertown, MD | Closed
Listed: Aug, 13, 2015
Price: $319,000
Living Area: 1,596 Sq. Ft.
956 Washington Ave
Chestertown, MD | Active
Listed: May, 24, 2026
Price: $275,000
Living Area: 1,248 Sq. Ft.
Chestertown, MD | Active
Listed: May, 24, 2026
Price: $275,000
Living Area: 1,248 Sq. Ft.
7464 Shortall St
Chestertown, MD | Closed
Listed: Oct, 31, 2020
Price: $209,000
Living Area: 1,232 Sq. Ft.
Chestertown, MD | Closed
Listed: Oct, 31, 2020
Price: $209,000
Living Area: 1,232 Sq. Ft.
124 Wilton Rd
Chestertown, MD | Expired
Listed: Sep, 30, 2012
Price: $139,900
Living Area: 0 Sq. Ft.
Chestertown, MD | Expired
Listed: Sep, 30, 2012
Price: $139,900
Living Area: 0 Sq. Ft.
517 Round Top Rd
Chestertown, MD | Closed
Listed: Jun, 19, 2026
Price: $299,900
Living Area: 1,248 Sq. Ft.
Chestertown, MD | Closed
Listed: Jun, 19, 2026
Price: $299,900
Living Area: 1,248 Sq. Ft.
107 Conley Dr
Chestertown, MD | Closed
Listed: Jul, 14, 2026
Price: $240,000
Living Area: 1,140 Sq. Ft.
Chestertown, MD | Closed
Listed: Jul, 14, 2026
Price: $240,000
Living Area: 1,140 Sq. Ft.
226 S Water St
Chestertown, MD | Active
Listed: Apr, 07, 2026
Price: $898,000
Living Area: 2,172 Sq. Ft.
Chestertown, MD | Active
Listed: Apr, 07, 2026
Price: $898,000
Living Area: 2,172 Sq. Ft.
210 N Queen St
Chestertown, MD | Closed
Listed: Jun, 24, 2026
Price: $735,000
Living Area: 2,730 Sq. Ft.
Chestertown, MD | Closed
Listed: Jun, 24, 2026
Price: $735,000
Living Area: 2,730 Sq. Ft.
2201 Pondtown Rd
Chestertown, MD | Closed
Listed: Jul, 21, 2026
Price: $1,500
Living Area: 1,272 Sq. Ft.
Chestertown, MD | Closed
Listed: Jul, 21, 2026
Price: $1,500
Living Area: 1,272 Sq. Ft.
27942 Old Morgnec Rd
Chestertown, MD | Active
Listed: Sep, 03, 2026
Price: $89,000
Living Area: 0 Sq. Ft.
Chestertown, MD | Active
Listed: Sep, 03, 2026
Price: $89,000
Living Area: 0 Sq. Ft.
207 Lincoln Dr
Chestertown, MD | Closed
Listed: Jul, 31, 2026
Price: $135,000
Living Area: 1,152 Sq. Ft.
Chestertown, MD | Closed
Listed: Jul, 31, 2026
Price: $135,000
Living Area: 1,152 Sq. Ft.
222 Mount Vernon Ave
Chestertown, MD | Closed
Listed: Oct, 27, 2025
Price: $419,999
Living Area: 1,656 Sq. Ft.
Chestertown, MD | Closed
Listed: Oct, 27, 2025
Price: $419,999
Living Area: 1,656 Sq. Ft.
6746 Quaker Neck Rd
Chestertown, MD | Expired
Listed: May, 18, 2017
Price: $195,000
Living Area: 4,624 Sq. Ft.
Chestertown, MD | Expired
Listed: May, 18, 2017
Price: $195,000
Living Area: 4,624 Sq. Ft.
6746 Quaker Neck Rd
Chestertown, MD | Active
Listed: Jan, 01, 2026
Price: $339,000
Living Area: 3,371 Sq. Ft.
Chestertown, MD | Active
Listed: Jan, 01, 2026
Price: $339,000
Living Area: 3,371 Sq. Ft.
6746 Quaker Rd
Chestertown, MD | Active
Listed: Jan, 02, 2026
Price: $339,000
Living Area: 3,371 Sq. Ft.
Chestertown, MD | Active
Listed: Jan, 02, 2026
Price: $339,000
Living Area: 3,371 Sq. Ft.
6746 Quaker Neck Rd
Chestertown, MD | Expired
Listed: Nov, 22, 2016
Price: $195,000
Living Area: 3,371 Sq. Ft.
Chestertown, MD | Expired
Listed: Nov, 22, 2016
Price: $195,000
Living Area: 3,371 Sq. Ft.
105 N Water St #2
Chestertown, MD | Closed
Listed: Jun, 16, 2026
Price: $475,000
Living Area: 1,011 Sq. Ft.
Chestertown, MD | Closed
Listed: Jun, 16, 2026
Price: $475,000
Living Area: 1,011 Sq. Ft.
300 And 302 S Mill St
Chestertown, MD | Active
Listed: Jul, 23, 2026
Price: $1,195,000
Living Area: 806 Sq. Ft.
Chestertown, MD | Active
Listed: Jul, 23, 2026
Price: $1,195,000
Living Area: 806 Sq. Ft.
8312 Broad Neck Rd
Chestertown, MD | Closed
Listed: Jul, 22, 2026
Price: $380,000
Living Area: 3,292 Sq. Ft.
Chestertown, MD | Closed
Listed: Jul, 22, 2026
Price: $380,000
Living Area: 3,292 Sq. Ft.
122 Speer Rd #5
Chestertown, MD | Active
Listed: Aug, 06, 2026
Price: $5,017
Living Area: 12,290 Sq. Ft.
Chestertown, MD | Active
Listed: Aug, 06, 2026
Price: $5,017
Living Area: 12,290 Sq. Ft.
409 Calvert St
Chestertown, MD | Canceled
Listed: Jul, 07, 2026
Price: $145,000
Living Area: 1,192 Sq. Ft.
Chestertown, MD | Canceled
Listed: Jul, 07, 2026
Price: $145,000
Living Area: 1,192 Sq. Ft.
117 Water St 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.
117 Water St 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 St N #1a, 1b, 2a, & 2b
Chestertown, MD | Active
Listed: Mar, 01, 2026
Price: $1,500,000
Living Area: 5,400 Sq. Ft.
Chestertown, MD | Active
Listed: Mar, 01, 2026
Price: $1,500,000
Living Area: 5,400 Sq. Ft.
115 Chester Arms Dr
Chestertown, MD | Closed
Listed: Dec, 27, 2022
Price: $238,000
Living Area: 1,140 Sq. Ft.
Chestertown, MD | Closed
Listed: Dec, 27, 2022
Price: $238,000
Living Area: 1,140 Sq. Ft.
8732 Elm Rd
Chestertown, MD | Active
Listed: Sep, 14, 2026
Price: $289,000
Living Area: 1,056 Sq. Ft.
Chestertown, MD | Active
Listed: Sep, 14, 2026
Price: $289,000
Living Area: 1,056 Sq. Ft.
123 Heath Rd
Chestertown, MD | Closed
Listed: Jul, 17, 2026
Price: $349,000
Living Area: 1,792 Sq. Ft.
Chestertown, MD | Closed
Listed: Jul, 17, 2026
Price: $349,000
Living Area: 1,792 Sq. Ft.
105 High St
Chestertown, MD | Active
Listed: Nov, 04, 2024
Price: $1,245,500
Living Area: 3,243 Sq. Ft.
Chestertown, MD | Active
Listed: Nov, 04, 2024
Price: $1,245,500
Living Area: 3,243 Sq. Ft.
1010 Twin Ct
Chestertown, MD | Active
Listed: Jul, 29, 2026
Price: $349,900
Living Area: 1,476 Sq. Ft.
Chestertown, MD | Active
Listed: Jul, 29, 2026
Price: $349,900
Living Area: 1,476 Sq. Ft.
115 Chester Arms Dr
Chestertown, MD | Active
Listed: Aug, 14, 2026
Price: $259,000
Living Area: 1,140 Sq. Ft.
Chestertown, MD | Active
Listed: Aug, 14, 2026
Price: $259,000
Living Area: 1,140 Sq. Ft.
116 Harlan Loop
Chestertown, MD | Closed
Listed: Oct, 25, 2023
Price: $328,500
Living Area: 4,067 Sq. Ft.
Chestertown, MD | Closed
Listed: Oct, 25, 2023
Price: $328,500
Living Area: 4,067 Sq. Ft.
Caulks Field Road
Chestertown, MD | Expired
Listed: Feb, 20, 2023
Price: $75,000
Living Area: 0 Sq. Ft.
Chestertown, MD | Expired
Listed: Feb, 20, 2023
Price: $75,000
Living Area: 0 Sq. Ft.
Georgetown Rd SE
Chestertown, MD | Expired
Listed: Feb, 20, 2023
Price: $60,000
Living Area: 0 Sq. Ft.
Chestertown, MD | Expired
Listed: Feb, 20, 2023
Price: $60,000
Living Area: 0 Sq. Ft.
212 Washington Ave
Chestertown, MD | Active
Listed: Aug, 30, 2026
Price: $675,000
Living Area: 2,838 Sq. Ft.
Chestertown, MD | Active
Listed: Aug, 30, 2026
Price: $675,000
Living Area: 2,838 Sq. Ft.
100 Little Harbor Way
Chestertown, MD | Closed
Listed: Apr, 01, 2025
Price: $699,000
Living Area: 2,204 Sq. Ft.
Chestertown, MD | Closed
Listed: Apr, 01, 2025
Price: $699,000
Living Area: 2,204 Sq. Ft.
7982 Radcliffe Rd
Chestertown, MD | Active Under Contract
Listed: Aug, 13, 2026
Price: $399,000
Living Area: 1,904 Sq. Ft.
Chestertown, MD | Active Under Contract
Listed: Aug, 13, 2026
Price: $399,000
Living Area: 1,904 Sq. Ft.
124 Wilton Rd
Chestertown, MD | Active
Listed: Aug, 11, 2026
Price: $294,900
Living Area: 1,056 Sq. Ft.
Chestertown, MD | Active
Listed: Aug, 11, 2026
Price: $294,900
Living Area: 1,056 Sq. Ft.
522 High 522 & 524 St
Chestertown, MD | Closed
Listed: Mar, 04, 2003
Price: $103,800
Living Area: 0 Sq. Ft.
Chestertown, MD | Closed
Listed: Mar, 04, 2003
Price: $103,800
Living Area: 0 Sq. Ft.
304 Hadaway Dr
Chestertown, MD | Canceled
Listed: Feb, 12, 2026
Price: $339,000
Living Area: 1,325 Sq. Ft.
Chestertown, MD | Canceled
Listed: Feb, 12, 2026
Price: $339,000
Living Area: 1,325 Sq. Ft.
103 Landing Ln
Chestertown, MD | Withdrawn
Listed: Sep, 02, 2025
Price: $499,999
Living Area: 2,100 Sq. Ft.
Chestertown, MD | Withdrawn
Listed: Sep, 02, 2025
Price: $499,999
Living Area: 2,100 Sq. Ft.
103 Landing Ln
Chestertown, MD | Expired
Listed: Jul, 12, 2024
Price: $579,000
Living Area: 2,100 Sq. Ft.
Chestertown, MD | Expired
Listed: Jul, 12, 2024
Price: $579,000
Living Area: 2,100 Sq. Ft.
103 Landing Ln
Chestertown, MD | Canceled
Listed: Mar, 26, 2025
Price: $569,000
Living Area: 2,100 Sq. Ft.
Chestertown, MD | Canceled
Listed: Mar, 26, 2025
Price: $569,000
Living Area: 2,100 Sq. Ft.
Parcel Buck Neck Ldg Rd
Chestertown, MD | Active
Listed: Apr, 19, 2024
Price: $5,000
Living Area: 0 Sq. Ft.
Chestertown, MD | Active
Listed: Apr, 19, 2024
Price: $5,000
Living Area: 0 Sq. Ft.
103 Metcalf Rd
Chestertown, MD | Active
Listed: Sep, 09, 2026
Price: $259,900
Living Area: 1,280 Sq. Ft.
Chestertown, MD | Active
Listed: Sep, 09, 2026
Price: $259,900
Living Area: 1,280 Sq. Ft.
8276 Broad Neck Rd
Chestertown, MD | Expired
Listed: Mar, 14, 2026
Price: $1,395,000
Living Area: 3,383 Sq. Ft.
Chestertown, MD | Expired
Listed: Mar, 14, 2026
Price: $1,395,000
Living Area: 3,383 Sq. Ft.
206 N Mill St
Chestertown, MD | Withdrawn
Listed: Sep, 05, 2026
Price: $430,000
Living Area: 1,520 Sq. Ft.
Chestertown, MD | Withdrawn
Listed: Sep, 05, 2026
Price: $430,000
Living Area: 1,520 Sq. Ft.
206 N Mill St
Chestertown, MD | Closed
Listed: Oct, 05, 2026
Price: $1,950
Living Area: 1,520 Sq. Ft.
Chestertown, MD | Closed
Listed: Oct, 05, 2026
Price: $1,950
Living Area: 1,520 Sq. Ft.
8986 Orchard Dr
Chestertown, MD | Coming Soon
Listed: Sep, 20, 2026
Price: $679,900
Living Area: 3,228 Sq. Ft.
Chestertown, MD | Coming Soon
Listed: Sep, 20, 2026
Price: $679,900
Living Area: 3,228 Sq. Ft.
6324 Quaker Neck Rd
Chestertown, MD | Active
Listed: Sep, 16, 2026
Price: $2,895,000
Living Area: 5,938 Sq. Ft.
Chestertown, MD | Active
Listed: Sep, 16, 2026
Price: $2,895,000
Living Area: 5,938 Sq. Ft.
105 N Water St #3
Chestertown, MD | Active
Listed: Sep, 19, 2026
Price: $459,000
Living Area: 1,098 Sq. Ft.
Chestertown, MD | Active
Listed: Sep, 19, 2026
Price: $459,000
Living Area: 1,098 Sq. Ft.
9126 Fairlee Rd
Chestertown, MD | Active
Listed: Jun, 30, 2026
Price: $313,500
Living Area: 1,216 Sq. Ft.
Chestertown, MD | Active
Listed: Jun, 30, 2026
Price: $313,500
Living Area: 1,216 Sq. Ft.
228 S Water St
Chestertown, MD | Expired
Listed: Oct, 13, 2025
Price: $878,000
Living Area: 2,310 Sq. Ft.
Chestertown, MD | Expired
Listed: Oct, 13, 2025
Price: $878,000
Living Area: 2,310 Sq. Ft.
8630 Elm Rd
Chestertown, MD | Active
Listed: Aug, 08, 2026
Price: $424,900
Living Area: 1,936 Sq. Ft.
Chestertown, MD | Active
Listed: Aug, 08, 2026
Price: $424,900
Living Area: 1,936 Sq. Ft.
331 Devon Dr
Chestertown, MD | Withdrawn
Listed: Sep, 26, 2026
Price: $499,999
Living Area: 3,506 Sq. Ft.
Chestertown, MD | Withdrawn
Listed: Sep, 26, 2026
Price: $499,999
Living Area: 3,506 Sq. Ft.
7680 Country Club Ln
Chestertown, MD | Active
Listed: Jun, 30, 2026
Price: $825,000
Living Area: 2,639 Sq. Ft.
Chestertown, MD | Active
Listed: Jun, 30, 2026
Price: $825,000
Living Area: 2,639 Sq. Ft.
109 Parma Rd
Chestertown, MD | Pending
Listed: Jul, 31, 2026
Price: $315,000
Living Area: 1,288 Sq. Ft.
Chestertown, MD | Pending
Listed: Jul, 31, 2026
Price: $315,000
Living Area: 1,288 Sq. Ft.
1010 Twin Ct
Chestertown, MD | Expired
Listed: Mar, 02, 2018
Price: $249,900
Living Area: 1,500 Sq. Ft.
Chestertown, MD | Expired
Listed: Mar, 02, 2018
Price: $249,900
Living Area: 1,500 Sq. Ft.
