Listings in 21620 - Kent County, Maryland
Displaying 201 – 400 of 285 Real estate listings
#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.
517 Round Top Rd
Chestertown, MD | Active
Listed: Jun, 19, 2026
Price: $299,900
Living Area: 1,248 Sq. Ft.
Chestertown, MD | Active
Listed: Jun, 19, 2026
Price: $299,900
Living Area: 1,248 Sq. Ft.
210 N Queen St
Chestertown, MD | Active Under Contract
Listed: Jun, 24, 2026
Price: $735,000
Living Area: 2,730 Sq. Ft.
Chestertown, MD | Active Under Contract
Listed: Jun, 24, 2026
Price: $735,000
Living Area: 2,730 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.
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.
105 HICKORY LANE
CHESTERTOWN, MD | Closed
Listed: Jul, 10, 2023
Price: $95,000
Living Area: 0 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Jul, 10, 2023
Price: $95,000
Living Area: 0 Sq. Ft.
8629 AIRY HILL ROAD
CHESTERTOWN, MD | Closed
Listed: May, 09, 2026
Price: $425,000
Living Area: 1,440 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: May, 09, 2026
Price: $425,000
Living Area: 1,440 Sq. Ft.
8355 BROAD NECK ROAD
CHESTERTOWN, MD | Closed
Listed: Mar, 17, 2026
Price: $2,800
Living Area: 2,910 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Mar, 17, 2026
Price: $2,800
Living Area: 2,910 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.
601 WASHINGTON AVE,CHESTERTOWN,MD,21620,KENT
CHESTERTOWN, MD | Active
Listed: Nov, 21, 2024
Price: $2,864
Living Area: 13,500 Sq. Ft.
CHESTERTOWN, MD | Active
Listed: Nov, 21, 2024
Price: $2,864
Living Area: 13,500 Sq. Ft.
301 HICKORY LN,CHESTERTOWN,MD,21620,QUEEN ANNES
CHESTERTOWN, MD | Closed
Listed: Sep, 10, 2020
Price: $650,000
Living Area: 3,136 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Sep, 10, 2020
Price: $650,000
Living Area: 3,136 Sq. Ft.
301 HICKORY LN,CHESTERTOWN,MD,21620,QUEEN ANNES
CHESTERTOWN, MD | Closed
Listed: Sep, 10, 2020
Price: $650,000
Living Area: 3,136 Sq. Ft.
CHESTERTOWN, MD | Closed
Listed: Sep, 10, 2020
Price: $650,000
Living Area: 3,136 Sq. Ft.
6746 Quaker Neck Rd, Chestertown, MD 21620-4917, United States
CHESTERTOWN, MD | Active Under Contract
Listed: Jan, 01, 2026
Price: $384,000
Living Area: 3,371 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Jan, 01, 2026
Price: $384,000
Living Area: 3,371 Sq. Ft.
6746 Quaker Neck Rd, Chestertown, MD 21620-4917, United States
CHESTERTOWN, MD | Active Under Contract
Listed: Jan, 02, 2026
Price: $384,000
Living Area: 3,371 Sq. Ft.
CHESTERTOWN, MD | Active Under Contract
Listed: Jan, 02, 2026
Price: $384,000
Living Area: 3,371 Sq. Ft.
2201 Pondtown Rd
Chestertown, MD | Hold
Listed: Jul, 21, 2026
Price: $1,500
Living Area: 1,272 Sq. Ft.
Chestertown, MD | Hold
Listed: Jul, 21, 2026
Price: $1,500
Living Area: 1,272 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.
1904 Pondtown Rd
Chestertown, MD | Pending
Listed: May, 30, 2026
Price: $265,000
Living Area: 1,967 Sq. Ft.
Chestertown, MD | Pending
Listed: May, 30, 2026
Price: $265,000
Living Area: 1,967 Sq. Ft.
8890 Fairlee Rd
Chestertown, MD | Active
Listed: Jun, 25, 2026
Price: $2,300
Living Area: 1,232 Sq. Ft.
Chestertown, MD | Active
Listed: Jun, 25, 2026
Price: $2,300
Living Area: 1,232 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.
136 Hilltop Dr
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.
21146 Montana Ave
Chestertown, MD | Active
Listed: Jul, 28, 2026
Price: $289,900
Living Area: 1,500 Sq. Ft.
Chestertown, MD | Active
Listed: Jul, 28, 2026
Price: $289,900
Living Area: 1,500 Sq. Ft.
Parcel Buck Neck Ldg Rd
Chestertown, MD | Active
Listed: Apr, 19, 2024
Price: $8,000
Living Area: 0 Sq. Ft.
Chestertown, MD | Active
Listed: Apr, 19, 2024
Price: $8,000
Living Area: 0 Sq. Ft.
8999 Orchard Dr
Chestertown, MD | Active
Listed: Jul, 20, 2026
Price: $824,900
Living Area: 4,353 Sq. Ft.
Chestertown, MD | Active
Listed: Jul, 20, 2026
Price: $824,900
Living Area: 4,353 Sq. Ft.
9126 Fairlee Rd
Chestertown, MD | Active
Listed: Jun, 30, 2026
Price: $344,000
Living Area: 1,216 Sq. Ft.
Chestertown, MD | Active
Listed: Jun, 30, 2026
Price: $344,000
Living Area: 1,216 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.
105 N Water St #2
Chestertown, MD | Active Under Contract
Listed: Jun, 16, 2026
Price: $475,000
Living Area: 1,011 Sq. Ft.
Chestertown, MD | Active Under Contract
Listed: Jun, 16, 2026
Price: $475,000
Living Area: 1,011 Sq. Ft.
104 Maple Ave #6
Chestertown, MD | Active
Listed: Apr, 17, 2026
Price: $1,920
Living Area: 900 Sq. Ft.
Chestertown, MD | Active
Listed: Apr, 17, 2026
Price: $1,920
Living Area: 900 Sq. Ft.
103 S Lynchburg St
Chestertown, MD | Closed
Listed: Jun, 18, 2026
Price: $1,400
Living Area: 1,040 Sq. Ft.
Chestertown, MD | Closed
Listed: Jun, 18, 2026
Price: $1,400
Living Area: 1,040 Sq. Ft.
409 Calvert St
Chestertown, MD | Active
Listed: Jul, 07, 2026
Price: $155,000
Living Area: 1,192 Sq. Ft.
Chestertown, MD | Active
Listed: Jul, 07, 2026
Price: $155,000
Living Area: 1,192 Sq. Ft.
10572 Watonga Rd
Chestertown, MD | Closed
Listed: May, 03, 2026
Price: $325,000
Living Area: 1,404 Sq. Ft.
Chestertown, MD | Closed
Listed: May, 03, 2026
Price: $325,000
Living Area: 1,404 Sq. Ft.
104 Cedar St
Chestertown, MD | Closed
Listed: May, 12, 2026
Price: $2,600
Living Area: 2,612 Sq. Ft.
Chestertown, MD | Closed
Listed: May, 12, 2026
Price: $2,600
Living Area: 2,612 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.
206 Burchard Sawmill Rd
Chestertown, MD | Closed
Listed: Mar, 17, 2026
Price: $29,000
Living Area: 0 Sq. Ft.
Chestertown, MD | Closed
Listed: Mar, 17, 2026
Price: $29,000
Living Area: 0 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.
228 Merganser Dr
Chestertown, MD | Pending
Listed: May, 13, 2026
Price: $59,999
Living Area: 0 Sq. Ft.
Chestertown, MD | Pending
Listed: May, 13, 2026
Price: $59,999
Living Area: 0 Sq. Ft.
104 Flying Cloud Dr
Chestertown, MD | Hold
Listed: Mar, 01, 2026
Price: $394,900
Living Area: 2,535 Sq. Ft.
Chestertown, MD | Hold
Listed: Mar, 01, 2026
Price: $394,900
Living Area: 2,535 Sq. Ft.
123 Heath Rd
Chestertown, MD | Active
Listed: Jul, 17, 2026
Price: $349,000
Living Area: 1,792 Sq. Ft.
Chestertown, MD | Active
Listed: Jul, 17, 2026
Price: $349,000
Living Area: 1,792 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.
154 Longfellow Dr
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.
349 & 351 High St
Chestertown, MD | Closed
Listed: Mar, 12, 2024
Price: $395,000
Living Area: 3,664 Sq. Ft.
Chestertown, MD | Closed
Listed: Mar, 12, 2024
Price: $395,000
Living Area: 3,664 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.
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.
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 S Water St
Chestertown, MD | Closed
Listed: Jan, 12, 2026
Price: $549,000
Living Area: 2,008 Sq. Ft.
Chestertown, MD | Closed
Listed: Jan, 12, 2026
Price: $549,000
Living Area: 2,008 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 #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 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.
127 Wood Duck Ln
Chestertown, MD | Closed
Listed: May, 18, 2026
Price: $138,000
Living Area: 1,666 Sq. Ft.
Chestertown, MD | Closed
Listed: May, 18, 2026
Price: $138,000
Living Area: 1,666 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.
107 Conley Dr
Chestertown, MD | Active
Listed: Jul, 14, 2026
Price: $240,000
Living Area: 1,140 Sq. Ft.
Chestertown, MD | Active
Listed: Jul, 14, 2026
Price: $240,000
Living Area: 1,140 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.
Lots 253-254 Carimon Rd
Chestertown, MD | Closed
Listed: Sep, 13, 2023
Price: $9,500
Living Area: 0 Sq. Ft.
Chestertown, MD | Closed
Listed: Sep, 13, 2023
Price: $9,500
Living Area: 0 Sq. Ft.
118 Little Harbor Way #202
Chestertown, MD | Closed
Listed: Oct, 07, 2025
Price: $675,000
Living Area: 1,600 Sq. Ft.
Chestertown, MD | Closed
Listed: Oct, 07, 2025
Price: $675,000
Living Area: 1,600 Sq. Ft.
301 Lincoln Dr
Chestertown, MD | Closed
Listed: Mar, 02, 2026
Price: $299,900
Living Area: 1,152 Sq. Ft.
Chestertown, MD | Closed
Listed: Mar, 02, 2026
Price: $299,900
Living Area: 1,152 Sq. Ft.
22360 Great Oak Landing Rd
Chestertown, MD | Closed
Listed: Apr, 29, 2026
Price: $525,000
Living Area: 2,688 Sq. Ft.
Chestertown, MD | Closed
Listed: Apr, 29, 2026
Price: $525,000
Living Area: 2,688 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.
1010 Twin Ct
Chestertown, MD | Active
Listed: Jul, 29, 2026
Price: $375,000
Living Area: 1,476 Sq. Ft.
Chestertown, MD | Active
Listed: Jul, 29, 2026
Price: $375,000
Living Area: 1,476 Sq. Ft.
8312 Broad Neck Rd
Chestertown, MD | Active
Listed: Jul, 22, 2026
Price: $380,000
Living Area: 3,292 Sq. Ft.
Chestertown, MD | Active
Listed: Jul, 22, 2026
Price: $380,000
Living Area: 3,292 Sq. Ft.
204 Double Creek Rd
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.
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.
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.
25440 Learman Rd
Chestertown, MD | Active Under Contract
Listed: Apr, 29, 2026
Price: $3,000,000
Living Area: 3,142 Sq. Ft.
Chestertown, MD | Active Under Contract
Listed: Apr, 29, 2026
Price: $3,000,000
Living Area: 3,142 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.
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.
