CHESTERTOWN

MLS ID: MDKE2006224 Listing Key: 804638807262 Property Type:Residential

2 BED 3 BATH 1,867 ft² Property 3,672 ft² Lot

Open House: Apr 25, 2026 at 11:00 AM to 01:00 PM

108 Oak Leaf Dr, Chestertown MD 21620

Offered for $299,500.00

Active
Listed: 2026-04-16

Residential for sale

CHESTERTOWN

MLS ID: MDKE2006328 Listing Key: 804709064330 Property Type:Residential

3 BED 2 BATH 16,200 ft² Lot

10584 Klamath Rd, Chestertown MD 21620

Offered for $319,900.00

Active
Listed: 2026-04-16

Residential for sale

CHESTERTOWN

MLS ID: MDQA2016782 Listing Key: 804732154560 Property Type:Residential

3 BED 2 BATH 1,432 ft² Property 43,996 ft² Lot

136 Hilltop Dr, Chestertown MD 21620

Offered for $366,000.00

Active
Listed: 2026-04-16

Residential for sale

CHESTERTOWN

MLS ID: MDKE2006390 Listing Key: 804780746552 Property Type:Residential

3 BED 2 BATH 1,232 ft² Property 14,375 ft² Lot

8706 Elm Rd, Chestertown MD 21620

Offered for $320,000.00

Active
Listed: 2026-04-16

Residential for sale

CHESTERTOWN

MLS ID: MDQA2016836 Listing Key: 804746061118 Property Type:Residential

3 BED 1 BATH 1,120 ft² Property 24,000 ft² Lot

Open House: Apr 19, 2026 at 01:00 PM to 03:00 PM

208 Central Dr, Chestertown MD 21620

Offered for $315,000.00

Active
Listed: 2026-04-15

Residential for sale

CHESTERTOWN

MLS ID: MDKE2006378 Listing Key: 804769168178 Property Type:Residential

3 BED 2 BATH 1,499 ft² Property 15,376 ft² Lot

Open House: Apr 19, 2026 at 12:00 PM to 02:00 PM

10594 Millbrook Dr, Chestertown MD 21620

Offered for $329,000.00

Active
Listed: 2026-04-15

Residential for sale

CHESTERTOWN

MLS ID: MDKE2006220 Listing Key: 804638526874 Property Type:Residential

3 BED 1 BATH 1,140 ft² Property 4,300 ft² Lot

107 Conley Dr, Chestertown MD 21620

Offered for $170,000.00

Active
Listed: 2026-03-16

Residential for sale

CHESTERTOWN

MLS ID: MDKE2006324 Listing Key: 804707660750 Property Type:Residential

3 BED 2 BATH 1,566 ft² Property 52,272 ft² Lot

10087 John Carvill Rd, Chestertown MD 21620

Offered for $695,000.00

Active
Listed: 2026-04-10

Residential for sale

CHESTERTOWN

MLS ID: MDQA2016478 Listing Key: 804633592740 Property Type:Residential

3 BED 1 BATH 1,296 ft² Property 90,605 ft² Lot

113 Pear Tree Point Rd, Chestertown MD 21620

Offered for $250,000.00

Active
Listed: 2026-03-13

Residential for sale

CHESTERTOWN

MLS ID: MDQA2016688 Listing Key: 804695051792 Property Type:Residential

3 BED 2 BATH 1,120 ft² Property 47,916 ft² Lot

2032 Pondtown Rd, Chestertown MD 21620

Offered for $325,000.00

Active
Listed: 2026-04-09

Residential for sale

CHESTERTOWN

MLS ID: MDKE2006364 Listing Key: 804751460126 Property Type:Residential

2 BED 1 BATH 912 ft² Property 16,000 ft² Lot

21217 Texas Ave, Chestertown MD 21620

Offered for $265,000.00

Active
Listed: 2026-04-09

Residential for sale

CHESTERTOWN

MLS ID: MDKE2006354 Listing Key: 804737005806 Property Type:Residential

3 BED 4 BATH 2,172 ft² Property 3,782 ft² Lot

226 S Water St, Chestertown MD 21620

Offered for $898,000.00

Active
Listed: 2026-04-08

Residential for sale

CHESTERTOWN

MLS ID: MDQA2016758 Listing Key: 804718709072 Property Type:Residential

3 BED 2 BATH 1,271 ft² Property 21,760 ft² Lot

720 Deep Landing Rd, Chestertown MD 21620

Offered for $369,999.00

Active
Listed: 2026-04-06

Residential for sale

CHESTERTOWN

MLS ID: MDKE2006116 Listing Key: 804529214196 Property Type:Residential

4 BED 2 BATH 1,325 ft² Property 18,000 ft² Lot

304 Hadaway Dr, Chestertown MD 21620

Offered for $339,000.00

Active
Listed: 2026-02-12

Residential for sale

CHESTERTOWN

MLS ID: MDKE2006344 Listing Key: 804723221484 Property Type:Residential

5 BED 4 BATH 3,816 ft² Property 10,000 ft² Lot

103 Sutton Way, Chestertown MD 21620

Offered for $550,000.00

Active
Listed: 2026-04-03

Residential for sale

CHESTERTOWN

MLS ID: MDKE2006152 Listing Key: 804579017874 Property Type:Residential

3 BED 4 BATH 2,472 ft² Property 6,000 ft² Lot

106 Queen St S, Chestertown MD 21620

Offered for $865,000.00

Active
Listed: 2026-04-02

Residential for sale

CHESTERTOWN

MLS ID: MDKE2006212 Listing Key: 804632173286 Property Type:Residential

5 BED 4 BATH 2,535 ft² Property 4,000 ft² Lot

104 Flying Cloud Dr, Chestertown MD 21620

Offered for $399,900.00

Active
Listed: 2026-04-02

Residential for sale

CHESTERTOWN

MLS ID: MDQA2016632 Listing Key: 804682028656 Property Type:Residential

3 BED 3 BATH 2,060 ft² Property 43,560 ft² Lot

704 Truslow Rd, Chestertown MD 21620

Offered for $440,000.00

Active
Listed: 2026-04-02

Residential for sale

CHESTERTOWN

MLS ID: MDKE2006316 Listing Key: 804703197360 Property Type:Residential

3 BED 2 BATH 1,588 ft² Property 17,944 ft² Lot

201 Birch Run Rd, Chestertown MD 21620

Offered for $435,000.00

Active
Listed: 2026-03-30

Residential for sale

CHESTERTOWN

MLS ID: MDKE2006250 Listing Key: 804654996174 Property Type:Residential

3 BED 1 BATH 1,200 ft² Property 6,350 ft² Lot

139 Prospect St, Chestertown MD 21620

Offered for $225,000.00

Active
Listed: 2026-03-27

Residential for sale

CHESTERTOWN

MLS ID: MDQA2016624 Listing Key: 804680120572 Property Type:Residential

3 BED 3 BATH 2,268 ft² Property 47,916 ft² Lot

101 Coleman Dr, Chestertown MD 21620

Offered for $524,900.00

Active
Listed: 2026-03-27

Residential for sale

CHESTERTOWN

MLS ID: MDKE2006260 Listing Key: 804671996958 Property Type:Residential

3 BED 2 BATH 2,055 ft² Property 15,000 ft² Lot

202 Waldo Dr, Chestertown MD 21620

Offered for $389,000.00

Active
Listed: 2026-03-25

Residential for sale

CHESTERTOWN

MLS ID: MDKE2005434 Listing Key: 804002315376 Property Type:Residential

2 BED 1 BATH 1,296 ft² Property 3,840 ft² Lot

234 N College Ave, Chestertown MD 21620

Offered for $130,000.00

Active
Listed: 2025-08-04

Residential for sale

CHESTERTOWN

MLS ID: MDKE2006040 Listing Key: 804411707326 Property Type:Residential

3 BED 3 BATH 1,216 ft² Property 3,108 ft² Lot

109 S College Ave, Chestertown MD 21620

Offered for $419,900.00

Active
Listed: 2026-03-20

Residential for sale

CHESTERTOWN

MLS ID: MDKE2006216 Listing Key: 804637287412 Property Type:Residential

4 BED 4 BATH 3,383 ft² Property 862,924 ft² Lot

8276 Broad Neck Rd, Chestertown MD 21620

Offered for $1,495,000.00

Active
Listed: 2026-03-19

Residential for sale

CHESTERTOWN

MLS ID: MDKE2006198 Listing Key: 804618520078 Property Type:Residential

2 BED 1 BATH 1,294 ft² Property 8,000 ft² Lot

21125 Iowa Ave, Chestertown MD 21620

Offered for $339,900.00

Active
Listed: 2026-03-19

Residential for sale

CHESTERTOWN

MLS ID: MDKE2006170 Listing Key: 804584533268 Property Type:Residential

3 BED 2 BATH 1,152 ft² Property 17,860 ft² Lot

301 Lincoln Dr, Chestertown MD 21620

Offered for $309,900.00

Active
Listed: 2026-03-14

Residential for sale

CHESTERTOWN

MLS ID: MDQA2016312 Listing Key: 804584243278 Property Type:Residential

3 BED 2 BATH 1,392 ft² Property 33,300 ft² Lot

109 Wilton Rd, Chestertown MD 21620

Offered for $344,900.00

Active
Listed: 2026-03-09

Residential for sale

CHESTERTOWN

MLS ID: MDKE2006186 Listing Key: 804596698552 Property Type:Residential

3 BED 2 BATH 1,200 ft² Property 2,240 ft² Lot

Open House: Apr 18, 2026 at 11:00 AM to 01:00 PM

107 Metcalf Rd, Chestertown MD 21620

Offered for $259,900.00

Active
Listed: 2026-03-07

Residential for sale

CHESTERTOWN

MLS ID: MDKE2005900 Listing Key: 804301916604 Property Type:Residential

5 BED 3 BATH 2,956 ft² Property 34,507 ft² Lot

231 Richard Dr, Chestertown MD 21620

Offered for $1,150,000.00

Active
Listed: 2026-03-06

Residential for sale

CHESTERTOWN

MLS ID: MDKE2005670 Listing Key: 804152904726 Property Type:Residential

2 BED 3 BATH 2,100 ft² Property 1,306.800 ft² Lot

103 Landing Ln, Chestertown MD 21620

Offered for $519,999.00

Active
Listed: 2025-09-10

Residential for sale

CHESTERTOWN

MLS ID: MDKE2006178 Listing Key: 804592395900 Property Type:Residential

2 BED 1 BATH 1,232 ft² Property 2,160 ft² Lot

21324 Persimmon Dr, Chestertown MD 21620

Offered for $136,800.00

Active
Listed: 2026-03-03

Residential for sale

CHESTERTOWN

MLS ID: MDKE2006158 Listing Key: 804583499632 Property Type:Residential

7 BED 5 BATH 5,400 ft² Property

117 Water St N #1A, 1B, 2A, & 2B, Chestertown MD 21620

Offered for $1,600,000.00

Active
Listed: 2026-03-01

Residential for sale

CHESTERTOWN

MLS ID: MDKE2006162 Listing Key: 804583659072 Property Type:Residential

3 BED 3 BATH 3,000 ft² Property

117 Water St N #1A, Chestertown MD 21620

Offered for $685,000.00

Active
Listed: 2026-03-01

Residential for sale

CHESTERTOWN

MLS ID: MDKE2006164 Listing Key: 804583689504 Property Type:Residential

1 BED 1 BATH 700 ft² Property

117 Water St N #1B, Chestertown MD 21620

Offered for $200,000.00

Active
Listed: 2026-03-01

Residential for sale

CHESTERTOWN

MLS ID: MDKE2006166 Listing Key: 804583748840 Property Type:Residential

2 BED 1 BATH 787 ft² Property

117 Water St N #2A, Chestertown MD 21620

Offered for $375,000.00

Active
Listed: 2026-03-01

Residential for sale

CHESTERTOWN

MLS ID: MDKE2006168 Listing Key: 804583770586 Property Type:Residential

1 BED 1 BATH 850 ft² Property

117 Water St N #2B, Chestertown MD 21620

Offered for $350,000.00

Active
Listed: 2026-03-01

Residential for sale

CHESTERTOWN

MLS ID: MDKE2006142 Listing Key: 804566302920 Property Type:Residential

2 BATH 2,045 ft² Property 4,342 ft² Lot

201 N Lynchburg St, Chestertown MD 21620

Offered for $795,000.00

Active
Listed: 2026-02-24

Residential for sale

CHESTERTOWN

MLS ID: MDKE2005800 Listing Key: 804225720530 Property Type:Residential

3 BED 2 BATH 1,600 ft² Property

118 Little Harbor Way #202, Chestertown MD 21620

Offered for $675,000.00

Active
Listed: 2026-02-12

Residential for sale

CHESTERTOWN

MLS ID: MDQA2015996 Listing Key: 804474647418 Property Type:Residential

3 BED 3 BATH 2,927 ft² Property 38,071 ft² Lot

204 Double Creek Rd, Chestertown MD 21620

Offered for $612,000.00

Active
Listed: 2026-02-12

Residential for sale

CHESTERTOWN

MLS ID: MDKE2006110 Listing Key: 804526272084 Property Type:Residential

2 BED 1 BATH 910 ft² Property 2,400 ft² Lot

132 Prospect St, Chestertown MD 21620

Offered for $157,400.00

Active
Listed: 2026-02-12

Residential for sale

CHESTERTOWN

MLS ID: MDKE2006014 Listing Key: 804401857440 Property Type:Residential

5 BED 3 BATH 3,371 ft² Property 29,577 ft² Lot

6746 Quaker Neck Rd, Chestertown MD 21620

Offered for $384,000.00

Active
Listed: 2026-01-02

Residential for sale

CHESTERTOWN

MLS ID: MDKE2005964 Listing Key: 804346831044 Property Type:Residential

4 BED 3 BATH 2,880 ft² Property 12,197 ft² Lot

110 Trafford Dr, Chestertown MD 21620

Offered for $465,000.00

Active
Listed: 2026-01-01

Residential for sale

CHESTERTOWN

MLS ID: MDKE2005982 Listing Key: 804364996454 Property Type:Residential

5 BED 4 BATH 3,932 ft² Property 10,401 ft² Lot

218 Camelot Dr, Chestertown MD 21620

Offered for $510,000.00

Active
Listed: 2025-12-20

Residential for sale

CHESTERTOWN

MLS ID: MDKE2005968 Listing Key: 804350816624 Property Type:Residential

3 BED 2 BATH 1,280 ft² Property 3,920 ft² Lot

109 Metcalf Rd, Chestertown MD 21620

Offered for $264,900.00

Active
Listed: 2025-12-09

Residential for sale

CHESTERTOWN

MLS ID: MDKE2005950 Listing Key: 804342363882 Property Type:Residential

3 BED 3 BATH 1,964 ft² Property

102 Little Harbor Way, Chestertown MD 21620

Offered for $839,500.00

Active
Listed: 2025-12-04

Residential for sale

CHESTERTOWN

MLS ID: MDKE2005952 Listing Key: 804342507000 Property Type:Residential

3 BED 4 BATH 2,192 ft² Property

104 Landing Ln, Chestertown MD 21620

Offered for $813,900.00

Active
Listed: 2025-12-04

Residential for sale

CHESTERTOWN

MLS ID: MDKE2005954 Listing Key: 804342654430 Property Type:Residential

4 BED 4 BATH 2,784 ft² Property

#25 Landing Ln, Chestertown MD 21620

Offered for $1,099,900.00

Active
Listed: 2025-12-04

Residential for sale

CHESTERTOWN

MLS ID: MDKE2005956 Listing Key: 804343309714 Property Type:Residential

3 BED 3 BATH 1,964 ft² Property

#35 Landing Ln, Chestertown MD 21620

Offered for $786,900.00

Active
Listed: 2025-12-04

Residential for sale

CHESTERTOWN

MLS ID: MDKE2005958 Listing Key: 804343455500 Property Type:Residential

3 BED 3 BATH 1,964 ft² Property

#36 Landing Ln, Chestertown MD 21620

Offered for $753,500.00

Active
Listed: 2025-12-04

Residential for sale

CHESTERTOWN

MLS ID: MDKE2005960 Listing Key: 804343626008 Property Type:Residential

3 BED 3 BATH 1,964 ft² Property

#37 Landing Ln, Chestertown MD 21620

Offered for $765,900.00

Active
Listed: 2025-12-04

Residential for sale

CHESTERTOWN

MLS ID: MDKE2005930 Listing Key: 804322342634 Property Type:Residential

5 BED 4 BATH 3,504 ft² Property 12,284 ft² Lot

311 Devon Dr, Chestertown MD 21620

Offered for $525,000.00

Active
Listed: 2025-11-21

Residential for sale

CHESTERTOWN

MLS ID: MDKE2005906 Listing Key: 804303082430 Property Type:Residential

2 BED 2 BATH 920 ft² Property 5,865 ft² Lot

611 Cannon St, Chestertown MD 21620

Offered for $275,000.00

Active
Listed: 2025-11-11

Residential for sale

CHESTERTOWN

MLS ID: MDKE2005768 Listing Key: 804207016806 Property Type:Residential

3 BED 3 BATH 2,231 ft² Property

Little Harbor Way #1, Chestertown MD 21620

Offered for $1,459,000.00

Active
Listed: 2025-11-10

Residential for sale

CHESTERTOWN

MLS ID: MDKE2005892 Listing Key: 804299122792 Property Type:Residential

3 BED 4 BATH 2,092 ft² Property

106 Landing Ln, Chestertown MD 21620

Offered for $799,900.00

Active
Listed: 2025-11-10

Residential for sale

CHESTERTOWN

MLS ID: MDKE2005894 Listing Key: 804299331640 Property Type:Residential

3 BED 3 BATH 1,980 ft² Property

104 Little Harbor Way, Chestertown MD 21620

Offered for $849,900.00

Active
Listed: 2025-11-10

Residential for sale

CHESTERTOWN

MLS ID: MDKE2005890 Listing Key: 804298812462 Property Type:Residential

5 BED 5 BATH 3,243 ft² Property 2,688 ft² Lot

105 High St, Chestertown MD 21620

Offered for $1,395,500.00

Active
Listed: 2025-11-07

Residential for sale

CHESTERTOWN

MLS ID: MDKE2005876 Listing Key: 804286624042 Property Type:Residential

4 BED 2 BATH 1,656 ft² Property 6,450 ft² Lot

222 Mount Vernon Ave, Chestertown MD 21620

Offered for $439,999.00

Active
Listed: 2025-11-06

Residential for sale

CHESTERTOWN

MLS ID: MDKE2005850 Listing Key: 804264421750 Property Type:Residential

4 BED 2,524 ft² Property 59,677 ft² Lot

8620 Park Dr, Chestertown MD 21620

Offered for $499,900.00

Active
Listed: 2025-10-25

Residential for sale

CHESTERTOWN

MLS ID: MDQA2014830 Listing Key: 804155837992 Property Type:Residential

3 BED 2 BATH 1,096 ft² Property 29,352 ft² Lot

222 Dutchess Rd, Chestertown MD 21620

Offered for $320,000.00

Active
Listed: 2025-10-18

Residential for sale

CHESTERTOWN

MLS ID: MDQA2015154 Listing Key: 804232121412 Property Type:Residential

3 BED 2 BATH 1,666 ft² Property 22,988 ft² Lot

127 Wood Duck Ln, Chestertown MD 21620

Offered for $185,000.00

Active
Listed: 2025-10-11

Residential for sale

CHESTERTOWN

MLS ID: MDKE2005590 Listing Key: 804095805872 Property Type:Residential

5 BED 5 BATH 4,305 ft² Property 36,677 ft² Lot

Open House: May 09, 2026 at 11:00 AM to 01:00 PM

7989 Quaker Neck Rd, Chestertown MD 21620

Offered for $2,400,000.00

Active
Listed: 2025-09-11

Residential for sale

CHESTERTOWN

MLS ID: MDKE2005610 Listing Key: 804104828144 Property Type:Residential

5 BED 4 BATH 4,067 ft² Property 11,477 ft² Lot

116 Harlan Loop, Chestertown MD 21620

Offered for $509,000.00

Active
Listed: 2025-08-22

Residential for sale

CHESTERTOWN

MLS ID: MDKE2004992 Listing Key: 803724771650 Property Type:Residential

4 BED 4 BATH 3,540 ft² Property

Little Harbor Way #1, Chestertown MD 21620

Offered for $1,800,000.00

Active
Listed: 2025-04-03

Residential for sale

City Zipcode Search: Chestertown - 21620