$745,000
- 4 Beds
- 2.5 Baths
- 3,248 Sq Ft
7844 Chester Ct, Chestertown, MD 21620
Retha Arrabal
Doug Ashley Realtors, LLC
(410) 648-9684
$745,000
7844 Chester Ct, Chestertown, MD 21620
Retha Arrabal
Doug Ashley Realtors, LLC
(410) 648-9684
$1,575 per month
517 High St Unit C, Chestertown, MD 21620
Property Id: 2282226Welcome to this spacious 2-bedroom, 1-bath apartment located on the second floor of a classic Chestertown multi-family home. This well-laid-out unit offers comfortable living with attractive architectural details and plenty of natural light throughout. Residents also have access to a shared deck, fenced yard, and welcoming front porch, all just minutes from downtown
$474,000 Sold Apr 03, 2025
220 Blakefield Dr, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $496,066
Last Listing Agent Brenda Fornos Taylor Properties
220 Blakefield Dr, Chestertown, MD 21620$379,000 Under Contract
104 Iris Rd, Chestertown, MD 21620
Retha Arrabal
Doug Ashley Realtors, LLC
(410) 618-0869
$1,550 per month
229 N Kent St Unit 3, Chestertown, MD 21620
Beautifully renovated Two Bedroom/1 Bath Unit. Remodeled down to studs with new gourmet eat-in kitchen with walk-in pantry. Both bedrooms almost equal size, new bathroom, full size washer/dryer added. Central air and heat, new double pane windows, water included in rent, off-street parking. Two Blocks from High Street and Two Blocks from Washington College
Peter Braun Long & Foster Real Estate, Inc.
$375,000 Sold Dec 01, 2025
907 N Meadowview Dr, Chestertown, MD 21620
Last Sold Summary
Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company
907 N Meadowview Dr, Chestertown, MD 21620Est $444,190 Not Listed For Sale
148 Grant Ct, Chestertown, MD 21620
148 Grant Ct, Chestertown, MD 21620$509,000
116 Harlan Loop, Chestertown, MD 21620
Floretta Davis
Samson Properties
(410) 406-6980
$1,400 per month
517 High St Unit B, Chestertown, MD 21620
Property Id: 2282225Welcome to your inviting 1-bedroom, 1-bath apartment in the heart of Chestertown. Located in a classic multi-family home on High Street, this residence offers a comfortable layout with attractive architectural details throughout. Outdoor features include a shared deck, a fenced yard, and a welcoming front porch. This well-located rental is available for $1,400 per
$609,000 Sold Aug 27, 2025
10175 John Carvill Rd, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $612,376
Last Listing Agent Hayley Norris Select Land & Homes, LLC
10175 John Carvill Rd, Chestertown, MD 21620Est $255,987 Not Listed For Sale
104 Metcalf Rd, Chestertown, MD 21620
104 Metcalf Rd, Chestertown, MD 21620$169,000 Pending
21316 Persimmon Dr, Chestertown, MD 21620
Retha Arrabal
Doug Ashley Realtors, LLC
(410) 267-4230
$1,300 per month
101 Morgnec Rd, Chestertown, MD 21620
One, two and three bedroom apartments located near Washington College, wellness/ rehab center, Churches, shopping and a short walk to downtown Chestertown. Short distance to the Chester River and Chesapeake Bay. Immediate Availability.
Herschell Claggett Davis Real Estate, Inc.
$965,500 Sold Mar 21, 2025
225 S Water St Unit 6, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $990,721
Last Listing Agent Tracy Stone Coldwell Banker Chesapeake Real Estate Company
225 S Water St Unit 6, Chestertown, MD 21620Est $430,762 Not Listed For Sale
21357 Belair Ave, Chestertown, MD 21620
21357 Belair Ave, Chestertown, MD 21620$475,000
110 Trafford Dr, Chestertown, MD 21620
Debbi Rivero
RE/MAX Advantage Realty
(410) 406-7422
$305,000 Sold Feb 27, 2025
116 Fairview Dr, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $301,083
Last Listing Agent Jody Baker Cross Street Realtors LLC
116 Fairview Dr, Chestertown, MD 21620Est $381,763 Not Listed For Sale
213 Pine Cove Ln, Chestertown, MD 21620
213 Pine Cove Ln, Chestertown, MD 21620$635,000
108 Little Harbor Way, Chestertown, MD 21620
108 Little Harbor Way, Chestertown, MD 21620$320,000 Sold Mar 26, 2025
6744 Church Hill Rd, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $329,291
Last Listing Agent Sarah Ulrick Rock Hall Properties Real Estate
6744 Church Hill Rd, Chestertown, MD 21620Est $280,264 Not Listed For Sale
7499 Poplar Ave, Chestertown, MD 21620
7499 Poplar Ave, Chestertown, MD 21620$60,000
0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620
0 Georgetown Rd SE Unit MDKE2005218, Chestertown, MD 21620$1,100,000 Sold Jun 30, 2025
209 N Water St, Chestertown, MD 21620
Last Sold Summary
Current Estimated Value $1,148,911
Last Listing Agent Richard Keaveney Cross Street Realtors LLC
209 N Water St, Chestertown, MD 21620Est $368,090 Not Listed For Sale
724 Deep Landing Rd, Chestertown, MD 21620
724 Deep Landing Rd, Chestertown, MD 21620$320,000
222 Dutchess Rd, Chestertown, MD 21620
John Burke
Gunther-McClary Real Estate
(410) 927-1169
$479,495 Sold Apr 25, 2025
720 Aldora Dr Unit 109, Chestertown, MD 21620
Last Sold Summary
Last Listing Agent Terri Hill Builder Solutions Realty
720 Aldora Dr Unit 109, Chestertown, MD 21620Est $403,476 Not Listed For Sale
142 Church Meadow Ct, Chestertown, MD 21620
142 Church Meadow Ct, Chestertown, MD 21620$319,900
24775 Langford Rd, Chestertown, MD 21620
Ryan Fitzwater
RE/MAX Advantage Realty
(410) 835-4609
$287,500 Sold Dec 05, 2025
7483 Shortall St, Chestertown, MD 21620
Last Sold Summary
Last Listing Agent Christine Johnson RE/MAX Executive
7483 Shortall St, Chestertown, MD 21620Est $508,433 Not Listed For Sale
106 Church Aly, Chestertown, MD 21620
106 Church Aly, Chestertown, MD 21620$269,000 Under Contract
24339 Chestertown Rd, Chestertown, MD 21620
Retha Arrabal
Doug Ashley Realtors, LLC
(410) 584-3270
$25,000 Sold Nov 14, 2025
23628 Canvasback Rd, Chestertown, MD 21620
Last Sold Summary
Last Listing Agent Christopher McClary Gunther-McClary Real Estate
23628 Canvasback Rd, Chestertown, MD 21620Est $473,416 Not Listed For Sale
10570 Cogar Rd, Chestertown, MD 21620
10570 Cogar Rd, Chestertown, MD 21620$279,000 Under Contract
134 Char Nor Manor Blvd, Chestertown, MD 21620
John McGlannan
Meredith Fine Properties
(667) 282-1137
$9,500 Sold Aug 19, 2025
0 Millbrook Dr, Chestertown, MD 21620
Last Sold Summary
Last Listing Agent Dee Dee Miller Long & Foster Real Estate, Inc.
0 Millbrook Dr, Chestertown, MD 21620Est $446,807 Not Listed For Sale
209 Blakefield Dr, Chestertown, MD 21620
209 Blakefield Dr, Chestertown, MD 21620$185,000
Lot 9 Prestwick Dr, Chestertown, MD 21620
Lot 9 Prestwick Dr, Chestertown, MD 21620$90,000 Sold May 30, 2025
0 None Unit MDKE2005014, Chestertown, MD 21620
Last Sold Summary
Last Listing Agent William Norris Select Land & Homes, LLC
0 None Unit MDKE2005014, Chestertown, MD 21620Est $619,701 Not Listed For Sale
7675 Quaker Neck Rd, Chestertown, MD 21620
7675 Quaker Neck Rd, Chestertown, MD 21620Showing Results 1 - 40, Page 1 of 18
On average, homes in Chestertown, MD sell after 47 days on the market compared to the national average of 53 days. The median sale price for homes in Chestertown, MD over the last 12 months is $379,950, up 9% from the median home sale price over the previous 12 months.