- Beacon Hill, Annapolis homes for sale
- Centreville, Centreville homes for sale
- Chester, Chester homes for sale
- Chestertown, Chestertown homes for sale
- Church Hill, Church Hill homes for sale
- Fairlee, Chestertown homes for sale
- Georgetown, Chestertown homes for sale
- Gilbert, Aberdeen homes for sale
- Grasonville, Grasonville homes for sale
- Greensboro, Greensboro homes for sale
- Kent Narrows, Chester homes for sale
- Kingstown, Kingstown homes for sale
- Old Philadelphia, Perryman homes for sale
- Queenstown, Queenstown homes for sale
- Ridgely, Ridgely homes for sale
- Rock Hall, Rock Hall homes for sale
- Stepney, Aberdeen homes for sale
- Stevensville, Stevensville homes for sale
- Tolchester, Chestertown homes for sale
- Townsend Village, Townsend homes for sale
Chestertown, MD - single-family homes for sale
39 of 39 results displayed
- Coming Soon
$499,999Coming Soon4 beds 4 baths3,506 sq. ft.331 Devon Dr, CHESTERTOWN, MD 21620
MLS# MDKE2007134Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY - Coming Soon
$495,000Coming Soon3 beds 3 baths1,656 sq. ft.10 Cedar Chase Ct, CHESTERTOWN, MD 21620
MLS# MDKE2007124Listed by: CROSS STREET REALTORS LLC - New
$430,000Active3 beds 3 baths1,520 sq. ft.206 N Mill St, CHESTERTOWN, MD 21620
MLS# MDKE2007160Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY - New
$325,000Active5 beds 2 baths1,802 sq. ft.234 N Kent St, CHESTERTOWN, MD 21620
MLS# MDKE2007128Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY - New
$1,800,000Active4 beds 4 baths3,540 sq. ft.Little Harbor Way #1, CHESTERTOWN, MD 21620
MLS# MDKE2007154Listed by: GUNTHER-MCCLARY REAL ESTATE 
$200,000Pending4 beds 1 baths1,816 sq. ft.223 Mount Vernon Ave, CHESTERTOWN, MD 21620
MLS# MDKE2007080Listed by: CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
$285,000Active3 beds 1 baths960 sq. ft.104 Lincoln Dr, CHESTERTOWN, MD 21620
MLS# MDKE2007032Listed by: RE/MAX EXECUTIVE- Open Sat, 12 to 2pm
$675,000Active5 beds 3 baths2,838 sq. ft.212 Washington Ave, CHESTERTOWN, MD 21620
MLS# MDKE2007016Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY 
$1,195,000Active2 beds 1 baths806 sq. ft.300 And 302 S Mill St, CHESTERTOWN, MD 21620
MLS# MDKE2006850Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$499,900Active3 beds 3 baths2,076 sq. ft.1003 Twin Ct, CHESTERTOWN, MD 21620
MLS# MDKE2006974Listed by: CROSS STREET REALTORS LLC
$259,000Active3 beds 2 baths1,140 sq. ft.115 Chester Arms Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006958Listed by: SAMSON PROPERTIES
$359,000Active2 beds 2 baths1,036 sq. ft.101 S College Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006918Listed by: DOUG ASHLEY REALTORS, LLC
$399,000Pending2 beds 2 baths1,904 sq. ft.7982 Radcliffe Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006950Listed by: DOUG ASHLEY REALTORS, LLC
$370,000Active4 beds 3 baths2,504 sq. ft.123 Trafford Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006970Listed by: CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
$750,000Active3 beds 3 baths2,176 sq. ft.216 Birch Run Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006896Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$480,000Active3 beds 3 baths3,176 sq. ft.129 Trafford Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006878Listed by: ELEVATED REAL ESTATE SOLUTIONS
$325,000Active4 beds 2 baths2,198 sq. ft.200 Manor Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006808Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$325,000Active3 beds 1 baths1,000 sq. ft.896 Washington Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006750Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$629,900Pending3 beds 2 baths2,430 sq. ft.201 River Rd, CHESTERTOWN, MD 21620
MLS# MDQA2017684Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
$85,000Active2 beds 1 baths1,296 sq. ft.234 N College Ave, CHESTERTOWN, MD 21620
MLS# MDKE2006670Listed by: CUMMINGS & CO REALTORS
$372,000Pending4 beds 2 baths1,277 sq. ft.213 Byford Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006026Listed by: DOUG ASHLEY REALTORS, LLC
$340,000Pending4 beds 3 baths1,972 sq. ft.214 Silver Heel Rd, CHESTERTOWN, MD 21620
MLS# MDKE2006498Listed by: CROSS STREET REALTORS LLC
$509,000Active5 beds 4 baths3,816 sq. ft.103 Sutton Way, CHESTERTOWN, MD 21620
MLS# MDKE2006344Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$340,000Pending3 beds 2 baths2,055 sq. ft.202 Waldo Dr, CHESTERTOWN, MD 21620
MLS# MDKE2006260Listed by: DOUG ASHLEY REALTORS, LLC
$829,000Active3 beds 4 baths2,472 sq. ft.106 Queen St S, CHESTERTOWN, MD 21620
MLS# MDKE2006152Listed by: CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
$375,000Active2 beds 1 baths787 sq. ft.117 Water St N #2a, CHESTERTOWN, MD 21620
MLS# MDKE2006166Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$350,000Active1 beds 1 baths850 sq. ft.117 Water St N #2b, CHESTERTOWN, MD 21620
MLS# MDKE2006168Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$1,500,000Active7 beds 5 baths5,400 sq. ft.117 Water St N #1a, 1b, 2a, & 2b, CHESTERTOWN, MD 21620
MLS# MDKE2006158Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$685,000Active3 beds 3 baths3,000 sq. ft.117 Water St N #1a, CHESTERTOWN, MD 21620
MLS# MDKE2006162Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$200,000Active1 beds 1 baths700 sq. ft.117 Water St N #1b, CHESTERTOWN, MD 21620
MLS# MDKE2006164Listed by: TTR SOTHEBY'S INTERNATIONAL REALTY
$750,000Active-- beds 2 baths2,045 sq. ft.201 N Lynchburg St, CHESTERTOWN, MD 21620
MLS# MDKE2006142Listed by: RE/MAX ASSOCIATES-HOCKESSIN
$753,500Active3 beds 3 baths1,964 sq. ft.#36 Landing Ln, CHESTERTOWN, MD 21620
MLS# MDKE2005958Listed by: GUNTHER-MCCLARY REAL ESTATE
$765,900Active3 beds 3 baths1,964 sq. ft.#37 Landing Ln, CHESTERTOWN, MD 21620
MLS# MDKE2005960Listed by: GUNTHER-MCCLARY REAL ESTATE
$786,900Active3 beds 3 baths1,964 sq. ft.#35 Landing Ln, CHESTERTOWN, MD 21620
MLS# MDKE2005956Listed by: GUNTHER-MCCLARY REAL ESTATE
$839,500Active3 beds 3 baths1,964 sq. ft.102 Little Harbor Way, CHESTERTOWN, MD 21620
MLS# MDKE2005950Listed by: GUNTHER-MCCLARY REAL ESTATE
$1,099,900Active4 beds 4 baths2,784 sq. ft.#25 Landing Ln, CHESTERTOWN, MD 21620
MLS# MDKE2005954Listed by: GUNTHER-MCCLARY REAL ESTATE
$275,000Pending2 beds 2 baths920 sq. ft.611 Cannon St, CHESTERTOWN, MD 21620
MLS# MDKE2005906Listed by: SELECT LAND & HOMES, LLC
$849,900Active3 beds 3 baths1,980 sq. ft.104 Little Harbor Way, CHESTERTOWN, MD 21620
MLS# MDKE2005894Listed by: GUNTHER-MCCLARY REAL ESTATE
$1,245,500Active5 beds 5 baths3,243 sq. ft.105 High St, CHESTERTOWN, MD 21620
MLS# MDKE2005890Listed by: COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
Local realty services provided by:Better Homes and Gardens Real Estate GSA Realty
Neighborhoods near Chestertown, MD
Zip codes near Chestertown, MD
- 21001 homes for sale
- 21040 homes for sale
- 21607 homes for sale
- 21610 homes for sale
- 21617 homes for sale
- 21620 homes for sale
- 21623 homes for sale
- 21628 homes for sale
- 21635 homes for sale
- 21640 homes for sale
- 21645 homes for sale
- 21649 homes for sale
- 21651 homes for sale
- 21657 homes for sale
- 21661 homes for sale
- 21667 homes for sale
- 21668 homes for sale
- 21678 homes for sale
- 21913 homes for sale
- 21919 homes for sale
Popular searches near Chestertown, MD
- 2, Church Hill homes for sale
- 2, Kennedyville homes for sale
- 3, Worton (Betterton) homes for sale
- 4, Chestertown homes for sale
- 6, Fairlee homes for sale
- 7, Crumpton homes for sale
- 7, Pomona homes for sale
- Betterton homes for sale
- Butlertown homes for sale
- Chesapeake Landing homes for sale
- Church Hill homes for sale
- Crumpton homes for sale
- Fairlee homes for sale
- Georgetown homes for sale
- Kennedyville homes for sale
- Kingstown homes for sale
- Rock Hall homes for sale
- Still Pond homes for sale
- Tolchester homes for sale
- Worton homes for sale
Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.
© 2026 Better Homes and Gardens Real Estate LLC. An Anywhere Real Estate company. All rights reserved. Better Homes and Gardens® Real Estate is a registered trademark owned by Meredith Operations Corporation, licensed to Better Homes and Gardens Real Estate LLC and used with permission. Better Homes and Gardens Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Listing information is deemed reliable but is not guaranteed accurate.
Each office is independently owned and operated.
Any services or products provided by third parties are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC, or its affiliated companies.
Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.
© 2026 Better Homes and Gardens Real Estate LLC. An Anywhere Real Estate company. All rights reserved. Better Homes and Gardens® Real Estate is a registered trademark owned by Meredith Operations Corporation, licensed to Better Homes and Gardens Real Estate LLC and used with permission. Better Homes and Gardens Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Listing information is deemed reliable but is not guaranteed accurate.
Each office is independently owned and operated.
Any services or products provided by third parties are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC, or its affiliated companies.