MLS Listings for Sale in Chestertown, MD

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NEW 11 HRS AGO

ABOUT THIS HOME
MLS Listings for Sale in Chestertown, MD
This 2-bedroom, 1.5-bath bungalow offers a bright, open layout with updates throughout. The home features a sun-filled front room, an eat-in kitchen with new butcher block seating and updated appliances, and a fully renovated bathroom with new tile and a modern vanity. A rear utility room with laundry provides extra storage and access to a small backyard—perfect for gardening or relaxing outdoors. Located within walking distance to Downtown Chestertown’s restaurants, shops, farmers market, and waterfront, this property is a great opportunity to enjoy convenient in-town living.

$299,000

2 beds1.5 baths920 sq ft

611 Cannon St, Chestertown, MD 21620

Updated appliances • New tile • Open layout

(410) 810-3900

OPEN NOV 22, 11AM TO 1PM

ABOUT THIS HOME
MLS Listings for Sale in Chestertown, MD
This masterpiece is finally complete. The Tilley Residence was rebuilt in 1863 and celebrates the Second Empire style reminiscent of the Champs-Élysées in Paris. The neighboring properties on this sought after corner are some of the area's most important including Widehall and the Custom House which was one of the original British Royal Ports of Entry to the Americas. The current owners include one of Kent County's renowned builders and craftsmen who decided to take on this restoration as a passion project to honor its beauty and significance in the community. The home was completely updated in 2024 and 2025 with new HVAC, Electrical, Plumbing, roofing, and wood flooring. The

$1,395,500

5 beds4.5 baths3,243 sq ft

105 High St, Chestertown, MD 21620

Fenced in rear yard • Arched entryways • Detached garage

(410) 778-0330

ABOUT THIS HOME
MLS Listings for Sale in Chestertown, MD
LOCATION! This stunning 4-bedroom, 2-full-bath home is just steps from Washington College and a short stroll to downtown Chestertown. This treasure is full of historic character blended with modern updates! Sellers have INVESTED $60,000 IN RECENT UPGRADES this year, including a brand NEW roof, new electric wiring throughout the entire house, privacy fencing, fresh interior paint, and crawl space moisture barrier with a commercial-grade dehumidifier. The first-floor features airy living, dining, and kitchen areas and a full bath. A bright screen porch with mahogany floor converts to an all-season room overlooking the lovely, fenced backyard, ideal for year-round enjoyment. Upstairs, you&rsq

$499,999

4 beds2 baths1,656 sq ft

222 Mount Vernon Ave, Chestertown, MD 21620

6,450 sq ft lot • Built 1916 • Listed 5 days

(410) 263-3400

COMING SOON

ABOUT THIS HOME
MLS Listings for Sale in Chestertown, MD
Live with ease in this beautifully updated and maintained one floor home in downtown Chestertown. The current owners put a large addition on the house that includes a family room with wood burning stove, sunroom, and primary suite with en suite bathroom and walk in closet. A large laundry room on the main floor and updated kitchen with tons of counter space were other valuable design updates. The basement provides ample partially finished storage space in a completely dry environment due to serious structural improvements, sump pump and french drain system. Bring your hobby down there or your trusty work bench. The roof, HVAC, and hot water heater are all less than 10 years old. The front y

$370,000

3 beds2 baths2,296 sq ft

204 Rolling Rd, Chestertown, MD 21620

0.34 acre lot • Somewhat walkable

(410) 778-0330

ABOUT THIS HOME
MLS Listings for Sale in Chestertown, MD
Welcome to 304 Hadaway Dr. This classic home has been completely reimagined and is ready for it's next chapter. Entering the home you will immediately notice the beautifully refinished original hardwood floors. As you make your way down the hallway past the newly renovated hall bath with custom tile and designer fixtures, you will find 3 spacious bedrooms. The large family room transitions into a perfectly sized dining room and conveniently placed laundry center. The kitchen is absolutely stunning, with stainless Steele appliances, granite countertops, 42" cabinets and new hardwood floors. Moving into the large primary en suit bedroom, you will fall in love with the spa like bath with

$425,000

4 beds2 baths1,325 sq ft

304 Hadaway Dr, Chestertown, MD 21620

0.41 acre lot • 4 parking spots • Built 1960

(410) 823-0033

Property at 112 Silver Heel Dr, Chestertown, MD 21620, 5 beds, 3.5 baths

$369,900

5 beds3.5 baths2,615 sq ft

112 Silver Heel Dr, Chestertown, MD 21620

(888) 860-7369

Property at 303 E Campus Ave, Chestertown, MD 21620, 3 beds, 2 baths

$363,000

3 beds2 baths1,532 sq ft

303 E Campus Ave, Chestertown, MD 21620

(410) 810-0010

Property at 10121 Fairlee Rd, Chestertown, MD 21620, 6 beds, 5 baths

$2,350,000

6 beds5 baths4,954 sq ft

10121 Fairlee Rd, Chestertown, MD 21620

(410) 778-0330

Property at 492 Pear Tree Point Rd, Chestertown, MD 21620, 3 beds, 2 baths

$875,000

3 beds2 baths3,720 sq ft

492 Pear Tree Point Rd, Chestertown, MD 21620

(410) 778-0330

Property at 7844 Chester Ct, Chestertown, MD 21620, 4 beds, 2.5 baths

$770,000

4 beds2.5 baths3,248 sq ft

7844 Chester Ct, Chestertown, MD 21620

(410) 810-0010

Property at 318 Lincoln, Chestertown, MD 21620, 3 beds, 2 baths

$269,000

3 beds2 baths960 sq ft

318 Lincoln, Chestertown, MD 21620

(410) 778-0330

Property at 206 S Water St, Chestertown, MD 21620, 4 beds, 3.5 baths

$619,000

4 beds3.5 baths2,008 sq ft

206 S Water St, Chestertown, MD 21620

(301) 967-3344

Property at 109 S College Ave, Chestertown, MD 21620, 3 beds, 2.5 baths

$449,900

3 beds2.5 baths1,216 sq ft

109 S College Ave, Chestertown, MD 21620

(410) 778-3779

Property at 23069 Raleigh Rd, Chestertown, MD 21620, 2 beds, 1.5 baths

$175,000

2 beds1.5 baths1,160 sq ft

23069 Raleigh Rd, Chestertown, MD 21620

(410) 972-4000

Property at 8620 Park Dr, Chestertown, MD 21620, 4 beds, 2.5 baths

$499,900

4 beds2.5 baths2,524 sq ft

8620 Park Dr, Chestertown, MD 21620

(410) 810-0010

Property at 8750 Georgetown Rd, Chestertown, MD 21620, 3 beds, 2 baths

$339,000

3 beds2 baths1,900 sq ft

8750 Georgetown Rd, Chestertown, MD 21620

(443) 215-4663

Property at 222 Dutchess Rd, Chestertown, MD 21620, 3 beds, 1.5 baths

$320,000

3 beds1.5 baths1,096 sq ft

222 Dutchess Rd, Chestertown, MD 21620

(410) 275-2118

Property at 101 Birch Run Rd, Chestertown, MD 21620, 3 beds, 2 baths

$499,999

3 beds2 baths1,961 sq ft

101 Birch Run Rd, Chestertown, MD 21620

(410) 287-3629

Property at 100 Adela Way, Chestertown, MD 21620, 4 beds, 3.5 baths

$515,000

4 beds3.5 baths3,799 sq ft

100 Adela Way, Chestertown, MD 21620

(410) 266-0600

Property at 10230 John Carvill Rd, Chestertown, MD 21620, 4 beds, 3 baths

$750,000

4 beds3 baths2,350 sq ft

10230 John Carvill Rd, Chestertown, MD 21620

(410) 822-7556

Property at 107 Malone Ave, Chestertown, MD 21620, 3 beds, 1 bath

$290,000

3 beds1 bath1,200 sq ft

107 Malone Ave, Chestertown, MD 21620

(866) 987-3937

Property at 10781 Fermoy Rd, Chestertown, MD 21620, 3 beds, 3 baths

$449,900

3 beds3 baths2,160 sq ft

10781 Fermoy Rd, Chestertown, MD 21620

(855) 450-0442

Property at 8833 Georgetown Rd, Chestertown, MD 21620, 4 beds, 2 baths

$314,000

4 beds2 baths1,625 sq ft

8833 Georgetown Rd, Chestertown, MD 21620

(410) 778-0330

Property at 517 High St, Chestertown, MD 21620, 3 beds

$389,900

3 beds— baths1,728 sq ft

517 High St, Chestertown, MD 21620

(410) 275-8101

Property at 7653 Broad Neck Rd, Chestertown, MD 21620, 4 beds, 3 baths

$375,000

4 beds3 baths1,790 sq ft

7653 Broad Neck Rd, Chestertown, MD 21620

(410) 822-6665

Property at 110 Tuxedo Rd, Chestertown, MD 21620, 3 beds, 2.5 baths

$269,000

3 beds2.5 baths1,664 sq ft

110 Tuxedo Rd, Chestertown, MD 21620

(410) 823-0033

Property at 200 Washington Ave, Chestertown, MD 21620, 4 beds, 3.5 baths

$695,000

4 beds3.5 baths2,917 sq ft

200 Washington Ave, Chestertown, MD 21620

(410) 778-3779

Property at 423 Calvert St, Chestertown, MD 21620, 3 beds, 1.5 baths

$165,000

3 beds1.5 baths1,136 sq ft

423 Calvert St, Chestertown, MD 21620

Property at 132 Prospect St, Chestertown, MD 21620, 2 beds, 1 bath

$62,400

2 beds1 bath910 sq ft

132 Prospect St, Chestertown, MD 21620

(877) 328-4400

Property at 7989 Quaker Neck Rd, Chestertown, MD 21620, 5 beds, 4.5 baths

$2,500,000

5 beds4.5 baths4,305 sq ft

7989 Quaker Neck Rd, Chestertown, MD 21620

(410) 778-0330

Property at 23110 Old Fairlee Rd, Chestertown, MD 21620, 3 beds, 1 bath

$369,900

3 beds1 bath1,805 sq ft

23110 Old Fairlee Rd, Chestertown, MD 21620

(855) 450-0442

Property at 127 Wood Duck Ln, Chestertown, MD 21620, 3 beds, 2 baths

$215,000

3 beds2 baths1,666 sq ft

127 Wood Duck Ln, Chestertown, MD 21620

(302) 426-2211

Property at 165 Char Nor Manor Blvd, Chestertown, MD 21620, 4 beds, 2.5 baths

$429,999

4 beds2.5 baths2,258 sq ft

165 Char Nor Manor Blvd, Chestertown, MD 21620

(443) 274-1900

Property at 118 Little Harbor Way #201, Chestertown, MD 21620, 2 beds, 2.5 baths

$675,000

2 beds2.5 baths1,550 sq ft

118 Little Harbor Way #201, Chestertown, MD 21620

(410) 778-3779

Property at 134 Char Nor Manor Blvd, Chestertown, MD 21620, 3 beds, 1 bath

$285,000

3 beds1 bath1,128 sq ft

134 Char Nor Manor Blvd, Chestertown, MD 21620

(410) 714-9166

Property at 116 Harlan Loop, Chestertown, MD 21620, 5 beds, 3.5 baths

$519,000

5 beds3.5 baths4,067 sq ft

116 Harlan Loop, Chestertown, MD 21620

(301) 850-0255

Property at 23043 Bay Shore Spur, Chestertown, MD 21620, 4 beds, 3 baths

$325,000

4 beds3 baths2,630 sq ft

23043 Bay Shore Spur, Chestertown, MD 21620

(410) 639-4003

Property at 300 Hickory Ln, Chestertown, MD 21620, 5 beds, 3.5 baths

$1,198,000

5 beds3.5 baths3,640 sq ft

300 Hickory Ln, Chestertown, MD 21620

(410) 275-2118

Property at 100 Metcalf Rd, Chestertown, MD 21620, 3 beds, 2 baths

$250,000

3 beds2 baths1,140 sq ft

100 Metcalf Rd, Chestertown, MD 21620

(443) 829-5828

Property at 5700 Johnsontown Rd, Chestertown, MD 21620, 3 beds, 1 bath

$110,000

3 beds1 bath1,144 sq ft

5700 Johnsontown Rd, Chestertown, MD 21620

(844) 837-5274

Property at 118 Little Harbor Way #202, Chestertown, MD 21620, 3 beds, 2 baths

$695,000

3 beds2 baths1,600 sq ft

118 Little Harbor Way #202, Chestertown, MD 21620

(410) 822-6665

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MLS Listings for Sale in Chestertown

There are currently 86 mls listings for sale in Chestertown at a median listing price of $450K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Chestertown stay on the market for 70 days and receive 1 offers. This map is refreshed with the newest listings in Chestertown every 15 minutes.

In the past month, 4 homes have been sold in Chestertown. In addition to houses in Chestertown, there were also 3 condos, 9 townhouses, and 2 multi-family units for sale in Chestertown last month. Find your dream home in Chestertown using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Chestertown are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Chestertown. Our Chestertown real estate stats and trends will give you more information about home buying and selling trends in Chestertown. If you're looking to sell your home in the Chestertown area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Chestertown with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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