Chestertown, MD homes for sale & real estate

76 homes

Sort:

Recommended

COMING SOON

10575 Hyala Ct, Chestertown, MD 21620
ABOUT THIS HOME
Chestertown, MD Homes for Sale
Nestled in the tranquil Chesapeake Landing community. This large three bedroom, two bathroom contemporary rancher offers 1978 square feet of comfortable one-level living. This home is situated on a 0.33 acre corner lot with direct access to Worton Creek, minutes from downtown Chestertown. It has an open -concept floor plan with cathedral ceilings. Many upgrades have been done to this house since purchasing. Enjoy the spacious backyard with a fenced in yard. ,

$359,000

3 beds2 baths1,978 sq ft

10575 Hyala Ct, Chestertown, MD 21620

0.33 acre lot • 2 garage spots • Car-dependent

(443) 988-0483

COMING SOON

925 Round Top Rd, Chestertown, MD 21620
ABOUT THIS HOME
Chestertown, MD Homes for Sale
Cute as a button in Chester Harbor! Just the right amount of space. .. a third of an acre yard, three bedrooms and a bath. New in the past few years: flooring throughout, metal standing seam roof, generously sized HVAC, and asphalt driveway sealant. Large two bay shed for storage and lawn tools has electric, and the back deck is ideal for grilling and picking crabs. Low maintenance and move-in ready!

$300,000

3 beds1 bath1,056 sq ft

925 Round Top Rd, Chestertown, MD 21620

0.34 acre lot • Car-dependent

(410) 673-3344

21363 Indiana Ave, Chestertown, MD 21620
21363 Indiana Ave, Chestertown, MD 21620
21363 Indiana Ave, Chestertown, MD 21620
ABOUT THIS HOME
Chestertown, MD Homes for Sale
Low maintenance, coastal cottage in Tolchester on nearly a half acre. Only 2 blocks from the community beach. House was completely renovated inside and out, including the 16 x 20 barn. Three bedrooms, 1 1/2 bathrooms. Start enjoying Summers by the Bay!

$299,900

3 beds1.5 baths896 sq ft

21363 Indiana Ave, Chestertown, MD 21620

0.46 acre lot • Car-dependent

(410) 673-3344

22570 Bay Shore Rd, Chestertown, MD 21620
22570 Bay Shore Rd, Chestertown, MD 21620
22570 Bay Shore Rd, Chestertown, MD 21620
ABOUT THIS HOME
Chestertown, MD Homes for Sale
Lovely countryside Cape Cod on over 3 private acres. Sit on the front porch and enjoy the summer breeze or grill off the back deck and watch the deer in the woods. This home has been meticulously cared for and features a first floor primary bedroom with walk-in closet and ensuite bath with a massive ceramic tile shower. Large formal living room with brick fireplace flows into the kitchen / dining room combo behind with sun-room and back deck. Recent upgrades include: crawl space encapsulation, stainless steel kitchen appliances, downstairs heat pump, backyard fence, solid wood plantation shutters, automatic retractable blinds and more. Quick drive to historic downtown Chestertown. Founded i

$450,000

3 beds2 baths1,788 sq ft

22570 Bay Shore Rd, Chestertown, MD 21620

3.22 acre lot • Car-dependent

(410) 778-0330

624 High St, Chestertown, MD 21620
624 High St, Chestertown, MD 21620
624 High St, Chestertown, MD 21620
ABOUT THIS HOME
Chestertown, MD Homes for Sale
Step into the charm of historic Chestertown with this 2BR/1BA home full of potential. Featuring a screened front porch, spacious layout, and rear alley access, this property is perfect for investors or visionary buyers. Located just blocks from Washington College, the Chester River, downtown shopping, and restaurants, this home offers the ideal setting for a full-time residence, Airbnb, or long-term rental. With some renovation, you can restore it's original character and create serious value in a highly walkable, waterfront community. Sold as-is. No repairs will be made by Seller. Bring your contractor and your imagination— historic opportunity awaits!

$240,000

2 beds1 bath1,290 sq ft

624 High St, Chestertown, MD 21620

2,990 sq ft lot • Very walkable

(844) 837-5274

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

$89,900

2 beds1 bath910 sq ft

132 Prospect St, Chestertown, MD 21620

(877) 328-4400

Property at 9062 Fairlee Rd, Chestertown, MD 21620, 3 beds, 2 baths

$385,000

3 beds2 baths1,344 sq ft

9062 Fairlee Rd, Chestertown, MD 21620

(410) 398-9000

Property at 619 Cannon St, Chestertown, MD 21620, 1 bed, 1 bath

$220,000

1 bed1 bath882 sq ft

619 Cannon St, Chestertown, MD 21620

(410) 778-3779

Property at 26875 Mallard Rd, Chestertown, MD 21620, 3 beds, 3.5 baths

$1,495,000

3 beds3.5 baths3,789 sq ft

26875 Mallard Rd, Chestertown, MD 21620

(410) 639-2118

Property at 24607 Chestertown Rd, Chestertown, MD 21620, 3 beds, 2.5 baths

$375,000

3 beds2.5 baths2,294 sq ft

24607 Chestertown Rd, Chestertown, MD 21620

(410) 778-0330

Property at 310 Hilltop Ln, Chestertown, MD 21620, 3 beds, 2.5 baths

$205,000

3 beds2.5 baths1,216 sq ft

310 Hilltop Ln, Chestertown, MD 21620

(410) 778-3779

Property at 420 Cannon St, Chestertown, MD 21620, 2 beds, 2 baths

$395,000

2 beds2 baths1,080 sq ft

420 Cannon St, Chestertown, MD 21620

(410) 810-0010

Property at 236 Merganser Dr, Chestertown, MD 21620, 1 bed, 1 bath

$213,000

1 bed1 bath900 sq ft

236 Merganser Dr, Chestertown, MD 21620

(410) 320-6785

Property at 21082 Wyoming Ave, Chestertown, MD 21620, 3 beds, 3.5 baths

$1,550,000

3 beds3.5 baths2,699 sq ft

21082 Wyoming Ave, Chestertown, MD 21620

(410) 810-0010

Property at 5179 Quaker Neck Rd, Chestertown, MD 21620, 1 bed, 1 bath

$579,900

1 bed1 bath1,148 sq ft

5179 Quaker Neck Rd, Chestertown, MD 21620

(410) 705-6295

Property at 114 Ryan Ct, Chestertown, MD 21620, 2 beds, 2 baths

$419,000

2 beds2 baths1,496 sq ft

114 Ryan Ct, Chestertown, MD 21620

(301) 970-2447

Property at 110 Philosophers Ter, Chestertown, MD 21620, 2 beds, 1 bath

$199,900

2 beds1 bath896 sq ft

110 Philosophers Ter, Chestertown, MD 21620

(410) 810-0010

Property at Little Harbor Way #1, Chestertown, MD 21620, 3 beds, 2.5 baths

$1,459,000

3 beds2.5 baths2,315 sq ft

Little Harbor Way #1, Chestertown, MD 21620

(410) 275-2118

Property at 300 Hilltop Ln, Chestertown, MD 21620, 3 beds, 2.5 baths

$220,000

3 beds2.5 baths1,200 sq ft

300 Hilltop Ln, Chestertown, MD 21620

(410) 778-0330

Property at 105 High St, Chestertown, MD 21620, 5 beds, 4.5 baths

$1,395,500

5 beds4.5 baths3,243 sq ft

105 High St, Chestertown, MD 21620

(410) 778-0330

Property at 103 Landing Ln, Chestertown, MD 21620, 2 beds, 2.5 baths

$569,000

2 beds2.5 baths2,100 sq ft

103 Landing Ln, Chestertown, MD 21620

(410) 275-2118

Property at 128 Edmore Rd, Chestertown, MD 21620, 4 beds, 2 baths

$425,000

4 beds2 baths2,568 sq ft

128 Edmore Rd, Chestertown, MD 21620

(410) 266-0600

Property at 226 S Water St, Chestertown, MD 21620, 3 beds, 3.5 baths

$998,000

3 beds3.5 baths— sq ft

226 S Water St, Chestertown, MD 21620

(410) 275-2118

Property at 118 Tuxedo Rd, Chestertown, MD 21620, 3 beds, 1 bath

$274,000

3 beds1 bath1,056 sq ft

118 Tuxedo Rd, Chestertown, MD 21620

(410) 810-0010

Property at 21217 Texas Ave, Chestertown, MD 21620, 2 beds, 1 bath

$232,000

2 beds1 bath912 sq ft

21217 Texas Ave, Chestertown, MD 21620

(410) 224-3200

Property at 24576 Langford Rd, Chestertown, MD 21620, 3 beds, 2.5 baths

$845,000

3 beds2.5 baths4,023 sq ft

24576 Langford Rd, Chestertown, MD 21620

(410) 778-9319

Property at 110 Flying Cloud Ct, Chestertown, MD 21620, 3 beds, 2.5 baths

$349,900

3 beds2.5 baths1,856 sq ft

110 Flying Cloud Ct, Chestertown, MD 21620

(410) 505-9700

Property at 866 Washington Ave, Chestertown, MD 21620, 3 beds, 2 baths

$299,000

3 beds2 baths1,224 sq ft

866 Washington Ave, Chestertown, MD 21620

(410) 778-3779

Property at 212 Landing Ln, Chestertown, MD 21620, 3 beds, 3.5 baths

$759,000

3 beds3.5 baths— sq ft

212 Landing Ln, Chestertown, MD 21620

(410) 275-2118

Property at 109 Wilton Rd, Chestertown, MD 21620, 3 beds, 2 baths

$349,900

3 beds2 baths1,392 sq ft

109 Wilton Rd, Chestertown, MD 21620

(443) 215-4663

Property at 11040 Kylie Ln, Chestertown, MD 21620, 4 beds, 3.5 baths

$679,000

4 beds3.5 baths3,684 sq ft

11040 Kylie Ln, Chestertown, MD 21620

(410) 778-0330

Property at 107 Dutchess Rd, Chestertown, MD 21620, 3 beds, 2 baths

$325,000

3 beds2 baths1,380 sq ft

107 Dutchess Rd, Chestertown, MD 21620

(800) 446-4267

Property at 23393 Cacaway Farm Ln, Chestertown, MD 21620, 3 beds, 3.5 baths

$1,450,000

3 beds3.5 baths4,446 sq ft

23393 Cacaway Farm Ln, Chestertown, MD 21620

(410) 275-2118

Property at 116 Pine Chip Rd, Chestertown, MD 21620, 3 beds, 1.5 baths

$515,000

3 beds1.5 baths2,767 sq ft

116 Pine Chip Rd, Chestertown, MD 21620

(410) 778-0330

Property at 117 N Water St Unit 1A, Chestertown, MD 21620, 3 beds, 3 baths

$725,000

3 beds3 baths— sq ft

117 N Water St Unit 1A, Chestertown, MD 21620

(410) 275-2118

Property at 117 N Water St N Unit 3B, Chestertown, MD 21620, 1 bed, 1 bath

$299,900

1 bed1 bath652 sq ft

117 N Water St N Unit 3B, Chestertown, MD 21620

(410) 275-2118

Property at 349 High St, Chestertown, MD 21620, 7 beds, 3.5 baths

$395,000

7 beds3.5 baths3,664 sq ft

349 High St, Chestertown, MD 21620

(410) 778-0330

Property at 117 Water St N Unit 2A, Chestertown, MD 21620, 2 beds, 1 bath

$399,000

2 beds1 bath787 sq ft

117 Water St N Unit 2A, Chestertown, MD 21620

(410) 275-2118

Property at 228 S Water St, Chestertown, MD 21620, 3 beds, 3.5 baths

$898,000

3 beds3.5 baths— sq ft

228 S Water St, Chestertown, MD 21620

(410) 275-2118

Property at 209 River Rd, Chestertown, MD 21620

$135,000

— beds— baths— sq ft

209 River Rd, Chestertown, MD 21620

(410) 810-3900

Property at Buck Neck Rd, Chestertown, MD 21620

$12,000

— beds— baths— sq ft

Buck Neck Rd, Chestertown, MD 21620

(443) 215-4663

Viewing page 1 of 2

Average home prices near Chestertown, MD

Cities

Church Hill homes for sale
$255,000
Stevensville homes for sale
$609,000
Rock Hall homes for sale
$462,000
Edgewood homes for sale
$277,500
Ridgely homes for sale
$359,000
Joppatowne homes for sale
$366,680
Grasonville homes for sale
$399,900
Chester homes for sale
$532,250
Aberdeen homes for sale
$399,999
Centreville homes for sale
$539,000
Abingdon homes for sale
$468,750
Queenstown homes for sale
Galena homes for sale
$324,950
Bowleys Quarters homes for sale
$367,000
Middle River homes for sale
$460,000

Zip Codes

21690 homes for sale
21620 homes for sale
$499,900

Chestertown, MD real estate trends

$490K

Sale price

+21.0%
since last year

$231

Sale $/sq ft

-22.9%
since last year

Under list price

2.3%

Days on market

Down payment

—

Total homes sold

See more Chestertown, MD market insights

More to explore in Chestertown, MD

Featured
Price
Bedroom

How to buy a house in Chestertown, MD

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Maryland

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Become a Lender Partner

Subsidiaries

Rent.

ApartmentGuide

Bay Equity Home Loans

Title Forward

Countries

United States

Canada

Updated January 2023: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, TITLE FORWARD, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.