Chestertown, MD homes for sale & real estate

93 homes

Sort:

Recommended

ABOUT THIS HOME
Chestertown, MD Homes for Sale
Charming Brick Rancher in the Heart of Chestertown Discover this classic brick rancher nestled in one of Chestertown’s established neighborhoods. Enjoy the convenience of being just a short walk or bike ride from downtown, where you’ll find favorite local shops, restaurants, and the beloved Saturday morning Farmers Market. This home offers the perfect blend of small-town charm, walkability, and timeless appeal. This traditional 3-bedroom, 2-full-bath home features an open and inviting living room filled with natural light. All windows have been updated and replaced, the crawl space has been professionally repaired, encapsulated, and equipped with a dehumidifier for added efficie

$363,000

3 beds2 baths1,532 sq ft

303 E Campus Ave, Chestertown, MD 21620

0.34 acre lot • 2 parking spots • Built 1963

(410) 810-0010

OPEN NOV 8, 10AM TO 12PM

ABOUT THIS HOME
Chestertown, MD Homes for Sale
Experience the best of in-town Chestertown living in this custom-built single-level home! The open floor plan features abundant natural light, gleaming hardwood floors and a bright, inviting layout perfect for entertaining or relaxing. The dining room is open to the kitchen which includes some updated appliances, ample cabinet storage, and a breakfast bar. The primary suite has a large walk-in closet and an en-suite bath which now boasts a soaking tub. Step outside to enjoy the large deck, fire pit patio, and fully fenced backyard. This home offers comfort and convenience at every turn. Just a few blocks from Washington College and a short stroll to Downtown Chestertown’s charming res

$419,000

3 beds2.5 baths1,676 sq ft

411 Greenwood Ave, Chestertown, MD 21620

0.28 acre lot • 2 garage spots • Built 2003

(410) 778-0330

ABOUT THIS HOME
Chestertown, MD Homes for Sale
Nestled in the serene Chester Harbor community of Chestertown, MD, 302 Rosin Drive offers an idyllic waterfront lifestyle along the tranquil shores of Rosin Creek. Perched on an elevated lot with stunning vistas of Rosin Creek, this charming home blends classic Eastern Shore character with modern comforts. Imagine mornings with coffee overlooking the water, afternoons kayaking from your backyard and evenings just minutes from historic Chestertown's shops, dining, and Washington College. Seamless indoor-outdoor flow make this the ultimate retreat—perfect for entertaining with indoor and outdoor spaces. This home has a complete in-law-suite perfect for hosting guests, accommodating exte

$574,000

5 beds4 baths3,877 sq ft

302 Rosin Dr, Chestertown, MD 21620

0.86 acre lot • Garage • Built 1996

(410) 778-3779

COMING SOON

ABOUT THIS HOME
Chestertown, MD Homes for Sale
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 • Somewhat walkable

(410) 823-0033

ABOUT THIS HOME
Chestertown, MD Homes for Sale
Nestled in the serene Orchard Hill community, this stunning Craftsman-Colonial offers 3,735 sq. ft. of luxury and comfort. The open, light-filled floor plan showcases rich hardwood floors and elegant finishes throughout. The gourmet kitchen features upgraded countertops, pecan wood-stained cherry cabinetry, stainless steel appliances, including double ovens, a gas cooktop, and a tankless water heater. It opens to the family room with a cozy corner gas fireplace—perfect for entertaining or relaxing. The main level includes an office, primary suite with a large bath and walk-in closet, an additional bedroom and full bath, and a dedicated laundry area. A screened-in porch off the main fl

$695,000

4 beds3.5 baths3,735 sq ft

8951 Orchard Dr, Chestertown, MD 21620

2.81 acre lot • 2 garage spots • Built 2014

(410) 639-4003

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

$920,000

3 beds2 baths2,632 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 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 600 Rosin Dr, Chestertown, MD 21620, 3 beds, 2 baths

$415,000

3 beds2 baths1,300 sq ft

600 Rosin Dr, Chestertown, MD 21620

(410) 810-0010

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 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 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 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 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 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 206 Valley, Chestertown, MD 21620, 4 beds, 2 baths

$615,000

4 beds2 baths2,869 sq ft

206 Valley, Chestertown, MD 21620

(410) 778-0330

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 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 112 Silver Heel Rd, Chestertown, MD 21620, 5 beds, 3.5 baths

$374,900

5 beds3.5 baths2,615 sq ft

112 Silver Heel Rd, Chestertown, MD 21620

(888) 860-7369

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

$2,750,000

5 beds4.5 baths4,305 sq ft

7989 Quaker Neck Rd, Chestertown, MD 21620

(410) 778-0330

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

$878,000

3 beds3.5 baths2,310 sq ft

228 S Water St, Chestertown, MD 21620

(410) 275-2118

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 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 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 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 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

Viewing page 1 of 3

Average home prices near Chestertown, MD

Cities

Church Hill homes for sale
$2,004,500
Stevensville homes for sale
$540,000
Rock Hall homes for sale
$404,700
Edgewood homes for sale
$287,400
Ridgely homes for sale
$346,500
Joppatowne homes for sale
$395,000
Grasonville homes for sale
$422,500
Chester homes for sale
$549,500
Aberdeen homes for sale
$379,000
Centreville homes for sale
$549,900
Abingdon homes for sale
$345,000
Queenstown homes for sale
$409,500
Galena homes for sale
$329,000
Bowleys Quarters homes for sale
$559,450
Middle River homes for sale
$409,000

Zip Codes

21690 homes for sale
21620 homes for sale
$415,000

Chestertown, MD real estate trends

$258K

Sale price

-34.5%
since last year

$181

Sale $/sq ft

-18.7%
since last year

Under list price

2.9%

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

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: 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, 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

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

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.