3 Bedroom homes for sale & real estate in Chestertown, MD

25 homes

Sort:

Recommended

ABOUT THIS HOME
3 Bedroom Homes 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 • 3 parking spots • Built 1975

(410) 778-0330

COMING SOON

ABOUT THIS HOME
3 Bedroom Homes for Sale in Chestertown, MD
COMING SOON in Tolchester Estates! Discover this well-maintained 2004 rancher located in a water-privileged community with access to the Chesapeake Bay. This charming home offers 3 bedrooms, 2 full baths, and beautiful wood floors throughout. The full unfinished basement is already roughed in for a future bathroom, giving you outstanding potential for added living space. A floored walk-up attic provides even more room for storage or expansion. Additional features include an attached garage and a screened porch perfect for enjoying the outdoors. Tolchester Estates offers the relaxed Eastern Shore lifestyle buyers love—quiet streets and access to the Bay. Showings begin soon—don&r

$370,000

3 beds2 baths1,680 sq ft

21111 Texas Ave, Chestertown, MD 21620

0.41 acre lot • 2 garage spots • Built 2004

(410) 690-7356

OPEN DEC 6, 11AM TO 1PM

ABOUT THIS HOME
3 Bedroom Homes for Sale in Chestertown, MD
Welcome to 121 Primrose Road, a spacious two-story residence offering 2,034 square feet on a . 345-acre lot. This well-built home delivers comfort, functionality, and potential in a peaceful setting just outside downtown Chestertown. Inside, you’ll find three bedrooms and two full baths upstairs plus a convenient half bath on the main level. The main floor features a bright living area, a classic dining space, and a large all-seasons room off the kitchen—perfect for gatherings or relaxing year-round. The full basement offers a blank slate, ready to finish as a recreation room, workshop, or extra storage. A brand-new septic system provides peace of mind, while the attached two-ca

$399,000

3 beds2.5 baths2,034 sq ft

121 Primrose Rd, Chestertown, MD 21620

0.34 acre lot • 2 garage spots • Built 1971

(410) 778-0330

COMING SOON

ABOUT THIS HOME
3 Bedroom Homes for Sale in Chestertown, MD
The one you’ve been waiting for! This 3-bedroom, 1-bath rancher in Quaker Estates offers convenient living just minutes from downtown Chestertown. Features include an oversized pole building with cement floors and electric, plus a long blacktop driveway for plenty of parking. This home is move-in ready, with room for a buyer to add their own personal touches. It has been lovingly maintained with a newer roof, central heat/air, and water softener. Competitively priced and full of potential! More pics will be posted by Dec 4th!

$265,000

3 beds1 bath1,040 sq ft

7521 Pine Ave, Chestertown, MD 21620

0.56 acre lot • 2 garage spots • Built 1969

(443) 215-4663

ABOUT THIS HOME
3 Bedroom Homes for Sale in Chestertown, MD
Kent County welcomes you with a move-in ready home that’s full of updates! This 3-bedroom, 2-bath home sits on nearly a half-acre and is just minutes from downtown Chestertown. Enjoy peace of mind with a newer roof (approximately 5 years old), central heat and air, and a tankless water heater. The home features updated bathrooms, fresh interior paint, and a large laundry room with abundant shelving and space for storage. Outside, you’ll find a spacious yard, storage shed, and access to a wonderful community park with a pavilion and basketball courts. A great combination of comfort, convenience, and value in a desirable location! Kent County has 21 marinas, all within minutes of

$269,000

3 beds2 baths960 sq ft

318 Lincoln, Chestertown, MD 21620

0.49 acre lot • 4 parking spots • Built 1966

(410) 778-0330

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

$1,459,000

3 beds2.5 baths2,231 sq ft

Little Harbor Way #1, Chestertown, MD 21620

(410) 275-2118

Property at 106 Landing Ln, Chestertown, MD 21620, 3 beds, 3.5 baths

$799,900

3 beds3.5 baths2,092 sq ft

106 Landing Ln, Chestertown, MD 21620

(410) 275-2118

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

$359,900

3 beds1 bath1,805 sq ft

23110 Old Fairlee Rd, Chestertown, MD 21620

(855) 450-0442

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

$279,000

3 beds1 bath1,128 sq ft

134 Char Nor Manor Blvd, Chestertown, MD 21620

(410) 714-9166

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

$344,900

3 beds2 baths1,392 sq ft

109 Wilton Rd, Chestertown, MD 21620

(443) 215-4663

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

$245,000

3 beds2 baths1,140 sq ft

100 Metcalf Rd, Chestertown, MD 21620

(443) 829-5828

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

Property at 104 Little Harbor Way, Chestertown, MD 21620, 3 beds, 2.5 baths

$849,900

3 beds2.5 baths1,980 sq ft

104 Little Harbor Way, Chestertown, MD 21620

(410) 275-2118

Property at 251 Devon Dr, Chestertown, MD 21620, 3 beds, 2.5 baths

$595,000

3 beds2.5 baths3,935 sq ft

251 Devon Dr, Chestertown, MD 21620

(410) 810-0010

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 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 112 Metcalf Rd, Chestertown, MD 21620, 3 beds, 1.5 baths

$249,950

3 beds1.5 baths1,280 sq ft

112 Metcalf Rd, Chestertown, MD 21620

(443) 292-6767

Property at 201 Birch Run Rd, Chestertown, MD 21620, 3 beds, 2 baths

$470,000

3 beds2 baths1,588 sq ft

201 Birch Run Rd, Chestertown, MD 21620

(410) 778-0330

Property at 103 Metcalf Rd, Chestertown, MD 21620, 3 beds, 1.5 baths

$259,900

3 beds1.5 baths1,280 sq ft

103 Metcalf Rd, Chestertown, MD 21620

(855) 450-0442

Viewing page 1 of 1

3 Bedroom Homes for Sale in Chestertown

There are currently 25 3 bedroom homes in Chestertown. 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.

More real estate resources for Chestertown, MD

Nearby Cities

Zip Codes

Nearby Cities with 3 Bedroom Homes

More to explore in Chestertown, MD

Featured
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.