Single Story homes for sale & real estate in Chestertown, MD

14 homes

Sort:

Recommended

NEW 28 HRS AGO

ABOUT THIS HOME
Single Story Home for sale in Chestertown, MD:
Great Chestertown location in College Heights. Large corner lot consisting of . 51 acres. This home needs to be remodeled but has great potential and a lot of floor area. The old carpet has been removed down to sub flooring. Lovely sunporch, garage, off street driveway, and entrance courtyard are just a few features! Spacious rooms too! Close to Washington College, Downtown Chestertown, and Shopping Centers.

$333,900

3 beds2.5 baths2,577 sq ft

303 Cedar St, Chestertown, MD 21620

Sunporch • Off street driveway • Corner lot

(410) 810-3900

ABOUT THIS HOME
Single Story Home for sale in Chestertown, MD:
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.

$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

ABOUT THIS HOME
Single Story Home 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

$399,000

4 beds2 baths1,325 sq ft

304 Hadaway Dr, Chestertown, MD 21620

0.41 acre lot • 4 parking spots • Built 1960

(410) 823-0033

ABOUT THIS HOME
Single Story Home 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

ABOUT THIS HOME
Single Story Home 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 8750 Georgetown Rd, Chestertown, MD 21620, 3 beds, 2 baths

$334,000

3 beds2 baths1,900 sq ft

8750 Georgetown Rd, Chestertown, MD 21620

(443) 215-4663

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

$349,900

3 beds1 bath1,805 sq ft

23110 Old Fairlee Rd, Chestertown, MD 21620

(855) 450-0442

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 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 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 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 141 Prospect St, Chestertown, MD 21620, 4 beds, 1.5 baths

$167,000

4 beds1.5 baths1,156 sq ft

141 Prospect St, 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

Viewing page 1 of 1

End of results

Nearby homes that match your criteria

NEW 29 HRS AGO

ABOUT THIS HOME
Single Story Home for sale in Chestertown, MD:
OFFERS DUE BY MONDAY, 12/22 AT 6PM. Don't miss this sweat-equity opportunity! Welcome to 6179 E Dorlon Drive in Rock Hall, MD—a 3-bedroom, 1-bath home full of potential for the right buyer! This property is ideal for investors, renovators, or buyers looking to build equity through updates and improvements. With some TLC, this home offers the chance to customize, renovate, or reposition as a rental or resale investment. Conveniently located just 10 minutes from Chestertown, you’ll enjoy easy access to shopping, dining, Washington College, and local amenities, while still being close to the charm and waterfront lifestyle Rock Hall is known for! Whether you’re looking for you

$145,000

3 beds1 bath1,000 sq ft

6179 E Dorlon Dr, Rock Hall, MD 21661

Waterfront lifestyle • 7,533 sq ft lot • 4 parking spots

(443) 215-4663

COMING SOON

ABOUT THIS HOME
Single Story Home for sale in Chestertown, MD:
Nestled among the farmland and waterways in Kent County is a cul de sac of new homes on Bottom Road just outside of Chestertown. The new 2 bedroom/2 bath single family home in a quiet, serene enclave is a perfect spot for your new home! This fresh and modern home offers glossy granite counters, SS appliances, and a trendy color palette. The quality of this new construction shows in the engineered wood flooring and upgraded 5" baseboards and moldings. The primary bedroom is appointed with a walk-in closet and a shiny new full bath equipped with a double bowl sink/vanity. 1 additional bedroom adds options for an office or study. Enjoy the views of nature with your evening cocktail from t

$275,000

2 beds2 baths720 sq ft

10971 Bottom Rd, Worton, MD 21678

0.24 acre lot • 3 parking spots • Built 2025

(410) 972-4000

NEW CONSTRUCTION

ABOUT THIS HOME
Single Story Home for sale in Chestertown, MD:
COMING SOON! Welcome to 21745 Centennial Lane, Rock Hall, MD — a brand-new 1,415 SF coastal-style rancher perfectly situated just minutes from local marinas, waterfront dining, and unforgettable sunsets. Crafted by JAC Homes, this thoughtfully designed 3-bedroom, 2-bath home combines modern comfort with timeless coastal charm. Step inside to discover an open concept living space filled with natural light and featuring durable LVP flooring throughout. At the heart of the home, the kitchen boasts granite countertops, quality cabinetry, and a seamless flow into the dining and living areas — perfect for entertaining or relaxing after a day on the water. The primary suite includes a

$379,500

3 beds2 baths1,413 sq ft

21745 Centennial Ln, Rock Hall, MD 21661

9,496 sq ft lot • Garage • Built 2026

(410) 479-3993

3D WALKTHROUGH

ABOUT THIS HOME
Single Story Home for sale in Chestertown, MD:
Welcome to 24204 Drayton Landing Drive — a beautifully renovated 3-bedroom, 2-bath home set on 2 peaceful acres in the heart of Kent County on Maryland’s Eastern Shore. Nestled within the desirable Kinnairds Point community, residents enjoy a warm neighborhood setting along with exclusive access to two waterfront common areas: a boat launch and a swim beach. These shared spaces provide the perfect opportunity to experience the Chesapeake Bay and the natural beauty of Still Pond Creek and Churn Creek. This single-story residence offers a spacious first-floor primary suite, an attached 2-car garage, a charming screened porch ideal for unwinding, plus a large composite deck and two

$799,000

3 beds2 baths2,176 sq ft

24204 Drayton Landing Dr, Worton, MD 21678

New siding • Screened porch • New roof

(410) 822-6665

NEW CONSTRUCTION

ABOUT THIS HOME
Single Story Home for sale in Chestertown, MD:
NEW CONSRUCTION. 2 BEDROOM 2 BATH RANCHER LOADED WITH UPGRADES. PICTURES ARE FROM PREVIOUS MODEL BUT FINISHES STILL THE SAME JUST DIFFRENT COLORS. COME SEE FOR YOURSELF. LOADED WITH UPGRADES. WHY BUILD WHEN YOU CAN JUST MOVE IN. UPGRADED LIGHTING PACKAGE, TRAY CEILING, CUSTOME 2 COLOR PAINT, UPGRADED TRIM, THE LIST JUST GOES AND GOES.

$392,400

2 beds2 baths1,160 sq ft

114 W Main St W Main, Sudlersville, MD 21668

Upgraded trim • Tray ceiling • New construction

(410) 643-4663

ABOUT THIS HOME
Single Story Home for sale in Chestertown, MD:
Don’t let this one pass you by! Great opportunity to live near the water. Two blocks to the boat ramp (Chester River). Built in 2021 it compares nicely to new construction. Meticulously kept and maintained. A beautiful rancher in the town of Crumpton on 0.46 acres. The front porch welcomes you to a well -designed open concept 3 BR, 2 full bathrooms home. Natural light illuminates the living space. There is no shortage of amenities: an updated, modern kitchen with SS appliances, under cabinet lighting, granite countertops, whole house sprinkler system. The laundry room adjoins the kitchen. Plenty of room for all your outdoor activities. Easy commute to Route 301, Chestertown, Middlet

$375,000

3 beds2 baths1,250 sq ft

209 3rd St, Crumpton, MD 21628

0.46 acre lot • Built 2021 • Listed 41 days

(888) 543-4829

Property at 11047 Bottom Rd, Worton, MD 21678, 3 beds, 2 baths

$325,000

3 beds2 baths1,200 sq ft

11047 Bottom Rd, Worton, MD 21678

(410) 778-3779

Property at 11150 Old Worton Rd, Worton, MD 21678

$189,000

— beds— baths6,084 sq ft

11150 Old Worton Rd, Worton, MD 21678

(410) 648-6844

Property at 0 will be 11037 Bottom Rd, Worton, MD 21678, 3 beds, 2 baths

$315,000

3 beds2 baths1,300 sq ft

0 will be 11037 Bottom Rd, Worton, MD 21678

(410) 972-4000

Property at 21336 Haven Rd, Rock Hall, MD 21661, 3 beds, 2.5 baths

$375,000

3 beds2.5 baths1,684 sq ft

21336 Haven Rd, Rock Hall, MD 21661

(410) 639-4003

Property at 21733 Centennial Ln, Rock Hall, MD 21661, 4 beds, 2 baths

$394,999

4 beds2 baths2,000 sq ft

21733 Centennial Ln, Rock Hall, MD 21661

(410) 729-7700

Property at 109 Recovery Dr E, Centreville, MD 21617, 3 beds, 2.5 baths

$799,900

3 beds2.5 baths1,974 sq ft

109 Recovery Dr E, Centreville, MD 21617

(301) 970-2447

Property at 21424 Catholic Ave, Rock Hall, MD 21661, 4 beds, 2 baths

$439,000

4 beds2 baths1,247 sq ft

21424 Catholic Ave, Rock Hall, MD 21661

(410) 639-2118

Property at Sparks Corner Sparks Mill At Route 213 Rd, Centreville, MD 21617

$2,428,725

— beds— baths— sq ft

Sparks Corner Sparks Mill At Route 213 Rd, Centreville, MD 21617

(410) 827-8877

Single Story Homes for Sale in Chestertown

There are currently 14 single story homes for sale in Chestertown at a median listing price of $417K. 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 66 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 was also 1 condo, 12 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 Single Story Homes

More to explore in Chestertown, MD

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.