Homes for sale under $400k in Chestertown, MD

20 homes

Sort:

Price (high to low)

ABOUT THIS HOME
Homes for sale under $400k 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
Homes for sale under $400k in Chestertown, MD
Motivated Sellers!!! 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, whi

$375,000

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

ABOUT THIS HOME
Homes for sale under $400k 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

ABOUT THIS HOME
Homes for sale under $400k in Chestertown, MD
Beautifully done! A MUST see! UPGRADED 2023-built Smart Home, tucked into a quiet and friendly Chestertown community. Thoughtfully enhanced throughout, the kitchen shines with new quartz countertops, a stylish backsplash, upgraded sink and faucet, and added cabinetry with elegant hardware. Fresh light fixtures bring a warm glow to the living spaces, while the laundry room offers added function with quartz surfaces and extra storage. The powder room has been transformed with a stunning vanity and modern fixtures. The second floor offers four spacious bedrooms and two full baths. As a bonus, this property is a smart home, offering comfort and convenience at your fingertips. Just a short drive

$364,900

4 beds2.5 baths1,936 sq ft

108 Flying Cloud Dr, Chestertown, MD 21620

Quartz countertops • Elegant hardware • Fresh light fixtures

(410) 778-3779

ABOUT THIS HOME
Homes for sale under $400k in Chestertown, MD
Turnkey Perfection! Fully Renovated Ranch Home in Desirable Fairlee! Prepare to be impressed by this stunning ranch home that has undergone a complete, top-to-bottom renovation! Offering 1800 sq. ft. of newly renovated finished interior space, this property is much bigger than it looks and provides true move-in ready convenience with zero deferred maintenance. Upgrades Inside & Out! Enjoy peace of mind knowing the entire house has been meticulously updated with major systems and aesthetic finishes, including: Exterior: New Roof, New Siding, New Windows, and a crisp, modern look. Mechanicals: Brand New Heater, New Central A/C, New Plumbing, New Electrical Service, and a New Hot Water

$349,900

3 beds1 bath1,805 sq ft

23110 Old Fairlee Rd, Chestertown, MD 21620

8,276 sq ft lot • 2 garage spots • Built 1938

(855) 450-0442

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 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 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 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 24775 Langford Rd, Chestertown, MD 21620, 3 beds, 1 bath

$319,900

3 beds1 bath1,008 sq ft

24775 Langford Rd, Chestertown, MD 21620

(302) 378-8700

Property at 119 Darden Rd, Chestertown, MD 21620, 3 beds, 2 baths

$315,000

3 beds2 baths1,424 sq ft

119 Darden Rd, Chestertown, MD 21620

(410) 220-5745

Property at 213 Central Dr, Chestertown, MD 21620, 3 beds, 2 baths

$314,900

3 beds2 baths1,232 sq ft

213 Central Dr, Chestertown, MD 21620

(410) 778-0330

Property at 611 Cannon St, Chestertown, MD 21620, 2 beds, 1.5 baths

$299,000

2 beds1.5 baths920 sq ft

611 Cannon St, Chestertown, MD 21620

(410) 810-3900

Property at 109 Metcalf Rd, Chestertown, MD 21620, 3 beds, 1.5 baths

$264,900

3 beds1.5 baths1,280 sq ft

109 Metcalf Rd, Chestertown, MD 21620

(855) 450-0442

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

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 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 21316 Persimmon Dr, Chestertown, MD 21620, 2 beds, 1 bath

$179,000

2 beds1 bath1,232 sq ft

21316 Persimmon Dr, Chestertown, MD 21620

(410) 810-0010

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

$135,000

3 beds1.5 baths1,136 sq ft

423 Calvert St, Chestertown, MD 21620

Viewing page 1 of 1

End of results

Nearby homes that match your criteria

NEW CONSTRUCTIONVIDEO TOUR

ABOUT THIS HOME
Homes for sale under $400k in Chestertown, MD
OPEN HOUSE, SATURDAY, NOV 1, 10-12 PM! 100% financing is available! The seller is offering a special incentive with in-house financing that includes up to $10,000 toward closing costs or a rate buy‑down. This brand new home in Rock Hall, a historic harbor town celebrated for its Chesapeake Bay shoreline, boating lifestyle and vibrant coastal charm, features four bedrooms and two bathrooms with two thousand square feet of single level living built with high quality craftsmanship and modern upgrades. It offers gleaming hardwood floors, energy efficient windows, a spacious central island with seating, stainless steel appliances, a large porch for entertaining and an attached one car garage. Si

$394,999

4 beds2 baths2,000 sq ft

21733 Centennial Ln, Rock Hall, MD 21661

Home warranty • New construction • Large porch

(410) 729-7700

NEW CONSTRUCTION

ABOUT THIS HOME
Homes for sale under $400k 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

NEW CONSTRUCTION

ABOUT THIS HOME
Homes for sale under $400k 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

ABOUT THIS HOME
Homes for sale under $400k in Chestertown, MD
Convenient one-level living in this 3BR, 2.5 bath rancher. The house needs some cosmetic updates, but has a desirable split bedroom layout with the primary bedroom, bath & closet off the kitchen and two bedrooms and another full bath off the other side of the house. The sun room has a propane stove and exits to a 12' x 15' deck. There's a 10' x 16' shed. (Tractor not included) Nice quiet, in-town location.

$375,000

3 beds2.5 baths1,684 sq ft

21336 Haven Rd, Rock Hall, MD 21661

0.34 acre lot • 2 garage spots • Built 1986

(410) 639-4003

ABOUT THIS HOME
Homes for sale under $400k 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 53 days

(888) 543-4829

NEW CONSTRUCTION

ABOUT THIS HOME
Homes for sale under $400k in Chestertown, MD
New Construction Alert! Last two beautiful 3BR, 2.5 bath duplexes under construction on Striper Run in Watermans Estates. Nice open 1st floor layout with living, dining & kitchen areas, powder room and separate laundry room. Luxury vinyl plank flooring on 1st and 2nd floors, quartz counter tops and stainless appliances are included. Upstairs, there's a primary suite with walk-in closet, full bath, two more spacious bedrooms and another full bath. The 7' x 23' storage room with overhead door provides lots of space for toys and tools. Out back there's a concrete patio and 6 ft vinyl privacy fence. Watermans Estates is an attractive community in the heart of Rock Hall. Walkable or bike-a

$364,900

3 beds2.5 baths1,626 sq ft

21131 Striper Run, Rock Hall, MD 21661

Stainless appliances • Concrete patio • Quartz counter tops

(410) 639-4003

Property at 21133 Striper Run, Rock Hall, MD 21661, 3 beds, 2.5 baths

$364,900

3 beds2.5 baths1,626 sq ft

21133 Striper Run, Rock Hall, MD 21661

(410) 639-4003

Property at 5916 N Main St, Rock Hall, MD 21661, 3 beds, 1.5 baths

$355,000

3 beds1.5 baths1,233 sq ft

5916 N Main St, Rock Hall, MD 21661

(443) 274-1900

Property at 21305 Haven Rd, Rock Hall, MD 21661, 4 beds, 2 baths

$350,000

4 beds2 baths1,499 sq ft

21305 Haven Rd, Rock Hall, MD 21661

(302) 426-2211

Property at 112 Walnut St, Church Hill, MD 21623, 3 beds, 2 baths

$328,000

3 beds2 baths1,955 sq ft

112 Walnut St, Church Hill, MD 21623

(301) 970-2447

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 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 21332 E Sharp St, Rock Hall, MD 21661, 4 beds, 2 baths

$285,000

4 beds2 baths2,368 sq ft

21332 E Sharp St, Rock Hall, MD 21661

(410) 639-4003

Property at 10971 Bottom Rd, Worton, MD 21678, 2 beds, 2 baths

$275,000

2 beds2 baths720 sq ft

10971 Bottom Rd, Worton, MD 21678

(410) 972-4000

Property at 202 Church St N, Sudlersville, MD 21668, 3 beds, 2 baths

$219,000

3 beds2 baths2,952 sq ft

202 Church St N, Sudlersville, MD 21668

(410) 398-9200

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 12765 Still Pond Rd, Still Pond, MD 21667, 3 beds, 2 baths

$180,000

3 beds2 baths2,048 sq ft

12765 Still Pond Rd, Still Pond, MD 21667

(888) 860-7369

Homes for sale under $400k in Chestertown

There are currently 20 homes for sale under $400k 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 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

Zip Codes

Nearby Cities

More to explore in Chestertown, MD

Featured
Price

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.