3 Bedroom 2 Bath homes for sale & real estate in Chestertown, MD

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ABOUT THIS HOME
3 Bedroom 2 Bath Homes 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
3 Bedroom 2 Bath Homes 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
3 Bedroom 2 Bath 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

ABOUT THIS HOME
3 Bedroom 2 Bath Homes for Sale 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

NEW CONSTRUCTION

ABOUT THIS HOME
3 Bedroom 2 Bath Homes for Sale in Chestertown, MD
* * To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath and large walk-in closet. There are two additional bedrooms that share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or pu

$765,900

3 beds2.5 baths1,964 sq ft

#37 Landing Ln, Chestertown, MD 21620

Spa-like bath • Primary suite • Gas fireplace

(410) 275-2118

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 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 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 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 #36 Landing Ln, Chestertown, MD 21620, 3 beds, 2.5 baths

$753,500

3 beds2.5 baths1,964 sq ft

#36 Landing Ln, 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 #35 Landing Ln, Chestertown, MD 21620, 3 beds, 2.5 baths

$786,900

3 beds2.5 baths1,964 sq ft

#35 Landing Ln, Chestertown, MD 21620

(410) 275-2118

Property at 102 Little Harbor Way, Chestertown, MD 21620, 3 beds, 2.5 baths

$839,500

3 beds2.5 baths1,964 sq ft

102 Little Harbor Way, Chestertown, MD 21620

(410) 275-2118

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 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 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

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ABOUT THIS HOME
3 Bedroom 2 Bath Homes for Sale in Chestertown, MD
Investor Opportunity with Historic Charm in Sudlersville If you’ve been waiting for a project with real character, this is the one. This large Victorian is full of potential and just waiting for the right vision to bring it back to life. From the moment you see the wide front porch, you can imagine slow mornings with coffee, quiet evenings with tea, and the timeless charm this home once offered—and can offer again. Set on a generous lot just outside the heart of Sudlersville, the property blends small-town charm with everyday convenience. You’re minutes from Route 301, making commuting or travel simple while still enjoying a quieter pace of life. The home is equipped with

$219,000

3 beds2 baths2,952 sq ft

202 Church St N, Sudlersville, MD 21668

Generous lot • Wide front porch • Separate cottage

(410) 398-9200

ABOUT THIS HOME
3 Bedroom 2 Bath Homes for Sale in Chestertown, MD
Welcome to Silly Manor, a Chesapeake Bay-front property with an abundance of coastal charm and panoramic views. This home is perfectly situated on the coveted Lawton Avenue, one of Kent County's most sought-after neighborhoods. Enjoy stunning sunsets all year-round and direct access to the dynamic waters of the Chesapeake Bay. The open living and dining space offer spectacular views of the Chesapeake. The kitchen opens up to the patio and garden, and has a spacious island for entertaining. The home was designed with a first-floor primary suite, offering convenient (and hard-to-find) one-floor living. There are two additional bedrooms and a full bath on the second floor. Watch the boats glid

$1,100,000

3 beds2.5 baths2,338 sq ft

5980 Lawton Ave, Rock Hall, MD 21661

0.26 acre lot • Garage • Built 1967

(410) 275-2118

ABOUT THIS HOME
3 Bedroom 2 Bath Homes for Sale in Chestertown, MD
Nestled in the charming Church Hill neighborhood, this exquisite Victorian home, built in 1903 and underwent a major renovation in 2025, seamlessly blends historic elegance with modern luxury. With three spacious bedrooms and two full bathrooms, this residence offers a warm and inviting atmosphere, perfect for creating lasting memories. Step inside to discover a thoughtfully designed interior that exudes comfort and sophistication. The living spaces are adorned with waterproof vinyl flooring and enhanced by recessed lighting, creating a cozy ambiance for relaxation or entertaining. The upgraded countertops in the kitchen are complemented by high-end stainless steel appliances, including a g

$328,000

3 beds2 baths1,955 sq ft

112 Walnut St, Church Hill, MD 21623

0.25 acre lot • Built 1903 • Listed 17 days

(301) 970-2447

NEW CONSTRUCTION

ABOUT THIS HOME
3 Bedroom 2 Bath Homes 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

NEW CONSTRUCTION

ABOUT THIS HOME
3 Bedroom 2 Bath Homes for Sale in Chestertown, MD
New Construction Alert! The last two beautiful 3BR, 2.5 bath duplexes under construction on Striper Run in Watermans Estates are now for sale. Nice open 1st floor layout with living, dining & kitchen areas, powder room and separate laundry room. Luxury vinyl plank flooring in the 1st and 2nd levels is 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-able to restaurants, ma

$364,900

3 beds2.5 baths1,626 sq ft

21133 Striper Run, Rock Hall, MD 21661

Storage room • Walk-in closet • Primary suite

(410) 639-4003

NEW CONSTRUCTION

ABOUT THIS HOME
3 Bedroom 2 Bath Homes for Sale 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 24204 Drayton Landing Dr, Worton, MD 21678, 3 beds, 2 baths

$799,000

3 beds2 baths2,176 sq ft

24204 Drayton Landing Dr, Worton, MD 21678

(410) 822-6665

Property at 12400 Woods Rd, Worton, MD 21678, 3 beds, 2 baths

$1,150,000

3 beds2 baths1,944 sq ft

12400 Woods Rd, Worton, MD 21678

(410) 778-3779

Property at 209 3rd St, Crumpton, MD 21628, 3 beds, 2 baths

$375,000

3 beds2 baths1,250 sq ft

209 3rd St, Crumpton, MD 21628

(888) 543-4829

Property at 115 Cemetery Ln, Church Hill, MD 21623, 3 beds, 2 baths

$429,000

3 beds2 baths2,114 sq ft

115 Cemetery Ln, Church Hill, MD 21623

(410) 559-0155

Property at 217 Austin, Centreville, MD 21617, 3 beds, 2.5 baths

$629,000

3 beds2.5 baths2,454 sq ft

217 Austin, Centreville, MD 21617

(410) 647-8000

Property at 25999 Lambs Meadow Rd, Worton, MD 21678, 3 beds, 2.5 baths

$750,000

3 beds2.5 baths3,046 sq ft

25999 Lambs Meadow Rd, Worton, MD 21678

(410) 673-3344

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 5791 S Hawthorne Ave, Rock Hall, MD 21661, 3 beds, 2 baths

$575,000

3 beds2 baths1,536 sq ft

5791 S Hawthorne Ave, Rock Hall, MD 21661

(410) 639-4003

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

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 218 Lakeside Dr, Millington, MD 21651, 3 beds, 2.5 baths

$424,900

3 beds2.5 baths2,184 sq ft

218 Lakeside Dr, Millington, MD 21651

(443) 274-1900

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 21090 W Sharp St #133, Rock Hall, MD 21661, 3 beds, 2 baths

$545,000

3 beds2 baths1,650 sq ft

21090 W Sharp St #133, Rock Hall, MD 21661

(410) 639-2118

3 Bedroom 2 Bath Homes for Sale in Chestertown

There are currently 18 3 bedroom 2 bath 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 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.

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