Cheap homes for sale & real estate in Chestertown, MD

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ABOUT THIS HOME
Cheap Home 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
Cheap Home 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
Cheap Home 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

OPEN SAT, 11AM TO 1PM

ABOUT THIS HOME
Cheap Home for sale 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

$375,000

4 beds2.5 baths1,936 sq ft

108 Flying Cloud Dr, Chestertown, MD 21620

Quartz countertops • Elegant hardware • Fresh light fixtures

(410) 778-3779

COMING SOON

ABOUT THIS HOME
Cheap Home 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

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 304 Hadaway Dr, Chestertown, MD 21620, 4 beds, 2 baths

$425,000

4 beds2 baths1,325 sq ft

304 Hadaway Dr, Chestertown, MD 21620

(410) 823-0033

Property at 112 Silver Heel Dr, Chestertown, MD 21620, 5 beds, 3.5 baths

$369,900

5 beds3.5 baths2,615 sq ft

112 Silver Heel Dr, Chestertown, MD 21620

(888) 860-7369

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 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 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 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 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 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 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 8833 Georgetown Rd, Chestertown, MD 21620, 4 beds, 2 baths

$364,000

4 beds2 baths1,625 sq ft

8833 Georgetown Rd, Chestertown, MD 21620

(410) 778-0330

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 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 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 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 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 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 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 108 S Kent St, Chestertown, MD 21620, 1 bed, 1.5 baths

$315,000

1 bed1.5 baths936 sq ft

108 S Kent St, Chestertown, MD 21620

(410) 778-0330

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 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 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 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 624 High St, Chestertown, MD 21620, 2 beds, 1 bath

$240,000

2 beds1 bath1,290 sq ft

624 High St, Chestertown, MD 21620

(844) 837-5274

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 Georgetown Rd, Chestertown, MD 21620

$89,500

— beds— baths— sq ft

Georgetown Rd, Chestertown, MD 21620

(443) 215-4663

Property at East St, Chestertown, MD 21620

$88,900

— beds— baths— sq ft

East St, Chestertown, MD 21620

(410) 810-3900

Property at Clarissa Rd, Chestertown, MD 21620

$10,000

— beds— baths— sq ft

Clarissa Rd, Chestertown, MD 21620

(703) 378-8810

Property at 404 Spring Rd, Chestertown, MD 21620

$19,500

— beds— baths— sq ft

404 Spring Rd, Chestertown, MD 21620

(302) 217-6692

Property at Elbon Rd, Chestertown, MD 21620

$25,000

— beds— baths— sq ft

Elbon Rd, Chestertown, MD 21620

(301) 244-0117

Property at Buck Neck Landing Rd, Chestertown, MD 21620

$10,000

— beds— baths— sq ft

Buck Neck Landing Rd, Chestertown, MD 21620

(410) 758-0333

Property at Tonopah Rd, Chestertown, MD 21620

$40,000

— beds— baths— sq ft

Tonopah Rd, Chestertown, MD 21620

(800) 446-4267

Property at Johnsontown Rd, Chestertown, MD 21620

$35,000

— beds— baths— sq ft

Johnsontown Rd, Chestertown, MD 21620

(410) 464-5500

Property at Sandpiper Rd, Chestertown, MD 21620

$9,000

— beds— baths— sq ft

Sandpiper Rd, Chestertown, MD 21620

(410) 778-0330

Property at Cogar Rd, Chestertown, MD 21620

$8,000

— beds— baths— sq ft

Cogar Rd, Chestertown, MD 21620

(410) 220-5745

Property at Buck Neck Rd, Chestertown, MD 21620

$9,000

— beds— baths— sq ft

Buck Neck Rd, Chestertown, MD 21620

(443) 215-4663

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Cheap Homes for Sale in Chestertown

There are currently 61 cheap homes for sale in Chestertown at a median listing price of $450K. 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.

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