Homes for sale under $600k in Chestertown, MD

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ABOUT THIS HOME
Homes for sale under $600k in Chestertown, MD
311 Devon Drive is located in Coventry Farms; and being located within the Chestertown town limits offers town utilities. The front entrance welcomes you with an open two-story foyer to the second-floor balcony. To the left of the front foyer is a den and to the right is a formal dining room. The foyer hall leads into a large open area that includes a large eat-in kitchen, sunroom and family room with a gas fireplace. The home's design features an abundance of natural light due to its 9-foot ceilings and full-height glass walls on the first floor's rear. The sunroom and first floor primary suite access onto the rear deck with the view and privacy of mature trees. There is a primary bedroom

$598,000

5 beds3.5 baths3,504 sq ft

311 Devon Dr, Chestertown, MD 21620

Large eat in kitchen • Gas fireplace • Natural light

(410) 810-0010

ABOUT THIS HOME
Homes for sale under $600k in Chestertown, MD
NO HOA OR FRONT FEES: Welcome to 251 Devon Drive located in the desirable Coventry Farms neighborhood. When entering the paved circular driveway, you will find the property meticulously landscaped. The inviting curb appeal welcomes you into the home's foyer where you will find a living room to the left and formal dining room to the right. The foyer then leads you into a spacious kitchen that features a peninsula island with a breakfast bar and cabinetry that offers ample storage and workspace including a separate pantry. Off from the kitchen is a room overlooking the back yard that offers access to the back yard. The primary suite is privately located in rear of home being complete with sh

$595,000

3 beds2.5 baths3,935 sq ft

251 Devon Dr, Chestertown, MD 21620

Separate pantry • Spacious kitchen • Peninsula island

(410) 810-0010

NEW CONSTRUCTION

ABOUT THIS HOME
Homes for sale under $600k in Chestertown, MD
Discover the charm of this stunning new construction home in the desirable Blakefield community, completed in 2025. This beautifully designed Colonial-style residence boasts 4 spacious bedrooms and 3 full bathrooms, offering ample space for relaxation and entertainment. The kitchen is a chef's dream, featuring an island, eat-in space, and modern appliances including a built-in microwave, dishwasher, electric oven/range, and refrigerator. Enjoy cozy breakfasts in the bright breakfast area or host formal dinners in the separate dining room. The luxurious touches continue with walk-in closets, a convenient upper-floor laundry, and a family room that flows effortlessly from the kitchen and a se

$579,000

4 beds3 baths2,400 sq ft

216 Blakefield Dr, Chestertown, MD 21620

1 acre lot • 2 garage spots • Built 2025

(410) 476-2201

ABOUT THIS HOME
Homes for sale under $600k in Chestertown, MD
Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable waterfront community of Chester River Landing. Just a short walk or bike ride into downtown Chestertown, this elegant, turn-key home offers maintenance-free living, great amenities, and easy water access to the Chester River. The welcoming foyer seamlessly flows into the rear den or office which could be converted into a 3rd bedroom. Off the den is the first-floor bedroom and full bath. Enjoy the summer breeze from the private back screened-in porch; recently upgraded with high-tech flex screens and a ceiling waterproofing, keeping the porch dry. The real action is found upstairs. The living room &nda

$539,999

2 beds2.5 baths2,100 sq ft

103 Landing Ln, Chestertown, MD 21620

Easy water access • Electric fireplace • $636 HOA

(410) 778-0330

ABOUT THIS HOME
Homes for sale under $600k in Chestertown, MD
$$THE OWNER MUST RELOCATE. TAKE ADVANTAGE OF THE NEW PRICE IMPROVEMENT! $$ Welcome to Coventry Farms in Chestertown — where comfort, elegance, and space come together in this stunning colonial-style home! Built in 2009 and meticulously maintained, this spacious property offers over 4,000 square feet of finished living space across three levels — including a fully finished basement with a full bath, perfect for entertaining, a guest suite, or a home office setup Curb appeal abounds with an inviting brick front and an attached two-car garage. Step inside to find a bright and open main level featuring a cozy fireplace in the great room, a large formal dining area filled with natura

$519,000

5 beds3.5 baths4,067 sq ft

116 Harlan Loop, Chestertown, MD 21620

Two zone hvac system • Chef's kitchen • 0.26 acre lot

(301) 850-0255

Property at 100 Adela Way, Chestertown, MD 21620, 4 beds, 3.5 baths

$515,000

4 beds3.5 baths3,799 sq ft

100 Adela Way, Chestertown, MD 21620

(410) 266-0600

Property at 8620 Park Dr, Chestertown, MD 21620, 4 beds, 2.5 baths

$499,900

4 beds2.5 baths2,524 sq ft

8620 Park Dr, Chestertown, MD 21620

(410) 810-0010

Property at 515 N Kent St, Chestertown, MD 21620, 4 beds, 2 baths

$499,900

4 beds2 baths2,220 sq ft

515 N Kent St, Chestertown, MD 21620

(410) 778-3779

Property at 222 Mount Vernon Ave, Chestertown, MD 21620, 4 beds, 2 baths

$470,000

4 beds2 baths1,656 sq ft

222 Mount Vernon Ave, Chestertown, MD 21620

(410) 263-3400

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 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 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 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 121 Primrose Rd, Chestertown, MD 21620, 3 beds, 2.5 baths

$399,000

3 beds2.5 baths2,034 sq ft

121 Primrose Rd, Chestertown, MD 21620

(410) 778-0330

Property at 108 Flying Cloud Dr, Chestertown, MD 21620, 4 beds, 2.5 baths

$375,000

4 beds2.5 baths1,936 sq ft

108 Flying Cloud Dr, Chestertown, MD 21620

(410) 778-3779

Property at 204 Rolling Rd, Chestertown, MD 21620, 3 beds, 2 baths

$370,000

3 beds2 baths2,296 sq ft

204 Rolling Rd, Chestertown, MD 21620

(410) 778-0330

Property at 21111 Texas Ave, Chestertown, MD 21620, 3 beds, 2 baths

$370,000

3 beds2 baths1,680 sq ft

21111 Texas Ave, Chestertown, MD 21620

(410) 690-7356

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 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 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 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

$339,000

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 676 Deep Landing Rd, Chestertown, MD 21620, 3 beds, 2.5 baths

$315,000

3 beds2.5 baths1,468 sq ft

676 Deep Landing Rd, Chestertown, MD 21620

(410) 778-3779

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 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 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 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 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 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 7521 Pine Ave, Chestertown, MD 21620, 3 beds, 1 bath

$265,000

3 beds1 bath1,040 sq ft

7521 Pine Ave, Chestertown, MD 21620

(443) 215-4663

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 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 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 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

$165,000

3 beds1.5 baths1,136 sq ft

423 Calvert St, Chestertown, MD 21620

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Homes for sale under $600k in Chestertown

There are currently 40 homes for sale under $600k 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.

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