Chestertown, MD homes for sale & real estate

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ABOUT THIS HOME
Chestertown, MD Homes for Sale
INTOWN Investor Special! This 4-bedroom, 1.5-bath bungalow is full of potential and ready for your vision. Situated on a large, private lot at the end of a quiet street, the home offers solid bones and a detached garage/workshop area that is hard to find! Located just minutes from Chestertown and Washington College. Plenty of space and character, it’s a rare opportunity to create something special in a desirable location. Adjacent to the The Wayne Gilchrest Trail , which is a popular walking trail in Chestertown, MD, also known as the Chestertown Rail Trail. It's a paved, multi-use path that follows the route of a former railway line, connecting various parts of the town. The trail of

$167,000

4 beds1.5 baths1,156 sq ft

141 Prospect St, Chestertown, MD 21620

7,800 sq ft lot • Garage • Built 1900

(410) 778-3779

ABOUT THIS HOME
Chestertown, MD Homes for Sale
$$THE OWNER MUST RELOCATE. TAKE ADVANTAGE OF THE NEW PRICE IMPROVEMENT! $$ 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

$215,000

3 beds2 baths1,666 sq ft

127 Wood Duck Ln, Chestertown, MD 21620

0.53 acre lot • Built 1976 • Listed 68 days

(302) 426-2211

ABOUT THIS HOME
Chestertown, MD Homes for Sale
Back on the market through no fault of the sellers. Home inspection went well. Two bedroom, one bath townhome with a nice view from the living room/patio area. NEW CARPET in living area/hallway on the main level and upstairs! Looks great! Located very close to a public landing and Tolchester Marina, which offers full service. This townhouse has outdoor storage both on the front patio area and the back patio area. New carpet and fresh paint will update this property nicely. Covered storage for bikes/yard toys and more. The townhouse is all electric with a washer/dryer located on the main level. Affordable, and the opportunity to express your own vibe and decorating skills. Call for more i

$179,000

2 beds1 bath1,232 sq ft

21316 Persimmon Dr, Chestertown, MD 21620

Outdoor storage • Tolchester marina • Washer dryer

(410) 810-0010

NEW CONSTRUCTION

ABOUT THIS HOME
Chestertown, MD Homes for Sale
Newly constructed three-bedroom townhome with all the desired attributes. Fantastic water views from the living level and bedrooms! Spacious open living space with warm hardwood floors and a gourmet kitchen. 5-burner induction range, ample cabinet space, and a large island for entertaining. The home is filled with natural light and boasts multiple balconies and a front porch for relaxing. On the second level you'll find two bedrooms and two bathrooms. There's extra room for an office nook. The third bedroom encompasses the entire third floor and has a great view of the Chester River. You'll enjoy the large back balcony with views of historic Chestertown. The third level could be used as the

$878,000

3 beds3.5 baths2,310 sq ft

228 S Water St, Chestertown, MD 21620

Multiple balconies • Large back balcony • Private driveway

(410) 275-2118

Property at 11040 Kylie Ln, Chestertown, MD 21620, 4 beds, 3.5 baths

$649,000

4 beds3.5 baths3,684 sq ft

11040 Kylie Ln, Chestertown, MD 21620

(410) 778-0330

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

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 Cloquet Rd, Chestertown, MD 21620

$39,000

— beds— baths— sq ft

Cloquet Rd, Chestertown, MD 21620

(717) 757-7811

Property at Georgetown Rd, Chestertown, MD 21620

$89,500

— beds— baths— sq ft

Georgetown Rd, Chestertown, MD 21620

(443) 215-4663

Property at 108 Little Harbor Way, Chestertown, MD 21620

$635,000

— beds— baths— sq ft

108 Little Harbor Way, Chestertown, MD 21620

(410) 275-2118

Property at East St, Chestertown, MD 21620

$88,900

— beds— baths— sq ft

East St, Chestertown, MD 21620

(410) 810-3900

Property at Old Morgnec Rd, Chestertown, MD 21620

$59,000

— beds— baths— sq ft

Old Morgnec Rd, Chestertown, MD 21620

(410) 778-0330

Property at Clarissa Rd, Chestertown, MD 21620

$10,000

— beds— baths— sq ft

Clarissa Rd, Chestertown, MD 21620

(703) 378-8810

Property at Sandpiper Rd, Chestertown, MD 21620

$9,000

— beds— baths— sq ft

Sandpiper Rd, Chestertown, MD 21620

(410) 778-0330

Property at Tonopah Rd, Chestertown, MD 21620

$40,000

— beds— baths— sq ft

Tonopah Rd, Chestertown, MD 21620

(800) 446-4267

Property at Cogar Rd, Chestertown, MD 21620

$8,000

— beds— baths— sq ft

Cogar Rd, Chestertown, MD 21620

(410) 220-5745

Property at Beltram Rd, Chestertown, MD 21620

$10,000

— beds— baths— sq ft

Beltram Rd, Chestertown, MD 21620

(410) 488-3124

Property at Fairlee Rd, Chestertown, MD 21620

$75,000

— beds— baths— sq ft

Fairlee Rd, Chestertown, MD 21620

(410) 398-9000

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 Buck Neck Rd, Chestertown, MD 21620

$9,000

— beds— baths— sq ft

Buck Neck Rd, Chestertown, MD 21620

(443) 215-4663

Property at Caulks Field Rd, Chestertown, MD 21620

$150,000

— beds— baths— sq ft

Caulks Field Rd, Chestertown, MD 21620

(703) 237-9500

Property at Lot 9 Prestwick Dr, Chestertown, MD 21620

$185,000

— beds— baths— sq ft

Lot 9 Prestwick Dr, Chestertown, MD 21620

(410) 275-2118

Property at Towhee Rd, Chestertown, MD 21620

$10,000

— beds— baths— sq ft

Towhee Rd, Chestertown, MD 21620

(410) 488-3124

Property at Fish Hatchery Rd, Chestertown, MD 21620

$10,000

— beds— baths— sq ft

Fish Hatchery Rd, Chestertown, MD 21620

(410) 488-3124

Property at Kinglet Rd, Chestertown, MD 21620

$9,000

— beds— baths— sq ft

Kinglet Rd, Chestertown, MD 21620

(443) 215-4663

Property at Georgetown Rd & Cross Rd, Georgetown, MD 21620

$120,000

— beds— baths— sq ft

Georgetown Rd & Cross Rd, Georgetown, MD 21620

(410) 778-0330

Property at Elm Rd, Chestertown, MD 21620

$20,000

— beds— baths— sq ft

Elm Rd, Chestertown, MD 21620

(410) 778-0330

Property at Montgomery Ave, Chestertown, MD 21620

$40,000

— beds— baths— sq ft

Montgomery Ave, Chestertown, MD 21620

(800) 446-4267

Property at Spinnaker Rd, Chestertown, MD 21620

$38,000

— beds— baths— sq ft

Spinnaker Rd, Chestertown, MD 21620

(410) 544-4000

Property at Lenapah Rd, Chestertown, MD 21620

$8,000

— beds— baths— sq ft

Lenapah Rd, Chestertown, MD 21620

(410) 220-5745

Property at Sheldrake Dr, Chestertown, MD 21620

$15,000

— beds— baths— sq ft

Sheldrake Dr, Chestertown, MD 21620

(410) 778-0330

Property at Parcel Buck Neck Ldg Rd, Chestertown, MD 21620

$10,000

— beds— baths— sq ft

Parcel Buck Neck Ldg Rd, Chestertown, MD 21620

(410) 488-3124

Property at 23710 L Rd, Chestertown, MD 21620

$24,000

— beds— baths— sq ft

23710 L Rd, Chestertown, MD 21620

(410) 544-4000

Property at Redfield Rd, Chestertown, MD 21620

$38,000

— beds— baths— sq ft

Redfield Rd, Chestertown, MD 21620

(410) 544-4000

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Average home prices near Chestertown, MD

Cities

Church Hill homes for sale
$328,000
Stevensville homes for sale
$612,000
Rock Hall homes for sale
$410,000
Edgewood homes for sale
$295,000
Ridgely homes for sale
$332,000
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$382,495
Grasonville homes for sale
$405,000
Chester homes for sale
$519,700
Aberdeen homes for sale
$355,000
Centreville homes for sale
$529,000
Abingdon homes for sale
$400,000
Queenstown homes for sale
$450,000
Galena homes for sale
$326,750
Bowleys Quarters homes for sale
$712,450
Middle River homes for sale
$395,000

Zip Codes

21690 homes for sale
21620 homes for sale
$395,000

Chestertown, MD real estate trends

$640K

Sale price

+52.2%
since last year

$239

Sale $/sq ft

+8.1%
since last year

Under list price

Days on market

Down payment

—

Total homes sold

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