Chestertown, MD homes for sale & real estate

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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

NEW CONSTRUCTION

ABOUT THIS HOME
Chestertown, MD Homes for Sale
* * To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to the private balcony. Two additional bedrooms share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. Catch a glimpse of the Chester River from the front porch or upper covered balcony, the perfect place to enjoy morning coffee or

$849,900

3 beds2.5 baths1,980 sq ft

104 Little Harbor Way, Chestertown, MD 21620

In-ground pool • Second-floor laundry • Private balcony

(410) 275-2118

NEW CONSTRUCTION

ABOUT THIS HOME
Chestertown, MD Homes for Sale
Brand new home in Historic Chestertown available for move-in this October. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you’ll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Additional highlights include exclusive financing opportunities with zero down payment loans, paid closing cost programs, and discounted interest rates—making it possible to own this home for less than area rents. Delivered at the asking price as shown in

$259,900

3 beds1.5 baths1,280 sq ft

103 Metcalf Rd, Chestertown, MD 21620

Built 2025 • Listed 105 days

(855) 450-0442

ABOUT THIS HOME
Chestertown, MD Homes for Sale
Come enjoy the this 2 year old home in Historic Chestertown. The home features 3 full bedrooms with 1 1/2 baths . It has an open concept on the main floor, kitchen has beautiful white shaker cabinetry, large island, granite countertops, stainless steel appliances, and luxury vinyl flooring. Large covered patio off the kitchen leading out to a spacious back yard. A new shed recently installed for extra storage. Upstairs features 3 good size bedrooms including a large primary suite. If you are looking for a turn key home with new features, then this home is for you.

$249,950

3 beds1.5 baths1,280 sq ft

112 Metcalf Rd, Chestertown, MD 21620

2 parking spots • Built 2023 • Listed 143 days

(443) 292-6767

ABOUT THIS HOME
Chestertown, MD Homes for Sale
Property record consists of two lots for a total of 2.6 Acres zoned Village. Please notify listing agent if you intend to walk the property.

$29,000

— beds— baths— sq ft

23698 L Rd, Chestertown, MD 21620

Two lots • Zoned village • 2.6 acres

(301) 970-2447

Property at Cloquet Rd, Chestertown, MD 21620

$39,000

— beds— baths— sq ft

Cloquet Rd, Chestertown, MD 21620

(717) 757-7811

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 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 Old Morgnec Rd, Chestertown, MD 21620

$59,000

— beds— baths— sq ft

Old Morgnec Rd, Chestertown, MD 21620

(410) 778-0330

Property at Sandpiper Rd, Chestertown, MD 21620

$9,000

— beds— baths— sq ft

Sandpiper Rd, Chestertown, MD 21620

(410) 778-0330

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 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 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 Tonopah Rd, Chestertown, MD 21620

$40,000

— beds— baths— sq ft

Tonopah Rd, Chestertown, MD 21620

(800) 446-4267

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 Kinglet Rd, Chestertown, MD 21620

$9,000

— beds— baths— sq ft

Kinglet Rd, Chestertown, MD 21620

(443) 215-4663

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 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 Lenapah Rd, Chestertown, MD 21620

$8,000

— beds— baths— sq ft

Lenapah Rd, Chestertown, MD 21620

(410) 220-5745

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 Sheldrake Dr, Chestertown, MD 21620

$15,000

— beds— baths— sq ft

Sheldrake Dr, Chestertown, MD 21620

(410) 778-0330

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 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 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
$562,450
Rock Hall homes for sale
$394,750
Edgewood homes for sale
$292,250
Ridgely homes for sale
$319,000
Joppatowne homes for sale
$379,990
Grasonville homes for sale
$399,900
Chester homes for sale
$509,700
Aberdeen homes for sale
$355,000
Centreville homes for sale
$509,500
Abingdon homes for sale
$370,000
Queenstown homes for sale
$450,000
Galena homes for sale
$326,750
Bowleys Quarters homes for sale
$699,450
Middle River homes for sale
$395,000

Zip Codes

21690 homes for sale
21620 homes for sale
$375,000

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

3.4%

Days on market

Down payment

—

Total homes sold

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