21620, MD homes for sale & real estate

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COMING SOON

ABOUT THIS HOME
21620, MD Homes for Sale
Gobbler Hill, circa 1858 with an addition built in 1989, sits like a jewel atop one of the highest points in Kent County. Listed on the National Historic Registry, the transitional architecture is an excellent example of late Greek Revival to early Italianate. The property consists of four parcels totaling over 65 acres. Wildlife abounds on the fields of native prairie grasses, wild flowers, woods, approximately 20 tilled acres and a large pond. Impeccable attention was payed to maintaining the historic character of both the interior and exterior. From the Lincrusta wall covering, 19th century faux wood finishing, plaster medallions, white and sugar pine wood floors and crown molding on the

$2,350,000

6 beds5 baths4,954 sq ft

10121 Fairlee Rd, Chestertown, MD 21620

65.47 acre lot • Pool • Car-dependent

(410) 778-0330

OPEN NOV 4, 11AM TO 1PM

ABOUT THIS HOME
21620, MD Homes for Sale
Beautifully Updated Home in a Serene Setting! Welcome to this stunning home filled with thoughtful improvements and timeless charm. The spacious Florida room overlooks a private, beautifully landscaped backyard — your own personal oasis. This room offers unlimited views of the back yard, which was designed in collaboration with a professional landscaper, this garden is a delight in every season and a true haven for butterflies and hummingbirds. You will delight in an outdoor sitting area under a lovely shade tree. The main level features gleaming hardwood floor, a semi-open floor plan with a cozy fireplace perfect for cool evenings, and abundant natural light that creates a calming at

$770,000

4 beds2.5 baths3,248 sq ft

7844 Chester Ct, Chestertown, MD 21620

Outdoor sitting area • Large island • Owned solar panels

(410) 810-0010

COMING SOON

ABOUT THIS HOME
21620, MD Homes for Sale
Welcome home to relaxed Eastern Shore living in the waterfront community of Chesapeake Landing. This beautifully updated 2,140 sq ft Cape Cod offers the perfect blend of charm and modern comfort with 3 bedrooms, 2.5 baths, and a welcoming floor plan designed for everyday life. The main level features new flooring throughout, a spacious living area, formal dining room, and a renovated country kitchen with new appliances, new counters, and plenty of space for gathering. A main-level bedroom adds flexibility for guests or one-level living. Enjoy morning coffee or evening sunsets on the back deck overlooking the open, cleared 0.39-acre lot—perfect for gardening or outdoor fun. Additional

$449,900

3 beds3 baths2,160 sq ft

10781 Fermoy Rd, Chestertown, MD 21620

0.39 acre lot • Car-dependent

(855) 450-0442

NEW 24 HRS AGO

ABOUT THIS HOME
21620, MD Homes for Sale
Live in the heart of Chestertown’s Historic District—see your boat from your front porch! Beautifully rebuilt and expanded, this versatile home offers 3 1/2 baths and over 2,000 sq. ft. of finished living space. The rear addition features a sunroom/mudroom with separate entrance leading to a guest suite with walk-in closet and full bath. Upstairs, enjoy a second-story waterview deck—built strong enough to support a hot tub or additional living area (double 2x8 joists per owner). Andersen composite dual-pane windows with plantation shutters offer energy efficiency and easy operation. Ample storage includes two walk-in closets plus a walk-in attic. Located on desirable Wate

$619,000

4 beds3.5 baths2,008 sq ft

206 S Water St, Chestertown, MD 21620

Sunroom mudroom • Heartland appliances • Waterview deck

(301) 967-3344

ABOUT THIS HOME
21620, MD Homes for Sale
Welcome to 492 Pear Tree Point Road: an exceptional Chester River waterfront home with unique upriver views. Spacious rooms, gorgeous cherry hardwoods, a back deck to die for, private setting, and with space to add; this home has it all! Good water depth for a dock and center console. Nearly an acre of elevated land - out of the flood zone - that backs to picturesque horse pasture. The main floor features a huge open-concept kitchen and living/dining room space which naturally flows onto the unmatched second-story wrap-around deck; perfect for crab feasts, bbq, and watching summer sunsets. Perched on the second floor is the primary suite with private Romeo and Juliet style balcony high abo

$920,000

3 beds2 baths2,632 sq ft

492 Pear Tree Point Rd, Chestertown, MD 21620

0.91 acre lot • 2 garage spots • Built 2001

(410) 778-0330

Property at 8951 Orchard Dr, Chestertown, MD 21620, 4 beds, 3.5 baths

$695,000

4 beds3.5 baths3,735 sq ft

8951 Orchard Dr, 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 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 411 Greenwood Ave, Chestertown, MD 21620, 3 beds, 2.5 baths

$419,000

3 beds2.5 baths1,676 sq ft

411 Greenwood Ave, Chestertown, MD 21620

(410) 778-0330

Property at 600 Rosin Dr, Chestertown, MD 21620, 3 beds, 2 baths

$415,000

3 beds2 baths1,300 sq ft

600 Rosin Dr, Chestertown, MD 21620

(410) 810-0010

Property at 221 Old Bridge Rd, Chestertown, MD 21620, 3 beds, 2 baths

$369,900

3 beds2 baths1,851 sq ft

221 Old Bridge Rd, Chestertown, MD 21620

(410) 673-3344

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 101 Birch Run Rd, Chestertown, MD 21620, 3 beds, 2 baths

$525,000

3 beds2 baths1,961 sq ft

101 Birch Run Rd, Chestertown, MD 21620

(410) 287-3629

Property at 206 Valley, Chestertown, MD 21620, 4 beds, 2 baths

$639,900

4 beds2 baths2,869 sq ft

206 Valley, Chestertown, MD 21620

(410) 778-0330

Property at 517 High St, Chestertown, MD 21620, 3 beds

$389,900

3 beds— baths1,728 sq ft

517 High St, Chestertown, MD 21620

(410) 275-8101

Property at 10761 Kasota Rd, Chestertown, MD 21620, 3 beds, 3 baths

$895,000

3 beds3 baths2,582 sq ft

10761 Kasota Rd, Chestertown, MD 21620

(410) 778-0330

Property at 7653 Broad Neck Rd, Chestertown, MD 21620, 4 beds, 3 baths

$375,000

4 beds3 baths1,790 sq ft

7653 Broad Neck Rd, Chestertown, MD 21620

(410) 822-6665

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

$314,000

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

$275,000

3 beds2.5 baths1,664 sq ft

110 Tuxedo Rd, Chestertown, MD 21620

(410) 823-0033

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

$374,900

5 beds3.5 baths2,615 sq ft

112 Silver Heel Rd, Chestertown, MD 21620

(888) 860-7369

Property at 200 Washington Ave, Chestertown, MD 21620, 4 beds, 3.5 baths

$695,000

4 beds3.5 baths2,917 sq ft

200 Washington Ave, Chestertown, MD 21620

(410) 778-3779

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 118 Little Harbor Way #201, Chestertown, MD 21620, 2 beds, 2.5 baths

$675,000

2 beds2.5 baths1,550 sq ft

118 Little Harbor Way #201, Chestertown, MD 21620

(410) 778-3779

Property at 228 S Water St, Chestertown, MD 21620, 3 beds, 3.5 baths

$878,000

3 beds3.5 baths2,310 sq ft

228 S Water St, Chestertown, MD 21620

(410) 275-2118

Property at 5700 Johnsontown Rd, Chestertown, MD 21620, 3 beds, 1 bath

$110,000

3 beds1 bath1,144 sq ft

5700 Johnsontown Rd, Chestertown, MD 21620

(844) 837-5274

Property at 119 Darden Rd, Chestertown, MD 21620, 3 beds, 2 baths

$315,000

3 beds2 baths1,424 sq ft

119 Darden Rd, Chestertown, MD 21620

(410) 220-5745

Property at 7989 Quaker Neck Rd, Chestertown, MD 21620, 5 beds, 4.5 baths

$2,750,000

5 beds4.5 baths4,305 sq ft

7989 Quaker Neck Rd, Chestertown, MD 21620

(410) 778-0330

Property at 23110 Old Fairlee Rd, Chestertown, MD 21620, 3 beds, 1 bath

$369,900

3 beds1 bath1,805 sq ft

23110 Old Fairlee Rd, Chestertown, MD 21620

(855) 450-0442

Property at 23043 Bay Shore Spur, Chestertown, MD 21620, 4 beds, 3 baths

$350,000

4 beds3 baths2,630 sq ft

23043 Bay Shore Spur, Chestertown, MD 21620

(410) 639-4003

Property at 134 Char Nor Manor Blvd, Chestertown, MD 21620, 3 beds, 1 bath

$319,000

3 beds1 bath1,128 sq ft

134 Char Nor Manor Blvd, Chestertown, MD 21620

(410) 714-9166

Property at 300 Hickory Ln, Chestertown, MD 21620, 5 beds, 3.5 baths

$1,198,000

5 beds3.5 baths3,640 sq ft

300 Hickory Ln, Chestertown, MD 21620

(410) 275-2118

Property at 165 Char Nor Manor Blvd, Chestertown, MD 21620, 4 beds, 2.5 baths

$450,000

4 beds2.5 baths2,258 sq ft

165 Char Nor Manor Blvd, Chestertown, MD 21620

(443) 274-1900

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 907 N Meadowview Dr, Chestertown, MD 21620, 3 beds, 2.5 baths

$410,000

3 beds2.5 baths1,842 sq ft

907 N Meadowview Dr, Chestertown, MD 21620

(410) 778-0330

Property at 300 Merganser Dr, Chestertown, MD 21620, 3 beds, 1 bath

$190,000

3 beds1 bath1,260 sq ft

300 Merganser Dr, Chestertown, MD 21620

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 103 Landing Ln, Chestertown, MD 21620, 2 beds, 2.5 baths

$559,000

2 beds2.5 baths2,100 sq ft

103 Landing Ln, Chestertown, MD 21620

(410) 778-0330

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 116 Harlan Loop, Chestertown, MD 21620, 5 beds, 3.5 baths

$529,000

5 beds3.5 baths4,067 sq ft

116 Harlan Loop, Chestertown, MD 21620

(301) 850-0255

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

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Average home prices near 21620, MD

Cities

Zip Codes

21620, MD real estate trends

$373K

Sale price

+4.9%
since last year

$241

Sale $/sq ft

+10.0%
since last year

Under list price

2.5%

Days on market

50.5

Down payment

—

Total homes sold

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