Chestertown, MD homes for sale & real estate

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OPEN TODAY, 6PM TO 7PM

ABOUT THIS HOME
Chestertown, MD Homes for Sale
* Open Every Tuesdy and Thursday from 6 to 7pm * Brand new home in Historic Chestertown available for move-in now. This interior unit 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. Priced at $259,900, this home also comes with a $5,000 builder incentive plus ½% ($1,299) through our lender partnership—making it possible to own for less than area rents. Delivered at the asking price as

$259,900

3 beds1.5 baths1,280 sq ft

115 Metcalf Rd, Chestertown, MD 21620

Walk-in closet • Covered patio • Granite countertops

(855) 450-0442

ABOUT THIS HOME
Chestertown, 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

$429,900

4 beds2.5 baths2,160 sq ft

10781 Fermoy Rd, Chestertown, MD 21620

Fishing pier • Historic downtown • Cleared lot

(855) 450-0442

$339,000

5 beds2.5 baths3,371 sq ft

6746 Quaker Neck Rd, Chestertown, MD 21620

0.68 acre lot • 10 parking spots • Built 1900

(410) 810-0010

ABOUT THIS HOME
Chestertown, MD Homes for Sale
* SELLER IS OFFERING A 1 YEAR HOME WARRANTY WITH ACCEPTABLE OFFER * Welcome to Tolchester Estates, a charming community near the Chesapeake Bay. This 3-bedroom, 2-bath rancher features updated HVAC, gas cooking, an upgraded propane hot water heater, and a recently replaced roof system in March 2026. The property is served by public sewer for added ease and reliability. Step outside to a large rear deck, perfect for entertaining or relaxing while enjoying the peaceful surroundings. The home also offers plenty of storage space in the attic, providing added convenience and functionality. Residents enjoy access to a private community beach and boat ramp. Also conveniently located within walk

$315,000

3 beds2 baths1,232 sq ft

8706 Elm Rd, Chestertown, MD 21620

Large rear deck • Boat ramp • 0.33 acre lot

(410) 810-0010

OPEN OCT 3, 10AM TO 12PMVIDEO TOUR

ABOUT THIS HOME
Chestertown, MD Homes for Sale
Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore’s iconic builders, the home blends historic character with modern comfort through thoughtful updates, new systems, and refined living spaces. Just one block to the waterfront promenade or to morning coffee at Evergrain, the location captures the rhythm of Chestertown living—laid back yet polished, historic yet vibrant. This is more than a home; it is an irreplaceable asset and a true legacy

$1,245,500

5 beds4.5 baths3,243 sq ft

105 High St, Chestertown, MD 21620

Fenced in rear yard • Arched entryways • Detached garage

(410) 778-0330

Property at 956 Washington Ave, Chestertown, MD 21620, 3 beds, 1 bath

$275,000

3 beds1 bath1,248 sq ft

956 Washington Ave, Chestertown, MD 21620

(410) 810-0010

Property at 103 Sutton Way, Chestertown, MD 21620, 5 beds, 3.5 baths

$509,000

5 beds3.5 baths3,816 sq ft

103 Sutton Way, Chestertown, MD 21620

(410) 673-3344

Property at 104 Acorn Dr, Chestertown, MD 21620, 3 beds, 2.5 baths

$275,000

3 beds2.5 baths1,900 sq ft

104 Acorn Dr, Chestertown, MD 21620

(410) 778-3779

Property at 117 Water St N Unit 1A, Chestertown, MD 21620, 3 beds, 3 baths

$685,000

3 beds3 baths3,000 sq ft

117 Water St N Unit 1A, Chestertown, MD 21620

(410) 673-3344

Property at 104 Conley Dr, Chestertown, MD 21620, 3 beds, 1.5 baths

$239,900

3 beds1.5 baths1,280 sq ft

104 Conley Dr, Chestertown, MD 21620

(410) 823-0033

Property at 896 Washington Ave, Chestertown, MD 21620, 3 beds, 1 bath

$325,000

3 beds1 bath1,000 sq ft

896 Washington Ave, Chestertown, MD 21620

(410) 778-0330

Property at 300 and 302 S Mill St, Chestertown, MD 21620, 2 beds, 1 bath

$1,195,000

2 beds1 bath806 sq ft

300 and 302 S Mill St, Chestertown, MD 21620

(410) 778-0330

Property at 121 Metcalf Rd, Chestertown, MD 21620, 3 beds, 1.5 baths

$264,900

3 beds1.5 baths— sq ft

121 Metcalf Rd, Chestertown, MD 21620

(855) 450-0442

Property at 226 S Water St, Chestertown, MD 21620, 3 beds, 3.5 baths

$898,000

3 beds3.5 baths2,172 sq ft

226 S Water St, Chestertown, MD 21620

(410) 275-2118

Property at 117 Water St N Unit 1B, Chestertown, MD 21620, 1 bed, 1 bath

$200,000

1 bed1 bath700 sq ft

117 Water St N Unit 1B, Chestertown, MD 21620

(410) 673-3344

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 117 Water St N Unit 2A, Chestertown, MD 21620, 2 beds, 1 bath

$375,000

2 beds1 bath787 sq ft

117 Water St N Unit 2A, Chestertown, MD 21620

(410) 673-3344

Property at 117 Water St N Unit 2B, Chestertown, MD 21620, 1 bed, 1 bath

$350,000

1 bed1 bath850 sq ft

117 Water St N Unit 2B, Chestertown, MD 21620

(410) 673-3344

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

$385,000

4 beds3 baths2,630 sq ft

23043 Bay Shore Spur, Chestertown, MD 21620

(410) 639-4003

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

$499,999

2 beds2.5 baths2,100 sq ft

103 Landing Ln, Chestertown, MD 21620

(410) 778-0330

Property at Little Harbor Way #1, Chestertown, MD 21620, 3 beds, 2.5 baths

$1,459,000

3 beds2.5 baths2,231 sq ft

Little Harbor Way #1, Chestertown, MD 21620

(410) 275-2118

Property at #37 Landing Ln, Chestertown, MD 21620, 3 beds, 2.5 baths

$765,900

3 beds2.5 baths1,964 sq ft

#37 Landing Ln, Chestertown, MD 21620

(410) 275-2118

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 102 Little Harbor Way, Chestertown, MD 21620, 3 beds, 2.5 baths

$839,500

3 beds2.5 baths1,964 sq ft

102 Little Harbor Way, Chestertown, MD 21620

(410) 275-2118

Property at 201 N Lynchburg St, Chestertown, MD 21620, 1 bath

$750,000

— beds1 bath2,045 sq ft

201 N Lynchburg St, Chestertown, MD 21620

(302) 234-3800

Property at 106 Landing Ln, Chestertown, MD 21620, 3 beds, 3.5 baths

$799,900

3 beds3.5 baths2,092 sq ft

106 Landing Ln, Chestertown, MD 21620

(410) 275-2118

Property at 104 Landing Ln, Chestertown, MD 21620, 3 beds, 3.5 baths

$813,900

3 beds3.5 baths2,192 sq ft

104 Landing Ln, Chestertown, MD 21620

(410) 275-2118

Property at #36 Landing Ln, Chestertown, MD 21620, 3 beds, 2.5 baths

$753,500

3 beds2.5 baths1,964 sq ft

#36 Landing Ln, Chestertown, MD 21620

(410) 275-2118

Property at #35 Landing Ln, Chestertown, MD 21620, 3 beds, 2.5 baths

$786,900

3 beds2.5 baths1,964 sq ft

#35 Landing Ln, Chestertown, MD 21620

(410) 275-2118

Property at #25 Landing Ln, Chestertown, MD 21620, 4 beds, 3.5 baths

$1,099,900

4 beds3.5 baths2,784 sq ft

#25 Landing Ln, Chestertown, MD 21620

(410) 275-2118

Property at 27942 Old Morgnec Rd, Chestertown, MD 21620

$89,000

Land5.17 acres (lot)

27942 Old Morgnec Rd, Chestertown, MD 21620

(410) 275-2118

Property at Undisclosed address, Chestertown, MD 21620

$695,000

Land42.59 acres (lot)

Undisclosed address, Chestertown, MD 21620

(410) 810-3900

Property at Towhee Rd, Chestertown, MD 21620

$50,000

Land0.55 acre (lot)

Towhee Rd, Chestertown, MD 21620

(302) 217-6692

Property at 305 Roosevelt Dr, Chestertown, MD 21620

$45,000

Land0.61 acre (lot)

305 Roosevelt Dr, Chestertown, MD 21620

(301) 970-2447

Property at 8886 Georgetown Rd, Chestertown, MD 21620

$69,900

Land4.03 acres (lot)

8886 Georgetown Rd, Chestertown, MD 21620

(443) 317-8125

Property at 233 Merganser Dr, Chestertown, MD 21620

$60,000

Land0.50 acre (lot)

233 Merganser Dr, Chestertown, MD 21620

(410) 479-3993

Property at 620 Cannon St, Chestertown, MD 21620

$99,999

Land3,096 sq ft (lot)

620 Cannon St, Chestertown, MD 21620

(301) 970-2447

Property at Sandy Bottom Rd, Chestertown, MD 21620

$49,000

Land1.95 acres (lot)

Sandy Bottom Rd, Chestertown, MD 21620

(410) 648-6844

Property at Johnsontown Rd, Chestertown, MD 21620

$10,000

Land0.90 acre (lot)

Johnsontown Rd, Chestertown, MD 21620

(410) 464-5500

Property at 0 Round Top Rd, Chestertown, MD 21620

$200,000

Land5.81 acres (lot)

0 Round Top Rd, Chestertown, MD 21620

(410) 778-0330

Property at 404 Spring Rd, Chestertown, MD 21620

$19,500

Land0.99 acre (lot)

404 Spring Rd, Chestertown, MD 21620

(302) 217-6692

Viewing page 2 of 3

Average home prices near Chestertown, MD

Cities

Church Hill homes for sale
$540,500
Stevensville homes for sale
$575,000
Rock Hall homes for sale
$375,000
Edgewood homes for sale
$219,500
Ridgely homes for sale
$344,950
Joppatowne homes for sale
$426,495
Grasonville homes for sale
$474,450
Chester homes for sale
$595,000
Aberdeen homes for sale
$389,945
Centreville homes for sale
$529,000
Abingdon homes for sale
$324,900
Queenstown homes for sale
$446,950
Galena homes for sale
$939,500
Bowleys Quarters homes for sale
$422,450
Middle River homes for sale
$354,900

Zip Codes

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

Chestertown, MD real estate trends

All Home Types trends in Chestertown, MD

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$308,796

-16.0% YoY | Aug 2026

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Aug 2026

Growth

% YoY

Chestertown, MD

$308,796

-16.0%

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