21620, MD homes for sale & real estate

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NEW 8 HRS AGO

ABOUT THIS HOME
21620, MD Homes for Sale
Space, convenience, and value just minutes from downtown Chestertown! This spacious 4-bedroom, 2.5-bath Colonial in Coventry Farms checks the boxes for buyers looking for room to spread out without giving up convenience. The main level features a comfortable living room, dining area, kitchen, and half bath. Upstairs, you’ll find four bedrooms, including a spacious primary suite with a walk-in closet and en suite bath with dual vanities. Need even more space? The mostly finished basement adds approximately 600 sq. ft. of flexible living space, with plumbing already roughed in for a future bathroom. Plus the attached two car garage with plenty of room to park your vehicle and still have

$375,000

4 beds2.5 baths2,504 sq ft

123 Trafford Dr, Chestertown, MD 21620

Walk-in closet • Plumbing roughed in • En suite bath

(443) 215-4663

COMING SOON

ABOUT THIS HOME
21620, MD Homes for Sale
Welcome home to this beautifully maintained and thoughtfully updated residence nestled at the end of a peaceful cul-de-sac! Originally built in 2002 and extensively renovated in 2020, this home offers the perfect combination of timeless design, modern updates, and comfortable living. Hickory flooring flows throughout the main living areas and bedrooms, while LVP flooring provides durability and easy maintenance in all bathrooms and the laundry room. The heart of the home is the impressive gourmet kitchen, featuring quartz countertops, a granite-topped island, 5-burner propane range, double wall ovens, built-in microwave, pot filler, farmhouse sink, beautiful backsplash, and abundant cabinet

$524,900

3 beds2.5 baths2,076 sq ft

1003 Twin Ct, Chestertown, MD 21620

Quartz countertops • Gourmet kitchen • Double wall ovens

(410) 778-3779

COMING SOON

ABOUT THIS HOME
21620, MD Homes for Sale
Set within a stately 1800s waterfront home, this beautifully renovated one-bedroom condominium offers an effortless life along the Chester River. Begin your mornings with river views, spend shaded afternoons beneath the trees, or retreat to the floating dock for sunbathing and quiet reflection. With an updated kitchen and bath, kayak storage, off-street parking, and downtown Chestertown’s shops and restaurants just one block away, 117 N Water Street, Unit 3B is a maintenance-free escape within 90 minutes of Washington, D. C. , and Philadelphia.

$295,000

1 bed1 bath— sq ft

117 N Water St Unit 3B, Chestertown, MD 21620

Waterfront home • Kayak storage • Updated kitchen

(410) 778-0330

ABOUT THIS HOME
21620, MD Homes for Sale
Welcome home to 7982 Radcliffe Road! This charming corner-lot offers a perfect blend of character and modern comfort. Built in 1978- this well maintained 2 bedroom, 2 bathroom home feels more of a newer era. Inside you'll find a spacious living room with plenty of room to relax by the fireplace or entertain! The oversized garage offers amazing storage and features an office space that is closed off. Outside, you can enjoy the nice-sized yard with the views of a crop field and beautiful sunsets. Located right outside of Chestertown, the home puts shops, restaurants, and the local farmers market close by and is also walking distance to a view of the Chester River! An amazing opportunity to en

$478,000

2 beds2 baths1,904 sq ft

7982 Radcliffe Rd, Chestertown, MD 21620

Office space • Corner-lot • Nice-sized yard

(410) 810-0010

ABOUT THIS HOME
21620, MD Homes for Sale
Located in a beautiful waterfront community, this refreshed 5-bedroom, 2.5-bath home offers approximately 1,936 square feet of comfortable living space on approximately 0.38 acres. The property combines updated interiors, flexible living spaces, and the relaxed lifestyle of Maryland’s Eastern Shore. The home offers five generously sized bedrooms, providing comfortable space for family, guests, or work-from-home needs. The versatile fifth bedroom can function as a home office, guest room, flex space, or secondary suite, depending on your needs. The upgraded kitchen features bright white cabinetry, updated countertops and backsplash, stainless-steel Whirlpool appliances, and a KitchenAi

$445,000

5 beds2.5 baths1,936 sq ft

8630 Elm Rd, Chestertown, MD 21620

Upgraded kitchen • Updated interiors • Electric fireplace

(301) 355-6104

Property at 101 S College Ave, Chestertown, MD 21620, 2 beds, 1.5 baths

$369,000

2 beds1.5 baths1,036 sq ft

101 S College Ave, Chestertown, MD 21620

(410) 810-0010

Property at 115 Chester Arms Dr, Chestertown, MD 21620, 3 beds, 2 baths

$263,000

3 beds2 baths1,140 sq ft

115 Chester Arms Dr, Chestertown, MD 21620

(703) 378-8810

Property at 10540 Tonopah Rd, Chestertown, MD 21620, 3 beds, 2 baths

$279,000

3 beds2 baths1,404 sq ft

10540 Tonopah Rd, Chestertown, MD 21620

(410) 810-0010

Property at 240 Round Top Rd, Chestertown, MD 21620, 3 beds, 2 baths

$295,000

3 beds2 baths1,132 sq ft

240 Round Top Rd, Chestertown, MD 21620

(410) 827-4663

Property at 8999 Orchard Dr, Chestertown, MD 21620, 5 beds, 3.5 baths

$824,900

5 beds3.5 baths4,353 sq ft

8999 Orchard Dr, Chestertown, MD 21620

(410) 778-0330

Property at 216 Birch Run Rd, Chestertown, MD 21620, 3 beds, 2.5 baths

$750,000

3 beds2.5 baths2,176 sq ft

216 Birch Run Rd, Chestertown, MD 21620

(410) 673-3344

Property at 124 Wilton Rd, Chestertown, MD 21620, 3 beds, 1 bath

$299,900

3 beds1 bath1,056 sq ft

124 Wilton Rd, Chestertown, MD 21620

(410) 810-0010

Property at 533 Round Top Rd, Chestertown, MD 21620, 4 beds, 1.5 baths

$225,000

4 beds1.5 baths1,800 sq ft

533 Round Top Rd, Chestertown, MD 21620

(833) 335-7433

Property at 104 Church Aly, Chestertown, MD 21620, 2 beds, 1.5 baths

$440,000

2 beds1.5 baths1,058 sq ft

104 Church Aly, Chestertown, MD 21620

(410) 778-0330

Property at 109 Parma Rd, Chestertown, MD 21620, 3 beds, 2 baths

$315,000

3 beds2 baths1,288 sq ft

109 Parma Rd, Chestertown, MD 21620

(410) 778-0330

Property at 7828 Country Club Ln, Chestertown, MD 21620, 3 beds, 2.5 baths

$799,000

3 beds2.5 baths2,857 sq ft

7828 Country Club Ln, Chestertown, MD 21620

(410) 778-3779

Property at 106 Harlan Loop, Chestertown, MD 21620, 4 beds, 3 baths

$425,000

4 beds3 baths2,490 sq ft

106 Harlan Loop, Chestertown, MD 21620

Property at 129 Trafford Dr, Chestertown, MD 21620, 3 beds, 2.5 baths

$480,000

3 beds2.5 baths3,176 sq ft

129 Trafford Dr, Chestertown, MD 21620

(302) 422-2619

Property at 25750 Collins Ave, Chestertown, MD 21620, 3 beds, 2 baths

$448,000

3 beds2 baths3,262 sq ft

25750 Collins Ave, Chestertown, MD 21620

(410) 810-0010

Property at 7680 Country Club Ln, Chestertown, MD 21620, 5 beds, 4 baths

$885,000

5 beds4 baths2,639 sq ft

7680 Country Club Ln, Chestertown, MD 21620

(410) 275-2118

Property at 200 Manor Ave, Chestertown, MD 21620, 4 beds, 2 baths

$325,000

4 beds2 baths2,198 sq ft

200 Manor Ave, Chestertown, MD 21620

(410) 673-3344

Property at 1010 Twin Ct, Chestertown, MD 21620, 4 beds, 2 baths

$375,000

4 beds2 baths1,476 sq ft

1010 Twin Ct, Chestertown, MD 21620

(410) 827-6163

Property at 234 N College Ave, Chestertown, MD 21620, 2 beds, 1 bath

$85,000

2 beds1 bath1,296 sq ft

234 N College Ave, Chestertown, MD 21620

(410) 823-0033

Property at 21324 Persimmon Dr, Chestertown, MD 21620, 2 beds, 1 bath

$189,000

2 beds1 bath1,232 sq ft

21324 Persimmon Dr, Chestertown, MD 21620

(410) 822-6665

Property at 8796 Maryland Pkwy, Chestertown, MD 21620, 9 beds, 6.5 baths

$1,495,000

9 beds6.5 baths4,776 sq ft

8796 Maryland Pkwy, Chestertown, MD 21620

(410) 778-0330

Property at 115 Metcalf Rd, Chestertown, MD 21620, 3 beds, 1.5 baths

$259,900

3 beds1.5 baths1,280 sq ft

115 Metcalf Rd, Chestertown, MD 21620

(855) 450-0442

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 22470 Fairgale Farm Ln, Chestertown, MD 21620, 4 beds, 5 baths

$1,450,000

4 beds5 baths4,257 sq ft

22470 Fairgale Farm Ln, Chestertown, MD 21620

(410) 275-2118

Property at 10781 Fermoy Rd, Chestertown, MD 21620, 4 beds, 2.5 baths

$429,900

4 beds2.5 baths2,160 sq ft

10781 Fermoy Rd, Chestertown, MD 21620

(855) 450-0442

Property at 213 Byford Dr, Chestertown, MD 21620, 4 beds, 2 baths

$380,000

4 beds2 baths1,277 sq ft

213 Byford Dr, Chestertown, MD 21620

(410) 810-0010

Property at 106 Queen St S, Chestertown, MD 21620, 3 beds, 3.5 baths

$829,000

3 beds3.5 baths2,472 sq ft

106 Queen St S, Chestertown, MD 21620

(443) 215-4663

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 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 409 Calvert St, Chestertown, MD 21620, 3 beds, 1.5 baths

$145,000

3 beds1.5 baths1,192 sq ft

409 Calvert St, Chestertown, MD 21620

(443) 215-4663

Property at 6746 Quaker Neck Rd, Chestertown, MD 21620, 5 beds, 2.5 baths

$349,000

5 beds2.5 baths3,371 sq ft

6746 Quaker Neck Rd, Chestertown, MD 21620

(410) 810-0010

Property at 117 Water St N Unit 1A, 1B, 2A, & 2B, Chestertown, MD 21620, 7 beds, 5 baths

$1,500,000

7 beds5 baths5,400 sq ft

117 Water St N Unit 1A, 1B, 2A, & 2B, Chestertown, MD 21620

(410) 673-3344

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 204 Double Creek Rd, Chestertown, MD 21620, 3 beds, 2.5 baths

$545,000

3 beds2.5 baths2,927 sq ft

204 Double Creek Rd, Chestertown, MD 21620

(410) 810-0010

Property at 8706 Elm Rd, Chestertown, MD 21620, 3 beds, 2 baths

$320,000

3 beds2 baths1,232 sq ft

8706 Elm Rd, Chestertown, MD 21620

(410) 810-0010

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 105 High St, Chestertown, MD 21620, 5 beds, 4.5 baths

$1,245,500

5 beds4.5 baths3,243 sq ft

105 High St, Chestertown, MD 21620

(410) 778-0330

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Average home prices near 21620, MD

Cities

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21620, MD real estate trends

All Home Types trends in 21620, MD

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$362,418

-3.4% YoY | Jun 2026

1 year
3 year
5 year

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

Location

Data

Jun 2026

Growth

% YoY

21620, MD

$362,418

-3.4%

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