New Listings for Sale in 21620, MD

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ABOUT THIS HOME
New Listing for sale in 21620, MD:
Welcome to Mile Tree Village, one of Chestertown’s most desirable neighborhoods, where this beautifully maintained 1994 brick rambler sits proudly at the end of a quiet cul-de-sac on more than a half acre lot. Offering 3 bedrooms, 2.5 baths, and over 2,100 square feet of thoughtfully designed main level living, this home combines timeless Eastern Shore appeal in an absolutely turnkey package. * A freshly sealed asphalt drive curves to a welcoming front entry, where a classic brick facade sets a warm, distinctive tone. A two-car attached garage provides direct entry and everyday convenience. * Inside, the open kitchen—complete with breakfast area—flows seamlessly into a s

$750,000

3 beds2.5 baths2,176 sq ft

216 Birch Run Rd, Chestertown, MD 21620

Quiet cul-de-sac • Brick facade • Half acre lot

(410) 673-3344

ABOUT THIS HOME
New Listing for sale in 21620, MD:
A perfect pied-a-terre or full time residence, this adorable historic home is just steps from the farmers market, shops, restaurants, theater, art galleries and the Chester River. Zoned residential or business. Completely updated in 2021. Metal roof. Loaded with character and charm.

$440,000

2 beds1.5 baths1,058 sq ft

104 Church Aly, Chestertown, MD 21620

Zoned business • Zoned residential • Farmers market

(410) 778-0330

COMING SOON

ABOUT THIS HOME
New Listing for sale in 21620, MD:
Interior Pictures Coming Soon! Fantastic opportunity to own a beautifully maintained 3-bedroom, 2.5-bath townhome in The Village of Chestertown, offered at a price that is - below market value! Only 3 years young and in excellent condition, this home offers the benefits of newer construction. Conveniently located with an easy commute to Route 301 and just around the corner from the newer YMCA. Enjoy all that Chestertown has to offer, from its charming small-town atmosphere and wonderful restaurants to artistic venues, community events, and Washington College. A must-see for buyers looking for a newer home, excellent condition, and exceptional value in a great location!

$259,900

3 beds2.5 baths1,420 sq ft

249 Island Lark Way, Chestertown, MD 21620

$70 HOA • Built 2023

(410) 778-3779

COMING SOON

ABOUT THIS HOME
New Listing for sale in 21620, MD:
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

NEW 21 HRS AGO

ABOUT THIS HOME
New Listing for sale in 21620, MD:
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

Property at 117 N Water St Unit 3B, Chestertown, MD 21620, 1 bed, 1 bath

$295,000

1 bed1 bath— sq ft

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

(410) 778-0330

Property at 7982 Radcliffe Rd, Chestertown, MD 21620, 2 beds, 2 baths

$478,000

2 beds2 baths1,904 sq ft

7982 Radcliffe Rd, Chestertown, MD 21620

(410) 810-0010

Property at 8630 Elm Rd, Chestertown, MD 21620, 5 beds, 2.5 baths

$445,000

5 beds2.5 baths1,936 sq ft

8630 Elm Rd, Chestertown, MD 21620

(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 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 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 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 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 Cannon St, Chestertown, MD 21620

$450,000

Land0.29 acre (lot)

Cannon St, Chestertown, MD 21620

(301) 970-2447

Property at Sandpiper Rd, Chestertown, MD 21620

$4,500

Land0.52 acre (lot)

Sandpiper Rd, Chestertown, MD 21620

(443) 215-4663

Property at 620 Cannon St, Chestertown, MD 21620

$99,999

Land3,096 sq ft (lot)

620 Cannon St, Chestertown, MD 21620

(301) 970-2447

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OPEN SAT, 10AM TO 12PM

ABOUT THIS HOME
New Listing for sale in 21620, MD:
🏡 OPEN HOUSE THIS SATURDAY, August 22nd from 10:00 AM – 12:00 PM, come tour this beautiful property!. .. .ABSOLUTELY A MUST-SEE! This stunning custom built home shows like a model and truly checks all the boxes! Showcasing outstanding craftsmanship, thoughtful design, and high-end finishes throughout, every detail has been carefully curated to create a home that is both elegant and inviting. It offers exceptional space, and the feel of a brand new home, just 2 years young and located in a newly developed community. Spanning over 2,400+ square feet on a 1-acre lot, this impressive home features 4 bedrooms and 3 full bathrooms with a crafted open layout. Step through the beautiful foye

$695,000

4 beds3 baths2,456 sq ft

458 Eagle Manor Dr, Church Hill, MD 21623

Quartz countertops • Propane cooktop • Large island

(410) 827-4663

ABOUT THIS HOME
New Listing for sale in 21620, MD:
Situated on . 97± acres in Worton, this versatile property offers plenty of space and possibilities with two utility buildings, public water, and public sewer. The main home features an open floor plan highlighted by a custom wooden kitchen bar that provides generous counter space and creates a natural gathering spot for entertaining. A separate shop building adds even more functionality and is equipped with an oil furnace and air conditioning, making it comfortable for year-round use. Whether you’re looking for workshop space, storage, a hobby area, or room for your next project, this property offers flexibility that's hard to find. Conveniently located in Worton with nearly a

$349,000

2 beds1.5 baths1,089 sq ft

10725 Worton Rd, Worton, MD 21678

Utility buildings • Public sewer • Oil furnace

(410) 810-3900

COMING SOON

ABOUT THIS HOME
New Listing for sale in 21620, MD:
Welcome to this beautifully maintained `three-bedroom, two-bathroom home, built in 2021 and offering a like-new feeling. The thoughtfully designed interior features modern finishes throughout, including granite countertops, stainless steel appliances, tankless water heater, and the exterior features hardi-plank siding. Quality construction inside and out. This home is move-in ready and offers a perfect blend of modern comfort and small town living.

$435,000

3 beds2 baths1,568 sq ft

414 Church St, Sudlersville, MD 21668

Hardi-plank siding • Granite countertops • 0.47 acre lot

(410) 543-4545

COMING SOON

ABOUT THIS HOME
New Listing for sale in 21620, MD:
COMING SOON - Rare opportunity to own TWO homes, an impressive 4,800+ sq. ft. shop, additional pole barn, and 25+ acres—all just minutes from Route 301! The heated and insulated 120' x 40' shop is fully equipped for a mechanic, contractor, trucking operation, or other business use. It features two separate bays with an office, break room, and bathroom between them, plus additional loft storage. A 30' x 50' pole barn with electric and water offers even more possibilities and is ideal for horses, equipment, or agricultural use. Main Home – 2321 Millington Rd: Approximately 1,527 sq. ft. with 3 bedrooms and 2 baths. Features include hardwood floors, a spacious living area open to t

$1,200,000

6 beds4.5 baths2,708 sq ft

2321 Millington, Millington, MD 21651

Pole barn • 25 acres • Two separate bays

(410) 648-6844

COMING SOON

ABOUT THIS HOME
New Listing for sale in 21620, MD:
COMING SOON! This exceptional 4-bedroom, 2.5-bath custom home offers a level of thoughtful design, upgrades, and attention to detail that truly sets it apart. Located on a desirable cul-de-sac and backing to woods and community open space, this home combines an impressive interior with privacy and outstanding outdoor living. From the moment you arrive, the custom character is evident in the beautiful curb appeal, stone-faced foundation, welcoming front porch, and handsome wood accents. Inside, the showpiece kitchen is designed for both everyday living and entertaining, featuring high-end appliances, upgraded finishes, and a huge center island offering abundant prep space, seating, and a nat

$699,500

4 beds2.5 baths2,378 sq ft

478 Eagle Manor Dr, Church Hill, MD 21623

High-end appliances • Community open space • Backs to woods

(443) 988-0114

OPEN SAT, 10AM TO 12PM

ABOUT THIS HOME
New Listing for sale in 21620, MD:
New Home on a Full Acre in Desirable Condor Manor! For a limited time, the seller is offering $6000 seller contribution toward an interest rate buy-down, with an acceptable full-price offer, received before August 31, 2026. Welcome to this beautifully built, move-in ready home nestled on a spacious one-acre lot in Church Hill's sought-after Condor Manor community. Offering 2,016 square feet of thoughtfully designed living space, this two-story home features 4 bedrooms, 2.5 baths, and modern finishes throughout. Step inside to an open and inviting first floor showcasing durable luxury vinyl plank flooring, perfect for everyday living and entertaining. The stylish kitchen is the heart of the

$599,964

4 beds2.5 baths2,016 sq ft

334 Eagle Manor Dr, Church Hill, MD 21623

Spacious lot • Full acre • 42 inch cabinetry

(410) 643-2244

Property at 224 Main St, Church Hill, MD 21623, 4 beds, 2.5 baths

$579,999

4 beds2.5 baths2,668 sq ft

224 Main St, Church Hill, MD 21623

(443) 274-1900

Property at 224 Ewingtown Rd, Church Hill, MD 21623, 2 beds, 1.5 baths

$395,000

2 beds1.5 baths1,440 sq ft

224 Ewingtown Rd, Church Hill, MD 21623

(410) 810-0010

Property at 210 Groff Rd, Millington, MD 21651, 4 beds, 1 bath

$325,000

4 beds1 bath1,128 sq ft

210 Groff Rd, Millington, MD 21651

(410) 398-9200

Property at 155 Granard Ave, Centreville, MD 21617, 4 beds, 2 baths

$499,000

4 beds2 baths2,182 sq ft

155 Granard Ave, Centreville, MD 21617

(443) 274-1900

Property at 11035 Bottom Rd, Worton, MD 21678, 3 beds, 2 baths

$310,000

3 beds2 baths1,300 sq ft

11035 Bottom Rd, Worton, MD 21678

(410) 972-4000

Property at 405 Rings End Rd, Millington, MD 21651, 3 beds, 2 baths

$419,000

3 beds2 baths1,056 sq ft

405 Rings End Rd, Millington, MD 21651

(217) 285-9000

Property at 25133 Smithville Rd, Worton, MD 21678, 4 beds, 3 baths

$359,997

4 beds3 baths2,208 sq ft

25133 Smithville Rd, Worton, MD 21678

(443) 320-1344

Property at 120 Meadowcroft Dr, Centreville, MD 21617, 4 beds, 2.5 baths

$559,999

4 beds2.5 baths3,183 sq ft

120 Meadowcroft Dr, Centreville, MD 21617

(443) 274-1900

Property at 12118 Still Pond Creek Rd, Worton, MD 21678, 4 beds, 2.5 baths

$585,000

4 beds2.5 baths2,322 sq ft

12118 Still Pond Creek Rd, Worton, MD 21678

(302) 239-3000

Property at 5862 N Main St, Rock Hall, MD 21661, 3 beds, 2 baths

$349,000

3 beds2 baths1,381 sq ft

5862 N Main St, Rock Hall, MD 21661

(877) 366-2213

Property at 11960 Flour Mill St, Kennedyville, MD 21645, 7 beds, 5 baths

$515,000

7 beds5 baths3,836 sq ft

11960 Flour Mill St, Kennedyville, MD 21645

(410) 778-0330

Property at 116 Reeand Ln, Church Hill, MD 21623, 3 beds, 2.5 baths

$415,000

3 beds2.5 baths1,807 sq ft

116 Reeand Ln, Church Hill, MD 21623

(410) 778-0330

Property at Parcel 38 Goldsboro Rd, Barclay, MD 21607

$80,000

Land5.00 acres (lot)

Parcel 38 Goldsboro Rd, Barclay, MD 21607

(443) 988-0483

Property at Parcel 73 Barclay Rd, Barclay, MD 21607

$85,000

Land7.50 acres (lot)

Parcel 73 Barclay Rd, Barclay, MD 21607

(443) 988-0483

New Listings for Sale in 21620

There are currently 20 new listings for sale in 21620 at a median listing price of $375K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 21620 stay on the market for 73 days and receive 1 offers. This map is refreshed with the newest listings in 21620 every 15 minutes.

In the past month, 15 homes have been sold in 21620. In addition to houses in 21620, there was also 1 condo, 18 townhouses, and 1 multi-family unit for sale in 21620 last month. Find your dream home in 21620 using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in 21620 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 21620. If you're looking to sell your home in the 21620 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 21620 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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