4 Bedroom homes for sale & real estate in 21620, MD

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ABOUT THIS HOME
4 Bedroom Homes 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

COMING SOON

ABOUT THIS HOME
4 Bedroom Homes for Sale in 21620, MD
Introducing this spacious 4-bedroom, 1.5-bath ranch on an extra-wide fenced lot in the Chester Harbor community, just minutes from historic Chestertown. Offering comfortable single-level living, the home features a large family room, an expansive kitchen with abundant cabinet and counter space, and a functional floor plan ready for your personal updates and vision. Whether you’re looking for your next home, an investment opportunity, or a property to renovate and build equity, this home offers exceptional potential. The generous layout includes four bedrooms, one full bath, one half bath, and flexible space for guests, a home office, or hobbies. Outside, the oversized iron-fenced yard

$225,000

4 beds1.5 baths1,800 sq ft

533 Round Top Rd, Chestertown, MD 21620

Community boat ramp • Large family room • Expansive kitchen

(833) 335-7433

FOR SALE BY OWNER

ABOUT THIS HOME
4 Bedroom Homes for Sale in 21620, MD
2-Story with a full basement with a high seiling Brick on front siding and vinyl on rest of house located in Coventry Farms in Chestertown, Md. 21620 Built in 2009 4 bedrooms 2.5 bathroom 3165sq. ft. in living space full garage, Central air with heat pump On 2.8 acre lot Town Water and Sewage tax: 5305.00 per year

$425,000

4 beds3 baths2,490 sq ft

106 Harlan Loop, Chestertown, MD 21620

2.8 acre lot • Full basement • Built 2009

ABOUT THIS HOME
4 Bedroom Homes for Sale in 21620, MD
Adorable 4 bedroom 2 bathroom Cape Cod in the quiet Crestview neighborhood in Chestertown close to Restaurants, Shopping, the brand new YMCA and the Historic Downtown. Eat in kitchen with back deck overlooking a beautiful yard that backs up to farm land that is preserved forever. Freshly painted with new carpet! Washer & dryer in unit. Extra storage in knee walls upstairs. In Chestertown but outside the town limits so no town tax or water/sewer bill! Come make this home yours today, immediate occupancy.

$375,000

4 beds2 baths1,476 sq ft

1010 Twin Ct, Chestertown, MD 21620

Extra storage • Farm land preserved • Back deck

(410) 827-6163

ABOUT THIS HOME
4 Bedroom Homes for Sale in 21620, MD
A rare opportunity to own a classic two-story split-level home in Chestertown — set on a large, shaded corner lot just a few miles to Downtown Chestertown, Washington College, the weekly farmers market, the town's annual festivals, and only steps to locally loved restaurants and everyday conveniences. This is the kind of home that simply isn't built anymore: classic lines, original details, and the quiet character that comes from decades of careful ownership. Step inside and the home tells its story with original trim, classic proportions and timeless architectural touches. The two-story split-level floor plan offers a thoughtful separation of living and sleeping spaces, with a sun-fi

$325,000

4 beds2 baths2,198 sq ft

200 Manor Ave, Chestertown, MD 21620

Modern mechanicals • Sun filled sunroom • New hvac system

(410) 673-3344

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 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 8620 Park Dr, Chestertown, MD 21620, 4 beds, 2.5 baths

$489,900

4 beds2.5 baths2,524 sq ft

8620 Park Dr, Chestertown, MD 21620

(410) 810-0010

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

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OPEN TODAY, 10AM TO 12PMVIDEO TOUR

ABOUT THIS HOME
4 Bedroom Homes 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

COMING SOON

ABOUT THIS HOME
4 Bedroom Homes 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 TODAY, 10AM TO 12PM

ABOUT THIS HOME
4 Bedroom Homes 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

COMING SOON

ABOUT THIS HOME
4 Bedroom Homes for Sale in 21620, MD
Opportunity is knocking!!! This property has been FULLY renovated and ready for you! Single Family Home, Investment Property, YOUR CHOICE!!!! Hits the market 8/21!

$579,999

4 beds2.5 baths2,668 sq ft

224 Main St, Church Hill, MD 21623

0.46 acre lot • Built 1893 • Listed 5 days

(443) 274-1900

ABOUT THIS HOME
4 Bedroom Homes for Sale in 21620, MD
WOW! Check out this AMAZING remodel! This ranch home went from zero to hero in no time! It's a 4-bedroom, 1 bath home in Millington, MD with easy access to Rte. 301 for any daily commute! Home sits on a half-acre of property with a huge side yard for any new buildings or storage needs. Updates include a completely new kitchen with stainless steel appliances and quartz countertops, new wood style LPV flooring, new HVAC, metal roof, front porch, back deck, new ceiling fans, recessed lights, newer septic, newer well pump and newer bladder tank. This place shines beautifully! Make your appointment today and see all that this home has to offer. Call Lori for your private tour! Showings start Fr

$299,900

4 beds1 bath1,128 sq ft

210 Groff Rd, Millington, MD 21651

Quartz countertops • Metal roof • Front porch

(410) 398-9200

ABOUT THIS HOME
4 Bedroom Homes for Sale in 21620, MD
Welcome to 25133 Smithville Rd. ! This spacious 4-bedroom, 3-bath traditional Colonial offers comfortable living with plenty of room to spread out. The main level features a desirable primary suite with a private full bath, along with an inviting eat-in kitchen and formal dining room perfect for everyday living and entertaining. Step outside to enjoy the spacious, level backyard with fencing for added privacy. There is plenty of room for entertaining, family gatherings, kids, pets, outdoor activities, and more—all while enjoying your own private outdoor space. With its spacious layout, convenient main-level primary suite, and private backyard, this home offers a wonderful opportunity

$359,997

4 beds3 baths2,208 sq ft

25133 Smithville Rd, Worton, MD 21678

Formal dining room • Fencing for privacy • Primary suite

(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 611 Clark Corners Rd, Centreville, MD 21617, 4 beds, 2.5 baths

$549,987

4 beds2.5 baths2,596 sq ft

611 Clark Corners Rd, Centreville, MD 21617

(443) 249-7653

Property at 21610 Hidden Creek Dr, Rock Hall, MD 21661, 4 beds, 3 baths

$699,000

4 beds3 baths2,185 sq ft

21610 Hidden Creek Dr, Rock Hall, MD 21661

(217) 285-9000

Property at 427 Brookfield Dr, Centreville, MD 21617, 4 beds, 2.5 baths

$509,900

4 beds2.5 baths2,512 sq ft

427 Brookfield Dr, Centreville, MD 21617

(410) 429-7425

Property at 913 Clark Corners Rd, Centreville, MD 21617, 4 beds, 2.5 baths

$609,900

4 beds2.5 baths2,752 sq ft

913 Clark Corners Rd, Centreville, MD 21617

(410) 643-5005

Property at 122 Lently Farm Ln, Centreville, MD 21617, 4 beds, 2.5 baths

$575,000

4 beds2.5 baths2,784 sq ft

122 Lently Farm Ln, Centreville, MD 21617

(410) 827-4663

Property at 24274 Waterview Dr, Worton, MD 21678, 4 beds, 3.5 baths

$765,000

4 beds3.5 baths3,006 sq ft

24274 Waterview Dr, Worton, MD 21678

(410) 778-0330

Property at 21173 and 21163 Chesapeake Ave, Rock Hall, MD 21661, 4 beds, 3.5 baths

$649,900

4 beds3.5 baths2,944 sq ft

21173 and 21163 Chesapeake Ave, Rock Hall, MD 21661

(410) 810-0010

Property at Price Station Rd, Centreville, MD 21617, 4 beds, 2 baths

$649,500

4 beds2 baths2,000 sq ft

Price Station Rd, Centreville, MD 21617

(443) 988-0114

Property at 21424 Catholic Ave, Rock Hall, MD 21661, 4 beds, 2 baths

$399,000

4 beds2 baths1,247 sq ft

21424 Catholic Ave, Rock Hall, MD 21661

(410) 275-2118

Property at 306 Old Line Dr, Centreville, MD 21617, 4 beds, 3 baths

$670,000

4 beds3 baths3,010 sq ft

306 Old Line Dr, Centreville, MD 21617

(301) 970-2447

Property at 20694 Mercer Ave, Rock Hall, MD 21661, 4 beds, 2 baths

$650,000

4 beds2 baths2,271 sq ft

20694 Mercer Ave, Rock Hall, MD 21661

(410) 275-2118

Property at 131 Fair Brook Way, Centreville, MD 21617, 4 beds, 3.5 baths

$585,000

4 beds3.5 baths3,508 sq ft

131 Fair Brook Way, Centreville, MD 21617

4 Bedroom Homes for Sale in 21620

There are currently 11 4 bedroom homes in 21620. 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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