Homes with Pools for Sale in 21620, MD

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COMING SOON

$315,000

3 beds2.5 baths1,468 sq ft

676 Deep Landing Rd, Chestertown, MD 21620

0.59 acre lot • Garage • Built 2014

(410) 778-3779

COMING SOON

ABOUT THIS HOME
Home with a Pool for sale in 21620, MD:
Rancher in Chester Harbor coming soon! Check back for more details and photos!

$319,900

3 beds2 baths1,232 sq ft

213 Central Dr, Chestertown, MD 21620

0.34 acre lot • 2 garage spots • Built 1984

(410) 778-0330

OPEN DEC 13, 11AM TO 1PM

ABOUT THIS HOME
Home with a Pool for sale in 21620, MD:
Live with ease in this beautifully updated and maintained one floor home in downtown Chestertown. The current owners put a large addition on the house that includes a family room with wood burning stove, sunroom, and primary suite with en suite bathroom and walk in closet. A large laundry room on the main floor and updated kitchen with tons of counter space were other valuable design updates. The basement provides ample partially finished storage space in a completely dry environment due to serious structural improvements, sump pump and french drain system. Bring your hobby down there or your trusty work bench. The roof, HVAC, and hot water heater are all less than 10 years old. The front y

$370,000

3 beds2 baths2,296 sq ft

204 Rolling Rd, Chestertown, MD 21620

0.34 acre lot • 3 parking spots • Built 1975

(410) 778-0330

OPEN SAT, 11AM TO 1PM

ABOUT THIS HOME
Home with a Pool for sale in 21620, MD:
Welcome to 121 Primrose Road, a spacious two-story residence offering 2,034 square feet on a . 345-acre lot. This well-built home delivers comfort, functionality, and potential in a peaceful setting just outside downtown Chestertown. Inside, you’ll find three bedrooms and two full baths upstairs plus a convenient half bath on the main level. The main floor features a bright living area, a classic dining space, and a large all-seasons room off the kitchen—perfect for gatherings or relaxing year-round. The full basement offers a blank slate, ready to finish as a recreation room, workshop, or extra storage. A brand-new septic system provides peace of mind, while the attached two-ca

$399,000

3 beds2.5 baths2,034 sq ft

121 Primrose Rd, Chestertown, MD 21620

0.34 acre lot • 2 garage spots • Built 1971

(410) 778-0330

ABOUT THIS HOME
Home with a Pool for sale in 21620, MD:
311 Devon Drive is located in Coventry Farms; and being located within the Chestertown town limits offers town utilities. The front entrance welcomes you with an open two-story foyer to the second-floor balcony. To the left of the front foyer is a den and to the right is a formal dining room. The foyer hall leads into a large open area that includes a large eat-in kitchen, sunroom and family room with a gas fireplace. The home's design features an abundance of natural light due to its 9-foot ceilings and full-height glass walls on the first floor's rear. The sunroom and first floor primary suite access onto the rear deck with the view and privacy of mature trees. There is a primary bedroom

$598,000

5 beds3.5 baths3,504 sq ft

311 Devon Dr, Chestertown, MD 21620

Large eat in kitchen • Gas fireplace • Natural light

(410) 810-0010

Property at 222 Mount Vernon Ave, Chestertown, MD 21620, 4 beds, 2 baths

$470,000

4 beds2 baths1,656 sq ft

222 Mount Vernon Ave, Chestertown, MD 21620

(410) 263-3400

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

$1,395,500

5 beds4.5 baths3,243 sq ft

105 High St, Chestertown, MD 21620

(410) 778-0330

Property at 611 Cannon St, Chestertown, MD 21620, 2 beds, 1.5 baths

$299,000

2 beds1.5 baths920 sq ft

611 Cannon St, Chestertown, MD 21620

(410) 810-3900

Property at 7521 Pine Ave, Chestertown, MD 21620, 3 beds, 1 bath

$265,000

3 beds1 bath1,040 sq ft

7521 Pine Ave, Chestertown, MD 21620

(443) 215-4663

Property at 304 Hadaway Dr, Chestertown, MD 21620, 4 beds, 2 baths

$399,000

4 beds2 baths1,325 sq ft

304 Hadaway Dr, Chestertown, MD 21620

(410) 823-0033

Property at 21111 Texas Ave, Chestertown, MD 21620, 3 beds, 2 baths

$370,000

3 beds2 baths1,680 sq ft

21111 Texas Ave, Chestertown, MD 21620

(410) 690-7356

Property at 216 Blakefield Dr, Chestertown, MD 21620, 4 beds, 3 baths

$579,000

4 beds3 baths2,400 sq ft

216 Blakefield Dr, Chestertown, MD 21620

(410) 476-2201

Property at 108 Flying Cloud Dr, Chestertown, MD 21620, 4 beds, 2.5 baths

$375,000

4 beds2.5 baths1,936 sq ft

108 Flying Cloud Dr, Chestertown, MD 21620

(410) 778-3779

Property at 10121 Fairlee Rd, Chestertown, MD 21620, 6 beds, 5 baths

$2,350,000

6 beds5 baths4,954 sq ft

10121 Fairlee Rd, Chestertown, MD 21620

(410) 778-0330

Property at 206 S Water St, Chestertown, MD 21620, 4 beds, 3.5 baths

$619,000

4 beds3.5 baths2,008 sq ft

206 S Water St, Chestertown, MD 21620

(301) 967-3344

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 100 Adela Way, Chestertown, MD 21620, 4 beds, 3.5 baths

$515,000

4 beds3.5 baths3,799 sq ft

100 Adela Way, Chestertown, MD 21620

(410) 266-0600

Property at 107 Malone Ave, Chestertown, MD 21620, 3 beds, 1 bath

$290,000

3 beds1 bath1,200 sq ft

107 Malone Ave, Chestertown, MD 21620

(866) 987-3937

Property at 7844 Chester Ct, Chestertown, MD 21620, 4 beds, 2.5 baths

$770,000

4 beds2.5 baths3,248 sq ft

7844 Chester Ct, Chestertown, MD 21620

(410) 810-0010

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

$499,900

4 beds2.5 baths2,524 sq ft

8620 Park Dr, Chestertown, MD 21620

(410) 810-0010

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 109 S College Ave, Chestertown, MD 21620, 3 beds, 2.5 baths

$449,900

3 beds2.5 baths1,216 sq ft

109 S College Ave, Chestertown, MD 21620

(410) 778-3779

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

$364,000

4 beds2 baths1,625 sq ft

8833 Georgetown Rd, Chestertown, MD 21620

(410) 778-0330

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

$2,500,000

5 beds4.5 baths4,305 sq ft

7989 Quaker Neck Rd, Chestertown, MD 21620

(410) 778-0330

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

$279,000

3 beds1 bath1,128 sq ft

134 Char Nor Manor Blvd, Chestertown, MD 21620

(410) 714-9166

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

$359,900

3 beds1 bath1,805 sq ft

23110 Old Fairlee Rd, Chestertown, MD 21620

(855) 450-0442

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

$344,900

3 beds2 baths1,392 sq ft

109 Wilton Rd, Chestertown, MD 21620

(443) 215-4663

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

$409,900

4 beds2.5 baths2,258 sq ft

165 Char Nor Manor Blvd, Chestertown, MD 21620

(443) 274-1900

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 100 Metcalf Rd, Chestertown, MD 21620, 3 beds, 2 baths

$245,000

3 beds2 baths1,140 sq ft

100 Metcalf Rd, Chestertown, MD 21620

(443) 829-5828

Property at 118 Little Harbor Way #202, Chestertown, MD 21620, 3 beds, 2 baths

$695,000

3 beds2 baths1,600 sq ft

118 Little Harbor Way #202, Chestertown, MD 21620

(410) 822-6665

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

$325,000

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

$539,999

2 beds2.5 baths2,100 sq ft

103 Landing Ln, Chestertown, MD 21620

(410) 778-0330

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

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

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Homes with Pools for Sale in 21620

There are currently 78 homes with pools for sale in 21620 at a median listing price of $415K. 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 64 days and receive 1 offers. This map is refreshed with the newest listings in 21620 every 15 minutes.

In the past month, 17 homes have been sold in 21620. In addition to houses in 21620, there was also 1 condo, 13 townhouses, and 2 multi-family units 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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