Homes with Parking for Sale in Chestertown, MD

29 homes

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NEW 23 HRS AGO

ABOUT THIS HOME
Home with Parking for sale in Chestertown, 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

OPEN DEC 6, 11AM TO 1PM

ABOUT THIS HOME
Home with Parking for sale in Chestertown, 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

NEW CONSTRUCTION

ABOUT THIS HOME
Home with Parking for sale in Chestertown, MD:
Discover the charm of this stunning new construction home in the desirable Blakefield community, completed in 2025. This beautifully designed Colonial-style residence boasts 4 spacious bedrooms and 3 full bathrooms, offering ample space for relaxation and entertainment. The kitchen is a chef's dream, featuring an island, eat-in space, and modern appliances including a built-in microwave, dishwasher, electric oven/range, and refrigerator. Enjoy cozy breakfasts in the bright breakfast area or host formal dinners in the separate dining room. The luxurious touches continue with walk-in closets, a convenient upper-floor laundry, and a family room that flows effortlessly from the kitchen and a se

$579,000

4 beds3 baths2,400 sq ft

216 Blakefield Dr, Chestertown, MD 21620

1 acre lot • 2 garage spots • Built 2025

(410) 476-2201

COMING SOON

ABOUT THIS HOME
Home with Parking for sale in Chestertown, MD:
COMING SOON in Tolchester Estates! Discover this well-maintained 2004 rancher located in a water-privileged community with access to the Chesapeake Bay. This charming home offers 3 bedrooms, 2 full baths, and beautiful wood floors throughout. The full unfinished basement is already roughed in for a future bathroom, giving you outstanding potential for added living space. A floored walk-up attic provides even more room for storage or expansion. Additional features include an attached garage and a screened porch perfect for enjoying the outdoors. Tolchester Estates offers the relaxed Eastern Shore lifestyle buyers love—quiet streets and access to the Bay. Showings begin soon—don&r

$370,000

3 beds2 baths1,680 sq ft

21111 Texas Ave, Chestertown, MD 21620

0.41 acre lot • $8 HOA • 2 garage spots

(410) 690-7356

COMING SOON

ABOUT THIS HOME
Home with Parking for sale in Chestertown, MD:
The one you’ve been waiting for! This 3-bedroom, 1-bath rancher in Quaker Estates offers convenient living just minutes from downtown Chestertown. Features include an oversized pole building with cement floors and electric, plus a long blacktop driveway for plenty of parking. This home is move-in ready, with room for a buyer to add their own personal touches. It has been lovingly maintained with a newer roof, central heat/air, and water softener. Competitively priced and full of potential! More pics will be posted by Dec 4th!

$265,000

3 beds1 bath1,040 sq ft

7521 Pine Ave, Chestertown, MD 21620

0.56 acre lot • 2 garage spots • Car-dependent

(443) 215-4663

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 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 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 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 101 Birch Run Rd, Chestertown, MD 21620, 3 beds, 2 baths

$499,999

3 beds2 baths1,961 sq ft

101 Birch Run Rd, Chestertown, MD 21620

(410) 287-3629

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 110 Tuxedo Rd, Chestertown, MD 21620, 3 beds, 2.5 baths

$269,000

3 beds2.5 baths1,664 sq ft

110 Tuxedo Rd, Chestertown, MD 21620

(410) 823-0033

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

$429,999

4 beds2.5 baths2,258 sq ft

165 Char Nor Manor Blvd, Chestertown, MD 21620

(443) 274-1900

Property at 116 Harlan Loop, Chestertown, MD 21620, 5 beds, 3.5 baths

$519,000

5 beds3.5 baths4,067 sq ft

116 Harlan Loop, Chestertown, MD 21620

(301) 850-0255

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 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 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 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 119 Darden Rd, Chestertown, MD 21620, 3 beds, 2 baths

$315,000

3 beds2 baths1,424 sq ft

119 Darden Rd, Chestertown, MD 21620

(410) 220-5745

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 141 Prospect St, Chestertown, MD 21620, 4 beds, 1.5 baths

$167,000

4 beds1.5 baths1,156 sq ft

141 Prospect St, Chestertown, MD 21620

(410) 778-3779

Property at 515 N Kent St, Chestertown, MD 21620, 4 beds, 2 baths

$499,900

4 beds2 baths2,220 sq ft

515 N Kent St, Chestertown, MD 21620

(410) 778-3779

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

$559,000

2 beds2.5 baths2,100 sq ft

103 Landing Ln, Chestertown, MD 21620

(410) 778-0330

Property at 201 Birch Run Rd, Chestertown, MD 21620, 3 beds, 2 baths

$470,000

3 beds2 baths1,588 sq ft

201 Birch Run Rd, Chestertown, MD 21620

(410) 778-0330

Property at 11040 Kylie Ln, Chestertown, MD 21620, 4 beds, 3.5 baths

$649,000

4 beds3.5 baths3,684 sq ft

11040 Kylie Ln, Chestertown, MD 21620

(410) 778-0330

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Homes with Parking for Sale in Chestertown

There are currently 29 homes with parking homes for sale in Chestertown at a median listing price of $450K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Chestertown stay on the market for 70 days and receive 1 offers. This map is refreshed with the newest listings in Chestertown every 15 minutes.

In the past month, 4 homes have been sold in Chestertown. In addition to houses in Chestertown, there were also 3 condos, 9 townhouses, and 2 multi-family units for sale in Chestertown last month. Find your dream home in Chestertown 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 Chestertown are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Chestertown. Our Chestertown real estate stats and trends will give you more information about home buying and selling trends in Chestertown. If you're looking to sell your home in the Chestertown area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Chestertown with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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