Homes with Basements for Sale in Kent County, MD

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ABOUT THIS HOME
Home with Basement for sale in Kent County, 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

ABOUT THIS HOME
Home with Basement for sale in Kent County, 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

ABOUT THIS HOME
Home with Basement for sale in Kent County, MD:
Just off Route 301 for commuters, but located in the country with privacy, space for animals, hobbies, and entertaining. Large detached garage with storage space above, full unfinished basement, fenced pasture area, and inground pool. So much potential here, come with vision and make it your own!

$429,000

4 beds2 baths1,794 sq ft

32287 Quinn Rd, Massey, MD 21650

1.64 acre lot • 4 garage spots • Pool

(410) 648-6844

ABOUT THIS HOME
Home with Basement for sale in Kent County, MD:
Tucked away along the quiet shores of Still Pond Creek, this cedar cabin offers a rare blend of privacy, comfort, and natural beauty. Surrounded by mature woods and set on a peaceful stretch of waterfront, this 1,944 square foot home features 3 bedrooms, 2 bathrooms, a spacious screened-in porch perfect for crab feasts, a private beach and pier with 2'+ MLW improved with bilk head installed by Army Corps. Whether you’re seeking a weekend retreat or a year-round escape, this property captures the essence of Eastern Shore living—simple, timeless, and immersed in nature where mind, body, and soul find balance.

$1,150,000

3 beds2 baths1,944 sq ft

12400 Woods Rd, Worton, MD 21678

5.08 acre lot • Built 1985 • Listed 10 days

(410) 778-3779

OPEN DEC 6, 12PM TO 2PM

ABOUT THIS HOME
Home with Basement for sale in Kent County, MD:
This masterpiece is finally complete. Rebuilt in 1863, the Tilley Residence showcases classic Second Empire style on one of Chestertown’s most prominent corners, neighboring Widehall and the Custom House. Expertly restored in 2024–2025 by one of Kent County’s premier builders, the home offers new HVAC, electrical, plumbing, roofing, flooring, and a refreshed open layout. Custom kitchen and baths balance modern comfort with timeless character. A grand three-story staircase and arched entryways welcome you inside. The front porch overlooks town and offers water views. The primary suite includes a fireplace, walk-in closet, and a tiled shower room with views from two sides. T

$1,395,500

5 beds4.5 baths3,243 sq ft

105 High St, Chestertown, MD 21620

Fenced in rear yard • Arched entryways • Detached garage

(410) 778-0330

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 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 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 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 13983 Turners Point Rd, Kennedyville, MD 21645, 2 beds, 2.5 baths

$625,000

2 beds2.5 baths4,054 sq ft

13983 Turners Point Rd, Kennedyville, MD 21645

(410) 275-2118

Property at 10 Ericsson Ave #31, Betterton, MD 21610, 2 beds, 2 baths

$329,500

2 beds2 baths1,620 sq ft

10 Ericsson Ave #31, Betterton, MD 21610

(410) 643-2244

Property at 25209 Wymont Park Rd, Worton, MD 21678, 3 beds, 3 baths

$1,150,000

3 beds3 baths2,874 sq ft

25209 Wymont Park Rd, Worton, MD 21678

(410) 810-0010

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 25135 Smithville Rd, Worton, MD 21678, 3 beds, 1 bath

$294,000

3 beds1 bath960 sq ft

25135 Smithville Rd, Worton, MD 21678

(410) 740-1200

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 14 Third Ave, Betterton, MD 21610, 3 beds, 3 baths

$235,000

3 beds3 baths2,050 sq ft

14 Third Ave, Betterton, MD 21610

(410) 778-0330

Property at 14540 Stirrup Ln, Galena, MD 21635, 4 beds, 3 baths

$819,000

4 beds3 baths3,388 sq ft

14540 Stirrup Ln, Galena, MD 21635

(717) 553-2500

Property at 31569 Jim Davis, Galena, MD 21635, 5 beds, 2.5 baths

$519,999

5 beds2.5 baths2,660 sq ft

31569 Jim Davis, Galena, MD 21635

(410) 287-3629

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 5135 Crosby Rd, Rock Hall, MD 21661, 6 beds, 4.5 baths

$5,900,000

6 beds4.5 baths4,214 sq ft

5135 Crosby Rd, Rock Hall, MD 21661

(410) 673-3344

Property at 21305 Haven Rd, Rock Hall, MD 21661, 4 beds, 2 baths

$350,000

4 beds2 baths1,499 sq ft

21305 Haven Rd, Rock Hall, MD 21661

(302) 426-2211

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

Property at 26670-26680 Maple Ave, Still Pond, MD 21667, 3 beds, 2 baths

$230,000

3 beds2 baths2,024 sq ft

26670-26680 Maple Ave, Still Pond, MD 21667

(410) 810-0010

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Homes with Basements for Sale in Kent County

There are currently 23 homes with basements for sale in Kent County at a median listing price of $397K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Kent County stay on the market for 56 days and receive 1 offers. This map is refreshed with the newest listings in Kent County every 15 minutes.

In the past month, 25 homes have been sold in Kent County. In addition to houses in Kent County, there were also 4 condos, 18 townhouses, and 3 multi-family units for sale in Kent County last month. Find your dream home in Kent County 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 Kent County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Kent County. If you're looking to sell your home in the Kent County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Kent County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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