Kingstown, MD homes for sale & real estate

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ABOUT THIS HOME
Kingstown, MD Homes for Sale
Fully remodeled by reputable licensed contractor and subcontractors, 104 Iris has had a glow-up and is ready for showing! The clean lines of the new quartz countertops, the weight of soft golden Amerock hardware, Moen fixtures, Wolf two-tone shaker style cabinetry and well-appointed subway tile set the stage in the beautiful new Kitchen and bathrooms. Where a modern feel is met with the softness and simplicity of Neutrals as you move throughout the rooms that offer a timeless yet 2026 vibe! High-quality, low-maintenance LVP flooring has been installed in all high-traffic areas, along with carpet to quiet the bedroom spaces. Many new energy-saving features include architectural shingles, R3

$379,000

3 beds2 baths1,700 sq ft

104 Iris Rd, Chestertown, MD 21620

Soft golden hardware • Moen fixtures • Remodeled kitchen

(410) 810-0010

ABOUT THIS HOME
Kingstown, MD Homes for Sale
Great rancher in Chester Harbor on the Queen Anne's County side of Chestertown. Fresh paint and carpet throughout. Both bathrooms are completely remodeled. The kitchen could use updating, but the space is great and the appliances are in excellent condition. Plenty of room to add a kitchen island and still have space for a table. Nice 2 car detached "pole barn" style garage. Fenced back yard. This property has a lot to offer!

$314,900

3 beds2 baths1,232 sq ft

213 Central Dr, Chestertown, MD 21620

0.34 acre lot • 2 garage spots • Built 1984

(410) 778-0330

ABOUT THIS HOME
Kingstown, MD Homes for Sale
Motivated Sellers!!! 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, whi

$375,000

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
Kingstown, MD Homes for Sale
Welcome to 119 Darden Road, a lovely ranch-style home nestled in Chestertown, MD. This charming residence offers 3 cozy bedrooms and 2 bathrooms across 1,424 square feet of living space, perfect for comfortable living. The eat-in kitchen, complete with a handy stove, sets the stage for delightful meals and gatherings. Enjoy the warm ambiance of a fireplace in the spacious living room, enhanced by recessed lighting. Step outside to a large deck overlooking a 15,000 square foot lot, perfect for relaxation and entertainment. This home features a playground and tennis court access for leisurely afternoons. With an attached garage, air conditioning, and in-building laundry, convenience is at you

$315,000

3 beds2 baths1,424 sq ft

119 Darden Rd, Chestertown, MD 21620

Large deck • Playground access • Eat-in kitchen

(410) 220-5745

ABOUT THIS HOME
Kingstown, MD Homes for Sale
Three bedroom one-floor living on a spacious lot in Chester Harbor! Over half an acre of nicely shaded yard space, and a short distance to the public beach on Mill Creek. 3 bedrooms and 1.5 bathrooms, open living and dining space, large sunroom/ porch with wood-burning stove, and an additional wood stove in the living room. Outside there's a small storage shed and a larger workshop/shed next to the asphalt driveway. The sunroom leads to a deck overlooking the large yard. Great community with water access. Quick ten minutes into Chestertown, and less than an hour to Middletown DE or Annapolis.

$320,000

3 beds1.5 baths1,096 sq ft

222 Dutchess Rd, Chestertown, MD 21620

0.67 acre lot • 4 parking spots • Pool

(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

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NEW CONSTRUCTION

ABOUT THIS HOME
Kingstown, MD Homes for Sale
Brand new home in Historic Chestertown available for move-in Right Now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Additional highlights include exclusive financing opportunities with zero down payment loans, paid closing cost programs, and discounted interest rates—making it possible to own this home for less than area rents. Delivered at the asking price as shown in the photo

$264,900

3 beds1.5 baths1,280 sq ft

109 Metcalf Rd, Chestertown, MD 21620

Eat-in kitchen • Granite countertops • Spacious living room

(855) 450-0442

NEW CONSTRUCTION

ABOUT THIS HOME
Kingstown, MD Homes for Sale
* * To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath and large walk-in closet. There are two additional bedrooms that share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or pu

$765,900

3 beds2.5 baths1,964 sq ft

#37 Landing Ln, Chestertown, MD 21620

Spa-like bath • Primary suite • Gas fireplace

(410) 275-2118

NEW CONSTRUCTION

ABOUT THIS HOME
Kingstown, MD Homes for Sale
* * To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to a private second floor balcony. There are two additional bedrooms that share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep wat

$753,500

3 beds2.5 baths1,964 sq ft

#36 Landing Ln, Chestertown, MD 21620

In-ground pool • Gas fireplace • Gourmet kitchen

(410) 275-2118

NEW CONSTRUCTION

ABOUT THIS HOME
Kingstown, MD Homes for Sale
* * To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to a private balcony. There are two additional bedrooms that share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slip

$786,900

3 beds2.5 baths1,964 sq ft

#35 Landing Ln, Chestertown, MD 21620

Second-floor laundry • Private balcony • Gas fireplace

(410) 275-2118

NEW CONSTRUCTION

ABOUT THIS HOME
Kingstown, MD Homes for Sale
* * To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space for guests. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and sliding doors to the second floor balcony. There are two additional bedrooms, each with their own full bathroom. the upstairs is complemented by a convenient second-floor laundry. This home is design

$813,900

3 beds3.5 baths2,192 sq ft

104 Landing Ln, Chestertown, MD 21620

Spa-like bath • Second-floor laundry • Private study

(410) 275-2118

NEW CONSTRUCTION

ABOUT THIS HOME
Kingstown, MD Homes for Sale
* * To be built! Welcome to this beautifully designed 2,784 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 4 bedrooms and 3.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. There is a first floor primary bedroom for one-floor living options. Upstairs, the second primary suite features a spa-like bath, large walk-in closet, and access to the private balcony. Two additional bedrooms share a full bathroom. Catch a glimpse of the Chester River from the front porch or upper covered balcony, the perfect place to enjoy morning co

$1,099,900

4 beds3.5 baths2,784 sq ft

#25 Landing Ln, Chestertown, MD 21620

Spa-like bath • Second primary suite • Gourmet kitchen

(410) 275-2118

Property at 102 Little Harbor Way, Chestertown, MD 21620, 3 beds, 2.5 baths

$839,500

3 beds2.5 baths1,964 sq ft

102 Little Harbor Way, Chestertown, MD 21620

(410) 275-2118

Property at 204 Rolling Rd, Chestertown, MD 21620, 3 beds, 2 baths

$370,000

3 beds2 baths2,296 sq ft

204 Rolling Rd, Chestertown, MD 21620

(410) 778-0330

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

$469,000

4 beds2 baths1,656 sq ft

222 Mount Vernon Ave, Chestertown, MD 21620

(410) 263-3400

Property at 228 S Water St, Chestertown, MD 21620, 3 beds, 3.5 baths

$878,000

3 beds3.5 baths2,310 sq ft

228 S Water St, Chestertown, MD 21620

(410) 275-2118

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 423 Calvert St, Chestertown, MD 21620, 3 beds, 1.5 baths

$135,000

3 beds1.5 baths1,136 sq ft

423 Calvert St, Chestertown, MD 21620

Property at 103 Metcalf Rd, Chestertown, MD 21620, 3 beds, 1.5 baths

$259,900

3 beds1.5 baths1,280 sq ft

103 Metcalf Rd, Chestertown, MD 21620

(855) 450-0442

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 108 Little Harbor Way, Chestertown, MD 21620

$635,000

— beds— baths— sq ft

108 Little Harbor Way, Chestertown, MD 21620

(410) 275-2118

Average home prices near Kingstown, MD

Cities

Church Hill homes for sale
$344,500
Stevensville homes for sale
$567,950
Rock Hall homes for sale
$379,500
Edgewood homes for sale
$305,000
Ridgely homes for sale
$319,000
Goldsboro homes for sale
$265,000
Grasonville homes for sale
$402,450
Chester homes for sale
$509,700
Centreville homes for sale
$529,000
Chestertown homes for sale
$500,000
Queenstown homes for sale
$450,000
Galena homes for sale
$328,500
Greensboro homes for sale
$273,990
Bowleys Quarters homes for sale
$699,450
Kent Narrows homes for sale
$1,150,000

Zip Codes

21690 homes for sale
21620 homes for sale
$375,000

Kingstown, MD real estate trends

$482K

Sale price

+37.6%
since last year

$229

Sale $/sq ft

+6.0%
since last year

Under list price

Days on market

Down payment

—

Total homes sold

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