Chestertown, MD homes for sale & real estate

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ABOUT THIS HOME
Chestertown, MD Homes for Sale
An impeccably maintained, perfectly positioned two bedroom, two and one-half bath condo featuring one of the best vistas of Chestertown and Chester River. It is nearly impossible for the body, mind and spirit of its residents and guests not to be "in a good place" on the cloudiest or most challenging of days. River House, with only five private residences, occupies the best real estate within this prized, friendly and well managed neighborhood called Chester River Landing. Historic downtown Chestertown and the Chester River Yacht & Country club are less than 2 minutes away, when you need a break from your enclave that includes marina, grill patio, crabbing/fishing pier, be

$695,000

2 beds2.5 baths1,550 sq ft

118 Little Harbor Way #201, Chestertown, MD 21620

$734 HOA • 2 garage spots • Community pool

(410) 778-3779

ABOUT THIS HOME
Chestertown, MD Homes for Sale
Located in Country Club Estates, on a lovely, corner lot with mature trees. Solid brick rancher with good bones. 3 bedrooms, 2 full baths. The basement has a workshop space and garage. Hardwood floors. Spacious family room with woodstove. Nice screened-in porch and outdoor patio with a fire pit. Home is ready for your finishing touches. Near the Chester River Yacht and Country Club and just a few minutes to historic downtown Chestertown.

$485,000

3 beds2 baths2,162 sq ft

25800 Collins Ave, Chestertown, MD 21620

1.27 acre lot • Built 1960 • Listed 6 days

(410) 778-0330

3D WALKTHROUGH

ABOUT THIS HOME
Chestertown, MD Homes for Sale
Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your private dock with new boat lift, sandy beach, and stunning new saltwater pool. Exposed beams, scalamandre wallpaper, and multiple fireplaces. First floor owners suite featuring reclaimed pine flooring, private laundry area, walk-in closet, gas fireplace and remodeled bath with soaking tub. Second floor owner's suite with additional laundry area and remodeled bath. Breezeway to the garage. New irrigation system to all fl

$2,750,000

5 beds4.5 baths4,305 sq ft

7989 Quaker Neck Rd, Chestertown, MD 21620

0.84 acre lot • 2 garage spots • Pool

(410) 778-0330

OPEN SAT, 1:30PM TO 3:30PM

ABOUT THIS HOME
Chestertown, MD Homes for Sale
Beautiful, like new rancher built in 2021 offers 4 bedrooms and 2 baths. Luxury vinyl tile throughout much of the house including the primary bedroom. Seller has upgraded all plumbing fixtures, added kitchen backsplash, added shiplap, fully fenced rear yard with vinyl fencing, and more. Open kitchen, dining and living area. Located 45 minutes from Bay Bridge with a short easy commute to Middletown, Dover, Annapolis and DC and the beautiful beaches. Minutes from Chestertown and Centreville. Located in QA County school district.

$359,900

4 beds2 baths1,400 sq ft

111 Cee Jay Rd, Chestertown, MD 21620

0.34 acre lot • Built 2021 • Listed 4 days

(410) 758-0333

ABOUT THIS HOME
Chestertown, 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

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

$379,900

3 beds1 bath1,805 sq ft

23110 Old Fairlee Rd, Chestertown, MD 21620

(855) 450-0442

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 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 10751 Millbrook Dr, Chestertown, MD 21620, 3 beds, 2 baths

$375,000

3 beds2 baths1,942 sq ft

10751 Millbrook Dr, Chestertown, MD 21620

(410) 643-2244

Property at 201 Boundary Ave, Chestertown, MD 21620, 3 beds, 3 baths

$449,000

3 beds3 baths3,096 sq ft

201 Boundary Ave, Chestertown, MD 21620

(410) 778-0330

Property at 24415 Chestertown Rd, Chestertown, MD 21620, 2 beds, 1 bath

$264,900

2 beds1 bath1,110 sq ft

24415 Chestertown Rd, Chestertown, MD 21620

(410) 673-3344

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

$509,900

4 beds2 baths2,220 sq ft

515 N Kent St, Chestertown, MD 21620

(410) 778-3779

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

$275,000

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

$745,000

4 beds3.5 baths2,917 sq ft

200 Washington Ave, Chestertown, MD 21620

(410) 778-3779

Property at 7483 Shortall St, Chestertown, MD 21620, 3 beds, 2 baths

$297,500

3 beds2 baths1,232 sq ft

7483 Shortall St, Chestertown, MD 21620

(443) 274-1900

Property at 103 Adela Way, Chestertown, MD 21620, 4 beds, 3.5 baths

$595,000

4 beds3.5 baths5,576 sq ft

103 Adela Way, Chestertown, MD 21620

(866) 987-3937

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

$255,000

3 beds2 baths1,140 sq ft

100 Metcalf Rd, Chestertown, MD 21620

(443) 829-5828

Property at 124 Char Nor Manor Blvd, Chestertown, MD 21620, 2 beds, 2 baths

$245,000

2 beds2 baths1,024 sq ft

124 Char Nor Manor Blvd, Chestertown, MD 21620

(443) 274-1900

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

$529,000

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

$375,000

4 beds3 baths2,630 sq ft

23043 Bay Shore Spur, Chestertown, MD 21620

(410) 639-4003

Property at 234 N College Ave, Chestertown, MD 21620, 2 beds, 1 bath

$164,000

2 beds1 bath1,296 sq ft

234 N College Ave, Chestertown, MD 21620

(410) 823-0033

Property at 5700 Johnsontown Rd, Chestertown, MD 21620, 3 beds, 1 bath

$125,000

3 beds1 bath1,144 sq ft

5700 Johnsontown Rd, Chestertown, MD 21620

(844) 837-5274

Property at 300 Merganser Dr, Chestertown, MD 21620, 3 beds, 1 bath

$190,000

3 beds1 bath1,260 sq ft

300 Merganser Dr, Chestertown, MD 21620

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 108 S Kent St, Chestertown, MD 21620, 1 bed, 1.5 baths

$315,000

1 bed1.5 baths936 sq ft

108 S Kent St, Chestertown, MD 21620

(410) 778-0330

Property at 21316 Persimmon Dr, Chestertown, MD 21620, 2 beds, 1 bath

$179,000

2 beds1 bath1,232 sq ft

21316 Persimmon Dr, Chestertown, MD 21620

(410) 810-0010

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

$325,000

3 beds1 bath1,128 sq ft

134 Char Nor Manor Blvd, Chestertown, MD 21620

(410) 714-9166

Property at 26933 Mallard Rd, Chestertown, MD 21620, 3 beds, 2.5 baths

$625,000

3 beds2.5 baths1,600 sq ft

26933 Mallard Rd, Chestertown, MD 21620

(410) 778-0330

Property at 907 N Meadowview Dr, Chestertown, MD 21620, 3 beds, 2.5 baths

$440,000

3 beds2.5 baths1,842 sq ft

907 N Meadowview Dr, Chestertown, MD 21620

(410) 778-0330

Property at 7961 Quaker Neck Rd, Chestertown, MD 21620, 5 beds, 4 baths

$1,550,000

5 beds4 baths4,167 sq ft

7961 Quaker Neck Rd, Chestertown, MD 21620

(410) 429-7425

Property at 112 Metcalf Rd, Chestertown, MD 21620, 3 beds, 1.5 baths

$265,000

3 beds1.5 baths1,280 sq ft

112 Metcalf Rd, Chestertown, MD 21620

(443) 292-6767

Property at 866 Washington Ave, Chestertown, MD 21620, 3 beds, 2 baths

$330,000

3 beds2 baths1,224 sq ft

866 Washington Ave, Chestertown, MD 21620

(410) 479-4663

Property at 23620 Lands End Rd, Chestertown, MD 21620, 5 beds, 7 baths

$4,850,000

5 beds7 baths9,852 sq ft

23620 Lands End Rd, Chestertown, MD 21620

(410) 778-3779

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

$648,750

4 beds3.5 baths2,008 sq ft

206 S Water St, Chestertown, MD 21620

(410) 810-0010

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

$475,000

4 beds2.5 baths2,258 sq ft

165 Char Nor Manor Blvd, Chestertown, MD 21620

(443) 274-1900

Property at 23393 Cacaway Farm Ln, Chestertown, MD 21620, 3 beds, 3.5 baths

$1,195,000

3 beds3.5 baths4,446 sq ft

23393 Cacaway Farm Ln, Chestertown, MD 21620

(410) 275-2118

Property at 5179 Quaker Neck Rd, Chestertown, MD 21620, 1 bed, 1 bath

$559,900

1 bed1 bath1,148 sq ft

5179 Quaker Neck Rd, Chestertown, MD 21620

(410) 705-6295

Property at 7514 Muirfield Dr, Chestertown, MD 21620, 3 beds, 2.5 baths

$797,000

3 beds2.5 baths2,522 sq ft

7514 Muirfield Dr, Chestertown, MD 21620

(410) 275-2118

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Average home prices near Chestertown, MD

Cities

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$264,000
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Ridgely homes for sale
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Joppatowne homes for sale
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Grasonville homes for sale
$372,500
Chester homes for sale
$510,000
Aberdeen homes for sale
$418,152
Centreville homes for sale
$539,950
Abingdon homes for sale
$485,000
Queenstown homes for sale
$499,900
Galena homes for sale
$265,000
Bowleys Quarters homes for sale
$499,900
Middle River homes for sale
$379,000

Zip Codes

21690 homes for sale
21620 homes for sale
$449,000

Chestertown, MD real estate trends

$310K

Sale price

-24.1%
since last year

$280

Sale $/sq ft

-0.53%
since last year

Under list price

4.2%

Days on market

Down payment

—

Total homes sold

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