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Maryland
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Chestertown
Homes for sale in Chestertown, Maryland
Date (newest first)
Price (lowest first)
Price (highest first)
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202 Byford Dr, Chestertown, MD 21620
Great street in Byford Heights. Basic rancher for living on one floor; the house has "Good Bones" on a lovely lot....
Houses Chestertown
339,900
$
View pictures
104 Silver Heel Dr, Chestertown, MD 21620
Welcome to 104 Silver Heel Dr a single family FIVE bedroom, 3 FULL bathroom home in the sought after but sold out...
Houses Chestertown
360,000
$
View pictures
331 Park Ln, Chestertown, MD 21620
Eastern Shore Waterfront Home is set on 5-acres on Rosin Creek in Queen Anne's County, Maryland. The home is located...
Houses Chestertown
1,200,000
$
View pictures
614 High St, Chestertown, MD 21620
ALL OFFERS SHOULD BE SUBMITTED BY 5:00 pm on 3/9/24. In town location for under $200K! This recently renovated and...
Houses Chestertown
195,000
$
View pictures
2007 Pondtown Rd, Chestertown, MD 21620
1900's Bungalow sitting on a 4 Acre Lot out in the country. The dwelling is in need or major repairs or replacement....
Houses Chestertown
69,900
$
View pictures
134 Char nor Manor Blvd, Chestertown, MD 21620
(Pictures will be uploaded March 11th) Welcome to this cozy 3 bedroom, 1 bath completely remodeled home with views of...
Houses Chestertown
449,000
$
View pictures
612 High St, Chestertown, MD 21620
Renovated and remodeled in town location for under $200K! Updates include kitchen, mud room with laundry and a half...
Houses Chestertown
185,000
$
View pictures
703 High St, Chestertown, MD 21620
Welcome to Chestertown. Enjoy all that living on the Eastern shore has to offer. Enjoy Saturday morning farmers...
Houses Chestertown
275,000
$
View pictures
204 N Mill St, Chestertown, MD 21620
Welcome to a rare Downtown Chestertown investment gem that awaits your transformative touch! This is more than a...
Houses Chestertown
399,000
$
View pictures
707 Round Top Rd, Chestertown, MD 21620
Be sure to check out the photos - this home has real charm and character! This well-maintained house has been home...
Houses Chestertown
340,000
$
View pictures
7280 Swan Creek Rd, Chestertown, MD 21620
Nestled upon a picturesque 10-acre expanse along the tranquil shores of the Chesapeake Bay, this waterfront home...
Houses Chestertown
1,395,000
$
View pictures
148 Grant Ct, Chestertown, MD 21620
This barely lived in rancher, located in a cul-de-sac, offers breathtaking sunrises and sunsets with amazing...
Houses Chestertown
450,000
$
View pictures
209 Myers Rd, Chestertown, MD 21620
Welcome to this charming rancher located in the sought-after community of The Grove. With over 2200+ square feet this...
Houses Chestertown
445,000
$
View pictures
316 Roosevelt Dr, Chestertown, MD 21620
Completely renovated!! Kitchen has new Samsung stainless steel appliances. Slide in electric stove, built in...
Houses Chestertown
299,900
$
View pictures
215 Blakefield Dr, Chestertown, MD 21620
Introducing this stunning new construction home just outside of Chestertown, MD in the Blakefield community ( QA...
Houses Chestertown
429,900
$
View pictures
870 Washington Ave, Chestertown, MD 21620
Excellent Location! This charming 3-bedroom, 1-bathroom bungalow sits proudly along one of Chestertown's primary...
Houses Chestertown
285,000
$
View pictures
9020 Cumberland St, Chestertown, MD 21620
Two perfectly adorable cottages in Tolchester. Both were completely remodeled. The cottages sit on 3 lots totaling...
Houses Chestertown
309,900
$
View pictures
403 E Campus Ave, Chestertown, MD 21620
Welcome to this charming 3-bedroom, 1-bathroom Ranch-style home, designed for convenient single-level living....
Houses Chestertown
299,900
$
View pictures
7979 Sandy Bottom Rd, Chestertown, MD 21620
Welcome to the former historic HILLTOP HOTEL! A charming estate which underwent significant renovations in 2021 while...
Houses Chestertown
739,900
$
View pictures
22900 Handy Point Road Handy Point Rd, Chestertown, MD 21620
Beautiful Dutch Colonial on 3 Acres with 500 +/- feet of waterfront overlooking Worton Creek. Near Worton Creek...
Houses Chestertown
1,800,000
$
View pictures
106 Water Street N #1/2, Chestertown, MD 21620
This former horse barn was converted in 1990 into a well-crafted personal residence. In early 2018, the current...
Houses Chestertown
750,000
$
View pictures
Landing Ln #37, Chestertown, MD 21620
Welcome home to this stunning new construction in Chestertown's prestigious waterfront community, Chester River...
Houses Chestertown
725,000
$
View pictures
207 N Queen St, Chestertown, MD 21620
Holiday special! For the month of December, sellers are offering a $20,000 credit toward the buy down of your...
Houses Chestertown
699,900
$
View pictures
201 N Water St, Chestertown, MD 21620
SMITH-RINGGOLD HOUSE. This exceptional property is a rare find: an authentic waterfront 18th century home with 21st...
Houses Chestertown
1,725,000
$
View pictures
305 Pine Tree Rd, Chestertown, MD 21620
Welcome to this newly renovated home with stunning upgrades throughout! This charming, easy-living home, in...
Houses Chestertown
275,000
$
View pictures
Little Harbor Way #1, Chestertown, MD 21620
Introducing a stunning new construction waterfront home in Chestertown's prestigious waterfront community, Chester...
Houses Chestertown
1,499,000
$
View pictures
114 School Rd, Chestertown, MD 21620
Location, location, location! Located in College Heights and just a few short blocks from Washington College and a...
Houses Chestertown
249,900
$
View pictures
866 Washington Ave, Chestertown, MD 21620
Endless possibilities for this centrally located property in Chestertown, across from Kent Plaza Shopping Center and...
Houses Chestertown
334,900
$
View pictures
1006 Twin Ct, Chestertown, MD 21620
Spacious, well-situated 3 or 4 bedroom, 2.5 bathroom rambler on almost 3/4 of an acre just outside downtown...
Houses Chestertown
340,000
$
View pictures
116 Harlan Loop, Chestertown, MD 21620
Main Level Features Dining Room, Living Room, Family Room, Kitchen with Breakfast Nook Bump Out, Laundry Room, Half...
Houses Chestertown
328,500
$
View pictures
203 Radcliffe Dr, Chestertown, MD 21620
HUD home SOLD STRICTLY AS IS . Calling all investors and homeowners with an eye for opportunity! Uncover the untapped...
Houses Chestertown
220,000
$
View pictures
101 S Kent St, Chestertown, MD 21620
Welcome to 101 S. Kent St! Prepare to be charmed by this beautifully updated and lovingly maintained historic home,...
Houses Chestertown
395,000
$
View pictures
204 Mill St, Chestertown, MD 21620
Bask in the beauty of this incredible 1920s home in downtown Chestertown! At 2890 square feet, this freshly painted 5...
Houses Chestertown
429,900
$
View pictures
205 N Water St, Chestertown, MD 21620
This remarkable 4BR/3.5BA waterfront home boasts historic elegance and beautiful water views! The best of both...
Houses Chestertown
950,000
$
View pictures
10605 Tonopah Rd, Chestertown, MD 21620
Come by this AWESOME, RENOVATED Rancher in the WATERFRONT Community of Chesapeake Landing is Chestertown. This...
Houses Chestertown
299,900
$
View pictures
248 Devon Dr, Chestertown, MD 21620
Great home located in desired Coventry Farms community of Chestertown. This home offers plenty of space for...
Houses Chestertown
460,000
$
View pictures
209 E Campus Ave, Chestertown, MD 21620
Nestled within the desirable community of College Heights, this charming Colonial-style home offers the perfect blend...
Houses Chestertown
449,000
$
View pictures
410 Cannon St, Chestertown, MD 21620
One of the last available 1920s houses available in downtown Chestertown that is ready to be lived in and priced to...
Houses Chestertown
299,000
$
View pictures
131 133 and 129 Flatland Rd, Chestertown, MD 21620
"Strawboard Mill" offers 2 brick, townhomes (each townhouse has 2 units), with metal roofs, 1 efficiency apartment...
Houses Chestertown
1,095,000
$
View pictures
109 Water Street N, Chestertown, MD 21620
Welcome to the Esau Watkins House (circa 1739), believed to be the earliest remaining dwelling on the Chester River...
Houses Chestertown
998,500
$
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