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Chestertown, Maryland: Country Homes, Houses, and Rural Real Estate

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$3,900,000 143.4 acres 4 Beds | 4 Baths | 6448 sqft
6349 BROAD NECK ROAD, Chestertown, MD - Kent County

143.4 acres Chestertown, MD

Kings Prevention, Circa 1779, is situated on the East Fork of Langford Creek across from The Reward. Renovated in 1992, this historic Kent County waterfront farm offers a grand estate w/tenant house, guest house, lap pool w/pool house, tennis court, and horse stable barn bordered by 81 tillable ac, 60 acres of woodland further improved w/waterfowl pond. Extended dock w/7'+ MLW.
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$2,375,000 65.13 acres 5 Beds | 5 Baths
5793 QUAKER NECK LANDING ROAD, Chestertown, MD - Kent County

65.13 acres Chestertown, MD

This farm,"Kentfields" has the "Eastern Shore Feel"; from the cedar lined lane, ponds, tennis court, 3br 2ba tenant house, pool, dock on the creek, great gardens, historic barn. Spacious comfortable 5br 4.5 ba house overlooking 1/2 mile of waterfont, privacy, and all that nature. This small plantation has a patina and an ambiance that makes it so special. What a place to celebrate the family.
30 photos
$1,975,000 65.52 acres 5 Beds | 5 Baths | 4968 sqft
27349 VENARINGHAM LANE, Chestertown, MD - Kent County

65.52 acres Chestertown, MD

Waterfront farm on the Chester River with marvelous hunting off the marsh & on 2 ponds. House has 4 BR, 3 1/2 baths, plenty of closets space, new open addition in 2003 w/tile hot tub & 6.5 x 12 sauna. 3 Car garage w/lrg guest room, full BA, sink & frig. 3 Morton buildings, 20 acres fenced. Orchard. Electric lift on pier, beach and picnic area. Expansive views. Well maintained property & imps.
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$995,000 23.23 acres 3 Beds | 4 Baths | 4000 sqft
9545 CHANTILLY FARM LANE, Chestertown, MD - Kent County

23.23 acres Chestertown, MD

Stunning views of the Chesapeake Bay & abundant wildlife are enjoyed by this secluded 23 acre waterfront retreat. Situated within the critical area buffer, the home was rebuilt in 2007 & custom designed to maximize water views. Hickory hardwood flooring and cabinetry, an open floor plan & a loft style upper level den - great for entertaining! 1000 ft beachfront, wooded trails and open fields.
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$990,000 2.44 acres 4 Beds | 6 Baths
9784 WHITE SWAN COURT, Chestertown, MD - Kent County

2.44 acres Chestertown, MD

Are you young enough to participate in Chestertown's sporting activities; swimming, ,fishing ,kayaking, rowing club, sailing school, golf, & hiking. Are you old enough to enjoy & appreciate Chestertown's fine dining,great sunsets, birding ,boating, fishing, hunting,WC-ALL education,National Music Festival, The Arts, The Farmer's Market & First Fridays. If so this is the house for you.
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$795,000 27 acres 5 Beds | 3 Baths | 4584 sqft
8046 QUAKER NECK ROAD, Chestertown, MD - Kent County

27 acres Chestertown, MD

RADCLIFFE CROSS - Fine old brick Georgian residence w 27 creek-front acs. Main house + tenant house. Just blocks into heart of Historic Chestertown & Washington College. Wood floors, high ceilings & an important grand central hall & stairway. Stunning light-filled rooms. Stable & outbuildings. 2 parcels. Public sewer. Radcliffe Creek offers quick kayak/canoe access to the whole of Chester River.
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$736,000 2.12 acres 4 Beds | 3 Baths
10332 JOHN CARVILL ROAD, Chestertown, MD - Kent County

2.12 acres Chestertown, MD

Long time owner has kept this home in tip top shape. Beautiful landscaped grounds. Spacious living areas. Balcony front and back. Private sun deck off bedrooms with wonderful view of Fairlee Creek out to the Bay. Private pool. Pier with lift. Walking distance to Great Oak Landing, voted Best of the Bay. Restaurant, pool, Kids Club, tennis, golf, marina, entertainment. Great Oak, great for all.
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$725,000 2 acres 3 Beds | 3 Baths
10709 TILDEN LANE, Chestertown, MD - Kent County

2 acres Chestertown, MD

Unique opportunity to own a 20th Century waterfront Victorian in the country. Enjoy the serenity and privacy of Worton Creek where the only sounds you hear are the birds calling. Great location--- only 5 minutes from the Chesapeake Bay from your private dock, and only 8 minutes drive to Historic Chestertown. New: Kitchen-2011, HVAC-2012, Roof-2015.Stand- by automatic Generator.
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$675,000 20 acres 3 Beds | 3 Baths
310 HICKORY LANE, Chestertown, MD - Queen Annes County

20 acres Chestertown, MD

Rustic, contemporary home with amazing country kitchen, ideal water views of the Chester River, and close to historic Chestertown. On 20 acres of land with 600' of waterfront (permit-able Boardwalk and Pier).
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$450,000 2.35 acres 4 Beds | 4 Baths | 2837 sqft
8335 BEAVER COURT, Chestertown, MD - Kent County

2.35 acres Chestertown, MD

Builder's home in Fannell's Meadow with in-law/au-pair apartment! Gleaming wood floors, crown molding & superior construction in this 4 bedroom, 4 bath home on 2.35 manicured acres! Impeccably maintained inside & out with mature landscaping. 3-zone heat & A/C systems, new septic, 2 hot water heaters & 2-car garage w/ work area. Relax on the porch or dine on the deck. You'll love calling this home!
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$435,000 19.81 acres 3 Beds | 2 Baths
8276 BROAD NECK ROAD, Chestertown, MD - Kent County

19.81 acres Chestertown, MD

The winding drive takes you to this private retreat on 19+ wooded acres with pond & stream. Spacious home with large country kitchen, LR, DR and sunny sitting rm. Unfinished room has potential for 1st floor master suite. Partially finished basement has ground level walkout. Attached two car garage and detached storage barn with attic. Property in Forest Conservation program. No drive by.
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$435,000 2.76 acres 4 Beds | 3 Baths
11062 AUGUSTINE HERMAN HIGHWAY, Chestertown, MD - Kent County

2.76 acres Chestertown, MD

Beautiful home overlooking a lake, with a wonderful mother in law's apartment in the walk out apartment via sliding doors to a covered porch. Home has beautiful wood floors, amenities including wainscoating, a Florida Room, a large master bedroom, family room with gas fireplace, and an office area downstairs. Detached metal building 19 x 18 building with 220, concrete floor. Mower conveys
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$398,000 3.79 acres 3 Beds | 5 Baths
22484 GOOSE HOLLOW DRIVE, Chestertown, MD - Kent County

3.79 acres Chestertown, MD

Enjoy all the best nature has to offer. Large home with two garages, huge deck overlooking the water. Privacy and close to historic Chestertown.
$398,000 3.79 acres 3 Beds | 5 Baths
22484 GOOSE HOLLOW DRIVE, Chestertown, MD - Kent County

3.79 acres Chestertown, MD

The ~best waterfront buy~ now on the market. Relax in this large home with 2 garages, huge deck overlooking the water, open floor plan, 2 fireplaces and much more. A must-see property at a terrific price. Almost 4 acres offering plenty of privacy, yet close to historic Chestertown.
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$374,000 20 acres 3 Beds | 3 Baths
10095 WORTON ROAD, Chestertown, MD - Kent County

20 acres Chestertown, MD

20 acre farmette with 2 ponds and a completely restored farm house built in the 1800's, with some original flooring and original staircase. Offers about 14 acres of tillable ground, a 3 car detached garage, milk house and 2 bay open shed plus a first floor owners suite, large kitchen with center island and skylight, family room with vaulted ceiling off of the formal dining room and new windows!