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

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$3,489,000 143.4 acres 4 Beds | 4 Baths | 6448 sqft
6349 BROAD NECK ROAD, Chestertown, MD 21620 - 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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$1,975,000 113 acres 5 Beds | 2 Baths
6970 POMONA ROAD, Chestertown, MD 21620 - Kent County

113 acres Chestertown, MD

Magnificent 113 Acre Waterfront Farm with a Three-Bay Two-Story Brick Colonial built in 1810 near Historic Chestertown. 97.9 acres tillable, 13.9 acres in Conservation Reserve Program and 1 acre Wildlife Habitat Incentives Program - Impoundment. 1 Deep Water Pond. Tilling rights under lease for 2016 growing season.
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$995,000 23.23 acres 3 Beds | 4 Baths | 4000 sqft
9545 CHANTILLY FARM LANE, Chestertown, MD 21620 - 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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$890,000 2.44 acres 4 Beds | 6 Baths
9784 WHITE SWAN COURT, Chestertown, MD 21620 - 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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$675,000 20 acres 3 Beds | 3 Baths
310 HICKORY LANE, Chestertown, MD 21620 - 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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$649,000 20.06 acres 4 Beds | 3 Baths
22988 FAIRGALE FARM LANE, Chestertown, MD 21620 - Kent County

20.06 acres Chestertown, MD

20 acre horse farm on Fairlee Creek. Spacious home w/gourmet kitchen & intelligent floor plan oriented for big sky views. Lrg 2 story barn w/4+ stalls, covered loafing areas, abundant storage. Private comm. dock,1/2 mile to Chesapeake Bay by boat. At your fingertips fishing & hunting: plentiful schools, flocks and herds! Orchard & several strategic outbldgs. Excuse temporary cleanup & construction
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$649,000 20.06 acres 4 Beds | 3 Baths
22988 FAIRGALE FARM LN, Chestertown, MD 21620 - Kent County

20.06 acres Chestertown, MD

20 acre horse farm on Fairlee Creek. Spacious home w/gourmet kitchen & intelligent floor plan oriented for big sky views. Lrg 2 story barn w/4+ stalls, covered loafing areas, abundant storage. Private comm. dock,1/2 mile to Chesapeake Bay by boat. At your fingertips fishing & hunting: plentiful schools, flocks and herds! Orchard & several strategic outbldgs. Excuse temporary cleanup & construction
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$597,000 5.05 acres 4 Beds | 2 Baths
10050 FORREST LANE, Chestertown, MD 21620 - Kent County

5.05 acres Chestertown, MD

Best of all worlds in this waterfront home with easy water access and natural surroundings. Just feel the peace that engulfs you as you look out from the many windows of the great room. Boat, walk, bike, or drive to a marina, golf course, tennis, pool, restaurants and beach. A perfect Eastern Shore retreat. Co-broke commisssion will not be paid unless co-broke arranges and attends all showings
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$585,000 5 acres 5 Beds | 3 Baths
10258 MILL HOLLOW LANE, Chestertown, MD 21620 - Kent County

5 acres Chestertown, MD

This spacious, meticulously maintained home on a very private 5 acre perch offers 5 bedrooms, gourmet kitchen and plenty of entertainment space inside and out, just minutes from Chestertown. The large master bedroom, with sitting area, has master bath and attached walk-in closet. The 3 car detached garage provides plenty of space for cars and toys as well as a large work shop.
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$445,000 2.35 acres 4 Beds | 4 Baths | 2837 sqft
8335 BEAVER COURT, Chestertown, MD 21620 - 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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$398,000 3.79 acres 3 Beds | 5 Baths
22484 GOOSE HOLLOW DRIVE, Chestertown, MD 21620 - 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.
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$398,000 2.76 acres 4 Beds | 3 Baths
11062 AUGUSTINE HERMAN HIGHWAY, Chestertown, MD 21620 - 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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$384,900 2.22 acres 4 Beds | 3 Baths
8320 BEAVER COURT, Chestertown, MD 21620 - Kent County

2.22 acres Chestertown, MD

Cape Cod designed wood sided home w/1st floor master, 3 additional bedrooms upstairs, formal living & formal dining room, family room w/fireplace, family area with skylights on the 2nd level, composite rear deck, patio and a 23' x 15' shed. There is even a 3 car garage w/one bay used as a heated & cooled workshop. Beautifully landscaped & meticulously maintained yard. Conditioned crawl space too!!
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$359,900 2.05 acres 4 Beds | 3 Baths
8923 ORCHARD DRIVE, Chestertown, MD 21620 - Kent County

2.05 acres Chestertown, MD

Incredible offering located in Orchard Hill. This home has it all....a 2 story entrance foyer, 4 bedrooms, a huge master suite, living room with fireplace, family room with fireplace, spacious laundry room, kitchen with island and a formal dining room. The screened in rear porch is ideal for warm weather entertaining. There is an oversized garage with room for a workshop. Freshly painted inside!
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$329,000 54.68 acres
0 Ewingtown Road, Maryland, Chestertown, MD 21620 - Kent County

54.68 acres Chestertown, MD

54.678, +/- acres with approx. 37 tillable and 13 wooded w/stream. Great hunting property. No deed restrictions. Surveyed in 2010. 2 approved percs. 2 parcels selling as 1. Within 10 minutes of Historic downtown Chestertown, MD where there are schools, restaurants, hospital, shopping, churches, etc...