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Chestertown MD Real Estate & Homes for Sale

120 Properties Found


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1–25 of 120 properties displayed
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Beds:
5
Baths:
5 Full/1 Half
Sq.Ft.:
10,870
Status:
Active
MLS#:
1000346718
Type:
Farm, Single Family-Detached
Subdivision:
Chestertown
Lot size:
300 Acres
Year built:
1990
Courtesy: Benson & Mangold, LLC
View additional info

300+/- acre waterfront estate with exceptional amenities. Main house with 7,500+/- sq ft, with a retreat feel and open floor plan. Indoor and outdoor pools, high elevation and expansive southern and western views down coveted West Fork Langford Creek. Boat house with 7'+.- MLW, tenant house, historic farm house, antique covered bridge, large barn, waterfowl ponds and 1.5+/- miles of shoreline.

Beds:
7
Baths:
7 Full/2 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
1008176730
Type:
Single Family, Single Family-Detached
Subdivision:
Quaker Neck
Lot size:
164.13 Acres
Year built:
1965
Courtesy: Cross Street Realtors LLC
View additional info

Bachelors Hope Farm, available for the first time in 50+ years, is a once-in-a-lifetime waterfront & hunting farm. 9,600 square foot, 7 bed Main Home is situated within feet of the Chester River. 420 foot dock has 8 feet MLW, water & electric, with railway. 3,000+ feet of River frontage with 1,400+ foot revetment. 164+ acres: 96 tillable, 43 wooded & 3 ponds. 4 bed Farm Home & barn. Exquisite & prestigious Quaker Neck locale.

Beds:
7
Baths:
7 Full/2 Half
Sq.Ft.:
9,651
Status:
Active
MLS#:
1002149830
Type:
Farm, Single Family-Detached
Subdivision:
Quaker Neck
Lot size:
164.13 Acres
Year built:
1965
Courtesy: Cross Street Realtors LLC
View additional info

Bachelors Hope Farm, available for the first time in 50+ years, is a once-in-a-lifetime waterfront & hunting farm. 9,600 square foot, 7 bed Main Home is situated within feet of the Chester River. 420 foot dock has 8 feet MLW, water & electric, with railway. 3,000+ feet of River frontage with 1,400+ foot revetment. 164+ acres: 96 tillable, 43 wooded & 3 ponds. 4 bed Farm Home & barn. Exquisite & prestigious Quaker Neck locale.

Beds:
5
Baths:
3 Full/2 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
1000084191
Type:
Single Family, Single Family-Detached
Subdivision:
None
Lot size:
45.93 Acres
Year built:
1957
Courtesy: Gunther-McClary Real Estate
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An elegant new offering located on the Chester River in Quaker Neck, just south of Historic Chestertown. This magnificent family residence has it all: ideal waterfront & wildlife habitat, a private pier w/ 3ft MLW, marvelous panoramic southern water views, a blend of open & wooded land, privacy, extensive gardens and is located in the premier estate area of Kent County.

Beds:
6
Baths:
5 Full/1 Half
Sq.Ft.:
5,190
Status:
Active
MLS#:
1000488876
Type:
Single Family, Single Family-Detached
Subdivision:
None
Lot size:
76.07 Acres
Year built:
1782
Courtesy: Brandywine Fine Properties
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A quintessential 76-acre Eastern Shore waterfront estate built in 1781 & restored in the 90's. Providence Plantation defines Country Elegance with a fabulous 1st floor master bedroom suite, a new 3 BR Tenant House, dock with lift and an in-ground pool. Enjoy the peace and serenity of the Eastern Shore outdoor life. Owner is Licensed Real Estate Agent.

Beds:
5
Baths:
5 Full/1 Half
Sq.Ft.:
5,190
Status:
Active
MLS#:
1000388182
Type:
Farm, Single Family-Detached
Subdivision:
None
Lot size:
76.07 Acres
Year built:
1781
Courtesy: Brandywine Fine Properties Sot
View additional info

A quintessential 76-acre Eastern Shore waterfront estate built in 1781 & restored in the 90's, Providence Plantation defines Country Elegance with a fabulous 1st flr MBR suite, a new 3BR tenant house, dock with lift & an in-ground pool. Enjoy the peace and serenity of Eastern Shore outdoor life. Agent/Owner

Beds:
4
Baths:
3 Full/2 Half
Sq.Ft.:
2,656
Status:
Active
MLS#:
1002273018
Type:
Farm, Single Family-Detached
Subdivision:
Quaker Neck
Lot size:
51.55 Acres
Year built:
1900
Courtesy: Cross Street Realtors LLC
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The location of the main house, 3 cottages, in-ground pool & pool house in the critical area buffer make this waterfront compound offering one that is extraordinary and extremely rare. Situated on the banks of Comegys Bight roughly 7.5 miles from Historic Chestertown is a 51.55-acre whimsical oasis with nature & riding trails, pastures, barns, farmland, woodlands... make this your Camelot...

Beds:
5
Baths:
4 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
1000083695
Type:
Farm, Single Family-Detached
Subdivision:
Chestertown
Lot size:
65.13 Acres
Year built:
1970
Courtesy: Meredith Fine Properties
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The Kentfields Farm-A country Estate for all seasons - Kentfields is located on Quaker Neck close to Chestertown on Maryland's beautiful Eastern Shore. This 65 acre estate on Jarrett Creek, just off the Chester River and Chesapeake Bay. The home provides a comfortable Eastern Shore lifestyle. A unique living/sporting/entertaining property.

Beds:
5
Baths:
2 Full
Sq.Ft.:
n/a
Status:
Active
MLS#:
1000083629
Type:
Farm, Single Family-Detached
Subdivision:
Pomona
Lot size:
113 Acres
Year built:
1810
Courtesy: Cross Street Realtors LLC
View additional info

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.

Beds:
5
Baths:
4 Full/1 Half
Sq.Ft.:
4,748
Status:
Active
MLS#:
1000084003
Type:
Farm, Single Family-Detached
Subdivision:
Quaker Neck
Lot size:
42.07 Acres
Year built:
1800
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Quintessential Eastern Shore Waterfront Farm is set on 42-acres with 690 ft. of water frontage and long views of the East Fork of Langford Creek. Tree-lined drive leads to the well-maintained home, c.1800. Features include a new dock and boat lift, rip-rap shoreline, 33-tillable acres, and outbuildings. Lovely private setting is great for hunting. Adjacent 11 acre waterfront lot is also available.

Beds:
3
Baths:
3 Full
Sq.Ft.:
n/a
Status:
Active
MLS#:
1004147827
Type:
Single Family, Single Family-Detached
Subdivision:
Historic Chestertown
Lot size:
12.35 Acres
Year built:
1800
Courtesy: Maryland Heritage Properties
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Amazing sense of peace emphasized by the quiet of authentic 18th c.brick architecture. Methodically restored honoring its origins and yet made comfortable with 21st c. amenities. Lovely WF cove on Lankford Creek. Minutes from Chestertown on highy desirable Quaker Neck peninsula. Surrounded by farmland. Several important outbuildings offer many lifestyle opportunities. Rare 13 ac.offering!

Beds:
4
Baths:
4 Full
Sq.Ft.:
4,402
Status:
Active
MLS#:
1005951739
Type:
Single Family, Single Family-Detached
Subdivision:
Quaker Neck
Lot size:
1.48 Acres
Year built:
1949
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

One of Chestertown's most prestigious addresses. Located on the river halfway between town and "The Club". 1.48 acres of privacy. Professionally maintained and landscaped. The house has had one addition and two remodels. Large open floor plan,pool, guest/in-law suite,golf, gazebo, boating all make for endless entertaining possibilities.

Beds:
5
Baths:
3 Full/2 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
1000869440
Type:
Single Family, Single Family-Detached
Subdivision:
Langford Farm
Lot size:
3.39 Acres
Year built:
1990
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Impressive brick colonial waterfront home on the East Fork of Langford Creek, with its own private dock. Detached 4 car garage with copious storage. Interior features include a first floor Master Bedroom, theater, bar and game room, and gourmet kitchen. Come see the extraordinary interior details. Situated on 3.4 beautifully landscaped acres.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
1001160002
Type:
Single Family, Single Family-Detached
Subdivision:
Langford Farm
Lot size:
4.39 Acres
Year built:
2001
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Peaceful,tranquil,beautiful and private just begin to describe this waterfront property on the East Fork of Langford.The grounds were designed by a landscape architect and are filled with indigenous plants and trees.The home is impeccably maintained with a bright open floor plan,new gourmet kitchen,hard wood floors,new systems and a view over the water of preserved land.Minutes from Chestertown.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
1000084097
Type:
Farm
Subdivision:
0
Lot size:
48 Acres
Year built:
1973
Courtesy: Gunther-McClary Real Estate
View additional info

A rare offering in an ideal location. 48 acres of farm fields,woods, waterfrontage w/ deep water & expansive panoramic views, prime hunting including puddle & diving ducks, turkey, deer, rockfish, multiple blinds, pond, oak tree-lined driveway, ranch house situated in an excellent spot w/ spectacular water views,easy access to the water, large detached garage and additional shed/barn, privacy...

Beds:
5
Baths:
4 Full
Sq.Ft.:
4,257
Status:
Active
MLS#:
1005644966
Type:
Single Family, Single Family-Detached
Subdivision:
Fairgale Properties
Lot size:
3.55 Acres
Year built:
2002
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Fairlee Creek waterfront haven is set on a private 3.5-acres with water views throughout the home. Built in 2002 with a 2005 addition, the open design with great room, large kitchen, loft and deck invites outdoor living and entertaining. Features include a first floor Master Suite, an in-law apartment and detached 2 car garage. Also included is a deeded boat slip with lift at the community dock. F

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
2,934
Status:
Active
MLS#:
1001986560
Type:
Farm, Single Family-Detached
Subdivision:
Fairgale Properties
Lot size:
20.18 Acres
Year built:
2018
Courtesy: Cross Street Realtors LLC
View additional info

Build your waterfront dream home on this little slice of heaven, offering the best of both worlds with 20+ acre of farmland and fringe woodlands on Fairlee Creek, with deeded slip at the private community dock with deep water! Hunting, fishing, horses, waterfront homestead...there are so many possibilities to enjoy the Eastern Shore lifestyle! Pictures show options & upgrades that can be built.

Beds:
3
Baths:
4 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
1001205824
Type:
Single Family, Single Family-Detached
Subdivision:
Sarah Skipper Lands
Lot size:
0.61 Acres
Year built:
1995
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Great Opportunity!! This beautifully built brick home has stunning water views from almost every room. The property boasts 3 bedrooms w/ 4.5 baths, slate roof, bulkhead, swimming pool, hot tub, back patio area, 2nd floor deck overlooking the river, finished bonus room w/ bath, and beautiful irrigated gardens w/ walkways.The property is being sold as-is.

Beds:
3
Baths:
3 Full
Sq.Ft.:
3,085
Status:
Active
MLS#:
1000083761
Type:
Single Family, Single Family-Detached
Subdivision:
Fairgale Properties
Lot size:
3.12 Acres
Year built:
1999
Courtesy: Gunther-McClary Real Estate
View additional info

Lovely home nestled amongst mature trees along the shoreline of Fairlee Creek. Built by the current owner, many well thought out features throughout. Currently first floor bedroom is used as a den with connected bath, gas fireplace. Cedar closets thru out house, wood floors, cedar board walls, outdoor shower and sink. Boat slip with lift at the community pier plus direct access to creek by steps.

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
3,128
Status:
NEW LISTING
MLS#:
1008575416
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
10 Acres
Year built:
2005
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Eastern Shore Georgian style home is situated on a serene, rural 10-acres, yet is conveniently located just 2 miles from the colonial town of Chestertown. Designed by the architect, Andrea Lombardini, and built in 2005, the thoughtfully designed interior lends an airy elegance harmoniously linking the sunlit living areas, including the first floor master suite. Taking full advantage of the pastoral views, the home showcases the finest details including random width wood floors, built-ins, high ceilings and a terrace overlooking the naturally beautiful setting. Chestertown offers a river walk, brick lined streets with 18th century homes, galleries, live theater and cafes. It enjoys a vibrant arts community, outdoor educational programs and is home to Washington College. Located about 90-minutes from Washington and Philadelphia.

Beds:
5
Baths:
4 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
1000339874
Type:
Single Family, Single Family-Detached
Subdivision:
Fairgale Properties
Lot size:
2.44 Acres
Year built:
2000
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Easy access to the Chesapeake Bay, waterfront house designed to be compatible with its surroundings, water views in each room. Vaulted ceilings, main floor living, 3 master suites. Almost 5,000 sq.ft. of living space. Indoor heated Endless Pool. Deep water slip; 2+ acres. Whole house generator. Convenient (within 90 min.) to 5 cities. Ideal for vacation/weekend ; host your family and friends.

Beds:
5
Baths:
3 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
1000177314
Type:
Single Family, Single Family-Detached
Subdivision:
Great Oak Estates
Lot size:
1.36 Acres
Year built:
1997
Courtesy: Gunther-McClary Real Estate
View additional info

Spectacular views of the Chesapeake Bay from nearly every room along with four seasons of sunsets nearly every night are included in this well meticulously maintained home. Fabulous kitchen for entertaining and a Master Bedroom suite perfect for relaxing. All just minutes from historic Chestertown. Co-broke commission will not be paid unless co-broke arranges and attends all showings

Beds:
3
Baths:
1 Full
Sq.Ft.:
n/a
Status:
Active
MLS#:
1002280432
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester Estates
Lot size:
1.33 Acres
Year built:
1937
Courtesy: Cross Street Realtors LLC
View additional info

Seller assumes buyer will be tearing down (or completely rebuilding) existing structures. Value is based on 200' of Chesapeake Bayfront, a "C" shaped assemblage of 3 parcels, 8 lots which includes one allocation for water/sewer. Several nearby neighbors have built/rebuilt Million$+ properties worthy of Architectural Digest. Several pictures provided for inspiration purposes!

Beds:
4
Baths:
5 Full
Sq.Ft.:
4,682
Status:
Active
MLS#:
1001989080
Type:
Single Family, Single Family-Detached
Subdivision:
Fairgale Properties
Lot size:
2.72 Acres
Year built:
2000
Courtesy: Cross Street Realtors LLC
View additional info

Located in an exclusive water-oriented community, this magnificent home offers an open plan design for those who enjoy entertaining and being active. The prominent eye-catching architectural style of the interior accents a classic paint scheme throughout. Various seating spaces, lavish main level master suite, large kitchen, sunroom, bonus room, 4 zones, 3-bay garage, deeded boat slip with 4' MLW

Beds:
5
Baths:
3 Full/1 Half
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
1009688038
Type:
Single Family, Single Family-Detached
Subdivision:
None
Lot size:
13.17 Acres
Year built:
2006
Courtesy: Champion Realty, Inc.
View additional info
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