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Olivia Ryan Broker/Owner
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Chestertown MD Real Estate & Homes for Sale

146 Properties Found


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1–25 of 146 properties displayed
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Beds:
5
Baths:
5 Full/1 Half
Sq.Ft.:
n/a
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:
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
View additional info

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
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 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:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,498
Status:
Active
MLS#:
1000368034
Type:
Farm, Single Family-Detached
Subdivision:
Airy Hill
Lot size:
136.29 Acres
Year built:
1989
Courtesy: Select Land & Homes, LLC
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136.5 acres of prime, gently rolling, fertile farmland in Kent County! First time and rare offering with Community Residential zoning with the best of locations on the fringe of Chestertown! Lovely 3bd, 2.5ba cape cod home and barn overlooking 5 acre sanctuary pond. Additional features include excellent waterfowl hunting, extensive road frontage and mostly all tillable. Possibilities are endless.

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
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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
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Quintessential Eastern Shore Waterfront Farm is set on 42-acres with 690 ft. of water frontage and long views of Langford Creek. Inviting tree-lined drive leads to the lovely, well-maintained home, c.1800. Property features rip-rap shoreline, 33-tillable acres, outbuildings and garage. Enjoy the local wildlife, hunting or water activities. Adjacent 11 acre waterfront lot is available for $375,000.

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:
5
Baths:
3 Full/1 Half
Sq.Ft.:
4,428
Status:
Active
MLS#:
1000245102
Type:
Single Family, Single Family-Detached
Subdivision:
None
Lot size:
3.4 Acres
Year built:
1950
Courtesy: Cross Street Realtors LLC
View additional info

Magnificent waterfront home offers incredible sunsets & broad views of the Chester River w/ floor to ceiling windows. Beautiful architectural entryway, gourmet kitchen & large master suite w/ walk-in closet. Waterside pool w/ screened porch, pool/guest house, stone pathways & patios. Private setting on 3 acres w/ 300~ of shoreline, sandy beach & private dock. Minutes from Downtown Chestertown!

Beds:
5
Baths:
3 Full
Sq.Ft.:
4,435
Status:
Active
MLS#:
1001651462
Type:
Single Family, Single Family-Detached
Subdivision:
Chantilly Farm
Lot size:
10.16 Acres
Year built:
2009
Courtesy: Gunther-McClary Real Estate
View additional info

Exceptional design overlooking a gorgeous tidal lake and the Chesapeake Bay. Just in from the shipping channel, affording spectacular views of large ships silently going by. It is a virtual Nat-Geo show year-round, gorgeous vistas from almost every room in the house. Wrap-around porch for bay breezes. Highly efficient, superior construction. Put this one on your must-see list, as soon as possible.

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...

Open House:

Saturday, 7/21 10:00-1:00PM

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:
5
Baths:
3 Full/1 Half
Sq.Ft.:
4,416
Status:
NEW LISTING
MLS#:
1001975094
Type:
Single Family, Single Family-Detached
Subdivision:
Fairgale Properties
Lot size:
1.95 Acres
Year built:
2004
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Fabulous Water Front Beauty. Perfect in every detail! Gleaming wood floors, 4 fireplaces. Gourmet Kitchen with High End appliances. Master suite with gorgeous Bath, extra large walk in closet and deck. Living Room has tray ceiling and built-in cabinets/shelves. Enjoy the lovely views of landscaping and Fairlee Creek. 3.5 bay garage. Deep water slip has 10,000 lb metal boat lift, a short walk away.

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
2,934
Status:
NEW LISTING
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:
3 Full
Sq.Ft.:
n/a
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:
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:
4
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

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.

Beds:
4
Baths:
5 Full
Sq.Ft.:
4,682
Status:
NEW LISTING
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.:
5,367
Status:
NEW LISTING
MLS#:
1002024942
Type:
Farm, Single Family-Detached
Subdivision:
Gorgeous & A Must See! Like New!!
Lot size:
13.17 Acres
Year built:
2006
Courtesy: Champion Realty, Inc.
View additional info

This is it!! Fabulous Custom-Built Home to the highest standards boasting a modern open floorplan, Chef's Designer kitchen including, What! - 3 Ovens!!, Outer Banks inspired wall of glass in family room w/FP, 5367 sf + 2500 sf basement & woodstove, 20x22 screened porch, second floor balcony overlooking FR & kit, gleaming hardwood flrs, Awesome home for entertaining perched on over 13 acres-Hurry!

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
4,086
Status:
Active
MLS#:
1000083781
Type:
Single Family, Single Family-Detached
Subdivision:
Historic Chestertown
Lot size:
0.28 Acres
Year built:
1788
Courtesy: Maryland Heritage Properties
View additional info

Fine landmark property rarely available. Brick w all refinements of 1788 c. maintained w great care. Grand stair hall flows to all social rooms. Perfect "stage" for fine collections. Quiet setting in Chestertown Hist. Dist. Handsome glass sunporch overlooks private garden & 3car garage wi climatized room + workshop/garden area & large open studio/office. Immediate to River/shops/Arts/live theatre.

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
1000083825
Type:
Single Family, Single Family-Detached
Subdivision:
N/A
Lot size:
0.24 Acres
Year built:
1903
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

A Classic American Victorian ,wrap-around porch with balustrade. Many new appointments, including a new kitchen & new baths, while retaining the Victorian signatures of high ceilings, spacious rooms, fine wood floors, detailed wood trim, long windows, arched halls & graceful staircase. Rear & side gardens, 2 car detached garage with wine room & potting shed at the end of this Water St. driveway.

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
1005560717
Type:
Single Family, Single Family-Detached
Subdivision:
Country Club Estates
Lot size:
0.46 Acres
Year built:
1994
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Beautiful home placed along the 13th fairway of the Chester River Yacht & Country Club. Sit in the pool, porch, hot tub, enjoy the manicured golf course with views of the Chester River in the distance.1st & 2nd floor masters sitting room,washer/dryer on each floor. 9' ceilings, oak floors,den & withdrawing room, good flow for entertaining. Just relax and enjoy; right here!

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