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Chestertown MD Real Estate & Homes for Sale

117 Properties Found


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1–25 of 117 properties displayed
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Beds:
5
Baths:
3 Full/2 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
1000084191
Type:
Other
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:
5
Baths:
4 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
1000083695
Type:
Other
Subdivision:
Chestertown
Lot size:
65.13 Acres
Year built:
1970
Courtesy: Meredith Fine Properties
View additional info

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:
3
Baths:
4 Full/1 Half
Sq.Ft.:
4,436
Status:
Active
MLS#:
1003274369
Type:
Other
Subdivision:
N/A
Lot size:
152.49 Acres
Year built:
1940
Courtesy: Cross Street Realtors LLC
View additional info

Buckingham Farm, fronting the Chester River, is one of the most picturesque horse farms in MD. This prominent Thoroughbred Horse breeding operation raised home-bred, stakes-placed winners such as Green Alligator, Master Speaker, Crab Cakes...Receiving just as much love & attention was the property itself -152.49 acres improved w/main residence, historic train station, caretaker house, barns...

Beds:
5
Baths:
2 Full
Sq.Ft.:
n/a
Status:
Active
MLS#:
1000083629
Type:
Other
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:
Other
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 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:
Other
Subdivision:
Historic Chestertown
Lot size:
12.35 Acres
Year built:
1800
Courtesy: Maryland Heritage Properties
View additional info

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:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA10056028
Type:
Single Family-Detached
Subdivision:
SARAH SKIPPER LANDS
Lot size:
0.61 Acres
Year built:
1995
A broker reciprocity listing Courtesy: The Hogans Agency
View additional info

Located across the river from Historic Chestertown, this private, well landscaped, Dutch Colonial is the perfect getaway! Entertain with ease with the spacious open first floor and french doors leading to the waterfront deck, patio, pool, and hot tub. Sit out on the balcony from any of the 3 adjoining bedrooms and enjoy the views the Chester River has to offer - there is something for everyone!

Beds:
5
Baths:
3 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
1000083861
Type:
Other
Subdivision:
Langford Farm
Lot size:
4.42 Acres
Year built:
1998
Courtesy: Cross Street Realtors LLC
View additional info

An exquisite custom built home w/ incredible architectural detail! Reclaimed VT barn hardwood floors; 1st floor master w/ luxurious ensuite bath & walk-in closets; gourmet kitchen; sweeping river views from almost every room; pier w/ boat lift, floating dock & 4+ MLW depth; 3 bay garage w/ breezeway; whole-house backup generator; too many more to list! Private, but only 10 min to Downtown!

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
2,940
Status:
Active
MLS#:
1003269273
Type:
Single Family
Subdivision:
Langford Farm
Lot size:
2.45 Acres
Year built:
1997
Courtesy: Cross Street Realtors LLC
View additional info

Exquisite Waterfront with Highly Efficient "Smart-Home" Systems & Mechanics + Pool Permit! Gourmet kitchen, well-appointed detail throughout - from heated flooring to imported Mexican tile. All new plumbing, faucets, toilets and the list goes on... Large screened porch off of the kitchen and one off of the master bedroom... On every level, this is the Finest waterfront offering in the County!

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
1000084097
Type:
Other
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 huniting including puddle & diving ducks, turkey, deer, rockfish, multiple blinds, pond, tree-lined driveway w/ mature oak trees, ranch house situated in an excellent spot w/ spectacular water views, large detached garage and additional shed/barn, privacy & much more.

Beds:
4
Baths:
3 Full
Sq.Ft.:
3,778
Status:
Active
MLS#:
1001654255
Type:
Other
Subdivision:
Chantilly Farm
Lot size:
30.45 Acres
Year built:
1955
Courtesy: TTR Sotheby's International Realty
View additional info

SPECTACULAR VIEWS FROM THIS 30 ACRE ESTATE ON THE CHESAPEAKE BAY WITH 1000 ft OF SHORE LINE AND GRADUAL SLOPE TO WATER, SANDY BEACH, GUEST COTTAGE, WINE CELLAR IN LARGE BASEMENT, 3 CAR GARAGE, GENERATOR, UNLIMITED WILDLIFE AND BEAUTY EVERYWHERE! FRESH WATER POND, TROMBE WALL, PASSIVE SOLAR BUILDING DESIGN IN FAMILY ROOM. HOUSE AND PROPERTY HAVE BEEN IMMACULATELY MAINTAINED.

Beds:
5
Baths:
3 Full/1 Half
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
1004451871
Type:
Single Family
Subdivision:
Langford Farm
Lot size:
3.43 Acres
Year built:
1994
Courtesy: Doug Ashley Realtors, LLC
View additional info

Very nice home on the East Fork, Langford Creek. There is a dock with 3+ MLW, w/ electric/water at the dock. Swimming pool, covered deck, mature trees, beautiful yard. Open floor plan inside with living room, family room with fireplace, updated kitchen. Fresh paint, wood floors, new carpet upstairs, 1st floor suite, Water views from most rooms of the home. Nice waterfront!

Beds:
3
Baths:
3 Full
Sq.Ft.:
n/a
Status:
Active
MLS#:
1000083761
Type:
Other
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.

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
1000083825
Type:
Single Family
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.:
4,086
Status:
Active
MLS#:
1000083781
Type:
Other
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:
4.00
Sq.Ft.:
4,086
Status:
Active
MLS#:
KE9777301
Type:
Single Family-Detached
Subdivision:
HISTORIC CHESTERTOWN
Lot size:
0.28 Acres
Year built:
1788
A broker reciprocity listing 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:
3
Baths:
2 Full
Sq.Ft.:
n/a
Status:
Active
MLS#:
1003667093
Type:
Single Family
Subdivision:
Sarah Skipper Lands
Lot size:
0.85 Acres
Year built:
1964
Courtesy: Doug Ashley Realtors, LLC
View additional info

Sweeping views of the Chester River can be experienced from most rooms in this exquisitely renovated Contemporary home! Updates in past 7 years include new HVAC, new roof, new kitchen, new master bath, new 2nd bath, new Trex deck and more! The open floor plan is perfect for formal or casual entertaining. 95'+/- dock with 3'+/- MLW. No flood insurance! Across the river from Historic Chestertown.

Beds:
4
Baths:
4 Full
Sq.Ft.:
3,257
Status:
Active
MLS#:
1000084315
Type:
Single Family
Subdivision:
Country Club Estates
Lot size:
0.92 Acres
Year built:
1969
Courtesy: Cross Street Realtors LLC
View additional info

If your golf game had as much attention to detail as this stunning country club home, you'd be a Pro! Situated just off the 13th hole, this timeless design radiates both elegance & comfort while expansive views over the course to the Chester River relax the soul. 2 master suites, gourmet kit, wet bar, great room, library, apartment, generous/custom storage capacity & an abundance of built-ins...

Beds:
4
Baths:
4 Full
Sq.Ft.:
2,800
Status:
Active
MLS#:
1002790493
Type:
Other
Subdivision:
Scott's Point
Year built:
2008
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Fabulous Townhouse in desirable Scott's Point. Great waterviews of the Chester River & Wilmer Park. 2 deeded boat slips. Open Floor plan is enhanced by beautiful wood floors and cabinets. Wonderful Gourmet Kitchen opens to dining and living area. Balconies on each floor. First Floor Den options as bedroom. Large open airy rooms gives simple elegance with light. Walkable to everything downtown!

Beds:
6
Baths:
6 Full
Sq.Ft.:
n/a
Status:
Active
MLS#:
1000084105
Type:
Other
Subdivision:
Historic Chestertown
Lot size:
1.15 Acres
Year built:
1860
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

The John L Stam House, circa 1860, is a beautifully restored Gothic Revival Victorian. Currently run as a B&B there are 4 guest rooms with full baths and an additional 2 BR in the owners quarters. The first floor features original faux painted fireplaces, hand painted plastered ceilings, and "Jenny Doors" leading to a gracious veranda. A recently added water feature enhances the beautiful gardens

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
1000084063
Type:
Single Family
Subdivision:
N/A
Lot size:
0.22 Acres
Year built:
1900
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

This Beaux Art house is European/Mediterranean with a splash of Spanish influence; on the Chester River; in Historic Chestertown. Huge front hall, enormous Great room, River room, attached heated Spa & garden room + skylights. Large Master, sitting room & master bath. 2 car attached garage. Double lot. Enjoy the river from inside or on the Terrace. Unique house in the heart of a special town.

Beds:
3
Baths:
3 Full/1 Half
Sq.Ft.:
3,768
Status:
Active
MLS#:
1000083919
Type:
Other
Subdivision:
Rural Kent County 10 Min From Chestertown
Lot size:
10.01 Acres
Year built:
1987
Courtesy: Maryland Heritage Properties
View additional info

A Greg North INGENIOUS RENOVATION! Built 1987. Transformed into 18th c period home. Exquisite details - floors, light fixtures, hardware, moldings, plus. Stunning "Great Room" w brick floor & massive period fireplace & paneling. Social spaces beautifully presented. 10.1 acres (Ag. tax credits?). 3120 sf barn w/shop. Hist. period garden bldg. Asparagus, nut trees, orchard. 10 min. to C'town.

Beds:
3
Baths:
2 Full
Sq.Ft.:
n/a
Status:
Active
MLS#:
1000038727
Type:
Other
Subdivision:
00
Lot size:
1.79 Acres
Year built:
1951
Courtesy: Gunther-McClary Real Estate
View additional info

A spectacular waterfront location just outside of historic Chestertown providing privacy but not isolation, a blend of lawn and mature shade trees, over 200 feet of waterfrontage, private dock with a boat lift, beach, sunsets and is improved by a three bedroom home with a screened porch overlooking the water, hardwood floors, views of the river from almost every room.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
1000039085
Type:
Other
Subdivision:
Royston Shores
Lot size:
0.43 Acres
Year built:
1986
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Enjoy all the Chester River has to offer from this beautiful waterfront home. Two levels of decks and screened in porch overlook the dock and farmland beyond. The house has many recent upgrades including new kitchen,cork floors and systems. Master bedroom is on first floor with two huge bedrooms upstairs. Sit back and relax in the family room facing the water and watch the abundant wildlife.

Beds:
5
Baths:
4 Full
Sq.Ft.:
n/a
Status:
Active
MLS#:
1000083745
Type:
Other
Subdivision:
Historic Chestertown
Lot size:
0.42 Acres
Year built:
1877
Courtesy: Benson & Mangold, LLC
View additional info

A beautiful 1877c Victorian home in the heart of historic Chestertown. Currently operating as a B & B, this exemplary primary residence, welcomes you and your family. Offering a separate carriage house, two car garage, beautiful gardens & add'l lot., w/ ample parking. A short walk to the Chester River, Washington College, restaurants, shops and farmers market. Turn-Key business available.

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BRIGHT MLS - All information, regardless of source, should be verified by personal inspection by and/or with the appropriate professional(s). The information is not guaranteed. Measurements are solely for the purpose of marketing, may not be exact, and should not be relied upon for loan, valuation, or other purposes.