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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.:
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
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:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,498
Status:
NEW LISTING
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:
2 Full
Sq.Ft.:
n/a
Status:
Active
MLS#:
1000083629
Type:
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 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
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:
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:
4
Baths:
3 Full/1 Half
Sq.Ft.:
2,940
Status:
Active
MLS#:
1003269273
Type:
Single Family, Single Family-Detached
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:
5
Baths:
3 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
1000135450
Type:
Single Family
Subdivision:
Langford Farm
Lot size:
4.42 Acres
Year built:
1998
Courtesy: Cross Street Realtors LLC
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Custom water front with the greatest of great rooms, accented by reclaimed VT barn hardwood floors and wood burning fireplace. Well designed kitchen opens onto main living and entertainment space, office and laundry nearby. First floor master bedroom and bath with both tub and walk in shower. Sweeping lawn to generous waterfront which includes a pier with boat lift, 4+MLW. Room for a pool too!

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 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:
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:
NEW LISTING
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:
3 Full/1 Half
Sq.Ft.:
4,086
Status:
Active
MLS#:
1000083781
Type:
Single Family
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:
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:
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!

Beds:
6
Baths:
6 Full
Sq.Ft.:
n/a
Status:
Active
MLS#:
1000084105
Type:
Single Family, Single Family-Detached
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:
2 Full
Sq.Ft.:
n/a
Status:
Active
MLS#:
1000038727
Type:
Single Family
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:
5
Baths:
3 Full/1 Half
Sq.Ft.:
2,761
Status:
Active
MLS#:
1000267824
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester Estates
Lot size:
0.55 Acres
Year built:
1957
Courtesy: Cross Street Realtors LLC
View additional info

Recipe for "that" exceptional eastern shore retreat: invite expansive views of the Chesapeake through large window panes that border an elegant open plan design, add Brazilian Cherry wood floors and a gourmet kitchen, fill the home with an abundance of natural light to balance a distinguished paint scheme and package with 4 zones to impress the astute energy conscious Buyer!

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:
3
Baths:
2 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
1000278816
Type:
Townhouse
Subdivision:
Chester River Landing
Lot size:
0.03 Acres
Year built:
2018
Courtesy: Cross Street Realtors LLC
View additional info

Waterfront Townhome TO BE BUILT! The home boasts hardwood floors, granite counter tops, high end appliances, fireplace, spacious master suite, home office or den... plus more! Chester River Landing offers a private beach, walking paths, floating docks, pool with bath house, riverside fire pit and picnic area with grill. Bring your boat!

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