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Rock Hall Properties Real Estate
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Chestertown MD Real Estate & Homes for Sale

106 Properties Found


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1–25 of 106 properties displayed
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Beds:
5
Baths:
5 Full/1 Half
Sq.Ft.:
10,870
Status:
Active
MLS#:
1009942958
Type:
Single Family, 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:
5 Full/1 Half
Sq.Ft.:
10,870
Status:
Active
MLS#:
1000346718
Type:
Single Family, 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 over 50 years, is a once-in-a-lifetime waterfront and hunting farm. The 9,600 square foot, seven bedroom Main Home is situated within feet of the Chester River. With three master suites, an in-law suite, and ample room to relax... the sweeping River views from every room are breathtaking. The 420 foot dock has eight feet MLW, water & electric, and six (or more!) slips. The large, insulated, and heated boathouse has a 150 foot private railway launch. With over 3,000 feet of River frontage and over 1,400 feet of stone revetment, the waterfront is quite literally just outside the door. Of the total 164.13 acres, 96 are tillable, 43 are wooded, and the farmland boasts three ponds. The four bedroom, two and a half bathroom Farm Home was built in the early 1900s and renovated with major upgrades in 1994. The original farm barn and silo stand proudly near the entrance of the property. The exquisite and prestigious Quaker Neck locale is nothing short of spectacular.

Beds:
7
Baths:
7 Full/2 Half
Sq.Ft.:
9,651
Status:
Active
MLS#:
1002149830
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 over 50 years, is a once-in-a-lifetime waterfront and hunting farm. The 9,600 square foot, seven bedroom Main Home is situated within feet of the Chester River. With three master suites, an in-law suite, and ample room to relax... the sweeping River views from every room are breathtaking. The 420 foot dock has eight feet MLW, water & electric, and six (or more!) slips. The large, insulated, and heated boathouse has a 150 foot private railway launch. With over 3,000 feet of River frontage and over 1,400 feet of stone revetment, the waterfront is quite literally just outside the door. Of the total 164.13 acres, 96 are tillable, 43 are wooded, and the farmland boasts three ponds. The four bedroom, two and a half bathroom Farm Home was built in the early 1900s and renovated with major upgrades in 1994. The original farm barn and silo stand proudly near the entrance of the property. The exquisite and prestigious Quaker Neck locale is nothing short of spectacular.

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:
5
Baths:
5 Full/1 Half
Sq.Ft.:
5,190
Status:
Active
MLS#:
MDKE100018
Type:
Single Family, Single Family-Detached
Subdivision:
None
Lot size:
76.07 Acres
Year built:
1800
Courtesy: Brandywine Fine Properties Sot
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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 flr MBR suite, a new 3BR tenant house, dock with lift & an in-ground pool. A 3rd home may be built to create a family compound. Enjoy the peace and serenity of Eastern Shore outdoor Life. Agent/Owner.

Beds:
4
Baths:
5 Full
Sq.Ft.:
5,250
Status:
Active
MLS#:
MDKE100016
Type:
Single Family, Single Family-Detached
Subdivision:
None
Lot size:
76.07 Acres
Year built:
1781
Courtesy: Brandywine Fine Properties
View additional info

Owners will be creative in financing this1781 Eastern Shore beauty fully 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. Perfect for todays lifestyle enjoying peaceful Eastern Shore outdoor life in a vibrant college town. Owner is Licensed Real Estate Agent.

Beds:
4
Baths:
3 Full/2 Half
Sq.Ft.:
2,656
Status:
Active
MLS#:
1002273018
Type:
Single Family, 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:
4
Baths:
2 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE104742
Type:
Single Family, Single Family-Detached
Subdivision:
Pentridge Farms
Lot size:
168.77 Acres
Year built:
2002
Courtesy: Maryland Heritage Properties
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Rarely do you find a true contemporary residence in this traditional area in Kent County on Maryland's Eastern Shore. This architecturally designed house is surrounded by 168 private acres of open fields, virgin woods & ponds. The 3000+ square footage includes soaring beamed ceilings, open kitchen/living area, wood floors, soap stone counters, gourmet kitchen. An exotic European style "woodstove" (far from your ordinary woodstove - see photos) dominates the outstanding design. Multiple French door & casement windows flow to a 700 sq. ft. deck & 1700 slate A& brick patio. A handsome pergola completes the design of the groundsAn exciting contemporary post & beam guest house shares the acreage and is located a private distance away. The open interior design, exposed beamed ceilings & decking compliments the main house design. Pastoral views and farms abound.

Beds:
5
Baths:
4 Full/1 Half
Sq.Ft.:
4,748
Status:
Active
MLS#:
1000084003
Type:
Single Family, 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. .

Beds:
3
Baths:
3 Full
Sq.Ft.:
2,236
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
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/2 Half
Sq.Ft.:
3,848
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:
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:
4
Baths:
4 Full/1 Half
Sq.Ft.:
4,133
Status:
Active
MLS#:
MDKE114086
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester Estates
Lot size:
1.1 Acres
Year built:
1959
Courtesy: Cross Street Realtors LLC
View additional info

Expansive frontage on the Bay. Private, end of road lot. Large fenced pool with breathtaking bay view. House completely renovated in 2002 including infrastructure. 1st and 2nd floor Master Suites. Open den/study on second floor. Maintained steps and deck down to the water. Stone wood burning fireplace makes open living room extra cozy. Mature landscaping including vegetable garden. And of course spectacular bay views from every room. Separate artist studio and garden shed near pool. First floor master has private screened porch. Second floor master has private deck, coffee bar, gas fireplace and whirlpool bath.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,584
Status:
Active
MLS#:
MDKE110432
Type:
Other
Subdivision:
000
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:
2 Full/1 Half
Sq.Ft.:
3,440
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:
4
Baths:
3 Full/1 Half
Sq.Ft.:
2,934
Status:
Active
MLS#:
1001986560
Type:
Single Family, 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:
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:
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:
5
Baths:
3 Full/1 Half
Sq.Ft.:
4,866
Status:
NEW LISTING
MLS#:
MDKE114924
Type:
Single Family, Single Family-Detached
Subdivision:
Great Oak Estate
Lot size:
1.36 Acres
Year built:
1997
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Custom built water front 5 bedroom 3.5 bath dream house in Great Oaks Community of Chestertown, MD! This +/- 5000 sq ft property is perfectly situated on an elevated bluff with absolutely breath taken water views and sunsets from almost every room in the house! The shoreline is protected by 150 ft of rip rap along with nice elevation. Pride of ownership is obvious as you walk thru this meticulously maintained estate. Features include 9 ft Ceilings, gourmet kitchen with luxury viking appliances, chef cutting board counter top with breakfast bar area, hardwood floors throughout majority of the main floor. The open floor plan has the kitchen area flowing into the great room that boasts a grand floor to ceiling, brick wood burning fireplace and a vaulted, shiplap pine ceiling with exposed beams. Nearby is an elegant formal dining room, and large gathering room, additional casual dining area with gas fireplace! The rest of the first floor is devoted to a master suite, walk in closet, master bath with tiled floor, corner soaking tub, and double sinks! And, two additional bedrooms and another full bathroom, and a laundry room. The 2nd floor includes two spacious bedrooms, a large living room area, full bathroom and an unfinished bonus room/or possible 6th bedroom (18x22~) with separate stair case to egress to the garage or outside. The property has an oversized two car garage with work bench area! One of the special features of the property is the basement has been turned into a state-of-the-art wine cellar with temperature/humidity controlled environment! A very special feature of the house is the grand screened in porch w/3 ceiling fans that spans the length of the majority of the house with panoramic views of the cheasapeake bay. In addition there is a large hot tub, upgraded Culligan whole house water filter, and two hot water heaters. This is a must see estate with a great waterside setting on a dead end street.

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:
Active
MLS#:
1009688038
Type:
Single Family, Single Family-Detached
Subdivision:
None
Lot size:
13.17 Acres
Year built:
2006
Courtesy: RE/MAX Executive
View additional info

AMAZING CUSTOM-BUILT ESTATE sited on almost 14 acres w/stream & Every luxury & upgrade + 2500 sf basement. First floor master, 4 addtnl Brs, Phenomenal kitchen includes 3 ovens, double dishwasher, granite counters, custom Amish lighted, glass cab., custom tile floors, double sinks + veg sink, conv. micro, table space, serving counter, desk area. STUNNING wall of glass & two-story brick FIREPLACE in open family room w/balcony overlook. HUGE screened porch w/vaulted ceiling & brick floor. Amazing brick front porch w/entertainment area to capture every country view! IT'S WORTH A LOOK; YOU'LL FALL IN LOVE!

Open House:

Saturday, 5/11 12:00-2:00PM

Beds:
5
Baths:
3 Full/1 Half
Sq.Ft.:
5,367
Status:
Active
MLS#:
1002024942
Type:
Single Family, Single Family-Detached
Subdivision:
Gorgeous & A Must See! Like New!!
Lot size:
13.17 Acres
Year built:
2006
Courtesy: RE/MAX Executive
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 including a stream-Hurry!

Open House:

Saturday, 4/27 11:00-1:00PM

Beds:
5
Baths:
3 Full/1 Half
Sq.Ft.:
5,563
Status:
Active
MLS#:
1009997800
Type:
Single Family, Single Family-Detached
Subdivision:
21 Private Acres
Lot size:
21.06 Acres
Year built:
2005
Courtesy: Chaney Homes, LLC
View additional info

Over 21 Acres Ready for your Horses & Existing Vineyard- Possible B&B! Entertainer's Delight- Nearly 5600 sq ft, 5 Bedrooms, 3.5 Baths. In-Ground Pool, Large Patio. Fenced Pasture. Large Outbuilding with 2 Stalls, Main-Level Master Suite w/ ADDITIONAL Potential In-Law Bedroom/Rec Room w/ Access to 1/2 Bath & Washer/Dryer, 3- Car Side-Load Garage,. 3 LARGE upper-level Bedrooms!

Beds:
5
Baths:
3 Full/1 Half
Sq.Ft.:
5,563
Status:
Active
MLS#:
1002071386
Type:
Single Family, Single Family-Detached
Subdivision:
21 Private Acres
Lot size:
21.06 Acres
Year built:
2005
Courtesy: Chaney Homes, LLC
View additional info
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1–25 of 106 properties displayed