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Chestertown MD Real Estate & Homes for Sale

126 Properties Found

The median home value in Chestertown, MD is $256,500. This is higher than the county median home value of $200,000. The national median home value is $209,892. The average price of homes sold in Chestertown, MD is $256,500. Approximately 43% of Chestertown homes are owned, compared to 42% rented, while 15% are vacant. Chestertown real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you like to see a property, contact Chestertown real estate agent to arrange a tour today!
Learn more about Chestertown Real Estate.


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1–25 of 126 properties displayed
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Beds:
5
Baths:
3 Full/2 Half
Sq.Ft.:
5,174
Status:
Active
MLS#:
1000084191
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
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:
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:
5 Full/1 Half
Sq.Ft.:
5,250
Status:
Active
MLS#:
MDKE100016
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
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:
2 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE104742
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
168.77 Acres
Year built:
2002
Courtesy: Maryland Heritage Properties
View additional info

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:
2 Full
Sq.Ft.:
3,008
Status:
Active
MLS#:
MDKE115238
Type:
Single Family, Single Family-Detached
Subdivision:
Pomona
Lot size:
113 Acres
Year built:
1800
Courtesy: Coldwell Banker Residential Brokerage-Annapolis
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Hilltop Farm C. 1810 in historic Chestertown includes 113 acres with waterfront on Langford Creek off the Chester River. Property includes large 8 feet deep fresh water pond and impoundment.Perc test done in 2019 for new construction 3500 +sf on the waterfront portion of the farm to accommodate a new waterfront residence with privacy. Many options with the property operating as a residence, farm or combination. Great relationship with local farmer regarding crops and maintenance. This is a rare opportunity to own a piece of Eastern Shore history and build your dream home surrounded by wildlife on the shores of Langford Creek.

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:
4
Baths:
3 Full
Sq.Ft.:
4,715
Status:
Active
MLS#:
MDKE115392
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
2.06 Acres
Year built:
1995
Courtesy: Gunther-McClary Real Estate
View additional info

Enjoy sweeping water views from three sides of this spectacular property. The custom built sprawling ranch home offers first floor living, is ideally situated on a point of land that provides broad water views, a private dock with protected water and easy access to the Chesapeake Bay, mature shade trees and gardens, a large deck overlooking the water, a separate guest house that is located close to the main house but can not be seen from the main house and has a separate driveway. The furniture in the fully furnished guest house may be included in the sale. The total square footage of both houses is over 4,000 sq ft but the main house is just over 3,000 sq ft. This is a rare offering that one must see to truly appreciate all that it has to offer.

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 thru 2004 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:
4
Baths:
3 Full
Sq.Ft.:
4,358
Status:
Active
MLS#:
MDKE115462
Type:
Single Family, Single Family-Detached
Subdivision:
Great Oak Estates
Lot size:
1.36 Acres
Year built:
2005
Courtesy: Cross Street Realtors, LLC
View additional info

This exquisite Chesapeake Bay Waterfront home is the definition of perfection! Stunning panoramic sunsets and broad water views are yours from nearly every room. An incredible four season room with large picture windows and tile floors flows into the gourmet kitchen and open dining area. The kitchen features a six-burner Viking gas range and double oven, granite counters, custom wood cabinetry, and large island. A two-story living room with double-sided gas fireplace allows access to the waterside deck with elevated views. Some of the best views are reserved for the beautiful Master suite, offering vaulted ceilings, a private balcony, and a large Master bath with tiled shower enclosure, double vanity and luxurious soaking tub. Three additional bedrooms and two full baths provide ample space for guests. Rounding out the complete package is the sizeable finished basement with premium sound, flat screen and projector and game area, as well as an attached 3-car garage. Bold, elevated views, a private beach, privacy, and a long list of amenities make this property one of a kind!

Open House:

Saturday, 10/5 1:30-3:30PM

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:
2 Full
Sq.Ft.:
2,425
Status:
Active
MLS#:
MDKE115382
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester Estates
Lot size:
0.71 Acres
Year built:
2015
Courtesy: RE/MAX One
View additional info

From the time you enter this property, it exceeds all expectations. Custom built, designed by owner, no space is without purpose. Great entertainment areas, efficient, energy smart, wood & tile flooring, top of the line materials from the construction to the lighting fixtures. There is nothing like this home. And then, there are the incredible bay views! Mahogany front door, Ipe porch, Hardiplank siding, NANA WALL opens to bring the outside in... screens, remotely controlled. Room for a garage, plenty of parking, over sized hot tub with adjustable privacy walls and outside shower. Waterviews from almost every room, Master suite w/ huge walk in shower, whirlpool tub, full vanity wall, walk-in closet, outside balcony. Main level has extensive seating areas in great room for breakfast bistro, cocktails, dining, wine bar, coffee station, cocktail station, large porches and balcony. Cozy living room with propane fireplace. Kitchen w/ top of the line appliances, walk in pantry/mud room. The list is too long to cover. This is a must see! Don't miss a photo, it all tells a story.

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,504
Status:
Active
MLS#:
MDKE115596
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester Estates
Lot size:
0.85 Acres
Year built:
1937
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Eastern Shore Chesapeake Bay cottage with sweeping westerly views is set on 1.3 acres in Tolchester Estates. Built in 1930 and offering 200~ of waterfront with beach, the home captures stunning water views of the Chesapeake Bay. Tolchester Marina, a full service marina located just 1-mile away, has a private beach, restaurant, pool, and beach bar. Just 20 minutes away is downtown Chestertown set on the banks of the Chester River. The lovely walking town with 18th century homes offers a river walk, cafes, pubs, shops, theater and waterfront dining. Chestertown is also home to Washington College.

Beds:
5
Baths:
3 Full/1 Half
Sq.Ft.:
3,031
Status:
Active
MLS#:
MDKE115048
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
0.21 Acres
Year built:
1925
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

This stately colonial is located on the famed Water Street in the historic district of Chestertown. The home features 1 off street parking space and one on street parking space, high-end upgrades including Wolf appliances, Sub Zero refrigerator, Granite counters, Rinnai instant hot water, radiant floor heating in the kitchen, Generac whole house generator, Honeywell commercial dehumidifier in the basement, slate roof and extensive landscaping with a sprinkler system. The owners have done a great job preserving features from the original era. With the large flowing rooms downstairs and the added porches and patio, this home is perfect for entertaining. A classic Chestertown beauty! Call to schedule your showing today.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,106
Status:
NEW LISTING
MLS#:
MDKE115676
Type:
Single Family, Single Family-Detached
Subdivision:
Langford Bay Estates
Lot size:
1.35 Acres
Year built:
1949
Courtesy: Gunther-McClary Real Estate
View additional info

A diamond in the rough with nearly all the desired features for waterfront property. Broad expansive 180 degree southwesterly views of Langford creek, four season sunsets, protected dock and slip. Crabbing, fishing, wake boarding, water skiing, paddle boarding, sailing all in your back yard. Just a few minutes from historic downtown Chestertown and very easy access to points north, Philadelphia and Wilmington or south, Washington DC and Northern Virginia.

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
3,960
Status:
Active
MLS#:
MDKE114000
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
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 and new baths, while retaining the Victorian signatures of high ceilings, spacious rooms, fine wood floors, detailed wood trim, long windows, arched walls and graceful staircase. Rear and side gardens, 2 car detached garage with wine room and potting shed at the end of this Water St. driveway.

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
2,492
Status:
Active
MLS#:
MDKE100005
Type:
Single Family, Single Family-Detached
Subdivision:
Fannell's Meadow
Lot size:
10 Acres
Year built:
2006
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Eastern Shore Vermont style farmhouse built in 2006 is set on a rural 10-acre meadow backing up to woods. The farmland across the street is in conservation. This beautiful, thoughtfully designed home with two geo-thermal wells, high ceilings and large windows offers pastoral views of fields and woods, yet is surprisingly located just 5 minutes from the Chester River and Chestertown~s historic district. Maple hardwood floors, wood detail and a stunning Finnish Tulikivi soapstone wood stove create warm, bright interior spaces, while serene views from the screened porch and terrace invite outdoor living. Charming separate guest quarters, library, media room and a basement with large windows and high ceilings are among other desirable amenities. The property is also ideal for a horse farm. Founded in 1706, Chestertown is set on the banks of the Chester River where visitors and residents alike enjoy strolling along the brick walkways lined with 18th century homes, cafes, shops, live theater, river walk and waterfront dining. It is also home to Washington College, the Chester River Yacht and Country Club and Wilmer Park on the Chester River. Kent County also offers beaches, public landings, rails to trails for hiking and biking, the farmers market and Eastern Neck National Wildlife Refuge. Chestertown is located about 90-minutes from Washington and Philadelphia.

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
2,327
Status:
Active
MLS#:
1002400784
Type:
Single Family, Single Family-Detached
Subdivision:
Reba Anthony
Lot size:
1.9 Acres
Year built:
1990
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Premium materials and finishes,including yellow pine floors reclaimed from Camden Yards,really set this waterfront cape apart.Crown moulding,wainscoting,panel doors,fireplace,sun room and master on first floor are among the many amenities.Studio with AC/Heat is surrounded by a Williamsburg Garden and a gazebo sits waterside.Very private. Adjacent .44 perc approved lot can be purchased separately. Walk to C-town.

Open House:

Saturday, 9/21 10:00-2:00PM

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
4,138
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! Past garage turned into first floor master.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE115074
Type:
Single Family, Single Family-Detached
Subdivision:
Prestwick
Lot size:
1.18 Acres
Courtesy: Gunther-McClary Real Estate
View additional info

Spec home located in small 12 home development (to be built). Prestwick offers the best in eastern shore living with the small town charm of Chestertown, MD, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington, DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board or kayak at the new town marina or the many county owned ramps. Design and build the home you want with one of the area's finest builders

Beds:
4
Baths:
2 Full
Sq.Ft.:
1,820
Status:
Active
MLS#:
MDKE115076
Type:
Single Family, Single Family-Detached
Subdivision:
Fairlee Creek
Lot size:
5.05 Acres
Year built:
1988
Courtesy: Gunther-McClary Real Estate
View additional info

Best of all worlds in this waterfront home with easy water access and natural surroundings. Just feel the peace that engulfs you as you look out from the many windows of the great room. Boat, walk, bike, or drive to a marina, golf course, tennis, pool, restaurants and beach. A perfect Eastern Shore retreat. Co-broke commisssion will not be paid unless co-broke arranges and attends all showings

Beds:
3
Baths:
2 Full
Sq.Ft.:
2,928
Status:
Active
MLS#:
MDKE115054
Type:
Single Family, Single Family-Detached
Subdivision:
Country Club Estates
Lot size:
1.38 Acres
Year built:
1955
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Water views of the Chester River are a visual delight from this outstanding property on the Eastern Shore. Set on 1.3-acres in a highly-desirable residential area, the meticulously cared for home is just a walk away from Chester River Yacht & Country Club and is 1-mile from historic Chestertown. The open design creates generously sized, bright rooms with lovely views inviting outdoor living. Notable highlights such as wood detail, built in bookcases and a fireplace create a warm ambiance. The terrace overlooking gardens and the pond offers a serene setting, while the screened porch offers a lovely spot to enjoy the river views. Visitors and residents alike stroll around downtown Chestertown with its picturesque 18th century homes, brick walkways, Chester River Walk and marina. Enjoy the cafes, galleries, pubs, shops, live theater, farmers market, trails, First Friday, or take a river cruise on the Chester River Packet. There is a vibrant arts community and the town~s annual events include the Chestertown Tea Party, Harry Potter Festival and the Tall Ship Downrigging Weekend. Chestertown is home to Washington College and is located about 90-minutes from Washington and Philadelphia.

Beds:
3
Baths:
2 Full
Sq.Ft.:
2,138
Status:
Active
MLS#:
1001973778
Type:
Single Family, Single Family-Detached
Subdivision:
Long Cove Court
Lot size:
3.28 Acres
Year built:
1966
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Nature's paradise on Lovely Cove-enjoy a short and peaceful boat/kayak ride from your private dock to the East Fork of Langford Creek. This comfortable waterfront home celebrates 180 degrees water views, available from virtually all rooms. Outbuildings include garage area, workshop, storage, and potting shed. Over 3 1/4 acres of woods, cleared and privacy. Your own dock and 9 Ft. wide concrete launching ramp.

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