Kathy Christensen
410-924-4814

Chestertown MD Real Estate & Homes for Sale

127 Properties Found

The median home value in Chestertown, MD is $246,500. 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 $246,500. 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.


Sort Results:
1–25 of 127 properties displayed
Refine Property Search
Page 1 | 2 | 3 | 4 | 5 | 6 of 6    Prev | Next
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 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:
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:
3 Full/2 Half
Sq.Ft.:
2,656
Status:
Active
MLS#:
MDKE115298
Type:
Single Family, Single Family-Detached
Subdivision:
Quaker Neck
Lot size:
51.55 Acres
Year built:
1900
Courtesy: Cross Street Realtors LLC
View additional info

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:
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
View additional info

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:
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
View additional info

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:
NEW LISTING
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. 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:
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:
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/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:
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:
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. Pool table in basement will stay with the property.

Beds:
5
Baths:
3 Full/1 Half
Sq.Ft.:
4,866
Status:
Active
MLS#:
MDKE114924
Type:
Single Family, Single Family-Detached
Subdivision:
Great Oak Estates
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 Oak Community of Chestertown, MD! This 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. Motivated seller. Bring offer!

Beds:
5
Baths:
3 Full/1 Half
Sq.Ft.:
n/a
Status:
Active
MLS#:
1009688038
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
13.17 Acres
Year built:
2006
Courtesy: RE/MAX Executive
View additional info

OPEN 5/18, 12-2PM 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!

Beds:
4
Baths:
3 Full
Sq.Ft.:
2,182
Status:
Active
MLS#:
MDQA139824
Type:
Single Family, Single Family-Detached
Subdivision:
Sarah Skipper Lands
Lot size:
0.89 Acres
Year built:
1962
Courtesy: Berkshire Hathaway HomeServices PenFed Realty
View additional info

Enjoy the best of Chestertown waterfront living! This beautifully updated home nestles on the shoreline of the Chester River with breathtaking views across the bridge from historic Chestertown. Meticulously renovated in 2015, this property is open and airy with superior custom molding and craftsmanship to be seen in every room. Kitchen boasts stainless steel appliances with granite counters and ceramic tile floor. The Kitchen flows into the Dining Room with its custom built large wooden cabinet, hardwood floors, stunning decorative chandelier, and bay window. The Living Room offers soothing wood burning fireplace and hardwood floors. A large Sun Room stretching across the entire river side of the property with walls of Anderson sliding glass doors allows for abundant natural light and gorgeous water views. Perfect for entertaining! The side hallway leads to the main level master bedroom and offers custom shuttered windows, spacious closet, decorative ceiling fan, and hardwood floors leading into the luxurious private Owner's Bath. This custom ceramic tile oasis offers walk in shower surrounded by a glass enclosure, decorative mirror built into the wall overlooking large vanity, and wonderful storage. The other two spacious bedrooms on the main level boast hardwood floors, large closets along with custom built bookcases and plantation style shutters for the windows. The second main level full bath offers a custom ceramic tile walk in shower with bench and sliding glass enclosure. The steps ascending to the upper level lead to a Recreation Room/Office and another private suite complete with vaulted ceilings, large skylights and private full bathroom. The lower level has a full basement with a french drainage system, extra large cedar closet for storage, laundry area, and access to a deep one car garage that leads to the asphalt driveway. A BATS Septic installed in 2016, a nearly new deep water pier and private beach complete the offering. Don't miss out on this opportunity of a lifetime!

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:
3
Baths:
1 Full/1 Half
Sq.Ft.:
1,987
Status:
Active
MLS#:
MDQA139826
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
3.84 Acres
Year built:
1964
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Queen Anne's county waterfront over looking Chestertown. Perfect view of sunsets from this side. Enjoy the Chester river and private pond from this nearly 4 acre parcel. Upgrades include new kitchen, wiring, septic (BAT system), well, irrigation system, bulkheading, 100 ft dock complete with lift. Water and electric on the dock. Great crabbing from this location. Current owners ice skate on the pond in the winter.

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:
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.

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
2,906
Status:
Active
MLS#:
MDQA136898
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
1.7 Acres
Year built:
1958
Courtesy: Coldwell Banker Residential Brokerage-Annapolis
View additional info

Just Reduced $50,000! Minutes from Chestertown, shops, Washington College, restaurants and cultural events. One level living on the Chester River on one and a half acres. Private dock and a nice sandy beach - you will feel like you are on vacation every day. Waterviews from almost every room and the most amazing sunsets. LARGE screened-in porch and decks. Large kitchen and pantry with lots of storage. Three car garage and workshop. Whole house generator. Perfect second home with a separate wing for your guests. Welcome home to the Eastern Shore of Maryland.

Beds:
4
Baths:
4 Full
Sq.Ft.:
3,257
Status:
Active
MLS#:
MDKE114830
Type:
Single Family, Single Family-Detached
Subdivision:
Country Club Estates
Lot size:
0.92 Acres
Year built:
1969
Courtesy: Cross Street Realtors LLC
View additional info

This magnificent residence is situated just off the 13th hole. If you like to golf, the convenience of accessing the course doesn't get much better! Expansive views over the Chester River Yacht & Country Club Golf Course to the Chester River are certainly appreciated. Two main level master suites, gourmet kit, wet bar, great room, den/bedroom, and sizeable laundry room just off of the mud-room complete the interior of the home... The breezeway connects the spacious 2-car garage with epoxy flooring, and finished 2nd level to the home, which comes in handy when the weather is not cooperating! Generous custom storage capacity & an abundance of built-ins will impress any Buyer in need of extra space. This precious gem is not going to last long.

Refine Property Search
Page 1 | 2 | 3 | 4 | 5 | 6 of 6    Prev | Next
1–25 of 127 properties displayed