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Chestertown MD Real Estate & Homes for Sale

32 Properties Found

The median home value in Chestertown, MD is $269,990. This is higher than the county median home value of $249,900. The national median home value is $308,980. The average price of homes sold in Chestertown, MD is $269,990. Approximately 44% of Chestertown homes are owned, compared to 42% rented, while 14% 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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Beds:
2
Baths:
1 Full
Sq.Ft.:
1,232
Status:
NEW LISTING
MLS#:
MDKE2003862
Type:
Townhouse
Subdivision:
Tolchester
Lot size:
0.05 Acres
Year built:
1955
Courtesy: Chesapeake Real Estate Associates, LLC
View additional info

Welcome home to Tolchester Village. This 2 bedroom 1 bathroom townhome is short distance to Rock Hall or Chestertown. This efficient townhome offers a tranquil setting with an abundance of wildlife in a park like setting just of the back patio area for entertaining. Plenty of parking in this 18 unit community. Seller is offering 4k towards buyers closing costs for choice of carpet / paint.

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,056
Status:
NEW LISTING
MLS#:
MDQA2009396
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.34 Acres
Year built:
1974
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Cute and compact 3 bed, 1 bath rancher in Chester Harbor. Just minutes outside town on the Queen Anne's County side of Chestertown. Fully fenced backyard. Roof is 1 year old. Reverse osmosis system. Queen Anne's County schools. 3rd bedroom was not photographed as seller is storing boxes in that room. Property is being sold as is.

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
4,730
Status:
NEW LISTING
MLS#:
MDKE2003814
Type:
Single Family, Single Family-Detached
Subdivision:
Country Club Estates
Lot size:
0.61 Acres
Year built:
2011
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

This circa 2011, white brick house was built to celebrate the expansive views over the Chester River Yacht &Country Club golf course to the Chester River. There is an attractive patio at one end and a screened porch off the owner's suite. The landscaping around the circular driveway is lovely; the garage is set on an angle as to be unobtrusive from the road and the house entrance. Inside, all the rooms enjoy the views; the glassed in sun room being the most spectacular. Beautiful flooring, oversize crown molding, chair rails, accent & recessed lighting and painted paneling throughout. New A/C handler, Rinnai system with boosters (to reach around this 4,000+ sq. ft. house), foam insulation underground and up the walls, crawl space encapsulated, 3 temperature zones and audio wired surround sound. The kitchen and owner's suite are too great to try to describe, for instance, the marble came directly from Italy and no longer available. Laundry and "mud kitchen" are between the owner's suite and garage. Take a golf cart to the club, ride a bike into town or just sit and watch the tall ships go by.

Beds:
2
Baths:
2 Full
Sq.Ft.:
864
Status:
NEW LISTING
MLS#:
MDQA2009482
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
0.5 Acres
Year built:
1930
Courtesy: Village Real Estate Company LLC
View additional info

Wonderful renovation, modern, efficient, and move in ready! Home features vaulted ceilings with open flexible floorplan and 2 brand new luxury bathrooms. Energy efficient instant hot water heater. Large side deck, plenty of parking, small storage shed, and updated BAT system septic. Spacious yard for a garden and family events. Can't pass up this AFFORDABLE price point for like new construction, but not a townhouse!

Beds:
2
Baths:
1 Full
Sq.Ft.:
729
Status:
Active
MLS#:
MDKE2003730
Type:
Condo
Subdivision:
Chestertown Historic District
Year built:
1886
Courtesy: Gunther-McClary Real Estate
View additional info

A stately 1800âs waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own ground level storage. This is a unique setting offering waterfront living in downtown historic Chestertown and includes off street parking. Walk to downtown restaurants and shops. Beautiful southeast views of the Chester River with spectacular sunrises and plenty of year-round sunshine. Take in the all of the nearly year-round waterfront activities from your own back yard, including Chestertown Tea Party, 4th of July fireworks and Sultana down rigging weekend. Located on Marylandâs scenic eastern shore less than 85 miles from Washington DC to the south or Philadelphia to the north, this home is the perfect meeting spot for those living in the Mid-Atlantic region. This unit offers a 2 Bed 1 bath has a brand new kitchen and upgraded bathroom along with broad southeast river views.

Beds:
1
Baths:
1 Full
Sq.Ft.:
850
Status:
Active
MLS#:
MDKE2003732
Type:
Condo
Subdivision:
Chestertown Historic District
Year built:
1886
Courtesy: Gunther-McClary Real Estate
View additional info

A stately 1800âs waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own ground level storage. This is a unique setting offering waterfront living in downtown historic Chestertown and includes off street parking. Walk to downtown restaurants and shops. Beautiful southeast views of the Chester River with spectacular sunrises and plenty of year-round sunshine. Take in the all of the nearly year-round waterfront activities from your own back yard, including Chestertown Tea Party, 4th of July fireworks and Sultana down rigging weekend. Located on Marylandâs scenic eastern shore less than 85 miles from Washington DC to the south or Philadelphia to the north, this home is the perfect meeting spot for those living in the Mid-Atlantic region. This unit offers a 1 Bed 1 bath has a brand new kitchen, with island, and upgraded bathroom along with up and down river views.

Beds:
2
Baths:
1 Full
Sq.Ft.:
787
Status:
Active
MLS#:
MDKE2003742
Type:
Condo
Subdivision:
Chestertown Historic District
Year built:
1886
Courtesy: Gunther-McClary Real Estate
View additional info

A stately 1800âs waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own ground level storage. This is a unique setting offering waterfront living in downtown historic Chestertown and includes off street parking. Walk to downtown restaurants and shops. Beautiful southeast views of the Chester River with spectacular sunrises and plenty of year-round sunshine. Take in the all of the nearly year-round waterfront activities from your own back yard, including Chestertown Tea Party, 4th of July fireworks and Sultana down rigging weekend. Located on Marylandâs scenic eastern shore less than 85 miles from Washington DC to the south or Philadelphia to the north, this home is the perfect meeting spot for those living in the Mid-Atlantic region. This unit offers a 2 Bed 1 bath has a brand new kitchen, with island and upgraded bathroom along with up and down river views.

Beds:
1
Baths:
1 Full
Sq.Ft.:
652
Status:
Active
MLS#:
MDKE2003722
Type:
Condo
Subdivision:
Chestertown Historic District
Year built:
1886
Courtesy: Gunther-McClary Real Estate
View additional info

A stately 1800âs waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own ground level storage. This is a unique setting offering waterfront living in downtown historic Chestertown and includes off street parking. Walk to downtown restaurants and shops. Beautiful southeast views of the Chester River with spectacular sunrises and plenty of year-round sunshine. Take in the all of the nearly year-round waterfront activities from your own back yard, including Chestertown Tea Party, 4th of July fireworks and Sultana down rigging weekend. Located on Marylandâs scenic eastern shore less than 85 miles from Washington DC to the south or Philadelphia to the north, this home is the perfect meeting spot for those living in the Mid-Atlantic region. This unit offers a 1 Bed 1 bath has a brand new kitchen, with island, and upgraded bathroom along with up and down river views.

Beds:
4
Baths:
2 Full
Sq.Ft.:
1,660
Status:
Active
MLS#:
MDKE2003760
Type:
Single Family, Single Family-Detached
Subdivision:
Quaker Neck
Lot size:
1.25 Acres
Year built:
1945
Courtesy: Gunther-McClary Real Estate
View additional info

Beautifully renovated waterfront on the Chester River, located between historic downtown Chestertown and the Chester River Yacht and Country Club. Renovations include including new kitchen and bathrooms. This property boasts a deep water dock with lift for your boating, swimming and fishing pleasures. Come and enjoy all the Chestertown has to offer with just a short walk to down town shops, restaurants and parks..

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,560
Status:
Active
MLS#:
MDQA2009320
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.34 Acres
Year built:
2002
Courtesy: Berkshire Hathaway Homeservice Homesale Realty, (800) 383-3535
View additional info

Look no more. This home is cute as a button and packs a ton of recent upgrades. . Starting from the top down: New roof, updated heating, hot water heater, wood flooring, kitchen counters, primary bathroom, encapsulated crawl space. This home is move in ready and has so much to offer. Great floor plan, covered front porch, fenced rear yard ready for pets, gardens, fire pits. The home is close to Chestertown has easy access to DE shopping, and is close to all that the area has to offer. Voluntary HOA $25/ year(Shopping, Farmer's Market, Chester River, The list goes On and On). Shed is "As IS" Stay tuned. OPEN HOUSE SAT 6th 12- 2PM

Beds:
3
Baths:
3 Full/1 Half
Sq.Ft.:
4,804
Status:
Active
MLS#:
MDQA2009012
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
9.58 Acres
Year built:
2010
Courtesy: TTR Sotheby's International Realty, (410) 673-3344
View additional info

Every so often a property like 240 Round Top Landing Road, Chestertown hits the market that checks all the boxes. This Chester River waterfront estate is situated on 10 acres , offering deep water, pier, 25' x 50 ' in-ground pool, screened porch , 3 bedroom/3.5 bath main house and a carriage house. The architectural design and the superb craftsmanship are evident as soon as you enter the driveway. Beautiful trees(Peach,Pear, Pines, Poplars, Sycamores, Magnolias' Crepe Myrtles) enhance the park-like setting. Notable features are geo-thermal heat; gas and wood burning fireplaces, chef's kitchen; first floor spacious primary bedroom suite , and open living areas. As far as the exterior, the stucco siding is either over brick or block so no stucco is over frame. Some poplar siding on main house and cedar siding on carriage house.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,512
Status:
Active
MLS#:
MDQA2009262
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
0.39 Acres
Year built:
2024
Courtesy: Cross Street Realtors LLC, 4434803453
View additional info

New construction, almost done! Updated pictures coming soon!! Anticipated completion May 1st. This 3-bedroom, 2.5-bathroom Cape Cod boasts water views of the Chester River. Featuring an open-concept layout, stainless steel appliances, and a main-level master with walk-in closet, and ensuite. Upstairs, discover two generously sized bedrooms accompanied by an additional full bathroom. Located at the end of a quiet, private street. *Current interior photos are of another home built by the same builder - for informational purposes only*

Beds:
5
Baths:
4 Full/1 Half
Sq.Ft.:
6,459
Status:
Active
MLS#:
MDKE2003704
Type:
Single Family, Single Family-Detached
Subdivision:
Fairgale Properties
Lot size:
3.95 Acres
Year built:
2000
Courtesy: Doug Ashley Realtors, LLC
View additional info

Step into a world of timeless elegance and tranquility with this meticulously maintained retreat. As you turn into the Fairgale Subdivision, it feels as though you are entering an estate, with majestic trees lining both sides of the paved road, creating a sense of grandeur and privacy. Nestled on the shores of an oversized pond, this exquisite home offers not only stunning views but also exclusive access to a community dock and dedicated boat slip onto Fairlee Creek. Originally built in 2000 and impeccably maintained and updated, this home welcomes you with a beautifully designed foyer that sets the bar for living beautifully. The living room, open to a gracious dining area, exudes warmth and hospitality, making it the perfect setting for gatherings with loved ones. French doors beckon you to the covered patio, where you can bask in the serene ambiance and enjoy the sights and sounds of nature. Below, the guinite pool invites you to relax and unwind, surrounded by ample space for poolside lounging and entertaining. The main level boasts four bedrooms, including a luxurious owner's suite complete with a cozy gas fireplace and direct access to the pool area. The master bath is a sanctuary in itself, featuring separate vanities, a spacious walk-in shower, a soothing soaking tub, and generous storage space. The second bathroom, versatile in its design, offers built-in bookshelves and two closets, making it ideal for use as an office or guest suite. A convenient half bath, with access to the pool, adds to the home's functionality and convenience. The recently updated kitchen is a Cook's delight, equipped with an island, ample storage, and all the necessary appliances. Adjacent to the kitchen, the family room beckons with built-ins, a fireplace, and abundant natural light, creating a cozy yet inviting atmosphere. The Florida Room, bathed in sunlight, offers a perfect spot for plants and relaxation, with seamless access to the pool area. Two additional bedrooms, one with an attached sitting room, and a full bath complete the main level, ensuring comfort and convenience for all. Downstairs, a newly added bedroom and bathroom, along with a spacious great room, provide endless possibilities for entertainment and recreation. The expansive storage room offers potential for additional living space or customization to suit your needs. Upstairs, the attic boasts a large cedar room for storage, with even more space available if needed. The quality of construction is evident throughout, ensuring durability and longevity for years to come. Don't miss this opportunity to experience the beauty and serenity of waterfront living at its finest. Schedule a viewing today and make this exquisite property your own slice of paradise in this great neighborhood.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,344
Status:
Active
MLS#:
MDKE2003724
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
3.47 Acres
Year built:
1990
Courtesy: Taylor Properties
View additional info

Wow - Big Price Change - Hurry! Enjoy over 3 acres to play, hunt, ride 4 wheelers, have horses, chickens & more. Owner has wonderfully updated almost everything about this house and there is home warranty for peace of mind. Relax in the morning on the front porch and watch nature from every window. Gorgeous spacious kitchen with granite counters and including an eat in one that will seat at least four. All brand new appliances convey including washer and dryer. Cozy up by the wood burning fireplace or explore your little piece of heaven. This property used to be 2 lots and county says its zoned for several lots that can be potentially taken off. Explore the possibilities. Shown by Appointment only. OWNER WILL CONSIDER ALL REASONALBE OFFERS!

Beds:
3
Baths:
2 Full
Sq.Ft.:
2,248
Status:
Active
MLS#:
MDQA2009140
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
15 Acres
Year built:
1985
Courtesy: Berkshire Hathaway Homeservice Homesale Realty, (800) 383-3535
View additional info

Price Reductions!!! This deal just got a good bit sweeter...Escape to the Country! This home is perfect for the outdoor enthusiast. Bring the horses, dogs, chickens, hunters, hobbyist,...you name it. 15 acres, with small pond and open areas for your animals, sports field, fire pit or huge gardens. Chicken coop, air rifle only shooting range, basketball court, wooded acreage with walking or biking trail and hunting possible all part of what makes this place a dream come true. In the home enjoy large family room with propane fireplace, beautiful kitchen with stainless steel appliances and granite counters. Custom cabinets and built-ins, wood, laminate, and tile floors throughout. Entry level and second level bedrooms. Ready to relax head to the screened porch for quiet evenings. Hot tub hookup in place. Shed and outbuilding provide endless hobby, farm, or craft options. The 30 x 36 metal building has a large open space with multiple smaller rooms with electric and heat. Working at home? Talkie WiFi is available. RV hook-up at both the house and the outbuilding. Underground dog fence and 2 collars will stay . Metal building is in good shape but being sold âas isâ. Abandoned underground oil tank on site. This type of property does not often come to market. DONT MISS IT! Home is on a shared R-O-W. No drive-bys. Pets on site so please provide as much notice for showings as possible.

Beds:
2
Baths:
1 Full
Sq.Ft.:
1,408
Status:
Active
MLS#:
MDQA2009122
Type:
Single Family, Single Family-Detached
Subdivision:
Queen Annes County
Lot size:
0.69 Acres
Year built:
1900
Courtesy: Blackwell Real Estate, LLC, (443) 221-4120
View additional info

Well maintained 2 bedroom 1 bath Colonial on .69 acres with winter water views of Fishing Creek! Features Include: Screened Porch * 1-Car Attached Garage * Tilt-in Insulated Double Pane Windows * Large Living / Dining Room Combo with Brick Accented Gas Fireplace * Updated Kitchen with Stainless Steel Appliances * Separate Laundry Room off Kitchen * 2 Generous Sized Upper Level Bedrooms + a Large Bathroom with Separate Make-Up Table. * Dual Zone Central Air, Dual Zone Hot Water Baseboard Heat * Full RV Hookup with Water, Sewer & Electric in Back Yard. *As Per 2021 Listing, 2011 BAT System Upgrade Allows For The Addition of a 3rd Bedroom* Conveniently located just minutes from all the shops and restaurants Chestertown has to offer, this quaint property offers a little rural lifestyle without the isolation!

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,128
Status:
Active
MLS#:
MDQA2008806
Type:
Single Family, Single Family-Detached
Subdivision:
Char Nor Manor
Lot size:
0.2 Acres
Year built:
1954
Courtesy: Taylor Properties
View additional info

NEW PICTURES! Welcome to this cozy 3 bedroom, 1 bath completely remodeled home with views of the Chester River and a lovely yard full of mature gardens. New heating/air conditioning mini splits, new siding, windows and doors. New electric tankless hot water heater, new washer & dryer, LVP floors, new carpet, new stainless-steel appliances, fresh paint, plantation shutters and new window treatments throughout, electric with solar panels to help absorb energy costs. New front steps, seamless gutters and new lighting. Located in Queen Anne's County, Chestertown MD on a dead-end dirt road. Home has a 12 x 16 treated lumber deck at rear entry and a 10 x 12 shed matching siding, new windows, and new tin roof Enjoy peaceful days and night as this home is located on a no outlet dirt road. The yard is abundant with flowering trees, shrubs and flowers to enjoy your morning coffee or evening sunsets. Annual events include the Chestertown Tea Party and Tall Ship Down Rigging Weekend. Residents and visitors alike enjoy the vibrant arts community, restaurants, shopping, the Saturday Farmers/Artisan Market, parks, rails-to-trails and water activities. Just 25 minutes to the Bay bridge or Middletown, De. Must See!

Beds:
2
Baths:
2 Full/1 Half
Sq.Ft.:
2,210
Status:
Active
MLS#:
MDKE2003556
Type:
Single Family, Single Family-Detached
Subdivision:
Orchard Hill
Lot size:
1.89 Acres
Year built:
1992
Courtesy: Chesapeake Real Estate Associates, LLC
View additional info

Welcome to your tranquil retreat at Orchard Hill, where modern sophistication meets peaceful living on 1.89 acres of beautifully landscaped grounds. This stunning Cape Cod style home offers an abundance of amenities and thoughtful details throughout. As you step inside, you're greeted by the grandeur of vaulted ceilings that create an open and airy atmosphere. The ground floor primary bedroom provides convenience and luxury, complete with a upgraded kitchen featuring granite countertops, quality stainless steel appliances, an island with a gas cooktop, and a built-in wine refrigerator. The primary bedroom is a true sanctuary, featuring a luxury primary bath with a jetted tub and a stylish tile shower with glass doors. The main level's open layout is perfect for entertaining, with the added convenience of a bar with a sink. The second floor offers a guest bedroom, a full bath, and a loft that could easily be converted into a third bedroom or utilized as a versatile space according to your needs. Outdoor living is equally impressive, with a screened porch, large composite deck with a retractable canopy, a gazebo, and beautiful English cottage gardens featuring many native plants. The expansive outdoor space is perfect for gardening, outdoor activities, or simply enjoying the serene surroundings. Backing to trees and farmland, this property provides a peaceful backdrop and ample privacy. It's truly a must-see for those seeking a blend of modern luxury and peaceful countryside living. Schedule a showing today to experience the beauty and serenity of this exceptional property at Orchard Hill.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,296
Status:
Active
MLS#:
MDQA2008894
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.69 Acres
Year built:
1976
Courtesy: The Hogans Agency, (410) 778-1665
View additional info

Be sure to check out the photos - this home has real charm and character! This well-maintained house has been home to the same family since 1975: blacktopped driveway resealed in 2022, new roof 2017, new well 2016, quarterly Pest Service and mature landscaping with a fenced backyard. New washer and dryer and a full tank of propane for use of the attractive oak fireplace. Both bathrooms completely updated 2024. Both large upstairs bedrooms have double windows which allow for maximum light during the day. The property sits on four lots for a total of .69 acres. The quiet community of Chester Harbor has a voluntary HOA which allows for Chester River water access and use of the community area located at the end of Fairview Drive. Round Top Park is close by - ball courts, playground and a pavilion. Close to historic Chestertown and just 45 minutes to Middletown and tax-free shopping!

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,846
Status:
Active
MLS#:
MDQA2008320
Type:
Single Family, Single Family-Detached
Subdivision:
The Grove
Lot size:
1.23 Acres
Year built:
1996
Courtesy: Cross Street Realtors LLC, 4434803453
View additional info

Don't miss your chance to own this charming rancher located in the sought-after community of The Grove. With over 2000 sq. ft., three bedrooms, two bathrooms, and an open floor plan that bathes the space in natural light, it's a perfect blend of comfort and privacy. Nestled in a sprawling 1.23-acre yard, partially fenced for added privacy, this residence is a haven in a quiet cul-de-sac within the renowned Queen Anne's County school district. The well-designed layout ensures privacy with the primary suite and en-suite cleverly separated. The primary suite, featuring an en-suite bathroom and walk-in closet, provides a tranquil retreat. The modern kitchen sets the stage for culinary delights and lively gatherings and is perfect for culinary adventures. The attached 428ft garage, equipped with a generator, has been converted to add additional living space perfect for an entertainment, theatre, or game room. What sets this home apart? A detached garage/versatile pole barn adds both functionality and charm, perfect for any enthusiastic hobbyist! Restaurants, beaches, and marinas are all within 2 miles, offering plenty of sunshine fun! Perfectly positioned just a few short miles from Centreville or Downtown Chestertown showcasing festivals, farmer markets, restaurants, walking trails, parks, and artisan stores galore! Minutes to 301 for easy commuting to Annapolis, Baltimore, DC or Delaware.

Beds:
2
Baths:
2 Full
Sq.Ft.:
1,150
Status:
Active
MLS#:
MDKE2003374
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester Estates
Lot size:
0.46 Acres
Year built:
1949
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Price improvement! Two perfectly adorable cottages in Tolchester. Both were completely remodeled. The cottages sit on 3 lots totaling about .46 acres. Each has one bedroom, a full bath, kitchen and living areas. The front cottage also has an additional "sleeping loft". Tolchester Beach is located on the Chesapeake Bay and has a beautiful beach and boat ramp. Walking distance to The Shanty Beach Bar and the Tolchester Marina. A great place to enjoy live music, great food and drinks. Each unit has new mini-split systems for heating and cooling. These would be a perfect vacation home or you could live in one and rent out the other. These would also make good airbnb or vrbo properties. The front cottage is approximately 400 sq ft. The back cottage is approximately 750 sq ft. Come check them out!

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,454
Status:
Active
MLS#:
MDKE2003384
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Heights-Rt 213 N
Lot size:
0.21 Acres
Year built:
1956
Courtesy: Cross Street Realtors LLC, 4434803453
View additional info

Prime Location Alert! Nestled along one of Chestertown's bustling thoroughfares, this delightful 3-bedroom, 1-bathroom bungalow exudes charm and possibility. Boasting a coveted Intense Village zoning, this property opens doors to a myriad of opportunities, whether for residential bliss or a variety of commercial endeavors. Step inside to find a generous family room seamlessly connected to the galley kitchen, offering a cozy yet functional layout. Relax and unwind in the screened-in porch or take advantage of the detached 2-car garage, complete with abundant off-street parking. Recent upgrades add to the allure, including a new heat pump with central air in 2021, a fresh roof installment 2022, and plush new carpetingâeach enhancing both comfort and aesthetics. Location-wise, convenience reigns supreme, with proximity to Chestertown's treasures such as Washington College, the hospital, local boutiques, the newest marina, eclectic dining options, and much moreâall just a stone's throw away, promising a lifestyle of ease and accessibility. Overflowing with potential, this property beckons for visionaries and dreamers alike. Please take note, there's an existing lease in place, expiring on December 31, 2024. Don't miss out on this golden opportunity!

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
2,866
Status:
Active
MLS#:
MDKE2003356
Type:
Single Family, Single Family-Detached
Subdivision:
Downtown Chestertown
Lot size:
0.14 Acres
Year built:
1900
Courtesy: Cross Street Realtors LLC, 4434803453
View additional info

This former horse barn was converted in 1990 into a well-crafted personal residence. In early 2018, the current stewards retained acclaimed contractors Taylor Loughry to apply their craftsmanship to a large portion of the house. The most delightfully unique characteristic of this 4-5 bedroom, 3 and 1/2 bath home with attached two car garage is its' private, landscaped lot accessed by a gravel driveway on North Water Street. A pair of new wood gates define the entry to the oasis. The redesigned flow of the first floor provides well for the intended purpose of both entertaining and home comfort. A den, powder room, and elevator adjoin the two-story, sun-filled foyer. A large living room with gas fireplace and separate dining room (with doors to the rear brick patio and raised beds) provide the pathway to a beautifully designed large island kitchen with breakfast area with bay window. Mudroom with sink, full sized washer and dryer and storage is adjacent to a side entry and double garage with EV charging station. Floor two comprises mostly a primary suite that includes bath, large office and exercise space with access to a very large, insulated and conditioned storage space (easily repurposed to a games room or home theatre), a guest bedroom and hall bath. The third-floor features two additional bedrooms and bath with large amounts of closet space. Recently installed solar panels, discreetly positioned, have resulted in nearly net zero energy expense.

Beds:
2
Baths:
1 Full
Sq.Ft.:
826
Status:
Active
MLS#:
MDQA2007694
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
0.81 Acres
Year built:
1961
Courtesy: Benson & Mangold, LLC, (410) 822-6665
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BRING ALL OFFERS! Welcome to this newly renovated home with stunning upgrades throughout! This charming, easy-living home, in Chestertown, MD has all new LVP flooring, paint and drywall, a brand-new kitchen featuring sleek grey cabinets, stainless steel appliances, a deep sink, backsplash, and quarts countertops. The bathroom boasts a beautifully tiled shower. New washer and dryer on the main floor, and beautiful windows to let in an abundance of natural light. Enjoy almost an acre of land with plenty of room to enjoy the quiet outdoors. This home is located in Queen Anneâs County, close to rt 301, making for a short commute 25 minutes to Middletown, DE, 35 minutes to the Chesapeake Bay Bridge, and lots of local amenities near by.

Beds:
4
Baths:
4 Full/1 Half
Sq.Ft.:
5,195
Status:
Active
MLS#:
MDKE2002790
Type:
Single Family, Single Family-Detached
Subdivision:
Historic Chestertown
Lot size:
0.39 Acres
Year built:
1760
Courtesy: Maryland Heritage Properties, (443) 480-7342
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SMITH-RINGGOLD HOUSE. ca. 1750 This exceptional property is a rare find: an authentic waterfront 18th century home with 21st century comfort in heart of Historic Districtnof Chestertown on Maryland's Eastern Shore. Originally a merchantâs home , the Smith-Ringgold house has been tastefully modified representing four defined periods and enlarged over the course of its 250-year history. William Ringgold added rooms toward the River in about 1759 that doubled the space. (Often, one would find 18th c. additions such as this creating a telescope style design. ) The present owner took two-years to restore the home from foundation to attic. A river-side sun-porch/breakfact room was added. ,The cedar shingle roof, , plumbing, wiring, heat and A/C systems were added or replaced. Wood floors throughout the house have been beautifully restored. Modern storm windows are energy efficient and all but eliminate street sounds. Aside from your own personal touches, this house awaits our arrival anf iss prepared for the next century. The ground floor has a large double parlor, serene sitting room, formal dining room, breakfast room, and a stunning Chefâs kitchen. An important feature is the hand painted dining room mural by noted artist Jack Schroeder. The front hall, redesigned in about 1860, replaced a steep stairway with a grand and gracefully curving staircase. The second floor contains three large en-suite bedrooms and a laundry room that is also accessible from the kitchen via a âsecretâ staff stairway. The third floor has a large sitting room, bathroom, and fourth bedroom. A setion of the homeâs original c. 1750 roof has been restored forming a unique design element. The backyard was extensively terraced, probably in the late 1700s, in descending levels down to the Chester River eliminating the fear of flooding. The free-standing brick garage dates from the early 20th century, when car garages replaced horse barns. This structure could easily be repurposed as an artistâs studio or home workshop. A wide driveway area provides additional off-street parking. Truly an inviting residence for intimate family evenings or grand parties. Perfect setting for one's collection of antiques or for the simplicity of contemporary furniture which emphasizes the wonderful architecture. CHESTERTOWN IN THE COUNTY OF KENT Chestertown was founded in 1706 on the broad Chester River and served as an important shipping hub for trade with England and between the colonies. As the U.S. population center moved westward, Kent County settled into two hundred years of quiet agricultural and commercial fishing activities. Chestertown is home to a surprisingly large number of elegant, historical Georgian homes as well as Victorian âpainted ladies.â With a population of 5,600, Chestertown is only an hour from Annapolis or Wilmington, about two hours from Baltimore, Philadelphia or Washington, and under four hours from New York City. Chestertown in the County of Kent is "a place where one would rather be". Centrally located Washington College (founded in 1782 with the personal support of George Washington) provides Chestertown a mix of athletic competitions, music and drama, adult education, and visiting speakers. The town boasts a weekly Farmers Market, excellent coffee bars, restaurants, and art galleriesâbut no big box stores. The Chester River Yacht & Country Club offers an 18-hole golf course as well as a sailing program. The whole community supports major events like the annual Tea Party, commemorating a Revolutionary War protest; a Dickens Christmas Street Fair; and Down-rigging Weekend, when tall ships offer tours and sails on the Chester River. Today, Chestertown, is a vibrant mix of old families, newcomers, college students, full time residents with children, and involved weekenders.

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