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Chestertown MD Real Estate & Homes for Sale

63 Properties Found

The median home value in Chestertown, MD is $344,700. 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 $344,700. 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:
2.00
Sq.Ft.:
1,904
Status:
NEW LISTING
MLS#:
MDKE2006950
Type:
Single Family
Subdivision:
HEATHER HEIGHTS
Lot size:
0.8 Acres
Year built:
1978
Courtesy: Doug Ashley Realtors, LLC
View additional info

Welcome home to 7982 Radcliffe Road! This charming corner-lot offers a perfect blend of character and modern comfort. Built in 1978- this well maintained 2 bedroom, 2 bathroom home feels more of a newer era. Inside you'll find a spacious living room with plenty of room to relax by the fireplace or entertain! The oversized garage offers amazing storage and features an office space that is closed off. Outside, you can enjoy the nice-sized yard with the views of a crop field and beautiful sunsets. Located right outside of Chestertown, the home puts shops, restaurants, and the local farmers market close by and is also walking distance to a view of the Chester River! An amazing opportunity to enjoy small-town living convenience, space & character!

Beds:
5
Baths:
3.00
Sq.Ft.:
1,936
Status:
NEW LISTING
MLS#:
MDKE2006914
Type:
Single Family
Subdivision:
TOLCHESTER ESTATES
Lot size:
0.38 Acres
Year built:
2006
Courtesy: Save 6, Incorporated
View additional info

Located in a beautiful waterfront community, this refreshed 5-bedroom, 2.5-bath home offers approximately 1,936 square feet of comfortable living space on approximately 0.38 acres. The property combines updated interiors, flexible living spaces, and the relaxed lifestyle of Maryland's Eastern Shore. The home offers five generously sized bedrooms, providing comfortable space for family, guests, or work-from-home needs. The versatile fifth bedroom can function as a home office, guest room, flex space, or secondary suite, depending on your needs. The upgraded kitchen features bright white cabinetry, updated countertops and backsplash, stainless-steel Whirlpool appliances, and a KitchenAid dishwasher. The French-door refrigeratorincludes a front water and ice dispenser for added convenience. Attractive ceiling fans throughout the home add both comfort and style. The main living area is anchored by a stylish electric fireplace with custom floating shelving, creating a warm focal point for the home. With five bedrooms, the layout offers excellent flexibility, and the fifth bedroom can also serve as a home office, guest room, or additional flex space. The partially finished one-car garage offers added versatility beyond traditional vehicle parking and storage. It can also serve as a game room, entertainment area, recreation space, hobby room, home gym, or additional flex space, giving buyers even more options for how they use the home. Step outside to an expanded rear deck, hot tub, and fire-pit/seating area, ideal for relaxing or entertaining. Boating enthusiasts will appreciate the nearby seasonal marina with restaurants and a dive bar 3 blocks away and a public boat ramp approximately one mile away, providing convenient access to the area's waterways. Additional updates include an approximately two-year-old water heater and a private well with an upgraded water-treatment/softening system, professionally serviced in 2025 with a new Clack neutralizer head installed. Whether used as a primary residence, vacation home, weekend retreat, or a home designed for entertaining, 8630 Elm Road offers space, versatility, thoughtful updates, and the Eastern Shore lifestyle in one inviting package.

Beds:
3
Baths:
3.00
Sq.Ft.:
3,344
Status:
NEW LISTING
MLS#:
MDKE2006878
Type:
Single Family
Subdivision:
COVENTRY FARMS
Lot size:
0.25 Acres
Year built:
2008
Courtesy: Elevated Real Estate Solutions
View additional info

PICTURES COMING SOON Welcome home to this beautiful 3-bedroom, 2.5-bath residence in the charming town of Chestertown, MD. Designed for both comfortable living and effortless entertaining, this home offers spacious interiors filled with abundant natural light. The main level features a bright kitchen with Breakfast Bar that flows seamlessly into a sunny Florida room, creating the perfect space to enjoy your morning coffee or unwind while overlooking the backyard. You'll also find a formal dining room for hosting special occasions, a welcoming living room, and a cozy family room that provides plenty of space for everyday living. Downstairs, the finished basement offers versatile additional living space ideal for a recreation room, home theater, fitness area, playroom, or home office. There is enough space to do all of it. The unfinished area has full laundry and ample storage. Upstairs, the expansive owner's suite serves as a private retreat, complete with a generous walk-in closet and an ensuite bathroom featuring a soaking tub. Two additional bedrooms each offer large closets and ample space for family, guests, or a home office. A full bathroom conveniently located off the second-floor sitting area completes the upper level. Step outside to your own private backyard oasis. The landscaped yard features a refreshing in-ground swimming pool with a new tile finish and a new filtration system, making it ready for years of enjoyment. A new deck with a privacy wall extends from the home, providing the perfect setting for outdoor dining, entertaining, or relaxing poolside. Additional highlights include a large storage shed and a newly installed rock bed surrounding the pool deck that enhances both beauty and low-maintenance landscaping. For added peace of mind, the home also features a roof that is only two years old. Combining spacious living areas, thoughtful updates, exceptional outdoor amenities, and a desirable location in historic Chestertown, this home truly has something for everyone. Don't miss the opportunity to make this exceptional property your next home!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,404
Status:
Active
MLS#:
MDKE2006880
Type:
Manufactured Home
Subdivision:
CHESAPEAKE LANDING
Lot size:
0.34 Acres
Year built:
2001
Courtesy: Doug Ashley Realtors, LLC
View additional info

Welcome to Chesapeake Landing! Come see this amazing home offering vaulted ceilings, huge master bath, open concept, plenty of closet space, laminate flooring, and a private secluded fenced lot. Located in a water oriented neighborhood with community boat ramp and pier and nearby restaurants and marina. Move here and enjoy all the Eastern Shore has to offer!

Beds:
4
Baths:
2.00
Sq.Ft.:
1,476
Status:
Active
MLS#:
MDKE2006874
Type:
Single Family
Subdivision:
CRESTVIEW
Lot size:
0.74 Acres
Year built:
2018
Courtesy: Kevin Dey Realty
View additional info

Adorable 4 bedroom 2 bathroom Cape Cod in the quiet Crestview neighborhood in Chestertown close to Restaurants, Shopping, the brand new YMCA and the Historic Downtown. Eat in kitchen with back deck overlooking a beautiful yard that backs up to farm land that is preserved forever. Freshly painted with new carpet! Washer & dryer in unit. Extra storage in knee walls upstairs. In Chestertown but outside the town limits so no town tax or water/sewer bill! Come make this home yours today, immediate occupancy.

Beds:
5
Baths:
4.00
Sq.Ft.:
4,353
Status:
Active
MLS#:
MDKE2006786
Type:
Single Family
Subdivision:
ORCHARD HILL
Lot size:
2.23 Acres
Year built:
2006
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Welcome to a breathtaking country estate where modern elegance, architectural grandeur, and total sanctuary converge across 2.23 serene acres. Spanning over 4,000 square feet of meticulously refined living space, this extraordinary five-bedroom residence has been thoughtfully crafted to offer both lavish entertaining possibilities and effortless multi-generational comfort. Upon arrival, the welcoming foyer makes a memorable first impression, framed by detailed custom millwork and flanked by a private executive office and a sophisticated study or formal dining space. Moving inward, the magnificent two-story great room commands attention with its soaring ceilings and a cozy gas fireplace crowned by a classic raised brick hearth. At the heart of the main level lies a gourmet kitchen designed for grand gatherings, showcasing fresh luxury vinyl flooring, select new appliances, and a stunning quartz-topped center island with a prep sink that easily reconfigures for multi-purpose hosting. Sunbeams flood the adjoining sunroom, creating a seamless transition to the outdoors while mirroring the warmth of the home's main-floor primary suite. This private retreat features a spacious walk-in closet and a newly remodeled, spa-inspired bath complete with new quartz double vanities, sleek updated fixtures, a large walk-in shower, and an exquisite standalone soaking tub. Offering unmatched independence and comfort, a fully self-contained ground-level suite on the lowest level serves as the ultimate in-law or guest quarters. Complete with its own private ground-level entrance, open-concept kitchen and living area, dedicated laundry, and an accessible bath with a walk-in shower, this wing ensures total convenience without sacrificing style. A new addition to the lower level unlocks movie-theater magic with a fully furnished screening room ready for immediate enjoyment. Upstairs, four generously proportioned bedrooms accompany a beautifully refreshed hall bath. The exterior grounds are nothing short of a resort-style paradise. Step out onto the back porch to take in sweeping views of the lush landscape and expansive partially fenced yard. The sparkling inground pool serves as the crown jewel of the outdoor space, newly upgraded with all-new mechanicals including a dedicated heater. Surrounding the water, extensive custom hardscaping leads to a fireside gathering area, while an oversized gazebo with an outdoor fan offers a shady retreat on warm afternoons. With a brand-new roof installed in 2026, a newly resurfaced driveway, and space remaining for future additions, this estate represents a rare opportunity to experience sophisticated countryside living at its finest and, less than 5 minutes from Chestertown's restaurants, shopping, and Farmer's Market. Updates to the home are available in Documents

Open House:

Tuesday, 8/18 5:00-7:00PM

Beds:
3
Baths:
2.00
Sq.Ft.:
1,280
Status:
Active
MLS#:
MDKE2006826
Type:
Townhouse
Subdivision:
CHESTER ARMS
Lot size:
0.05 Acres
Year built:
2025
A broker reciprocity listing Courtesy: Real Broker, LLC
View additional info

Brand new home in Historic Chestertown available for move-in now. This interior unit features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Priced at $259,900, this home also comes with a $5,000 builder incentive plus % ($1,299) through our lender partnership - making it possible to own for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown's most historic locations.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,857
Status:
Active
MLS#:
MDKE2006736
Type:
Single Family
Subdivision:
COUNTRY CLUB ESTATES
Lot size:
0.72 Acres
Year built:
1990
Courtesy: Cross Street Realtors LLC
View additional info

Welcome to this spacious brick rancher located in the desirable Country Club Estates neighborhood, offering over 2,800 square feet of beautifully updated living space in a peaceful, park-like setting. Designed for both comfort and elegance, this home features expansive, light-filled interiors and timeless architectural details throughout. The heart of the home is a large, luxurious living room showcasing vaulted, beamed ceilings, a fireplace, and sweeping views of the expansive rear yard. Rich hickory hardwood flooring runs throughout the kitchen, breakfast area, living room, office, and formal dining room, creating a warm and cohesive flow across the main living spaces. The formal dining room is enhanced with elegant crown molding, offering a refined setting ideal for both everyday living and entertaining. The updated gourmet kitchen features granite countertops, abundant cabinetry, and a seamless connection to the breakfast area and main living spaces, making it both functional and inviting. The private primary suite is generously sized and offers two walk-in closets along with a beautifully appointed en-suite bath featuring a luxury soaking tub, double vanity, travertine tile flooring, and a tiled walk-in shower. Two additional bedrooms provide ample closet space and share a well-appointed full bath, also finished with travertine tile flooring and a tiled shower. Outdoor living is equally impressive with extensive mature landscaping that enhances privacy and natural beauty. A stone patio and a combination of brick and Trex decks provide multiple spaces for relaxing or entertaining while enjoying the serene surroundings. Additional features include an attached two-car garage as well as a detached one-car garage, offering exceptional storage and flexibility. Ideally located just minutes from historic Chestertown and only a golf cart ride to the Chester River Yacht and Country Club and the Chester River, this exceptional home blends privacy, convenience, and luxury Eastern Shore living at its finest.

Beds:
4
Baths:
2.00
Sq.Ft.:
2,198
Status:
Active
MLS#:
MDKE2006808
Type:
Single Family
Subdivision:
FOXLEY MANOR
Lot size:
0.47 Acres
Year built:
1987
Courtesy: TTR Sotheby's International Realty
View additional info

A rare opportunity to own a classic two-story split-level home in Chestertown - set on a large, shaded corner lot just a few miles to Downtown Chestertown, Washington College, the weekly farmers market, the town's annual festivals, and only steps to locally loved restaurants and everyday conveniences. This is the kind of home that simply isn't built anymore: classic lines, original details, and the quiet character that comes from decades of careful ownership. Step inside and the home tells its story with original trim, classic proportions and timeless architectural touches. The two-story split-level floor plan offers a thoughtful separation of living and sleeping spaces, with a sun-filled sunroom that works beautifully as a screened porch when the doors are all open or as extra living space during the shoulder seasons. Two of the bedrooms sit on the upper level, while two large bedrooms flow comfortably below. Out back, the large, gently sloped corner lot offers privacy, mature trees, and room to garden, entertain, or simply enjoy a quiet afternoon. The setting feels tucked away, while the rest of Chestertown is just a short jaunt from the front door. The two-bay carport keeps your vehicles safe from the elements in the wide stone driveway. What truly sets this home apart is its condition. It has been maintained impeccably - spotlessly clean, carefully tended, and gently lived in. The HVAC system is new, and the kitchen and laundry appliances are all young as well, giving the next owner the best of both worlds: classic character on the outside, modern mechanicals where it counts. The remaining finishes offer a thoughtful canvas for the next owner to put their own stamp on it, with the confidence that the bones and the care have already been handled. Classic character, pristine condition, and convenience to it all.

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDKE2006678
Type:
Townhouse
Subdivision:
CHESTER ARMS
Lot size:
0.09 Acres
Year built:
2025
A broker reciprocity listing Courtesy: Real Broker, LLC
View additional info

Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown's most historic locations.

Beds:
2
Baths:
1.00
Sq.Ft.:
1,232
Status:
Active
MLS#:
MDKE2006816
Type:
Townhouse
Subdivision:
TOLCHESTER
Lot size:
0.05 Acres
Year built:
1955
Courtesy: Benson & Mangold, LLC
View additional info

Welcome to this beautifully renovated 2-bedroom, 1-bath townhome offering the perfect blend of comfort, style, and convenience. Completely updated from top to bottom, this move-in-ready home features brand-new luxury vinyl plank flooring, fresh paint throughout, quartz countertops, an updated bathroom, and several new appliances. The fully equipped kitchen opens to a comfortable living and dining area, where a sliding glass door leads to your own private concrete patio; perfect for enjoying your morning coffee or relaxing outdoors. Upstairs, you'll find two generously sized bedrooms, a full bathroom, and additional storage space. All appliances convey, making this home truly turnkey. Nestled in a peaceful, wooded setting between Rock Hall and Chestertown, you'll enjoy a serene atmosphere while being just minutes from schools, shopping, beaches, marinas, and local dining. Whether you're a first-time homebuyer, looking to downsize, or searching for your next investment property, this beautifully updated townhome checks all the boxes. Don't miss your opportunity to own this hidden gem! **Sellers willing to help with buyer closing costs**

Beds:
3
Baths:
2.00
Sq.Ft.:
1,192
Status:
Active
MLS#:
MDKE2006794
Type:
Townhouse
Subdivision:
CALVERT HOMES
Lot size:
0.05 Acres
Year built:
1992
Courtesy: Chesapeake Real Estate Associates, LLC
View additional info

Affordable opportunity in the heart of downtown Chestertown! This 3-bedroom, 1.5-bath townhome is ideally located just minutes from Washington College, shops, restaurants, parks, and the waterfront. Offering a functional floor plan with spacious living areas, generously sized bedrooms, and a back yard with additional rear parking, this home is ready for its next owner to make it their own. This property presents an excellent opportunity for first-time homebuyers looking to build equity or investors seeking their next investment property! Opportunities at this price point in Chestertown don't come along often! Schedule your showing today and discover the potential this home has to offer! Property is being sold AS-IS.

Beds:
5
Baths:
4.00
Sq.Ft.:
3,960
Status:
Active
MLS#:
MDKE2006758
Type:
Single Family
Subdivision:
COUNTRY CLUB ESTATES
Lot size:
0.81 Acres
Year built:
2001
Courtesy: Gunther-McClary Real Estate
View additional info

Custom-built home in Country Club Estates with beautiful architectural details. Spacious open living space with hardwood floors and wooden beams, glowing with ample natural light! Enjoy time on the large screened porch, finished with Ipe hardwood, overlooking the peaceful creek, woods and park like setting. Five bedrooms and 4 full bathrooms, nicely designed with privacy in mind. There's an entry-level bedroom and full bathroom. The partially finished basement offers a large bedroom or bonus room, a full bathroom, and an oversized workshop space. Upstairs you'll find two bedrooms that share a full bathroom, as well as the primary bedroom, which is nicely situated with a view of the creek/pond. Enjoy peaceful views of the creek from the slate patio, and launch a kayak to explore the water from your backyard. This property leaves little to be desired! Two-car garage, peaceful water view, cozy fireplace, large living space, nicely landscaped, and a hot tub! Under 2 miles from downtown Chestertown and a short stroll to the Chester River Yacht & Country Club.

Beds:
3
Baths:
1.00
Sq.Ft.:
2,000
Status:
Active
MLS#:
MDKE2006750
Type:
Single Family
Subdivision:
NONE AVAILABLE
Lot size:
0.34 Acres
Year built:
1965
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial. Full finished basement. More details and pictures coming soon!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,280
Status:
Active
MLS#:
MDKE2006686
Type:
Townhouse
Subdivision:
CHESTER ARMS
Lot size:
0.07 Acres
Year built:
1979
Courtesy: Cummings & Co. Realtors
View additional info

Price Improvement! Now offered at $239,900 Welcome to 104 Conley Drive in the heart of Chestertown! This move-in ready 3-bedroom, 1.5-bath townhome offers comfortable, low-maintenance living with a spacious layout and fenced rear yard. The main level features a bright living room, an eat-in kitchen with ample dining space, and a convenient half bath. Upstairs, you'll find three bedrooms and a full bath. Notable updates include a new HVAC system installed in 2020 and a sewer line replacement completed approximately four years ago, providing added peace of mind for the next owner. Enjoy outdoor entertaining, gardening, or relaxing in the private fenced backyard. Conveniently located near shopping, dining, schools, parks, the YMCA, and historic downtown Chestertown, this home is an excellent opportunity for first-time buyers, downsizers, or investors alike. Schedule your showing today!

Beds:
2
Baths:
1.00
Sq.Ft.:
1,296
Status:
Active
MLS#:
MDKE2006670
Type:
Single Family
Subdivision:
NONE AVAILABLE
Lot size:
0.09 Acres
Year built:
1900
Courtesy: Cummings & Co. Realtors
View additional info

Investor Special - Charming Colonial in Prime Chestertown Location! Welcome to 234 N College Ave, an adorable colonial full of character and potential, nestled in the heart of historic Chestertown. This short sale opportunity is a rare find for savvy investors or buyers ready to bring their vision to life. With classic colonial charm, this property offers the perfect canvas for renovation or restoration. Located near downtown Chestertown's shops, restaurants, and waterfront, the location can't be beat. Original architectural details, a cozy layout, and timeless curb appeal make this home a standout gem waiting to be polished. Don't miss your chance to invest in one of Maryland's most beloved small towns. Sold as-is. Cash or renovation loans preferred.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,900
Status:
Active
MLS#:
MDKE2006668
Type:
Townhouse
Subdivision:
OAK HOLLOW
Lot size:
0.05 Acres
Year built:
2004
Courtesy: Cross Street Realtors LLC
View additional info

Embrace Eastern Shore living in this beautifully designed Oak Hollow townhome. Offering 1,900 square feet of spacious, three-level living, this property is perfectly positioned just minutes from historic downtown Chestertown, local schools, and the YMCA - blending everyday convenience with a welcoming community atmosphere. Enter through the ground floor, where a flexible bonus room and one-car garage offer endless possibilities for a home office, gym, or recreation space. The heart of the home sits on the main level, featuring a generous living room and an eat-in kitchen that opens to a private rear deck - the perfect spot to unwind and look out at the wooded backdrop. Upstairs, you will find three comfortable bedrooms, including a primary suite with a private bath, alongside a dedicated laundry area. Turn-key and low-maintenance, this property is a fantastic opportunity for first-time buyers, downsizers, and investors alike.

Beds:
3
Baths:
2.00
Sq.Ft.:
3,262
Status:
Active
MLS#:
MDKE2006546
Type:
Single Family
Subdivision:
COUNTRY CLUB ESTATES
Lot size:
0.76 Acres
Year built:
1954
Courtesy: Doug Ashley Realtors, LLC
View additional info

Rambling rancher on an established 3/4 acre garden in Country Club Estates with No HOA fees has extensive recent renovations: New architectural shingle Roof, New Heat pump, Stainless Kitchen appliances, New Bathroom fixtures, New Porch screening, New doors, New Ring video doorbell, ceiling lights and switches, Fresh paint and 6 New windows brighten a Basement Family room with 18 porcelain tile. A 40' x 26' block 2-car Garage with New insulated doors & openers, built-in shelving, jalousie windows, storage loft and 50% garage extension for Workshop as potential hobby space, home-based business or sporting gear cave. The Garage faces a private parking pad behind the home and a U-shaped driveway to a drive-through carport has the rear door entering a large Foyer convenient for bring in the groceries to the custom built Kitchen with a work-triangle layout. Finishing touches to the renovations are nearly complete, just choose the bedroom Carpeting and move into your New Home! Living Room: Walk along the slate flagstone path and pass through the New, classic Front Door into a spacious Living room featuring an elegant Fireplace and Hardwood floors that extend through a wide open Archway into the Dining room which opens to a comfortable screened Porch - the perfect spot to relax and enjoy the Garden view in this Prestigious neighborhood. Bedrooms: The main floor has a secluded Bedroom Wing with Hardwood floors and full Bathroom with 2 linen closets. A second Bathroom is conveniently close to Foyer and stairwell to Basement: The full Basement features an open Family room with brand-new windows that allow plenty of natural light inside. A side room equipped with a new sump pump well is a perfect blank canvas offering for an Office, Storage or a Rec room. Mechanical & Utillity Room: Separate Electric water heater from Oil boiler to provide comfortable hot water baseboard heat which is supplemented by a new HVAC system for Efficient heating and cooling. Enjoy Resort-like living in this Brick Ranch house only a chip shot away from the Chester River Yacht and Country Club with scenic river views while taking your neighborhood walks, And 5 minute drives along the Chester River, coming and going from your New Home to Historic Chestertown shopping and dining district, also well known for Live Arts, Festivals and home to Washington College.

Beds:
4
Baths:
1.00
Sq.Ft.:
2,920
Status:
Active
MLS#:
MDKE2006642
Type:
Single Family
Subdivision:
CHESTERTOWN
Lot size:
0.28 Acres
Year built:
1972
Courtesy: Blue Star Real Estate, LLC
View additional info

Great area and lot walking distance to the Chesapeake bay and Tolchester Marina. House is in need of rehab but offers quite a bit of upside in the lot and location. Buyer to verify all info

Beds:
4
Baths:
3.00
Sq.Ft.:
2,160
Status:
Active
MLS#:
MDKE2006640
Type:
Single Family
Subdivision:
CHESAPEAKE LANDING
Lot size:
0.39 Acres
Year built:
2001
A broker reciprocity listing Courtesy: Real Broker, LLC
View additional info

Welcome home to relaxed Eastern Shore living in the waterfront community of Chesapeake Landing. This beautifully updated 2,140 sq ft Cape Cod offers the perfect blend of charm and modern comfort with 3 bedrooms, 2.5 baths, and a welcoming floor plan designed for everyday life. The main level features new flooring throughout, a spacious living area, formal dining room, and a renovated country kitchen with new appliances, new counters, and plenty of space for gathering. A main-level bedroom adds flexibility for guests or one-level living. Enjoy morning coffee or evening sunsets on the back deck overlooking the open, cleared 0.39-acre lot - perfect for gardening or outdoor fun. Additional highlights include a 2-car garage and access to community amenities with a beach, fishing pier, and pavilion. Just minutes from historic downtown Chestertown, you'll love being close to local shops, dining, marinas, and all the charm of Eastern Shore living.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,277
Status:
Active
MLS#:
MDKE2006026
Type:
Single Family
Subdivision:
BYFORD DEVELOPMENT
Lot size:
0.34 Acres
Year built:
1965
Courtesy: Doug Ashley Realtors, LLC
View additional info

Desirable in-town living in a peaceful neighborhood. This solid brick front rancher was totally renovated in 2022 and is still like New. The pictures tell the story. Easy one-level living with an open concept for the Living Room, Dining, and Kitchen. A really open feel. This home offers 4 bedrooms and 2 full bathrooms. If this many bedrooms are not needed, the fourth bedroom could have many other potential uses, with it being right off the kitchen and living room. Out front, you have a cozy front porch, and out from the sliding glass door it opens up to a deck and a good-size backyard. Just pick where you would like to sit for a few and relax. In the back of the yard, you have a new storage shed that is always a plus. Bring your bikes; you will have the perfect streets in this neighborhood to ride and use as you head to the Local Farmers Market. The pictures show this house perfectly. It is in such good condition and has been well cared for and maintained. All ready to move into. It won't disappoint.

Beds:
9
Baths:
7.00
Sq.Ft.:
6,000
Status:
Active
MLS#:
MDKE2006596
Type:
Single Family
Subdivision:
TOLCHESTER
Lot size:
9.2 Acres
Year built:
1743
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Circa 1743 with a stately 1825 addition, The Inn at Mitchell House is a rare pre-Revolutionary manor home on 9+ manicured acres on Maryland's Eastern Shore. Listed on the National Star-Spangled Banner Trail and just a mile from the Chesapeake Bay, this storied property offers a once-in-a-generation chance to own one of the region's most beloved historic estates. The grounds unfold past champion and organic fruit trees, a generous herb garden, an original 18th-century smoke house, two private bridges over Stoneybrook Pond which are all framed by woods and rolling farm fields. Inside, nine bedrooms and six-and-a-half bathrooms reveal nearly two and a half centuries of craftsmanship: original wood floors, brick floors in the dining room and kitchen, signature Bulls Eye moldings, exposed hand hewn beams, eight fireplaces and soaring 11-foot ceilings. For more than 40 years the property has operated as a successful Bed & Breakfast. An optional furniture package is available for a seamless turnkey transition. Its origins as a single-family residence also make it an extraordinary private estate, full-time home or weekend retreat. A coveted sewer allotment is included with the sale which opens the door for a future carriage house, barn, additional dwelling, stable, studio or expanded hospitality use. A new roof, a complete exterior paint job, new hot water heater, new well pump and updated electrical service were completed in 2025-2026. This delivers the rare combination of historic character and modern peace of mind. Tolchester Marina and the Shanty Beach Bar are a mile away. Rock Hall is six miles down the road and the charming historic district of Chestertown is just ten miles away. After nearly four decades of careful stewardship, the current owners are ready to pass on the privilege and the story of The Mitchell House.

Beds:
3
Baths:
1.00
Sq.Ft.:
1,248
Status:
Active
MLS#:
MDKE2006394
Type:
Manufactured Home
Subdivision:
CHESTER HEIGHTS
Lot size:
0.69 Acres
Year built:
1975
Courtesy: Doug Ashley Realtors, LLC
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Nice basic rancher offering 3 bedrooms and a full bath, generous sized living room with a large window allowing plenty of light in. The kitchen has an eat-in counter space that opens into the dining area. This space is nice and open, as you can easily see into the living room. Still plenty of space for a table. The washer and dryer are located in the oversized storage closet with bi-fold doors in the kitchen. Has an additional coat closet as you come in the side door and a separate pantry. Nice open back yard. A solid house in proximity to town. Good place to make your own and call home, or an investment.

Beds:
4
Baths:
5.00
Sq.Ft.:
5,265
Status:
Active
MLS#:
MDKE2006502
Type:
Single Family
Subdivision:
FAIRGALE PROPERTIES
Lot size:
3.55 Acres
Year built:
2002
Courtesy: Gunther-McClary Real Estate
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Welcome to 22470 Fairgale Farm Ln, a spacious home and property perched over Fairlee Creek, with an assigned boat slip. 3.55 acres, partly wooded, exceptionally landscaped, and perfectly framed water views. Walk down to the water to enjoy the views or launch a kayak. The deep-water boat slip, outfitted with a boat lift, is just a short distance away. The home features 4 bedrooms and 5 full bathrooms, plus a large loft that could be used as an additional bedroom. The large eat-in kitchen has expansive windows that perfectly frame the water view. A great spot for entertaining! Doors in the kitchen lead to the waterfront deck, spanning the front of the home. A new roof was installed in June, 2026. In both sitting rooms, you'll find fireplaces that have been conveniently updated to propane. The first-floor primary bedroom opens up to the waterfront deck and offers a fantastic water view, as well as a large bathroom that was recently updated. Upstairs you'll find two waterfront bedrooms, one with an updated attached bath. There's a second full bathroom and ample closet space in the hallway. Downstairs, there are two additional full bathrooms and a large bedroom. Above the kitchen sits the light-filled loft, a great office, studio, or extra bedroom. The exterior has a generous front porch, outdoor shower, circular drive, 2-car garage, fenced dog run, and additional garage space connected to the basement. This light-filled waterfront property is located 15 minutes away from the waterfront community of Rock Hall and historic Chestertown.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,880
Status:
Active
MLS#:
MDKE2006416
Type:
Single Family
Subdivision:
COVENTRY FARMS
Lot size:
0.23 Acres
Year built:
2007
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

PRICE IMPROVEMENT: Priced below 2025 Appraisal!! Instant equity! NOTE: Zillow's property taxes are incorrect: correct annual property taxes are $4,338. Welcome to 103 Trafford Drive; an exceptionally maintained 3 bedroom home just minutes from downtown Chestertown. Nestled in family-friendly Coventry Farms Community, this Colonial-style residence has been recently updated in all the right places for modern convenience and classic charm. Brand new kitchen cabinets, countertops, and appliances, 5-inch oak hardwood floors, back patio, washer/dryer are just a few up the recent updates. Some of the timeless interior features include a wood burning fireplace, tray ceilings, baseboard and crown moldings, chair railings, . Inside you are greeted by a traditional layout with a formal dining room and formal living room or office space. The front of the home flows seamlessly to the back where the heart of the home is: the newly renovated kitchen and living room space punctuated with a wood-burning fireplace. Recent kitchen improvements include: custom maple wood cabinets, quartz countertops, Frigidaire and LG stainless steel appliances, and a reverse osmosis water treatment system. The spacious and private back yard has a thick tree line to the back and has been elevated by a new concrete patio and wood steps and newly planted pine trees for additional privacy. Going upstairs one will find brand new 5-inch red oak hardwood floor throughout: and no thresholds! The spacious primary bedroom features an ensuite bath with jetted soaking tub and an oversized walk-in closet. The full basement could easily be turned into a fourth bedroom with electric, lighting, ductwork, and roughed-in plumbing all ready to go. Oversized two-car garage offers additional storage or parking. Don't miss this opportunity. This stunning home has been meticulously maintained and upgraded in all the right spots; offering exceptional elegance and modern comfort. Founded in 1706, Chestertown sits on the banks of the Chester and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals and an award-winning weekly Farmer's Market. Less than 90 minutes to Philadelphia and Washington D.C. Come see what Chestertown life is all about. Some furnishings may convey.

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BRIGHT MLS - All information, regardless of source, should be verified by personal inspection by and/or with the appropriate professional(s). The information is not guaranteed. Measurements are solely for the purpose of marketing, may not be exact, and should not be relied upon for loan, valuation, or other purposes.

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