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Chestertown MD Real Estate & Homes for Sale

53 Properties Found

The median home value in Chestertown, MD is $396,500. 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 $396,500. 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:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,964
Status:
NEW LISTING
MLS#:
MDKE2005960
Type:
Condo, Single Family-Detached
Subdivision:
CHESTER RIVER LANDING
Courtesy: Gunther-McClary Real Estate
View additional info

**To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area-perfect for entertaining. Upstairs, the primary suite features a spa-like bath and large walk-in closet. There are two additional bedrooms that share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,964
Status:
NEW LISTING
MLS#:
MDKE2005958
Type:
Condo
Subdivision:
CHESTER RIVER LANDING
Courtesy: Gunther-McClary Real Estate
View additional info

**To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area-perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to a private second floor balcony. There are two additional bedrooms that share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,964
Status:
NEW LISTING
MLS#:
MDKE2005956
Type:
Condo
Subdivision:
CHESTER RIVER LANDING
Courtesy: Gunther-McClary Real Estate
View additional info

**To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area-perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to a private balcony. There are two additional bedrooms that share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

Beds:
3
Baths:
3 Full/1 Half
Sq.Ft.:
2,192
Status:
NEW LISTING
MLS#:
MDKE2005952
Type:
Condo
Subdivision:
CHESTER RIVER LANDING
Courtesy: Gunther-McClary Real Estate
View additional info

**To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area-perfect for entertaining. There's also a private study, which could be used as additional space for guests. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and sliding doors to the second floor balcony. There are two additional bedrooms, each with their own full bathroom. the upstairs is complemented by a convenient second-floor laundry. This home is designed with future needs in mind, offering the option of a residential elevator for effortless access to all levels. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,964
Status:
NEW LISTING
MLS#:
MDKE2005950
Type:
Condo
Subdivision:
CHESTER RIVER LANDING
Courtesy: Gunther-McClary Real Estate
View additional info

**To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area-perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to the private balcony. Two additional bedrooms share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. Catch a glimpse of the Chester River from the front porch or upper covered balcony, the perfect place to enjoy morning coffee or evening cocktails. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
2,784
Status:
NEW LISTING
MLS#:
MDKE2005954
Type:
Condo, Single Family-Detached
Subdivision:
CHESTER RIVER LANDING
Courtesy: Gunther-McClary Real Estate
View additional info

**To be built! Welcome to this beautifully designed 2,784 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 4 bedrooms and 3.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area-perfect for entertaining. There is a first floor primary bedroom for one-floor living options. Upstairs, the second primary suite features a spa-like bath, large walk-in closet, and access to the private balcony. Two additional bedrooms share a full bathroom. Catch a glimpse of the Chester River from the front porch or upper covered balcony, the perfect place to enjoy morning coffee or evening cocktails. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club. Listing Office

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,232
Status:
NEW LISTING
MLS#:
MDQA2015648
Type:
Single Family, Single Family-Detached
Subdivision:
CHESTER HARBOR
Lot size:
0.34 Acres
Year built:
1984
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Great rancher in Chester Harbor on the Queen Anne's County side of Chestertown. Fresh paint and carpet throughout. Both bathrooms are completely remodeled. The kitchen could use updating, but the space is great and the appliances are in excellent condition. Plenty of room to add a kitchen island and still have space for a table. Nice 2 car detached "pole barn" style garage. Fenced back yard. This property has a lot to offer!

Open House:

Saturday, 12/6 12:00-1:00PM

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,040
Status:
NEW LISTING
MLS#:
MDKE2005920
Type:
Single Family, Single Family-Detached
Subdivision:
QUAKER ESTATES
Lot size:
0.56 Acres
Year built:
1969
Courtesy: Chesapeake Real Estate Associates, LLC
View additional info

The one youve been waiting for! This 3-bedroom, 1-bath rancher in Quaker Estates offers convenient living just minutes from downtown Chestertown. Features include an oversized pole building with cement floors and electric, plus a long blacktop driveway for plenty of parking. This home is move-in ready, with room for a buyer to add their own personal touches. It has been lovingly maintained with a newer roof and central heat/air. Competitively priced and full of potential!

Open House:

Saturday, 12/13 11:00-1:00PM

Beds:
3
Baths:
2 Full
Sq.Ft.:
2,296
Status:
NEW LISTING
MLS#:
MDKE2005896
Type:
Single Family, Single Family-Detached
Subdivision:
COLLEGE HEIGHTS
Lot size:
0.34 Acres
Year built:
1975
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Live with ease in this beautifully updated and maintained one floor home in downtown Chestertown. The current owners put a large addition on the house that includes a family room with wood burning stove, sunroom, and primary suite with en suite bathroom and walk in closet. A large laundry room on the main floor and updated kitchen with tons of counter space were other valuable design updates. The basement provides ample partially finished storage space in a completely dry environment due to serious structural improvements, sump pump and french drain system. Bring your hobby down there or your trusty work bench. The roof, HVAC, and hot water heater are all less than 10 years old. The front yard provides a polished experience with tasteful landscaping. The rear yard is quite large for a house in town and includes a raised bed garden and tidy shed. Experience the relaxed lifestyle of Chestertown with the Historic District's shops, Washington College, and the Margo Bailey park just a short walk away.

Beds:
5
Baths:
3 Full/1 Half
Sq.Ft.:
3,504
Status:
Active
MLS#:
MDKE2005930
Type:
Single Family, Single Family-Detached
Subdivision:
COVENTRY FARMS
Lot size:
0.28 Acres
Year built:
2007
Courtesy: Doug Ashley Realtors, LLC
View additional info

311 Devon Drive is located in Coventry Farms; and being located within the Chestertown town limits offers town utilities. The front entrance welcomes you with an open two-story foyer to the second-floor balcony. To the left of the front foyer is a den and to the right is a formal dining room. The foyer hall leads into a large open area that includes a large eat-in kitchen, sunroom and family room with a gas fireplace. The home's design features an abundance of natural light due to its 9-foot ceilings and full-height glass walls on the first floor's rear. The sunroom and first floor primary suite access onto the rear deck with the view and privacy of mature trees. There is a primary bedroom suite on each level; and with there being three additional bedrooms, makes a total of five bedrooms or extra rooms for whatever the need may be. The home offers a garage as well as a full unfinished walk-out basement. The pictures prove the true beauty and spaciousness of this home. (room dimensions are approximate)

Beds:
4
Baths:
3 Full
Sq.Ft.:
2,400
Status:
Active
MLS#:
MDQA2015520
Type:
Single Family, Single Family-Detached
Subdivision:
BLAKEFIELD
Lot size:
1 Acres
Year built:
2025
Courtesy: Chesapeake Real Estate Associates, LLC
View additional info

Discover the charm of this stunning new construction home in the desirable Blakefield community, completed in 2025. This beautifully designed Colonial-style residence boasts 4 spacious bedrooms and 3 full bathrooms, offering ample space for relaxation and entertainment. The kitchen is a chef's dream, featuring an island, eat-in space, and modern appliances including a built-in microwave, dishwasher, electric oven/range, and refrigerator. Enjoy cozy breakfasts in the bright breakfast area or host formal dinners in the separate dining room. The luxurious touches continue with walk-in closets, a convenient upper-floor laundry, and a family room that flows effortlessly from the kitchen and a separate office making this a great option for those who work from home. A first floor bedroom is idea for a guest room, play room, in-law quarters and more. The home is adorned with luxury vinyl plank flooring and plush carpeting, creating a warm and welcoming atmosphere throughout. Set on a generous 1-acre lot that adjoins open space, this property offers a serene outdoor setting, perfect for enjoying nature or future landscaping projects. The side-entry attached garage provides easy access and additional storage. With its excellent condition and thoughtful design, this home is ready to embrace new memories. Experience the perfect blend of comfort and modern living in this exceptional property. Buy with ease when purchasing this new construction home. Seller can'tt settle until January 2026

Open House:

Saturday, 12/6 11:00-1:00PM

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,034
Status:
Active
MLS#:
MDQA2015570
Type:
Single Family, Single Family-Detached
Subdivision:
SARAH SKIPPER LANDS
Lot size:
0.34 Acres
Year built:
1971
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Welcome to 121 Primrose Road, a spacious two-story residence offering 2,034 square feet on a .345-acre lot. This well-built home delivers comfort, functionality, and potential in a peaceful setting just outside downtown Chestertown. Inside, youll find three bedrooms and two full baths upstairs plus a convenient half bath on the main level. The main floor features a bright living area, a classic dining space, and a large all-seasons room off the kitchen-perfect for gatherings or relaxing year-round. The full basement offers a blank slate, ready to finish as a recreation room, workshop, or extra storage. A brand-new septic system provides peace of mind, while the attached two-car garage and expansive back deck add everyday convenience. Situated on the Queen Annes County side of Chestertown, this property keeps you close to the shops, restaurants, and waterfront charm of downtown while offering the privacy of a quiet neighborhood.

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
1,936
Status:
Active
MLS#:
MDKE2005928
Type:
Single Family, Single Family-Detached
Subdivision:
THE VILLAGE AT CHESTERTOWN
Lot size:
0.09 Acres
Year built:
2023
Courtesy: Cross Street Realtors LLC
View additional info

Beautifully done! A MUST see! UPGRADED 2023-built Smart Home, tucked into a quiet and friendly Chestertown community. Thoughtfully enhanced throughout, the kitchen shines with new quartz countertops, a stylish backsplash, upgraded sink and faucet, and added cabinetry with elegant hardware. Fresh light fixtures bring a warm glow to the living spaces, while the laundry room offers added function with quartz surfaces and extra storage. The powder room has been transformed with a stunning vanity and modern fixtures. The second floor offers four spacious bedrooms and two full baths. As a bonus, this property is a smart home, offering comfort and convenience at your fingertips. Just a short drive to multiple marinas in Rock Hall and an easy drive to Philadelphia and Washington, D.C.

Beds:
2
Baths:
1 Full/1 Half
Sq.Ft.:
920
Status:
Active
MLS#:
MDKE2005906
Type:
Single Family, Single Family-Detached
Subdivision:
NONE AVAILABLE
Lot size:
0.13 Acres
Year built:
1980
Courtesy: Select Land & Homes, LLC
View additional info

This 2-bedroom, 1.5-bath bungalow offers a bright, open layout with updates throughout. The home features a sun-filled front room, an eat-in kitchen with new butcher block seating and updated appliances, and a fully renovated bathroom with new tile and a modern vanity. A rear utility room with laundry provides extra storage and access to a small backyard-perfect for gardening or relaxing outdoors. Located within walking distance to Downtown Chestertowns restaurants, shops, farmers market, and waterfront, this property is a great opportunity to enjoy convenient in-town living.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,980
Status:
Active
MLS#:
MDKE2005894
Type:
Condo
Subdivision:
CHESTER RIVER LANDING
Courtesy: Gunther-McClary Real Estate
View additional info

**To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area-perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to the private balcony. Two additional bedrooms share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. Catch a glimpse of the Chester River from the front porch or upper covered balcony, the perfect place to enjoy morning coffee or evening cocktails. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

Beds:
3
Baths:
3 Full/1 Half
Sq.Ft.:
2,092
Status:
Active
MLS#:
MDKE2005892
Type:
Condo
Subdivision:
CHESTER RIVER LANDING
Courtesy: Gunther-McClary Real Estate
View additional info

**To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area-perfect for entertaining. There's also a private study, which could be used as additional space for guests. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and sliding doors to the second floor balcony. There are two additional bedrooms, each with their own full bathroom. the upstairs is complemented by a convenient second-floor laundry. This home is designed with future needs in mind, offering the option of a residential elevator for effortless access to all levels. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,231
Status:
Active
MLS#:
MDKE2005768
Type:
Condo, Single Family-Detached
Subdivision:
CHESTER RIVER LANDING
Courtesy: Gunther-McClary Real Estate
View additional info

**To be built! Welcome to this beautifully designed 2,231 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room, with gas fireplace ,to the gourmet kitchen and dining area-perfect for entertaining. Upstairs, the primary suite features a spa-like bath, walk-in closets, and doors to the private waterfront deck. Two additional bedrooms share a full bath. the upstairs is complemented by a convenient second-floor laundry. Enjoy broad water views and breathtaking sunrises over the Chester River. The covered porch and expansive windows create a seamless connection to the outdoors, enhancing the waterfront lifestyle of this sought-after community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! Nestled in the sought-after Chester River Landing community, this home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

Open House:

Saturday, 12/6 12:00-2:00PM

Beds:
5
Baths:
4 Full/1 Half
Sq.Ft.:
3,243
Status:
Active
MLS#:
MDKE2005890
Type:
Single Family, Single Family-Detached
Subdivision:
CHESTERTOWN HISTORIC DISTRICT
Lot size:
0.06 Acres
Year built:
1863
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

This masterpiece is finally complete. Rebuilt in 1863, the Tilley Residence showcases classic Second Empire style on one of Chestertowns most prominent corners, neighboring Widehall and the Custom House. Expertly restored in 2024-2025 by one of Kent Countys premier builders, the home offers new HVAC, electrical, plumbing, roofing, flooring, and a refreshed open layout. Custom kitchen and baths balance modern comfort with timeless character. A grand three-story staircase and arched entryways welcome you inside. The front porch overlooks town and offers water views. The primary suite includes a fireplace, walk-in closet, and a tiled shower room with views from two sides. The Mansard roof provides a full third floor, and the basement includes a great wine cellar opportunity plus ample storage. A fenced rear yard, off-street parking, and a detached garage complete this rare offering-historic charm blended with modern amenities.

Beds:
4
Baths:
2 Full
Sq.Ft.:
1,325
Status:
Active
MLS#:
MDKE2005848
Type:
Single Family, Single Family-Detached
Subdivision:
CHESTERTOWN
Lot size:
0.41 Acres
Year built:
1960
Courtesy: Cummings & Co. Realtors
View additional info

Welcome to 304 Hadaway Dr. This classic home has been completely reimagined and is ready for it's next chapter. Entering the home you will immediately notice the beautifully refinished original hardwood floors. As you make your way down the hallway past the newly renovated hall bath with custom tile and designer fixtures, you will find 3 spacious bedrooms. The large family room transitions into a perfectly sized dining room and conveniently placed laundry center. The kitchen is absolutely stunning, with stainless Steele appliances, granite countertops, 42" cabinets and new hardwood floors. Moving into the large primary en suit bedroom, you will fall in love with the spa like bath with a large granite vanity, custom tiled stand up shower and tile floors. The home has a brand new 30 year architectural shingle roof, new windows, furnace, water heater, flush mount lights and the whole house has been painted on the interior and exterior with Sherwin Williams designer color collection. Enjoy the large and lush front and back yards, and large driveway. All within walking distance to Washington College and the beautiful and historic town of Chestertown.

Open House:

Sunday, 12/7 10:00-12:00PM

Beds:
4
Baths:
2 Full
Sq.Ft.:
1,656
Status:
Active
MLS#:
MDKE2005876
Type:
Single Family, Single Family-Detached
Subdivision:
CHESTERTOWN HISTORIC DISTRICT
Lot size:
0.15 Acres
Year built:
1916
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Motivated sellers - bring us an offer! This historic 1916 home is charming inside and out. They dont build houses like this anymore! Featuring 4 bedrooms and 2 full baths, this home is adjacent to Washington College and a short stroll to downtown Chestertown. Three finished levels and high ceilings make the home feel roomier than the square footage suggests. Gorgeous original heart-pine hardwood floors and beautiful molding run throughout. The mahogany-floored porch has interchangeable screens and windows, easily converting from a screen porch into a sunroom. New 6 pressure-treated pine fence provides privacy in the backyard, perfect for children or pets to enjoy. Adjacent to the fence, the lot also has a driveway with off-street parking for two vehicles. Calling those with green thumbs - a separate fenced garden is ready for your flowers, fruits, and veggies to be planted this spring! In summer 2025, owners completed $60,000 in updates, including a new roof and fully updated electrical wiring as well as fresh interior paint. (As the electrician noted, much to his chagrin, this house is SOLIDLY built - plaster walls were difficult to get through - and have since been professionally patched!) All upgrades were intended to be enjoyed by current homeowners, but they are regretfully moving to be closer to a new job. After updates, home appraised for over $500,000. Instant equity for a lucky buyer!

Open House:

Saturday, 12/13 12:00-3:00PM

Beds:
3
Baths:
2 Full
Sq.Ft.:
960
Status:
Active
MLS#:
MDKE2005842
Type:
Single Family, Single Family-Detached
Subdivision:
WASHINGTON PARK
Lot size:
0.49 Acres
Year built:
1966
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Kent County welcomes you with a move-in ready home thats full of updates! This 3-bedroom, 2-bath home sits on nearly a half-acre and is just minutes from downtown Chestertown. Enjoy peace of mind with a newer roof (approximately 5 years old), central heat and air, and a tankless water heater. The home features updated bathrooms, fresh interior paint, and a large laundry room with abundant shelving and space for storage. Outside, youll find a spacious yard, storage shed, and access to a wonderful community park with a pavilion and basketball courts. A great combination of comfort, convenience, and value in a desirable location! Kent County has 21 marinas, all within minutes of this location. Live, work and play here in Kent County!

Beds:
6
Baths:
5 Full
Sq.Ft.:
4,954
Status:
Active
MLS#:
MDKE2005866
Type:
Single Family, Single Family-Detached
Subdivision:
MELITOTA
Lot size:
65.47 Acres
Year built:
1858
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Gobbler Hill, circa 1858 with an addition built in 1989, sits like a jewel atop one of the highest points in Kent County. Listed on the National Historic Registry, the transitional architecture is an excellent example of late Greek Revival to early Italianate. The property consists of four parcels totaling over 65 acres. Wildlife abounds on the fields of native prairie grasses, wild flowers, woods, approximately 20 tilled acres and a large pond. Impeccable attention was payed to maintaining the historic character of both the interior and exterior. From the Lincrusta wall covering, 19th century faux wood finishing, plaster medallions, white and sugar pine wood floors and crown molding on the 11 ft. ceilings to the monumental copper roof, the thoughtful restoration is stunning. The newer addition beautifully blends into the original section adding modern conveniences and natural light. The library boasts black walnut bookshelves constructed by a local craftsman. Well maintained grounds offer gardens, mature trees, a classic poured concrete in ground pool with inlaid tile and stunning views. This unique, lovingly restored piece of Kent County history is now looking for a new steward to guide it into its next chapter.

Beds:
6
Baths:
5 Full
Sq.Ft.:
4,954
Status:
Active
MLS#:
MDKE2005852
Type:
Single Family, Single Family-Detached
Subdivision:
MELITOTA
Lot size:
65.47 Acres
Year built:
1858
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Gobbler Hill, circa 1858 with an addition built in 1989, sits like a jewel atop one of the highest points in Kent County. Listed on the National Historic Registry, the transitional architecture is an excellent example of late Greek Revival to early Italianate. The property consists of four parcels totaling over 65 acres. Wildlife abounds on the fields of native prairie grasses, wild flowers, woods, approximately 20 tilled acres and a large pond. Impeccable attention was payed to maintaining the historic character of both the interior and exterior. From the Lincrusta wall covering, 19th century faux wood finishing, plaster medallions, white and sugar pine wood floors and crown molding on the 11 ft. ceilings to the monumental copper roof, the thoughtful restoration is stunning. The newer addition beautifully blends into the original section adding modern conveniences and natural light. The library boasts black walnut bookshelves constructed by a local craftsman. Well maintained grounds offer gardens, mature trees, a classic poured concrete in ground pool with inlaid tile and stunning views. This unique, lovingly restored piece of Kent County history is now looking for a new steward to guide it into its next chapter.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,216
Status:
Active
MLS#:
MDKE2005818
Type:
Single Family, Single Family-Detached
Subdivision:
NONE AVAILABLE
Lot size:
0.07 Acres
Year built:
1900
Courtesy: Cross Street Realtors LLC
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Charming Move-In Ready Colonial in the Heart of Town This beautifully updated Colonial blends timeless character with modern comfort. Ideally located within walking distance of local restaurants, shops, and the scenic waterfront, it offers the perfect combination of charm and convenience. The exterior showcases classic Colonial appeal with vibrant shutters, fresh paint, new roof, gutters, doors, and Andersen double-hung tilting sash windows.The welcoming front porch overlooks manicured flower beds that enhance curb appeal, while the private backyard provides the perfect setting for weekend gatherings and cookouts or just outdoor relaxation. Inside, the home has been thoughtfully renovated from top to bottom. Recent updates include a Mitsubishi Mini-Split heating and cooling system,Rinnai propane instant hot water heater, and 200-amp electrical service with all-new wiring, fixtures, and recessed lighting throughout. The kitchen is a true showstopper that is completely transformed with new cabinetry, quartz countertops, a center island, stainless steel appliances, and a vented range hood. Refinished rustic hardwood floors run throughout the main level, seamlessly blending old world craftsmanship with modern design. A separate Laundry room features a new washer and dryer with Electric Hookups. Upstairs, youll find comfortable bedrooms with Shaw carpeting and pet-proof padding and a beautifully updated bathrooms featuring tiled walls and floors, new vanity, and modern fixtures. The dry basement offers a wide step entrance from Laundry Room with excellent storage space, a new 200-amp electric panel, vapor barrier, and plenty of room for a workshop or home gym or Man Cave. Enjoy the best of in-town living with everything you need just a short stroll away. Schedule your tour today and fall in love with this move-in ready gem

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
2,524
Status:
Active
MLS#:
MDKE2005850
Type:
Single Family, Single Family-Detached
Subdivision:
TOLCHESTER
Lot size:
1.37 Acres
Year built:
1979
Courtesy: Doug Ashley Realtors, LLC
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Two Story Colonial on 1.37+/- acre lot, rectangular 200 x 300 ft. Approximately 2,700 sq ft. of living area in house (estimate). 4 bedrooms, 2.5 Bathrooms. ½ basement with laundry room and fix-it shop/work bench with 2 crawl spaces. Attached two-car garage with abundant built-in shelving and free-standing cabinets for lots of storage space with garage door opener on each of 2 doors. Forced Hot Air, Fuel Oil Heating; Central Air Conditioning. Well water pump upgraded in 2016. New, top-of-the-line â??Meyersâ? well pump, with increased HP. Public sewer so no septic systems to deal with. Four upstairs Bedrooms. The MBR and BR2 are huge. MBR has slider door to lovely Sunroom/Sitting room. The MBR features wainscotting on all walls; crown molding; custom wide molding around all 3 doors and the closet with remote controlled ceiling fan with dimmable light. Large living room with stunning fireplace. Wide, extra-long mantle, matching storage cabinets on both sides of fireplace, large picture window and crown molding. Two full bathrooms with showers are upstairs, each with new, in 2024, quiet, yet powerful Panasonic exhaust fan and LED light. One Powder Room is downstairs. Bright and airy, extra-long dining room. Tray ceiling. dimmable LED ceiling lights on separate, inner and outer ring circuits for versatility. Ceiling centerline is pre-wired (includes 3-way switches) for one or more chandelier lights; Pass-through window to kitchen with fancy tempered glass shelf. Family room with dropped ceiling bar area. Bar sink, granite counters, gorgeous glass door cabinets, wood-burning stove, versatile lighting, and a slider door to a the main level sunroom. Modern, ample-sized kitchen with movable island. Nearly new, upscale glass cooktop/oven, dishwasher and microwave. Build-in refrigerator surrounded by cabinets. Double sink, disposal and PC workstation with shelving matching cabinet. Extraordinary lighting includes under and over cabinet lights plus a ceiling fan with fancy light globes and attractive light globes over sink. MAJOR ADDITION & REHAB done in 2013: Extended DR by 13 feet and added 2nd story sunroom/sitting room on top of DR extension Total rehab of 1st floor sunroom. Top quality, long lasting architectural roof shingle for entire house; new flashing and roof vent seals. Both sunrooms have attractive, casement-style windows for exceptional ventilation. Seven Ceiling fans with attractive lighting: MBR, BR2, BR3, 2nd story sunroom/sitting room, kitchen and 2 on the porch. All four Slider Doors (servicing the porch and the 2 sunrooms) have built-in blinds for privacy and versatile light and view control. Spacious screened porch with porch swing. Massive stone and paver patio area includes three 10x10 ft flat, paved areas for table & chairs. Large Campfire ring within the patio. Two lovely, Amish garden sheds in excellent condition and loaded with options: 12x16 ft. shed installed in 2010, and a 10x14 ft. shed installed in 2021. Huge 16x18 ft. Raised Deck using long-life Trex engineered planks; custom Pergola over one corner. Deep Shaded, 10 x 12 ft Outer Patio Area with Pergola. Mature Trees for great privacy and shade, especially around property perimeter. Three-level, split rail fence on rear and side yard property lines. (Left-side fence only is owned and maintained by the neighbor.) Extra-Wide Driveway. Paved Parking for 10 vehicles! Also suitable for camping trailer or boat.

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