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Discover a prime investment opportunity in the sought-after Coventry Farms subdivision! This charming Colonial-style home, built in 2010, boasts 2,886 square feet of potential, featuring 4 spacious bedrooms and 2.5 bathrooms. With an good property condition, this residence is a blank canvas ready for your personal touch or strategic upgrades, ensuring a strong return on investment. The property includes a walkout basement with outside entrance, offering additional space that can be transformed into a rental unit or recreational area, significantly increasing its value. The cozy gas fireplace adds warmth and charm, making it an inviting space for future tenants or buyers. Situated on a generous 0.27-acre corner lot, this home provides ample outdoor space for entertaining or future enhancements, such as landscaping or outdoor living areas. The attached garage and driveway parking for four vehicles enhance convenience, appealing to a broad range of potential renters or buyers. With a low association fee covering common area maintenance, you can enjoy hassle-free ownership while benefiting from the community's amenities. The location offers easy access to local attractions, ensuring high demand for rental opportunities. Invest in a property that not only promises comfort and style but also the potential for significant financial returns. This home is a great way to buy low and make it your own. Certainly is not beyond homeowner fixes. Don't miss out on this exceptional opportunity to grow your real estate portfolio in a thriving neighborhood!

4 Beds ⋅ 3 Baths

Discover a prime investment opportunity in the sought-after Coventry Farms subdivision! This charming Colonial-style home, built in 2010, boasts 2,886 square feet of potential, featuring 4 spacious bedrooms and 2.5 bathrooms. With an good property condition, this residence is a blank canvas ready for your personal touch or strategic upgrades, ensuring a strong return on investment. The property includes a walkout basement with outside entrance, offering additional space that can be transformed into a rental unit or recreational area, significantly increasing its value. The cozy gas fireplace adds warmth and charm, making it an inviting space for future tenants or buyers. Situated on a generous 0.27-acre corner lot, this home provides ample outdoor space for entertaining or future enhancements, such as landscaping or outdoor living areas. The attached garage and driveway parking for four vehicles enhance convenience, appealing to a broad range of potential renters or buyers. With a low association fee covering common area maintenance, you can enjoy hassle-free ownership while benefiting from the community's amenities. The location offers easy access to local attractions, ensuring high demand for rental opportunities. Invest in a property that not only promises comfort and style but also the potential for significant financial returns. This home is a great way to buy low and make it your own. Certainly is not beyond homeowner fixes. Don't miss out on this exceptional opportunity to grow your real estate portfolio in a thriving neighborhood!

201 Garland Way, Chestertown

Listing courtesy of ERA Martin Associates. Contact:

$1,125,000

This 1925 classic colonial, three story residence, with both front and back gardens, is uniquely situated in the center of the favored 100 block of North Water Street, in historic Chestertown. The formal main entry, with dual brick steps approaches a generous landing, faces away from the street. At first a curiosity until you learn that a prominent family discovered the architectural plans for their "dream house" would not fit horizontally to face the prized road. During its' 100-plus years of life, the front porch (or was it the side?) was converted to a remarkable library, with requisite bookcases, and enjoys light from three sides. The formal parlor, with wood-burning fireplace and reclaimed 19th century moldings and mantle, is left of the straight-through center hall with classic black and white porcelain tiles. The intimate, yet well-proportioned dining room enhances the exceptional flow of the first-floor public rooms. A discreetly positioned powder room and butler's pantry with window and original cabinetry is conveniently placed before entering the large and sunny kitchen with premium custom cabinetry, appliances and finishes from a 2012 renovation. Two distinct patios, one screened and accessed from the dining room and the other from kitchen, overlook the large, rear garden with mature trees and landscaping. The center stairs, with a palladium window bathing light onto the steps, takes you to the first of two oversized landings that have served many lifestyle-uses over the years. The water view primary suite was renovated in 2022 by locally acclaimed Taylor Loughry LLC and boasts a timeless, luxurious aesthetic with custom built closets and Waterwork bath fixtures. Two additional bedrooms and refreshed bath with Restoration Hardware finishes, occupy the second floor. The third floor, with its own generous landing gives access to an ensuite bedroom with walk-in windowed closet (perfect for a future cedar lined closet) and a substantial sized fifth bedroom or multi-purpose space facing the Chester River and exquisite neighboring architecture. Rear yard might accommodate a pool.

5 Beds ⋅ 4 Baths

This 1925 classic colonial, three story residence, with both front and back gardens, is uniquely situated in the center of the favored 100 block of North Water Street, in historic Chestertown. The formal main entry, with dual brick steps approaches a generous landing, faces away from the street. At first a curiosity until you learn that a prominent family discovered the architectural plans for their "dream house" would not fit horizontally to face the prized road. During its' 100-plus years of life, the front porch (or was it the side?) was converted to a remarkable library, with requisite bookcases, and enjoys light from three sides. The formal parlor, with wood-burning fireplace and reclaimed 19th century moldings and mantle, is left of the straight-through center hall with classic black and white porcelain tiles. The intimate, yet well-proportioned dining room enhances the exceptional flow of the first-floor public rooms. A discreetly positioned powder room and butler's pantry with window and original cabinetry is conveniently placed before entering the large and sunny kitchen with premium custom cabinetry, appliances and finishes from a 2012 renovation. Two distinct patios, one screened and accessed from the dining room and the other from kitchen, overlook the large, rear garden with mature trees and landscaping. The center stairs, with a palladium window bathing light onto the steps, takes you to the first of two oversized landings that have served many lifestyle-uses over the years. The water view primary suite was renovated in 2022 by locally acclaimed Taylor Loughry LLC and boasts a timeless, luxurious aesthetic with custom built closets and Waterwork bath fixtures. Two additional bedrooms and refreshed bath with Restoration Hardware finishes, occupy the second floor. The third floor, with its own generous landing gives access to an ensuite bedroom with walk-in windowed closet (perfect for a future cedar lined closet) and a substantial sized fifth bedroom or multi-purpose space facing the Chester River and exquisite neighboring architecture. Rear yard might accommodate a pool.

108 N Water St, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

$349,900

Investor Alert in Historic Downtown Chestertown! Fully Occupied Triplex. Units offer hardwood floors, mini splits to units 1 and 2, a new bathroom in unit 3 and kitchen upgrades n unit 2 including new counter tops and flooring

501 High St, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$365,000

Enjoy the best of both worlds with this well-maintained home situated on a generous 0.653-acre lot just outside of Chestertown! Offering the space and privacy of country living while remaining just minutes from downtown amenities, this 3-bedroom, 2.5-bath home has plenty to offer. **A brand-new well and septic system have just been installed**, providing an important recent improvement for the next owner. Inside, you'll find a welcoming entryway, formal dining room, and spacious kitchen featuring an island, gas cooktop, and cozy breakfast nook. The dedicated laundry room offers convenient access to the side yard, while the comfortable living room provides a warm gathering space centered around a working fireplace. A mix of wood, tile, and carpet flooring adds character throughout the home, and two bathrooms have been recently updated. Outside, enjoy the expansive backyard with room to relax, entertain, or simply take in the extra space. The detached two-car garage offers additional flexibility with a separate area ideal for a workshop, home office, or hobby space, along with a loft ready for your ideas. With a new well and septic system and a convenient location just outside of town, this property offers space, versatility, and the opportunity to enjoy Eastern Shore living close to everything Chestertown has to offer!

3 Beds ⋅ 3 Baths

Enjoy the best of both worlds with this well-maintained home situated on a generous 0.653-acre lot just outside of Chestertown! Offering the space and privacy of country living while remaining just minutes from downtown amenities, this 3-bedroom, 2.5-bath home has plenty to offer. **A brand-new well and septic system have just been installed**, providing an important recent improvement for the next owner. Inside, you'll find a welcoming entryway, formal dining room, and spacious kitchen featuring an island, gas cooktop, and cozy breakfast nook. The dedicated laundry room offers convenient access to the side yard, while the comfortable living room provides a warm gathering space centered around a working fireplace. A mix of wood, tile, and carpet flooring adds character throughout the home, and two bathrooms have been recently updated. Outside, enjoy the expansive backyard with room to relax, entertain, or simply take in the extra space. The detached two-car garage offers additional flexibility with a separate area ideal for a workshop, home office, or hobby space, along with a loft ready for your ideas. With a new well and septic system and a convenient location just outside of town, this property offers space, versatility, and the opportunity to enjoy Eastern Shore living close to everything Chestertown has to offer!

24607 Chestertown Rd, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

$425,000

Nestled in Coventry Farms II, this exquisite Colonial-style residence offers a harmonious blend of Space, Convenience and comfort, perfect for those who appreciate the finer things in life. Built in 2009, this stunning home boasts 3,165 square feet of meticulously designed living space, ensuring ample room for both relaxation and entertainment. Step inside to discover an inviting interior adorned with high-end finishes and thoughtful details. The spacious family room, seamlessly connected to the kitchen, is perfect for gatherings, while the formal dining room sets the stage for elegant dinner parties. The gourmet kitchen is a chef's dream, featuring a generous island, stainless steel appliances, and a convenient pantry, all bathed in natural light from the double-pane windows. Enjoy casual meals in the cozy breakfast area, where morning sunlight creates a warm ambiance. Retreat to the luxurious primary suite, complete with a walk-in closet with an additional closet and a spa-like bathroom featuring a walk-in shower and double sinks. Each of the additional three bedrooms offers generous space and comfort and large closets, ensuring everyone has their own sanctuary. Recessed lighting and ceiling fans throughout enhance the home's inviting atmosphere, while plush carpeting and laminate flooring provide a perfect balance of style and practicality. The partially finished basement offers endless possibilities, whether you envision a home theater, gym, or additional living space. The basement even has a rough in for an additional bathroom. With interior access and heating, this area is ready to be transformed into your personal oasis. Outside, the property sits on a 0.28-acre lot that backs to serene trees, while the front over looks the large common area providing a tranquil backdrop for outdoor living. The expansive deck invites you to unwind and entertain, while the attached garage and ample driveway space accommodate all your vehicles with ease. This home is not just a residence; it's a lifestyle. Enjoy the peace of mind that comes with living in a well-established community, where every detail has been considered for your comfort and enjoyment. Experience the perfect blend of luxury, convenience, and nature in this exceptional Coventry Farms II gem that is "Move In Ready". Enjoy a walk in Downtown Historical Chestertown which is on the Chester River. Explore many events that the town has such as Saturday morning Farmers Markets, The Annual Tea Party, Downrigging Festival, Fourth of July Fireworks, tours on the Sultana and River Packet and Dickens of a Christmas or just relax on a bench by the River or Wilmer Park. Don't miss the opportunity to make this dream home your reality! Chestertown is a great place to call Home!

4 Beds ⋅ 3 Baths

Nestled in Coventry Farms II, this exquisite Colonial-style residence offers a harmonious blend of Space, Convenience and comfort, perfect for those who appreciate the finer things in life. Built in 2009, this stunning home boasts 3,165 square feet of meticulously designed living space, ensuring ample room for both relaxation and entertainment. Step inside to discover an inviting interior adorned with high-end finishes and thoughtful details. The spacious family room, seamlessly connected to the kitchen, is perfect for gatherings, while the formal dining room sets the stage for elegant dinner parties. The gourmet kitchen is a chef's dream, featuring a generous island, stainless steel appliances, and a convenient pantry, all bathed in natural light from the double-pane windows. Enjoy casual meals in the cozy breakfast area, where morning sunlight creates a warm ambiance. Retreat to the luxurious primary suite, complete with a walk-in closet with an additional closet and a spa-like bathroom featuring a walk-in shower and double sinks. Each of the additional three bedrooms offers generous space and comfort and large closets, ensuring everyone has their own sanctuary. Recessed lighting and ceiling fans throughout enhance the home's inviting atmosphere, while plush carpeting and laminate flooring provide a perfect balance of style and practicality. The partially finished basement offers endless possibilities, whether you envision a home theater, gym, or additional living space. The basement even has a rough in for an additional bathroom. With interior access and heating, this area is ready to be transformed into your personal oasis. Outside, the property sits on a 0.28-acre lot that backs to serene trees, while the front over looks the large common area providing a tranquil backdrop for outdoor living. The expansive deck invites you to unwind and entertain, while the attached garage and ample driveway space accommodate all your vehicles with ease. This home is not just a residence; it's a lifestyle. Enjoy the peace of mind that comes with living in a well-established community, where every detail has been considered for your comfort and enjoyment. Experience the perfect blend of luxury, convenience, and nature in this exceptional Coventry Farms II gem that is "Move In Ready". Enjoy a walk in Downtown Historical Chestertown which is on the Chester River. Explore many events that the town has such as Saturday morning Farmers Markets, The Annual Tea Party, Downrigging Festival, Fourth of July Fireworks, tours on the Sultana and River Packet and Dickens of a Christmas or just relax on a bench by the River or Wilmer Park. Don't miss the opportunity to make this dream home your reality! Chestertown is a great place to call Home!

106 Harlan Loop, Chestertown

Listing courtesy of Douglas Realty LLC. Contact:

$224,900

Welcome to 28036 Creamery Street in Kennedyville. Built in 1920, this two-story home offers 3 bedrooms, 1 full bath and 1,296 square feet of living space, along with two parcels totaling approximately .224 acre. The main level features a large kitchen with a sightline into the dining room, living room, full bath, and a convenient laundry/utility area located just off the dining room. All three bedrooms are located on the upper level. The home is functional and ready for its next owner, while also offering an opportunity for buyers who would like to make improvements and updates over time to suit their own style. The sale includes the .109-acre homesite plus an adjoining .115-acre parcel, providing additional outdoor space and possibilities. Located in the Eastern Shore community of Kennedyville, the property is a short drive to historic Chestertown for shopping, dining and everyday conveniences. Enjoy access to the area's outdoor recreation, including the Sassafras River, Turner's Creek and Sassafras Natural Resources Management Area, with opportunities for boating, fishing, kayaking and hiking. Betterton and Rock Hall provide additional Chesapeake Bay destinations within the surrounding area. Routes 213 and 301 also provides connections toward Middletown, Dover and surrounding employment and shopping areas. Property is being sold As-Is.

3 Beds ⋅ 1 Baths

Welcome to 28036 Creamery Street in Kennedyville. Built in 1920, this two-story home offers 3 bedrooms, 1 full bath and 1,296 square feet of living space, along with two parcels totaling approximately .224 acre. The main level features a large kitchen with a sightline into the dining room, living room, full bath, and a convenient laundry/utility area located just off the dining room. All three bedrooms are located on the upper level. The home is functional and ready for its next owner, while also offering an opportunity for buyers who would like to make improvements and updates over time to suit their own style. The sale includes the .109-acre homesite plus an adjoining .115-acre parcel, providing additional outdoor space and possibilities. Located in the Eastern Shore community of Kennedyville, the property is a short drive to historic Chestertown for shopping, dining and everyday conveniences. Enjoy access to the area's outdoor recreation, including the Sassafras River, Turner's Creek and Sassafras Natural Resources Management Area, with opportunities for boating, fishing, kayaking and hiking. Betterton and Rock Hall provide additional Chesapeake Bay destinations within the surrounding area. Routes 213 and 301 also provides connections toward Middletown, Dover and surrounding employment and shopping areas. Property is being sold As-Is.

28036 Creamery St, Kennedyville

Listing courtesy of BHHS Fox & Roach-Christiana. Contact:

$259,900

Ask about our SELLER-PAID RATE BUYDOWN — the builder is paying to permanently lower your interest rate when you finance with our preferred lender, who is also contributing toward your closing costs. The result: a dramatically lower monthly payment on a brand-new home, saving you well over a hundred dollars every month — even more on lower-down-payment financing. This is real payment relief in today's market — often the difference between watching and owning. Brand-new construction in the heart of Chestertown. Buydown applies with use of preferred lender; see agent for details. 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. Additional highlights include exclusive financing opportunities with zero down payment loans, paid closing cost programs, and discounted interest rates—making it possible to own this home 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. Ask about Special Financing Offers and how to get $7,500 or more in closing help from the builder's preferred lender and on select models, while they last!

3 Beds ⋅ 3 Baths

Ask about our SELLER-PAID RATE BUYDOWN — the builder is paying to permanently lower your interest rate when you finance with our preferred lender, who is also contributing toward your closing costs. The result: a dramatically lower monthly payment on a brand-new home, saving you well over a hundred dollars every month — even more on lower-down-payment financing. This is real payment relief in today's market — often the difference between watching and owning. Brand-new construction in the heart of Chestertown. Buydown applies with use of preferred lender; see agent for details. 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. Additional highlights include exclusive financing opportunities with zero down payment loans, paid closing cost programs, and discounted interest rates—making it possible to own this home 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. Ask about Special Financing Offers and how to get $7,500 or more in closing help from the builder's preferred lender and on select models, while they last!

103 Metcalf Rd, Chestertown

Listing courtesy of Real Broker, LLC - Chester. Contact:

$425,000

10k BONUS OFFER!!! NEW CONSTRUCTION in the charming Eastern Shore town of Rock Hall! This beautiful Colonial-style home offers the perfect blend of modern construction, comfortable living, and small-town Eastern Shore charm. Featuring 3 bedrooms, 2 full baths, and 1 half bath, this thoughtfully designed home boasts an inviting open floor plan that creates an easy flow between the living, dining, and kitchen areas. Step inside from the cozy front porch and appreciate the quality and efficiency built into this home. Energy-conscious features include high-efficiency windows and doors, quality insulation, and a professionally conditioned, watertight crawl space designed to provide a cleaner, drier, more efficient foundation for years to come. For added convenience, laundry is located on the top floor, making everyday living and household chores that much easier. Parking is plentiful, with a spacious driveway in the front as well as convenient additional access from the side entrance off Cottage Street. Situated on a large lot, there is plenty of room to enjoy the outdoors and even the potential to add an approximately 1,200-square-foot outbuilding—perfect for a workshop, garage, storage, studio, or other future needs (subject to applicable approvals and zoning). Located in the wonderful waterfront community of Rock Hall, Maryland, you'll be close to the area's marinas, restaurants, shops, and the Chesapeake Bay while enjoying the relaxed lifestyle that makes Rock Hall such a special Eastern Shore destination. Seller to Credit any BUYER 10k towards buyers choice: Purchase price, Seller Assist, Construction of : Deck, Fence, Etc... at time of closing.

3 Beds ⋅ 3 Baths

10k BONUS OFFER!!! NEW CONSTRUCTION in the charming Eastern Shore town of Rock Hall! This beautiful Colonial-style home offers the perfect blend of modern construction, comfortable living, and small-town Eastern Shore charm. Featuring 3 bedrooms, 2 full baths, and 1 half bath, this thoughtfully designed home boasts an inviting open floor plan that creates an easy flow between the living, dining, and kitchen areas. Step inside from the cozy front porch and appreciate the quality and efficiency built into this home. Energy-conscious features include high-efficiency windows and doors, quality insulation, and a professionally conditioned, watertight crawl space designed to provide a cleaner, drier, more efficient foundation for years to come. For added convenience, laundry is located on the top floor, making everyday living and household chores that much easier. Parking is plentiful, with a spacious driveway in the front as well as convenient additional access from the side entrance off Cottage Street. Situated on a large lot, there is plenty of room to enjoy the outdoors and even the potential to add an approximately 1,200-square-foot outbuilding—perfect for a workshop, garage, storage, studio, or other future needs (subject to applicable approvals and zoning). Located in the wonderful waterfront community of Rock Hall, Maryland, you'll be close to the area's marinas, restaurants, shops, and the Chesapeake Bay while enjoying the relaxed lifestyle that makes Rock Hall such a special Eastern Shore destination. Seller to Credit any BUYER 10k towards buyers choice: Purchase price, Seller Assist, Construction of : Deck, Fence, Etc... at time of closing.

5855 Cottage Ave, Rock Hall

Listing courtesy of RE/MAX Point Realty. Contact:

$363,000

Welcome to Galena a little big town. Located just down the road from the Sassafras River this area has excellent access to the Chesapeake Bay, shopping, restaurants and more. With just about an hours drive you can be in Baltimore, Philadelphia or Annapolis. What an opportunity to build instant equity. Spacious home in great community, backing to farmland. This home is located in the community, but not within town limits. Enjoy public utilities without the town tax! Home has been maintained over the years, featuring new HVAC less than a year ago as well as roof replacment 10 years ago. Nicely laid out with living room, dining room, eat in kitchen, laundry room, powder room and great family room on the main level. The second level has a primary suite with loft, two additional bedrooms and hall bath. There is also a nicely proportioned two car attached garage. Home will benefit from updating to make it your own.

3 Beds ⋅ 3 Baths

Welcome to Galena a little big town. Located just down the road from the Sassafras River this area has excellent access to the Chesapeake Bay, shopping, restaurants and more. With just about an hours drive you can be in Baltimore, Philadelphia or Annapolis. What an opportunity to build instant equity. Spacious home in great community, backing to farmland. This home is located in the community, but not within town limits. Enjoy public utilities without the town tax! Home has been maintained over the years, featuring new HVAC less than a year ago as well as roof replacment 10 years ago. Nicely laid out with living room, dining room, eat in kitchen, laundry room, powder room and great family room on the main level. The second level has a primary suite with loft, two additional bedrooms and hall bath. There is also a nicely proportioned two car attached garage. Home will benefit from updating to make it your own.

206 Maplewood Ln, Galena

Listing courtesy of L. C. Parker Real Estate. Contact:

$675,000

This charming American Four Square has been meticulously maintained and is located 1 block from Washington College’s campus and near Chestertown’s Historic District’s shops and restaurants. All of the key features of this architectural style are evident - two and a half stories high, hipped slate roof with a distinctive dormer at the front of the house, spacious four-room plan and full front porch with mahogany flooring with a depth that makes it a wonderful outdoor room. The American Four-Square was designed for narrow urban lots and this property’s bonus is its deep lot that easily accommodated an addition of a kitchen-family room opening onto a deck and a deep rear fully fenced back yard that offers safe play for children and pets. Another bonus is a two-car garage. From the foyer, the “U” shaped artisan stair rises to the third floor and the main floor’s living room, dining room, bathroom and library are seamlessly connected to maximize the rooms’ sizes. The rear addition of an open plan kitchen-family room has easy indoor-outdoor flow to the adjacent deck. The second floor contains 3 bedrooms and 2 full baths as well as the laundry. The third floor contains two additional bedrooms. Throughout the house, details of original wood floors, moldings and trim, corner guards and bespoke millwork evoke an earlier era of gracious living. A uniquely American architectural style, with an addition and updates for today’s family lifestyle; freshly painted exterior, meticulous mature landscaping, fenced rear yard that is a verdant oasis, two-car garage - who could ask for anything more?

5 Beds ⋅ 3 Baths

This charming American Four Square has been meticulously maintained and is located 1 block from Washington College’s campus and near Chestertown’s Historic District’s shops and restaurants. All of the key features of this architectural style are evident - two and a half stories high, hipped slate roof with a distinctive dormer at the front of the house, spacious four-room plan and full front porch with mahogany flooring with a depth that makes it a wonderful outdoor room. The American Four-Square was designed for narrow urban lots and this property’s bonus is its deep lot that easily accommodated an addition of a kitchen-family room opening onto a deck and a deep rear fully fenced back yard that offers safe play for children and pets. Another bonus is a two-car garage. From the foyer, the “U” shaped artisan stair rises to the third floor and the main floor’s living room, dining room, bathroom and library are seamlessly connected to maximize the rooms’ sizes. The rear addition of an open plan kitchen-family room has easy indoor-outdoor flow to the adjacent deck. The second floor contains 3 bedrooms and 2 full baths as well as the laundry. The third floor contains two additional bedrooms. Throughout the house, details of original wood floors, moldings and trim, corner guards and bespoke millwork evoke an earlier era of gracious living. A uniquely American architectural style, with an addition and updates for today’s family lifestyle; freshly painted exterior, meticulous mature landscaping, fenced rear yard that is a verdant oasis, two-car garage - who could ask for anything more?

212 Washington Ave, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

$38,200,000

Tulip Forest, a farm defined by scale, stewardship, and long-term value. Recognized as a premier sporting estate, this legacy holding property is the kind of asset that seldom comes to market on Maryland's Upper Eastern Shore. 1,054 +/- acres held intact under one ownership: 680 tillable acres, 272 acres of timber, 5 ponds, 3 impoundments, 26.75-acre wetlands restoration project, 45 acres CRP, a 3.75 mile interior gravel road system, 3 residences, and multiple farm outbuildings. At its center stands Caulk's Field House, circa 1743, a remarkably preserved residence on the ground recognized among Maryland's best-preserved War of 1812 sites. Nearly four miles of farm roads reach every corner of the property, and the ponds, impoundments, and mature timber hold waterfowl, whitetail and countless other game species. Also included beyond the farming operation: 7 acres zoned commercial, additional parcels zoned Village, and four sewer allocations secured along Georgetown Road. A working farm today, with room to grow, suited to farmers, sportsmen, conservation buyers, and investors.

4 Beds ⋅ 2 Baths

Tulip Forest, a farm defined by scale, stewardship, and long-term value. Recognized as a premier sporting estate, this legacy holding property is the kind of asset that seldom comes to market on Maryland's Upper Eastern Shore. 1,054 +/- acres held intact under one ownership: 680 tillable acres, 272 acres of timber, 5 ponds, 3 impoundments, 26.75-acre wetlands restoration project, 45 acres CRP, a 3.75 mile interior gravel road system, 3 residences, and multiple farm outbuildings. At its center stands Caulk's Field House, circa 1743, a remarkably preserved residence on the ground recognized among Maryland's best-preserved War of 1812 sites. Nearly four miles of farm roads reach every corner of the property, and the ponds, impoundments, and mature timber hold waterfowl, whitetail and countless other game species. Also included beyond the farming operation: 7 acres zoned commercial, additional parcels zoned Village, and four sewer allocations secured along Georgetown Road. A working farm today, with room to grow, suited to farmers, sportsmen, conservation buyers, and investors.

8184 Rock Hall Rd, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

$370,000

Space, convenience, and value just minutes from downtown Chestertown! This spacious 4-bedroom, 2.5-bath Colonial in Coventry Farms checks the boxes for buyers looking for room to spread out without giving up convenience. The main level features a comfortable living room, dining area, kitchen, and half bath. Upstairs, you’ll find four bedrooms, including a spacious primary suite with a walk-in closet and en suite bath with dual vanities. Need even more space? The mostly finished basement adds approximately 600 sq. ft. of flexible living space. Plus the attached two car garage with plenty of room to park your vehicle and still have storage space. Outside, enjoy a stamped-concrete patio and fenced backyard—perfect for relaxing and entertaining. Recent updates include HVAC replaced in 2021, upgraded bathrooms, and additional cabinets and counter space in the kitchen. Just under 2 miles from historic downtown Chestertown, you’ll be close to restaurants, shopping, festivals, walking trail, the waterfront park, and everything town has to offer.

4 Beds ⋅ 3 Baths

Space, convenience, and value just minutes from downtown Chestertown! This spacious 4-bedroom, 2.5-bath Colonial in Coventry Farms checks the boxes for buyers looking for room to spread out without giving up convenience. The main level features a comfortable living room, dining area, kitchen, and half bath. Upstairs, you’ll find four bedrooms, including a spacious primary suite with a walk-in closet and en suite bath with dual vanities. Need even more space? The mostly finished basement adds approximately 600 sq. ft. of flexible living space. Plus the attached two car garage with plenty of room to park your vehicle and still have storage space. Outside, enjoy a stamped-concrete patio and fenced backyard—perfect for relaxing and entertaining. Recent updates include HVAC replaced in 2021, upgraded bathrooms, and additional cabinets and counter space in the kitchen. Just under 2 miles from historic downtown Chestertown, you’ll be close to restaurants, shopping, festivals, walking trail, the waterfront park, and everything town has to offer.

123 Trafford Dr, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$515,000

Welcome to 11960 Flour Mill Street. This is the perfect house for a growing family or a multi-generational household. Main House has 6 full bedrooms and 4 full bathrooms while the second floor above the garage is a spacious mother-in-law suite with a separate entrance, efficiency kitchen, full bath and walk-in closet. First floor has a bedroom and full bath and wide open floor plan in the kitchen and living rooms. Kitchen features stainless steel appliances, granite countertops and wood cabinets. Second floor has 5 bedrooms and 2 full baths. Partially finished full basement has another full bathroom and offers a range of possibilities for the next owner. This home has more room and storage than you could imagine. The Villages at Kennedyville is a quiet, local community. Less than 90 minutes to Philadelphia and Washington D.C. 30 minutes to Middletown, Delaware and tax-free shopping. Close to Turners Creek State Park, Betterton Beach and the restaurants/marinas in Galena on the Sassafras River. Just a few minutes to historic downtown Chestertown. 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. Seller will convey a brand new Carrier HVAC unit with the sale to replace the first floor one.

7 Beds ⋅ 5 Baths

Welcome to 11960 Flour Mill Street. This is the perfect house for a growing family or a multi-generational household. Main House has 6 full bedrooms and 4 full bathrooms while the second floor above the garage is a spacious mother-in-law suite with a separate entrance, efficiency kitchen, full bath and walk-in closet. First floor has a bedroom and full bath and wide open floor plan in the kitchen and living rooms. Kitchen features stainless steel appliances, granite countertops and wood cabinets. Second floor has 5 bedrooms and 2 full baths. Partially finished full basement has another full bathroom and offers a range of possibilities for the next owner. This home has more room and storage than you could imagine. The Villages at Kennedyville is a quiet, local community. Less than 90 minutes to Philadelphia and Washington D.C. 30 minutes to Middletown, Delaware and tax-free shopping. Close to Turners Creek State Park, Betterton Beach and the restaurants/marinas in Galena on the Sassafras River. Just a few minutes to historic downtown Chestertown. 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. Seller will convey a brand new Carrier HVAC unit with the sale to replace the first floor one.

11960 Flour Mill St, Kennedyville

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

$480,000

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!

3 Beds ⋅ 3 Baths

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!

129 Trafford Dr, Chestertown

Listing courtesy of Elevated Real Estate Solutions. Contact:

$259,900

*Open Every Tuesdy and Thursday from 6 to 7pm* 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 ½% ($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.

3 Beds ⋅ 2 Baths

*Open Every Tuesdy and Thursday from 6 to 7pm* 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 ½% ($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.

115 Metcalf Rd, Chestertown

Listing courtesy of Real Broker, LLC - Chester. Contact:

$1,595,000

Enjoy sweeping water views, a bulkheaded shoreline, and a lawn extending to the water's edge—an exceptional and hard-to-find combination. Boating enthusiasts will appreciate the private dock, complete with a boat lift and Jet Ski lift and the location on the river. This charming four-bedroom home blends timeless character with everyday functionality. The thoughtfully designed floor plan features a first-floor primary suite, hardwood floors throughout, and spacious living areas ideal for both relaxing and entertaining. The detached garage includes a private apartment with an additional bedroom and an additional full bathroom, offering excellent space for guests or extended family. Including the garage apartment, this property has 5 bedrooms and 3 full baths, The expansive kitchen and living area open through sliding glass doors to a patio, screened porch, and beautifully landscaped lawn all overlooking the water, creating seamless indoor-outdoor living with broad water views. Mature trees provide shade, beauty, and privacy throughout the property. Conveniently located just minutes from Georgetown, you'll enjoy easy access to restaurants and a sought-after boating destination. Whether your passion is waterskiing, wakeboarding, paddleboarding, fishing, or peaceful kayaking, this location offers endless opportunities to enjoy life on the water. This is a property that truly should be experienced in person to appreciate its unique setting, exceptional amenities, and waterfront lifestyle.

4 Beds ⋅ 2 Baths

Enjoy sweeping water views, a bulkheaded shoreline, and a lawn extending to the water's edge—an exceptional and hard-to-find combination. Boating enthusiasts will appreciate the private dock, complete with a boat lift and Jet Ski lift and the location on the river. This charming four-bedroom home blends timeless character with everyday functionality. The thoughtfully designed floor plan features a first-floor primary suite, hardwood floors throughout, and spacious living areas ideal for both relaxing and entertaining. The detached garage includes a private apartment with an additional bedroom and an additional full bathroom, offering excellent space for guests or extended family. Including the garage apartment, this property has 5 bedrooms and 3 full baths, The expansive kitchen and living area open through sliding glass doors to a patio, screened porch, and beautifully landscaped lawn all overlooking the water, creating seamless indoor-outdoor living with broad water views. Mature trees provide shade, beauty, and privacy throughout the property. Conveniently located just minutes from Georgetown, you'll enjoy easy access to restaurants and a sought-after boating destination. Whether your passion is waterskiing, wakeboarding, paddleboarding, fishing, or peaceful kayaking, this location offers endless opportunities to enjoy life on the water. This is a property that truly should be experienced in person to appreciate its unique setting, exceptional amenities, and waterfront lifestyle.

14046 Tockwogh Ln, Galena

Listing courtesy of Gunther-McClary Real Estate. Contact:

$264,900

*Open Every Tuesday and Thursday from 6 to 7pm* 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.

3 Beds ⋅ 2 Baths

*Open Every Tuesday and Thursday from 6 to 7pm* 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.

121 Metcalf Rd, Chestertown

Listing courtesy of Real Broker, LLC - Chester. Contact:

$310,000

Welcome to this beautifully renovated 2-bedroom, 2-bath home sitting on a very large lot. This home in Rock Hall, a historic harbor town celebrated for its Chesapeake Bay shoreline, boating lifestyle and vibrant coastal charm, features 2 bedrooms, 2 bathrooms and 1200 square feet. It offers luxury vinyl floors, energy efficient windows, a spacious central island with seating, stainless steel appliances, a large back porch for entertaining and a large plot of land to build on if you wish. Experience the charm of this beautifully renovated colonial home in the heart of Kent County, where classic elegance meets modern luxury. Set on a generous 0.21-acre lot, this detached residence has undergone a major renovation in 2026, ensuring a seamless blend of timeless design and contemporary comforts. Step inside to discover a warm and inviting atmosphere, accentuated by high-end finishes throughout. The spacious layout features two well-appointed bedrooms and two full bathrooms, providing ample space for relaxation and rejuvenation. The heart of the home boasts a state-of-the-art kitchen equipped with a built-in microwave, perfect for culinary enthusiasts and entertaining guests. Natural light floods the interior, highlighting the exquisite craftsmanship defines this property. The exterior, adorned with durable vinyl siding, complements the classic colonial architecture, while the crushed stone driveway offers both functionality and curb appeal. Enjoy the tranquility of your surroundings in this peaceful neighborhood, where you can unwind on your private lot, free from the hustle and bustle of city life. With parking for up to three vehicles, convenience is at your fingertips. This home is not just a place to live; it's a lifestyle choice that embodies comfort, elegance, and sophistication. Embrace the opportunity to make this exquisite property your own and indulge in the luxury of modern living in a historic setting. You will be minutes from downtown Rock Hall, where you can enjoy fresh seafood, explore museums and experience the charm of this Eastern Shore town. Whether strolling along the waterfront, enjoying the marina or setting sail on the Bay, this home puts you at the heart of it all.

2 Beds ⋅ 2 Baths

Welcome to this beautifully renovated 2-bedroom, 2-bath home sitting on a very large lot. This home in Rock Hall, a historic harbor town celebrated for its Chesapeake Bay shoreline, boating lifestyle and vibrant coastal charm, features 2 bedrooms, 2 bathrooms and 1200 square feet. It offers luxury vinyl floors, energy efficient windows, a spacious central island with seating, stainless steel appliances, a large back porch for entertaining and a large plot of land to build on if you wish. Experience the charm of this beautifully renovated colonial home in the heart of Kent County, where classic elegance meets modern luxury. Set on a generous 0.21-acre lot, this detached residence has undergone a major renovation in 2026, ensuring a seamless blend of timeless design and contemporary comforts. Step inside to discover a warm and inviting atmosphere, accentuated by high-end finishes throughout. The spacious layout features two well-appointed bedrooms and two full bathrooms, providing ample space for relaxation and rejuvenation. The heart of the home boasts a state-of-the-art kitchen equipped with a built-in microwave, perfect for culinary enthusiasts and entertaining guests. Natural light floods the interior, highlighting the exquisite craftsmanship defines this property. The exterior, adorned with durable vinyl siding, complements the classic colonial architecture, while the crushed stone driveway offers both functionality and curb appeal. Enjoy the tranquility of your surroundings in this peaceful neighborhood, where you can unwind on your private lot, free from the hustle and bustle of city life. With parking for up to three vehicles, convenience is at your fingertips. This home is not just a place to live; it's a lifestyle choice that embodies comfort, elegance, and sophistication. Embrace the opportunity to make this exquisite property your own and indulge in the luxury of modern living in a historic setting. You will be minutes from downtown Rock Hall, where you can enjoy fresh seafood, explore museums and experience the charm of this Eastern Shore town. Whether strolling along the waterfront, enjoying the marina or setting sail on the Bay, this home puts you at the heart of it all.

21232 Rock Hall Ave, Rock Hall

Listing courtesy of RE/MAX Advantage Realty. Contact:

$350,000

Quintessential Rock Hall home with an abundance of charm! Located in the heart of Rock Hall, a short distance to Main Street shops, many fantastic restaurants, and seven marinas. Enjoy evenings and mornings on the screened porch, which runs the expanse of the home. Entering from the porch, you'll find a cosy living room and a galley kitchen with open dining space. This home offers a first-floor bedroom and full bathroom, plus two additional bedrooms and a full bath on the second floor. There's a walk-up attic for additional storage, shed in the yard, laundry and utility room off the kitchen. Many updates have been made throughout the years, such as the addition of a copper roof on the front porch, updated bathrooms, flooring, and updated lighting. Recent updates include the home's heating system. Don't miss this downtown gem!

3 Beds ⋅ 2 Baths

Quintessential Rock Hall home with an abundance of charm! Located in the heart of Rock Hall, a short distance to Main Street shops, many fantastic restaurants, and seven marinas. Enjoy evenings and mornings on the screened porch, which runs the expanse of the home. Entering from the porch, you'll find a cosy living room and a galley kitchen with open dining space. This home offers a first-floor bedroom and full bathroom, plus two additional bedrooms and a full bath on the second floor. There's a walk-up attic for additional storage, shed in the yard, laundry and utility room off the kitchen. Many updates have been made throughout the years, such as the addition of a copper roof on the front porch, updated bathrooms, flooring, and updated lighting. Recent updates include the home's heating system. Don't miss this downtown gem!

21384 E Sharp St, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

$79,000

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.

2 Beds ⋅ 1 Baths

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.

234 N College Ave, Chestertown

Listing courtesy of Cummings & Co Realtors. Contact:

$1,495,000

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.

9 Beds ⋅ 7 Baths

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.

8796 Maryland Pkwy, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

$344,900

NEW PRICE — $344,900! MORE SPACE, MORE FLEXIBILITY & NO HOA! Discover an exceptional opportunity in the charming waterfront town of Rock Hall! Offering approximately 2,040 square feet of living space, an oversized lot and a versatile floor plan, this beautifully maintained home has so much more to offer than meets the eye! Featuring 3 bedrooms, 2 full baths, a powder room and an impressive oversized sunroom/flex space that’s even larger than the primary suite! With its own private exterior entrance and direct kitchen access, this incredible bonus space offers endless possibilities for a home office, guest retreat, hobby room or additional living area. Inside, you’ll find beautiful hardwood flooring, a cozy gas fireplace, crown molding, updated lighting, generous storage and a plumbed bar area ready for your personal touch. Outside, enjoy ample parking, room for your golf cart and the added freedom of NO HOA FEES! Imagine enjoying everything Rock Hall has to offer! Explore nearby marinas, boating, fishing, waterfront restaurants, coffee shops, live music, local shops and the relaxed Eastern Shore lifestyle. Whether you’re searching for a year-round residence or a weekend getaway, this home offers the space and versatility to make it your own. ANOTHER OPTION WORTH EXPLORING! Seller will also consider a short-term SIX-MONTH RENTAL, subject to mutually acceptable terms. NOW OFFERED AT $344,900! Generous living space, a unique bonus room, an oversized lot, NO HOA and flexible options make this a home worth seeing in person. Schedule your private tour today and discover the possibilities!

3 Beds ⋅ 3 Baths

NEW PRICE — $344,900! MORE SPACE, MORE FLEXIBILITY & NO HOA! Discover an exceptional opportunity in the charming waterfront town of Rock Hall! Offering approximately 2,040 square feet of living space, an oversized lot and a versatile floor plan, this beautifully maintained home has so much more to offer than meets the eye! Featuring 3 bedrooms, 2 full baths, a powder room and an impressive oversized sunroom/flex space that’s even larger than the primary suite! With its own private exterior entrance and direct kitchen access, this incredible bonus space offers endless possibilities for a home office, guest retreat, hobby room or additional living area. Inside, you’ll find beautiful hardwood flooring, a cozy gas fireplace, crown molding, updated lighting, generous storage and a plumbed bar area ready for your personal touch. Outside, enjoy ample parking, room for your golf cart and the added freedom of NO HOA FEES! Imagine enjoying everything Rock Hall has to offer! Explore nearby marinas, boating, fishing, waterfront restaurants, coffee shops, live music, local shops and the relaxed Eastern Shore lifestyle. Whether you’re searching for a year-round residence or a weekend getaway, this home offers the space and versatility to make it your own. ANOTHER OPTION WORTH EXPLORING! Seller will also consider a short-term SIX-MONTH RENTAL, subject to mutually acceptable terms. NOW OFFERED AT $344,900! Generous living space, a unique bonus room, an oversized lot, NO HOA and flexible options make this a home worth seeing in person. Schedule your private tour today and discover the possibilities!

21123 Striper Run, Rock Hall

Listing courtesy of Chaney Homes, LLC. Contact:

$379,000

WOW! What a transformation of this sturdy Four Square Colonial nestled in a peaceful small-town setting. Enjoy the convenience of being within walking distance to parks, schools, the post office, and local markets while still having the space and privacy of an oversized nearly half-acre lot. The exterior features a detached oversized two-car garage with pull-through access to the HUGE backyard — perfect for entertaining, gardening, or future outdoor projects. A brand-new roof has just been installed on both the home and garage, adding even more value and peace of mind. Inside, the home has undergone a complete top-to-bottom renovation while maintaining the charm and solid craftsmanship of a bygone era. The stunning new interior includes an open-concept main level, all-new kitchen and baths, updated flooring, fresh drywall, neutral designer paint throughout, and brand-new appliances. Comfort is covered year-round with newly installed central heating and air conditioning. The fabulous primary suite offers a true retreat with a custom glass-enclosed shower and beautifully updated finishes. Additional highlights include a full dry basement offering excellent storage. This home truly offers the best of both worlds — the beauty and convenience of new construction combined with the timeless quality and character of a classic colonial. Put this one at the top of your list to tour soon!

4 Beds ⋅ 3 Baths

WOW! What a transformation of this sturdy Four Square Colonial nestled in a peaceful small-town setting. Enjoy the convenience of being within walking distance to parks, schools, the post office, and local markets while still having the space and privacy of an oversized nearly half-acre lot. The exterior features a detached oversized two-car garage with pull-through access to the HUGE backyard — perfect for entertaining, gardening, or future outdoor projects. A brand-new roof has just been installed on both the home and garage, adding even more value and peace of mind. Inside, the home has undergone a complete top-to-bottom renovation while maintaining the charm and solid craftsmanship of a bygone era. The stunning new interior includes an open-concept main level, all-new kitchen and baths, updated flooring, fresh drywall, neutral designer paint throughout, and brand-new appliances. Comfort is covered year-round with newly installed central heating and air conditioning. The fabulous primary suite offers a true retreat with a custom glass-enclosed shower and beautifully updated finishes. Additional highlights include a full dry basement offering excellent storage. This home truly offers the best of both worlds — the beauty and convenience of new construction combined with the timeless quality and character of a classic colonial. Put this one at the top of your list to tour soon!

122 Main St, Galena

Listing courtesy of Village Real Estate Company LLC. Contact:

$799,900

Built Before America: A Pre-Revolutionary Home in the Heart of Chestertown's Historic District The Bedingfield Hands House, circa 1750, is more than a home—it's a living piece of Chestertown history. Nestled in the heart of the Historic District, this pre-Revolutionary residence has stood witness to generations of change while retaining the charm, craftsmanship, and character that make historic homes so special. History is woven into every corner of the property—from the prominence of past owners down to the foundation, which contains the mast of a ship. The only home downtown with such a generous private front courtyard framed by mature landscaping, vibrant seasonal gardens, brick herringbone paths that create a peaceful retreat just steps from town and the Chester River. Whether enjoying a quiet morning coffee, entertaining guests, or simply admiring the blooms, the outdoor spaces are truly a stand-out feature. Approaching the home, guests are welcomed by a wide red front door, a traditional symbol of hospitality in early America, inviting visitors inside just as it has for centuries. Inside, approximately 2,472 square feet of thoughtfully preserved living space blends historic character with modern comfort. Original wide-plank hardwood floors, period moldings and built-in cabinetry, reflect the home's 18th-century origins, while updated kitchens, baths, and central air/heat provide the conveniences expected today. To the right of the grand foyer, a cozy study lined with built-in bookshelves provides the perfect home office or library and could easily be converted into a first-floor bedroom for those seeking single-level living flexibility. A first floor full bathroom with walk in shower is located conveniently around the corner straight through the foyer. To the left of the foyer and at the forefront of the home, the stunningly preserved parlor, featuring 12x12 wavy glass windows, original panel walls and stunning gas fireplace with pine panel surround, offers an elegant setting for entertaining guests or enjoying quiet evenings at home. Just beyond, the large dining room serves as a memorable gathering space, complete with another fireplace, built-in cabinetry, and a charming pop-out window seat overlooking the side gardens. Just beyond that is a chef's kitchen featuring updated appliances, abundant storage cabinetry, generous island workspace, and a soaring tapered tray ceiling that creates an airy and inviting atmosphere. The kitchen breakfast nook is highlighted by panoramic bay window wall. Off the breakfast nook is a convenient half bath and steps to the side courtyard with pergola and a screened porch. The garage—another rarity in the Historic District—provides valuable storage and convenience. Upstairs, the spacious primary suite blends historic character with thoughtful updates, featuring a practical double closet and an en-suite bath highlighted by distinctive MacKenzie-Childs tile floors and decorative vanity hardware. Two additional generously sized bedrooms and a full bathroom provide comfortable accommodations for guests. Beyond its appeal as a private residence, it is ranked in the top 5% of Chestertown AirBnbs and a guest favorite. Whether you're seeking a full-time residence, weekend retreat, or income-producing investment, this property offers exceptional flexibility. Furniture is negotiable for a truly turnkey opportunity. Step outside and enjoy everything that makes Chestertown so beloved. Stroll to art galleries, Chestertown marina, quaint shops, restaurants, the farmers market, and waterfront park. Enjoy annual traditions such as the Tea Party Festival, Downrigging Weekend, and Dickens of a Christmas, all just moments from your front door. Become the steward of a treasured landmark while enjoying the comfort, beauty, and lifestyle that have made it one of Chestertown's most admired homes for generations.

3 Beds ⋅ 4 Baths

Built Before America: A Pre-Revolutionary Home in the Heart of Chestertown's Historic District The Bedingfield Hands House, circa 1750, is more than a home—it's a living piece of Chestertown history. Nestled in the heart of the Historic District, this pre-Revolutionary residence has stood witness to generations of change while retaining the charm, craftsmanship, and character that make historic homes so special. History is woven into every corner of the property—from the prominence of past owners down to the foundation, which contains the mast of a ship. The only home downtown with such a generous private front courtyard framed by mature landscaping, vibrant seasonal gardens, brick herringbone paths that create a peaceful retreat just steps from town and the Chester River. Whether enjoying a quiet morning coffee, entertaining guests, or simply admiring the blooms, the outdoor spaces are truly a stand-out feature. Approaching the home, guests are welcomed by a wide red front door, a traditional symbol of hospitality in early America, inviting visitors inside just as it has for centuries. Inside, approximately 2,472 square feet of thoughtfully preserved living space blends historic character with modern comfort. Original wide-plank hardwood floors, period moldings and built-in cabinetry, reflect the home's 18th-century origins, while updated kitchens, baths, and central air/heat provide the conveniences expected today. To the right of the grand foyer, a cozy study lined with built-in bookshelves provides the perfect home office or library and could easily be converted into a first-floor bedroom for those seeking single-level living flexibility. A first floor full bathroom with walk in shower is located conveniently around the corner straight through the foyer. To the left of the foyer and at the forefront of the home, the stunningly preserved parlor, featuring 12x12 wavy glass windows, original panel walls and stunning gas fireplace with pine panel surround, offers an elegant setting for entertaining guests or enjoying quiet evenings at home. Just beyond, the large dining room serves as a memorable gathering space, complete with another fireplace, built-in cabinetry, and a charming pop-out window seat overlooking the side gardens. Just beyond that is a chef's kitchen featuring updated appliances, abundant storage cabinetry, generous island workspace, and a soaring tapered tray ceiling that creates an airy and inviting atmosphere. The kitchen breakfast nook is highlighted by panoramic bay window wall. Off the breakfast nook is a convenient half bath and steps to the side courtyard with pergola and a screened porch. The garage—another rarity in the Historic District—provides valuable storage and convenience. Upstairs, the spacious primary suite blends historic character with thoughtful updates, featuring a practical double closet and an en-suite bath highlighted by distinctive MacKenzie-Childs tile floors and decorative vanity hardware. Two additional generously sized bedrooms and a full bathroom provide comfortable accommodations for guests. Beyond its appeal as a private residence, it is ranked in the top 5% of Chestertown AirBnbs and a guest favorite. Whether you're seeking a full-time residence, weekend retreat, or income-producing investment, this property offers exceptional flexibility. Furniture is negotiable for a truly turnkey opportunity. Step outside and enjoy everything that makes Chestertown so beloved. Stroll to art galleries, Chestertown marina, quaint shops, restaurants, the farmers market, and waterfront park. Enjoy annual traditions such as the Tea Party Festival, Downrigging Weekend, and Dickens of a Christmas, all just moments from your front door. Become the steward of a treasured landmark while enjoying the comfort, beauty, and lifestyle that have made it one of Chestertown's most admired homes for generations.

106 Queen St S, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$350,000

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006168 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

1 Beds ⋅ 1 Baths

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006168 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

117 Water St N Unit 2B, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact:

$375,000

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

2 Beds ⋅ 1 Baths

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

117 Water St N Unit 2A, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact:

$200,000

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006164 ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

1 Beds ⋅ 1 Baths

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006164 ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

117 Water St N Unit 1B, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact:

$685,000

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006168 ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

3 Beds ⋅ 3 Baths

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006168 ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

117 Water St N Unit 1A, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact:

117 Water St N Unit 1A, 1B, 2A, & 2B, Chestertown

$1,500,000

**Listing price is for FOUR units for sale as an investment package! 117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! 1A – three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! 1B – the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. 2A – a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. 2B - a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible.

7 Beds ⋅ 5 Baths

**Listing price is for FOUR units for sale as an investment package! 117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! 1A – three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! 1B – the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. 2A – a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. 2B - a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible.

117 Water St N Unit 1A, 1B, 2A, & 2B, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact:

$765,900

**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.

3 Beds ⋅ 3 Baths

**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.

#37 Landing, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

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