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Nestled in the heart of the Chestertown Historic District, this exquisite residence offers a harmonious blend of traditional charm and modern luxury. Built in 2008, this detached home stands as a testament to meticulous craftsmanship and thoughtful design, ensuring an exceptional living experience. Step inside to discover an open floor plan that invites natural light to dance across the spacious interiors. The heart of the home features a cozy gas fireplace, perfect for creating warm, inviting gatherings. The well-appointed kitchen is a culinary enthusiast's dream, equipped with high-end appliances including a built-in range, microwave, and dishwasher, all seamlessly integrated for both functionality and style. The stacked washer and dryer add convenience, making laundry days a breeze. With two generously sized bedrooms and two and a half elegantly designed bathrooms, this home provides ample space for relaxation and rejuvenation. Each bathroom boasts modern fixtures and finishes, ensuring a spa-like experience at home. The attic space while unfinished, has the ability to be finished for additional living space, if desired. The exterior of the property is equally captivating, featuring beautifully maintained sidewalks and exterior lighting that enhances the home's curb appeal. Enjoy serene evenings on the private patio, where you can unwind and soak in the tranquil surroundings. The lot, spanning 1,330 square feet, offers a manageable outdoor space that complements the busy lifestyle of today's homeowner. Located in a vibrant community, this residence is not just a home; it's a lifestyle. The Chestertown Historic District is renowned for its rich history and picturesque streets, providing a unique backdrop for your daily life. Enjoy leisurely strolls through charming neighborhoods, explore local boutiques, or indulge in the culinary delights of nearby restaurants. This property is more than just a dwelling; it's an opportunity to embrace a luxurious lifestyle in a historic setting. With its impeccable condition and high-end features, this home is ready to welcome you into a world of comfort and elegance. Don't miss your chance to own a piece of this exclusive community-schedule your private tour today and experience the allure of this remarkable residence for yourself.

2 Beds ⋅ 3 Baths

Nestled in the heart of the Chestertown Historic District, this exquisite residence offers a harmonious blend of traditional charm and modern luxury. Built in 2008, this detached home stands as a testament to meticulous craftsmanship and thoughtful design, ensuring an exceptional living experience. Step inside to discover an open floor plan that invites natural light to dance across the spacious interiors. The heart of the home features a cozy gas fireplace, perfect for creating warm, inviting gatherings. The well-appointed kitchen is a culinary enthusiast's dream, equipped with high-end appliances including a built-in range, microwave, and dishwasher, all seamlessly integrated for both functionality and style. The stacked washer and dryer add convenience, making laundry days a breeze. With two generously sized bedrooms and two and a half elegantly designed bathrooms, this home provides ample space for relaxation and rejuvenation. Each bathroom boasts modern fixtures and finishes, ensuring a spa-like experience at home. The attic space while unfinished, has the ability to be finished for additional living space, if desired. The exterior of the property is equally captivating, featuring beautifully maintained sidewalks and exterior lighting that enhances the home's curb appeal. Enjoy serene evenings on the private patio, where you can unwind and soak in the tranquil surroundings. The lot, spanning 1,330 square feet, offers a manageable outdoor space that complements the busy lifestyle of today's homeowner. Located in a vibrant community, this residence is not just a home; it's a lifestyle. The Chestertown Historic District is renowned for its rich history and picturesque streets, providing a unique backdrop for your daily life. Enjoy leisurely strolls through charming neighborhoods, explore local boutiques, or indulge in the culinary delights of nearby restaurants. This property is more than just a dwelling; it's an opportunity to embrace a luxurious lifestyle in a historic setting. With its impeccable condition and high-end features, this home is ready to welcome you into a world of comfort and elegance. Don't miss your chance to own a piece of this exclusive community-schedule your private tour today and experience the allure of this remarkable residence for yourself.

111 Kent St S, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. 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:

$2,895,000

Discover 6324 Quaker Neck Road, an exceptional waterfront estate spanning over 5 acres along the East Fork of Langford Creek offering over 5 feet of water at low tide. Over 5,900 square feet of refined living space with 5 bedrooms and 4 baths, designed for elegant Shore entertaining and everyday ease. A new private pier with swim platform and boat lift, plus your private beach, extends living outdoors — complemented by a detached garage with carriage house and a pole building. Minutes to Chestertown, yet quietly removed — a distinguished Quaker Neck offering for the buyer who wants it all.

5 Beds ⋅ 4 Baths

Discover 6324 Quaker Neck Road, an exceptional waterfront estate spanning over 5 acres along the East Fork of Langford Creek offering over 5 feet of water at low tide. Over 5,900 square feet of refined living space with 5 bedrooms and 4 baths, designed for elegant Shore entertaining and everyday ease. A new private pier with swim platform and boat lift, plus your private beach, extends living outdoors — complemented by a detached garage with carriage house and a pole building. Minutes to Chestertown, yet quietly removed — a distinguished Quaker Neck offering for the buyer who wants it all.

6324 Quaker Neck Rd, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

$239,900

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

3 Beds ⋅ 2 Baths

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

104 Conley Dr, Chestertown

Listing courtesy of Cummings & Co. Realtors. Contact:

$275,000

Enjoy the convenience of townhome living in Oak Hollow, just minutes from historic downtown Chestertown, local schools, and the YMCA. With approximately 1,900 square feet of living space across three levels, this home offers a flexible layout with room to make it your own. The ground level features a versatile bonus room that could serve as a home office, workout space, or recreation room, along with an attached one-car garage. Upstairs, the main living level offers a spacious living room and an eat-in kitchen with access to a private rear deck overlooking a wooded backdrop—an inviting spot to relax or enjoy your morning coffee. The upper level includes three bedrooms, including a primary suite with a private bath, plus a convenient dedicated laundry area. The Seller is offering a $2,500 credit toward painting, cosmetic updates, or carpet, giving the next owner an opportunity to personalize the space to suit their style. Conveniently located and offering a practical, three-level layout, this Oak Hollow townhome is worth a look for buyers seeking their first home, those looking to downsize, or investors exploring rental opportunities.

3 Beds ⋅ 3 Baths

Enjoy the convenience of townhome living in Oak Hollow, just minutes from historic downtown Chestertown, local schools, and the YMCA. With approximately 1,900 square feet of living space across three levels, this home offers a flexible layout with room to make it your own. The ground level features a versatile bonus room that could serve as a home office, workout space, or recreation room, along with an attached one-car garage. Upstairs, the main living level offers a spacious living room and an eat-in kitchen with access to a private rear deck overlooking a wooded backdrop—an inviting spot to relax or enjoy your morning coffee. The upper level includes three bedrooms, including a primary suite with a private bath, plus a convenient dedicated laundry area. The Seller is offering a $2,500 credit toward painting, cosmetic updates, or carpet, giving the next owner an opportunity to personalize the space to suit their style. Conveniently located and offering a practical, three-level layout, this Oak Hollow townhome is worth a look for buyers seeking their first home, those looking to downsize, or investors exploring rental opportunities.

104 Acorn Dr, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

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