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$375,000

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:

$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: 3024222619

$550,000

103 Sutton is perfectly situated just a stone’s throw from the vibrant heart of Downtown Chestertown. This exquisite 4+ bedroom residence is designed to cater to the diverse needs of today’s Buyers, offering a harmonious blend of comfort, style, and functionality. This home is ideal for those upsizing or seeking multi-generational living. * Originally built as the community model home – and meticulously maintained since – it has ALL the extras: generous breakfast nook bump out, gas fireplace, gleaming hardwood floors, upgraded carpet, oversized windows, granite countertops, stainless appliances, dedicated home office, and a finished basement with a full bath and expansive wet bar. * As you step inside, you’ll be greeted by a two-story foyer flooded with light, dining room and den or family room. The gourmet kitchen that is a chef’s paradise, featuring high-end appliances, custom hardwood cabinetry, and a small island for an ideal triangle of space for meal prep. The open concept layout flows effortlessly into the breakfast nook and living room, providing the perfect setting for family gatherings and celebrations with friends. Click on the propane fireplace for a cozy night watching the sunset or snow flurries outside the tall windows. * The spacious primary suite is an escape through a double door entry – featuring a lighted tray ceiling, a large walk-in closet, en suite bath with soaking tub, glass shower, and a separate water closet. Three additional bedrooms all have custom trim work, generous closets, and large windows. * The finished basement is a standout feature, complete with a stylish wet bar with stone walls that transforms it into the ultimate entertainment zone, perfect for hosting game nights or movie marathons. The backyard feels private with mature trees and a gentle slope, ideal for play space. * The proximity to local parks, playgrounds, restaurants, and shopping ensures that all your family’s needs are met within minutes. Additionally, the Coventry Farms neighborhood fosters a sense of community all while being a convenient distance from Middletown, DE, Philadelphia, PA, Washington DC, Baltimore, MD, and points beyond. * This home is not just a place to live; it’s a lifestyle waiting to be embraced. Don’t miss the opportunity to make this stunning property your own. Schedule your private tour today and experience firsthand what this exceptional home has to offer.

5 Beds ⋅ 4 Baths

103 Sutton is perfectly situated just a stone’s throw from the vibrant heart of Downtown Chestertown. This exquisite 4+ bedroom residence is designed to cater to the diverse needs of today’s Buyers, offering a harmonious blend of comfort, style, and functionality. This home is ideal for those upsizing or seeking multi-generational living. * Originally built as the community model home – and meticulously maintained since – it has ALL the extras: generous breakfast nook bump out, gas fireplace, gleaming hardwood floors, upgraded carpet, oversized windows, granite countertops, stainless appliances, dedicated home office, and a finished basement with a full bath and expansive wet bar. * As you step inside, you’ll be greeted by a two-story foyer flooded with light, dining room and den or family room. The gourmet kitchen that is a chef’s paradise, featuring high-end appliances, custom hardwood cabinetry, and a small island for an ideal triangle of space for meal prep. The open concept layout flows effortlessly into the breakfast nook and living room, providing the perfect setting for family gatherings and celebrations with friends. Click on the propane fireplace for a cozy night watching the sunset or snow flurries outside the tall windows. * The spacious primary suite is an escape through a double door entry – featuring a lighted tray ceiling, a large walk-in closet, en suite bath with soaking tub, glass shower, and a separate water closet. Three additional bedrooms all have custom trim work, generous closets, and large windows. * The finished basement is a standout feature, complete with a stylish wet bar with stone walls that transforms it into the ultimate entertainment zone, perfect for hosting game nights or movie marathons. The backyard feels private with mature trees and a gentle slope, ideal for play space. * The proximity to local parks, playgrounds, restaurants, and shopping ensures that all your family’s needs are met within minutes. Additionally, the Coventry Farms neighborhood fosters a sense of community all while being a convenient distance from Middletown, DE, Philadelphia, PA, Washington DC, Baltimore, MD, and points beyond. * This home is not just a place to live; it’s a lifestyle waiting to be embraced. Don’t miss the opportunity to make this stunning property your own. Schedule your private tour today and experience firsthand what this exceptional home has to offer.

103 Sutton Way, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344