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Brand new home in Historic Chestertown available for move-in Right 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 $6,300 or more in closing help from the builders' preferred lender!

3 Beds ⋅ 2 Baths

Brand new home in Historic Chestertown available for move-in Right 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 $6,300 or more in closing help from the builders' preferred lender!

109 Metcalf Rd, Chestertown

Listing courtesy of Real Broker, LLC. Contact:

Selling Office: Real Broker, LLC.

$264,900

Brand new home in Historic Chestertown available for move-in this Right 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.

3 Beds ⋅ 2 Baths

Brand new home in Historic Chestertown available for move-in this Right 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.

101 Metcalf Rd, Chestertown

Listing courtesy of Real Broker, LLC. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

$259,900

Brand new home in Historic Chestertown available for move-in this Right 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. Up to $7,500 in closing help available on select models when using builders partner lender and title company.

3 Beds ⋅ 2 Baths

Brand new home in Historic Chestertown available for move-in this Right 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. Up to $7,500 in closing help available on select models when using builders partner lender and title company.

107 Metcalf Rd, Chestertown

Listing courtesy of Real Broker, LLC. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$250,000

This affordable home is ready for you to call HOME! Spacious end-unit Townhome offers a 1,280-sq-ft floor plan with durable LVP flooring throughout the first floor. Enjoy a bright, open-concept living area where the living room flows into the kitchen, featuring a large island, stainless steel appliances, granite countertops, and white shaker cabinets. Step outside to a covered patio overlooking the side and backyard, complete with a new shed—perfect for relaxing or entertaining. The second floor is carpeted and includes a generously sized primary bedroom. and two additional bedrooms. A full bathroom on the second floor offers convenient access from the primary bedroom. Ideally located near Washington College, this home places you moments from Historic Chestertown and the Chester River. Indulge in exceptional dining, charming cafés, shopping, art galleries, the Memorial Weekend Tea Party and more.

3 Beds ⋅ 2 Baths

This affordable home is ready for you to call HOME! Spacious end-unit Townhome offers a 1,280-sq-ft floor plan with durable LVP flooring throughout the first floor. Enjoy a bright, open-concept living area where the living room flows into the kitchen, featuring a large island, stainless steel appliances, granite countertops, and white shaker cabinets. Step outside to a covered patio overlooking the side and backyard, complete with a new shed—perfect for relaxing or entertaining. The second floor is carpeted and includes a generously sized primary bedroom. and two additional bedrooms. A full bathroom on the second floor offers convenient access from the primary bedroom. Ideally located near Washington College, this home places you moments from Historic Chestertown and the Chester River. Indulge in exceptional dining, charming cafés, shopping, art galleries, the Memorial Weekend Tea Party and more.

112 Metcalf Rd, Chestertown

Listing courtesy of Rosendale Realty. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

$245,000

Welcome to easy, move in ready living in the heart of Chestertown! This fully renovated townhouse offers modern updates, low maintenance living, and an unbeatable location just minutes from local shops, restaurants, grocery stores, the YMCA, and everything Chestertown has to offer. Step inside to find a beautifully updated interior featuring fresh paint throughout and durable oak luxury vinyl plank flooring that creates a warm and inviting feel. The living area opens up to the dining area and flows into the completely remodeled kitchen that showcases crisp white soft close cabinetry, elegant quartz countertops, and stainless steel appliances; perfect for everyday living and entertaining. The home also features a renovated full bathroom, in-unit washer and dryer, and a convenient one story layout designed for comfort and accessibility. Enjoy your morning coffee or unwind at the end of the day on the covered back porch. Additional peace of mind comes with a brand new roof installed in May 2026. Whether you’re a first time homebuyer searching for a stylish, affordable, move in ready home, looking to downsize into a low maintenance property, or an investor seeking a rental opportunity in a desirable location, this home offers incredible potential. Don’t miss the chance to own a beautifully renovated home in one of Kent County’s most charming communities! Disclosure: Listing agent has an ownership interest in the entity that owns the subject property.

3 Beds ⋅ 1 Baths

Welcome to easy, move in ready living in the heart of Chestertown! This fully renovated townhouse offers modern updates, low maintenance living, and an unbeatable location just minutes from local shops, restaurants, grocery stores, the YMCA, and everything Chestertown has to offer. Step inside to find a beautifully updated interior featuring fresh paint throughout and durable oak luxury vinyl plank flooring that creates a warm and inviting feel. The living area opens up to the dining area and flows into the completely remodeled kitchen that showcases crisp white soft close cabinetry, elegant quartz countertops, and stainless steel appliances; perfect for everyday living and entertaining. The home also features a renovated full bathroom, in-unit washer and dryer, and a convenient one story layout designed for comfort and accessibility. Enjoy your morning coffee or unwind at the end of the day on the covered back porch. Additional peace of mind comes with a brand new roof installed in May 2026. Whether you’re a first time homebuyer searching for a stylish, affordable, move in ready home, looking to downsize into a low maintenance property, or an investor seeking a rental opportunity in a desirable location, this home offers incredible potential. Don’t miss the chance to own a beautifully renovated home in one of Kent County’s most charming communities! Disclosure: Listing agent has an ownership interest in the entity that owns the subject property.

107 Conley Dr, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Cummings & Co. Realtors.

$240,000

🏡 💎 Like-New Chestertown Ranch: Pristine Condition, Ready Today! $250K 🎉 Skip the construction drama! Step into this stunning, move-in-ready 3-bedroom, 2-bath ranch at 100 Metcalf Rd, Chestertown, MD 21620 for just $250,000! ✨ Your Dream Home Checklist: ✅ * NO HOA! Freedom & Savings! 💸 * One-Level Living: Easy breezy! 🚶‍♀️ * Open Concept: Perfect for entertaining! 🛋️ The heart of the home is the spectacular eat-in kitchen! You'll love the white shaker cabinets, dazzling granite countertops, and sleek stainless steel appliances. 🍳 The main areas feature gorgeous LVP flooring, while cozy carpet warms the bedrooms. Step outside to your private covered patio for morning coffee ☕ or evening relaxation. 🌞 With a generous 5,914 sq ft lot, there's plenty of room for fun! 🌳 Retreat to your private primary suite 👑 with a spa-like en-suite and walk-in shower. 🚿 Embrace the Chestertown Life! ⚓ This prime spot is minutes from historic downtown charm! Enjoy the weekly farmers market 🥕, shops, galleries 🖼️, and waterfront festivals like the famous Downrigging Weekend ⛵. This golden opportunity won't last long! Be the first to call this exquisite property "home." 🔑 Your new beginning starts here! ❤️

3 Beds ⋅ 2 Baths

🏡 💎 Like-New Chestertown Ranch: Pristine Condition, Ready Today! $250K 🎉 Skip the construction drama! Step into this stunning, move-in-ready 3-bedroom, 2-bath ranch at 100 Metcalf Rd, Chestertown, MD 21620 for just $250,000! ✨ Your Dream Home Checklist: ✅ * NO HOA! Freedom & Savings! 💸 * One-Level Living: Easy breezy! 🚶‍♀️ * Open Concept: Perfect for entertaining! 🛋️ The heart of the home is the spectacular eat-in kitchen! You'll love the white shaker cabinets, dazzling granite countertops, and sleek stainless steel appliances. 🍳 The main areas feature gorgeous LVP flooring, while cozy carpet warms the bedrooms. Step outside to your private covered patio for morning coffee ☕ or evening relaxation. 🌞 With a generous 5,914 sq ft lot, there's plenty of room for fun! 🌳 Retreat to your private primary suite 👑 with a spa-like en-suite and walk-in shower. 🚿 Embrace the Chestertown Life! ⚓ This prime spot is minutes from historic downtown charm! Enjoy the weekly farmers market 🥕, shops, galleries 🖼️, and waterfront festivals like the famous Downrigging Weekend ⛵. This golden opportunity won't last long! Be the first to call this exquisite property "home." 🔑 Your new beginning starts here! ❤️

100 Metcalf Rd, Chestertown

Listing courtesy of Bayside Realty. Contact:

Selling Office: Douglas Realty LLC.

$230,000

Amazing deal on this 2 yr old duplex/rancher with no stairs that shows like new. Awesome location on the outskirts of Chestertown but within walking distance to shopping, doctors, restaurants, pharmacies, YMCA and more. Spacious open floor plan with 3BR, 2BA, living room - dinning room - kitchen combination. Enjoy the granite counters or LVP flooring through out. Back patio with storage outside the primary bedroom. This property is at the end of Metcalf Rd.

3 Beds ⋅ 2 Baths

Amazing deal on this 2 yr old duplex/rancher with no stairs that shows like new. Awesome location on the outskirts of Chestertown but within walking distance to shopping, doctors, restaurants, pharmacies, YMCA and more. Spacious open floor plan with 3BR, 2BA, living room - dinning room - kitchen combination. Enjoy the granite counters or LVP flooring through out. Back patio with storage outside the primary bedroom. This property is at the end of Metcalf Rd.

126 Metcalf Rd, Chestertown

Listing courtesy of Taylor Properties. Contact:

Selling Office: Benson & Mangold, LLC..

$150,000

Purchase of opportunity thru rehab financing for completion of a new kitchen, painting and flooring . Call for details and will assist you with your dream of owning your own home.

3 Beds ⋅ 1 Baths

Purchase of opportunity thru rehab financing for completion of a new kitchen, painting and flooring . Call for details and will assist you with your dream of owning your own home.

107 Conley Dr, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Benson & Mangold, LLC.