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New Contructions - Ready for move in , in September 2023 This home features Luxury Vinyl Flooring throughout, White Shaker Cabinets, Granite Counters, Spacious Living Room, Eat in Kitchen area, covered patio off the kitchen, spacious bedrooms including a large primary bedroom suite and much more! These homes are selling faster than they can be built, so come by today and take advantage of this opportunity while it lasts. Special financing programs available, including Zero Down payment loans and closing costs assistance programs so you can own this home for less than renting. Home is delivered at the asking price the way you see it in the photos.

116 Metcalf Rd, Chestertown

Listing courtesy of RE/MAX Executive. Contact:

$385,945

Currently being built in The Village at Chestertown! The Verona, a 2,302 square foot, three-story home, offers five bedrooms, and three and a half bathrooms and is positioned on a corner homesite. This well-designed home has an inviting foyer that opens to the spacious family room. The family room is open to the dining space and the family-friendly kitchen with stainless steel appliances, classic birch cabinets, a large corner pantry and a peninsula island with additional room for seating. A powder room is conveniently located on the first floor tucked away in a private nook. This roomy floor plan allows the entire family to live comfortably with the ideal amount of space and room for flexibility. The upstairs owner's bedroom with an en suite bathroom and a walk-in closet sits in the back of the home for privacy. There are three additional bedrooms and a secondary bathroom on the second floor. The third floor offers a fifth bedroom and a third full bathroom, as well as a flex room that could be used for storage. The Verona includes a washer and dryer, luxury vinyl plank flooring, a white window treatment package, and the exclusive Smart Home® Package giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

5 Beds ⋅ 4 Baths

Currently being built in The Village at Chestertown! The Verona, a 2,302 square foot, three-story home, offers five bedrooms, and three and a half bathrooms and is positioned on a corner homesite. This well-designed home has an inviting foyer that opens to the spacious family room. The family room is open to the dining space and the family-friendly kitchen with stainless steel appliances, classic birch cabinets, a large corner pantry and a peninsula island with additional room for seating. A powder room is conveniently located on the first floor tucked away in a private nook. This roomy floor plan allows the entire family to live comfortably with the ideal amount of space and room for flexibility. The upstairs owner's bedroom with an en suite bathroom and a walk-in closet sits in the back of the home for privacy. There are three additional bedrooms and a secondary bathroom on the second floor. The third floor offers a fifth bedroom and a third full bathroom, as well as a flex room that could be used for storage. The Verona includes a washer and dryer, luxury vinyl plank flooring, a white window treatment package, and the exclusive Smart Home® Package giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

107 Flying Cloud Dr, Chestertown

Listing courtesy of DRH Realty Capital, LLC.. Contact: (667) 500-2488

$385,945

New home, under construction in The Village at Chestertown! The Verona, a 2,302 square foot, three-story home, offers five bedrooms, and three and a half bathrooms. This well-designed home has an inviting foyer that opens to the spacious family room. The family room is open to the dining space and the family-friendly kitchen with stainless steel appliances, beautiful white cabinets, luxury vinyl plank flooring, a large corner pantry and a peninsula island with additional room for seating. A powder room is conveniently located on the first floor tucked away in a private nook. This roomy floor plan allows the entire family to live comfortably with the ideal amount of space and room for flexibility. The upstairs owner's bedroom with an en suite bathroom and a walk-in closet sits in the back of the home for privacy. There are three additional bedrooms and a secondary bathroom on the second floor. The third floor offers a fifth bedroom and a third full bathroom, as well as a flex room that could be used for storage. The Verona includes a washer and dryer, a white window treatment package, and the exclusive Smart Home® Package giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

5 Beds ⋅ 4 Baths

New home, under construction in The Village at Chestertown! The Verona, a 2,302 square foot, three-story home, offers five bedrooms, and three and a half bathrooms. This well-designed home has an inviting foyer that opens to the spacious family room. The family room is open to the dining space and the family-friendly kitchen with stainless steel appliances, beautiful white cabinets, luxury vinyl plank flooring, a large corner pantry and a peninsula island with additional room for seating. A powder room is conveniently located on the first floor tucked away in a private nook. This roomy floor plan allows the entire family to live comfortably with the ideal amount of space and room for flexibility. The upstairs owner's bedroom with an en suite bathroom and a walk-in closet sits in the back of the home for privacy. There are three additional bedrooms and a secondary bathroom on the second floor. The third floor offers a fifth bedroom and a third full bathroom, as well as a flex room that could be used for storage. The Verona includes a washer and dryer, a white window treatment package, and the exclusive Smart Home® Package giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

111 Flying Cloud Dr, Chestertown

Listing courtesy of DRH Realty Capital, LLC.. Contact: (667) 500-2488

$234,900

Come by this lovely BRAND NEW home in Historic Chestertown, available in for move in in September. This home features Luxury Vinyl Flooring throughout, White Shaker Cabinets, Granite Counters, Spacious Living Room, Eat in Kitchen area, covered patio off the kitchen, spacious bedrooms including a large primary bedroom suite and much more! These homes are selling faster than they can be built, so come by today and take advantage of this opportunity while it lasts. Special financing programs available, including Zero Down payment loans and closing costs assistance programs so you can own this home for less than renting. Home is delivered at the asking price the way you see it in the photos.

Come by this lovely BRAND NEW home in Historic Chestertown, available in for move in in September. This home features Luxury Vinyl Flooring throughout, White Shaker Cabinets, Granite Counters, Spacious Living Room, Eat in Kitchen area, covered patio off the kitchen, spacious bedrooms including a large primary bedroom suite and much more! These homes are selling faster than they can be built, so come by today and take advantage of this opportunity while it lasts. Special financing programs available, including Zero Down payment loans and closing costs assistance programs so you can own this home for less than renting. Home is delivered at the asking price the way you see it in the photos.

112 Metcalf Rd, Chestertown

Listing courtesy of RE/MAX Executive. Contact:

$250,000

Will consider offers. Lovely Renovated Farm/Folk style home with Public water and sewer home in the village of Fairlee, just 10 minutes to downtown Chestertown. New electric, plumbing, and drywall. The washer/dryer and hot water tank can be moved upstairs. The owner started to renovate to make 2 apartments, and the floor plan can be readjusted for a larger single-family home. Move-in ready. Large grassy yard. Quiet neighborhood. A quick settlement is fine.

23073 Parsons Rd, Chestertown

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

$850,000

Waterfront and low maintenance located less than 1 mile from Historic Chestertown! The home is thoughtfully designed with an attached garage and first floor ensuite to allow for main level living (present or future). The abundance of natural light that fills the interior highlights the architectural detail throughout and is further balanced by the neutral paint scheme and hardwood flooring. **Open floor plan, soft close cabinetry, 2 propane fireplaces, expansive unobstructed water views of the Chester, and more...

2 Beds ⋅ 3 Baths

Waterfront and low maintenance located less than 1 mile from Historic Chestertown! The home is thoughtfully designed with an attached garage and first floor ensuite to allow for main level living (present or future). The abundance of natural light that fills the interior highlights the architectural detail throughout and is further balanced by the neutral paint scheme and hardwood flooring. **Open floor plan, soft close cabinetry, 2 propane fireplaces, expansive unobstructed water views of the Chester, and more...

318 Landing Ln Unit #30, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453

$440,000

Welcome to this charming colonial home nestled on a sprawling corner lot where timeless elegance meets modern comforts. With 4 bedrooms and 2.5 baths, this residence offers ample space for both relaxation and entertainment. As you approach the property, you'll be captivated by its picturesque curb appeal. The classic colonial architecture sets the stage for the delightful surprises awaiting within. Step through the front door and into a world of warmth and sophistication. The main level greets you with dual living rooms guiding you effortlessly throughout the downstairs living space. Newly installed vinyl plank flooring stretches out before you, enhancing the home's inviting atmosphere. The heart of this home is the meticulously designed galley kitchen, featuring gorgeous custom cabinetry, gleaming countertops, and modern appliances. Whether you're a culinary enthusiast or simply enjoy gathering with loved ones, this space will surely inspire memorable moments. The adjacent dining area offers a haven for shared meals, with natural light streaming through the windows, casting a soft glow on the room. It's the perfect spot to savor your morning coffee or host a lively dinner party. When it's time to unwind, make your way to the cozy living room. Bathed in natural light and adorned with a charming fireplace, this space invites relaxation and intimate conversations with friends and family. Retreat to the upper level, where you'll find the luxurious primary suite. The spacious bedroom with walk-in closet creates a haven for restful nights. The en-suite bathroom offers a tranquil escape, complete with modern fixtures, a soaking tub, and a separate shower. Three additional well-appointed bedrooms provide ample space for family, guests, or creative pursuits. Each room exudes a welcoming ambiance, with ample closet space and large windows that bathe the rooms in natural light. The exterior of the home is equally enchanting, with the large corner lot providing endless possibilities for outdoor enjoyment. Whether you envision creating a vibrant garden oasis or hosting lively barbecues, this expansive space will inspire your imagination. Recent upgrades have been thoughtfully implemented, including a roof with a transferrable 50-year warranty, a new garage door, and a hot water heater - all just three years old. Additionally, the 2-zone heating and cooling system ensure year-round comfort and energy efficiency. Located in a desirable neighborhood of Crestview, this home offers convenience and tranquility in equal measure. Explore nearby parks, schools, and shopping destinations, all within easy reach. In summary, this colonial gem combines classic allure with modern amenities, creating a haven you'll be proud to call home. Don't miss your chance to experience the beauty and comfort this property has to offer.

Welcome to this charming colonial home nestled on a sprawling corner lot where timeless elegance meets modern comforts. With 4 bedrooms and 2.5 baths, this residence offers ample space for both relaxation and entertainment. As you approach the property, you'll be captivated by its picturesque curb appeal. The classic colonial architecture sets the stage for the delightful surprises awaiting within. Step through the front door and into a world of warmth and sophistication. The main level greets you with dual living rooms guiding you effortlessly throughout the downstairs living space. Newly installed vinyl plank flooring stretches out before you, enhancing the home's inviting atmosphere. The heart of this home is the meticulously designed galley kitchen, featuring gorgeous custom cabinetry, gleaming countertops, and modern appliances. Whether you're a culinary enthusiast or simply enjoy gathering with loved ones, this space will surely inspire memorable moments. The adjacent dining area offers a haven for shared meals, with natural light streaming through the windows, casting a soft glow on the room. It's the perfect spot to savor your morning coffee or host a lively dinner party. When it's time to unwind, make your way to the cozy living room. Bathed in natural light and adorned with a charming fireplace, this space invites relaxation and intimate conversations with friends and family. Retreat to the upper level, where you'll find the luxurious primary suite. The spacious bedroom with walk-in closet creates a haven for restful nights. The en-suite bathroom offers a tranquil escape, complete with modern fixtures, a soaking tub, and a separate shower. Three additional well-appointed bedrooms provide ample space for family, guests, or creative pursuits. Each room exudes a welcoming ambiance, with ample closet space and large windows that bathe the rooms in natural light. The exterior of the home is equally enchanting, with the large corner lot providing endless possibilities for outdoor enjoyment. Whether you envision creating a vibrant garden oasis or hosting lively barbecues, this expansive space will inspire your imagination. Recent upgrades have been thoughtfully implemented, including a roof with a transferrable 50-year warranty, a new garage door, and a hot water heater - all just three years old. Additionally, the 2-zone heating and cooling system ensure year-round comfort and energy efficiency. Located in a desirable neighborhood of Crestview, this home offers convenience and tranquility in equal measure. Explore nearby parks, schools, and shopping destinations, all within easy reach. In summary, this colonial gem combines classic allure with modern amenities, creating a haven you'll be proud to call home. Don't miss your chance to experience the beauty and comfort this property has to offer.

106 Northgate Dr, Chestertown

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

$625,000

Quaint, historic home in Great Oak Landing with tons of character. Double front doors and double parlors. Randon width 18th-century floors. Sunroom and screened-in porch. 2 gas fireplaces. Fenced-in yard, gorgeous gardens with pond, deck, and brick patio. 2 bedrooms and 2 full baths on the main level. Additional 2 bedrooms and full bath on the second floor. Also on the second floor is a vast storage or bonus room. A leisurely stroll to Great Oak Marina and a golf course. $350/year road maintenance fee. Voluntary community civic association and Great Oak Marina have offered privileges to paid community members ($100 annual dues), including 9 hole golf course, boat ramp, pool, and beaches. Boat slips are available to rent.

Quaint, historic home in Great Oak Landing with tons of character. Double front doors and double parlors. Randon width 18th-century floors. Sunroom and screened-in porch. 2 gas fireplaces. Fenced-in yard, gorgeous gardens with pond, deck, and brick patio. 2 bedrooms and 2 full baths on the main level. Additional 2 bedrooms and full bath on the second floor. Also on the second floor is a vast storage or bonus room. A leisurely stroll to Great Oak Marina and a golf course. $350/year road maintenance fee. Voluntary community civic association and Great Oak Marina have offered privileges to paid community members ($100 annual dues), including 9 hole golf course, boat ramp, pool, and beaches. Boat slips are available to rent.

10230 John Carvill Rd, Chestertown

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

$1,499,000

Introducing a stunning new construction waterfront home in Chestertown's prestigious waterfront community, Chester River Landing. Hands down, one of the best lots in the community! This exquisite three-bedroom, three-and-a-half-bath home offers luxurious living and breathtaking, panoramic views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious layout provides ample room for relaxation and entertaining. With high-end finishes and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Introducing a stunning new construction waterfront home in Chestertown's prestigious waterfront community, Chester River Landing. Hands down, one of the best lots in the community! This exquisite three-bedroom, three-and-a-half-bath home offers luxurious living and breathtaking, panoramic views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious layout provides ample room for relaxation and entertaining. With high-end finishes and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Little Harbor Way Unit #1, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665

$949,900

Introducing a stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. This exquisite four-bedroom, two-and-a-half-bath home offers luxurious living and breathtaking views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious layout provides ample room for relaxation and entertaining. With high-end finishes and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

4 Beds ⋅ 4 Baths

Introducing a stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. This exquisite four-bedroom, two-and-a-half-bath home offers luxurious living and breathtaking views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious layout provides ample room for relaxation and entertaining. With high-end finishes and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Landing Ln Unit #25, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665

$224,900

Looking for an investment property that you can put your own personal touch on in the heart of Chestertown? This charming home needs some repairs but has the potential to be a real gem. This ‘in-town’ home offers hardwood floors in many rooms. The main level features an eat in kitchen with separate dining room, living room, half bath and enclosed front porch / sitting area. Upstairs, offers 3 bedrooms and a full bath. Secluded/Private backyard with Patio area and a detached garage w/workshop. Rear Yard area in back of Garage would make a great area for a Fire Pit or Gazebo? Located in the cozy Historic District and within walking distance to downtown shops, restaurants, marinas, and Washington College. Short walk to the Chester River ! Would make a solid rental. this property boasts a spacious layout with plenty of room for customization. Whether you're looking to flip or rent out, this property is a great opportunity to invest in your future. Don't miss out on this chance to turn this fixer-upper into your dream investment property in the heart of Chestertown. OFF STREET Parking Cash or conventional financing.

Looking for an investment property that you can put your own personal touch on in the heart of Chestertown? This charming home needs some repairs but has the potential to be a real gem. This ‘in-town’ home offers hardwood floors in many rooms. The main level features an eat in kitchen with separate dining room, living room, half bath and enclosed front porch / sitting area. Upstairs, offers 3 bedrooms and a full bath. Secluded/Private backyard with Patio area and a detached garage w/workshop. Rear Yard area in back of Garage would make a great area for a Fire Pit or Gazebo? Located in the cozy Historic District and within walking distance to downtown shops, restaurants, marinas, and Washington College. Short walk to the Chester River ! Would make a solid rental. this property boasts a spacious layout with plenty of room for customization. Whether you're looking to flip or rent out, this property is a great opportunity to invest in your future. Don't miss out on this chance to turn this fixer-upper into your dream investment property in the heart of Chestertown. OFF STREET Parking Cash or conventional financing.

214 Calvert St, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453

$1,995,000

Welcome to paradise! This incredible estate, situated on a bluff overlooking the Fairlee River will take your breath away. Situated in a peaceful, private setting, this masterpiece of a home is graced by soaring ceilings and abundant windows, incredible new renovations throughout such as the gourmet kitchen and spa-like baths, all thoughtfully designed to maximize it's best feature, the glorious water views. The finishes by Colebrook Designs (who you can find on Instagram) are some of the best you'll ever see The entryway draws you into the thoughtfully designed living area, created to delight the most descriminating host. The beautifully appointed great room adjacent to the chefs kitchen creates a dramatic focal point on the main level, accompanied by an elegant formal dining room and a secondary living area, which features another fireplace to create those cozy evening settings. The fully customized kitchen features amazing amenities such as luxury Cafe' appliances, many upgrades in the soft close cabinetry, the island that seats 7+ people, all with expansive water views. Upstairs, you'll find an open lounge area which opens to a spacious second floor balcony, one of many glorious outdoor spaces. Moving on to the bedrooms, if you desire easy one floor living this home provides a great opportunity featuring the most amazing first floor suite. With a soaking tub and walk in shower in the bathroom that's graced by skylights, and expansive water views from the bedroom, this is a space that you'll never want to leave. Dual walk in closets and a seperate seating area rounds out this magical space. Upstairs you'll find the two spacious guest bedrooms, served by another gorgeous full bath featuring a soaking tub of its own to round out the second floor. Back downstairs before you head outside you'll find a spacious laundry area, and a thoughfully designed first floor guest bath that also features a walk in shower for your convenience to clean up after enjoying watersports in the river. And through the breezeway to the 2 car garage, where you'll find a separate room that's set up as a gym, featuring it's own handbuild sauna! And finally outside, you'll adore the spacious cedar deck that's perfectly positioned to enjoy the broad water views. Besides the deck, this space features a custom outdoor kitchen and a covered patio area perfectly positioned for cool breezes to flow through on hot summer days, all set in the beautiful, mature landscaping that bursts into a riot of color in the spring and summertime. The newly rebuild dock features 5 boat slips as well as multiple lifts for jet skis and a boat, and super easy access to the great expanse of the Chesapeake, with 5-6 feet MLW depth at the dock. All of this is set in the beautiful neighborhood of Great Oak Landing, which features access to a 350 slip marina, restaurants, a community pool, beach, and a 9 hole executive golf course, all of which are a short walk or golf cart ride away, all for an annual membership fee of only $350! This will make an amazing home for its next owners, and would also make an amazing vacation rental for those who would choose to not live here full time. Make the most of your summers to come in this glorious home, come take a tour while it's still available!

5 Beds ⋅ 4 Baths

Welcome to paradise! This incredible estate, situated on a bluff overlooking the Fairlee River will take your breath away. Situated in a peaceful, private setting, this masterpiece of a home is graced by soaring ceilings and abundant windows, incredible new renovations throughout such as the gourmet kitchen and spa-like baths, all thoughtfully designed to maximize it's best feature, the glorious water views. The finishes by Colebrook Designs (who you can find on Instagram) are some of the best you'll ever see The entryway draws you into the thoughtfully designed living area, created to delight the most descriminating host. The beautifully appointed great room adjacent to the chefs kitchen creates a dramatic focal point on the main level, accompanied by an elegant formal dining room and a secondary living area, which features another fireplace to create those cozy evening settings. The fully customized kitchen features amazing amenities such as luxury Cafe' appliances, many upgrades in the soft close cabinetry, the island that seats 7+ people, all with expansive water views. Upstairs, you'll find an open lounge area which opens to a spacious second floor balcony, one of many glorious outdoor spaces. Moving on to the bedrooms, if you desire easy one floor living this home provides a great opportunity featuring the most amazing first floor suite. With a soaking tub and walk in shower in the bathroom that's graced by skylights, and expansive water views from the bedroom, this is a space that you'll never want to leave. Dual walk in closets and a seperate seating area rounds out this magical space. Upstairs you'll find the two spacious guest bedrooms, served by another gorgeous full bath featuring a soaking tub of its own to round out the second floor. Back downstairs before you head outside you'll find a spacious laundry area, and a thoughfully designed first floor guest bath that also features a walk in shower for your convenience to clean up after enjoying watersports in the river. And through the breezeway to the 2 car garage, where you'll find a separate room that's set up as a gym, featuring it's own handbuild sauna! And finally outside, you'll adore the spacious cedar deck that's perfectly positioned to enjoy the broad water views. Besides the deck, this space features a custom outdoor kitchen and a covered patio area perfectly positioned for cool breezes to flow through on hot summer days, all set in the beautiful, mature landscaping that bursts into a riot of color in the spring and summertime. The newly rebuild dock features 5 boat slips as well as multiple lifts for jet skis and a boat, and super easy access to the great expanse of the Chesapeake, with 5-6 feet MLW depth at the dock. All of this is set in the beautiful neighborhood of Great Oak Landing, which features access to a 350 slip marina, restaurants, a community pool, beach, and a 9 hole executive golf course, all of which are a short walk or golf cart ride away, all for an annual membership fee of only $350! This will make an amazing home for its next owners, and would also make an amazing vacation rental for those who would choose to not live here full time. Make the most of your summers to come in this glorious home, come take a tour while it's still available!

10108 3rd Point Rd, Chestertown

Listing courtesy of Keller Williams Elite. Contact: (717) 553-2500

$339,990

Move-in ready home in the Village at Chestertown! The Sidney is a 1,849 square foot open-concept two-story home, that features four bedrooms, and two and a half bathrooms. A welcoming foyer with a coat closet greets you as you enter your home from the cozy front porch. This open floorplan allows you and your family to spend quality time together in the spacious family room, casual dining area and kitchen. The well-appointed kitchen showcases an abundance of classic birch cabinetry, a sizeable peninsula island, stainless steel appliances and a large corner pantry. The laundry room complete with a washer and dryer is conveniently located off the kitchen on the first floor. Exit through the sliding glass doors in the dining room to enjoy your quiet patio at the back of the home. Also located on the first floor are the powder room, storage closet and an additional coat closet. Upstairs you will find the owner's suite complete with its private, double bowl vanity bathroom and walk-in closet. The additional three bedrooms allow for everyone in your family to have their own space. The Sidney includes the exclusive Smart Home® Package through ADT and a white window blind package giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

Move-in ready home in the Village at Chestertown! The Sidney is a 1,849 square foot open-concept two-story home, that features four bedrooms, and two and a half bathrooms. A welcoming foyer with a coat closet greets you as you enter your home from the cozy front porch. This open floorplan allows you and your family to spend quality time together in the spacious family room, casual dining area and kitchen. The well-appointed kitchen showcases an abundance of classic birch cabinetry, a sizeable peninsula island, stainless steel appliances and a large corner pantry. The laundry room complete with a washer and dryer is conveniently located off the kitchen on the first floor. Exit through the sliding glass doors in the dining room to enjoy your quiet patio at the back of the home. Also located on the first floor are the powder room, storage closet and an additional coat closet. Upstairs you will find the owner's suite complete with its private, double bowl vanity bathroom and walk-in closet. The additional three bedrooms allow for everyone in your family to have their own space. The Sidney includes the exclusive Smart Home® Package through ADT and a white window blind package giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

112 Flying Cloud Dr, Chestertown

Listing courtesy of DRH Realty Capital, LLC.. Contact: (667) 500-2488

$334,990

New move-in ready home in The Village at Chestertown! The Paige is a 1,646 square foot two-story home that features three bedrooms, and two and a half bathrooms. You will immediately feel at home as you enter the foyer with a coat closet and make your way into the spacious family room. With its open concept, the family room is open to the dining area and the kitchen. The well-designed kitchen offers modern white cabinets, stainless steel appliances, a peninsula island with additional room for seating and a large corner pantry. The private powder room is down the hall along with the utility closet. Upstairs you will find the spacious owner's suite complete with its private, double bowl vanity bathroom and walk-in closet. The sizeable two secondary bedrooms share a secondary bathroom and allow for everyone in your household to have their own space. The second-floor laundry room comes complete with a washer and dryer and is located near the hall linen closet. The Paige includes the exclusive Smart Home® Package through ADT and a white window blind package giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

3 Beds ⋅ 3 Baths

New move-in ready home in The Village at Chestertown! The Paige is a 1,646 square foot two-story home that features three bedrooms, and two and a half bathrooms. You will immediately feel at home as you enter the foyer with a coat closet and make your way into the spacious family room. With its open concept, the family room is open to the dining area and the kitchen. The well-designed kitchen offers modern white cabinets, stainless steel appliances, a peninsula island with additional room for seating and a large corner pantry. The private powder room is down the hall along with the utility closet. Upstairs you will find the spacious owner's suite complete with its private, double bowl vanity bathroom and walk-in closet. The sizeable two secondary bedrooms share a secondary bathroom and allow for everyone in your household to have their own space. The second-floor laundry room comes complete with a washer and dryer and is located near the hall linen closet. The Paige includes the exclusive Smart Home® Package through ADT and a white window blind package giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

110 Flying Cloud Dr, Chestertown

Listing courtesy of DRH Realty Capital, LLC.. Contact: (667) 500-2488

$334,990

The Sidney, a move-in ready 1,849 square-foot open concept two-story home, features four bedrooms, and two and a half bathrooms. A welcoming foyer with a coat closet greets you as you enter your home from the cozy front porch. This open floorplan allows you and your family to spend quality time together in the spacious family room, casual dining area and kitchen. The well-appointed kitchen showcases an abundance of stylish gray cabinetry, a sizeable peninsula island, stainless steel appliances and a large corner pantry. The laundry room complete with a washer and dryer is conveniently located off the kitchen on the first floor. Exit through the sliding glass doors in the dining room to enjoy your quiet patio at the back of the home. Also located on the first floor are the powder room, storage closet and an additional coat closet. Upstairs you will find the owner's suite complete with its private, double bowl vanity bathroom and walk-in closet. The additional three bedrooms allow for everyone in your family to have their own space. The Sidney includes the exclusive Smart Home® Package through ADT and a white window blind package giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

The Sidney, a move-in ready 1,849 square-foot open concept two-story home, features four bedrooms, and two and a half bathrooms. A welcoming foyer with a coat closet greets you as you enter your home from the cozy front porch. This open floorplan allows you and your family to spend quality time together in the spacious family room, casual dining area and kitchen. The well-appointed kitchen showcases an abundance of stylish gray cabinetry, a sizeable peninsula island, stainless steel appliances and a large corner pantry. The laundry room complete with a washer and dryer is conveniently located off the kitchen on the first floor. Exit through the sliding glass doors in the dining room to enjoy your quiet patio at the back of the home. Also located on the first floor are the powder room, storage closet and an additional coat closet. Upstairs you will find the owner's suite complete with its private, double bowl vanity bathroom and walk-in closet. The additional three bedrooms allow for everyone in your family to have their own space. The Sidney includes the exclusive Smart Home® Package through ADT and a white window blind package giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

106 Flying Cloud Dr, Chestertown

Listing courtesy of DRH Realty Capital, LLC.. Contact: (667) 500-2488

$625,000

Enjoy water views from this Eastern Shore two-story brick condo that is just a short walk from downtown Historic Chestertown parks, shops and dining. A major renovation in 2014 included a new kitchen and new baths. Bright with natural light and designed for first floor living, the home offers a spacious primary master suite, living room, half bath, kitchen and dining area opening to a deck. The inviting living room features a cathedral ceiling and wood-burning fireplace. The second floor has a comfortable, flexible layout with two bedrooms and a full bath. Another sought-after amenity is a detached over size two-car garage with storage. Founded in 1706, Chestertown is set on the banks of the Chester River and is home to Washington College. Brick sidewalks are lined with lovely period homes, shops, bakeries, galleries, theatre, oyster bar and restaurants. Residents and visitors alike enjoy the river walk, parks, farmers market, walking trails, community activities and annual festivals. River cruises are available on the Chester River Packet and Schooner Sultana. Chestertown is located about 90 minutes from Washington, D.C. and Philadelphia and 1-hour from Wilmington.

3 Beds ⋅ 3 Baths

Enjoy water views from this Eastern Shore two-story brick condo that is just a short walk from downtown Historic Chestertown parks, shops and dining. A major renovation in 2014 included a new kitchen and new baths. Bright with natural light and designed for first floor living, the home offers a spacious primary master suite, living room, half bath, kitchen and dining area opening to a deck. The inviting living room features a cathedral ceiling and wood-burning fireplace. The second floor has a comfortable, flexible layout with two bedrooms and a full bath. Another sought-after amenity is a detached over size two-car garage with storage. Founded in 1706, Chestertown is set on the banks of the Chester River and is home to Washington College. Brick sidewalks are lined with lovely period homes, shops, bakeries, galleries, theatre, oyster bar and restaurants. Residents and visitors alike enjoy the river walk, parks, farmers market, walking trails, community activities and annual festivals. River cruises are available on the Chester River Packet and Schooner Sultana. Chestertown is located about 90 minutes from Washington, D.C. and Philadelphia and 1-hour from Wilmington.

407 S Cross St Unit #4, Chestertown

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

$250,000

Lovely Renovated Farm/Folk style home with Public water and sewer home in the village of Fairlee, just 10 minutes to downtown Chestertown. New electric, plumbing, and drywall. The washer/dryer and hot water tank can be moved upstairs. The owner started to renovate to make 2 apartments, but the floor plan can be readjusted. Move-in ready. Large grassy yard. Quiet neighborhood. A quick settlement is fine.

Lovely Renovated Farm/Folk style home with Public water and sewer home in the village of Fairlee, just 10 minutes to downtown Chestertown. New electric, plumbing, and drywall. The washer/dryer and hot water tank can be moved upstairs. The owner started to renovate to make 2 apartments, but the floor plan can be readjusted. Move-in ready. Large grassy yard. Quiet neighborhood. A quick settlement is fine.

23073 Parsons Rd, Chestertown

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

$265,000

This wonderfully renovated, 3 bedroom, 2 bath home is move in ready! Open concept living featuring vaulted ceilings, hardwood floors, granite counters, stainless steel appliances, recessed lighting, french doors to the deck. The home has a new roof and siding as well as new AC and duct work within the last 2 years. Schedule a showing today, this one will not last long! AS IS

This wonderfully renovated, 3 bedroom, 2 bath home is move in ready! Open concept living featuring vaulted ceilings, hardwood floors, granite counters, stainless steel appliances, recessed lighting, french doors to the deck. The home has a new roof and siding as well as new AC and duct work within the last 2 years. Schedule a showing today, this one will not last long! AS IS

24745 Langford Rd, Chestertown

Listing courtesy of Douglas Realty, LLC. Contact: (410) 255-3690

$600,000

BUY THIS AWESOME HOME FOR LESS THAN $2,800 PER MONTH OR TRADE! SPECIAL FINANCING AVAILABLE: RATES LESS THAN 4.6% FOR THOSE WHO QUALIFY. OCCUPYING A VAST, RESIDENTIAL BLOCK ALREADY SUBDIVIDED FOR FUTURE DEVELOPMENT, THIS UNIQUE HOME BLENDS COUNTRY SERENITY AND URBAN CONVENIENCE WITH THE HISTORIC CHESTERTOWN JUST A FEW MINUTES AWAY. IT IS A SUPER RARE OFFERING WITH 10 ACRES OF LAND. INCLUDING HORSE STABLES A LARGE BARN AND SPACE TO STORE YOUR FARM EQUPMENT. IMAGINE ALL THE POTENTIAL! THE RESIDENCE ENJOYS OVER 2,300 SF OF FINISHED LIVING SPACE FEATURING A 3-SEASONS ROOM IN FRONT, A LARGE KITCHEN WITH PANTRY AND LAUNDRY AREA, BEAUTIFUL WOOD FLOORS IN MAIN AREAS, MUD ROOM AT THE BACK, PLUS NEW ROOF, BACK UP GENERATOR, AND DECK FOR ENTERTAINING. THE GENEROUS MASTER SUITE EASILY TRANSITIONS TO THE OUTDOOR THROUGH A SLIDER. BONUS ROOMS INCLUDE A SMALL OFFICE OFF OF THE FAMILY ROOM AND A SECOND OFFICE SPACE RIGHT IN THE HALL. IT'S IDYLLIC FOR THOSE LOOKING FOR PEACE AND PRIVACY. RENOVATE FOR COMFORT OR EXPLORE ITS DEVELOPMENT POTENTIAL. OPEN HOUSE EVERY DAY - CALL FOR TIMES!

BUY THIS AWESOME HOME FOR LESS THAN $2,800 PER MONTH OR TRADE! SPECIAL FINANCING AVAILABLE: RATES LESS THAN 4.6% FOR THOSE WHO QUALIFY. OCCUPYING A VAST, RESIDENTIAL BLOCK ALREADY SUBDIVIDED FOR FUTURE DEVELOPMENT, THIS UNIQUE HOME BLENDS COUNTRY SERENITY AND URBAN CONVENIENCE WITH THE HISTORIC CHESTERTOWN JUST A FEW MINUTES AWAY. IT IS A SUPER RARE OFFERING WITH 10 ACRES OF LAND. INCLUDING HORSE STABLES A LARGE BARN AND SPACE TO STORE YOUR FARM EQUPMENT. IMAGINE ALL THE POTENTIAL! THE RESIDENCE ENJOYS OVER 2,300 SF OF FINISHED LIVING SPACE FEATURING A 3-SEASONS ROOM IN FRONT, A LARGE KITCHEN WITH PANTRY AND LAUNDRY AREA, BEAUTIFUL WOOD FLOORS IN MAIN AREAS, MUD ROOM AT THE BACK, PLUS NEW ROOF, BACK UP GENERATOR, AND DECK FOR ENTERTAINING. THE GENEROUS MASTER SUITE EASILY TRANSITIONS TO THE OUTDOOR THROUGH A SLIDER. BONUS ROOMS INCLUDE A SMALL OFFICE OFF OF THE FAMILY ROOM AND A SECOND OFFICE SPACE RIGHT IN THE HALL. IT'S IDYLLIC FOR THOSE LOOKING FOR PEACE AND PRIVACY. RENOVATE FOR COMFORT OR EXPLORE ITS DEVELOPMENT POTENTIAL. OPEN HOUSE EVERY DAY - CALL FOR TIMES!

24543 Chestertown Rd, Chestertown

Listing courtesy of Your Home Sold Guaranteed Realty. Contact: (410) 793-1616

$805,000

Check out Chester River Landing's newest construction! This three bedroom, three and a half bath, townhouse is a spacious end unit with incredible views of the Chester River and is built with the finest finishes. The main first level includes a large open floorplan design great for socializing and entertaining guests and a study off of the front foyer. Upstairs includes three bedroom suites all with their own bath. The primary bedroom has panoramic views of the river and sliding glass doors to the balcony. This home is built with an elevator shaft for future use if necessary. Enjoy all that the community has to offer, clubs and social gatherings, bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short ways up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Check out Chester River Landing's newest construction! This three bedroom, three and a half bath, townhouse is a spacious end unit with incredible views of the Chester River and is built with the finest finishes. The main first level includes a large open floorplan design great for socializing and entertaining guests and a study off of the front foyer. Upstairs includes three bedroom suites all with their own bath. The primary bedroom has panoramic views of the river and sliding glass doors to the balcony. This home is built with an elevator shaft for future use if necessary. Enjoy all that the community has to offer, clubs and social gatherings, bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short ways up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Landing Ln Unit #11, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665

$815,000

Check out Chester River Landing's newest construction! This middle unit, three bedroom, three and a half bath townhouse is spacious and has incredible views of the Chester River. Built with the finest finishes, the main first level includes a large open floorplan design great for socializing and entertaining guests and a study off of the front foyer. Upstairs includes three bedroom suites all with their own bath. The primary bedroom has panoramic views of the river and sliding glass doors to the balcony. This home is built with an elevator shaft for future use if necessary. Enjoy all that the community has to offer, clubs and social gatherings, bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short ways up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Check out Chester River Landing's newest construction! This middle unit, three bedroom, three and a half bath townhouse is spacious and has incredible views of the Chester River. Built with the finest finishes, the main first level includes a large open floorplan design great for socializing and entertaining guests and a study off of the front foyer. Upstairs includes three bedroom suites all with their own bath. The primary bedroom has panoramic views of the river and sliding glass doors to the balcony. This home is built with an elevator shaft for future use if necessary. Enjoy all that the community has to offer, clubs and social gatherings, bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short ways up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Landing Ln Unit #12, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665

$569,000

Welcome to this charming and elegant 2 bedroom, 2.5 bathroom condo nestled in a tranquil water-oriented community near the Chester River in the historic town of Chestertown, Maryland. This gorgeous home is situated in a prime location, offering easy access to nearby shops, cafes, and restaurants. As you step inside, you'll be greeted by a warm and inviting atmosphere that seamlessly blends classic charm with modern convenience. On the main level , you'll find access from the attached garage or front porch. Off the spacious hallway you have the enclosed Washer/Dryer unit, storage closet and full bathroom. French Doors leading to the first floor study with a bedroom to the left and straight ahead to the downstairs screened in porch overlooking the serene community pond. The upper level features an open-concept living area that's perfect for entertaining. You'll love the spacious kitchen with its stainless steel appliances, sleek countertops, and ample cabinet space. The dining area is flooded with natural light, creating the perfect ambiance for family meals and gatherings with friends. Enter the upstairs porch overlooking the pond with views of the pond, this is true indoor/outdoor entertaining. The upstairs primary suite is a true retreat, complete with a luxurious en-suite bathroom featuring double sinks, shower and stunning finishes. A huge walk in closet completes this experience. This home is also ideally situated within a water-oriented community, providing easy access to boating, fishing, and other water activities. The community offers a dock, boat ramp, as well as grilling areas and a swimming pool for your enjoyment. With its stunning finishes, prime location, and luxurious amenities, this 2 bedroom, 2.5 bathroom condo is the perfect place to call home. Don't miss your chance to experience the best that Chestertown has to offer!

2 Beds ⋅ 3 Baths

Welcome to this charming and elegant 2 bedroom, 2.5 bathroom condo nestled in a tranquil water-oriented community near the Chester River in the historic town of Chestertown, Maryland. This gorgeous home is situated in a prime location, offering easy access to nearby shops, cafes, and restaurants. As you step inside, you'll be greeted by a warm and inviting atmosphere that seamlessly blends classic charm with modern convenience. On the main level , you'll find access from the attached garage or front porch. Off the spacious hallway you have the enclosed Washer/Dryer unit, storage closet and full bathroom. French Doors leading to the first floor study with a bedroom to the left and straight ahead to the downstairs screened in porch overlooking the serene community pond. The upper level features an open-concept living area that's perfect for entertaining. You'll love the spacious kitchen with its stainless steel appliances, sleek countertops, and ample cabinet space. The dining area is flooded with natural light, creating the perfect ambiance for family meals and gatherings with friends. Enter the upstairs porch overlooking the pond with views of the pond, this is true indoor/outdoor entertaining. The upstairs primary suite is a true retreat, complete with a luxurious en-suite bathroom featuring double sinks, shower and stunning finishes. A huge walk in closet completes this experience. This home is also ideally situated within a water-oriented community, providing easy access to boating, fishing, and other water activities. The community offers a dock, boat ramp, as well as grilling areas and a swimming pool for your enjoyment. With its stunning finishes, prime location, and luxurious amenities, this 2 bedroom, 2.5 bathroom condo is the perfect place to call home. Don't miss your chance to experience the best that Chestertown has to offer!

103 Landing Ln, Chestertown

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

$598,500

Your dream house awaits in the most perfect location! This delightful custom built home, being offered on one of the most sought after streets in Downtown Chestertown, and perfectly situated at the 'quiet end' of Queen Street, is only one block to the Marina, restaurants/shops, and overlooks Wilmer Park, with the Chester River beyond. Although this home has the true look of a an Period Colonial Home, it was actually newly constructed in 2006, on the original footprint of an older historic home. The owners have not only built , but meticulously cared for, and loved it throughout the years, being located so conveniently to all the things everyone loves about Historic Chestertown. As you walk up to the house you will find the porches very inviting and you will get so much enjoyment being out there at any time of day. As you come in you will find a front living room with a wood burning fireplace that adds warmth and enjoyment to the whole home. through to a cozy dining room or extended living room . Next, a pristine kitchen, refreshing and full of light, which offers plenty of storage and counter space. There's a main level laundry offered and then what could be a Primary Bedroom at the back of the house (with a full bath), or it can be used as a family room, as it is currently now. Through out the house which is not standard, but was thoughtfully and custom added, are very ample, oversized closet spaces for plenty of storage. You will also find an upstairs staircase to the floored attic that allows plenty of room for all your additional storage needs. On the second floor you have the option for a very spacious primary bedroom at the back of the house and an additional 2 rooms which have been a guest room and office . Through out the house you will find gorgeous plantation shutters to help allow the sun in when you want or help keep it out. Very tastefully done. As you settle into the heart of downtown you will be able to enjoy the Traditional Farmers Market on Saturdays , The well known Tea Party Festival , The Dickens Holiday Celebration and Down Rigging Weekend, just to name a few. The Garfield Center is always a favorite with a line up of theatrical shows and musical attractions. You will quickly fall into your favorite enjoyments and pass times that Chestertown has to offer . Some of the favorites of downtown will be the coffee spots, eateries and dining options which can all be with in within a few minute walk. Many details about this house can still be shared but come see and feel the welcome and the ease of a well built costume home that has been well taken care off and ease of low maintenance.

Your dream house awaits in the most perfect location! This delightful custom built home, being offered on one of the most sought after streets in Downtown Chestertown, and perfectly situated at the 'quiet end' of Queen Street, is only one block to the Marina, restaurants/shops, and overlooks Wilmer Park, with the Chester River beyond. Although this home has the true look of a an Period Colonial Home, it was actually newly constructed in 2006, on the original footprint of an older historic home. The owners have not only built , but meticulously cared for, and loved it throughout the years, being located so conveniently to all the things everyone loves about Historic Chestertown. As you walk up to the house you will find the porches very inviting and you will get so much enjoyment being out there at any time of day. As you come in you will find a front living room with a wood burning fireplace that adds warmth and enjoyment to the whole home. through to a cozy dining room or extended living room . Next, a pristine kitchen, refreshing and full of light, which offers plenty of storage and counter space. There's a main level laundry offered and then what could be a Primary Bedroom at the back of the house (with a full bath), or it can be used as a family room, as it is currently now. Through out the house which is not standard, but was thoughtfully and custom added, are very ample, oversized closet spaces for plenty of storage. You will also find an upstairs staircase to the floored attic that allows plenty of room for all your additional storage needs. On the second floor you have the option for a very spacious primary bedroom at the back of the house and an additional 2 rooms which have been a guest room and office . Through out the house you will find gorgeous plantation shutters to help allow the sun in when you want or help keep it out. Very tastefully done. As you settle into the heart of downtown you will be able to enjoy the Traditional Farmers Market on Saturdays , The well known Tea Party Festival , The Dickens Holiday Celebration and Down Rigging Weekend, just to name a few. The Garfield Center is always a favorite with a line up of theatrical shows and musical attractions. You will quickly fall into your favorite enjoyments and pass times that Chestertown has to offer . Some of the favorites of downtown will be the coffee spots, eateries and dining options which can all be with in within a few minute walk. Many details about this house can still be shared but come see and feel the welcome and the ease of a well built costume home that has been well taken care off and ease of low maintenance.

223 S Queen St, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$212,000

Two apartment dwelling sited on 2.51 acres zoned Village offers town water/sewer with units served with separate electric meters. The large spacious open area behind the dwelling offers great potential for possible development ...details for same need to be researched with county planning and zoning.

Two apartment dwelling sited on 2.51 acres zoned Village offers town water/sewer with units served with separate electric meters. The large spacious open area behind the dwelling offers great potential for possible development ...details for same need to be researched with county planning and zoning.

8900 Fairlee Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$212,000

Two apartment dwelling sited on 2.51 acres zoned Village offers town water/sewer with units served with separate electric meters. The large spacious open area behind the dwelling offers great potential for possible development ...details for same need to be researched with county planning and zoning.

8900 Fairlee Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$259,000

Adorable renovation of this charming rancher. Nice corner fenced-in lot in a private setting. The gourmet kitchen features stainless appliances, granite countertops, gas stove and convenient laundry closet. A large living room is great for entertaining with a cozy propane fireplace. Tolchester Estates has a private beach area for homeowners to enjoy. The Shanty at Tolchester Marina offers entertainment, dining and a beach bar! Store your boat nearby at the marina and enjoy easy access to the Chesapeake Bay!

2 Beds ⋅ 1 Baths

Adorable renovation of this charming rancher. Nice corner fenced-in lot in a private setting. The gourmet kitchen features stainless appliances, granite countertops, gas stove and convenient laundry closet. A large living room is great for entertaining with a cozy propane fireplace. Tolchester Estates has a private beach area for homeowners to enjoy. The Shanty at Tolchester Marina offers entertainment, dining and a beach bar! Store your boat nearby at the marina and enjoy easy access to the Chesapeake Bay!

21239 Kansas Ave, Chestertown

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$319,990

The Sidney, a move-in ready 1,849 square-foot open concept two-story home, features four bedrooms, and two and a half bathrooms. A welcoming foyer with a coat closet greets you as you enter your home from the cozy front porch. This open floorplan allows you and your family to spend quality time together in the spacious family room, casual dining area and kitchen. The well-appointed kitchen showcases an abundance of modern gray cabinetry, a sizeable peninsula island, stainless steel appliances and a large corner pantry. The laundry room complete with a washer and dryer is conveniently located off the kitchen on the first floor. Exit through the sliding glass doors in the dining room to enjoy your quiet patio at the back of the home. Also located on the first floor are the powder room, storage closet and an additional coat closet. Upstairs you will find the owner's suite complete with its private, double bowl vanity bathroom and walk-in closet. The additional three bedrooms allow for everyone in your family to have their own space. The Sidney includes the exclusive Smart Home® Package through ADT and a white window blind package giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

The Sidney, a move-in ready 1,849 square-foot open concept two-story home, features four bedrooms, and two and a half bathrooms. A welcoming foyer with a coat closet greets you as you enter your home from the cozy front porch. This open floorplan allows you and your family to spend quality time together in the spacious family room, casual dining area and kitchen. The well-appointed kitchen showcases an abundance of modern gray cabinetry, a sizeable peninsula island, stainless steel appliances and a large corner pantry. The laundry room complete with a washer and dryer is conveniently located off the kitchen on the first floor. Exit through the sliding glass doors in the dining room to enjoy your quiet patio at the back of the home. Also located on the first floor are the powder room, storage closet and an additional coat closet. Upstairs you will find the owner's suite complete with its private, double bowl vanity bathroom and walk-in closet. The additional three bedrooms allow for everyone in your family to have their own space. The Sidney includes the exclusive Smart Home® Package through ADT and a white window blind package giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

108 Flying Cloud Dr, Chestertown

Listing courtesy of DRH Realty Capital, LLC.. Contact: (667) 500-2488

$319,990

This move-in ready Paige is a 1,646 square foot two-story home, that features three bedrooms, and two and a half bathrooms. You will immediately feel at home as you enter the foyer with a coat closet and make your way into the spacious family room. With its open concept, the family room is open to the dining area and the kitchen. The well-designed kitchen offers stainless steel appliances, classic white cabinets, a peninsula island with additional room for seating and a large corner pantry. The private powder room is down the hall along with the utility closet. Upstairs you will find the spacious owner's suite complete with its private, double bowl vanity bathroom and walk-in closet. The sizeable two secondary bedrooms share a secondary bathroom and allow for everyone in your household to have their own space. The second-floor laundry room comes complete with a washer and dryer and is located near the hall linen closet. The Paige includes a white window treatment package and the exclusive Smart Home® Package giving you complete peace of mind living in your new home.

3 Beds ⋅ 3 Baths

This move-in ready Paige is a 1,646 square foot two-story home, that features three bedrooms, and two and a half bathrooms. You will immediately feel at home as you enter the foyer with a coat closet and make your way into the spacious family room. With its open concept, the family room is open to the dining area and the kitchen. The well-designed kitchen offers stainless steel appliances, classic white cabinets, a peninsula island with additional room for seating and a large corner pantry. The private powder room is down the hall along with the utility closet. Upstairs you will find the spacious owner's suite complete with its private, double bowl vanity bathroom and walk-in closet. The sizeable two secondary bedrooms share a secondary bathroom and allow for everyone in your household to have their own space. The second-floor laundry room comes complete with a washer and dryer and is located near the hall linen closet. The Paige includes a white window treatment package and the exclusive Smart Home® Package giving you complete peace of mind living in your new home.

102 Flying Cloud Dr, Chestertown

Listing courtesy of DRH Realty Capital, LLC.. Contact: (667) 500-2488

$859,900

18th century historic home in downtown Chestertown with a separate carriage house! The main home features 3 bedrooms all with en-suite baths. The carriage house has an additional 2 bedrooms and 2 baths with separate laundry and a brick patio. Entrances to the property from Queen St. and Horsey Lane, 2 driveways with plenty of parking spaces. Original wood flooring throughout much of the house. The first floor features a living room, dining room, kitchen, and half bath. New owner to add vanity and toilet to one of the upstairs baths. Second-floor laundry room. Lovely landscaping and fenced-in yard between the main house and the carriage house. Just a short walk to the heart of downtown Chestertown. Definitely a rare find.