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Nestled in the serene SASSAFRAS subdivision, this ranch-style residence offers a harmonious blend of comfort and elegance. Built in 2007, this home showcases a thoughtful design that emphasizes an open floor plan, perfect for both relaxation and entertaining. Step inside to discover a warm and inviting atmosphere, highlighted by luxury vinyl plank flooring that flows seamlessly throughout the living spaces. The heart of the home is the country-style kitchen, equipped with modern appliances including a built-in microwave, dishwasher, and electric oven/range. The kitchen effortlessly transitions into a cozy breakfast area, making it an ideal spot for morning coffee or casual meals. The spacious living area is designed for gatherings, featuring ample natural light from double-hung windows that frame picturesque views of the garden and lawn. The layout includes three well-appointed bedrooms, with the primary suite offering a private oasis complete with a soaking tub and a stall shower in the en-suite bathroom. Each bedroom provides a tranquil retreat, ensuring comfort and privacy for all. This property boasts a generous 0.47-acre lot, meticulously cleared to create a beautiful outdoor space. The front yard welcomes you with lush greenery, while the rear yard offers a perfect canvas for gardening or outdoor activities. With side yards that provide additional space, the possibilities for outdoor enjoyment are endless. Enjoy the peaceful surroundings and the charm of the neighborhood, where the views of the street and garden create a picturesque backdrop for your daily life. The additional shed on the property provides extra storage, enhancing the functionality of this lovely home. This residence is not just a house; it's a lifestyle. Experience the perfect blend of modern amenities and serene living, all within a community that values comfort and tranquility. Embrace the opportunity to make this exceptional property your own, where every detail has been crafted for a life of ease and enjoyment.

33741 Galena Sassafras Rd, Galena

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$599,900

Welcome to 13981 Mill Creek Lane - a wonderful 3 bedroom, 2.5 bathroom cape cod with 2,000+ square feet of living space, screened porch, 2-car attached garage, and 3-car detached garage all on 6 acres in Galena, MD! Upon entry, you'll notice the incredible amount of parking and the convenient circular driveway, making it easy for residents and guests to come and go seamlessly. The main living area features a wood-burning fireplace, great for staying cozy in the cooler months. The eat-in kitchen, complete with large island, has been updated with granite counters and features tile flooring, plenty of cabinet space, and tons of room for a table. Just off the kitchen, the screened porch is a wonderful place to hang, eat crabs in the summer months, and enjoy morning coffee. Down the hall, a formal dining room can fit a massive table to accommodate friends and family, or it can be converted into an office or recreation room. A first floor bedroom and full bathroom are conveniently located on the far side of the home for privacy. Rounding out the main level is the laundry room and half bathroom. Upstairs, the enormous primary bedroom features a walk-in closet, massive bonus room with mini split heating and cooling, and access to the primary bathroom. Down the hall, an additional bedroom rounds out the living space. The detached 3 car garage is more than just a garage - it could serve as an excellent workshop and also features an additional covered area on the back of the garage, great for lawncare storage. Use your 6 acres creatively! If you're a gardener or a hunter, this could be your paradise! Bring your goats and horses! This home is great for the car enthusiast, too - the 5 total garage spaces alone make for an incredibly rare property! There are so many awesome possibilities at 13981 Mill Creek Lane!

Welcome to 13981 Mill Creek Lane - a wonderful 3 bedroom, 2.5 bathroom cape cod with 2,000+ square feet of living space, screened porch, 2-car attached garage, and 3-car detached garage all on 6 acres in Galena, MD! Upon entry, you'll notice the incredible amount of parking and the convenient circular driveway, making it easy for residents and guests to come and go seamlessly. The main living area features a wood-burning fireplace, great for staying cozy in the cooler months. The eat-in kitchen, complete with large island, has been updated with granite counters and features tile flooring, plenty of cabinet space, and tons of room for a table. Just off the kitchen, the screened porch is a wonderful place to hang, eat crabs in the summer months, and enjoy morning coffee. Down the hall, a formal dining room can fit a massive table to accommodate friends and family, or it can be converted into an office or recreation room. A first floor bedroom and full bathroom are conveniently located on the far side of the home for privacy. Rounding out the main level is the laundry room and half bathroom. Upstairs, the enormous primary bedroom features a walk-in closet, massive bonus room with mini split heating and cooling, and access to the primary bathroom. Down the hall, an additional bedroom rounds out the living space. The detached 3 car garage is more than just a garage - it could serve as an excellent workshop and also features an additional covered area on the back of the garage, great for lawncare storage. Use your 6 acres creatively! If you're a gardener or a hunter, this could be your paradise! Bring your goats and horses! This home is great for the car enthusiast, too - the 5 total garage spaces alone make for an incredibly rare property! There are so many awesome possibilities at 13981 Mill Creek Lane!

13981 Mill Creek Ln, Galena

Listing courtesy of RE/MAX Chesapeake. Contact:

$1,500,000

Stunningly renovated home in Shorewood Estates. Your back yard is Swantown Creek. Professional pics and rest of the details are coming. Expected on market date is 9/25. Everything inside and out has been renovated to 11 out of 10. A truly incredibly rare opportunity that will need to be seen to be believed....but believe it!

Stunningly renovated home in Shorewood Estates. Your back yard is Swantown Creek. Professional pics and rest of the details are coming. Expected on market date is 9/25. Everything inside and out has been renovated to 11 out of 10. A truly incredibly rare opportunity that will need to be seen to be believed....but believe it!

13876 Swantown Creek Rd, Galena

Listing courtesy of Patterson-Schwartz - Greenville. Contact: 3024294500

$897,000

Waterfront Living at the Head of Still Pond Creek Well-maintained and beautifully situated, this 3-bedroom, 3-bath waterfront home offers a peaceful setting at the head of Still Pond Creek. Enjoy the best of Eastern Shore living with serene water views, a quiet natural backdrop, and easy access to the Chesapeake bay. Conveniently located with very easy access to Chestertown and points north, this property is ideal as a full-time residence, weekend retreat, or waterfront getaway. A rare opportunity to enjoy comfort, convenience, and the charm of life on Still Pond Creek.

Waterfront Living at the Head of Still Pond Creek Well-maintained and beautifully situated, this 3-bedroom, 3-bath waterfront home offers a peaceful setting at the head of Still Pond Creek. Enjoy the best of Eastern Shore living with serene water views, a quiet natural backdrop, and easy access to the Chesapeake bay. Conveniently located with very easy access to Chestertown and points north, this property is ideal as a full-time residence, weekend retreat, or waterfront getaway. A rare opportunity to enjoy comfort, convenience, and the charm of life on Still Pond Creek.

25411 Paradise Point Ln, Worton

Listing courtesy of Gunther-McClary Real Estate. Contact:

$229,000

This 3-bedroom, 1-bathroom ranch-style home in Quaker Estates offers a solid investment opportunity with a total finished area of 936 sq ft. Built in 1963, the property features essential appliances including a refrigerator and stove, ensuring immediate functionality for tenants or future buyers. The average condition of the home allows for potential value-add renovations, which can significantly increase rental income or resale value. The spacious 0.34-acre lot provides ample outdoor space, while off-street and driveway parking enhances convenience for residents. A shed on the property offers additional storage options, appealing to renters seeking practicality. With no pool maintenance costs and a straightforward layout, this property is low-maintenance, making it an attractive option for investors looking to maximize returns. The combination of location, features, and potential for appreciation makes this property a compelling addition to any real estate portfolio.

This 3-bedroom, 1-bathroom ranch-style home in Quaker Estates offers a solid investment opportunity with a total finished area of 936 sq ft. Built in 1963, the property features essential appliances including a refrigerator and stove, ensuring immediate functionality for tenants or future buyers. The average condition of the home allows for potential value-add renovations, which can significantly increase rental income or resale value. The spacious 0.34-acre lot provides ample outdoor space, while off-street and driveway parking enhances convenience for residents. A shed on the property offers additional storage options, appealing to renters seeking practicality. With no pool maintenance costs and a straightforward layout, this property is low-maintenance, making it an attractive option for investors looking to maximize returns. The combination of location, features, and potential for appreciation makes this property a compelling addition to any real estate portfolio.

7415 Wilkins Ln, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$363,000

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

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

206 Maplewood Ln, Galena

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

$325,000

This charming 4-bedroom cottage in Rock Hall offers an easy Eastern Shore getaway with the option to purchase completely turnkey with furnishings. Situated on .31 acres, the home has seen several recent updates, including new flooring, fresh paint, quartz countertops and backsplash, new dishwasher, refrigerator and microwave, updated fixtures and ceiling fans, and more. A screened porch provides additional space to relax. Outdoor improvements include new landscaping, an updated fire pit area, and a new storage shed. Located close to Rock Hall’s restaurants, bars, marinas, and Ferry Park Beach, the property puts you within easy reach of everything that makes this waterfront town such a popular destination. The low-maintenance setup makes it well suited as a full-time residence, second home, or investment/short-term rental opportunity. Move right in and start enjoying Rock Hall.

4 Beds ⋅ 1 Baths

This charming 4-bedroom cottage in Rock Hall offers an easy Eastern Shore getaway with the option to purchase completely turnkey with furnishings. Situated on .31 acres, the home has seen several recent updates, including new flooring, fresh paint, quartz countertops and backsplash, new dishwasher, refrigerator and microwave, updated fixtures and ceiling fans, and more. A screened porch provides additional space to relax. Outdoor improvements include new landscaping, an updated fire pit area, and a new storage shed. Located close to Rock Hall’s restaurants, bars, marinas, and Ferry Park Beach, the property puts you within easy reach of everything that makes this waterfront town such a popular destination. The low-maintenance setup makes it well suited as a full-time residence, second home, or investment/short-term rental opportunity. Move right in and start enjoying Rock Hall.

20705 Wilkins Ave, Rock Hall

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

$275,000

Welcome home! This beautifully maintained and updated property sits on a generous .45-acre lot in a lovely, quiet neighborhood, with a peaceful, wooded backdrop for added privacy. Renovated in 2017, this home offers numerous upgrades and thoughtful improvements, including hardwood floors, newer windows and doors, updated HVAC, and a newer roof. The kitchen features 42-inch cabinetry, granite countertops, and stainless steel appliances, while the custom ceramic-tile bath adds an extra touch of style. Enjoy the best of outdoor living from the fabulous screened-in porch and deck, perfect for relaxing, entertaining, or simply enjoying the tranquil surroundings. A large parking area provides plenty of space for family and guests, and the partial basement offers additional storage or flexible-use space. With so many major updates already completed, there is little left to do but move in, relax, and enjoy! A wonderful opportunity for anyone looking for a move-in-ready home with space, privacy, and a great neighborhood setting. Location is a bonus! Just minutes from historic downtown Chestertown, offering convenient access to local shopping, restaurants, movies, and a variety of waterfront activities. Enjoy the peaceful feel of a quiet neighborhood while being close to everything Chestertown has to offer. Schedule your tour today!

Welcome home! This beautifully maintained and updated property sits on a generous .45-acre lot in a lovely, quiet neighborhood, with a peaceful, wooded backdrop for added privacy. Renovated in 2017, this home offers numerous upgrades and thoughtful improvements, including hardwood floors, newer windows and doors, updated HVAC, and a newer roof. The kitchen features 42-inch cabinetry, granite countertops, and stainless steel appliances, while the custom ceramic-tile bath adds an extra touch of style. Enjoy the best of outdoor living from the fabulous screened-in porch and deck, perfect for relaxing, entertaining, or simply enjoying the tranquil surroundings. A large parking area provides plenty of space for family and guests, and the partial basement offers additional storage or flexible-use space. With so many major updates already completed, there is little left to do but move in, relax, and enjoy! A wonderful opportunity for anyone looking for a move-in-ready home with space, privacy, and a great neighborhood setting. Location is a bonus! Just minutes from historic downtown Chestertown, offering convenient access to local shopping, restaurants, movies, and a variety of waterfront activities. Enjoy the peaceful feel of a quiet neighborhood while being close to everything Chestertown has to offer. Schedule your tour today!

7482 Poplar Ave, Chestertown

Listing courtesy of Taylor Properties. Contact:

$315,000

Here is 24775 Langford Road, a well-maintained 3-bedroom, 1-bath home situated on 1.27 acres in a peaceful country setting just minutes from downtown Chestertown. The property features a spacious two to three-car detached garage/workshop, offering plenty of room for vehicles, storage, hobbies, or projects. A large Trex deck provides additional outdoor living and entertaining space. The home underwent extensive renovations in 2018, including the roof, windows, siding, gutters, storm doors, HVAC system, the Well was done in 2021, and partial crawl space encapsulation. Interior improvements included refinishing of the original hardwood floors and a remodeled kitchen featuring all-wood cherry cabinetry and stainless-steel appliances. With numerous major improvements already completed, garage and workshop space, and over an acre of property, this home offers comfortable country living with convenient access to Chestertown, Rock Hall and surrounding areas.

Here is 24775 Langford Road, a well-maintained 3-bedroom, 1-bath home situated on 1.27 acres in a peaceful country setting just minutes from downtown Chestertown. The property features a spacious two to three-car detached garage/workshop, offering plenty of room for vehicles, storage, hobbies, or projects. A large Trex deck provides additional outdoor living and entertaining space. The home underwent extensive renovations in 2018, including the roof, windows, siding, gutters, storm doors, HVAC system, the Well was done in 2021, and partial crawl space encapsulation. Interior improvements included refinishing of the original hardwood floors and a remodeled kitchen featuring all-wood cherry cabinetry and stainless-steel appliances. With numerous major improvements already completed, garage and workshop space, and over an acre of property, this home offers comfortable country living with convenient access to Chestertown, Rock Hall and surrounding areas.

24775 Langford Rd, Chestertown

Listing courtesy of RE/MAX Chesapeake. Contact:

$300,000

**OPEN HOUSE Sunday September 13th 11AM-1PM** This adorable rancher will soon be at the top of your "favorites" list, with a welcoming interior and plenty to love outside. Set on a spacious corner lot, you'll find a long driveway, new paver patio, vinyl privacy fencing, playset and room to roam, while the inside features a beautiful kitchen, spacious living room and updated bathroom. Cute, low maintenance and just the right size to come make your own!!

**OPEN HOUSE Sunday September 13th 11AM-1PM** This adorable rancher will soon be at the top of your "favorites" list, with a welcoming interior and plenty to love outside. Set on a spacious corner lot, you'll find a long driveway, new paver patio, vinyl privacy fencing, playset and room to roam, while the inside features a beautiful kitchen, spacious living room and updated bathroom. Cute, low maintenance and just the right size to come make your own!!

104 Lincoln Dr, Chestertown

Listing courtesy of RE/MAX Executive. Contact: 4432741900

$369,000

Discover the charm of this beautifully renovated ranch-style home in the Millington community. With 1,801 sq. ft. of exquisite living space, this residence features an open floor plan that seamlessly connects the living, dining, and kitchen areas, perfect for entertaining. Enjoy upgraded countertops, stainless steel appliances, and elegant wood floors throughout. There's a primary suite with a private bath, two guest bedrooms and full hall bath. Watch the game in your very own recreation room complete with a bar and electric fireplace. Step outside to a spacious 0.42-acre lot, complete with extensive hardscape, a patio with pergola, and a welcoming porch-ideal for outdoor relaxation. The attached garage and additional outbuildings provide ample storage. Located in a welcoming neighborhood, you'll appreciate the proximity parks, and convenient public services. Experience the perfect blend of comfort and community in this exceptional home, where every detail has been thoughtfully designed for modern living. Don't miss your chance to make it yours!

Discover the charm of this beautifully renovated ranch-style home in the Millington community. With 1,801 sq. ft. of exquisite living space, this residence features an open floor plan that seamlessly connects the living, dining, and kitchen areas, perfect for entertaining. Enjoy upgraded countertops, stainless steel appliances, and elegant wood floors throughout. There's a primary suite with a private bath, two guest bedrooms and full hall bath. Watch the game in your very own recreation room complete with a bar and electric fireplace. Step outside to a spacious 0.42-acre lot, complete with extensive hardscape, a patio with pergola, and a welcoming porch-ideal for outdoor relaxation. The attached garage and additional outbuildings provide ample storage. Located in a welcoming neighborhood, you'll appreciate the proximity parks, and convenient public services. Experience the perfect blend of comfort and community in this exceptional home, where every detail has been thoughtfully designed for modern living. Don't miss your chance to make it yours!

374 Hurtt Ave, Millington

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

$270,000

Nestled in the charming WORTON subdivision, this delightful ranch-style home, built in 2020, offers a perfect blend of modern comfort and inviting warmth. With 1,144 square feet of thoughtfully designed living space, this residence is ideal for those seeking a cozy yet functional environment. Step inside to discover an open floor plan that seamlessly connects the kitchen, dining, and living areas, creating an inviting atmosphere for gatherings and everyday living. The spacious kitchen features a convenient island, perfect for casual meals or entertaining guests. Equipped with stainless steel appliances, including a built-in microwave, dishwasher, and washer/dryer, this kitchen is both stylish and practical. The breakfast area is a lovely spot to enjoy your morning coffee while basking in the natural light that fills the space. This home boasts three well-appointed bedrooms, including a primary suite with an en-suite bathroom that features a tub shower, providing a serene retreat at the end of the day. Ceiling fans throughout the home ensure comfort year-round, while the combination of living and dining spaces enhances the sense of togetherness. Outside, the property is equally inviting. The exterior is adorned with low-maintenance vinyl siding and features exterior lighting that adds a warm glow to the evenings. A spacious deck invites you to enjoy outdoor living, whether it's hosting summer barbecues or simply unwinding with a good book. The lot backs to trees, offering a peaceful backdrop and a sense of privacy that is hard to find. The 0.14-acre lot provides ample space for gardening or play, while a handy shed offers additional storage for tools and outdoor equipment. Parking is a breeze with a dedicated driveway, ensuring convenience for you and your guests. This home is not just a place to live; it's a sanctuary where comfort meets functionality. With its excellent condition and modern amenities, it's ready for you to make it your own. Don't miss the opportunity to experience the warmth and charm of this beautiful property in WORTON.

Nestled in the charming WORTON subdivision, this delightful ranch-style home, built in 2020, offers a perfect blend of modern comfort and inviting warmth. With 1,144 square feet of thoughtfully designed living space, this residence is ideal for those seeking a cozy yet functional environment. Step inside to discover an open floor plan that seamlessly connects the kitchen, dining, and living areas, creating an inviting atmosphere for gatherings and everyday living. The spacious kitchen features a convenient island, perfect for casual meals or entertaining guests. Equipped with stainless steel appliances, including a built-in microwave, dishwasher, and washer/dryer, this kitchen is both stylish and practical. The breakfast area is a lovely spot to enjoy your morning coffee while basking in the natural light that fills the space. This home boasts three well-appointed bedrooms, including a primary suite with an en-suite bathroom that features a tub shower, providing a serene retreat at the end of the day. Ceiling fans throughout the home ensure comfort year-round, while the combination of living and dining spaces enhances the sense of togetherness. Outside, the property is equally inviting. The exterior is adorned with low-maintenance vinyl siding and features exterior lighting that adds a warm glow to the evenings. A spacious deck invites you to enjoy outdoor living, whether it's hosting summer barbecues or simply unwinding with a good book. The lot backs to trees, offering a peaceful backdrop and a sense of privacy that is hard to find. The 0.14-acre lot provides ample space for gardening or play, while a handy shed offers additional storage for tools and outdoor equipment. Parking is a breeze with a dedicated driveway, ensuring convenience for you and your guests. This home is not just a place to live; it's a sanctuary where comfort meets functionality. With its excellent condition and modern amenities, it's ready for you to make it your own. Don't miss the opportunity to experience the warmth and charm of this beautiful property in WORTON.

25213 Porters Grove Rd, Worton

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$675,000

Welcome home to historic Chestertown. This beautiful 5 bedroom colonial is located just one block from Washington College. Relax on your welcoming mahogany front porch before stepping inside this pristine home. Features a beautifully updated kitchen. Fresh exterior paint gleams. Iconic slate roof adds timeless appeal. Enjoy the private, fenced backyard oasis, meticulously landscaped for outdoor living. Complete with a 2-car garage.

5 Beds ⋅ 3 Baths

Welcome home to historic Chestertown. This beautiful 5 bedroom colonial is located just one block from Washington College. Relax on your welcoming mahogany front porch before stepping inside this pristine home. Features a beautifully updated kitchen. Fresh exterior paint gleams. Iconic slate roof adds timeless appeal. Enjoy the private, fenced backyard oasis, meticulously landscaped for outdoor living. Complete with a 2-car garage.

212 Washington Ave, Chestertown

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

$1,195,000

Remarkable downtown Chestertown development opportunity outside the Historic District. Incredible potential for a builder or a unique property for a private homesite. Directly adjacent to the Chestertown walking rail trail and just steps from downtown Chestertown while overlooking the Lawrence Wetland Preserve, rolling meadows and Radcliffe Creek behind. Sale includes two parcels - 302 S Mill (.45 acres) and 300 S Mill (.55 acres) - totaling approximately 1 acre. 300 is unimproved and 302 has a 1960s brick home on it. R:6 Traditional Neighborhood Development Zoning permits a wide range of dense residential development opportunities. Maximum residential density is limited to 42 bedrooms which could be single family homes, multi-family, apartments, townhouses, rowhouses, condos, and others. Smaller commercial options available as well. Public water and sewer is on site and additional allocations are available. Entire site is usable. Property is partially wooded with several large mature Oak Trees. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market. Additional information available upon request. Buyer to perform own due diligence. Do not enter property without and appointment.

2 Beds ⋅ 1 Baths

Remarkable downtown Chestertown development opportunity outside the Historic District. Incredible potential for a builder or a unique property for a private homesite. Directly adjacent to the Chestertown walking rail trail and just steps from downtown Chestertown while overlooking the Lawrence Wetland Preserve, rolling meadows and Radcliffe Creek behind. Sale includes two parcels - 302 S Mill (.45 acres) and 300 S Mill (.55 acres) - totaling approximately 1 acre. 300 is unimproved and 302 has a 1960s brick home on it. R:6 Traditional Neighborhood Development Zoning permits a wide range of dense residential development opportunities. Maximum residential density is limited to 42 bedrooms which could be single family homes, multi-family, apartments, townhouses, rowhouses, condos, and others. Smaller commercial options available as well. Public water and sewer is on site and additional allocations are available. Entire site is usable. Property is partially wooded with several large mature Oak Trees. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market. Additional information available upon request. Buyer to perform own due diligence. Do not enter property without and appointment.

302 S Mill St, Chestertown

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

$1,495,000

Discover the best of waterfront living in the sought-after community of Kinnairds Point. Set on 3.5 acres in a private, peaceful setting and thoughtfully designed for both everyday comfort and effortless entertaining, this home provides generous space for guests while maintaining inviting living areas that feel equally welcoming when it is just a few people, approximate square footage is close to 3,000. It is the best of both worlds: room to gather, comfortable spaces to unwind, and an exceptional waterfront setting. This home provides five bedrooms with an additional enclosed sleeping loft attached to one of the bedrooms, three and a half bathrooms, renovated kitchen and bathrooms, fireplace, a deck overlooking the water, easy access to a private dock with a boatlift, protected shoreline and the Bay is just around the corner. The outdoor spaces offer additional spots to take in the water views, watch the wildlife, entertain guests, or simply relax and enjoy the tranquility of Churn Creek. Mature trees, landscaping and hardscaping surround this waterfront oasis. In addition to your own private dock and waterfront, Kinnairds Point offers two waterfront community areas with a beach, pavilion, kayak rack and a boat ramp. Located just outside of Chestertown and within easy reach of points north and south.

5 Beds ⋅ 4 Baths

Discover the best of waterfront living in the sought-after community of Kinnairds Point. Set on 3.5 acres in a private, peaceful setting and thoughtfully designed for both everyday comfort and effortless entertaining, this home provides generous space for guests while maintaining inviting living areas that feel equally welcoming when it is just a few people, approximate square footage is close to 3,000. It is the best of both worlds: room to gather, comfortable spaces to unwind, and an exceptional waterfront setting. This home provides five bedrooms with an additional enclosed sleeping loft attached to one of the bedrooms, three and a half bathrooms, renovated kitchen and bathrooms, fireplace, a deck overlooking the water, easy access to a private dock with a boatlift, protected shoreline and the Bay is just around the corner. The outdoor spaces offer additional spots to take in the water views, watch the wildlife, entertain guests, or simply relax and enjoy the tranquility of Churn Creek. Mature trees, landscaping and hardscaping surround this waterfront oasis. In addition to your own private dock and waterfront, Kinnairds Point offers two waterfront community areas with a beach, pavilion, kayak rack and a boat ramp. Located just outside of Chestertown and within easy reach of points north and south.

23911 Kinnards Point Dr, Worton

Listing courtesy of Gunther-McClary Real Estate. Contact:

$359,000

Discover the charm of coastal living in the heart of the town of Rock Hall. just three blocks from the public beach! This beautifully maintained ranch-style home offers the perfect combination of comfort, style, and an exceptional location. Situated on a generous 0.34-acre lot, the property features beautifully landscaped grounds, cedar-impression vinyl siding, and a detached garage providing excellent storage and convenience. Step inside to find warm hardwood flooring and newer carpeting throughout the main living areas, creating an inviting and timeless atmosphere. The thoughtfully designed floor plan offers three spacious bedrooms and one-and-a-half bathrooms, providing comfortable living for full-time residents or an ideal weekend retreat. The outdoor living spaces truly set this home apart. Relax on the screened porch with your morning coffee, gather with friends on the patio, or enjoy al fresco dining surrounded by beautifully landscaped grounds. There is plenty of space to entertain, garden, or simply unwind and enjoy the relaxed pace of Rock Hall living. Located just minutes from local restaurants, marinas, shops, and the Chesapeake Bay, this property offers an incredible opportunity to enjoy all that this charming waterfront town has to offer. Whether you're looking for a full-time residence, vacation getaway, or weekend escape, this inviting Rock Hall home is ready to welcome you. Come experience the lifestyle and make this special property your own!

Discover the charm of coastal living in the heart of the town of Rock Hall. just three blocks from the public beach! This beautifully maintained ranch-style home offers the perfect combination of comfort, style, and an exceptional location. Situated on a generous 0.34-acre lot, the property features beautifully landscaped grounds, cedar-impression vinyl siding, and a detached garage providing excellent storage and convenience. Step inside to find warm hardwood flooring and newer carpeting throughout the main living areas, creating an inviting and timeless atmosphere. The thoughtfully designed floor plan offers three spacious bedrooms and one-and-a-half bathrooms, providing comfortable living for full-time residents or an ideal weekend retreat. The outdoor living spaces truly set this home apart. Relax on the screened porch with your morning coffee, gather with friends on the patio, or enjoy al fresco dining surrounded by beautifully landscaped grounds. There is plenty of space to entertain, garden, or simply unwind and enjoy the relaxed pace of Rock Hall living. Located just minutes from local restaurants, marinas, shops, and the Chesapeake Bay, this property offers an incredible opportunity to enjoy all that this charming waterfront town has to offer. Whether you're looking for a full-time residence, vacation getaway, or weekend escape, this inviting Rock Hall home is ready to welcome you. Come experience the lifestyle and make this special property your own!

5780 Kent Ave, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$649,000

Welcome to this beautifully crafted home in the water-oriented community of Great Oak Estates, just outside of Chestertown on Maryland’s Eastern Shore. Nestled in a peaceful setting that backs to woods alive with songbirds and butterflies, this high-quality residence offers an easy-flow floor plan designed for both lively gatherings and quiet private moments. A soaring two-story foyer greets guests and opens to the living room and family room, the latter featuring built-in cherry cabinets and a cozy propane fireplace. The formal dining room connects seamlessly to the kitchen and an additional casual dining space, making entertaining effortless. The kitchen showcases handmade cherry cabinetry and a brand-new refrigerator. Hardwood floors run throughout the main living areas, while brand-new carpeting softens every bedroom. On the main level, the primary suite includes its own bathroom, a walk-in closet, and plantation shutters. A second main-floor bedroom (ideal as a guest room or home office) shares convenient access to the hall bath. Completing the first floor are a large walk-in pantry and a laundry room outfitted with a brand-new washer and dryer. Upstairs you’ll find two additional spacious bedrooms, each with its own walk-in closet, plus a full bathroom. An oversized walk-in attic provides abundant storage or the perfect opportunity to create a bonus room or extra living space. Dual zone HVAC provides comfort from a newer lower level unit and an upper unit replaced in 2026. Complete roof replacement was completed in 2026 as well. A voluntary HOA opens the door to the amenities of Safe Harbor Great Oak Landing Marina—private beach area, pool, 9-hole golf course, and more. Simply walk or hop in a golf cart to reach the marina and enjoy all the water-oriented lifestyle this community has to offer. You’re also minutes from Rock Hall, with its additional marinas, charter boats, shopping, and restaurants. Less than 10 minutes away lies Chestertown and Washington College, along with more shopping, dining options, a hospital, and a wonderful Saturday morning Farmers Market, and much more. Whether you’re seeking a full-time residence or a relaxing Eastern Shore getaway, this home delivers quality craftsmanship, flexible living spaces, and convenient access to the best of Great Oak Estates and the surrounding area.

4 Beds ⋅ 3 Baths

Welcome to this beautifully crafted home in the water-oriented community of Great Oak Estates, just outside of Chestertown on Maryland’s Eastern Shore. Nestled in a peaceful setting that backs to woods alive with songbirds and butterflies, this high-quality residence offers an easy-flow floor plan designed for both lively gatherings and quiet private moments. A soaring two-story foyer greets guests and opens to the living room and family room, the latter featuring built-in cherry cabinets and a cozy propane fireplace. The formal dining room connects seamlessly to the kitchen and an additional casual dining space, making entertaining effortless. The kitchen showcases handmade cherry cabinetry and a brand-new refrigerator. Hardwood floors run throughout the main living areas, while brand-new carpeting softens every bedroom. On the main level, the primary suite includes its own bathroom, a walk-in closet, and plantation shutters. A second main-floor bedroom (ideal as a guest room or home office) shares convenient access to the hall bath. Completing the first floor are a large walk-in pantry and a laundry room outfitted with a brand-new washer and dryer. Upstairs you’ll find two additional spacious bedrooms, each with its own walk-in closet, plus a full bathroom. An oversized walk-in attic provides abundant storage or the perfect opportunity to create a bonus room or extra living space. Dual zone HVAC provides comfort from a newer lower level unit and an upper unit replaced in 2026. Complete roof replacement was completed in 2026 as well. A voluntary HOA opens the door to the amenities of Safe Harbor Great Oak Landing Marina—private beach area, pool, 9-hole golf course, and more. Simply walk or hop in a golf cart to reach the marina and enjoy all the water-oriented lifestyle this community has to offer. You’re also minutes from Rock Hall, with its additional marinas, charter boats, shopping, and restaurants. Less than 10 minutes away lies Chestertown and Washington College, along with more shopping, dining options, a hospital, and a wonderful Saturday morning Farmers Market, and much more. Whether you’re seeking a full-time residence or a relaxing Eastern Shore getaway, this home delivers quality craftsmanship, flexible living spaces, and convenient access to the best of Great Oak Estates and the surrounding area.

22400 Great Oak Landing Rd., Chestertown

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

$305,000

The house number is now 11037. Nestled among the farmland and waterways in Kent County is a cul-de-sac of new homes on Bottom Road just outside of Chestertown. The new 3 bedroom/2 bath single family home in a quiet, serene enclave is a perfect spot for your new home! This fresh and modern home offers glossy granite counters, SS appliances and a trendy color palette. The quality of this new construction shows in the engineered wood flooring and upgraded 5" baseboards and moldings. The primary bedroom is appointed with a walk-in closet and a shiny new full bath equipped with a double bowl sink/vanity. 2 additional bedrooms add options for an office or study. Enjoy the views of nature with your evening cocktail from the rear deck. Chestertown is a quaint, historic district on the Eastern Shore with an active art community and active boating society. The vast tributaries of the Chesapeake Bay and unspoiled land offer endless possibilities for hunting, fishing, kayaking, and canoeing. There is a front-foot fee of $15,000 that can be paid off with installments, annually over 15-20 years. The driveway of 10971 is an easement. The property line of 11037 goes beyond the driveway of 10971. See photos and site plan. PLEASE ENSURE ALL DOORS ARE LOCKED WHEN YOU LEAVE

The house number is now 11037. Nestled among the farmland and waterways in Kent County is a cul-de-sac of new homes on Bottom Road just outside of Chestertown. The new 3 bedroom/2 bath single family home in a quiet, serene enclave is a perfect spot for your new home! This fresh and modern home offers glossy granite counters, SS appliances and a trendy color palette. The quality of this new construction shows in the engineered wood flooring and upgraded 5" baseboards and moldings. The primary bedroom is appointed with a walk-in closet and a shiny new full bath equipped with a double bowl sink/vanity. 2 additional bedrooms add options for an office or study. Enjoy the views of nature with your evening cocktail from the rear deck. Chestertown is a quaint, historic district on the Eastern Shore with an active art community and active boating society. The vast tributaries of the Chesapeake Bay and unspoiled land offer endless possibilities for hunting, fishing, kayaking, and canoeing. There is a front-foot fee of $15,000 that can be paid off with installments, annually over 15-20 years. The driveway of 10971 is an easement. The property line of 11037 goes beyond the driveway of 10971. See photos and site plan. PLEASE ENSURE ALL DOORS ARE LOCKED WHEN YOU LEAVE

11037 Bottom Rd, Worton

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact: 4109724000

$559,500

There's a joyful feeling here that takes you straight back to childhood summers on the water. The Kinnairds Point community and property itself delivers this on just over two private acres at the end of a quiet cul-de-sac in Worton. Fully remodeled in 2020, the home opens into a vaulted great room with an exposed beam ceiling and a brick fireplace, flowing into a gorgeous, move-in-ready kitchen finished in crisp white cabinetry and a farmhouse sink. The owner's suite offers a spacious walk-in closet and an amazing renovated bath, while a screened porch and picnic lawn keep everyday living just as easy outdoors. The screened porch is designed for sharing beautiful moments and taking in nature. The full basement allows you to keep all of your "toys" tucked away while still keeping your cars in the garage. Best of all, Kinnairds Point offers access to two private Chesapeake waterfronts each with its own beach, pavilion, and kayak storage, one with a boat ramp just a walk or golf cart ride from your door. Crab pots, boat cruises, and sunset chairs are all in your future. Come life the Eastern Shore lifestyle in a polished setting just minutes from Historic Chestertown.

There's a joyful feeling here that takes you straight back to childhood summers on the water. The Kinnairds Point community and property itself delivers this on just over two private acres at the end of a quiet cul-de-sac in Worton. Fully remodeled in 2020, the home opens into a vaulted great room with an exposed beam ceiling and a brick fireplace, flowing into a gorgeous, move-in-ready kitchen finished in crisp white cabinetry and a farmhouse sink. The owner's suite offers a spacious walk-in closet and an amazing renovated bath, while a screened porch and picnic lawn keep everyday living just as easy outdoors. The screened porch is designed for sharing beautiful moments and taking in nature. The full basement allows you to keep all of your "toys" tucked away while still keeping your cars in the garage. Best of all, Kinnairds Point offers access to two private Chesapeake waterfronts each with its own beach, pavilion, and kayak storage, one with a boat ramp just a walk or golf cart ride from your door. Crab pots, boat cruises, and sunset chairs are all in your future. Come life the Eastern Shore lifestyle in a polished setting just minutes from Historic Chestertown.

12613 Walnut Valley Ct, Worton

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

$634,999

Welcome to 21191 West Sharp Street - conveniently located just a few steps from downtown Main Street and the Rock Hall Marinas, this 1920s craftsman has recently undergone a remarkable renovation from top to bottom. Taken down to the framing and expanding upon the existing square footage, it was completely rebuilt by a reputable local builder. No surface was left untouched! Several interior walls were removed for a new modern open-floor layout with elevated ceilings. The exceptional construction quality, a main floor primary suite and practical indoor / outdoor living spaces make this the perfect home for everyday living or a weekend retreat. A few of the outstanding features include: coffered ceilings, thick crown moldings and railings, dark hardwood floors, plantation shutters, double wine bar, a Wolf kitchen range, a conditioned two-car garage, screened-in porch, a copper water line, the list goes on. The home was also fitted with dual mini-split systems and a large Rinnai instant hot water heater: both energy efficient and budget friendly! As you enter you are greeted by a spacious living room and dining room combination which naturally flow into the modern kitchen. Finished with granite countertops, ceramic tile backsplash, and Wolf and GE appliances, The first floor primary bedroom with large ensuite bath enables one to enjoy all one floor living should they desire. A double chilled wine bar and powder room behind the kitchen complete the first floor living area. Moving upstairs, there is a generously sized living space in the front and two full bedrooms behind in the newly added dormers. A new full bath with ceramic tile flooring and shower, and stone vanity further complements the upstairs living space. Moving to the back of the house; the screened-in porch is perfect for summertime crabs feasts and the propane fire pit is great for summer evenings with friends and family. Plenty of parking in the back driveway or in the two-car garage which is heated, air conditioned and spray-foam insulated. A quick walk to Java Rock for a morning coffee or an easy stroll to the Marina’s or the beach. Rock Hall is a vibrant town with many great restaurants, a brewery, and many festivals like Pirates and Wenches and Fall Fest. You dont want to miss this remarkable home.

Welcome to 21191 West Sharp Street - conveniently located just a few steps from downtown Main Street and the Rock Hall Marinas, this 1920s craftsman has recently undergone a remarkable renovation from top to bottom. Taken down to the framing and expanding upon the existing square footage, it was completely rebuilt by a reputable local builder. No surface was left untouched! Several interior walls were removed for a new modern open-floor layout with elevated ceilings. The exceptional construction quality, a main floor primary suite and practical indoor / outdoor living spaces make this the perfect home for everyday living or a weekend retreat. A few of the outstanding features include: coffered ceilings, thick crown moldings and railings, dark hardwood floors, plantation shutters, double wine bar, a Wolf kitchen range, a conditioned two-car garage, screened-in porch, a copper water line, the list goes on. The home was also fitted with dual mini-split systems and a large Rinnai instant hot water heater: both energy efficient and budget friendly! As you enter you are greeted by a spacious living room and dining room combination which naturally flow into the modern kitchen. Finished with granite countertops, ceramic tile backsplash, and Wolf and GE appliances, The first floor primary bedroom with large ensuite bath enables one to enjoy all one floor living should they desire. A double chilled wine bar and powder room behind the kitchen complete the first floor living area. Moving upstairs, there is a generously sized living space in the front and two full bedrooms behind in the newly added dormers. A new full bath with ceramic tile flooring and shower, and stone vanity further complements the upstairs living space. Moving to the back of the house; the screened-in porch is perfect for summertime crabs feasts and the propane fire pit is great for summer evenings with friends and family. Plenty of parking in the back driveway or in the two-car garage which is heated, air conditioned and spray-foam insulated. A quick walk to Java Rock for a morning coffee or an easy stroll to the Marina’s or the beach. Rock Hall is a vibrant town with many great restaurants, a brewery, and many festivals like Pirates and Wenches and Fall Fest. You dont want to miss this remarkable home.

21191 W Sharp St, Rock Hall

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

$304,000

Affordable, adorable, and move-in ready! This charming home offers everything you need with a great open floor plan designed for comfortable living. The private primary suite features its own bathroom and is thoughtfully separated from the two additional bedrooms for added privacy. The laundry room is conveniently located just off the kitchen and includes a separate exterior entrance. Step outside and enjoy the fully fenced backyard, complete with a storage shed, cozy patio area, and fire pit area, making it perfect for relaxing or entertaining. Dont wait to see this one!

Affordable, adorable, and move-in ready! This charming home offers everything you need with a great open floor plan designed for comfortable living. The private primary suite features its own bathroom and is thoughtfully separated from the two additional bedrooms for added privacy. The laundry room is conveniently located just off the kitchen and includes a separate exterior entrance. Step outside and enjoy the fully fenced backyard, complete with a storage shed, cozy patio area, and fire pit area, making it perfect for relaxing or entertaining. Dont wait to see this one!

7464 Shortall St, Chestertown

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

$349,900

Brand new construction in Chesapeake Landing, and the primary suite is on the main level — full bath, walk-in closet, no stairs at the end of the day. That one detail is what most buyers spend months searching for and rarely find at this price. Roughly 1,600 square feet, laid out so the main floor handles everything: an open living room, a kitchen with shaker cabinets, granite counters and stainless steel appliances, plus laundry and a half bath. Luxury vinyl plank runs throughout — the kind of floor that still looks right after wet boat shoes and muddy paws. Upstairs, two additional bedrooms share a full bath. Guests, an office, a hobby room — tucked away from the main living space so the first floor stays yours. The lot is a third of an acre with a private driveway, giving you real yard on all sides rather than a strip of grass between neighbors. Chesapeake Landing is a waterfront community with a clubhouse, walking trails and community water access. Membership in the community association is voluntary and carries a modest annual fee. Historic Chestertown — the shops, the restaurants, the riverfront — is a short drive away. Everything here is new. New systems, new surfaces, new appliances. Nothing deferred, nothing to renovate, nothing waiting to break in year two. Schedule your private tour today.

Brand new construction in Chesapeake Landing, and the primary suite is on the main level — full bath, walk-in closet, no stairs at the end of the day. That one detail is what most buyers spend months searching for and rarely find at this price. Roughly 1,600 square feet, laid out so the main floor handles everything: an open living room, a kitchen with shaker cabinets, granite counters and stainless steel appliances, plus laundry and a half bath. Luxury vinyl plank runs throughout — the kind of floor that still looks right after wet boat shoes and muddy paws. Upstairs, two additional bedrooms share a full bath. Guests, an office, a hobby room — tucked away from the main living space so the first floor stays yours. The lot is a third of an acre with a private driveway, giving you real yard on all sides rather than a strip of grass between neighbors. Chesapeake Landing is a waterfront community with a clubhouse, walking trails and community water access. Membership in the community association is voluntary and carries a modest annual fee. Historic Chestertown — the shops, the restaurants, the riverfront — is a short drive away. Everything here is new. New systems, new surfaces, new appliances. Nothing deferred, nothing to renovate, nothing waiting to break in year two. Schedule your private tour today.

23208 Buck Neck Rd, Chestertown

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442

$524,900

Welcome home to this beautifully maintained and thoughtfully updated residence nestled at the end of a peaceful cul-de-sac! Originally built in 2002 and extensively renovated in 2020, this home offers the perfect combination of timeless design, modern updates, and comfortable living. Hickory flooring flows throughout the main living areas and bedrooms, while LVP flooring provides durability and easy maintenance in all bathrooms and the laundry room. The heart of the home is the impressive gourmet kitchen, featuring quartz countertops, a granite-topped island, 5-burner propane range, double wall ovens, built-in microwave, pot filler, farmhouse sink, beautiful backsplash, and abundant cabinetry for exceptional storage. Open to the spacious great room, the kitchen creates an inviting gathering space highlighted by a propane fireplace with a beautiful mantel. The living room features Anderson sliding glass doors that open to the deck, creating an easy connection between indoor and outdoor living. The spacious primary suite is a true retreat, featuring Anderson sliding glass doors leading directly to the deck, a walk-in closet, and an updated primary bath with double vanity and a large tiled shower enclosed by glass doors. The third bedroom offers clever versatility with a Murphy bed that maximizes the space while providing a comfortable guest room when needed. Step outside to enjoy the deck and partially fenced backyard, complete with a storage shed and peaceful views of the open common area behind the property. An attached two-car garage and paved driveway add convenience and functionality. Meticulously maintained and beautifully updated, this home offers a wonderful opportunity to enjoy turnkey living in a highly desirable Chestertown location, close to the town's shops, restaurants, waterfront, and amenities. Don't miss the opportunity to make this exceptional home your own!

Welcome home to this beautifully maintained and thoughtfully updated residence nestled at the end of a peaceful cul-de-sac! Originally built in 2002 and extensively renovated in 2020, this home offers the perfect combination of timeless design, modern updates, and comfortable living. Hickory flooring flows throughout the main living areas and bedrooms, while LVP flooring provides durability and easy maintenance in all bathrooms and the laundry room. The heart of the home is the impressive gourmet kitchen, featuring quartz countertops, a granite-topped island, 5-burner propane range, double wall ovens, built-in microwave, pot filler, farmhouse sink, beautiful backsplash, and abundant cabinetry for exceptional storage. Open to the spacious great room, the kitchen creates an inviting gathering space highlighted by a propane fireplace with a beautiful mantel. The living room features Anderson sliding glass doors that open to the deck, creating an easy connection between indoor and outdoor living. The spacious primary suite is a true retreat, featuring Anderson sliding glass doors leading directly to the deck, a walk-in closet, and an updated primary bath with double vanity and a large tiled shower enclosed by glass doors. The third bedroom offers clever versatility with a Murphy bed that maximizes the space while providing a comfortable guest room when needed. Step outside to enjoy the deck and partially fenced backyard, complete with a storage shed and peaceful views of the open common area behind the property. An attached two-car garage and paved driveway add convenience and functionality. Meticulously maintained and beautifully updated, this home offers a wonderful opportunity to enjoy turnkey living in a highly desirable Chestertown location, close to the town's shops, restaurants, waterfront, and amenities. Don't miss the opportunity to make this exceptional home your own!

1003 Twin Ct, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453

$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:

$487,000

Seller is super motivated and may have found their next home so this must go! All offers welcomed! Home recently appraised for $501,000. Welcome to 16 Howell Point Road in Betterton, Maryland, where small-town Eastern Shore charm meets comfortable living just a few blocks from beautiful Betterton Beach! This inviting 3-bedroom, 3-bath home offers plenty of space inside and out. The full walk-out basement is partially finished, providing additional living space with endless possibilities for a family room, home office, recreation area, guest space, or workshop. Step outside onto the back deck overlooking the fenced-in backyard, perfect for pets, entertaining, gardening, or simply relaxing at the end of the day. The large driveway provides plenty of parking, while the spacious backyard offers room to enjoy the outdoors. One of the home’s best features comes each evening—gorgeous sunsets stretching across the rolling hills and surrounding farmland, creating a peaceful Eastern Shore backdrop right from your own backyard. Located just blocks from Betterton Beach and the Chesapeake Bay, you’ll have easy access to swimming, boating, fishing, kayaking, and everything that makes this waterfront community such a special place to call home. Whether you’re searching for a full-time residence, weekend getaway, or Eastern Shore retreat, 16 Howell Point Road is ready to welcome you home!

Seller is super motivated and may have found their next home so this must go! All offers welcomed! Home recently appraised for $501,000. Welcome to 16 Howell Point Road in Betterton, Maryland, where small-town Eastern Shore charm meets comfortable living just a few blocks from beautiful Betterton Beach! This inviting 3-bedroom, 3-bath home offers plenty of space inside and out. The full walk-out basement is partially finished, providing additional living space with endless possibilities for a family room, home office, recreation area, guest space, or workshop. Step outside onto the back deck overlooking the fenced-in backyard, perfect for pets, entertaining, gardening, or simply relaxing at the end of the day. The large driveway provides plenty of parking, while the spacious backyard offers room to enjoy the outdoors. One of the home’s best features comes each evening—gorgeous sunsets stretching across the rolling hills and surrounding farmland, creating a peaceful Eastern Shore backdrop right from your own backyard. Located just blocks from Betterton Beach and the Chesapeake Bay, you’ll have easy access to swimming, boating, fishing, kayaking, and everything that makes this waterfront community such a special place to call home. Whether you’re searching for a full-time residence, weekend getaway, or Eastern Shore retreat, 16 Howell Point Road is ready to welcome you home!

16 Howell Point Rd, Betterton

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

$329,900

Situated on .97± acres in Worton, this versatile property offers plenty of space and possibilities with two utility buildings, public water, and public sewer. The main home features an open floor plan highlighted by a custom wooden kitchen bar that provides generous counter space and creates a natural gathering spot for entertaining. A separate shop building adds even more functionality and is equipped with an oil furnace and air conditioning, making it comfortable for year-round use. Whether you’re looking for workshop space, storage, a hobby area, or room for your next project, this property offers flexibility that's hard to find. Conveniently located in Worton with nearly an acre of land, public utilities, and multiple buildings, this property is ready for its next owner to make it their own.

2 Beds ⋅ 2 Baths

Situated on .97± acres in Worton, this versatile property offers plenty of space and possibilities with two utility buildings, public water, and public sewer. The main home features an open floor plan highlighted by a custom wooden kitchen bar that provides generous counter space and creates a natural gathering spot for entertaining. A separate shop building adds even more functionality and is equipped with an oil furnace and air conditioning, making it comfortable for year-round use. Whether you’re looking for workshop space, storage, a hobby area, or room for your next project, this property offers flexibility that's hard to find. Conveniently located in Worton with nearly an acre of land, public utilities, and multiple buildings, this property is ready for its next owner to make it their own.

10725 Worton Rd, Worton

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956

$263,000

Welcome to 115 Chester Arms in Chestertown, MD! This 3-bedroom, 2-bath home offers a comfortable and functional layout with plenty of potential to make it your own. The home provides a nice combination of living space, comfortable bedrooms, and the convenience of two full bathrooms. Whether you're a first-time buyer, looking to downsize, or simply searching for a home in the Chestertown area, this property is worth a look. Conveniently located near downtown Chestertown, local shopping, dining, and everyday amenities.