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Located in the College Heights neighborhood of Chestertown, this 3-bedroom, 2-bath home is situated on a .34± acre lot and is full of potential! Enjoy the convenience of stepping right out your back door to the dog park, all while being within walking distance of downtown Chestertown’s shops, restaurants, and waterfront. With a little TLC and your personal touch, this property is a great opportunity to make a home your own in a fantastic location!

3 Beds ⋅ 2 Baths

Located in the College Heights neighborhood of Chestertown, this 3-bedroom, 2-bath home is situated on a .34± acre lot and is full of potential! Enjoy the convenience of stepping right out your back door to the dog park, all while being within walking distance of downtown Chestertown’s shops, restaurants, and waterfront. With a little TLC and your personal touch, this property is a great opportunity to make a home your own in a fantastic location!

317 Rolling Rd, Chestertown

Listing courtesy of Select Land & Homes, LLC. Contact:

$175,000

Needs work. Sold as is

3 Beds ⋅ 1 Baths

Needs work. Sold as is

7545 Quaker Neck Rd, Chestertown

Listing courtesy of Thurston Wyatt Real Estate, LLC. Contact:

$365,000

Enjoy the charm of country living in this 3-bedroom, 2-bath rancher situated on just over an acre in Massey! Offering convenient one-level living, this home has a rustic, cozy feel with vaulted ceilings, distinctive Scotch Pine wood from Finland in the living room, and a pellet stove that creates a warm and inviting atmosphere. Step outside to enjoy the deck and above-ground pool, perfect for relaxing and making the most of your outdoor space. One of the property's standout features is the impressive 24' x 32' insulated pole building/shop, complete with 100-amp electric, a car lift, and built-in office space—ideal for automotive enthusiasts, hobbyists, contractors, or anyone needing extra workspace and storage. The 75-inch TV in the shop and car lift convey with the sale. Additional peace of mind comes from the fully encapsulated crawlspace with a dehumidifier. The living room couches also convey. With room to enjoy the outdoors, a functional workshop, and the convenience of one-level living, this property offers plenty of possibilities. Home also has Starlink for Internet and equipment stays with property/Talkie is also available. Well pump and pressure tank replaced September, 2026. Property is being sold strictly AS IS. Shared driveway and existing right-of-way access for the farm.

3 Beds ⋅ 2 Baths

Enjoy the charm of country living in this 3-bedroom, 2-bath rancher situated on just over an acre in Massey! Offering convenient one-level living, this home has a rustic, cozy feel with vaulted ceilings, distinctive Scotch Pine wood from Finland in the living room, and a pellet stove that creates a warm and inviting atmosphere. Step outside to enjoy the deck and above-ground pool, perfect for relaxing and making the most of your outdoor space. One of the property's standout features is the impressive 24' x 32' insulated pole building/shop, complete with 100-amp electric, a car lift, and built-in office space—ideal for automotive enthusiasts, hobbyists, contractors, or anyone needing extra workspace and storage. The 75-inch TV in the shop and car lift convey with the sale. Additional peace of mind comes from the fully encapsulated crawlspace with a dehumidifier. The living room couches also convey. With room to enjoy the outdoors, a functional workshop, and the convenience of one-level living, this property offers plenty of possibilities. Home also has Starlink for Internet and equipment stays with property/Talkie is also available. Well pump and pressure tank replaced September, 2026. Property is being sold strictly AS IS. Shared driveway and existing right-of-way access for the farm.

12035 Galena Rd, Massey

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

$349,900

Investor Alert in Historic Downtown Chestertown! Fully Occupied Triplex. Units offer hardwood floors, mini splits to units 1 and 2, a new bathroom in unit 3 and kitchen upgrades n unit 2 including new counter tops and flooring

501 High St, Chestertown

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

$349,900

Brand new construction in water oriented Tolchester Estates located on the Chesapeake Bay. 4 Bedroom, 2 bath Cape Cod on a wooded lot and quiet neighborhood. Community offer private beach and boat ramp access. Rear private deck.

4 Beds ⋅ 2 Baths

Brand new construction in water oriented Tolchester Estates located on the Chesapeake Bay. 4 Bedroom, 2 bath Cape Cod on a wooded lot and quiet neighborhood. Community offer private beach and boat ramp access. Rear private deck.

8668 Elm Rd, Chestertown

Listing courtesy of Kevin Dey Realty. Contact:

$519,900

Enjoy a peaceful country setting at 7655 James Lane. Situated on a two-acre lot along a quiet cul-de-sac street, this well-maintained ranch home offers approximately 2,475 square feet of living space, three bedrooms, and two-and-a-half bathrooms, complemented by mature landscaping and a scenic farmland backdrop. A cozy front porch welcomes you inside to a spacious layout featuring separate living and family rooms, a formal dining area, and an eat-in country-style kitchen with rich wood cabinetry and stainless steel appliances. Flowing through the main living area are hardwood floors leading to a large and bright sunroom. The sunroom, complete with skylights offers an inviting space to relax and enjoy the surroundings, with a dedicated mini-split providing heating and cooling for year-round comfort. Just off the sunroom, a deck extends the living space outdoors, while a fenced portion of the yard offers additional flexibility for outdoor enjoyment. The attached two-car garage provides convenient parking and storage. A standout feature of this property is the large pole building, measuring approximately 40' by 22', with a heated shop and two tall doors—one at the front and another on the side—for RV or boat storage. This versatile building offers valuable space for projects, equipment, and recreational vehicles, along with a mezzanine storage loft above the shop. The rear of the building provides additional unfinished storage space with separate access. Located approximately 10 minutes from Chestertown, Rock Hall, and the public boat launch at Broadneck Landing, this property pairs a peaceful rural setting with convenient access to nearby shops, dining, and boating. Schedule your tour today!

3 Beds ⋅ 3 Baths

Enjoy a peaceful country setting at 7655 James Lane. Situated on a two-acre lot along a quiet cul-de-sac street, this well-maintained ranch home offers approximately 2,475 square feet of living space, three bedrooms, and two-and-a-half bathrooms, complemented by mature landscaping and a scenic farmland backdrop. A cozy front porch welcomes you inside to a spacious layout featuring separate living and family rooms, a formal dining area, and an eat-in country-style kitchen with rich wood cabinetry and stainless steel appliances. Flowing through the main living area are hardwood floors leading to a large and bright sunroom. The sunroom, complete with skylights offers an inviting space to relax and enjoy the surroundings, with a dedicated mini-split providing heating and cooling for year-round comfort. Just off the sunroom, a deck extends the living space outdoors, while a fenced portion of the yard offers additional flexibility for outdoor enjoyment. The attached two-car garage provides convenient parking and storage. A standout feature of this property is the large pole building, measuring approximately 40' by 22', with a heated shop and two tall doors—one at the front and another on the side—for RV or boat storage. This versatile building offers valuable space for projects, equipment, and recreational vehicles, along with a mezzanine storage loft above the shop. The rear of the building provides additional unfinished storage space with separate access. Located approximately 10 minutes from Chestertown, Rock Hall, and the public boat launch at Broadneck Landing, this property pairs a peaceful rural setting with convenient access to nearby shops, dining, and boating. Schedule your tour today!

7655 James Ln, Chestertown

Listing courtesy of RE/MAX Advantage Realty. Contact:

$249,000

Updated Home on .63 Acres with Village Zoning! Don’t let the one bedroom fool you! This charming, well-maintained home offers more than meets the eye, with numerous updates, a full, unfinished walk-out basement, and plenty of possibilities! Situated on .63 acres with Village zoning and NO HOA, this property offers the freedom and flexibility you’ve been looking for! Bring your boat, RV, or recreational toys—there’s room to enjoy your property your way! Inside, you’ll appreciate the many improvements, including an updated roof, windows, water heater, water softener, and luxury vinyl plank (LVP) flooring. Step outside onto the beautiful Trex deck with low-maintenance vinyl railings, perfect for relaxing or entertaining. The full unfinished walk-out basement offers excellent storage and potential for additional living space. Conveniently located just minutes from Chestertown, Betterton, and Still Pond, you’ll enjoy peaceful country living while remaining close to shopping, dining, boating, beaches, and everything Kent County has to offer! Whether you’re searching for your first home, looking to downsize, or wanting a weekend getaway, this one deserves a look! Affordable living and valuable updates-all on your own .63-acre property!

1 Beds ⋅ 1 Baths

Updated Home on .63 Acres with Village Zoning! Don’t let the one bedroom fool you! This charming, well-maintained home offers more than meets the eye, with numerous updates, a full, unfinished walk-out basement, and plenty of possibilities! Situated on .63 acres with Village zoning and NO HOA, this property offers the freedom and flexibility you’ve been looking for! Bring your boat, RV, or recreational toys—there’s room to enjoy your property your way! Inside, you’ll appreciate the many improvements, including an updated roof, windows, water heater, water softener, and luxury vinyl plank (LVP) flooring. Step outside onto the beautiful Trex deck with low-maintenance vinyl railings, perfect for relaxing or entertaining. The full unfinished walk-out basement offers excellent storage and potential for additional living space. Conveniently located just minutes from Chestertown, Betterton, and Still Pond, you’ll enjoy peaceful country living while remaining close to shopping, dining, boating, beaches, and everything Kent County has to offer! Whether you’re searching for your first home, looking to downsize, or wanting a weekend getaway, this one deserves a look! Affordable living and valuable updates-all on your own .63-acre property!

25705 Meadow Rd, Worton

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

$719,500

A Private Waterfront Retreat off Maryland’s Sassafras!!! Welcome to your own waterfront retreat and nature sanctuary, a private one-acre property designed around the water, the outdoors and the beauty of its natural setting. With more than 300 feet of waterfront and a 70-foot private dock, this unique property offers exceptional access for boating, kayaking and paddleboarding, via Swantown to the serene Sassafras River and nearby Georgetown Marina. From the moment you arrive along the tree-lined drive, the home feels tucked into its surroundings. An inviting front porch, thoughtfully designed landscaping and extensive hardscaping complement the wooded setting. Multiple outdoor living spaces take full advantage and provide abundant water views. Three levels of rear porches and decks provide sweeping views across the waterfront, creating wonderful spaces for morning coffee, outdoor dining, entertaining or simply enjoying the changing seasons. Inside, the 2,240-square-foot home offers three bedrooms and 2.5 baths, with the water and shoreline remaining the focal point. Full glass doors from the primary bedroom, living room and kitchen bring the landscape into the home and provide abundant views toward the waterfront. The modern, spacious living area boasts crown molding, hardwood flooring and built-ins, which flank the wood burning fireplace. The adjacent spacious kitchen with a large center island designed for gathering and dining, features quartz countertops, stainless appliances including a double oven, under cabinet lighting and a chef-inspired pantry for storage. The second level is home to a primary en-suite with a walk-in closet and full bathroom and connected deck that is perfect spot to enjoy morning coffee and birds, where hummingbirds and eagles regularly visit. Two additional bedrooms and a full updated hall bathroom complete this level. A meticulously maintained one-car garage offers additional storage, work area and additional refrigerator and freezer opportunity. The outside is a nature lover's paradise. The lower deck and waterfront flagstone patio add additional outdoor living space. Just to the right of the home is a private path to your very own private dock - the perfect spot to launch your kayaks, canoes or paddle boards. Enjoy this beautiful property with amazing landscaping and water views; the perfect location for privacy and peacefulness, and a great place to entertain as well. With easy access to Route 301, you are just a short drive to Middletown and Wilmington. Make this stunning home yours - schedule a tour today!

3 Beds ⋅ 3 Baths

A Private Waterfront Retreat off Maryland’s Sassafras!!! Welcome to your own waterfront retreat and nature sanctuary, a private one-acre property designed around the water, the outdoors and the beauty of its natural setting. With more than 300 feet of waterfront and a 70-foot private dock, this unique property offers exceptional access for boating, kayaking and paddleboarding, via Swantown to the serene Sassafras River and nearby Georgetown Marina. From the moment you arrive along the tree-lined drive, the home feels tucked into its surroundings. An inviting front porch, thoughtfully designed landscaping and extensive hardscaping complement the wooded setting. Multiple outdoor living spaces take full advantage and provide abundant water views. Three levels of rear porches and decks provide sweeping views across the waterfront, creating wonderful spaces for morning coffee, outdoor dining, entertaining or simply enjoying the changing seasons. Inside, the 2,240-square-foot home offers three bedrooms and 2.5 baths, with the water and shoreline remaining the focal point. Full glass doors from the primary bedroom, living room and kitchen bring the landscape into the home and provide abundant views toward the waterfront. The modern, spacious living area boasts crown molding, hardwood flooring and built-ins, which flank the wood burning fireplace. The adjacent spacious kitchen with a large center island designed for gathering and dining, features quartz countertops, stainless appliances including a double oven, under cabinet lighting and a chef-inspired pantry for storage. The second level is home to a primary en-suite with a walk-in closet and full bathroom and connected deck that is perfect spot to enjoy morning coffee and birds, where hummingbirds and eagles regularly visit. Two additional bedrooms and a full updated hall bathroom complete this level. A meticulously maintained one-car garage offers additional storage, work area and additional refrigerator and freezer opportunity. The outside is a nature lover's paradise. The lower deck and waterfront flagstone patio add additional outdoor living space. Just to the right of the home is a private path to your very own private dock - the perfect spot to launch your kayaks, canoes or paddle boards. Enjoy this beautiful property with amazing landscaping and water views; the perfect location for privacy and peacefulness, and a great place to entertain as well. With easy access to Route 301, you are just a short drive to Middletown and Wilmington. Make this stunning home yours - schedule a tour today!

13852 Sassafras Rd, Galena

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$330,000

Nestled in the serene enclave of Watermans Estates, this exquisite end-of-row townhouse offers a harmonious blend of contemporary design and luxurious living. Spanning 1,628 square feet, this home is a sanctuary of comfort and style, perfect for those seeking an elevated lifestyle. Step inside to discover an inviting open floor plan that seamlessly connects the living and dining areas, enhanced by plush carpeting and a cozy gas fireplace that beckons for intimate gatherings. The kitchen is a culinary enthusiast's dream, featuring upgraded countertops, a built-in microwave, and a gas range, all designed to inspire your inner chef. Enjoy casual meals in the kitchen's table space or host dinners in the dedicated dining area. This residence boasts three spacious bedrooms, including a convenient entry-level bedroom, ensuring comfort and privacy for all. Each of the three bathrooms is thoughtfully designed, with the master bath featuring a luxurious soaking tub, perfect for unwinding after a long day. The allure of this home extends beyond its interior. Step outside onto the expansive deck or balcony, where you can savor morning coffee or evening sunsets amidst the tranquil sounds of nature. The partly wooded lot, adorned with mature trees, offers a peaceful retreat. Located just three blocks from the stunning Chesapeake Bay, this property invites you to embrace a lifestyle enriched by water-oriented activities. Whether it's a leisurely stroll along the shore or a day of boating, the beauty of the bay is always within reach. Parking is a breeze with a private driveway and an attached garage, ensuring convenience for you and your guests. The home is equipped with modern amenities, including a washer and dryer, ensuring that daily tasks are handled with ease. This property is not just a house; it's a place to create lasting memories. With its blend of luxury, comfort, and natural beauty, this townhouse in Watermans Estates is a rare find, offering an exclusive lifestyle that truly feels like home. Looking for a cash flowing investment? The property has performed exceptionally well as a short-term rental. With no restrictions, this property could be the perfect option. Experience the perfect balance of elegance and tranquility-your dream home awaits.

3 Beds ⋅ 3 Baths

Nestled in the serene enclave of Watermans Estates, this exquisite end-of-row townhouse offers a harmonious blend of contemporary design and luxurious living. Spanning 1,628 square feet, this home is a sanctuary of comfort and style, perfect for those seeking an elevated lifestyle. Step inside to discover an inviting open floor plan that seamlessly connects the living and dining areas, enhanced by plush carpeting and a cozy gas fireplace that beckons for intimate gatherings. The kitchen is a culinary enthusiast's dream, featuring upgraded countertops, a built-in microwave, and a gas range, all designed to inspire your inner chef. Enjoy casual meals in the kitchen's table space or host dinners in the dedicated dining area. This residence boasts three spacious bedrooms, including a convenient entry-level bedroom, ensuring comfort and privacy for all. Each of the three bathrooms is thoughtfully designed, with the master bath featuring a luxurious soaking tub, perfect for unwinding after a long day. The allure of this home extends beyond its interior. Step outside onto the expansive deck or balcony, where you can savor morning coffee or evening sunsets amidst the tranquil sounds of nature. The partly wooded lot, adorned with mature trees, offers a peaceful retreat. Located just three blocks from the stunning Chesapeake Bay, this property invites you to embrace a lifestyle enriched by water-oriented activities. Whether it's a leisurely stroll along the shore or a day of boating, the beauty of the bay is always within reach. Parking is a breeze with a private driveway and an attached garage, ensuring convenience for you and your guests. The home is equipped with modern amenities, including a washer and dryer, ensuring that daily tasks are handled with ease. This property is not just a house; it's a place to create lasting memories. With its blend of luxury, comfort, and natural beauty, this townhouse in Watermans Estates is a rare find, offering an exclusive lifestyle that truly feels like home. Looking for a cash flowing investment? The property has performed exceptionally well as a short-term rental. With no restrictions, this property could be the perfect option. Experience the perfect balance of elegance and tranquility-your dream home awaits.

21121 Striper Run, Rock Hall

Listing courtesy of Astoria Realty Advisors LLC. Contact:

$689,000

Nestled in the serene Georgetown subdivision, this exquisite contemporary residence offers a harmonious blend of luxury and comfort, set on a sprawling 4.76-acre lot that invites tranquility and privacy. Built in 2005, this meticulously maintained home boasts 2,748 square feet of thoughtfully designed living space, perfect for those who appreciate both style and functionality. The upgraded countertops and stainless steel appliances in the kitchen elevate the culinary experience, while the formal dining room, adorned with crown moldings and exposed beams, adds a touch of sophistication. Natural light floods the interior through casement windows, enhancing the warmth of the hardwood floors that flow throughout the home. The main level features a convenient entry-level bedroom, perfect for guests or as the primary bedroom. The luxurious bathrooms include a walk-in shower and claw foot soaking tub providing a spa-like retreat at home. For those who appreciate the finer details, the home is equipped with recessed lighting, ceiling fans, and a dedicated wine storage area, ensuring every aspect of your lifestyle is catered to. The laundry room, conveniently located on the main floor, adds to the home's practicality. Outside, the property is beautifully landscaped with a mix of cleared and partly wooded areas, offering a picturesque view of the surrounding trees and woods. The expansive deck provides an ideal space for outdoor entertaining or simply enjoying the peaceful surroundings. With ample parking options, including a paved driveway and a detached garage with space for two vehicles, convenience is at your fingertips. This residence is not just a home; it's a lifestyle. Enjoy the luxury of space, the beauty of nature, and the comfort of a well-appointed interior. Experience the perfect blend of elegance and warmth in this Georgetown gem, where every detail has been thoughtfully curated for your enjoyment.

3 Beds ⋅ 2 Baths

Nestled in the serene Georgetown subdivision, this exquisite contemporary residence offers a harmonious blend of luxury and comfort, set on a sprawling 4.76-acre lot that invites tranquility and privacy. Built in 2005, this meticulously maintained home boasts 2,748 square feet of thoughtfully designed living space, perfect for those who appreciate both style and functionality. The upgraded countertops and stainless steel appliances in the kitchen elevate the culinary experience, while the formal dining room, adorned with crown moldings and exposed beams, adds a touch of sophistication. Natural light floods the interior through casement windows, enhancing the warmth of the hardwood floors that flow throughout the home. The main level features a convenient entry-level bedroom, perfect for guests or as the primary bedroom. The luxurious bathrooms include a walk-in shower and claw foot soaking tub providing a spa-like retreat at home. For those who appreciate the finer details, the home is equipped with recessed lighting, ceiling fans, and a dedicated wine storage area, ensuring every aspect of your lifestyle is catered to. The laundry room, conveniently located on the main floor, adds to the home's practicality. Outside, the property is beautifully landscaped with a mix of cleared and partly wooded areas, offering a picturesque view of the surrounding trees and woods. The expansive deck provides an ideal space for outdoor entertaining or simply enjoying the peaceful surroundings. With ample parking options, including a paved driveway and a detached garage with space for two vehicles, convenience is at your fingertips. This residence is not just a home; it's a lifestyle. Enjoy the luxury of space, the beauty of nature, and the comfort of a well-appointed interior. Experience the perfect blend of elegance and warmth in this Georgetown gem, where every detail has been thoughtfully curated for your enjoyment.

13950 Huyett Ln, Galena

Listing courtesy of RE/MAX Associates - Newark. Contact:

$299,999

Selller has made a Major price reduction to move this propperty! Welcome to this beautifully renovated 4-bedroom, 2-bath Cape Cod located in the heart of Rock Hall, MD! Completely updated from top to bottom, this home features a brand-new roof, HVAC system, water heater, flooring, paint, upgraded bathrooms, interior doors, and stylish recessed lighting as well as ceiling fans throughout. Enjoy mornings and evenings on the charming screened-in front porch, perfect for relaxing or entertaining. Inside, the home offers a bright and open layout with modern finishes while still retaining that classic Cape Cod charm. Sitting on a large lot, there’s plenty of space for outdoor activities, gardening, boat storage or future expansion. The is ample parking in the driveway as well as two-way access. Ideally situated in the sought-after waterfront town of Rock Hall, you’ll be just minutes from multiple boat ramps, marinas, and a short walk to restaurants, local shops, and the center of town. Whether you're looking for a full-time residence or a weekend getaway, this turn-key home delivers the best of Eastern Shore living. Move-in ready and loaded with upgrades—don’t miss this opportunity!

4 Beds ⋅ 2 Baths

Selller has made a Major price reduction to move this propperty! Welcome to this beautifully renovated 4-bedroom, 2-bath Cape Cod located in the heart of Rock Hall, MD! Completely updated from top to bottom, this home features a brand-new roof, HVAC system, water heater, flooring, paint, upgraded bathrooms, interior doors, and stylish recessed lighting as well as ceiling fans throughout. Enjoy mornings and evenings on the charming screened-in front porch, perfect for relaxing or entertaining. Inside, the home offers a bright and open layout with modern finishes while still retaining that classic Cape Cod charm. Sitting on a large lot, there’s plenty of space for outdoor activities, gardening, boat storage or future expansion. The is ample parking in the driveway as well as two-way access. Ideally situated in the sought-after waterfront town of Rock Hall, you’ll be just minutes from multiple boat ramps, marinas, and a short walk to restaurants, local shops, and the center of town. Whether you're looking for a full-time residence or a weekend getaway, this turn-key home delivers the best of Eastern Shore living. Move-in ready and loaded with upgrades—don’t miss this opportunity!

21305 Haven Rd, Rock Hall

Listing courtesy of RE/MAX Point Realty. Contact:

$365,000

Enjoy the best of both worlds with this well-maintained home situated on a generous 0.653-acre lot just outside of Chestertown! Offering the space and privacy of country living while remaining just minutes from downtown amenities, this 3-bedroom, 2.5-bath home has plenty to offer. **A brand-new well and septic system have just been installed**, providing an important recent improvement for the next owner. Inside, you'll find a welcoming entryway, formal dining room, and spacious kitchen featuring an island, gas cooktop, and cozy breakfast nook. The dedicated laundry room offers convenient access to the side yard, while the comfortable living room provides a warm gathering space centered around a working fireplace. A mix of wood, tile, and carpet flooring adds character throughout the home, and two bathrooms have been recently updated. Outside, enjoy the expansive backyard with room to relax, entertain, or simply take in the extra space. The detached two-car garage offers additional flexibility with a separate area ideal for a workshop, home office, or hobby space, along with a loft ready for your ideas. With a new well and septic system and a convenient location just outside of town, this property offers space, versatility, and the opportunity to enjoy Eastern Shore living close to everything Chestertown has to offer!

3 Beds ⋅ 3 Baths

Enjoy the best of both worlds with this well-maintained home situated on a generous 0.653-acre lot just outside of Chestertown! Offering the space and privacy of country living while remaining just minutes from downtown amenities, this 3-bedroom, 2.5-bath home has plenty to offer. **A brand-new well and septic system have just been installed**, providing an important recent improvement for the next owner. Inside, you'll find a welcoming entryway, formal dining room, and spacious kitchen featuring an island, gas cooktop, and cozy breakfast nook. The dedicated laundry room offers convenient access to the side yard, while the comfortable living room provides a warm gathering space centered around a working fireplace. A mix of wood, tile, and carpet flooring adds character throughout the home, and two bathrooms have been recently updated. Outside, enjoy the expansive backyard with room to relax, entertain, or simply take in the extra space. The detached two-car garage offers additional flexibility with a separate area ideal for a workshop, home office, or hobby space, along with a loft ready for your ideas. With a new well and septic system and a convenient location just outside of town, this property offers space, versatility, and the opportunity to enjoy Eastern Shore living close to everything Chestertown has to offer!

24607 Chestertown Rd, Chestertown

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

$94,900

WELCOME TO THE EASTERN SHORE! | 5.46± ACRES | MILLINGTON, KENT COUNTY, MARYLAND Discover the beauty and peaceful charm of Maryland’s Eastern Shore with this beautiful 5.46± acre fully wooded property in Millington, Kent County! Offering excellent road frontage, a private natural setting, and endless possibilities for outdoor enjoyment, this is an incredible opportunity to own your own piece of Eastern Shore paradise. Surrounded by the beauty of nature, this wooded acreage provides an ideal setting for hunting, recreation, weekend adventures, or creating the perfect homesite. Imagine designing your dream home tucked among the trees, enjoying the quiet country atmosphere, and embracing the relaxed lifestyle that makes the Eastern Shore so special. Conveniently located near the many attractions, waterways, charming communities, and outdoor recreation opportunities throughout the region, this property offers a wonderful balance of peaceful country living and access to local amenities. And with the Chesapeake Bay region and Atlantic coast within reach, you can enjoy the coastal lifestyle and ocean breezes that make this part of Maryland so desirable. Whether you're searching for a private hunting retreat, a recreational getaway, or the perfect place to build your dream home, this beautiful 5.46± acre property is ready for your vision. Beautiful wooded acreage. Excellent road frontage. Peaceful Eastern Shore setting. Endless possibilities. Come discover your own slice of the Eastern Shore in Millington, Maryland!

07 River Rd, Millington

Listing courtesy of Charis Realty Group. Contact:

$525,000

The Perfect Maryland Retreat with Chesapeake Bay Views Close By. Experience the quality of a custom-built Cape Cod crafted by a reputable local builder. Lovingly maintained by its original owner, this home is completely move-in ready and features a freshly painted interior throughout. Whether you are looking for a full-time residence, a weekend getaway, or a holiday retreat, this property offers a peaceful escape. The home features a Chestertown address but sits closer to Rock Hall, giving you the absolute best of both worlds. You are perfectly positioned to enjoy the vibrant Rock Hall festivities and marinas, while still being just a short drive from the famous Chestertown Farmers Market and Historic Downtown, with their variety of Festivals and events throughout the Year. Arrive via the welcoming, roomy front porch, an inviting space to sit, relax, and take in the quiet surroundings. Inside, the main level features an open floor plan where the living room, anchored by a cozy propane fireplace, flows beautifully into the dining area to make the space feel inviting and roomy. The eat-in kitchen opens directly onto a back deck, making outdoor grilling and relaxation easy. The highly sought-after primary bedroom is conveniently located on the main level for easy first-floor living. Upstairs includes additional bedrooms, plenty of easy-access storage space, and a versatile, fully finished bonus room over the garage with a convenient interior entrance—ideal for a home office, hobby room, or guest suite. For hobbies and storage, the property excels. The oversized garage offers ample room for parking plus a dedicated project/workshop space. Below, a partial walk-out basement provides exterior access, making it incredibly easy to store gear or access the home's systems. Situated in a desirable water-oriented community, you will enjoy peekaboo views of the Chesapeake Bay right from the house. Best of all, the neighborhood features its own small private beach for easy enjoyment, making it effortless to relax by the water and perfect for collecting sea glass, beachcombing, and watching the sunset. This classic, beautifully refreshed home is ready for its next chapter!

3 Beds ⋅ 3 Baths

The Perfect Maryland Retreat with Chesapeake Bay Views Close By. Experience the quality of a custom-built Cape Cod crafted by a reputable local builder. Lovingly maintained by its original owner, this home is completely move-in ready and features a freshly painted interior throughout. Whether you are looking for a full-time residence, a weekend getaway, or a holiday retreat, this property offers a peaceful escape. The home features a Chestertown address but sits closer to Rock Hall, giving you the absolute best of both worlds. You are perfectly positioned to enjoy the vibrant Rock Hall festivities and marinas, while still being just a short drive from the famous Chestertown Farmers Market and Historic Downtown, with their variety of Festivals and events throughout the Year. Arrive via the welcoming, roomy front porch, an inviting space to sit, relax, and take in the quiet surroundings. Inside, the main level features an open floor plan where the living room, anchored by a cozy propane fireplace, flows beautifully into the dining area to make the space feel inviting and roomy. The eat-in kitchen opens directly onto a back deck, making outdoor grilling and relaxation easy. The highly sought-after primary bedroom is conveniently located on the main level for easy first-floor living. Upstairs includes additional bedrooms, plenty of easy-access storage space, and a versatile, fully finished bonus room over the garage with a convenient interior entrance—ideal for a home office, hobby room, or guest suite. For hobbies and storage, the property excels. The oversized garage offers ample room for parking plus a dedicated project/workshop space. Below, a partial walk-out basement provides exterior access, making it incredibly easy to store gear or access the home's systems. Situated in a desirable water-oriented community, you will enjoy peekaboo views of the Chesapeake Bay right from the house. Best of all, the neighborhood features its own small private beach for easy enjoyment, making it effortless to relax by the water and perfect for collecting sea glass, beachcombing, and watching the sunset. This classic, beautifully refreshed home is ready for its next chapter!

8901 S Bayview Dr, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$400,000

Nestled in the quiet Tolchester Estates, this charming new construction home, completed in 2026, embodies the pinnacle of low maintenance living. This well-built ranch-style residence offers a harmonious blend of modern living space and coastal charm, perfectly situated approximately 800 feet from the breathtaking Chesapeake Bay. Step inside to discover an open-concept layout that seamlessly integrates the kitchen, dining, and living areas, creating an inviting space ideal for both entertaining and everyday living. The interior features luxury vinyl plank flooring that exudes sophistication while ensuring durability and ease of maintenance. The thoughtfully designed kitchen is a cook's dream, equipped with new appliances including a built-in microwave, dishwasher, stove, and refrigerator, all complemented by a sleek exhaust fan. The combination of functionality and style makes this kitchen the heart of the home. With two spacious bedrooms and a beautifully appointed full bathroom, this residence offers comfort and privacy. The main floor laundry adds convenience to your daily routine, while the attached side-entry garage provides easy access and additional storage options. Step outside onto the expansive deck, where you can bask in the serene views of the bay, perfect for morning coffee or evening gatherings under the stars. The outdoor space is an extension of the easy lifestyle this home offers, allowing you to enjoy the tranquility of nature right at your doorstep. The property is not just a home; it's a lifestyle. Living in Tolchester Estates means embracing a community that values both privacy and connection, with the Chesapeake Bay as your backdrop. Enjoy leisurely strolls along the water, or indulge in water-oriented activities that the bay has to offer. This home is designed for those who appreciate easy living, with a commitment to quality evident in every detail. From the excellent condition of the property to the thoughtful selection of materials, this residence is a jewel. Don't miss the opportunity to own a piece of paradise in this exclusive bay block location. Experience the luxury, comfort, and lifestyle that await you in this remarkable home. Your dream of coastal living starts here. Within 5 minutes of a full-service marina and "The Shanty" for fun entertainment located on a beach right in front of the Chesapeake Bay. There are also community beaches, one is about two minutes from this cottage!

2 Beds ⋅ 2 Baths

Nestled in the quiet Tolchester Estates, this charming new construction home, completed in 2026, embodies the pinnacle of low maintenance living. This well-built ranch-style residence offers a harmonious blend of modern living space and coastal charm, perfectly situated approximately 800 feet from the breathtaking Chesapeake Bay. Step inside to discover an open-concept layout that seamlessly integrates the kitchen, dining, and living areas, creating an inviting space ideal for both entertaining and everyday living. The interior features luxury vinyl plank flooring that exudes sophistication while ensuring durability and ease of maintenance. The thoughtfully designed kitchen is a cook's dream, equipped with new appliances including a built-in microwave, dishwasher, stove, and refrigerator, all complemented by a sleek exhaust fan. The combination of functionality and style makes this kitchen the heart of the home. With two spacious bedrooms and a beautifully appointed full bathroom, this residence offers comfort and privacy. The main floor laundry adds convenience to your daily routine, while the attached side-entry garage provides easy access and additional storage options. Step outside onto the expansive deck, where you can bask in the serene views of the bay, perfect for morning coffee or evening gatherings under the stars. The outdoor space is an extension of the easy lifestyle this home offers, allowing you to enjoy the tranquility of nature right at your doorstep. The property is not just a home; it's a lifestyle. Living in Tolchester Estates means embracing a community that values both privacy and connection, with the Chesapeake Bay as your backdrop. Enjoy leisurely strolls along the water, or indulge in water-oriented activities that the bay has to offer. This home is designed for those who appreciate easy living, with a commitment to quality evident in every detail. From the excellent condition of the property to the thoughtful selection of materials, this residence is a jewel. Don't miss the opportunity to own a piece of paradise in this exclusive bay block location. Experience the luxury, comfort, and lifestyle that await you in this remarkable home. Your dream of coastal living starts here. Within 5 minutes of a full-service marina and "The Shanty" for fun entertainment located on a beach right in front of the Chesapeake Bay. There are also community beaches, one is about two minutes from this cottage!

21338 Virginia Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$650,000

Welcome to this lovely Cape Cod-style, four-bedroom, two-full-bath home situated on .98 acre in Rock Hall, where comfortable living, peaceful surroundings, and the relaxed charm of Maryland��s Eastern Shore come together. A welcoming front porch invites you inside to a spacious living room featuring carpet and floating flooring, an open ceiling accented by beautiful exposed wood beams, two ceiling fans, and a distinctive two-sided fireplace that brings warmth and character to the space. The kitchen features stainless steel appliances, a pantry, and plenty of room for everyday living and entertaining. The upper level features a spacious primary bedroom with carpet and a ceiling fan, along with a private primary bath complete with a relaxing Jacuzzi tub and separate shower. The second bedroom offers carpet, a ceiling fan, a walk-in closet, and a skylight that fills the room with natural light. Just outside, the Trex deck provides a peaceful place to relax and take in beautiful views of the pool, private backyard, and surrounding farmland. On the main level, the front bedroom features carpet and a ceiling fan and is conveniently located near the full bath, complete with corian and tile finishes, a handicap-accessible walk-in shower, and a storage cubby. The rear bedroom, also featuring carpet and a ceiling fan, provides direct access to the screened-in back porch. With Trex flooring, two ceiling fans, and peaceful views of the pool and surrounding farmland, the porch is an inviting spot to enjoy your morning coffee, relax at the end of the day, or simply appreciate the quiet surroundings. Step outside and discover your own private backyard retreat. The vinyl-lined pool is surrounded by a river-stone patio and beautiful mature landscaping, including Japanese maples and crepe myrtles. Wood and wrought-iron fencing add privacy and character, with a pool shed and an additional shed for lawn equipment provide convenient outdoor storage. For those who enjoy life on the water, this location offers wonderful access to everything the Rock Hall area is known for. Grays Inn Creek Marina is approximately two minutes away, with access to Grays Inn Creek and Harrington Creek, which flow into the Chester River. A public landing and pier are also nearby, making it easy to enjoy some of the Eastern Shore’s favorite pastimes—fishing, crabbing, sailing, and boating. Approximately 2.6 miles to downtown Rock Hall welcomes you with restaurants, quaint shops, marinas, and all the unique character of life along the Chesapeake Bay. Whether relaxing by the pool, taking in the peaceful country views, or spending the day on the water, this home offers a wonderful opportunity to enjoy the natural beauty, coastal charm, and laid-back lifestyle that make Rock Hall and Maryland’s Eastern Shore such a special place to call home.

4 Beds ⋅ 2 Baths

Welcome to this lovely Cape Cod-style, four-bedroom, two-full-bath home situated on .98 acre in Rock Hall, where comfortable living, peaceful surroundings, and the relaxed charm of Maryland��s Eastern Shore come together. A welcoming front porch invites you inside to a spacious living room featuring carpet and floating flooring, an open ceiling accented by beautiful exposed wood beams, two ceiling fans, and a distinctive two-sided fireplace that brings warmth and character to the space. The kitchen features stainless steel appliances, a pantry, and plenty of room for everyday living and entertaining. The upper level features a spacious primary bedroom with carpet and a ceiling fan, along with a private primary bath complete with a relaxing Jacuzzi tub and separate shower. The second bedroom offers carpet, a ceiling fan, a walk-in closet, and a skylight that fills the room with natural light. Just outside, the Trex deck provides a peaceful place to relax and take in beautiful views of the pool, private backyard, and surrounding farmland. On the main level, the front bedroom features carpet and a ceiling fan and is conveniently located near the full bath, complete with corian and tile finishes, a handicap-accessible walk-in shower, and a storage cubby. The rear bedroom, also featuring carpet and a ceiling fan, provides direct access to the screened-in back porch. With Trex flooring, two ceiling fans, and peaceful views of the pool and surrounding farmland, the porch is an inviting spot to enjoy your morning coffee, relax at the end of the day, or simply appreciate the quiet surroundings. Step outside and discover your own private backyard retreat. The vinyl-lined pool is surrounded by a river-stone patio and beautiful mature landscaping, including Japanese maples and crepe myrtles. Wood and wrought-iron fencing add privacy and character, with a pool shed and an additional shed for lawn equipment provide convenient outdoor storage. For those who enjoy life on the water, this location offers wonderful access to everything the Rock Hall area is known for. Grays Inn Creek Marina is approximately two minutes away, with access to Grays Inn Creek and Harrington Creek, which flow into the Chester River. A public landing and pier are also nearby, making it easy to enjoy some of the Eastern Shore’s favorite pastimes—fishing, crabbing, sailing, and boating. Approximately 2.6 miles to downtown Rock Hall welcomes you with restaurants, quaint shops, marinas, and all the unique character of life along the Chesapeake Bay. Whether relaxing by the pool, taking in the peaceful country views, or spending the day on the water, this home offers a wonderful opportunity to enjoy the natural beauty, coastal charm, and laid-back lifestyle that make Rock Hall and Maryland’s Eastern Shore such a special place to call home.

21905 Harrington Park Rd, Rock Hall

Listing courtesy of Keller Williams Select Realtors of Easton. Contact:

$425,000

Nestled in Coventry Farms II, this exquisite Colonial-style residence offers a harmonious blend of Space, Convenience and comfort, perfect for those who appreciate the finer things in life. Built in 2009, this stunning home boasts 3,165 square feet of meticulously designed living space, ensuring ample room for both relaxation and entertainment. Step inside to discover an inviting interior adorned with high-end finishes and thoughtful details. The spacious family room, seamlessly connected to the kitchen, is perfect for gatherings, while the formal dining room sets the stage for elegant dinner parties. The gourmet kitchen is a chef's dream, featuring a generous island, stainless steel appliances, and a convenient pantry, all bathed in natural light from the double-pane windows. Enjoy casual meals in the cozy breakfast area, where morning sunlight creates a warm ambiance. Retreat to the luxurious primary suite, complete with a walk-in closet with an additional closet and a spa-like bathroom featuring a walk-in shower and double sinks. Each of the additional three bedrooms offers generous space and comfort and large closets, ensuring everyone has their own sanctuary. Recessed lighting and ceiling fans throughout enhance the home's inviting atmosphere, while plush carpeting and laminate flooring provide a perfect balance of style and practicality. The partially finished basement offers endless possibilities, whether you envision a home theater, gym, or additional living space. The basement even has a rough in for an additional bathroom. With interior access and heating, this area is ready to be transformed into your personal oasis. Outside, the property sits on a 0.28-acre lot that backs to serene trees, while the front over looks the large common area providing a tranquil backdrop for outdoor living. The expansive deck invites you to unwind and entertain, while the attached garage and ample driveway space accommodate all your vehicles with ease. This home is not just a residence; it's a lifestyle. Enjoy the peace of mind that comes with living in a well-established community, where every detail has been considered for your comfort and enjoyment. Experience the perfect blend of luxury, convenience, and nature in this exceptional Coventry Farms II gem that is "Move In Ready". Enjoy a walk in Downtown Historical Chestertown which is on the Chester River. Explore many events that the town has such as Saturday morning Farmers Markets, The Annual Tea Party, Downrigging Festival, Fourth of July Fireworks, tours on the Sultana and River Packet and Dickens of a Christmas or just relax on a bench by the River or Wilmer Park. Don't miss the opportunity to make this dream home your reality! Chestertown is a great place to call Home!

4 Beds ⋅ 3 Baths

Nestled in Coventry Farms II, this exquisite Colonial-style residence offers a harmonious blend of Space, Convenience and comfort, perfect for those who appreciate the finer things in life. Built in 2009, this stunning home boasts 3,165 square feet of meticulously designed living space, ensuring ample room for both relaxation and entertainment. Step inside to discover an inviting interior adorned with high-end finishes and thoughtful details. The spacious family room, seamlessly connected to the kitchen, is perfect for gatherings, while the formal dining room sets the stage for elegant dinner parties. The gourmet kitchen is a chef's dream, featuring a generous island, stainless steel appliances, and a convenient pantry, all bathed in natural light from the double-pane windows. Enjoy casual meals in the cozy breakfast area, where morning sunlight creates a warm ambiance. Retreat to the luxurious primary suite, complete with a walk-in closet with an additional closet and a spa-like bathroom featuring a walk-in shower and double sinks. Each of the additional three bedrooms offers generous space and comfort and large closets, ensuring everyone has their own sanctuary. Recessed lighting and ceiling fans throughout enhance the home's inviting atmosphere, while plush carpeting and laminate flooring provide a perfect balance of style and practicality. The partially finished basement offers endless possibilities, whether you envision a home theater, gym, or additional living space. The basement even has a rough in for an additional bathroom. With interior access and heating, this area is ready to be transformed into your personal oasis. Outside, the property sits on a 0.28-acre lot that backs to serene trees, while the front over looks the large common area providing a tranquil backdrop for outdoor living. The expansive deck invites you to unwind and entertain, while the attached garage and ample driveway space accommodate all your vehicles with ease. This home is not just a residence; it's a lifestyle. Enjoy the peace of mind that comes with living in a well-established community, where every detail has been considered for your comfort and enjoyment. Experience the perfect blend of luxury, convenience, and nature in this exceptional Coventry Farms II gem that is "Move In Ready". Enjoy a walk in Downtown Historical Chestertown which is on the Chester River. Explore many events that the town has such as Saturday morning Farmers Markets, The Annual Tea Party, Downrigging Festival, Fourth of July Fireworks, tours on the Sultana and River Packet and Dickens of a Christmas or just relax on a bench by the River or Wilmer Park. Don't miss the opportunity to make this dream home your reality! Chestertown is a great place to call Home!

106 Harlan Loop, Chestertown

Listing courtesy of Douglas Realty LLC. Contact:

$396,700

Just a 2 blocks from Rock Hall Harbor which accesses the Chesapeake Bay, this adorable Cape Cod is the retreat you’ve been dreaming of. Whether you’re looking for a peaceful primary residence, a weekend or vacation getaway, or an investment property to Airbnb, this home perfectly balances cozy character with nearby conveniences. Peace and quiet doesn’t mean being disconnected. You're just a short stroll or drive from downtown shops and dining, giving you the best of water community living and small-town convenience, such as quaint downtown shops, restaurants like Harbor Shack, Rock Hall Brewing Company, The Little Lemon Leaf Diner, Ford's Seafood, ice cream from Get the Scoop, and much more. Yearly Rock Hall events such as the renowned Pirates and Wenches Weekend, 4th of July Celebration, FallFest, Blessing of the Fleet, Waterman's Day, the Lighted Boat Parade (and so much more) will keep you entertained all year long. Inside the home, enjoy a roomy living room and dining room area that's perfect for hosting guests or quiet nights in. Three bedrooms make for ample space for you and your guests. The second floor bedroom can be left as is, turned into a primary suite, separated into two bedrooms, made into a game room, crafting room, or gathering space - light up your imagination with the possibilities. On the front and back of the home are enclosed porches, great for sipping your morning coffee or enjoy a cozy afternoon in the bright and welcoming space. The detached, oversized 1-car garage offers work and storage space and has an upstairs loft that provides incredible potential for a studio, apartment (plumbing needed), or additional storage. Don’t miss this rare opportunity to own a slice of paradise near the water! Tell your agent that this is the one and have them schedule your showing today. :) **Adjoining additional building lot available**

3 Beds ⋅ 1 Baths

Just a 2 blocks from Rock Hall Harbor which accesses the Chesapeake Bay, this adorable Cape Cod is the retreat you’ve been dreaming of. Whether you’re looking for a peaceful primary residence, a weekend or vacation getaway, or an investment property to Airbnb, this home perfectly balances cozy character with nearby conveniences. Peace and quiet doesn’t mean being disconnected. You're just a short stroll or drive from downtown shops and dining, giving you the best of water community living and small-town convenience, such as quaint downtown shops, restaurants like Harbor Shack, Rock Hall Brewing Company, The Little Lemon Leaf Diner, Ford's Seafood, ice cream from Get the Scoop, and much more. Yearly Rock Hall events such as the renowned Pirates and Wenches Weekend, 4th of July Celebration, FallFest, Blessing of the Fleet, Waterman's Day, the Lighted Boat Parade (and so much more) will keep you entertained all year long. Inside the home, enjoy a roomy living room and dining room area that's perfect for hosting guests or quiet nights in. Three bedrooms make for ample space for you and your guests. The second floor bedroom can be left as is, turned into a primary suite, separated into two bedrooms, made into a game room, crafting room, or gathering space - light up your imagination with the possibilities. On the front and back of the home are enclosed porches, great for sipping your morning coffee or enjoy a cozy afternoon in the bright and welcoming space. The detached, oversized 1-car garage offers work and storage space and has an upstairs loft that provides incredible potential for a studio, apartment (plumbing needed), or additional storage. Don’t miss this rare opportunity to own a slice of paradise near the water! Tell your agent that this is the one and have them schedule your showing today. :) **Adjoining additional building lot available**

5827 S Hawthorne Ave, Rock Hall

Listing courtesy of Iron Valley Real Estate Premier. Contact:

$20,000

5+/- acres of hunting or recreational land in Rock Hall! A 10' right-of-way appears to provide access from the left side of 21425 Berryman Rd. Currently walk-in access only, as vehicles are blocking the right-of-way. Property is mostly wetlands and not buildable. Buyer to perform their own due diligence regarding permitted uses, access/right-of-way, survey, and all other property conditions.

21429 Berryman Rd, Rock Hall

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

$395,000

Nice old home in Rock Hall located on Main Street that needs some TLC. 4 bedrooms, 2 1/2 baths, upgraded kitchen, bath, Florida room and rear deck. Maintenance free exterior (new shingles 2022) and fenced yard. Short walking distance to downtown, shopping, Churches. A short drive to the Chesapeake Bay, Public Landings and Eastern Neck Wildlife Refuge.

4 Beds ⋅ 3 Baths

Nice old home in Rock Hall located on Main Street that needs some TLC. 4 bedrooms, 2 1/2 baths, upgraded kitchen, bath, Florida room and rear deck. Maintenance free exterior (new shingles 2022) and fenced yard. Short walking distance to downtown, shopping, Churches. A short drive to the Chesapeake Bay, Public Landings and Eastern Neck Wildlife Refuge.

5664 S South Main St, Rock Hall

Listing courtesy of Davis Real Estate, Inc.. Contact:

$624,900

Exceptional custom live/work space located on 5 acres at the entrance of Rock Hall. Newly constructed in 2019. This home boasts a screened porch, open living space with hardwood floors, encapsulated crawl space, metal roof, efficient ductless mini-splits, and sophisticated vaulted ceilings. This professional artist studio was completed with architectural lighting, seamlessly lighting the space for the everyday or a special occasion. Currently used as an artist studio, this home and property have the potential to be whatever you desire. The open living space would make an inviting home, perfect for entertaining. The tucked-away loft bedroom is spacious and has exceptional views of the surrounding woods. There is plenty of room on the 5-acre parcel to expand or customize! Prime location with tons of privacy. This gem is tucked away, yet just a short jaunt to all Rock Hall has to offer: marinas, restaurants, Main Street shops, public boat launches, and the Ferry Park beach! Showings by appointment only.

1 Beds ⋅ 1 Baths

Exceptional custom live/work space located on 5 acres at the entrance of Rock Hall. Newly constructed in 2019. This home boasts a screened porch, open living space with hardwood floors, encapsulated crawl space, metal roof, efficient ductless mini-splits, and sophisticated vaulted ceilings. This professional artist studio was completed with architectural lighting, seamlessly lighting the space for the everyday or a special occasion. Currently used as an artist studio, this home and property have the potential to be whatever you desire. The open living space would make an inviting home, perfect for entertaining. The tucked-away loft bedroom is spacious and has exceptional views of the surrounding woods. There is plenty of room on the 5-acre parcel to expand or customize! Prime location with tons of privacy. This gem is tucked away, yet just a short jaunt to all Rock Hall has to offer: marinas, restaurants, Main Street shops, public boat launches, and the Ferry Park beach! Showings by appointment only.

21590 Pine Ln, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

$250,000

Classic home on South Main Street in the town of Rock Hall. Charming in-town farmhouse-style residence on a spacious lot, .36 acres, plus a large garage/ workshop with electric! Step inside to discover a warm and inviting interior. Original solid hardwood floors throughout, traditional floor plan with classic build-ins. The heart of the home is the large country-style kitchen, with ample table space and a pantry. The adjoining family room has a cozy propane fireplace with glass doors, which keeps this home very cozy! The formal dining room gets lots of natural light and leads to a large mudroom/ rear entry. There are three spacious bedrooms upstairs, as well as a half bathroom. There is a full bathroom downstairs. This home is ready for its next chapter. A great opportunity to renovate a property with solid bones in the heart of town! The large yard gives you privacy and room for activities while still being downtown. Walking distance to all Rock Hall has to offer, marinas, restaurants, Main Street shops, public boat launches, Ferry Park beach, and a front seat for the Rock Hall 4th of July parade! Additionally, this home is right across from the Rock Hall Civic Center. New water heater and plumbing throughout the home.

3 Beds ⋅ 2 Baths

Classic home on South Main Street in the town of Rock Hall. Charming in-town farmhouse-style residence on a spacious lot, .36 acres, plus a large garage/ workshop with electric! Step inside to discover a warm and inviting interior. Original solid hardwood floors throughout, traditional floor plan with classic build-ins. The heart of the home is the large country-style kitchen, with ample table space and a pantry. The adjoining family room has a cozy propane fireplace with glass doors, which keeps this home very cozy! The formal dining room gets lots of natural light and leads to a large mudroom/ rear entry. There are three spacious bedrooms upstairs, as well as a half bathroom. There is a full bathroom downstairs. This home is ready for its next chapter. A great opportunity to renovate a property with solid bones in the heart of town! The large yard gives you privacy and room for activities while still being downtown. Walking distance to all Rock Hall has to offer, marinas, restaurants, Main Street shops, public boat launches, Ferry Park beach, and a front seat for the Rock Hall 4th of July parade! Additionally, this home is right across from the Rock Hall Civic Center. New water heater and plumbing throughout the home.

5661 S Main St, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

$599,900

New construction opportunity in Rock Hall with time to make it your own. The current plans feature a 1,650-square-foot ranch-style home with 3 bedrooms, 2 bathrooms, a front porch, and rear deck, all situated on a .79-acre lot within town limits. The open living areas include a large kitchen with white cabinetry, quartz countertops, stainless steel appliances, and upgraded LVP flooring that continues through the living and dining rooms. The primary bedroom features a walk-in closet and en-suite bathroom with dual vanity and shower. Two additional bedrooms have upgraded carpet and share a guest bathroom with a tub/shower. Additional features include an energy efficiency heat pump, a conditioned crawl space and public water and sewer. There is still time to select finishes and add your own personal touches. Buyers may also have the option to make changes to the current plans or choose a different style of home, subject to new permit approval. Located just two blocks from Rock Hall Harbor and close to Haven Harbour and Swan Creek, the property puts boating, marinas, restaurants, shops, and the waterfront all within easy reach. It’s a convenient in-town location for enjoying the laid-back, waterfront lifestyle that makes Rock Hall such a popular Eastern Shore destination.

3 Beds ⋅ 2 Baths

New construction opportunity in Rock Hall with time to make it your own. The current plans feature a 1,650-square-foot ranch-style home with 3 bedrooms, 2 bathrooms, a front porch, and rear deck, all situated on a .79-acre lot within town limits. The open living areas include a large kitchen with white cabinetry, quartz countertops, stainless steel appliances, and upgraded LVP flooring that continues through the living and dining rooms. The primary bedroom features a walk-in closet and en-suite bathroom with dual vanity and shower. Two additional bedrooms have upgraded carpet and share a guest bathroom with a tub/shower. Additional features include an energy efficiency heat pump, a conditioned crawl space and public water and sewer. There is still time to select finishes and add your own personal touches. Buyers may also have the option to make changes to the current plans or choose a different style of home, subject to new permit approval. Located just two blocks from Rock Hall Harbor and close to Haven Harbour and Swan Creek, the property puts boating, marinas, restaurants, shops, and the waterfront all within easy reach. It’s a convenient in-town location for enjoying the laid-back, waterfront lifestyle that makes Rock Hall such a popular Eastern Shore destination.

21008 Rock Hall Ave, Rock Hall

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

$160,000

Cleared 100 ft x 196 ft building lot with public water & sewer in the desirable Ferry Park area of Rock Hall. The lot has an existing 10' x 20' storage shed on the property. The lot is NOT in the flood plain, but it is in the Intense Development Area of the Chesapeake Bay Critical Area. Close to restaurants, marinas, and the public beach this is a nice spot to build the Eastern Shore home of your dreams. Very few building lots remain in the town of Rock Hall, especially like this one with public water & sewer on site and not in a flood plain!

5830 Locust St, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$224,900

Welcome to 28036 Creamery Street in Kennedyville. Built in 1920, this two-story home offers 3 bedrooms, 1 full bath and 1,296 square feet of living space, along with two parcels totaling approximately .224 acre. The main level features a large kitchen with a sightline into the dining room, living room, full bath, and a convenient laundry/utility area located just off the dining room. All three bedrooms are located on the upper level. The home is functional and ready for its next owner, while also offering an opportunity for buyers who would like to make improvements and updates over time to suit their own style. The sale includes the .109-acre homesite plus an adjoining .115-acre parcel, providing additional outdoor space and possibilities. Located in the Eastern Shore community of Kennedyville, the property is a short drive to historic Chestertown for shopping, dining and everyday conveniences. Enjoy access to the area's outdoor recreation, including the Sassafras River, Turner's Creek and Sassafras Natural Resources Management Area, with opportunities for boating, fishing, kayaking and hiking. Betterton and Rock Hall provide additional Chesapeake Bay destinations within the surrounding area. Routes 213 and 301 also provides connections toward Middletown, Dover and surrounding employment and shopping areas. Property is being sold As-Is.

3 Beds ⋅ 1 Baths

Welcome to 28036 Creamery Street in Kennedyville. Built in 1920, this two-story home offers 3 bedrooms, 1 full bath and 1,296 square feet of living space, along with two parcels totaling approximately .224 acre. The main level features a large kitchen with a sightline into the dining room, living room, full bath, and a convenient laundry/utility area located just off the dining room. All three bedrooms are located on the upper level. The home is functional and ready for its next owner, while also offering an opportunity for buyers who would like to make improvements and updates over time to suit their own style. The sale includes the .109-acre homesite plus an adjoining .115-acre parcel, providing additional outdoor space and possibilities. Located in the Eastern Shore community of Kennedyville, the property is a short drive to historic Chestertown for shopping, dining and everyday conveniences. Enjoy access to the area's outdoor recreation, including the Sassafras River, Turner's Creek and Sassafras Natural Resources Management Area, with opportunities for boating, fishing, kayaking and hiking. Betterton and Rock Hall provide additional Chesapeake Bay destinations within the surrounding area. Routes 213 and 301 also provides connections toward Middletown, Dover and surrounding employment and shopping areas. Property is being sold As-Is.

28036 Creamery St, Kennedyville

Listing courtesy of BHHS Fox & Roach-Christiana. Contact:

$679,900

Welcome to 8986 Orchard Drive, tucked away in the sought-after Orchard Hill neighborhood just outside of Chestertown! This move-in-ready home offers comfortable one-level living with 3 bedrooms, 2 bathrooms, and a partially finished basement with endless possibilities. Enjoy a spacious living room with recessed ceilings, an inviting primary suite with a jetted soaking tub, and updates throughout, including a new roof in 2025 and an efficient HVAC system upgraded in 2022. The partially finished basement features a private, ground-level walkout entrance, studio-style living space with a pool table, an efficient mini-split system, and plenty of additional storage or workshop space. French drains and an automatic sump pump add peace of mind. Outside, enjoy multiple spaces to relax and entertain, including a screened-in porch, open deck, patio with a hot tub that conveys, and a partially fenced backyard surrounded by beautiful crepe myrtles. Additional highlights include a two-car garage, a large floored attic for extra storage, and a solar system installed in August 2025. Conveniently located within 10 minutes of Chestertown's everyday amenities, shopping, dining, and more, this property offers the perfect blend of comfort, flexibility, and convenience. Come see all that this home has to offer! *Sellers offering credit towards painting*

3 Beds ⋅ 4 Baths

Welcome to 8986 Orchard Drive, tucked away in the sought-after Orchard Hill neighborhood just outside of Chestertown! This move-in-ready home offers comfortable one-level living with 3 bedrooms, 2 bathrooms, and a partially finished basement with endless possibilities. Enjoy a spacious living room with recessed ceilings, an inviting primary suite with a jetted soaking tub, and updates throughout, including a new roof in 2025 and an efficient HVAC system upgraded in 2022. The partially finished basement features a private, ground-level walkout entrance, studio-style living space with a pool table, an efficient mini-split system, and plenty of additional storage or workshop space. French drains and an automatic sump pump add peace of mind. Outside, enjoy multiple spaces to relax and entertain, including a screened-in porch, open deck, patio with a hot tub that conveys, and a partially fenced backyard surrounded by beautiful crepe myrtles. Additional highlights include a two-car garage, a large floored attic for extra storage, and a solar system installed in August 2025. Conveniently located within 10 minutes of Chestertown's everyday amenities, shopping, dining, and more, this property offers the perfect blend of comfort, flexibility, and convenience. Come see all that this home has to offer! *Sellers offering credit towards painting*

8986 Orchard Dr, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

$325,000

Some houses are finished. This one is full of opportunity. Built circa 1920, this Victorian sits in one of Downtown Chestertown's most desirable neighborhoods — and it's waiting for someone who can see what it is meant to become. The hard work and the expensive work have already been done: new cedar siding, blown-in insulation, and original hardwood floors throughout. What remains is the fun part. The kitchen and baths are a genuine blank slate, ready for your design, your finishes, your vision. And the bones… remarkable. Solid construction, generous proportions, and historic detail at every turn — the kind of craftsmanship that simply isn't built anymore, and can't be bought back once it's gone. Start with a house of real character and your renovation adds value instead of merely keeping up. Upstairs, five generous bedroom and two full baths. A rare third-floor primary suite offers space and privacy set apart from the rest of the home — a true owner's retreat, a guest wing, or a quiet work-from-home floor of its own. Outside, a fully fenced backyard is ready for pets, play, and entertaining, a large shed could easily become a garage, studio, or workshop. The driveway provides off-street parking, a definite bonus for Chestertown. And the location is the whole point. You're roughly three blocks from everything Chestertown offers — the shops, restaurants and galleries along High Street, the Chester River waterfront, the farmers market, and the historic charm of one of the Eastern Shore's best-loved small towns. Bring your contractor, or be your own. Come see the possibility.

5 Beds ⋅ 2 Baths

Some houses are finished. This one is full of opportunity. Built circa 1920, this Victorian sits in one of Downtown Chestertown's most desirable neighborhoods — and it's waiting for someone who can see what it is meant to become. The hard work and the expensive work have already been done: new cedar siding, blown-in insulation, and original hardwood floors throughout. What remains is the fun part. The kitchen and baths are a genuine blank slate, ready for your design, your finishes, your vision. And the bones… remarkable. Solid construction, generous proportions, and historic detail at every turn — the kind of craftsmanship that simply isn't built anymore, and can't be bought back once it's gone. Start with a house of real character and your renovation adds value instead of merely keeping up. Upstairs, five generous bedroom and two full baths. A rare third-floor primary suite offers space and privacy set apart from the rest of the home — a true owner's retreat, a guest wing, or a quiet work-from-home floor of its own. Outside, a fully fenced backyard is ready for pets, play, and entertaining, a large shed could easily become a garage, studio, or workshop. The driveway provides off-street parking, a definite bonus for Chestertown. And the location is the whole point. You're roughly three blocks from everything Chestertown offers — the shops, restaurants and galleries along High Street, the Chester River waterfront, the farmers market, and the historic charm of one of the Eastern Shore's best-loved small towns. Bring your contractor, or be your own. Come see the possibility.

234 N Kent St, Chestertown

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

$281,500

Discover relaxed Eastern Shore living at 8820 Cumberland Street, a charming three-bedroom, two-full-bath home offering the ease and convenience of single-level living in the peaceful water-privileged community of Tolchester Beach. Built in 2006, this inviting residence combines a comfortable floor plan, desirable outdoor space, and an attached two-car garage with a setting that encourages you to slow down and enjoy the best of Maryland's Eastern Shore. The thoughtfully designed interior provides an easy flow for everyday living, with three well-proportioned bedrooms and two full baths all conveniently located on one level. Whether you're entertaining, working from home, or simply enjoying a quiet evening, the home's practical layout offers flexibility for a variety of lifestyles. Step outside to the rear deck, where a wooded backdrop creates a tranquil setting for morning coffee, outdoor dining, or relaxing at the end of the day. The surrounding natural scenery adds a welcome sense of privacy and peacefulness. The community's water-oriented amenities add to the appeal, with opportunities to enjoy the community beach, fishing, local marina, and the laid-back lifestyle that makes the Eastern Shore so desirable. Ideally positioned between historic Chestertown and waterfront Rock Hall, the home places shopping, dining, marinas, boating, and local recreation within convenient reach. Whether you're seeking a full-time residence, weekend retreat, or low-maintenance Eastern Shore escape, 8820 Cumberland Street offers an appealing blend of comfort, convenience, and coastal lifestyle. This property is being sold as-is, property is lender-owned and U.S. Bank National Association is making no representations or warranties. U.S. Bank National Association may have financing options available.

3 Beds ⋅ 2 Baths

Discover relaxed Eastern Shore living at 8820 Cumberland Street, a charming three-bedroom, two-full-bath home offering the ease and convenience of single-level living in the peaceful water-privileged community of Tolchester Beach. Built in 2006, this inviting residence combines a comfortable floor plan, desirable outdoor space, and an attached two-car garage with a setting that encourages you to slow down and enjoy the best of Maryland's Eastern Shore. The thoughtfully designed interior provides an easy flow for everyday living, with three well-proportioned bedrooms and two full baths all conveniently located on one level. Whether you're entertaining, working from home, or simply enjoying a quiet evening, the home's practical layout offers flexibility for a variety of lifestyles. Step outside to the rear deck, where a wooded backdrop creates a tranquil setting for morning coffee, outdoor dining, or relaxing at the end of the day. The surrounding natural scenery adds a welcome sense of privacy and peacefulness. The community's water-oriented amenities add to the appeal, with opportunities to enjoy the community beach, fishing, local marina, and the laid-back lifestyle that makes the Eastern Shore so desirable. Ideally positioned between historic Chestertown and waterfront Rock Hall, the home places shopping, dining, marinas, boating, and local recreation within convenient reach. Whether you're seeking a full-time residence, weekend retreat, or low-maintenance Eastern Shore escape, 8820 Cumberland Street offers an appealing blend of comfort, convenience, and coastal lifestyle. This property is being sold as-is, property is lender-owned and U.S. Bank National Association is making no representations or warranties. U.S. Bank National Association may have financing options available.

8820 Cumberland St, Chestertown

Listing courtesy of RE/MAX Advantage Realty. Contact:

$1,800,000

**Price increase due to the home’s expanded footprint—over 1,200 additional square feet!** **To be built! Welcome to this beautifully designed 3,540 sq. ft. home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The standard floor plan includes 4 bedrooms and 3.5 baths, with the option to expand to 5 bedrooms and 4.5 baths by adding a first-floor guest suite. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath and walk-in closet, complemented by a convenient second-floor laundry. Designed with future needs in mind, this home also offers the option of a residential elevator for effortless access across all levels. Enjoy broad water views and breathtaking sunrises over the Chester River. The covered porches and expansive windows create a seamless connection to the outdoors, enhancing the waterfront lifestyle of this sought-after community. Deep water boat slips are available for lease or purchase. The community amenities include two docks, pool, grilling and outdoor dining area right on the water, large firepit, area to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! Nestled in the sought-after Chester River Landing community, this home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

4 Beds ⋅ 4 Baths

**Price increase due to the home’s expanded footprint—over 1,200 additional square feet!** **To be built! Welcome to this beautifully designed 3,540 sq. ft. home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The standard floor plan includes 4 bedrooms and 3.5 baths, with the option to expand to 5 bedrooms and 4.5 baths by adding a first-floor guest suite. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath and walk-in closet, complemented by a convenient second-floor laundry. Designed with future needs in mind, this home also offers the option of a residential elevator for effortless access across all levels. Enjoy broad water views and breathtaking sunrises over the Chester River. The covered porches and expansive windows create a seamless connection to the outdoors, enhancing the waterfront lifestyle of this sought-after community. Deep water boat slips are available for lease or purchase. The community amenities include two docks, pool, grilling and outdoor dining area right on the water, large firepit, area to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! Nestled in the sought-after Chester River Landing community, this home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

Little Harbor Way Unit 1, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$259,900

Ask about our SELLER-PAID RATE BUYDOWN — the builder is paying to permanently lower your interest rate when you finance with our preferred lender, who is also contributing toward your closing costs. The result: a dramatically lower monthly payment on a brand-new home, saving you well over a hundred dollars every month — even more on lower-down-payment financing. This is real payment relief in today's market — often the difference between watching and owning. Brand-new construction in the heart of Chestertown. Buydown applies with use of preferred lender; see agent for details. Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you’ll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Additional highlights include exclusive financing opportunities with zero down payment loans, paid closing cost programs, and discounted interest rates—making it possible to own this home for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown’s most historic locations. Ask about Special Financing Offers and how to get $7,500 or more in closing help from the builder's preferred lender and on select models, while they last!

3 Beds ⋅ 3 Baths

Ask about our SELLER-PAID RATE BUYDOWN — the builder is paying to permanently lower your interest rate when you finance with our preferred lender, who is also contributing toward your closing costs. The result: a dramatically lower monthly payment on a brand-new home, saving you well over a hundred dollars every month — even more on lower-down-payment financing. This is real payment relief in today's market — often the difference between watching and owning. Brand-new construction in the heart of Chestertown. Buydown applies with use of preferred lender; see agent for details. Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you’ll find generously sized bedrooms including a large primary suite with walk-in closet and private bath. Additional highlights include exclusive financing opportunities with zero down payment loans, paid closing cost programs, and discounted interest rates—making it possible to own this home for less than area rents. Delivered at the asking price as shown in the photos, this home combines modern style, comfort, and convenience in one of Chestertown’s most historic locations. Ask about Special Financing Offers and how to get $7,500 or more in closing help from the builder's preferred lender and on select models, while they last!

103 Metcalf Rd, Chestertown

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

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