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Tucked neatly on a corner in Chesapeake Landing, this three-quarter acre parcel is among one of the largest in the neighborhood. The 2020 custom built home exudes simple luxury. Offering three bedrooms and two full baths in a simple and efficient floorplan, is has flow and comfort in mind. It features a modern kitchen with tall quiet close cabinets, granite counter tops and a tile backsplash, stainless appliances, and an ample pantry for storage. Six-over-six oversized windows throughout the home, extra tall doors, a transom window over the front door, and a ten-foot door to the screen porch allows light to pour inside. A full and separate laundry room remove that chore from the living space and offer a dedicated work room with storage. The Primary Suite includes a generous walk-in closet and en suite bath. Since 2021, upgrades and improvements include: screened porch, Leafguard on all gutters, shed to coordinate with the home’s aesthetics, asphalt driveway, thoughtful landscaping, water treatment system, and is wired for IQ Fiber (formerly ThinkBig) for internet. This home is absolutely, without question, turnkey and ready for its new stewards!

23264 Clarissa Rd, Chestertown

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

Selling Office: Rosendale Realty.

$364,900

New Construction Alert! The last two beautiful 3BR, 2.5 bath duplexes under construction on Striper Run in Watermans Estates are now for sale. Nice open 1st floor layout with living, dining & kitchen areas, powder room and separate laundry room. Luxury vinyl plank flooring in the 1st and 2nd levels is included. Upstairs, there's a primary suite with walk-in closet, full bath, two more spacious bedrooms and another full bath. The 7' x 23' storage room with overhead door provides lots of space for toys and tools. Out back there's a concrete patio and 6 ft vinyl privacy fence. Watermans Estates is an attractive community in the heart of Rock Hall. Walkable or bike-able to restaurants, marinas and shops the location offers easy access to Rock Hall's many festivals and fun events.

New Construction Alert! The last two beautiful 3BR, 2.5 bath duplexes under construction on Striper Run in Watermans Estates are now for sale. Nice open 1st floor layout with living, dining & kitchen areas, powder room and separate laundry room. Luxury vinyl plank flooring in the 1st and 2nd levels is included. Upstairs, there's a primary suite with walk-in closet, full bath, two more spacious bedrooms and another full bath. The 7' x 23' storage room with overhead door provides lots of space for toys and tools. Out back there's a concrete patio and 6 ft vinyl privacy fence. Watermans Estates is an attractive community in the heart of Rock Hall. Walkable or bike-able to restaurants, marinas and shops the location offers easy access to Rock Hall's many festivals and fun events.

21133 Striper Run, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: RE/MAX Chesapeake.

$364,900

New Year, new home! No need to worry for years about the roof or mechanics!! Built in 2023 - this Smart Home is tucked into a quiet and friendly Chestertown community. Thoughtfully enhanced throughout, the kitchen shines with new quartz countertops, a stylish backsplash, upgraded sink and faucet, and added cabinetry with elegant hardware. Fresh light fixtures bring a warm glow to the living spaces, while the laundry room offers added function with quartz surfaces and extra storage. The powder room has been transformed with a stunning vanity and modern fixtures. The second floor offers four spacious bedrooms and two full baths. As a bonus, this property is a smart home, offering comfort and convenience at your fingertips. Just a short drive to multiple marinas in Rock Hall and an easy drive to Philadelphia and Washington, D.C.

4 Beds ⋅ 3 Baths

New Year, new home! No need to worry for years about the roof or mechanics!! Built in 2023 - this Smart Home is tucked into a quiet and friendly Chestertown community. Thoughtfully enhanced throughout, the kitchen shines with new quartz countertops, a stylish backsplash, upgraded sink and faucet, and added cabinetry with elegant hardware. Fresh light fixtures bring a warm glow to the living spaces, while the laundry room offers added function with quartz surfaces and extra storage. The powder room has been transformed with a stunning vanity and modern fixtures. The second floor offers four spacious bedrooms and two full baths. As a bonus, this property is a smart home, offering comfort and convenience at your fingertips. Just a short drive to multiple marinas in Rock Hall and an easy drive to Philadelphia and Washington, D.C.

108 Flying Cloud Dr, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Coldwell Banker Realty.

$364,900

New Construction Alert! Four beautiful 3BR, 2.5 bath duplexes under construction on Striper Run in Watermans Estates. Nice open 1st floor layout with living, dining & kitchen areas, powder room and separate laundry room. Luxury vinyl plank flooring in the living areas, granite counter tops and stainless appliances are included. Upstairs, there's a primary suite with walk-in closet, full bath, two more spacious bedrooms and another full bath. The 7' x 23' storage room with overhead door provides lots of space for toys and tools. Out back there's a concrete patio and 6 ft vinyl privacy fence. Watermans Estates is an attractive community in the heart of Rock Hall. Walkable or bike-able to restaurants, marinas and shops the location offers easy access to Rock Hall's many festivals and fun events.

New Construction Alert! Four beautiful 3BR, 2.5 bath duplexes under construction on Striper Run in Watermans Estates. Nice open 1st floor layout with living, dining & kitchen areas, powder room and separate laundry room. Luxury vinyl plank flooring in the living areas, granite counter tops and stainless appliances are included. Upstairs, there's a primary suite with walk-in closet, full bath, two more spacious bedrooms and another full bath. The 7' x 23' storage room with overhead door provides lots of space for toys and tools. Out back there's a concrete patio and 6 ft vinyl privacy fence. Watermans Estates is an attractive community in the heart of Rock Hall. Walkable or bike-able to restaurants, marinas and shops the location offers easy access to Rock Hall's many festivals and fun events.

21141 Striper Run, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: ExecuHome Realty.

$364,000

Charming Brick Rancher in the Heart of Chestertown Discover this classic brick rancher nestled in one of Chestertown’s established neighborhoods. Enjoy the convenience of being just a short walk or bike ride from downtown, where you’ll find favorite local shops, restaurants, and the beloved Saturday morning Farmers Market. This home offers the perfect blend of small-town charm, walkability, and timeless appeal. This traditional 3-bedroom, 2-full-bath home features an open and inviting living room filled with natural light. All windows have been updated and replaced, the crawl space has been professionally repaired, encapsulated, and equipped with a dehumidifier for added efficiency and comfort. The roof and heating/cooling system are both on the newer side, offering added peace of mind for years to come. The home has earned a Certificate of Completion from the Delmarva Power Home Performance with Energy Star Program, ensuring enhanced energy efficiency throughout. Enjoy relaxing in the bright sunroom or spending quiet moments in the fenced backyard—perfect for outdoor living and entertaining. A backyard shed provides convenient storage for tools, bikes, and more. Truly move-in ready, this home is waiting for you to make it your own!

Charming Brick Rancher in the Heart of Chestertown Discover this classic brick rancher nestled in one of Chestertown’s established neighborhoods. Enjoy the convenience of being just a short walk or bike ride from downtown, where you’ll find favorite local shops, restaurants, and the beloved Saturday morning Farmers Market. This home offers the perfect blend of small-town charm, walkability, and timeless appeal. This traditional 3-bedroom, 2-full-bath home features an open and inviting living room filled with natural light. All windows have been updated and replaced, the crawl space has been professionally repaired, encapsulated, and equipped with a dehumidifier for added efficiency and comfort. The roof and heating/cooling system are both on the newer side, offering added peace of mind for years to come. The home has earned a Certificate of Completion from the Delmarva Power Home Performance with Energy Star Program, ensuring enhanced energy efficiency throughout. Enjoy relaxing in the bright sunroom or spending quiet moments in the fenced backyard—perfect for outdoor living and entertaining. A backyard shed provides convenient storage for tools, bikes, and more. Truly move-in ready, this home is waiting for you to make it your own!

303 E Campus Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$362,000

Tucked just off Rock Hall’s Main Street, this 3-bedroom, 2-bath rancher offers easy, single-level living in one of the Eastern Shore’s most beloved waterfront towns. Lovingly cared for by its original owner, the home features a comfortable, open-concept layout connecting the living, dining, and kitchen areas. The primary suite includes an en-suite bathroom and walk-in closet, while two additional bedrooms and a full bath provide flexibility for guests, a home office, or both. The welcoming front porch is a perfect spot to start or end your day. Out back, a spacious shed provides excellent storage or potential for a workshop. Just minutes from Rock Hall’s marinas, restaurants, and local shops, this is a rare opportunity to own a well-kept home in a location that makes enjoying the Eastern Shore lifestyle easy.

Tucked just off Rock Hall’s Main Street, this 3-bedroom, 2-bath rancher offers easy, single-level living in one of the Eastern Shore’s most beloved waterfront towns. Lovingly cared for by its original owner, the home features a comfortable, open-concept layout connecting the living, dining, and kitchen areas. The primary suite includes an en-suite bathroom and walk-in closet, while two additional bedrooms and a full bath provide flexibility for guests, a home office, or both. The welcoming front porch is a perfect spot to start or end your day. Out back, a spacious shed provides excellent storage or potential for a workshop. Just minutes from Rock Hall’s marinas, restaurants, and local shops, this is a rare opportunity to own a well-kept home in a location that makes enjoying the Eastern Shore lifestyle easy.

5883 Williams St, Rock Hall

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

Selling Office: Clark & Co Realty, LLC.

$361,500

Highly sought after downtown Historic Chestertown. This 3 unit property is ready to rent. Recently updated and renovated throughout the years, pride of ownership is apparent. The main level has a Studio with new kitchen, full bath and large living area. There is a door to the new deck and quiet back yard. Heating is a gas unit and cooling would be a window unit- super efficient space. The main level also has a 1 bedroom unit. It too has a door to the deck and back yard. The upper level has a 2 bedroom unit. The wood floors have been refinished and other flooring has been updated. Each unit has a seperate leased propane tank. The front porch was re-decked 3 years ago. Live in one and rent the others- great way to get to live in this spectacular historic town!! Too many updates to list. Book a tour today

517 High St, Chestertown

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

Selling Office: Select Land & Homes, LLC.

$360,000

Back on market due to no fault of the sellers! Welcome to this charming and well-maintained 3-bedroom, 2.5-bath home offering a cozy layout and desirable amenities throughout. This home features multiple living spaces—including a bright sunroom and a separate dining area providing comfort and versatility for everyday living. The spacious primary bedroom features vaulted ceilings, an en suite bath, and a large walk-in closet. Cozy up by one of the fireplaces and enjoy the private backyard offering an inviting retreat with an in-ground pool and a spa hook-up ready for future installation. A garage adds convenience for parking and storage, making this home a wonderful opportunity for anyone seeking comfort, charm, and great amenities in one place.

Back on market due to no fault of the sellers! Welcome to this charming and well-maintained 3-bedroom, 2.5-bath home offering a cozy layout and desirable amenities throughout. This home features multiple living spaces—including a bright sunroom and a separate dining area providing comfort and versatility for everyday living. The spacious primary bedroom features vaulted ceilings, an en suite bath, and a large walk-in closet. Cozy up by one of the fireplaces and enjoy the private backyard offering an inviting retreat with an in-ground pool and a spa hook-up ready for future installation. A garage adds convenience for parking and storage, making this home a wonderful opportunity for anyone seeking comfort, charm, and great amenities in one place.

186 Birchwood Ln, Galena

Listing courtesy of Crown Homes Real Estate. Contact:

Selling Office: Foraker Realty Co..

$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:

Selling Office: Benson & Mangold, LLC.

$359,000

Move-in ready and freshly updated in 2025! This 3-bedroom, 2-bath home offers approx. 1,600 sq. ft. of stylish living on an 2.66 acre corner lot with public water and sewer. Every detail has been thoughtfully upgraded—appliances and systems are brand new, complemented by luxury vinyl plank flooring throughout. The spacious layout includes a large mudroom and plenty of modern finishes. Located just minutes from Fairlee Creek’s public landing for easy water access, and a short drive to downtown Chestertown and Rock Hall, this home combines comfort, convenience, and Chesapeake charm. PROPERTY CAN BE PURCHASED FOR $314,000 with .39 acres after recordation this acreage will be subdivided MLS #MDKE2005074, 1.8 ACRES SUBDIVIDED INTO 4 LOTS

4 Beds ⋅ 2 Baths

Move-in ready and freshly updated in 2025! This 3-bedroom, 2-bath home offers approx. 1,600 sq. ft. of stylish living on an 2.66 acre corner lot with public water and sewer. Every detail has been thoughtfully upgraded—appliances and systems are brand new, complemented by luxury vinyl plank flooring throughout. The spacious layout includes a large mudroom and plenty of modern finishes. Located just minutes from Fairlee Creek’s public landing for easy water access, and a short drive to downtown Chestertown and Rock Hall, this home combines comfort, convenience, and Chesapeake charm. PROPERTY CAN BE PURCHASED FOR $314,000 with .39 acres after recordation this acreage will be subdivided MLS #MDKE2005074, 1.8 ACRES SUBDIVIDED INTO 4 LOTS

8833 Georgetown Rd, Chestertown

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

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$355,000

This home was formerly the old Worton Elementary schoolhouse and still retains some of the original features, such as tin ceilings in the living room. The main level has a spacious living room with wood floors, huge kitchen with wood stove, a main level bedroom with a sitting room and full bath with a walk-in shower, and additional hall bath with laundry, several additional rooms and 2 screened porches. The second level has 2 bedrooms and a full bath. You can park in the circle drive or park in one of the bays in the detached 3 car garage. Situated on just over 4 acres with right away access from Worton Road. Propane heat and central A/C will keep you toasty in the winter and cool in the summer. The exterior is mainly cedar siding that will require some TLC.

This home was formerly the old Worton Elementary schoolhouse and still retains some of the original features, such as tin ceilings in the living room. The main level has a spacious living room with wood floors, huge kitchen with wood stove, a main level bedroom with a sitting room and full bath with a walk-in shower, and additional hall bath with laundry, several additional rooms and 2 screened porches. The second level has 2 bedrooms and a full bath. You can park in the circle drive or park in one of the bays in the detached 3 car garage. Situated on just over 4 acres with right away access from Worton Road. Propane heat and central A/C will keep you toasty in the winter and cool in the summer. The exterior is mainly cedar siding that will require some TLC.

10740 Worton Rd, Worton

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Cross Street Realtors LLC.

$355,000

A Rare Opportunity in the Heart of Historic Chestertown Discover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage. Brimming with character and potential, the property currently features a townhouse on one side and two apartments on the other, offering a flexible layout ideal for renovation, income generation, or a creative reimagining. Whether you're envisioning a stately single-family residence, a dynamic live/work space, or a thoughtfully restored multi-unit investment, the possibilities are as expansive as the lot itself. That said, this is not a turnkey property. Significant settling has occurred over the years, and a substantial renovation will be required to bring it back to life. Offered strictly as-is, this is a true fixer-upper for the visionary buyer ready to take on a transformative project. Situated within both the Arts & Entertainment District and Enterprise Zone, this location supports both residential and business uses—making it an ideal candidate for those looking to merge lifestyle, business, and history. **See updated zoning info and description from town office in Documents. Bring your vision, creativity, and tools—and seize the chance to breathe new life into a piece of Chestertown’s storied past. Opportunities like this don’t come along often. Schedule your showing today and imagine the future you can build here.

349 & 351 High St, Chestertown

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

Selling Office: Taylor Properties.

Desirable in-town living in a peaceful neighborhood. This solid brick front rancher was totally renovated in 2022 and is still like New. The pictures tell the story. Easy one-level living with an open concept for the Living Room, Dining, and Kitchen. A really open feel. This home offers 4 bedrooms and 2 full bathrooms. If this many bedrooms are not needed, the fourth bedroom could have many other potential uses, with it being right off the kitchen and living room. Out front, you have a cozy front porch, and out from the sliding glass door it opens up to a deck and a good-size backyard. Just pick where you would like to sit for a few and relax. In the back of the yard, you have a new storage shed that is always a plus. Bring your bikes; you will have the perfect streets in this neighborhood to ride and use as you head to the Local Farmers Market. The pictures show this house perfectly. It is in such good condition and has been well cared for and maintained. All ready to move into. It won't disappoint.

4 Beds ⋅ 2 Baths

Desirable in-town living in a peaceful neighborhood. This solid brick front rancher was totally renovated in 2022 and is still like New. The pictures tell the story. Easy one-level living with an open concept for the Living Room, Dining, and Kitchen. A really open feel. This home offers 4 bedrooms and 2 full bathrooms. If this many bedrooms are not needed, the fourth bedroom could have many other potential uses, with it being right off the kitchen and living room. Out front, you have a cozy front porch, and out from the sliding glass door it opens up to a deck and a good-size backyard. Just pick where you would like to sit for a few and relax. In the back of the yard, you have a new storage shed that is always a plus. Bring your bikes; you will have the perfect streets in this neighborhood to ride and use as you head to the Local Farmers Market. The pictures show this house perfectly. It is in such good condition and has been well cared for and maintained. All ready to move into. It won't disappoint.

213 Byford Dr, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Cross Street Realtors LLC.

Selling Office: Unrepresented Buyer Office.

1 Beds ⋅ 1 Baths

25195 Lovers Ln, Chestertown

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

New construction duplex in desirable Waterman’s Estates! Move-in ready 3BR, 2.5BA home with quality finishes throughout including luxury vinyl plank flooring on both levels, quartz countertops, and stainless steel appliances. Open-concept first floor offers spacious living, dining, and kitchen areas, plus powder room and separate laundry room. Upstairs features a primary suite with walk-in closet and private bath, two additional bedrooms, and full hall bath. Large 7’ x 23’ storage room with overhead door provides excellent storage for bikes, tools, and recreational equipment. Rear concrete patio and 6’ vinyl privacy fence included. Located in the heart of Rock Hall with easy walkability or bike access to restaurants, marinas, shops, festivals, and waterfront attractions. Last duplex available on Striper Run. Easy to show.

New construction duplex in desirable Waterman’s Estates! Move-in ready 3BR, 2.5BA home with quality finishes throughout including luxury vinyl plank flooring on both levels, quartz countertops, and stainless steel appliances. Open-concept first floor offers spacious living, dining, and kitchen areas, plus powder room and separate laundry room. Upstairs features a primary suite with walk-in closet and private bath, two additional bedrooms, and full hall bath. Large 7’ x 23’ storage room with overhead door provides excellent storage for bikes, tools, and recreational equipment. Rear concrete patio and 6’ vinyl privacy fence included. Located in the heart of Rock Hall with easy walkability or bike access to restaurants, marinas, shops, festivals, and waterfront attractions. Last duplex available on Striper Run. Easy to show.

21131 Striper Run, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: Long & Foster Real Estate, Inc..

Discover this well-maintained 2004 rancher located in a water-privileged community with access to the Chesapeake Bay. This charming home offers 3 bedrooms, 2 full baths, and beautiful wood floors throughout. The full unfinished basement is already roughed in for a future bathroom, giving you outstanding potential for added living space. A floored walk-up attic provides even more room for storage or expansion. Additional features include an attached garage and a screened porch perfect for enjoying the outdoors. Tolchester Estates offers the relaxed Eastern Shore lifestyle buyers love—quiet streets and access to the Bay.

Discover this well-maintained 2004 rancher located in a water-privileged community with access to the Chesapeake Bay. This charming home offers 3 bedrooms, 2 full baths, and beautiful wood floors throughout. The full unfinished basement is already roughed in for a future bathroom, giving you outstanding potential for added living space. A floored walk-up attic provides even more room for storage or expansion. Additional features include an attached garage and a screened porch perfect for enjoying the outdoors. Tolchester Estates offers the relaxed Eastern Shore lifestyle buyers love—quiet streets and access to the Bay.

21111 Texas Ave, Chestertown

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

Selling Office: Douglas Realty LLC.

Chesapeake Landing - This home is featured on a corner lot with large living space and additional space above the detached two car garage. Opportunity is knocking at this property, for you to make your forever home. The home features a beautiful sunroom to entertain in as well as a large family room. This home has a large laundry room that is a must have! The hardwood floors are just another great feature of this home. Call today for your showing appointment.

Chesapeake Landing - This home is featured on a corner lot with large living space and additional space above the detached two car garage. Opportunity is knocking at this property, for you to make your forever home. The home features a beautiful sunroom to entertain in as well as a large family room. This home has a large laundry room that is a must have! The hardwood floors are just another great feature of this home. Call today for your showing appointment.

10751 Millbrook Dr, Chestertown

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

Selling Office: Benson & Mangold, LLC.

$349,900

Quality built and adorable Cape Cod on Private 1 acre mostly wooded lot. 4 bedrooms, 2 full bathrooms. Stainless steel appliances, 2X6 walls, high efficiency heat pump and central a/c system. Nice deck (10'x14') overlooking peaceful back yard and woods. Extra insulated storage in knee walls thru upstairs bedrooms. Close to Rt 213 and Chestertown. No HOA. Owner agent.

4 Beds ⋅ 2 Baths

Quality built and adorable Cape Cod on Private 1 acre mostly wooded lot. 4 bedrooms, 2 full bathrooms. Stainless steel appliances, 2X6 walls, high efficiency heat pump and central a/c system. Nice deck (10'x14') overlooking peaceful back yard and woods. Extra insulated storage in knee walls thru upstairs bedrooms. Close to Rt 213 and Chestertown. No HOA. Owner agent.

26994 Branchtown Rd, Worton

Listing courtesy of Kevin Dey Realty. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

$347,400

“PRICE IMPROVEMENT! Move-in Ready New Construction Rancher in Rock Hall - Perfect for Retirees or Weekend Getaways at 21745 Centennial Lane, Rock Hall, MD, a brand-new 1,415 sq ft home offering single-story living just minutes from marinas, waterfront dining, and all that Rock Hall has to offer. Built by JAC Homes, this 3-bedroom, 2-bath home features an open-concept layout with abundant natural light and durable LVP flooring throughout the main living areas. The kitchen includes granite countertops, quality cabinetry, and tile backsplash, opening seamlessly to the living and dining spaces. The primary bedroom offers a walk-in closet and private en-suite bath with ceramic tile flooring and tiled shower surround. Two additional bedrooms, a full bath, and a dedicated laundry room provide flexible living options. Outdoor features include a 16’ x 12’ composite deck and a covered front porch with stone and masonry details. Additional highlights include an attached one-car garage, blacktop driveway, and a welcoming setting in a growing Rock Hall community. Move-in ready—schedule your showing today.

“PRICE IMPROVEMENT! Move-in Ready New Construction Rancher in Rock Hall - Perfect for Retirees or Weekend Getaways at 21745 Centennial Lane, Rock Hall, MD, a brand-new 1,415 sq ft home offering single-story living just minutes from marinas, waterfront dining, and all that Rock Hall has to offer. Built by JAC Homes, this 3-bedroom, 2-bath home features an open-concept layout with abundant natural light and durable LVP flooring throughout the main living areas. The kitchen includes granite countertops, quality cabinetry, and tile backsplash, opening seamlessly to the living and dining spaces. The primary bedroom offers a walk-in closet and private en-suite bath with ceramic tile flooring and tiled shower surround. Two additional bedrooms, a full bath, and a dedicated laundry room provide flexible living options. Outdoor features include a 16’ x 12’ composite deck and a covered front porch with stone and masonry details. Additional highlights include an attached one-car garage, blacktop driveway, and a welcoming setting in a growing Rock Hall community. Move-in ready—schedule your showing today.

21745 Centennial Ln, Rock Hall

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

Selling Office: Compass.

$344,000

A little different. A lot of possibilities. Live above it. Work below it. Store it all. Come see what you can do with it! This unique property on just over 2 acres in Still Pond offers a rare combination of comfortable living space, an oversized 2-car garage, and plenty of room for the things you enjoy. The 2-bedroom, 1-bath living space sits above the spacious garage, which includes an additional half bath and plenty of room for vehicles, a workshop, equipment, recreational gear, boats, or your next project. Whether you're looking for a full-time home, weekend getaway, hunting retreat, or a place to keep your toys and gear, this property offers flexibility that's hard to find. Enjoy the privacy of 2+ acres while being just a short drive from the Chesapeake Bay and the Eastern Shore's many outdoor recreational opportunities. There may also be potential for additional residential use. Based on information provided regarding the property's zoning, the existing structure may potentially be converted to an accessory dwelling unit (ADU), with the possibility of constructing a separate residential dwelling, subject to applicable requirements, approvals, and a suitable perc/septic system. Buyer to conduct their own due diligence with Kent County and all applicable authorities regarding zoning, permitted uses, ADU conversion, building potential, perc/septic requirements, and future improvements.

2 Beds ⋅ 2 Baths

A little different. A lot of possibilities. Live above it. Work below it. Store it all. Come see what you can do with it! This unique property on just over 2 acres in Still Pond offers a rare combination of comfortable living space, an oversized 2-car garage, and plenty of room for the things you enjoy. The 2-bedroom, 1-bath living space sits above the spacious garage, which includes an additional half bath and plenty of room for vehicles, a workshop, equipment, recreational gear, boats, or your next project. Whether you're looking for a full-time home, weekend getaway, hunting retreat, or a place to keep your toys and gear, this property offers flexibility that's hard to find. Enjoy the privacy of 2+ acres while being just a short drive from the Chesapeake Bay and the Eastern Shore's many outdoor recreational opportunities. There may also be potential for additional residential use. Based on information provided regarding the property's zoning, the existing structure may potentially be converted to an accessory dwelling unit (ADU), with the possibility of constructing a separate residential dwelling, subject to applicable requirements, approvals, and a suitable perc/septic system. Buyer to conduct their own due diligence with Kent County and all applicable authorities regarding zoning, permitted uses, ADU conversion, building potential, perc/septic requirements, and future improvements.

12933 Still Pond Rd, Still Pond

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Douglas Realty LLC.

$340,000

Welcome home to this well-maintained 3-bedroom, 1½-bath brick rancher that combines classic charm with a ready-to-go layout, making it yours to make your own. Nestled in the peaceful countryside just minutes from Chestertown and an easy commute to Middletown, this home offers the best of rural living with open views and fresh country air. Step inside to find a cozy living room, hallway and bedrooms currently carpeted—yet hiding the beautiful original hardwood floors just waiting to be uncovered! The spacious eat-in kitchen offers ample space for family meals, with a sliding glass door that opens to a large screened-in porch—ideal for summer evenings and entertaining. Recent updates include a brand-new roof and a two-year-old HVAC system, offering comfort and peace of mind for years to come. The full basement adds even more versatile space, with one side dedicated to storage and laundry, and the other ideal for hobbies, a workshop, or a playroom. If you're looking for a solid, comfortable home with room to grow and enjoy the country lifestyle, this one is ready for you!

Welcome home to this well-maintained 3-bedroom, 1½-bath brick rancher that combines classic charm with a ready-to-go layout, making it yours to make your own. Nestled in the peaceful countryside just minutes from Chestertown and an easy commute to Middletown, this home offers the best of rural living with open views and fresh country air. Step inside to find a cozy living room, hallway and bedrooms currently carpeted—yet hiding the beautiful original hardwood floors just waiting to be uncovered! The spacious eat-in kitchen offers ample space for family meals, with a sliding glass door that opens to a large screened-in porch—ideal for summer evenings and entertaining. Recent updates include a brand-new roof and a two-year-old HVAC system, offering comfort and peace of mind for years to come. The full basement adds even more versatile space, with one side dedicated to storage and laundry, and the other ideal for hobbies, a workshop, or a playroom. If you're looking for a solid, comfortable home with room to grow and enjoy the country lifestyle, this one is ready for you!

11350 Lynch Rd, Worton

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Allfirst Realty, Inc..

$340,000

Live with ease in this beautifully updated and maintained one floor home in downtown Chestertown. The current owners put a large addition on the house that includes a family room with wood burning stove, sunroom, and primary suite with en suite bathroom and walk in closet. A large laundry room on the main floor and updated kitchen with tons of counter space were other valuable design updates. The basement provides ample partially finished storage space in a completely dry environment due to serious structural improvements, sump pump and french drain system. Bring your hobby down there or your trusty work bench. The roof, HVAC, and hot water heater are all less than 10 years old. The front yard provides a polished experience with tasteful landscaping. The rear yard is quite large for a house in town and includes a raised bed garden and tidy shed. Experience the relaxed lifestyle of Chestertown with the Historic District's shops, Washington College, and the Margo Bailey park just a short walk away.

Live with ease in this beautifully updated and maintained one floor home in downtown Chestertown. The current owners put a large addition on the house that includes a family room with wood burning stove, sunroom, and primary suite with en suite bathroom and walk in closet. A large laundry room on the main floor and updated kitchen with tons of counter space were other valuable design updates. The basement provides ample partially finished storage space in a completely dry environment due to serious structural improvements, sump pump and french drain system. Bring your hobby down there or your trusty work bench. The roof, HVAC, and hot water heater are all less than 10 years old. The front yard provides a polished experience with tasteful landscaping. The rear yard is quite large for a house in town and includes a raised bed garden and tidy shed. Experience the relaxed lifestyle of Chestertown with the Historic District's shops, Washington College, and the Margo Bailey park just a short walk away.

204 Rolling Rd, Chestertown

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

Selling Office: Select Land & Homes, LLC.

$339,900

Selling Office: American Premier Realty, LLC.

103 Flying Cloud Dr, Chestertown

Listing courtesy of American Premier Realty, LLC. Contact:

$339,900

Welcome to “The Cottage,” as it’s affectionately known! This charming home offers beautiful water views of the Chesapeake Bay, creating a peaceful and relaxing place to call home. Inside, you’ll find a bright and inviting layout featuring a Florida Room, a spacious dining room with a cozy fireplace, and two comfortable bedrooms. The large living room is filled with natural light and showcases lovely water views, making it the perfect place to unwind or entertain. Step outside to enjoy the fresh bay breeze from the deck, and take advantage of the storage shed for extra space. The property also includes an enclosed fenced area, ideal for storing tools, trash cans, or outdoor equipment while keeping everything neatly tucked away. Whether you’re looking for a tranquil retreat or a charming year-round residence, The Cottage offers a welcoming atmosphere and scenic surroundings you’ll love coming home to.

2 Beds ⋅ 1 Baths

Welcome to “The Cottage,” as it’s affectionately known! This charming home offers beautiful water views of the Chesapeake Bay, creating a peaceful and relaxing place to call home. Inside, you’ll find a bright and inviting layout featuring a Florida Room, a spacious dining room with a cozy fireplace, and two comfortable bedrooms. The large living room is filled with natural light and showcases lovely water views, making it the perfect place to unwind or entertain. Step outside to enjoy the fresh bay breeze from the deck, and take advantage of the storage shed for extra space. The property also includes an enclosed fenced area, ideal for storing tools, trash cans, or outdoor equipment while keeping everything neatly tucked away. Whether you’re looking for a tranquil retreat or a charming year-round residence, The Cottage offers a welcoming atmosphere and scenic surroundings you’ll love coming home to.

21125 Iowa Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Douglas Realty LLC.

$337,000

Beautifully maintained home in the heart of Rock Hall. Upon entry you'll find an open living space with a cozy gas fireplace and ample natural light. Entertain with ease in the generous open kitchen and dining space, with access to a spacious screened-in porch. Enjoy meals and morning coffee on the serene porch, offering plenty of privacy and views of the woods. Upstairs you'll find the primary bedroom, with a spacious attached bath and walk-in closet. The oversized primary bedroom also has a sitting area that could be used as a home office. Two additional bedrooms upstairs share a second full bath, lots of space for guests and privacy. First-level laundry room, ample pantry storage, half bath, and LVP throughout the first floor. The large attached storage room is perfect for bikes, kayaks, or a small golf cart. The storage room has interior and exterior access. Enjoy a relaxing afternoon on the back porch, morning coffee on the front porch, outside activities in the backyard, or walk to one of the many in-town restaurants! A short distance to the delightful public beach, and several marinas nearby to keep your boat. Come see this one today and get ready for a relaxing Rock Hall lifestyle.

Beautifully maintained home in the heart of Rock Hall. Upon entry you'll find an open living space with a cozy gas fireplace and ample natural light. Entertain with ease in the generous open kitchen and dining space, with access to a spacious screened-in porch. Enjoy meals and morning coffee on the serene porch, offering plenty of privacy and views of the woods. Upstairs you'll find the primary bedroom, with a spacious attached bath and walk-in closet. The oversized primary bedroom also has a sitting area that could be used as a home office. Two additional bedrooms upstairs share a second full bath, lots of space for guests and privacy. First-level laundry room, ample pantry storage, half bath, and LVP throughout the first floor. The large attached storage room is perfect for bikes, kayaks, or a small golf cart. The storage room has interior and exterior access. Enjoy a relaxing afternoon on the back porch, morning coffee on the front porch, outside activities in the backyard, or walk to one of the many in-town restaurants! A short distance to the delightful public beach, and several marinas nearby to keep your boat. Come see this one today and get ready for a relaxing Rock Hall lifestyle.

21122 Striper Run, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

$335,320

AGENTS - PLEASE VIEW AGENT REMARKS IN BRIGHT MLS. This beautifully renovated 3-bedroom, 2-bath Fairlee home is a true gem, perfectly situated on a private 2-acre lot that offers both tranquility and privacy located just a few miles from historic Chestertown . Surrounded by mature trees and bordered by a serene cornfield, this property provides a peaceful retreat from the hustle and bustle of everyday life. The home has been thoughtfully designed to accommodate comfortable everyday living as well as entertaining guests. The spacious rear deck is an ideal spot for hosting gatherings, enjoying morning coffee, or simply relaxing while taking in the natural beauty of the surroundings. Step inside to discover a modernized kitchen equipped with updated appliances and ample counter space, making meal preparation a pleasure. The bathrooms have been tastefully updated to combine style and functionality, while new windows throughout the home allow for plenty of natural light and energy efficiency. Freshly painted interiors and new doors add to the home’s inviting atmosphere, and the newer washer and dryer provide added convenience. Significant system upgrades enhance the home’s comfort and reliability, including a newer HVAC system that ensures efficient heating and cooling year-round. The upgraded BATS septic system offers peace of mind, and the whole-house Puronics water filtration system guarantees clean, fresh water for you and your family. Additionally, a 200 amp service with solar panels, inverter, and 24-7 monitoring have been installed to help reduce electric bills, providing long-term savings and contributing to a more sustainable lifestyle. The oversized 2-car garage features new doors and openers, offering ample space for vehicles and storage. An amazing qnd spacious 23'X24' familyroom with decorative concrete floors off of the garage comes ready for your inspired finishing touches. The possibilities are endless! Pool-table, ping-pong championship, darts. It's got you covered. A Kegerator is there for you and family and friends before you cozy up and watch your favorite movie on the big screen or have a game night. Enter the mud room for a large double-door pantry closet, a seperate washer-dryer area with cabinetry above. Outside, ammenities include a custom Amish Built shed that provides even more storage options for tools, equipment, or outdoor gear. Even the home, garage, and shed have been painted with custom colors that make the newer architectural roof really pop! Located just half a mile from Fairlee Creek, this home offers easy access to boating, fishing, swimming, and other water activities, making it an ideal spot for those who love the outdoors. Experience the best of Eastern Shore living in this exceptional home that combines privacy, modern amenities, and a beautiful natural setting. Whether you’re looking for a peaceful retreat or a place to entertain family and friends, this Fairlee property is ready to welcome you home. Offers may be entered ONLINE through Thursday, July 9, 2026 at 5:00 pm. AT SELLER'S DISCRETION, AN OFFER MAY BE ACCEPTED AT ANY TIME.

AGENTS - PLEASE VIEW AGENT REMARKS IN BRIGHT MLS. This beautifully renovated 3-bedroom, 2-bath Fairlee home is a true gem, perfectly situated on a private 2-acre lot that offers both tranquility and privacy located just a few miles from historic Chestertown . Surrounded by mature trees and bordered by a serene cornfield, this property provides a peaceful retreat from the hustle and bustle of everyday life. The home has been thoughtfully designed to accommodate comfortable everyday living as well as entertaining guests. The spacious rear deck is an ideal spot for hosting gatherings, enjoying morning coffee, or simply relaxing while taking in the natural beauty of the surroundings. Step inside to discover a modernized kitchen equipped with updated appliances and ample counter space, making meal preparation a pleasure. The bathrooms have been tastefully updated to combine style and functionality, while new windows throughout the home allow for plenty of natural light and energy efficiency. Freshly painted interiors and new doors add to the home’s inviting atmosphere, and the newer washer and dryer provide added convenience. Significant system upgrades enhance the home’s comfort and reliability, including a newer HVAC system that ensures efficient heating and cooling year-round. The upgraded BATS septic system offers peace of mind, and the whole-house Puronics water filtration system guarantees clean, fresh water for you and your family. Additionally, a 200 amp service with solar panels, inverter, and 24-7 monitoring have been installed to help reduce electric bills, providing long-term savings and contributing to a more sustainable lifestyle. The oversized 2-car garage features new doors and openers, offering ample space for vehicles and storage. An amazing qnd spacious 23'X24' familyroom with decorative concrete floors off of the garage comes ready for your inspired finishing touches. The possibilities are endless! Pool-table, ping-pong championship, darts. It's got you covered. A Kegerator is there for you and family and friends before you cozy up and watch your favorite movie on the big screen or have a game night. Enter the mud room for a large double-door pantry closet, a seperate washer-dryer area with cabinetry above. Outside, ammenities include a custom Amish Built shed that provides even more storage options for tools, equipment, or outdoor gear. Even the home, garage, and shed have been painted with custom colors that make the newer architectural roof really pop! Located just half a mile from Fairlee Creek, this home offers easy access to boating, fishing, swimming, and other water activities, making it an ideal spot for those who love the outdoors. Experience the best of Eastern Shore living in this exceptional home that combines privacy, modern amenities, and a beautiful natural setting. Whether you’re looking for a peaceful retreat or a place to entertain family and friends, this Fairlee property is ready to welcome you home. Offers may be entered ONLINE through Thursday, July 9, 2026 at 5:00 pm. AT SELLER'S DISCRETION, AN OFFER MAY BE ACCEPTED AT ANY TIME.

22481 Goose Hollow Dr, Chestertown

Listing courtesy of Keller Williams Legacy. Contact:

Selling Office: Samson Properties.

$334,000

Price Improvement = Even More Value! Discover the perfect blend of space, privacy, and comfort at this well-maintained 3-bedroom, 2-bath, 1,900 square foot home, situated on a full acre with public water and sewer, no HOA, and a detached garage with electric! The right wing of the house has two bedrooms and a full bathroom. The left wing has the master bedroom that includes a spacious full bathroom, and walk-in closet. With the recent price change, this property now offers an exceptional opportunity—whether you’re looking for a primary residence, a weekend retreat, or a vacation home on Maryland’s Eastern Shore. The flexible layout and generous acreage make this home ideal for a relaxing getaway, with plenty of room for outdoor entertaining, hobbies, or storing boats, bikes, or recreational gear. Inside, enjoy an open-concept design with easy one-level living—perfect for hosting guests. Outside, a wide blacktop driveway provides ample parking for multiple vehicles, an RV, or a boat. The expansive yard offers space to garden, gather with family and friends, or unwind under the stars after a day on the water or exploring the area. Located just minutes from historic downtown Chestertown, nearby marinas, dining, shopping, and waterfront activities—with convenient access to major routes into Delaware and Pennsylvania—this property offers the ideal balance of peaceful rural living and easy travel. A rare combination of acreage, versatility, and affordability—now at an even better price. Schedule your tour today and see why this home works just as well for everyday living as it does for your Eastern Shore escape. FHA, VA, USDA, and conventional financing welcome!

Price Improvement = Even More Value! Discover the perfect blend of space, privacy, and comfort at this well-maintained 3-bedroom, 2-bath, 1,900 square foot home, situated on a full acre with public water and sewer, no HOA, and a detached garage with electric! The right wing of the house has two bedrooms and a full bathroom. The left wing has the master bedroom that includes a spacious full bathroom, and walk-in closet. With the recent price change, this property now offers an exceptional opportunity—whether you’re looking for a primary residence, a weekend retreat, or a vacation home on Maryland’s Eastern Shore. The flexible layout and generous acreage make this home ideal for a relaxing getaway, with plenty of room for outdoor entertaining, hobbies, or storing boats, bikes, or recreational gear. Inside, enjoy an open-concept design with easy one-level living—perfect for hosting guests. Outside, a wide blacktop driveway provides ample parking for multiple vehicles, an RV, or a boat. The expansive yard offers space to garden, gather with family and friends, or unwind under the stars after a day on the water or exploring the area. Located just minutes from historic downtown Chestertown, nearby marinas, dining, shopping, and waterfront activities—with convenient access to major routes into Delaware and Pennsylvania—this property offers the ideal balance of peaceful rural living and easy travel. A rare combination of acreage, versatility, and affordability—now at an even better price. Schedule your tour today and see why this home works just as well for everyday living as it does for your Eastern Shore escape. FHA, VA, USDA, and conventional financing welcome!

8750 Georgetown Rd, Chestertown

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

Selling Office: EXIT Preferred Realty.

$332,000

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 quartz counters, SS appliances, and a neutral 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. The expansive deck offers views of a private, level lot backing to woods. Chestertown is a quaint, historic district on the Eastern Shore with an avid 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 $12,000 that can be paid off with installments, annually over 15-20 years. PLEASE ENSURE ALL DOORS ARE LOCKED WHEN YOU LEAVE. THERE ARE SEVERAL OTHER HOMES CURRENTLY AVAILABLE AND COMING

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 quartz counters, SS appliances, and a neutral 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. The expansive deck offers views of a private, level lot backing to woods. Chestertown is a quaint, historic district on the Eastern Shore with an avid 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 $12,000 that can be paid off with installments, annually over 15-20 years. PLEASE ENSURE ALL DOORS ARE LOCKED WHEN YOU LEAVE. THERE ARE SEVERAL OTHER HOMES CURRENTLY AVAILABLE AND COMING

11035 Bottom Rd, Worton

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

Selling Office: Coldwell Banker Realty.

$332,000

OPEN HOUSE SATURDAY 3/7/26 FROM 11am-1pm HOPE TO SEE YOU THERE !!! Enjoy easy single-story living in this well-maintained 3-bedroom, 2-bath home situated on a ½-acre lot backing to peaceful farmland. Offering privacy and scenic views, this property blends comfort, space, and thoughtful upgrades throughout. Recent improvements include vinyl siding, a newer roof, and luxury vinyl plank flooring, with original hardwoods underneath for added value and charm. The spacious 12×27 eat-in kitchen is ideal for gatherings and features granite countertops and stainless steel appliances. Both bathrooms are generously sized, with the primary bath showcasing a classic cast iron tub with shower head. A newly added laundry/mudroom enhances everyday convenience and leads directly to a new 14×16 concrete patio and fenced rear yard, perfect for pets, play, or outdoor entertaining. Stay cozy during the colder months with a family room woodstove and warm forced-air heat. The detached two-car garage is topped with a durable 5-year-old metal roof, offering both storage and peace of mind. Town water and sewer add to the home’s practicality. Ideally located between the historic charm of Chestertown and the waterfront town of Rock Hall, this home offers access to quaint shops, fine waterfront dining, boating, hiking and biking trails, the YMCA, and the arts and cultural events of Washington College. A wonderful opportunity to enjoy a simpler lifestyle with a little something for everyone. Approximately 1.5 hour drive to Washington, DC and the Delaware beaches. If this lifestyle is for you, call me to schedule your personal showing.