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Beautifully updated and move-in ready, this charming one-level home offers the perfect blend of comfort, style, and convenience! Recent improvements include a newly added full bath off the living area and a beautifully remodeled half bath featuring a gorgeous walk-in shower and all new finishes The inviting kitchen includes an eat-in dining area, breakfast bar, wine cooler, and brand-new appliances -- ideal for entertaining or everyday living. Gorgeous hardwood floors and attractive tilework throughout add warmth and character. Relax on the enclosed side porch with peaceful neighborhood views or enjoy outdoor living on the newly build deck designed for sunny afternoons and evening gatherings. Located in the heart of Rock Hall, this home places you close to marinas, public landings, local shops, restaurants, and all the charm this beloved Chesapeake Bay town has to offer. Enjoy seasonal festivities, waterfront living, and the laid-back lifestyle Eastern Shore buyers love. Whether you are looking for a full-time residence, weekend getaway or retirement retreat, this lovely home truly feels like HOME!

5989 N Main St, Rock Hall

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

$370,000

Charming and full of potential, this 3-bedroom, 1.5-bath Cape Cod home offers a prime in-town Chestertown location with thoughtful updates already in place. New roof (December 2025), central air unit (2022), and new carpet upstairs provide peace of mind, while classic features like hardwood floors, abundant natural light, and a wood-burning fireplace add warmth and character. The flexible layout includes a main-level bedroom and full bath, a formal dining room, and a bright living room. Upstairs, two additional bedrooms and a half bath, easily converted back to a full, offer room to grow. A bonus room off the main level is perfect for a home office, mudroom expansion, or hobby space. The sunroom connects seamlessly to a private backyard. A sizable driveway and detached garage offer ample off-street parking. Architectural plans for a full renovation and addition are available with an acceptable offer. This is an incredible opportunity to customize and add value in a sought-after location. Just a short stroll to Downtown Chestertown, Washington College, and the Chester River, this home offers both convenience and long-term potential.

Charming and full of potential, this 3-bedroom, 1.5-bath Cape Cod home offers a prime in-town Chestertown location with thoughtful updates already in place. New roof (December 2025), central air unit (2022), and new carpet upstairs provide peace of mind, while classic features like hardwood floors, abundant natural light, and a wood-burning fireplace add warmth and character. The flexible layout includes a main-level bedroom and full bath, a formal dining room, and a bright living room. Upstairs, two additional bedrooms and a half bath, easily converted back to a full, offer room to grow. A bonus room off the main level is perfect for a home office, mudroom expansion, or hobby space. The sunroom connects seamlessly to a private backyard. A sizable driveway and detached garage offer ample off-street parking. Architectural plans for a full renovation and addition are available with an acceptable offer. This is an incredible opportunity to customize and add value in a sought-after location. Just a short stroll to Downtown Chestertown, Washington College, and the Chester River, this home offers both convenience and long-term potential.

217 Philosophers Ter, Chestertown

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

Selling Office: Cross Street Realtors LLC.

$365,000

Well situated 70s Ranch. Original kitchen and baths. Hardwood floors. 3 beds, 2 baths.

Well situated 70s Ranch. Original kitchen and baths. Hardwood floors. 3 beds, 2 baths.

521 N Kent St, Chestertown

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

Selling Office: TTR Sotheby's International Realty.

$365,000

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!

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.

$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.

$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.

$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.

$350,000

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.

$350,000

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..

$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..

$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.

$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.

$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.

Sprawling brick rancher with 2,233 square feet of living space. Hardwood flooring throughout home. Spacious room sizes, partial basement with shelving, attached garage, and lovely setting backing to farmland. Just minutes to route 301 for commuting and shopping in Middletown. Very solid home with great bones and perfectly livable, but does need some updating, priced accordingly to reflect needed repairs, sold AS-IS. Come with an open mind and make this house your home!

4 Beds ⋅ 3 Baths

Sprawling brick rancher with 2,233 square feet of living space. Hardwood flooring throughout home. Spacious room sizes, partial basement with shelving, attached garage, and lovely setting backing to farmland. Just minutes to route 301 for commuting and shopping in Middletown. Very solid home with great bones and perfectly livable, but does need some updating, priced accordingly to reflect needed repairs, sold AS-IS. Come with an open mind and make this house your home!

14021 E Beechwood Rd, Galena

Listing courtesy of Village Real Estate Company LLC. Contact:

Selling Office: Village Real Estate Company LLC.

Bring your vision and transform this unique property into the home of your dreams. Situated on 3.79 picturesque acres, the property features a beautiful one-acre stocked pond, offering a peaceful setting with endless possibilities for outdoor enjoyment. A spacious 40' x 60' outbuilding equipped with three-phase electric provides exceptional flexibility for a workshop, home-based business, storage, agricultural use, or hobby space. A recently installed new roof helps reduce renovation costs and provides a great head start on your restoration project. Whether you're looking to renovate the existing home, create a private country retreat, or capitalize on the property's versatile amenities, this is a rare opportunity with tremendous potential. Property is being sold as-is

Bring your vision and transform this unique property into the home of your dreams. Situated on 3.79 picturesque acres, the property features a beautiful one-acre stocked pond, offering a peaceful setting with endless possibilities for outdoor enjoyment. A spacious 40' x 60' outbuilding equipped with three-phase electric provides exceptional flexibility for a workshop, home-based business, storage, agricultural use, or hobby space. A recently installed new roof helps reduce renovation costs and provides a great head start on your restoration project. Whether you're looking to renovate the existing home, create a private country retreat, or capitalize on the property's versatile amenities, this is a rare opportunity with tremendous potential. Property is being sold as-is

8312 Broad Neck Rd, Chestertown

Listing courtesy of Pearson Smith Realty, LLC. Contact:

Selling Office: LPT Realty, LLC.

11955 Augustine Herman Hwy, Kennedyville

Welcome to this spacious 2,236 square foot, 4-bedroom, 3-bath property located in the heart of Kennedyville, currently configured as a two-unit, multi-use home offering exceptional flexibility. The property can easily be converted back to a single-family 4-bedroom, 3-full-bath residence or utilized as a live/work opportunity with potential storefront space in the front unit while generating rental income from the rear apartment. The rear unit features 2 bedrooms, 2 full bathrooms including a newly added second-floor bath, a full kitchen, laundry, mudroom, and private rear entrance, while the front unit offers 2 bedrooms, 1 full bathroom, a full kitchen, laundry, and a third-floor attic that can easily be converted into additional living space with insulation and electric already roughed in. The owner has completed meticulous structural and mechanical renovations throughout the property, including new plumbing, electrical, HVAC system, roof, insulation, fresh paint, and a newly constructed large full bathroom, ensuring a move-in-ready experience. A fenced rear lot provides parking for up to six vehicles, and the home is certified lead-free. Conveniently located just 10 minutes from Chestertown and 25 minutes from Middletown, the property is also within walking distance to the Kennedyville Firehouse and popular community events such as monthly food truck nights, craft vendor shows, bake sales, and local yard sales.

11955 Augustine Herman Hwy, Kennedyville

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: RE/MAX Chesapeake.

This 2,236 sq ft, 4-bedroom, 3-bath property is a versatile live/work or investment opportunity. Currently configured as a two-unit home, it can easily convert back to a single-family residence or generate rental income from the rear apartment while utilizing the front unit as residential or potential storefront space. Each unit is fully self-contained with its own laundry area (washer/dryer) and full kitchen (refrigerator and stove/cooktop), making them highly desirable for tenants. The rear unit features 2 bedrooms and 2 baths, including a newly added second-floor bath, while the front unit offers 2 bedrooms, 1 bath, and a third-floor attic with insulation and electric roughed in for additional living space. Meticulous renovations include new plumbing, electrical, HVAC, roof, insulation, fresh paint, and a newly constructed full bathroom, ensuring a move-in-ready property. A fenced rear lot provides parking for up to six vehicles, and the home is certified lead-free. Located just 10 minutes from Chestertown and 25 minutes from Middletown, the property is near the Kennedyville Firehouse and local events like food truck nights, craft shows, and yard sales. Strong rental potential combined with turnkey upgrades makes this a smart investment for live/work or multi-family income!

4 Beds ⋅ 3 Baths

This 2,236 sq ft, 4-bedroom, 3-bath property is a versatile live/work or investment opportunity. Currently configured as a two-unit home, it can easily convert back to a single-family residence or generate rental income from the rear apartment while utilizing the front unit as residential or potential storefront space. Each unit is fully self-contained with its own laundry area (washer/dryer) and full kitchen (refrigerator and stove/cooktop), making them highly desirable for tenants. The rear unit features 2 bedrooms and 2 baths, including a newly added second-floor bath, while the front unit offers 2 bedrooms, 1 bath, and a third-floor attic with insulation and electric roughed in for additional living space. Meticulous renovations include new plumbing, electrical, HVAC, roof, insulation, fresh paint, and a newly constructed full bathroom, ensuring a move-in-ready property. A fenced rear lot provides parking for up to six vehicles, and the home is certified lead-free. Located just 10 minutes from Chestertown and 25 minutes from Middletown, the property is near the Kennedyville Firehouse and local events like food truck nights, craft shows, and yard sales. Strong rental potential combined with turnkey upgrades makes this a smart investment for live/work or multi-family income!

11955 Augustine Herman Hwy, Kennedyville

Listing courtesy of Rock Hall Properties Real Estate. Contact:

Selling Office: RE/MAX Chesapeake.

$329,900

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

2 Beds ⋅ 2 Baths

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

10725 Worton Rd, Worton

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

Selling Office: Patterson-Schwartz-Middletown.

$329,000

Offers due Wednesday 4/22 by 6PM! Welcome to this beautifully upgraded 3-bedroom, 2-bath Cape Cod, just six years young and perfectly situated in the sought-after Chesapeake Landing community! Ideally located directly across from the Turtle Trail and Millbrook Pond, you’ll love the peaceful, water-oriented setting with nearby access to a community boat ramp, fishing pier, Worton Creek marina, and new restaurant opening soon. This is far from your typical builder-grade home—the current owners have thoughtfully enhanced every inch. The kitchen truly shines with custom upgrades including a built-in pantry, stunning butcher block countertops, island addition, and bar-top seating—plus a full suite of high-end appliances (yes, even a refrigerator with a large touchscreen!). The flexible floor plan offers the best of both worlds with a dedicated dining room and a first-floor bedroom, ideal for guests or one-level living. Outside, enjoy an extended patio, freshly graded yard, and a new storage shed, creating the perfect outdoor space for relaxing or entertaining. With motivated sellers who have already found their next home, this is an incredible opportunity to move right in and start enjoying all that Chesapeake Landing has to offer. Don’t miss your chance to make it yours!

Offers due Wednesday 4/22 by 6PM! Welcome to this beautifully upgraded 3-bedroom, 2-bath Cape Cod, just six years young and perfectly situated in the sought-after Chesapeake Landing community! Ideally located directly across from the Turtle Trail and Millbrook Pond, you’ll love the peaceful, water-oriented setting with nearby access to a community boat ramp, fishing pier, Worton Creek marina, and new restaurant opening soon. This is far from your typical builder-grade home—the current owners have thoughtfully enhanced every inch. The kitchen truly shines with custom upgrades including a built-in pantry, stunning butcher block countertops, island addition, and bar-top seating—plus a full suite of high-end appliances (yes, even a refrigerator with a large touchscreen!). The flexible floor plan offers the best of both worlds with a dedicated dining room and a first-floor bedroom, ideal for guests or one-level living. Outside, enjoy an extended patio, freshly graded yard, and a new storage shed, creating the perfect outdoor space for relaxing or entertaining. With motivated sellers who have already found their next home, this is an incredible opportunity to move right in and start enjoying all that Chesapeake Landing has to offer. Don’t miss your chance to make it yours!

10594 Millbrook Dr, Chestertown

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

Selling Office: Unrepresented.

Nestled in the charming Rock Hall community, this delightful ranch-style home offers a perfect blend of comfort and convenience. Built in 2006, this well-maintained residence features spacious living space, thoughtfully designed for modern living. The corner lot provides ample outdoor space for gardening, play, or simply enjoying the serene surroundings. Step inside to discover three inviting bedrooms and two full bathrooms, ideal for relaxation and privacy. The open layout encourages a warm flow between living areas, making it perfect for gatherings or quiet evenings at home. The attached front-entry garage and driveway provide convenient parking options, ensuring you and your guests feel right at home. Rock Hall is known for its friendly atmosphere and community spirit with local shops, restaurants, marinas, Ferry Park Beach and the Chesapeake Bay and many more area attractions. This property is not just a house; it's a place where memories are made. With its inviting design and prime location, it offers a wonderful opportunity to embrace a lifestyle of comfort and community. Don't miss your chance to make this charming home your own!

Nestled in the charming Rock Hall community, this delightful ranch-style home offers a perfect blend of comfort and convenience. Built in 2006, this well-maintained residence features spacious living space, thoughtfully designed for modern living. The corner lot provides ample outdoor space for gardening, play, or simply enjoying the serene surroundings. Step inside to discover three inviting bedrooms and two full bathrooms, ideal for relaxation and privacy. The open layout encourages a warm flow between living areas, making it perfect for gatherings or quiet evenings at home. The attached front-entry garage and driveway provide convenient parking options, ensuring you and your guests feel right at home. Rock Hall is known for its friendly atmosphere and community spirit with local shops, restaurants, marinas, Ferry Park Beach and the Chesapeake Bay and many more area attractions. This property is not just a house; it's a place where memories are made. With its inviting design and prime location, it offers a wonderful opportunity to embrace a lifestyle of comfort and community. Don't miss your chance to make this charming home your own!

5925 Williams St, Rock Hall

Listing courtesy of Century 21 Downtown. Contact:

Selling Office: LPT Realty, LLC.

Welcome home to 10572 Watonga Road, a charming Cape Cod nestled on a beautifully wooded corner lot in the desirable Chesapeake Landing community. Built in 2007 and meticulously maintained, this 3-bedroom, 2-bath home offers the perfect blend of comfort, privacy, and Eastern Shore charm. The spacious .35-acre property is surrounded by mature trees, creating peaceful wooded views from both the front and back of the home. Inside, you'll find luxury vinyl plank flooring throughout the main living areas in near-new condition, along with well-maintained carpeting in the bedrooms. Thoughtful updates include a water softener installed in 2024, a fenced yard added just two years ago, French drains, and two sump pumps designed to keep the property draining efficiently. An oversized shed provides excellent storage, while the deck offers the perfect place to enjoy your private outdoor setting. Life in Chesapeake Landing is all about enjoying nature and the water. Residents frequently spot deer, wild turkeys, turtles, and other local wildlife throughout this quiet, established neighborhood. There is no HOA, but the voluntary community association provides access to sought-after water amenities, including a community boat ramp, kayak launch, and fishing pier. The neighborhood also features Mill Brook Pond and the popular Turtle Walking Trail, giving residents even more opportunities to enjoy the outdoors. Located just minutes from historic Chestertown, you'll have easy access to everything that makes Kent County so special. Downtown Chestertown is only about seven minutes away and offers a vibrant year-round farmers market every Saturday from 9 a.m. to noon, locally owned shops, a beloved independent bookstore, and favorite dining destinations like Bad Alfred's Distilling. Also check out the sand bars at the marinas, perfect for waterfront happy hours. Whether you're drawn to the area's marinas, boating opportunities, charming small-town atmosphere, or the spacious homesites that provide room to breathe, this property delivers the true Eastern Shore lifestyle where water access is around every corner and community charm is abundant. If you've been searching for a home that combines modern convenience, natural beauty, and small-town waterfront living, 10572 Watonga Road is ready to welcome you home.

Welcome home to 10572 Watonga Road, a charming Cape Cod nestled on a beautifully wooded corner lot in the desirable Chesapeake Landing community. Built in 2007 and meticulously maintained, this 3-bedroom, 2-bath home offers the perfect blend of comfort, privacy, and Eastern Shore charm. The spacious .35-acre property is surrounded by mature trees, creating peaceful wooded views from both the front and back of the home. Inside, you'll find luxury vinyl plank flooring throughout the main living areas in near-new condition, along with well-maintained carpeting in the bedrooms. Thoughtful updates include a water softener installed in 2024, a fenced yard added just two years ago, French drains, and two sump pumps designed to keep the property draining efficiently. An oversized shed provides excellent storage, while the deck offers the perfect place to enjoy your private outdoor setting. Life in Chesapeake Landing is all about enjoying nature and the water. Residents frequently spot deer, wild turkeys, turtles, and other local wildlife throughout this quiet, established neighborhood. There is no HOA, but the voluntary community association provides access to sought-after water amenities, including a community boat ramp, kayak launch, and fishing pier. The neighborhood also features Mill Brook Pond and the popular Turtle Walking Trail, giving residents even more opportunities to enjoy the outdoors. Located just minutes from historic Chestertown, you'll have easy access to everything that makes Kent County so special. Downtown Chestertown is only about seven minutes away and offers a vibrant year-round farmers market every Saturday from 9 a.m. to noon, locally owned shops, a beloved independent bookstore, and favorite dining destinations like Bad Alfred's Distilling. Also check out the sand bars at the marinas, perfect for waterfront happy hours. Whether you're drawn to the area's marinas, boating opportunities, charming small-town atmosphere, or the spacious homesites that provide room to breathe, this property delivers the true Eastern Shore lifestyle where water access is around every corner and community charm is abundant. If you've been searching for a home that combines modern convenience, natural beauty, and small-town waterfront living, 10572 Watonga Road is ready to welcome you home.

10572 Watonga Rd, Chestertown

Listing courtesy of Serhant. Contact:

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

Selling Office: Chesapeake Real Estate Associates, LLC.

3 Beds ⋅ 1 Baths

202 Valley Rd, Chestertown

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

Price improvement: Colonial in Kennedyville overlooking the pond. Situated on a corner lot with a private driveway behind the house. 2 car attached garage, 4 bedrooms and 2.5 baths. Gas fireplace. Large mudroom with laundry. Partially finished basement with new carpeting. Lovely front porch for relaxing and enjoying the view.

4 Beds ⋅ 3 Baths

Price improvement: Colonial in Kennedyville overlooking the pond. Situated on a corner lot with a private driveway behind the house. 2 car attached garage, 4 bedrooms and 2.5 baths. Gas fireplace. Large mudroom with laundry. Partially finished basement with new carpeting. Lovely front porch for relaxing and enjoying the view.

11942 Flour Mill St, Kennedyville

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

Selling Office: Douglas Realty LLC.

$324,000

Welcome to 102 Flying Cloud a new community known as The Village of Chestertown. This is a rare opportunity to own a home at this price and condition. Designed to with an open 1st floor features a bright white kitchen and dining area open to a large living room for entertaining and a 1/2 bathroom. The 2nd floor features 3 bedrooms 2 full bathrooms. The primary feature private bath and large closet. The exterior has large backyard for friends and family concrete driveway and freshly manicured yard. Call today for private showing today.

Welcome to 102 Flying Cloud a new community known as The Village of Chestertown. This is a rare opportunity to own a home at this price and condition. Designed to with an open 1st floor features a bright white kitchen and dining area open to a large living room for entertaining and a 1/2 bathroom. The 2nd floor features 3 bedrooms 2 full bathrooms. The primary feature private bath and large closet. The exterior has large backyard for friends and family concrete driveway and freshly manicured yard. Call today for private showing today.

102 Flying Cloud Dr, Chestertown

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

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$320,000

Welcome to Chesapeake Landing — where new construction meets timeless Cape Cod charm in the heart of Chestertown, MD. This brand-new 3 BR / 2.5 BA home at 10584 Klamath Rd by Roger Reed Builders (MD Lic. #2464) is move-in ready with quality finishes throughout. The open main level features luxury vinyl plank flooring, white shaker cabinets, granite countertops, a full stainless steel appliance package (side-by-side refrigerator with ice maker, over-range microwave, built-in dishwasher, smooth-surface electric range), and a convenient half bath. The primary suite offers a walk-in closet, ceiling fan, and en suite bath with granite vanity. Two additional bedrooms and a full bath with granite counters round out the upper level. Enjoy the ease of a private well and septic, 2½-ton heat pump, and no HOA. Gravel driveway, vinyl siding, 25-year shingles, and three black exterior lights give great curb appeal. Don't miss your chance to own a brand-new home in one of Kent County's sought-after communities!

Welcome to Chesapeake Landing — where new construction meets timeless Cape Cod charm in the heart of Chestertown, MD. This brand-new 3 BR / 2.5 BA home at 10584 Klamath Rd by Roger Reed Builders (MD Lic. #2464) is move-in ready with quality finishes throughout. The open main level features luxury vinyl plank flooring, white shaker cabinets, granite countertops, a full stainless steel appliance package (side-by-side refrigerator with ice maker, over-range microwave, built-in dishwasher, smooth-surface electric range), and a convenient half bath. The primary suite offers a walk-in closet, ceiling fan, and en suite bath with granite vanity. Two additional bedrooms and a full bath with granite counters round out the upper level. Enjoy the ease of a private well and septic, 2½-ton heat pump, and no HOA. Gravel driveway, vinyl siding, 25-year shingles, and three black exterior lights give great curb appeal. Don't miss your chance to own a brand-new home in one of Kent County's sought-after communities!

10584 Klamath Rd, Chestertown

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

Selling Office: Chesapeake Real Estate Associates, LLC.

11969 Augustine Herman Hwy, Kennedyville

$319,000

Vintage home with lots of original details retained. 3 Staircases, 3 original fireplaces and a very grand front foyer and staircase give this home so much character! Current owners have updated it lovingly throughout. Enter through the spacious back yard, into a welcoming mudroom with a full bath on the main floor to your left and then into the updated and cozy kitchen with new dishwasher, LVP flooring, complete with the cutest back stair case! The staircase leads up to a separate home office, craft room, den, or 4th bedroom. Also downstairs is a main floor bedroom, a nice size dining room with decorative fireplace and parquet flooring, and a Living room with new carpet, and a new pellet stove to keep you warm on those chilly nights. On the 2nd level are 2 bedrooms plus the office, and a full bathroom. Full stairs to the 3rd floor leads to 2 additional rooms that could easily be finished into more living space. Since 2018 the current owners have updated the home to include: New Roof on 2 sections of house and roof repairs to existing roof (only 10 years old), all New windows (5) on third floor, encapsulated crawl space, new Oil Furnace, 2 new water heaters (one serves upstairs bathroom only). New dishwasher, blown in insulation in all internal ceilings and attic, new flooring downstairs, kitchen and bathroom updates, and so much more! Outside is a very private oasis. Completely fenced in yard with large covered side porch and open back deck looking out to a manicured lawn with large shed and nice plantings. Back gate leads to gravel driveway, parking for 2-4 cars The home is very versitile. Village zoning allows for commercial use as well. In the past it has been an antique/retail store, but please verify any possible uses with the county first.

4 Beds ⋅ 2 Baths

Vintage home with lots of original details retained. 3 Staircases, 3 original fireplaces and a very grand front foyer and staircase give this home so much character! Current owners have updated it lovingly throughout. Enter through the spacious back yard, into a welcoming mudroom with a full bath on the main floor to your left and then into the updated and cozy kitchen with new dishwasher, LVP flooring, complete with the cutest back stair case! The staircase leads up to a separate home office, craft room, den, or 4th bedroom. Also downstairs is a main floor bedroom, a nice size dining room with decorative fireplace and parquet flooring, and a Living room with new carpet, and a new pellet stove to keep you warm on those chilly nights. On the 2nd level are 2 bedrooms plus the office, and a full bathroom. Full stairs to the 3rd floor leads to 2 additional rooms that could easily be finished into more living space. Since 2018 the current owners have updated the home to include: New Roof on 2 sections of house and roof repairs to existing roof (only 10 years old), all New windows (5) on third floor, encapsulated crawl space, new Oil Furnace, 2 new water heaters (one serves upstairs bathroom only). New dishwasher, blown in insulation in all internal ceilings and attic, new flooring downstairs, kitchen and bathroom updates, and so much more! Outside is a very private oasis. Completely fenced in yard with large covered side porch and open back deck looking out to a manicured lawn with large shed and nice plantings. Back gate leads to gravel driveway, parking for 2-4 cars The home is very versitile. Village zoning allows for commercial use as well. In the past it has been an antique/retail store, but please verify any possible uses with the county first.

11969 Augustine Herman Hwy, Kennedyville

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

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

$318,000

Charming Single-Level Home in the Heart of Walkable Chestertown. Welcome to one of Chestertown's most convenient addresses — a quaint, single-level, three-bedroom home set on a large, shaded yard just a few flat blocks from Downtown Chestertown, Washington College, the weekly farmers market, the town's annual festivals, locally loved restaurants, and everyday groceries. The location is the kind that sells itself: leave the car in the driveway and run the day on foot, from morning coffee downtown to an evening stroll after the festivals. Inside, the sun-filled sunroom anchors the home with year-round natural light and a flexible layout that adapts to how you actually live. Use it as a quiet reading nook, a bright home office, an art studio, or simply a place to begin and end each day. The three-bedroom, single-level floor plan delivers true main-level living with no stairs and no wasted square footage, an increasingly rare find in historic Chestertown. The HVAC has been recently updated, providing year-round comfort, modern efficiency, and predictable utility costs for new owners. Step outside to a generous, tree-shaded yard offering a level of privacy and outdoor space uncommon to a home this close to downtown. There's room to garden, host family dinners, let pets roam, or simply enjoy a quiet afternoon in the shade. The setting feels tucked away while the rest of the town is just a short walk from your front door. For weekend owners, the home offers true lock-and-leave simplicity. For full-time residents, it offers the daily rhythm of a small college town with a real cultural calendar, a thriving farmers market, and a walkable downtown filled with independent shops and restaurants. Fiber optic internet is available at the property, supporting fast, reliable connectivity for remote work, streaming, and study without compromise. Single-level, move-in ready, and walkable to it all — a rare combination in this small, storybook college town. The home suits a wide range of buyers, from first-time homeowners and downsizers to weekend retreat owners and anyone seeking a quieter life with genuine connection to community. Schedule your private tour today!