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117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006168 ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

3 Beds ⋅ 3 Baths

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006168 ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

117 Water St N Unit 1A, Chestertown

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

$679,900

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

3 Beds ⋅ 4 Baths

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

8986 Orchard Dr, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

$675,000

This charming American Four Square has been meticulously maintained and is located 1 block from Washington College’s campus and near Chestertown’s Historic District’s shops and restaurants. All of the key features of this architectural style are evident - two and a half stories high, hipped slate roof with a distinctive dormer at the front of the house, spacious four-room plan and full front porch with mahogany flooring with a depth that makes it a wonderful outdoor room. The American Four-Square was designed for narrow urban lots and this property’s bonus is its deep lot that easily accommodated an addition of a kitchen-family room opening onto a deck and a deep rear fully fenced back yard that offers safe play for children and pets. Another bonus is a two-car garage. From the foyer, the “U” shaped artisan stair rises to the third floor and the main floor’s living room, dining room, bathroom and library are seamlessly connected to maximize the rooms’ sizes. The rear addition of an open plan kitchen-family room has easy indoor-outdoor flow to the adjacent deck. The second floor contains 3 bedrooms and 2 full baths as well as the laundry. The third floor contains two additional bedrooms. Throughout the house, details of original wood floors, moldings and trim, corner guards and bespoke millwork evoke an earlier era of gracious living. A uniquely American architectural style, with an addition and updates for today’s family lifestyle; freshly painted exterior, meticulous mature landscaping, fenced rear yard that is a verdant oasis, two-car garage - who could ask for anything more?

5 Beds ⋅ 3 Baths

This charming American Four Square has been meticulously maintained and is located 1 block from Washington College’s campus and near Chestertown’s Historic District’s shops and restaurants. All of the key features of this architectural style are evident - two and a half stories high, hipped slate roof with a distinctive dormer at the front of the house, spacious four-room plan and full front porch with mahogany flooring with a depth that makes it a wonderful outdoor room. The American Four-Square was designed for narrow urban lots and this property’s bonus is its deep lot that easily accommodated an addition of a kitchen-family room opening onto a deck and a deep rear fully fenced back yard that offers safe play for children and pets. Another bonus is a two-car garage. From the foyer, the “U” shaped artisan stair rises to the third floor and the main floor’s living room, dining room, bathroom and library are seamlessly connected to maximize the rooms’ sizes. The rear addition of an open plan kitchen-family room has easy indoor-outdoor flow to the adjacent deck. The second floor contains 3 bedrooms and 2 full baths as well as the laundry. The third floor contains two additional bedrooms. Throughout the house, details of original wood floors, moldings and trim, corner guards and bespoke millwork evoke an earlier era of gracious living. A uniquely American architectural style, with an addition and updates for today’s family lifestyle; freshly painted exterior, meticulous mature landscaping, fenced rear yard that is a verdant oasis, two-car garage - who could ask for anything more?

212 Washington Ave, Chestertown

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

$635,000

Buildable waterfront lot in the Chester River Landing community. This prime location captures panoramic views of the Chester River! Just steps away from deep water boat slips, which are available for lease or purchase. Perfect location to build your dream home on the water. The Chester River Landing community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club. Enjoy the close proximity to ample shops, dining options, and Chestertown’s year-round farmers market.

108 Little Harbor Way, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$549,900

Opportunities like this don't come along every day! Welcome to 329 Union Church Road, tucked away in a highly sought-after neighborhood in Queen Anne’s County where homes rarely become available.—a home with plenty of space, useful updates, and room to truly make it your own! Situated on just over an acre, this 4-bedroom, 2.5-bath home offers 2,464 square feet of living space, a paved driveway, attached garage, and a large detached pole barn with loft—providing plenty of room for storage, hobbies, a workshop, or all the extras. Inside, you’ll find a spacious and functional layout ready for its next owners to settle in and make it feel like home. The kitchen features updated appliances, including a new refrigerator, new stove, microwave, oven, and dishwasher in 2026, while new LVP flooring upstairs adds a fresh look. All toilets throughout the home have also been replaced. Major mechanical updates include the upstairs HVAC system replaced in 2023 and the downstairs HVAC system replaced in 2026. The crawlspace has also been professionally serviced by DriGuys Restoration, including the installation of a new vapor barrier. The completed work comes with a transferable one-year warranty, providing additional peace of mind for the next owners. Outside, the 1.03-acre property gives you room to spread out, enjoy the outdoors, and create a space that fits the way you want to live. The detached pole barn adds even more versatility, while the attached and detached garage spaces provide plenty of options for parking, storage, projects, and more. Additional features include a tankless gas water heater, private well and septic, and an owned water-filtration system. Whether you’re looking for more room inside, space for your hobbies and projects, or simply a place you can put your own stamp on, 329 Union Church Road offers the space and flexibility to make it your own. Come take a look and imagine making this Queen Anne’s County property your next home!

4 Beds ⋅ 3 Baths

Opportunities like this don't come along every day! Welcome to 329 Union Church Road, tucked away in a highly sought-after neighborhood in Queen Anne’s County where homes rarely become available.—a home with plenty of space, useful updates, and room to truly make it your own! Situated on just over an acre, this 4-bedroom, 2.5-bath home offers 2,464 square feet of living space, a paved driveway, attached garage, and a large detached pole barn with loft—providing plenty of room for storage, hobbies, a workshop, or all the extras. Inside, you’ll find a spacious and functional layout ready for its next owners to settle in and make it feel like home. The kitchen features updated appliances, including a new refrigerator, new stove, microwave, oven, and dishwasher in 2026, while new LVP flooring upstairs adds a fresh look. All toilets throughout the home have also been replaced. Major mechanical updates include the upstairs HVAC system replaced in 2023 and the downstairs HVAC system replaced in 2026. The crawlspace has also been professionally serviced by DriGuys Restoration, including the installation of a new vapor barrier. The completed work comes with a transferable one-year warranty, providing additional peace of mind for the next owners. Outside, the 1.03-acre property gives you room to spread out, enjoy the outdoors, and create a space that fits the way you want to live. The detached pole barn adds even more versatility, while the attached and detached garage spaces provide plenty of options for parking, storage, projects, and more. Additional features include a tankless gas water heater, private well and septic, and an owned water-filtration system. Whether you’re looking for more room inside, space for your hobbies and projects, or simply a place you can put your own stamp on, 329 Union Church Road offers the space and flexibility to make it your own. Come take a look and imagine making this Queen Anne’s County property your next home!

329 Union Church Rd, Chestertown

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

$525,000

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

3 Beds ⋅ 3 Baths

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

8901 S Bayview Dr, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$519,900

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

3 Beds ⋅ 3 Baths

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

7655 James Ln, Chestertown

Listing courtesy of RE/MAX Advantage Realty. Contact:

$509,000

103 Sutton is perfectly situated just a stone’s throw from the vibrant heart of Downtown Chestertown. This exquisite 4+ bedroom residence is designed to cater to the diverse needs of today’s Buyers, offering a harmonious blend of comfort, style, and functionality. This home is ideal for those upsizing or seeking multi-generational living. * Originally built as the community model home – and meticulously maintained since – it has ALL the extras: generous breakfast nook bump out, gas fireplace, gleaming hardwood floors, upgraded carpet, oversized windows, granite countertops, stainless appliances, dedicated home office, and a finished basement with a full bath and expansive wet bar. * As you step inside, you’ll be greeted by a two-story foyer flooded with light, dining room and den or family room. The gourmet kitchen that is a chef’s paradise, featuring high-end appliances, custom hardwood cabinetry, and a small island for an ideal triangle of space for meal prep. The open concept layout flows effortlessly into the breakfast nook and living room, providing the perfect setting for family gatherings and celebrations with friends. Click on the propane fireplace for a cozy night watching the sunset or snow flurries outside the tall windows. * The spacious primary suite is an escape through a double door entry – featuring a lighted tray ceiling, a large walk-in closet, en suite bath with soaking tub, glass shower, and a separate water closet. Three additional bedrooms all have custom trim work, generous closets, and large windows. * The finished basement is a standout feature, complete with a stylish wet bar with stone walls that transforms it into the ultimate entertainment zone, perfect for hosting game nights or movie marathons. The backyard feels private with mature trees and a gentle slope, ideal for play space. * The proximity to local parks, playgrounds, restaurants, and shopping ensures that all your family’s needs are met within minutes. Additionally, the Coventry Farms neighborhood fosters a sense of community all while being a convenient distance from Middletown, DE, Philadelphia, PA, Washington DC, Baltimore, MD, and points beyond. * This home is not just a place to live; it’s a lifestyle waiting to be embraced. Don’t miss the opportunity to make this stunning property your own. Schedule your private tour today and experience firsthand what this exceptional home has to offer.

5 Beds ⋅ 4 Baths

103 Sutton is perfectly situated just a stone’s throw from the vibrant heart of Downtown Chestertown. This exquisite 4+ bedroom residence is designed to cater to the diverse needs of today’s Buyers, offering a harmonious blend of comfort, style, and functionality. This home is ideal for those upsizing or seeking multi-generational living. * Originally built as the community model home – and meticulously maintained since – it has ALL the extras: generous breakfast nook bump out, gas fireplace, gleaming hardwood floors, upgraded carpet, oversized windows, granite countertops, stainless appliances, dedicated home office, and a finished basement with a full bath and expansive wet bar. * As you step inside, you’ll be greeted by a two-story foyer flooded with light, dining room and den or family room. The gourmet kitchen that is a chef’s paradise, featuring high-end appliances, custom hardwood cabinetry, and a small island for an ideal triangle of space for meal prep. The open concept layout flows effortlessly into the breakfast nook and living room, providing the perfect setting for family gatherings and celebrations with friends. Click on the propane fireplace for a cozy night watching the sunset or snow flurries outside the tall windows. * The spacious primary suite is an escape through a double door entry – featuring a lighted tray ceiling, a large walk-in closet, en suite bath with soaking tub, glass shower, and a separate water closet. Three additional bedrooms all have custom trim work, generous closets, and large windows. * The finished basement is a standout feature, complete with a stylish wet bar with stone walls that transforms it into the ultimate entertainment zone, perfect for hosting game nights or movie marathons. The backyard feels private with mature trees and a gentle slope, ideal for play space. * The proximity to local parks, playgrounds, restaurants, and shopping ensures that all your family’s needs are met within minutes. Additionally, the Coventry Farms neighborhood fosters a sense of community all while being a convenient distance from Middletown, DE, Philadelphia, PA, Washington DC, Baltimore, MD, and points beyond. * This home is not just a place to live; it’s a lifestyle waiting to be embraced. Don’t miss the opportunity to make this stunning property your own. Schedule your private tour today and experience firsthand what this exceptional home has to offer.

103 Sutton Way, Chestertown

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

$500,000

A great opportunity for community mission driven organizations. The church and 5 additional parcels are all offered separately or together. Located in the heart of Chestertown, this charming church of a little over 3,500 square feet offers a unique opportunity for continued use as a place of worship, community gathering space, or potential conversion. The property features wheelchair accessibility, on-site parking, and a layout ideal for a variety of uses. With its peaceful setting and classic structure, this building is ready to serve its next purpose. Also available with mls MDKE2006846 additionally

201 N Lynchburg St, Chestertown

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

$495,000

Beautiful waterviews of the Chester River set the stage for this special Chestertown property, located in desirable Mile Tree Village and just a short walk from the Historic District. Set on .53 acres, the home offers 1,656 square feet of finished living space on the main level, with 3 bedrooms and 2 full baths, plus an unfinished lower level with a half bath and one-and-a-half-car garage. An upper-level deck, accessible from the living room, dining room, and primary suite, provides the perfect spot to enjoy the river views and the easy Eastern Shore lifestyle. The home is ready for a fresh vision and offers tremendous potential to become a luxury waterview residence. Thoughtful updating could transform the existing spaces into a home that takes full advantage of the setting. Within a short walk or bike ride to Chestertown's Historic District for dinner, shopping, galleries, and Annual Festivals, while the Chester River provides a beautiful backdrop to everyday life. Bring your vision and create a truly special waterview home and experience the Eastern Shore Lifestyle at its finest!

3 Beds ⋅ 3 Baths

Beautiful waterviews of the Chester River set the stage for this special Chestertown property, located in desirable Mile Tree Village and just a short walk from the Historic District. Set on .53 acres, the home offers 1,656 square feet of finished living space on the main level, with 3 bedrooms and 2 full baths, plus an unfinished lower level with a half bath and one-and-a-half-car garage. An upper-level deck, accessible from the living room, dining room, and primary suite, provides the perfect spot to enjoy the river views and the easy Eastern Shore lifestyle. The home is ready for a fresh vision and offers tremendous potential to become a luxury waterview residence. Thoughtful updating could transform the existing spaces into a home that takes full advantage of the setting. Within a short walk or bike ride to Chestertown's Historic District for dinner, shopping, galleries, and Annual Festivals, while the Chester River provides a beautiful backdrop to everyday life. Bring your vision and create a truly special waterview home and experience the Eastern Shore Lifestyle at its finest!

10 Cedar Chase Ct, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

$480,000

PICTURES COMING SOON Welcome home to this beautiful 3-bedroom, 2.5-bath residence in the charming town of Chestertown, MD. Designed for both comfortable living and effortless entertaining, this home offers spacious interiors filled with abundant natural light. The main level features a bright kitchen with Breakfast Bar that flows seamlessly into a sunny Florida room, creating the perfect space to enjoy your morning coffee or unwind while overlooking the backyard. You'll also find a formal dining room for hosting special occasions, a welcoming living room, and a cozy family room that provides plenty of space for everyday living. Downstairs, the finished basement offers versatile additional living space ideal for a recreation room, home theater, fitness area, playroom, or home office. There is enough space to do all of it. The unfinished area has full laundry and ample storage. Upstairs, the expansive owner's suite serves as a private retreat, complete with a generous walk-in closet and an ensuite bathroom featuring a soaking tub. Two additional bedrooms each offer large closets and ample space for family, guests, or a home office. A full bathroom conveniently located off the second-floor sitting area completes the upper level. Step outside to your own private backyard oasis. The landscaped yard features a refreshing in-ground swimming pool with a new tile finish and a new filtration system, making it ready for years of enjoyment. A new deck with a privacy wall extends from the home, providing the perfect setting for outdoor dining, entertaining, or relaxing poolside. Additional highlights include a large storage shed and a newly installed rock bed surrounding the pool deck that enhances both beauty and low-maintenance landscaping. For added peace of mind, the home also features a roof that is only two years old. Combining spacious living areas, thoughtful updates, exceptional outdoor amenities, and a desirable location in historic Chestertown, this home truly has something for everyone. Don't miss the opportunity to make this exceptional property your next home!

3 Beds ⋅ 3 Baths

PICTURES COMING SOON Welcome home to this beautiful 3-bedroom, 2.5-bath residence in the charming town of Chestertown, MD. Designed for both comfortable living and effortless entertaining, this home offers spacious interiors filled with abundant natural light. The main level features a bright kitchen with Breakfast Bar that flows seamlessly into a sunny Florida room, creating the perfect space to enjoy your morning coffee or unwind while overlooking the backyard. You'll also find a formal dining room for hosting special occasions, a welcoming living room, and a cozy family room that provides plenty of space for everyday living. Downstairs, the finished basement offers versatile additional living space ideal for a recreation room, home theater, fitness area, playroom, or home office. There is enough space to do all of it. The unfinished area has full laundry and ample storage. Upstairs, the expansive owner's suite serves as a private retreat, complete with a generous walk-in closet and an ensuite bathroom featuring a soaking tub. Two additional bedrooms each offer large closets and ample space for family, guests, or a home office. A full bathroom conveniently located off the second-floor sitting area completes the upper level. Step outside to your own private backyard oasis. The landscaped yard features a refreshing in-ground swimming pool with a new tile finish and a new filtration system, making it ready for years of enjoyment. A new deck with a privacy wall extends from the home, providing the perfect setting for outdoor dining, entertaining, or relaxing poolside. Additional highlights include a large storage shed and a newly installed rock bed surrounding the pool deck that enhances both beauty and low-maintenance landscaping. For added peace of mind, the home also features a roof that is only two years old. Combining spacious living areas, thoughtful updates, exceptional outdoor amenities, and a desirable location in historic Chestertown, this home truly has something for everyone. Don't miss the opportunity to make this exceptional property your next home!

129 Trafford Dr, Chestertown

Listing courtesy of Elevated Real Estate Solutions. Contact:

$429,500

Seller is offering a credit of up to 2% of the purchase price toward the buyer's interest rate buydown with an acceptable offer, a real financial advantage on this updated Cape Cod in the Chesapeake Landing community. Buydown subject to lender approval and buyer qualification. Welcome home to relaxed Eastern Shore living in the waterfront community of Chesapeake Landing. This beautifully updated 2,140 sq ft Cape Cod offers the perfect blend of charm and modern comfort with 3 bedrooms, 2.5 baths, and a welcoming floor plan designed for everyday life. The main level features new flooring throughout, a spacious living area, formal dining room, and a renovated country kitchen with new appliances, new counters, and plenty of space for gathering. A main-level bedroom adds flexibility for guests or one-level living. Enjoy morning coffee or evening sunsets on the back deck overlooking the open, cleared 0.39-acre lot—perfect for gardening or outdoor fun. Additional highlights include a 2-car garage and access to community amenities with a beach, fishing pier, and pavilion. Just minutes from historic downtown Chestertown, you’ll love being close to local shops, dining, marinas, and all the charm of Eastern Shore living.

4 Beds ⋅ 3 Baths

Seller is offering a credit of up to 2% of the purchase price toward the buyer's interest rate buydown with an acceptable offer, a real financial advantage on this updated Cape Cod in the Chesapeake Landing community. Buydown subject to lender approval and buyer qualification. Welcome home to relaxed Eastern Shore living in the waterfront community of Chesapeake Landing. This beautifully updated 2,140 sq ft Cape Cod offers the perfect blend of charm and modern comfort with 3 bedrooms, 2.5 baths, and a welcoming floor plan designed for everyday life. The main level features new flooring throughout, a spacious living area, formal dining room, and a renovated country kitchen with new appliances, new counters, and plenty of space for gathering. A main-level bedroom adds flexibility for guests or one-level living. Enjoy morning coffee or evening sunsets on the back deck overlooking the open, cleared 0.39-acre lot—perfect for gardening or outdoor fun. Additional highlights include a 2-car garage and access to community amenities with a beach, fishing pier, and pavilion. Just minutes from historic downtown Chestertown, you’ll love being close to local shops, dining, marinas, and all the charm of Eastern Shore living.

10781 Fermoy Rd, Chestertown

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

$425,000

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

4 Beds ⋅ 3 Baths

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

106 Harlan Loop, Chestertown

Listing courtesy of Douglas Realty LLC. Contact:

$400,000

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

2 Beds ⋅ 2 Baths

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

21338 Virginia Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$399,900

Welcome to 8630 Elm Road, where comfortable living meets the relaxed pace of Maryland’s Eastern Shore. Located in the water-oriented Tolchester Estates community, this refreshed five-bedroom, 2.5-bath home offers approximately 1,936 square feet of flexible living space on about 0.38 acres. Begin the day with a quiet moment on the furnished front porch, then enjoy a versatile interior with room to work from home, welcome overnight guests, and spend time together. The fifth bedroom can serve as a private home office, guest room, hobby room, or other flexible space separate from the main living area. Attractive ceiling fans throughout the home add comfort and style. The refreshed kitchen features bright white cabinetry, a French-door refrigerator, stainless-steel appliances, and a spacious adjoining dining area with room to gather and enjoy meals. The main living ar Start the day with a quiet moment on the furnished front porch, then enjoy a layout with room to work from home, welcome guests, and spend time together. The fifth bedroom can serve as a home office separate from the main living area, a guest room, or a hobby space. Attractive ceiling fans throughout the home add both comfort and style. The updated kitchen features bright white cabinetry, a French-door refrigerator, and stainless-steel appliances. A new white porcelain herringbone backsplash is scheduled for installation on October 8. The spacious kitchen and dining area offer room to gather and enjoy a meal. The main living area is anchored by a stylish electric fireplace with custom floating shelving, creating a warm focal point for the home. Adjustable fireplace settings add to the cozy atmosphere. Step outside to the expanded deck, unwind in the hot tub, or gather around the fire pit. Imagine sharing hot chocolate and s’mores on a crisp fall evening, or taking a quiet moment to enjoy the setting and watch for local wildlife. Boating enthusiasts will appreciate the nearby seasonal marina, with restaurants and a dive bar about three blocks away, and a public boat ramp approximately one mile away, providing convenient access to the area’s waterways. The expansive driveway offers parking for up to eight vehicles, with room for multiple cars, larger vehicles, and weekend guests. The partially finished one-car garage can become a game room, hobby area, home gym, or extra gathering space. Additional features include an approximately two-year-old water heater and a private well with a water-treatment and softening system, professionally serviced in 2025 with a new Clack neutralizer head installed. Furnishings throughout the home, including the porch furniture, are included. Though built in 2006, the home has been gently enjoyed primarily as a second home or vacation getaway and has received updates and improvements, including stainless-steel appliances, a built-in electric fireplace, and the newer water heater. This home could be a great fit if you’re: Looking for a second home or vacation getaway you can enjoy yourself and explore renting part-time when you’re away. Looking for an investment property with a history of income from both traditional and short-term rentals. Certain loan programs may consider rental income when evaluating an investment property; eligibility depends on lender guidelines. Looking for a primary residence with flexible living space and convenient access to the marina. Preferred Lender Credit: Eligible buyers may receive a lender credit when using the preferred lender. Financing programs and credits are subject to eligibility, underwriting, and lender approval. Whether you’re looking for a primary residence, a weekend retreat, or a home designed for entertaining, 8630 Elm Road offers space, versatility, thoughtful updates, and the Eastern Shore lifestyle in one inviting package. Ready to see it in person? Schedule your private showing today through the listing’s appointment link!

5 Beds ⋅ 3 Baths

Welcome to 8630 Elm Road, where comfortable living meets the relaxed pace of Maryland’s Eastern Shore. Located in the water-oriented Tolchester Estates community, this refreshed five-bedroom, 2.5-bath home offers approximately 1,936 square feet of flexible living space on about 0.38 acres. Begin the day with a quiet moment on the furnished front porch, then enjoy a versatile interior with room to work from home, welcome overnight guests, and spend time together. The fifth bedroom can serve as a private home office, guest room, hobby room, or other flexible space separate from the main living area. Attractive ceiling fans throughout the home add comfort and style. The refreshed kitchen features bright white cabinetry, a French-door refrigerator, stainless-steel appliances, and a spacious adjoining dining area with room to gather and enjoy meals. The main living ar Start the day with a quiet moment on the furnished front porch, then enjoy a layout with room to work from home, welcome guests, and spend time together. The fifth bedroom can serve as a home office separate from the main living area, a guest room, or a hobby space. Attractive ceiling fans throughout the home add both comfort and style. The updated kitchen features bright white cabinetry, a French-door refrigerator, and stainless-steel appliances. A new white porcelain herringbone backsplash is scheduled for installation on October 8. The spacious kitchen and dining area offer room to gather and enjoy a meal. The main living area is anchored by a stylish electric fireplace with custom floating shelving, creating a warm focal point for the home. Adjustable fireplace settings add to the cozy atmosphere. Step outside to the expanded deck, unwind in the hot tub, or gather around the fire pit. Imagine sharing hot chocolate and s’mores on a crisp fall evening, or taking a quiet moment to enjoy the setting and watch for local wildlife. Boating enthusiasts will appreciate the nearby seasonal marina, with restaurants and a dive bar about three blocks away, and a public boat ramp approximately one mile away, providing convenient access to the area’s waterways. The expansive driveway offers parking for up to eight vehicles, with room for multiple cars, larger vehicles, and weekend guests. The partially finished one-car garage can become a game room, hobby area, home gym, or extra gathering space. Additional features include an approximately two-year-old water heater and a private well with a water-treatment and softening system, professionally serviced in 2025 with a new Clack neutralizer head installed. Furnishings throughout the home, including the porch furniture, are included. Though built in 2006, the home has been gently enjoyed primarily as a second home or vacation getaway and has received updates and improvements, including stainless-steel appliances, a built-in electric fireplace, and the newer water heater. This home could be a great fit if you’re: Looking for a second home or vacation getaway you can enjoy yourself and explore renting part-time when you’re away. Looking for an investment property with a history of income from both traditional and short-term rentals. Certain loan programs may consider rental income when evaluating an investment property; eligibility depends on lender guidelines. Looking for a primary residence with flexible living space and convenient access to the marina. Preferred Lender Credit: Eligible buyers may receive a lender credit when using the preferred lender. Financing programs and credits are subject to eligibility, underwriting, and lender approval. Whether you’re looking for a primary residence, a weekend retreat, or a home designed for entertaining, 8630 Elm Road offers space, versatility, thoughtful updates, and the Eastern Shore lifestyle in one inviting package. Ready to see it in person? Schedule your private showing today through the listing’s appointment link!

8630 Elm Rd, Chestertown

Listing courtesy of Save 6, Incorporated. Contact:

$385,000

Located in the small Eastern Shore town of Fairlee, this spacious Bi-level sits on 1.65 acres of cleared land, just a short 10-minute drive to both Chestertown and Rock Hall. The home offers 3 bedrooms and 2 bathrooms, with a finished lower level for additional living space. A large sunroom with cathedral ceilings and walls of windows is the heart of the home, filling the space with natural light. Enjoy cooking in the updated kitchen with stainless steel appliances and serving meals in the separate dining room. Outdoor living is a highlight with an enclosed back porch, decks on both the first and second floors, and plenty of open yard space. Additional features include two fireplaces, a dedicated laundry room, and a shed for storage. A detached 3-bay garage provides ample room for vehicles, hobbies, or workshop space. This property combines comfortable living with generous space inside and out, all in a convenient location close to towns and the water.

4 Beds ⋅ 3 Baths

Located in the small Eastern Shore town of Fairlee, this spacious Bi-level sits on 1.65 acres of cleared land, just a short 10-minute drive to both Chestertown and Rock Hall. The home offers 3 bedrooms and 2 bathrooms, with a finished lower level for additional living space. A large sunroom with cathedral ceilings and walls of windows is the heart of the home, filling the space with natural light. Enjoy cooking in the updated kitchen with stainless steel appliances and serving meals in the separate dining room. Outdoor living is a highlight with an enclosed back porch, decks on both the first and second floors, and plenty of open yard space. Additional features include two fireplaces, a dedicated laundry room, and a shed for storage. A detached 3-bay garage provides ample room for vehicles, hobbies, or workshop space. This property combines comfortable living with generous space inside and out, all in a convenient location close to towns and the water.

23043 Bay Shore Spur, Chestertown

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$375,000

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

2 Beds ⋅ 1 Baths

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

117 Water St N Unit 2A, Chestertown

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

$370,000

Space, convenience, and value just minutes from downtown Chestertown! This spacious 4-bedroom, 2.5-bath Colonial in Coventry Farms checks the boxes for buyers looking for room to spread out without giving up convenience. The main level features a comfortable living room, dining area, kitchen, and half bath. Upstairs, you’ll find four bedrooms, including a spacious primary suite with a walk-in closet and en suite bath with dual vanities. Need even more space? The mostly finished basement adds approximately 600 sq. ft. of flexible living space. Plus the attached two car garage with plenty of room to park your vehicle and still have storage space. Outside, enjoy a stamped-concrete patio and fenced backyard—perfect for relaxing and entertaining. Recent updates include HVAC replaced in 2021, upgraded bathrooms, and additional cabinets and counter space in the kitchen. Just under 2 miles from historic downtown Chestertown, you’ll be close to restaurants, shopping, festivals, walking trail, the waterfront park, and everything town has to offer.

4 Beds ⋅ 3 Baths

Space, convenience, and value just minutes from downtown Chestertown! This spacious 4-bedroom, 2.5-bath Colonial in Coventry Farms checks the boxes for buyers looking for room to spread out without giving up convenience. The main level features a comfortable living room, dining area, kitchen, and half bath. Upstairs, you’ll find four bedrooms, including a spacious primary suite with a walk-in closet and en suite bath with dual vanities. Need even more space? The mostly finished basement adds approximately 600 sq. ft. of flexible living space. Plus the attached two car garage with plenty of room to park your vehicle and still have storage space. Outside, enjoy a stamped-concrete patio and fenced backyard—perfect for relaxing and entertaining. Recent updates include HVAC replaced in 2021, upgraded bathrooms, and additional cabinets and counter space in the kitchen. Just under 2 miles from historic downtown Chestertown, you’ll be close to restaurants, shopping, festivals, walking trail, the waterfront park, and everything town has to offer.

123 Trafford Dr, Chestertown

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

$365,000

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

3 Beds ⋅ 3 Baths

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

24607 Chestertown Rd, Chestertown

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

$359,000

This lovely 1920 Chestertown colonial is full of character, charm and artistic detail. Thoughtfully updated, the home offers a bright, open floor plan that highlights its handcrafted touches. The living room features re-stored hardwood floors and a cozy gas fireplace, creating a warm cozy space. Natural light pours into the open and airy kitchen with newer painted cabinets, stenciled floors, shiplap walls, and a laundry/half bath just off kitchen. From the kitchen step straight into the private fenced courtyard, your own peaceful retreat. With a large brick patio, privacy plantings, and ample garden space to create your own haven. Upstairs you'll find two nice sized bedrooms, re-finished hardwood floors and a good size full bath with walk in shower. If you're looking for that quiet oasis in a downtown location, this is it!

2 Beds ⋅ 2 Baths

This lovely 1920 Chestertown colonial is full of character, charm and artistic detail. Thoughtfully updated, the home offers a bright, open floor plan that highlights its handcrafted touches. The living room features re-stored hardwood floors and a cozy gas fireplace, creating a warm cozy space. Natural light pours into the open and airy kitchen with newer painted cabinets, stenciled floors, shiplap walls, and a laundry/half bath just off kitchen. From the kitchen step straight into the private fenced courtyard, your own peaceful retreat. With a large brick patio, privacy plantings, and ample garden space to create your own haven. Upstairs you'll find two nice sized bedrooms, re-finished hardwood floors and a good size full bath with walk in shower. If you're looking for that quiet oasis in a downtown location, this is it!

101 S College Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$350,000

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006168 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

1 Beds ⋅ 1 Baths

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006168 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

117 Water St N Unit 2B, Chestertown

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

$349,900

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

501 High St, Chestertown

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

$349,900

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

4 Beds ⋅ 2 Baths

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

8668 Elm Rd, Chestertown

Listing courtesy of Kevin Dey Realty. Contact:

$339,000

What used to be known as the 'Pomona Store' is back on the market with fresh updates throughout! 4 bedroom house with in-law suite (additional 2 rooms on main level) and income producing unit attached! This property has so many possibilities for all types of businesses! Come and bring your imagination! House is 2444 sq ft with an additional 1100 sq ft (approx) of commercial space. Set on over half an acre in idylic Quaker Neck, yet only minutes from downtown Chestertown!

6746 Quaker Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$339,000

5 Beds ⋅ 3 Baths

6746 Quaker Neck Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$325,000

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

5 Beds ⋅ 2 Baths

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

234 N Kent St, Chestertown

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

$325,000

A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial. Fully finished basement. Plenty of parking. A great place for a centrally located home or office.

896 Washington Ave, Chestertown

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

$325,000

A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial. Full finished basement. More details and pictures coming soon!

3 Beds ⋅ 1 Baths

A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial. Full finished basement. More details and pictures coming soon!

896 Washington Ave, Chestertown

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

$320,000

Three bedroom one-floor living on a spacious lot in Chester Harbor! Over half an acre of nicely shaded yard space, and a short distance to the public beach on Mill Creek. 3 bedrooms and 1.5 bathrooms, open living and dining space, large sunroom/ porch with wood-burning stove, and an additional wood stove in the living room. Outside there's a small storage shed and a larger workshop/shed next to the asphalt driveway. The sunroom leads to a deck overlooking the large yard. Great community with water access. Quick ten minutes into Chestertown, and less than an hour to Middletown DE or Annapolis.

3 Beds ⋅ 2 Baths

Three bedroom one-floor living on a spacious lot in Chester Harbor! Over half an acre of nicely shaded yard space, and a short distance to the public beach on Mill Creek. 3 bedrooms and 1.5 bathrooms, open living and dining space, large sunroom/ porch with wood-burning stove, and an additional wood stove in the living room. Outside there's a small storage shed and a larger workshop/shed next to the asphalt driveway. The sunroom leads to a deck overlooking the large yard. Great community with water access. Quick ten minutes into Chestertown, and less than an hour to Middletown DE or Annapolis.

222 Dutchess Rd, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$315,000

Welcome to this charming farmhouse-style home in Fairlee! Completely renovated in 2023, this home is move-in ready and offers a comfortable mix of modern updates and farmhouse charm. Inside, you’ll find an open floor plan with luxury vinyl plank flooring throughout the main living areas. The living room offers a cozy space to relax and unwind. The updated kitchen is the heart of the home and features beautiful finishes and newer appliances, making it a great space for cooking and gathering. The home features two bedrooms, including a spacious primary bedroom, and two full bathrooms that have both been nicely updated. The spacious laundry room/mudroom provides plenty of room and adds everyday convenience. Enjoy your morning coffee or unwind at the end of the day on the inviting front porch, a great spot to sit back and enjoy the peaceful surroundings. Outside, you’ll find a large half-acre lot that backs to farmland, offering a beautiful setting. There’s plenty of room to enjoy the outdoors, garden, or let the kids and pets play. The gravel driveway provides parking for up to four vehicles. If you’re looking for a home that has been beautifully updated while still keeping that cozy farmhouse feel, this one is worth a look. Come see everything this Fairlee home has to offer!

2 Beds ⋅ 2 Baths

Welcome to this charming farmhouse-style home in Fairlee! Completely renovated in 2023, this home is move-in ready and offers a comfortable mix of modern updates and farmhouse charm. Inside, you’ll find an open floor plan with luxury vinyl plank flooring throughout the main living areas. The living room offers a cozy space to relax and unwind. The updated kitchen is the heart of the home and features beautiful finishes and newer appliances, making it a great space for cooking and gathering. The home features two bedrooms, including a spacious primary bedroom, and two full bathrooms that have both been nicely updated. The spacious laundry room/mudroom provides plenty of room and adds everyday convenience. Enjoy your morning coffee or unwind at the end of the day on the inviting front porch, a great spot to sit back and enjoy the peaceful surroundings. Outside, you’ll find a large half-acre lot that backs to farmland, offering a beautiful setting. There’s plenty of room to enjoy the outdoors, garden, or let the kids and pets play. The gravel driveway provides parking for up to four vehicles. If you’re looking for a home that has been beautifully updated while still keeping that cozy farmhouse feel, this one is worth a look. Come see everything this Fairlee home has to offer!

22974 Bay Shore Rd, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

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