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Hartwell Estate features 80 private acres with pristine, panoramic views on the mouth of the Langford and Chester River. This light filled custom built home and property captures the essence of serene living on Maryland's Eastern Shore. One of only 4 premiere properties at the end of Quaker Neck, often called "Kent County's Gold Coast" is sited to take advantage of the natural landscape with expansive views of the river, the owners' goal was to retain the feel and function of a working farm, but to add a modern house inspired by Maryland's historic heritage. The residence succeeds as a home for family comfort, entertaining, relaxing, gardening, hunting, fishing, birding and appreciating wildlife. Its east/west orientation highlights sunrises and sunsets that can be enjoyed from every room in the house. A real retreat. The five bedroom and 7 fireplace (woodburning) home was designed with 12-foot ceilings on the first floor to accentuate the views and the light. A main floor primary suite includes two separate ensuite dressing rooms and bathrooms along with a wood burning fireplace. The second floor has four bedrooms, three with fireplaces, and all with ensuite bathrooms. One bedroom has a separate sitting room. A wide hall runs along the width of the house providing access to all of the rooms. The property features the landscape design of acclaimed D.C. based Oehme, van Sweden. Hardscapes and plantings were strategically orchestrated and include a walled garden filled with flowering trees and shrubs along with a sweep of peonies in the spring. Three ponds invite active wildlife, including a beautiful blue heron. 50 acres of fields are currently being organically farmed by a neighboring farmer. An additional 3 bedroom and 2 bath cottage (c 2012), adjacent to a barn and silo, currently occupied by a caretaker, is situated near the property entrance. Two covered structures within the walled garden provide a relaxing reading or meditation venue. Bluestone and brick terraces along the entire river facing side of the house lead to a pool and pool pagoda. The property is uniquely designed to capture the feeling of the land while being welcoming and inviting to all who live there or visit. It has been lived in and loved by the original owner for over two decades. Family hunting and fishing are exceptional. Rock Fish is plentiful. The main residence has recently benefited from a new cedar shake roof and updated energy efficient French doors and windows throughout. The unfinished basement is approx. 2900 square feet with 9' ceilings, inviting the next steward to introduce additional lifestyle enhancements. Less than 10 miles to downtown Chestertown, with its restaurants, coffee shops, food stores, bookstore and vibrant music and art scene, this property combines riverfront tranquility with easy access to town. Additional FAQ: 2013-caretaker house built; 2020 small pond redesigned and landscaped; 2021 new cedar shake roof installed, copper gutters and downspouts repaired as needed; 2022 all windows and French doors on main level replaced with top of line Anderson product- trim removed, replaced and painted; 3 lintels in walled garden replaced with black walnut; 2024 resurfaced entire lane from Lands End Road to main residence; all windows and French doors on 2nd level replaced; farm buildings painted. Property access is restricted to scheduled appointments only.

5 Beds ⋅ 8 Baths

Hartwell Estate features 80 private acres with pristine, panoramic views on the mouth of the Langford and Chester River. This light filled custom built home and property captures the essence of serene living on Maryland's Eastern Shore. One of only 4 premiere properties at the end of Quaker Neck, often called "Kent County's Gold Coast" is sited to take advantage of the natural landscape with expansive views of the river, the owners' goal was to retain the feel and function of a working farm, but to add a modern house inspired by Maryland's historic heritage. The residence succeeds as a home for family comfort, entertaining, relaxing, gardening, hunting, fishing, birding and appreciating wildlife. Its east/west orientation highlights sunrises and sunsets that can be enjoyed from every room in the house. A real retreat. The five bedroom and 7 fireplace (woodburning) home was designed with 12-foot ceilings on the first floor to accentuate the views and the light. A main floor primary suite includes two separate ensuite dressing rooms and bathrooms along with a wood burning fireplace. The second floor has four bedrooms, three with fireplaces, and all with ensuite bathrooms. One bedroom has a separate sitting room. A wide hall runs along the width of the house providing access to all of the rooms. The property features the landscape design of acclaimed D.C. based Oehme, van Sweden. Hardscapes and plantings were strategically orchestrated and include a walled garden filled with flowering trees and shrubs along with a sweep of peonies in the spring. Three ponds invite active wildlife, including a beautiful blue heron. 50 acres of fields are currently being organically farmed by a neighboring farmer. An additional 3 bedroom and 2 bath cottage (c 2012), adjacent to a barn and silo, currently occupied by a caretaker, is situated near the property entrance. Two covered structures within the walled garden provide a relaxing reading or meditation venue. Bluestone and brick terraces along the entire river facing side of the house lead to a pool and pool pagoda. The property is uniquely designed to capture the feeling of the land while being welcoming and inviting to all who live there or visit. It has been lived in and loved by the original owner for over two decades. Family hunting and fishing are exceptional. Rock Fish is plentiful. The main residence has recently benefited from a new cedar shake roof and updated energy efficient French doors and windows throughout. The unfinished basement is approx. 2900 square feet with 9' ceilings, inviting the next steward to introduce additional lifestyle enhancements. Less than 10 miles to downtown Chestertown, with its restaurants, coffee shops, food stores, bookstore and vibrant music and art scene, this property combines riverfront tranquility with easy access to town. Additional FAQ: 2013-caretaker house built; 2020 small pond redesigned and landscaped; 2021 new cedar shake roof installed, copper gutters and downspouts repaired as needed; 2022 all windows and French doors on main level replaced with top of line Anderson product- trim removed, replaced and painted; 3 lintels in walled garden replaced with black walnut; 2024 resurfaced entire lane from Lands End Road to main residence; all windows and French doors on 2nd level replaced; farm buildings painted. Property access is restricted to scheduled appointments only.

23620 Lands End Rd, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Cross Street Realtors LLC.

$3,000,000

Welcome to the epitome of Eastern Shore waterfront luxury, offered for the first time in almost 60 years. This stunning 11-acre estate offers an unparalleled lifestyle, featuring 560 feet of prime water frontage on the Chester River and a private 140-foot dock with 7 feet of mean low water, perfect for all your adventures. ** The heart of this property is the beautifully renovated 3-bedroom, 2 full bath, 2 half bath main home, meticulously remodeled in 2018 with the highest quality materials and fixtures. The residence boasts sweeping water views from nearly every room, allowing you to enjoy picturesque sunrises Chester River. ** As you enter, you are greeted by a grand living room featuring a striking five-foot fireplace set within a soaring vaulted ceiling, creating a warm and inviting atmosphere. Expansive windows frame the breathtaking views and fill the space with natural light, enhancing the open-concept design that is perfect for both relaxing and entertaining. ** The gourmet kitchen is a chef's dream, equipped with top-of-the-line stainless steel appliances, custom cabinetry, an oversized island with seating, and elegant custom stone and wood countertops. This thoughtfully designed space allows for effortless meal preparation and entertaining. ** Retreat to the luxurious primary suite, a true sanctuary featuring its own private walled garden, offering a serene escape for relaxation and outdoor enjoyment. The suite also includes a cozy fireplace, perfect for creating a romantic ambiance. The spa-like bathroom is designed for ultimate relaxation, a spacious glass-enclosed double head shower, and dual vanities with exquisite finishes. A generous walk-in closet provides ample storage, ensuring organization and convenience. ** The outdoor living features of this luxurious estate are truly exceptional, designed to create an idyllic sanctuary for relaxation and entertainment. At the heart of the outdoor space is a stunning waterfront concrete pool, refurbished in 2018, offering a refreshing retreat on warm summer days while providing breathtaking views of the Chester River. Surrounding the home, the professionally designed landscaping enhances the natural beauty of the property, featuring lush gardens, vibrant plantings, and mature ornamental trees. The side patio, complete with a charming brick fire pit, invites gatherings with friends and family, perfect for cozy evenings under the stars. The poolside patio off the main living room makes alfresco dining a breeze. Additionally, the private walled garden serves as a tranquil oasis, offering a serene space to unwind amidst nature, making this outdoor area the perfect complement to the luxurious lifestyle this estate offers. ** Accommodate guests or staff in the charming 3-bedroom, 2-bath guest/caretaker's cottage, built in 2013. A spacious 2.5-bay workshop provides ample storage for your outdoor equipment and hobbies. ** This exceptional property seamlessly blends luxury and tranquility, offering a unique opportunity to own a piece of paradise on the Eastern Shore. Don’t miss your chance to experience the charm and elegance of this extraordinary waterfront estate!

3 Beds ⋅ 4 Baths

Welcome to the epitome of Eastern Shore waterfront luxury, offered for the first time in almost 60 years. This stunning 11-acre estate offers an unparalleled lifestyle, featuring 560 feet of prime water frontage on the Chester River and a private 140-foot dock with 7 feet of mean low water, perfect for all your adventures. ** The heart of this property is the beautifully renovated 3-bedroom, 2 full bath, 2 half bath main home, meticulously remodeled in 2018 with the highest quality materials and fixtures. The residence boasts sweeping water views from nearly every room, allowing you to enjoy picturesque sunrises Chester River. ** As you enter, you are greeted by a grand living room featuring a striking five-foot fireplace set within a soaring vaulted ceiling, creating a warm and inviting atmosphere. Expansive windows frame the breathtaking views and fill the space with natural light, enhancing the open-concept design that is perfect for both relaxing and entertaining. ** The gourmet kitchen is a chef's dream, equipped with top-of-the-line stainless steel appliances, custom cabinetry, an oversized island with seating, and elegant custom stone and wood countertops. This thoughtfully designed space allows for effortless meal preparation and entertaining. ** Retreat to the luxurious primary suite, a true sanctuary featuring its own private walled garden, offering a serene escape for relaxation and outdoor enjoyment. The suite also includes a cozy fireplace, perfect for creating a romantic ambiance. The spa-like bathroom is designed for ultimate relaxation, a spacious glass-enclosed double head shower, and dual vanities with exquisite finishes. A generous walk-in closet provides ample storage, ensuring organization and convenience. ** The outdoor living features of this luxurious estate are truly exceptional, designed to create an idyllic sanctuary for relaxation and entertainment. At the heart of the outdoor space is a stunning waterfront concrete pool, refurbished in 2018, offering a refreshing retreat on warm summer days while providing breathtaking views of the Chester River. Surrounding the home, the professionally designed landscaping enhances the natural beauty of the property, featuring lush gardens, vibrant plantings, and mature ornamental trees. The side patio, complete with a charming brick fire pit, invites gatherings with friends and family, perfect for cozy evenings under the stars. The poolside patio off the main living room makes alfresco dining a breeze. Additionally, the private walled garden serves as a tranquil oasis, offering a serene space to unwind amidst nature, making this outdoor area the perfect complement to the luxurious lifestyle this estate offers. ** Accommodate guests or staff in the charming 3-bedroom, 2-bath guest/caretaker's cottage, built in 2013. A spacious 2.5-bay workshop provides ample storage for your outdoor equipment and hobbies. ** This exceptional property seamlessly blends luxury and tranquility, offering a unique opportunity to own a piece of paradise on the Eastern Shore. Don’t miss your chance to experience the charm and elegance of this extraordinary waterfront estate!

25440 Learman Rd, Chestertown

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

Selling Office: Coldwell Banker Realty.

$2,100,000

Gobbler Hill, circa 1858 with an addition built in 1989, sits like a jewel atop one of the highest points in Kent County. Listed on the National Historic Registry, the transitional architecture is an excellent example of late Greek Revival to early Italianate. The property consists of four parcels totaling over 65 acres. Wildlife abounds on the fields of native prairie grasses, wild flowers, woods, approximately 20 tilled acres and a large pond. Impeccable attention was payed to maintaining the historic character of both the interior and exterior. From the Lincrusta wall covering, 19th century faux wood finishing, plaster medallions, white and sugar pine wood floors and crown molding on the 11 ft. ceilings to the monumental copper roof, the thoughtful restoration is stunning. The newer addition beautifully blends into the original section adding modern conveniences and natural light. The library boasts black walnut bookshelves constructed by a local craftsman. Well maintained grounds offer gardens, mature trees, a classic poured concrete in ground pool with inlaid tile and stunning views. This unique, lovingly restored piece of Kent County history is now looking for a new steward to guide it into its next chapter.

6 Beds ⋅ 5 Baths

Gobbler Hill, circa 1858 with an addition built in 1989, sits like a jewel atop one of the highest points in Kent County. Listed on the National Historic Registry, the transitional architecture is an excellent example of late Greek Revival to early Italianate. The property consists of four parcels totaling over 65 acres. Wildlife abounds on the fields of native prairie grasses, wild flowers, woods, approximately 20 tilled acres and a large pond. Impeccable attention was payed to maintaining the historic character of both the interior and exterior. From the Lincrusta wall covering, 19th century faux wood finishing, plaster medallions, white and sugar pine wood floors and crown molding on the 11 ft. ceilings to the monumental copper roof, the thoughtful restoration is stunning. The newer addition beautifully blends into the original section adding modern conveniences and natural light. The library boasts black walnut bookshelves constructed by a local craftsman. Well maintained grounds offer gardens, mature trees, a classic poured concrete in ground pool with inlaid tile and stunning views. This unique, lovingly restored piece of Kent County history is now looking for a new steward to guide it into its next chapter.

10121 Fairlee Rd, Chestertown

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

Selling Office: Unrepresented Buyer Office.

$1,900,000

Price Improvement! Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your private dock with new boat lift, sandy beach, and stunning new saltwater pool. Exposed beams, scalamandre wallpaper, and multiple fireplaces. First floor owners suite featuring reclaimed pine flooring, private laundry area, walk-in closet, gas fireplace and remodeled bath with soaking tub. Second floor owner's suite with additional laundry area and remodeled bath. Breezeway to the garage. New irrigation system to all flower beds. New paint inside and out. House has had major remodels in 2000 and 2020. Town sewer. Not far from town, but the property has a private feel. Some interior images have been AI virtually staged for illustrative purposes. These images do not represent the property's current furnishings or decor.

5 Beds ⋅ 5 Baths

Price Improvement! Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your private dock with new boat lift, sandy beach, and stunning new saltwater pool. Exposed beams, scalamandre wallpaper, and multiple fireplaces. First floor owners suite featuring reclaimed pine flooring, private laundry area, walk-in closet, gas fireplace and remodeled bath with soaking tub. Second floor owner's suite with additional laundry area and remodeled bath. Breezeway to the garage. New irrigation system to all flower beds. New paint inside and out. House has had major remodels in 2000 and 2020. Town sewer. Not far from town, but the property has a private feel. Some interior images have been AI virtually staged for illustrative purposes. These images do not represent the property's current furnishings or decor.

7989 Quaker Neck Rd, Chestertown

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

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

$1,650,000

Exceptional renovation that offers everything you could want in a waterfront home.

3 Beds ⋅ 2 Baths

Exceptional renovation that offers everything you could want in a waterfront home.

114 Chester Vw, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Non Subscribing Office.

$1,550,000

5 Beds ⋅ 3 Baths

7761 Broad Neck Rd, Chestertown

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

Selling Office: Davis Real Estate, Inc..

$1,550,000

**Exquisite Waterfront Retreat on Chester River** Welcome to 7961 Quaker Neck Road, Chestertown, MD – an elegant and modern sanctuary nestled on the coveted Chester River, offering a rare opportunity to own a completely remodeled waterfront property. This exceptional home encompasses five beautifully appointed bedrooms, four luxurious bathrooms, and sits gracefully on nearly half an acre of pristine land. As you step inside, you're greeted by an abundance of natural light streaming through perfectly placed skylights, highlighting the breathtaking waterfront views. The main level features an expansive living room adorned with a cozy fireplace, seamlessly flowing into a chef's dream kitchen. This culinary masterpiece boasts an expansive island with seating for eight, upgraded cabinetry and countertops, a deep farmhouse sink, and top-of-the-line stainless steel appliances, including two dishwashers, two wall ovens, a gas range, microwave, refrigerator, and a wine fridge. Every detail has been meticulously crafted to showcase the stunning water views. The adjoining sunroom offers a serene space to unwind, while the recreation room provides ample space for entertainment and leisure. The main level also includes three spacious bedrooms, one with an ensuite, and an additional full bathroom. Upstairs, discover two more bedrooms, each with its own en suite, and a primary bedroom that features expansive windows and access to a private deck, perfect for savoring the tranquil water views. Outside, the peaceful backyard beckons you to relax and enjoy the serene beauty of the Chester River. A recently constructed dock, less than three years old, provides easy access to the water, while two outdoor showers offer convenience after a day of river adventures. The large detached garage ensures ample storage space for all your needs. This home is enhanced by a range of modern upgrades, including newer windows, skylights, and doors, all completed in 2022, along with freshly painted exteriors and a Rinnai water heater. Three working fireplaces, two wood-burning and one gas, create inviting spaces to gather on cool evenings. Additional amenities include a whole house generator, two whole house dehumidifiers, and a fully remodeled interior designed for ultimate relaxation and enjoyment. Located just minutes from Historic Chestertown, this property allows you to enjoy the charm of small-town living with access to a variety of shops, coffee houses, and bakeries. Experience the perfect blend of elegance and modern comfort in this meticulously curated waterfront retreat. Homes like this are truly a rare find.

5 Beds ⋅ 4 Baths

**Exquisite Waterfront Retreat on Chester River** Welcome to 7961 Quaker Neck Road, Chestertown, MD – an elegant and modern sanctuary nestled on the coveted Chester River, offering a rare opportunity to own a completely remodeled waterfront property. This exceptional home encompasses five beautifully appointed bedrooms, four luxurious bathrooms, and sits gracefully on nearly half an acre of pristine land. As you step inside, you're greeted by an abundance of natural light streaming through perfectly placed skylights, highlighting the breathtaking waterfront views. The main level features an expansive living room adorned with a cozy fireplace, seamlessly flowing into a chef's dream kitchen. This culinary masterpiece boasts an expansive island with seating for eight, upgraded cabinetry and countertops, a deep farmhouse sink, and top-of-the-line stainless steel appliances, including two dishwashers, two wall ovens, a gas range, microwave, refrigerator, and a wine fridge. Every detail has been meticulously crafted to showcase the stunning water views. The adjoining sunroom offers a serene space to unwind, while the recreation room provides ample space for entertainment and leisure. The main level also includes three spacious bedrooms, one with an ensuite, and an additional full bathroom. Upstairs, discover two more bedrooms, each with its own en suite, and a primary bedroom that features expansive windows and access to a private deck, perfect for savoring the tranquil water views. Outside, the peaceful backyard beckons you to relax and enjoy the serene beauty of the Chester River. A recently constructed dock, less than three years old, provides easy access to the water, while two outdoor showers offer convenience after a day of river adventures. The large detached garage ensures ample storage space for all your needs. This home is enhanced by a range of modern upgrades, including newer windows, skylights, and doors, all completed in 2022, along with freshly painted exteriors and a Rinnai water heater. Three working fireplaces, two wood-burning and one gas, create inviting spaces to gather on cool evenings. Additional amenities include a whole house generator, two whole house dehumidifiers, and a fully remodeled interior designed for ultimate relaxation and enjoyment. Located just minutes from Historic Chestertown, this property allows you to enjoy the charm of small-town living with access to a variety of shops, coffee houses, and bakeries. Experience the perfect blend of elegance and modern comfort in this meticulously curated waterfront retreat. Homes like this are truly a rare find.

7961 Quaker Neck Rd, Chestertown

Listing courtesy of Compass. Contact:

Selling Office: Compass.

$1,524,900

Chesapeake Bay Waterfront with Breathtaking Views. Experience exceptional waterfront living in this custom-built 5,240 sq ft residence, beautifully situated on an elevated bluff in the sought-after Great Oak Community of Chestertown, Maryland. Offering 5 bedrooms and 3.5 baths, this remarkable home captures sweeping Chesapeake Bay views and unforgettable sunsets from nearly every room. The property features 150 feet of riprap-protected shoreline and direct water access via a brand-new private 140ft pier complete with lighting, water service in four locations, a 12,000-lb boat lift, and two jet ski lifts—perfect for boating and waterfront recreation. Inside, the home impresses with 9-foot ceilings and hardwood floors throughout most of the main level. Designed for entertaining, the gourmet kitchen showcases luxury appliances, a distinctive chef’s cutting-board countertop, and new LVP flooring. The grand great room is a true showpiece, featuring a floor-to-ceiling brick wood-burning fireplace, vaulted shiplap pine ceiling, exposed beams, and views of the Bay! Additional living spaces include an elegant formal dining room, a spacious gathering room, and a casual dining area highlighted by a gas fireplace. The first-floor primary suite offers privacy and comfort with a walk-in closet and an updated bath featuring new flooring, a corner soaking tub, and dual vanities. Two additional bedrooms, a full bath, and a laundry room complete the main level. The second floor provides two generously sized bedrooms, a large living area, a full bath, and an 18’ x 22’ unfinished bonus room/man cave with a separate staircase offering access to the garage or exterior—ideal for future expansion or customization. Notable features include a new roof, an oversized two-car garage with workbench, a small basement housing a state-of-the-art temperature- and humidity-controlled wine cellar, a Culligan whole-house water filtration system, and two hot water heaters. One of the home’s most captivating spaces is the expansive screened-in porch, stretching across much of the waterfront side of the home. With three ceiling fans and panoramic Chesapeake Bay views, it offers the perfect setting for relaxing or entertaining year-round. Whether you’re seeking a serene waterfront retreat or a home designed for memorable gatherings, this exceptional coastal property delivers. Just minutes from historic Chestertown, home to Washington College, waterfront dining, farmers’ markets, parks, festivals, and river cruises. Conveniently located near Safe Harbor Great Oak Marina and approximately 90 minutes from Washington, D.C. and Philadelphia. Schedule your private showing and experience Chesapeake Bay living at its finest

5 Beds ⋅ 4 Baths

Chesapeake Bay Waterfront with Breathtaking Views. Experience exceptional waterfront living in this custom-built 5,240 sq ft residence, beautifully situated on an elevated bluff in the sought-after Great Oak Community of Chestertown, Maryland. Offering 5 bedrooms and 3.5 baths, this remarkable home captures sweeping Chesapeake Bay views and unforgettable sunsets from nearly every room. The property features 150 feet of riprap-protected shoreline and direct water access via a brand-new private 140ft pier complete with lighting, water service in four locations, a 12,000-lb boat lift, and two jet ski lifts—perfect for boating and waterfront recreation. Inside, the home impresses with 9-foot ceilings and hardwood floors throughout most of the main level. Designed for entertaining, the gourmet kitchen showcases luxury appliances, a distinctive chef’s cutting-board countertop, and new LVP flooring. The grand great room is a true showpiece, featuring a floor-to-ceiling brick wood-burning fireplace, vaulted shiplap pine ceiling, exposed beams, and views of the Bay! Additional living spaces include an elegant formal dining room, a spacious gathering room, and a casual dining area highlighted by a gas fireplace. The first-floor primary suite offers privacy and comfort with a walk-in closet and an updated bath featuring new flooring, a corner soaking tub, and dual vanities. Two additional bedrooms, a full bath, and a laundry room complete the main level. The second floor provides two generously sized bedrooms, a large living area, a full bath, and an 18’ x 22’ unfinished bonus room/man cave with a separate staircase offering access to the garage or exterior—ideal for future expansion or customization. Notable features include a new roof, an oversized two-car garage with workbench, a small basement housing a state-of-the-art temperature- and humidity-controlled wine cellar, a Culligan whole-house water filtration system, and two hot water heaters. One of the home’s most captivating spaces is the expansive screened-in porch, stretching across much of the waterfront side of the home. With three ceiling fans and panoramic Chesapeake Bay views, it offers the perfect setting for relaxing or entertaining year-round. Whether you’re seeking a serene waterfront retreat or a home designed for memorable gatherings, this exceptional coastal property delivers. Just minutes from historic Chestertown, home to Washington College, waterfront dining, farmers’ markets, parks, festivals, and river cruises. Conveniently located near Safe Harbor Great Oak Marina and approximately 90 minutes from Washington, D.C. and Philadelphia. Schedule your private showing and experience Chesapeake Bay living at its finest

10800 Cliff Rd, Chestertown

Listing courtesy of Taylor Properties. Contact:

Selling Office: RE/MAX Chesapeake.

$1,236,000

Price is the starting bid for a Ten-X auction to be held online from December 15-17. Pre-auction offers are being considered. Contact listing agent for details. Radcliffe Mill presents an exceptional opportunity for a savvy investor looking for value and a one-of-a-kind investment with endless possibilities. Since its major restoration in 2007, and further transformation in 2017, the property has operated as a mixed-use space. The Mill building features four floors of office space and a 70+ seat restaurant. The Annex/Seed House houses a brewery which hosts live music on weekend, as well as offices. Additionally, there is an undeveloped Grain Elevator, parking for 65 vehicles, and a dedicated loading dock for the restaurant. Having played a significant role in Kent County’s agricultural landscape since 1694, Radcliffe Mill underwent a historic restoration in 2007, transforming it into its current use with over 16,000 square feet of finished space. The centerpiece is the four-story mill building, dating back to 1891. The restoration seamlessly blended modern amenities like an elevator, sprinkler system and HVAC systems, with original features such as exposed beams and reclaimed flooring. While currently configured as office space across four floors, the property's zoning permits various uses, including conversion to apartments. Café Sado, a local sushi restaurant, is also housed within the mill building. All of the major restaurant equipment is included in the sale. The Annex dates back to the early 1900s and The Seed House to the 1970s. Today, the blended building features soaring ceilings, exposed woodwork, and meticulously restored standing end 2x4 flooring. Presently, the building accommodates a diverse range of wellness practitioners, with the studio space and café awaiting the creative touch of a new occupant. The sale includes all café equipment, including refrigerators, freezer, ice maker, keg tap, a warming oven and more. Four of The Seed Offices are on the ground floor, with a fifth office on the second floor, along with additional storage and laundry facilities. Finally, there is an unfinished Grain Elevator, awaiting the creativity of a new buyer. Radcliffe Mill is on the National Register of Historic Places (see documents), and having previously received historic preservation tax credits a new owner could benefit from a shorter process for further property development and improvement tax credits. The property is also in a Maryland Enterprise Zone, and an Opportunity Zone and eligible for energy improvement incentive programs. Radcliffe Mill is strategically located one-mile from downtown Chestertown, a short walk along the rail trail, which used to run directly to the grain elevator. Founded in 1706 on the banks of the Chester River, Chestertown is home to Washington College. Located approximately 80 miles from Washington, DC and Philadelphia, PA and an hour from Wilmington, DE, Chestertown hosts a number of vibrant festivals throughout the year and an active arts and entertainment district. The property consists of two different parcels, and each parcel is also being offered for sale separately. Buyers requesting additional information must sign a Non-Disclosure Agreement.

860 & 870 High St, Chestertown

Listing courtesy of Taylor Properties. Contact:

Selling Office: Metropolitan Regional Information Systems, Inc..

$1,200,000

Wake up to sweeping views of the Chester River and end each day with spectacular western sunsets from this exceptional waterfront. Situated on 0.61 acres with 169 feet +/- of waterfrontage and deep-water access, this 4-bedroom, 3-bath brick Cape Cod invites you to enjoy the very best of waterfront living. Unlike many waterfront properties, the level lot provides easy access from the home to the water and private pier—no steep banks or long flights of stairs to navigate. Whether you enjoy boating, kayaking, fishing, crabbing, or simply relaxing by the water, this property makes it easy to embrace the Eastern Shore lifestyle. Inside, you'll find more than 2,200 square feet of comfortable living space designed to capture the stunning river views. A charming four-season room with brick flooring and panoramic water views is the perfect place to enjoy your morning coffee year-round, while the screened porch is ideal for summer crab feasts and outdoor entertaining. At the heart of the home, a wood-burning brick fireplace that creates a warm and inviting atmosphere. The flexible floor plan includes a main-level bedroom and full bath, ideal for guests or one-level living. Upstairs, the primary suite serves as a peaceful retreat, featuring breathtaking river views, abundant natural light, and a private ensuite bath with double vanities and a tiled shower. Two additional generously sized bedrooms and another full bath provide ample space for family and visitors. Recent improvements include a new roof in 2020 and an electric vehicle charger installed in the attached garage in 2025. An irrigation system serves both the front and rear yards, and the property is located outside the flood plain, so flood insurance is not required. Tucked away near the end of a private road, this serene setting feels calm and peaceful while remaining just minutes from Chestertown's shops, restaurants, marina, and popular farmers market. Enjoy daily visits from eagles, ospreys, herons, owls, deer, and other wildlife, all from your own backyard. Whether you're searching for a full-time waterfront residence or the perfect weekend escape, this rare Chester River property offers the beauty, tranquility, and lifestyle that makes Maryland's Eastern Shore so special.

4 Beds ⋅ 3 Baths

Wake up to sweeping views of the Chester River and end each day with spectacular western sunsets from this exceptional waterfront. Situated on 0.61 acres with 169 feet +/- of waterfrontage and deep-water access, this 4-bedroom, 3-bath brick Cape Cod invites you to enjoy the very best of waterfront living. Unlike many waterfront properties, the level lot provides easy access from the home to the water and private pier—no steep banks or long flights of stairs to navigate. Whether you enjoy boating, kayaking, fishing, crabbing, or simply relaxing by the water, this property makes it easy to embrace the Eastern Shore lifestyle. Inside, you'll find more than 2,200 square feet of comfortable living space designed to capture the stunning river views. A charming four-season room with brick flooring and panoramic water views is the perfect place to enjoy your morning coffee year-round, while the screened porch is ideal for summer crab feasts and outdoor entertaining. At the heart of the home, a wood-burning brick fireplace that creates a warm and inviting atmosphere. The flexible floor plan includes a main-level bedroom and full bath, ideal for guests or one-level living. Upstairs, the primary suite serves as a peaceful retreat, featuring breathtaking river views, abundant natural light, and a private ensuite bath with double vanities and a tiled shower. Two additional generously sized bedrooms and another full bath provide ample space for family and visitors. Recent improvements include a new roof in 2020 and an electric vehicle charger installed in the attached garage in 2025. An irrigation system serves both the front and rear yards, and the property is located outside the flood plain, so flood insurance is not required. Tucked away near the end of a private road, this serene setting feels calm and peaceful while remaining just minutes from Chestertown's shops, restaurants, marina, and popular farmers market. Enjoy daily visits from eagles, ospreys, herons, owls, deer, and other wildlife, all from your own backyard. Whether you're searching for a full-time waterfront residence or the perfect weekend escape, this rare Chester River property offers the beauty, tranquility, and lifestyle that makes Maryland's Eastern Shore so special.

202 Royston Shores Rd, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$1,165,000

From within and without, from the front, the sides and the back, this exceptional 1876 and 1998 residence sings. Every passer-by has stopped and gazed upon the wrap around porch. No doubt, many a conversation "over the railing" has taken place for decades. Those fortunate enough to have enjoyed hospitality inside this German-wood clad home have experienced both its expansive flow of inter-connected rooms with center hall, the cozy grandness of an era long ago and comfortable living today amidst an eclectic mix of modern art and furniture, antiques, and other treasures. Prominent historic downtown location. Significant land parcel. 5 bedrooms, office, 6 public rooms on first floor, 4 and 1 half baths. Beautiful side and rear garden, with pond, brick paths, and exceptional specimens. Former garage converted to studio with full bath. Come visit Charleston or Savanah in Chestertown.

5 Beds ⋅ 5 Baths

From within and without, from the front, the sides and the back, this exceptional 1876 and 1998 residence sings. Every passer-by has stopped and gazed upon the wrap around porch. No doubt, many a conversation "over the railing" has taken place for decades. Those fortunate enough to have enjoyed hospitality inside this German-wood clad home have experienced both its expansive flow of inter-connected rooms with center hall, the cozy grandness of an era long ago and comfortable living today amidst an eclectic mix of modern art and furniture, antiques, and other treasures. Prominent historic downtown location. Significant land parcel. 5 bedrooms, office, 6 public rooms on first floor, 4 and 1 half baths. Beautiful side and rear garden, with pond, brick paths, and exceptional specimens. Former garage converted to studio with full bath. Come visit Charleston or Savanah in Chestertown.

119 High St, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact:

Selling Office: Cross Street Realtors LLC.

$1,150,000

**Exclusive Waterfront Craftsman Home with Sandy Beach – A Rare Opportunity** Nestled on the serene East Fork of Langford Creek/Bay, this stunning 3-bedroom Craftsman- style home offers the perfect blend of comfort, privacy, and natural beauty. With approximately 150 feet of shoreline and a sandy beach, this property is a true waterfront gem. **Key Features:** - **Spacious Great Room**: Added in 2001, the great room boasts expansive living space with vaulted ceilings, a loft, and a catwalk for a unique and inviting atmosphere. - **Updated Kitchen**: In 2022, the kitchen was beautifully remodeled to include modern finishes and appliances, making it the perfect space for entertaining. - **Exclusive Community**: Located within the Cacaway Farm Cooperative Housing Corporation, this home is part of a select group of 5 waterfront properties. Enjoy ownership in a corporation with the added benefit of sharing common expenses for a lower cost of living. Soon the coop ownership to become fee simple. Make your appointment today to be apart of that in the near future, with this lower price and no transfer fees. - **Private Waterfront**: A gentle slope leads you to your own piece of paradise with a sandy beach, ideal for launching kayaks or canoes. Plus, the deep-water boat slip at the community dock provides the perfect haven for boat owners. - **South-Facing Exposure**: Enjoy breathtaking water views and refreshing summer breezes from your south-facing waterfront. - **Heated Garage & Bonus Area**: The property includes a 2-car heated garage, built in 2006, with a separate storage area and a bonus space above—complete with radiant floor heat for year- round comfort. - **Modern Infrastructure**: A new BAT septic system was installed in the past 4 years, and the shared sewage disposal area is maintained by the county for worry-free living. This property offers the rare combination of privacy, community, and stunning waterfront access. Don't miss out on this incredible opportunity to own a piece of paradise. The south-facing orientation of the property offers a natural advantage when it comes to the climate and the breezes that sweep across the waterfront. Because of its position, the home is perfectly situated to catch the prevailing summer winds from the south, which are often cool and refreshing. These gentle breezes help to moderate the temperature, creating a comfortable, airy atmosphere throughout the warmer months. Whether you're relaxing on the deck, enjoying the beach, or sitting inside with the windows open, the breezes will bring a pleasant, natural ventilation, keeping things cool and comfortable even on the hottest days. The south-facing exposure also ensures you have plenty of sunshine throughout the day, adding to the overall warmth and welcoming feel of the space. This combination of sunlight and breeze provides a wonderful outdoor living experience, whether you’re lounging on the waterfront or enjoying an evening dinner on the deck with the gentle breeze in the air. It’s the kind of peaceful, tranquil environment that enhances the feeling of living in harmony with nature. **Please note**: Cacaway Farm Lane is a private road, so appointments are required to view the property. Schedule a showing today and make this dream home yours!

3 Beds ⋅ 4 Baths

**Exclusive Waterfront Craftsman Home with Sandy Beach – A Rare Opportunity** Nestled on the serene East Fork of Langford Creek/Bay, this stunning 3-bedroom Craftsman- style home offers the perfect blend of comfort, privacy, and natural beauty. With approximately 150 feet of shoreline and a sandy beach, this property is a true waterfront gem. **Key Features:** - **Spacious Great Room**: Added in 2001, the great room boasts expansive living space with vaulted ceilings, a loft, and a catwalk for a unique and inviting atmosphere. - **Updated Kitchen**: In 2022, the kitchen was beautifully remodeled to include modern finishes and appliances, making it the perfect space for entertaining. - **Exclusive Community**: Located within the Cacaway Farm Cooperative Housing Corporation, this home is part of a select group of 5 waterfront properties. Enjoy ownership in a corporation with the added benefit of sharing common expenses for a lower cost of living. Soon the coop ownership to become fee simple. Make your appointment today to be apart of that in the near future, with this lower price and no transfer fees. - **Private Waterfront**: A gentle slope leads you to your own piece of paradise with a sandy beach, ideal for launching kayaks or canoes. Plus, the deep-water boat slip at the community dock provides the perfect haven for boat owners. - **South-Facing Exposure**: Enjoy breathtaking water views and refreshing summer breezes from your south-facing waterfront. - **Heated Garage & Bonus Area**: The property includes a 2-car heated garage, built in 2006, with a separate storage area and a bonus space above—complete with radiant floor heat for year- round comfort. - **Modern Infrastructure**: A new BAT septic system was installed in the past 4 years, and the shared sewage disposal area is maintained by the county for worry-free living. This property offers the rare combination of privacy, community, and stunning waterfront access. Don't miss out on this incredible opportunity to own a piece of paradise. The south-facing orientation of the property offers a natural advantage when it comes to the climate and the breezes that sweep across the waterfront. Because of its position, the home is perfectly situated to catch the prevailing summer winds from the south, which are often cool and refreshing. These gentle breezes help to moderate the temperature, creating a comfortable, airy atmosphere throughout the warmer months. Whether you're relaxing on the deck, enjoying the beach, or sitting inside with the windows open, the breezes will bring a pleasant, natural ventilation, keeping things cool and comfortable even on the hottest days. The south-facing exposure also ensures you have plenty of sunshine throughout the day, adding to the overall warmth and welcoming feel of the space. This combination of sunlight and breeze provides a wonderful outdoor living experience, whether you’re lounging on the waterfront or enjoying an evening dinner on the deck with the gentle breeze in the air. It’s the kind of peaceful, tranquil environment that enhances the feeling of living in harmony with nature. **Please note**: Cacaway Farm Lane is a private road, so appointments are required to view the property. Schedule a showing today and make this dream home yours!

23393 Cacaway Farm Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Rock Hall Properties Real Estate.

$1,100,000

Welcome to Pheasantfield Farm, a 21- acre equestrian estate beautifully nestled on the Chester River. Fantastic location, ample privacy, and yet only a short drive, or boat ride, to historic Chestertown. The main home boasts 4 bedrooms and two and a half baths. The primary bedroom has a lovely view of the river, two walk-in closets and a large attached full bath. The spacious ranch-style home offers plenty of space for entertaining. Enjoy meals on the front porch, overlooking the Chester River. The property has extensive recent improvements between 2021-2024. New roof on the main house, guest house and horse barn. All new BAT septic system. The guest house, garage and horse barn have been newly power washed and painted. New American Standard dual fuel propane furnace with heat pump back up. New central AC/heat heat pump system. New on-demand hot water heater in guest house. The main home has an whole house generator with dedicated 500 gal propane tank. Completed in 2003, the 34x40 center aisle cedar horse barn with three light & airy 12x12 stalls offering sliding doors to center aisle and exterior. 8x12 tack room, electric, water and a full loft. With heavy custom wood gates to allow extra ventilation for exterior doors. 16'x 34' run-in area at back of barn with sliding doors on 3 sides, opening to multiple pasture options. Pasture is fenced by 3-rail wood horse fence with "no climb" galvanized wire. The property offers a 1 bedroom 1 bath guesthouse with a kitchen and living area. Next to the guesthouse is the oversized 4 car garage including a 19x30 workshop with heat, water and electric, plus a bonus heated office or storage area above. additionally there is a small barn to house a tractor and other farm equipment While not on the farm, enjoy exploring the Chester River! The private dock includes an electric boat lift, floating dock, and sun or swimming deck. Spend evenings watching the sunsets on the sundeck or easily launch a kayak off of the floating dock. Discover the many possibilities of Pheasantfield Farm, an exceptional waterfront escape in Queen Anne's County!

5 Beds ⋅ 4 Baths

Welcome to Pheasantfield Farm, a 21- acre equestrian estate beautifully nestled on the Chester River. Fantastic location, ample privacy, and yet only a short drive, or boat ride, to historic Chestertown. The main home boasts 4 bedrooms and two and a half baths. The primary bedroom has a lovely view of the river, two walk-in closets and a large attached full bath. The spacious ranch-style home offers plenty of space for entertaining. Enjoy meals on the front porch, overlooking the Chester River. The property has extensive recent improvements between 2021-2024. New roof on the main house, guest house and horse barn. All new BAT septic system. The guest house, garage and horse barn have been newly power washed and painted. New American Standard dual fuel propane furnace with heat pump back up. New central AC/heat heat pump system. New on-demand hot water heater in guest house. The main home has an whole house generator with dedicated 500 gal propane tank. Completed in 2003, the 34x40 center aisle cedar horse barn with three light & airy 12x12 stalls offering sliding doors to center aisle and exterior. 8x12 tack room, electric, water and a full loft. With heavy custom wood gates to allow extra ventilation for exterior doors. 16'x 34' run-in area at back of barn with sliding doors on 3 sides, opening to multiple pasture options. Pasture is fenced by 3-rail wood horse fence with "no climb" galvanized wire. The property offers a 1 bedroom 1 bath guesthouse with a kitchen and living area. Next to the guesthouse is the oversized 4 car garage including a 19x30 workshop with heat, water and electric, plus a bonus heated office or storage area above. additionally there is a small barn to house a tractor and other farm equipment While not on the farm, enjoy exploring the Chester River! The private dock includes an electric boat lift, floating dock, and sun or swimming deck. Spend evenings watching the sunsets on the sundeck or easily launch a kayak off of the floating dock. Discover the many possibilities of Pheasantfield Farm, an exceptional waterfront escape in Queen Anne's County!

300 Hickory Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Benson & Mangold, LLC.

$1,100,000

120 Speer Rd, Chestertown

Listing courtesy of Mackenzie Commercial R E SVCS, LLC. Contact:

Selling Office: Select Land & Homes, LLC.

$1,050,000

Experience the best of waterfront living just steps outside of the heart of Downtown Chestertown. Only a few blocks from shops, restaurants, the bustling farmers market, art galleries, annual festivals, and the vibrant cultural life that defines this beloved Eastern Shore community, this exceptional property offers a rare opportunity to enjoy riverfront living with walkable in-town convenience. * With five (plus) bedrooms accommodating up to fourteen guests and three full baths, the home is designed for comfort, flexibility, and enjoyment. Multiple indoor and outdoor gathering spaces make it ideal for those seeking a full-time residence, a weekend retreat, a multi-generational destination, or a strong investment property with outstanding rental potential. * On the main level, a cozy den with a wood-burning fireplace captures Chester River views, creating a warm and welcoming spot to relax after a day on the water. Additional living spaces provide room for groups to spread out—whether entertaining, working remotely, or simply taking a quiet moment to unwind. The primary suite offers its own private vantage point with a picture window overlooking the pool and riverfront—perfect for greeting the sunrise or watching wildlife glide across the water. * Outdoor living is where this property truly shines. Enjoy a covered patio for shaded summer crab feasts, a large deck with a stone fireplace for crisp evenings, and an in-ground pool that looks out toward the shore. With immediate water access, you’ll launch kayaks, paddle boards, and jet skis right from your backyard—ideal for embracing the river lifestyle. A two-car attached garage provides convenient storage for gear, bikes, and all the water toys. It could also be the perfect space to keep your street legal golf cart which the Town Of Chestertown now allows! * Your new home is also just a short walk from the full-service Chestertown Marina with the potential for a transferable slip—already paid through the 2026 boating season—ensuring you can enjoy hassle-free access to Chester River fun. Additionally, it's a quick ride to the Chester River Yacht & Country Club, where you can indulge in 18 holes of golf, relax by the pool, enjoy happy hour or meals at the full restaurant and bar, and partake in a host of other fantastic member benefits. * Whether you’re making it your full-time home, your getaway from the city, or your next strategic investment, this property delivers the best of Chestertown living—waterfront, walkable, and wonderfully welcoming. Embrace a lifestyle of leisure and convenience in this exceptional location.

5 Beds ⋅ 3 Baths

Experience the best of waterfront living just steps outside of the heart of Downtown Chestertown. Only a few blocks from shops, restaurants, the bustling farmers market, art galleries, annual festivals, and the vibrant cultural life that defines this beloved Eastern Shore community, this exceptional property offers a rare opportunity to enjoy riverfront living with walkable in-town convenience. * With five (plus) bedrooms accommodating up to fourteen guests and three full baths, the home is designed for comfort, flexibility, and enjoyment. Multiple indoor and outdoor gathering spaces make it ideal for those seeking a full-time residence, a weekend retreat, a multi-generational destination, or a strong investment property with outstanding rental potential. * On the main level, a cozy den with a wood-burning fireplace captures Chester River views, creating a warm and welcoming spot to relax after a day on the water. Additional living spaces provide room for groups to spread out—whether entertaining, working remotely, or simply taking a quiet moment to unwind. The primary suite offers its own private vantage point with a picture window overlooking the pool and riverfront—perfect for greeting the sunrise or watching wildlife glide across the water. * Outdoor living is where this property truly shines. Enjoy a covered patio for shaded summer crab feasts, a large deck with a stone fireplace for crisp evenings, and an in-ground pool that looks out toward the shore. With immediate water access, you’ll launch kayaks, paddle boards, and jet skis right from your backyard—ideal for embracing the river lifestyle. A two-car attached garage provides convenient storage for gear, bikes, and all the water toys. It could also be the perfect space to keep your street legal golf cart which the Town Of Chestertown now allows! * Your new home is also just a short walk from the full-service Chestertown Marina with the potential for a transferable slip—already paid through the 2026 boating season—ensuring you can enjoy hassle-free access to Chester River fun. Additionally, it's a quick ride to the Chester River Yacht & Country Club, where you can indulge in 18 holes of golf, relax by the pool, enjoy happy hour or meals at the full restaurant and bar, and partake in a host of other fantastic member benefits. * Whether you’re making it your full-time home, your getaway from the city, or your next strategic investment, this property delivers the best of Chestertown living—waterfront, walkable, and wonderfully welcoming. Embrace a lifestyle of leisure and convenience in this exceptional location.

231 Richard Dr, Chestertown

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

Selling Office: RE/MAX Chesapeake.

$905,000

Serene Waterfront Retreat on Fairlee Creek is nestled in the tranquil woods of a private community just 10 minutes from the charming shops, museums, and dining of Chestertown, and the neighboring waterfront oriented town of Rock Hall. This stunning 4-bedroom, 2-bathroom waterfront home on Fairlee Creek offers the ultimate blend of seclusion, modern luxury, and effortless outdoor living. Imagine stepping out to launch your boat or kayak, or maybe just casting a line from your own private pier and floating dock—newly installed in 2025. Step inside this thoughtfully updated retreat, where every detail whispers "move-in ready." The upper level welcomes you with an open-concept living area, dining area, and kitchen, all flowing outside onto a partial wraparound deck perfect for sunset cocktails or al fresco family meals. Cozy up by the wood-burning stove in the living room on crisp evenings, or entertain in the heart of the home with a gas range and new quartz countertops in the kitchen. The upper level bedroom invites you to start your day with private deck access and creek views. Venture downstairs to the versatile lower main level, featuring three generously sized bedrooms—one with direct waterfront vistas and french doors to the expansive lower deck and lush yard. The flexible family room adapts to your lifestyle, whether as a cozy office, kids' play haven, home gym, or media lounge, all with easy access to the outdoors. Recent enhancements shine throughout: fresh paint graces the entire house and decks (2025), while a brand-new roof installed on October 6 of this year ensures peace of mind for years to come. A new central HVAC system for the lower level, efficient mini-splits on the upper level, and bathroom remodels were all completed in September of this year. The septic system was replaced in 2021 with new BAT septic system, rated for 4 bedrooms. Outside, the magic truly unfolds. Extensive hardscaping creates an entertainer's paradise, anchored by an inviting fire pit for starry-night gatherings, barbecues, gardening, or simply soaking in the creek's serene rhythm. Your private pier and floating dock make water access effortless—launch kayaks, tie up your boat, or just watch wildlife drift by. Fairlee Creek provides a short trip direct to the Chesapeake Bay. Want a little less privacy? As a resident of this exclusive community, you unlock access to the Safe Harbor at Great Oak Landing Marina for a modest annual fee. Walk, ride a golf cart, bicycle, or drive to the marina and golf course and enjoy a resort-like lifestyle with a sparkling pool, seasonal waterfront restaurant, sandy beach, and golf course. Boat slip availability? Contact Safe Harbor directly to secure your spot at the marina. Enjoy priceless privacy in a wooded waterfront wonderland, with upgrades galore and the Chesapeake Bay lifestyle at your doorstep. Schedule your private tour today and claim your water-side paradise!

4 Beds ⋅ 2 Baths

Serene Waterfront Retreat on Fairlee Creek is nestled in the tranquil woods of a private community just 10 minutes from the charming shops, museums, and dining of Chestertown, and the neighboring waterfront oriented town of Rock Hall. This stunning 4-bedroom, 2-bathroom waterfront home on Fairlee Creek offers the ultimate blend of seclusion, modern luxury, and effortless outdoor living. Imagine stepping out to launch your boat or kayak, or maybe just casting a line from your own private pier and floating dock—newly installed in 2025. Step inside this thoughtfully updated retreat, where every detail whispers "move-in ready." The upper level welcomes you with an open-concept living area, dining area, and kitchen, all flowing outside onto a partial wraparound deck perfect for sunset cocktails or al fresco family meals. Cozy up by the wood-burning stove in the living room on crisp evenings, or entertain in the heart of the home with a gas range and new quartz countertops in the kitchen. The upper level bedroom invites you to start your day with private deck access and creek views. Venture downstairs to the versatile lower main level, featuring three generously sized bedrooms—one with direct waterfront vistas and french doors to the expansive lower deck and lush yard. The flexible family room adapts to your lifestyle, whether as a cozy office, kids' play haven, home gym, or media lounge, all with easy access to the outdoors. Recent enhancements shine throughout: fresh paint graces the entire house and decks (2025), while a brand-new roof installed on October 6 of this year ensures peace of mind for years to come. A new central HVAC system for the lower level, efficient mini-splits on the upper level, and bathroom remodels were all completed in September of this year. The septic system was replaced in 2021 with new BAT septic system, rated for 4 bedrooms. Outside, the magic truly unfolds. Extensive hardscaping creates an entertainer's paradise, anchored by an inviting fire pit for starry-night gatherings, barbecues, gardening, or simply soaking in the creek's serene rhythm. Your private pier and floating dock make water access effortless—launch kayaks, tie up your boat, or just watch wildlife drift by. Fairlee Creek provides a short trip direct to the Chesapeake Bay. Want a little less privacy? As a resident of this exclusive community, you unlock access to the Safe Harbor at Great Oak Landing Marina for a modest annual fee. Walk, ride a golf cart, bicycle, or drive to the marina and golf course and enjoy a resort-like lifestyle with a sparkling pool, seasonal waterfront restaurant, sandy beach, and golf course. Boat slip availability? Contact Safe Harbor directly to secure your spot at the marina. Enjoy priceless privacy in a wooded waterfront wonderland, with upgrades galore and the Chesapeake Bay lifestyle at your doorstep. Schedule your private tour today and claim your water-side paradise!

10050 Forrest Ln, Chestertown

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

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$872,500

Elevated coastal elegance is displayed in this waterfront perched on the banks of Mill Creek. An open floor plan, radiant floor heating, high ceilings in the great room create an ambience conducive to a luxury weekend retreat or full time residence. Water views are celebrated from nearly every inch of the home and the large windows allow for a deep connection with nature. Outdoor living is a highlight with a covered waterfront screened in porch for crab feasts, fire pit with seating providing sweeping views of Mill Creek, and expensive rear decks on each floor. Two bedrooms on the main level make one floor living a breeze including the primary with ensuite bathroom and walk in closet. Stainless steel appliances adorn the kitchen. The great room is impressive, creating a magnet effect for family and friends. Upstairs has an bonus room perfect for your home office. This is a boater's paradise with direct access to the bay within minutes but protected waters at your shoreline. The private dock includes an additional floating pier suitable for kayak excursions. The front yard has thoughtful planting, pea gravel driveway, and potting shed. Across the lane is an additional lot that comes with the property and is currently used for storage. Feel a connection with the Eastern Shore and its waterways with this high end waterfront sanctuary just 15 minutes from the shops, galleries, and restaurants of historic Chestertown.

3 Beds ⋅ 3 Baths

Elevated coastal elegance is displayed in this waterfront perched on the banks of Mill Creek. An open floor plan, radiant floor heating, high ceilings in the great room create an ambience conducive to a luxury weekend retreat or full time residence. Water views are celebrated from nearly every inch of the home and the large windows allow for a deep connection with nature. Outdoor living is a highlight with a covered waterfront screened in porch for crab feasts, fire pit with seating providing sweeping views of Mill Creek, and expensive rear decks on each floor. Two bedrooms on the main level make one floor living a breeze including the primary with ensuite bathroom and walk in closet. Stainless steel appliances adorn the kitchen. The great room is impressive, creating a magnet effect for family and friends. Upstairs has an bonus room perfect for your home office. This is a boater's paradise with direct access to the bay within minutes but protected waters at your shoreline. The private dock includes an additional floating pier suitable for kayak excursions. The front yard has thoughtful planting, pea gravel driveway, and potting shed. Across the lane is an additional lot that comes with the property and is currently used for storage. Feel a connection with the Eastern Shore and its waterways with this high end waterfront sanctuary just 15 minutes from the shops, galleries, and restaurants of historic Chestertown.

10761 Kasota Rd, Chestertown

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

Selling Office: Compass.

$855,000

Absolutely Stunning Custom-Built Home!! A Rare Opportunity You Won't Want to Miss! Welcome to this exceptional home offering nearly 3,000 square feet of beautifully designed living space, where luxury, comfort, and style come together effortlessly. Showcasing outstanding craftsmanship, thoughtful design, and high-end finishes throughout, every detail has been carefully curated to create a home that is both elegant and inviting. Featuring 4 bedrooms and 2.5 baths, this home is perfectly situated on a level 1 acre lot directly across from the scenic Chester River. From the moment you step inside, you’ll love the expansive open-concept layout, soaring ceilings, and upscale finishes throughout. The gourmet kitchen is a true showstopper, complete with a large island, sleek quartz countertops, and a hidden pantry/workstation designed for both beauty and function. The inviting stone fireplace creates the perfect focal point for gathering and entertaining. Additional highlights include spacious walk-in closets, a convenient Jack-and-Jill bath, an oversized laundry room with abundant storage, a screened-in porch with vaulted ceilings, and an oversized 2-car garage. The luxurious primary suite offers a private retreat with a spa-inspired tiled shower, while the charming front porch invites you to relax and enjoy peaceful river breezes. Upstairs, the massive fourth bedroom provides endless flexibility, ideal for a recreation room, theatre room, or home office. Located just minutes from the historic waterfront town of Chestertown, founded in 1706, you’ll enjoy charming boutiques, local restaurants, seasonal festivals, the popular Farmers Market, and endless opportunities to experience the beauty of the Chester River. Home to Washington College, the area perfectly captures the charm and lifestyle of Maryland’s Beautiful Eastern Shore. Select photos have been virtually enhanced to showcase the home’s full potential. Don’t let it slip away. Contact me today for your private tour!

4 Beds ⋅ 3 Baths

Absolutely Stunning Custom-Built Home!! A Rare Opportunity You Won't Want to Miss! Welcome to this exceptional home offering nearly 3,000 square feet of beautifully designed living space, where luxury, comfort, and style come together effortlessly. Showcasing outstanding craftsmanship, thoughtful design, and high-end finishes throughout, every detail has been carefully curated to create a home that is both elegant and inviting. Featuring 4 bedrooms and 2.5 baths, this home is perfectly situated on a level 1 acre lot directly across from the scenic Chester River. From the moment you step inside, you’ll love the expansive open-concept layout, soaring ceilings, and upscale finishes throughout. The gourmet kitchen is a true showstopper, complete with a large island, sleek quartz countertops, and a hidden pantry/workstation designed for both beauty and function. The inviting stone fireplace creates the perfect focal point for gathering and entertaining. Additional highlights include spacious walk-in closets, a convenient Jack-and-Jill bath, an oversized laundry room with abundant storage, a screened-in porch with vaulted ceilings, and an oversized 2-car garage. The luxurious primary suite offers a private retreat with a spa-inspired tiled shower, while the charming front porch invites you to relax and enjoy peaceful river breezes. Upstairs, the massive fourth bedroom provides endless flexibility, ideal for a recreation room, theatre room, or home office. Located just minutes from the historic waterfront town of Chestertown, founded in 1706, you’ll enjoy charming boutiques, local restaurants, seasonal festivals, the popular Farmers Market, and endless opportunities to experience the beauty of the Chester River. Home to Washington College, the area perfectly captures the charm and lifestyle of Maryland’s Beautiful Eastern Shore. Select photos have been virtually enhanced to showcase the home’s full potential. Don’t let it slip away. Contact me today for your private tour!

205 River Rd, Chestertown

Listing courtesy of Clark & Co Realty, LLC. Contact:

Selling Office: Cross Street Realtors LLC.

$850,000

Welcome to 492 Pear Tree Point Road: an exceptional Chester River waterfront home with unique upriver views. Spacious rooms, gorgeous cherry hardwoods, a back deck to die for, private setting, and with space to add; this home has it all! Good water depth for a dock and center console. Nearly an acre of elevated land - out of the flood zone - that backs to picturesque horse pasture. The main floor features a huge open-concept kitchen and living/dining room space which naturally flows onto the unmatched second-story wrap-around deck; perfect for crab feasts, bbq, and watching summer sunsets. Perched on the second floor is the primary suite with private Romeo and Juliet style balcony high above. Ensuite bath is unfinished but is plumbed and ready for tile and final fixtures. Walk down the sunroom to the oversized two-car garage with workshop behind and the massive unfinished loft above. With electric and insulation already in place, this space is a blank canvas ready to be turned into a fantastic rec room or 4th bedroom. Finishing the loft and primary bath would make the home over 3,000 square feet of finished space and 3/4 bedrooms and 3 fun baths. Add the final touches to make this space your own. Walkout basement has tons of storage for outdoor equipment and has a bedroom and full bath. Open House Saturday October 18, 10:00 - 2:00. Come join us.

3 Beds ⋅ 2 Baths

Welcome to 492 Pear Tree Point Road: an exceptional Chester River waterfront home with unique upriver views. Spacious rooms, gorgeous cherry hardwoods, a back deck to die for, private setting, and with space to add; this home has it all! Good water depth for a dock and center console. Nearly an acre of elevated land - out of the flood zone - that backs to picturesque horse pasture. The main floor features a huge open-concept kitchen and living/dining room space which naturally flows onto the unmatched second-story wrap-around deck; perfect for crab feasts, bbq, and watching summer sunsets. Perched on the second floor is the primary suite with private Romeo and Juliet style balcony high above. Ensuite bath is unfinished but is plumbed and ready for tile and final fixtures. Walk down the sunroom to the oversized two-car garage with workshop behind and the massive unfinished loft above. With electric and insulation already in place, this space is a blank canvas ready to be turned into a fantastic rec room or 4th bedroom. Finishing the loft and primary bath would make the home over 3,000 square feet of finished space and 3/4 bedrooms and 3 fun baths. Add the final touches to make this space your own. Walkout basement has tons of storage for outdoor equipment and has a bedroom and full bath. Open House Saturday October 18, 10:00 - 2:00. Come join us.

492 Pear Tree Point Rd, Chestertown

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

Selling Office: Benson & Mangold, LLC.

$825,000

Exceptional custom-built 2018 one-level home on 2.28 private acres in the highly sought-after Prestwick community, ideally nestled just off the Chester River Yacht & Country Club. This thoughtfully designed residence offers a seamless blend of comfort, elegance, and functionality, featuring an open-concept layout with soaring ceilings and abundant natural light throughout. The gourmet kitchen showcases timeless off-white cabinetry, granite countertops in warm earthy tones, and a coordinating backsplash, all opening effortlessly to the expansive great room anchored by a striking stone fireplace—perfect for both everyday living and entertaining. Enjoy multiple outdoor living options including a screened porch, rear porch, and patio—each offering peaceful wooded views and backing to open space for a truly private, tranquil setting that invites you to unwind and explore. The home features rich hardwood flooring, tile, fresh carpet, and fresh neutral paint throughout. The spacious primary suite, privately situated, offers a tray ceiling, two walk-in closets, and a luxurious en-suite bath, while three additional bedrooms and two full baths are thoughtfully positioned on the opposite side—ideal for guests, family, or a dedicated home office. Additional highlights include a welcoming front porch, partially finished basement with half bath and exterior access, and flexible space for recreation, hobbies, or future customization. The attached 2-car garage is complemented by a stairway off the laundry room leading to unfinished space above—perfect for expansion or storage. A standout feature is the detached custom 3-car garage equipped with a car-lift, work benches, cabinets, a mini-split system and unfinished upper level—an incredible opportunity for additional living space. Surrounded by nature, this property offers a rare combination of privacy, craftsmanship, and subtle details that are best experienced in person. Don’t miss this rare opportunity! Built by Alton E. Darling Construction.

4 Beds ⋅ 4 Baths

Exceptional custom-built 2018 one-level home on 2.28 private acres in the highly sought-after Prestwick community, ideally nestled just off the Chester River Yacht & Country Club. This thoughtfully designed residence offers a seamless blend of comfort, elegance, and functionality, featuring an open-concept layout with soaring ceilings and abundant natural light throughout. The gourmet kitchen showcases timeless off-white cabinetry, granite countertops in warm earthy tones, and a coordinating backsplash, all opening effortlessly to the expansive great room anchored by a striking stone fireplace—perfect for both everyday living and entertaining. Enjoy multiple outdoor living options including a screened porch, rear porch, and patio—each offering peaceful wooded views and backing to open space for a truly private, tranquil setting that invites you to unwind and explore. The home features rich hardwood flooring, tile, fresh carpet, and fresh neutral paint throughout. The spacious primary suite, privately situated, offers a tray ceiling, two walk-in closets, and a luxurious en-suite bath, while three additional bedrooms and two full baths are thoughtfully positioned on the opposite side—ideal for guests, family, or a dedicated home office. Additional highlights include a welcoming front porch, partially finished basement with half bath and exterior access, and flexible space for recreation, hobbies, or future customization. The attached 2-car garage is complemented by a stairway off the laundry room leading to unfinished space above—perfect for expansion or storage. A standout feature is the detached custom 3-car garage equipped with a car-lift, work benches, cabinets, a mini-split system and unfinished upper level—an incredible opportunity for additional living space. Surrounded by nature, this property offers a rare combination of privacy, craftsmanship, and subtle details that are best experienced in person. Don’t miss this rare opportunity! Built by Alton E. Darling Construction.

25475 Turnberry Ct, Chestertown

Listing courtesy of Taylor Properties. Contact:

Selling Office: Unrepresented.

$800,000

Nestled within the serene enclave of Cliffs City, this waterfront homestead offers a harmonious blend of natural beauty and water access. Spanning over 3.35 acres, the property boasts an impressive 185 feet of riverfront, providing an idyllic setting for your lifestyle. Charming brick ranch home features three bedrooms and two full baths. The heart of the home is the open family and dining room, where a cozy gas fireplace serves as a focal point set between custom built bookshelves and cabinets. Large windows throughout the home frame stunning views of the bay and river, allowing natural light to flood the space and create an inviting atmosphere. Outside, the property features a private dock site, ideal for boating enthusiasts and those who enjoy kayaking or canoeing on the tranquil waters. The rip-rap waterfront enhances the natural beauty while providing stability and protection. For those with a passion for outdoor living, the expansive lot offers ample space for gardening, entertaining, or simply enjoying the scenic vistas that surround you. Additional structures, including a 1,000 SF pole barn and two shed bays, provide practical storage solutions while maintaining the aesthetic charm of the property. Embrace the luxury of waterfront living, surrounded by nature's splendor, and create lasting memories in this exceptional property. Located only 10 miles from Historic Chestertown, you have access to shops, restaurants and the many arts and craft fairs, farmers markets and annual Tea Party celebration. This residence needs updating and the value is in the land and property. is not just a home; it's a lifestyle, where every day feels like a vacation. Home and pier are being sold strictly As-Is. Seller will not be making any repairs

3 Beds ⋅ 2 Baths

Nestled within the serene enclave of Cliffs City, this waterfront homestead offers a harmonious blend of natural beauty and water access. Spanning over 3.35 acres, the property boasts an impressive 185 feet of riverfront, providing an idyllic setting for your lifestyle. Charming brick ranch home features three bedrooms and two full baths. The heart of the home is the open family and dining room, where a cozy gas fireplace serves as a focal point set between custom built bookshelves and cabinets. Large windows throughout the home frame stunning views of the bay and river, allowing natural light to flood the space and create an inviting atmosphere. Outside, the property features a private dock site, ideal for boating enthusiasts and those who enjoy kayaking or canoeing on the tranquil waters. The rip-rap waterfront enhances the natural beauty while providing stability and protection. For those with a passion for outdoor living, the expansive lot offers ample space for gardening, entertaining, or simply enjoying the scenic vistas that surround you. Additional structures, including a 1,000 SF pole barn and two shed bays, provide practical storage solutions while maintaining the aesthetic charm of the property. Embrace the luxury of waterfront living, surrounded by nature's splendor, and create lasting memories in this exceptional property. Located only 10 miles from Historic Chestertown, you have access to shops, restaurants and the many arts and craft fairs, farmers markets and annual Tea Party celebration. This residence needs updating and the value is in the land and property. is not just a home; it's a lifestyle, where every day feels like a vacation. Home and pier are being sold strictly As-Is. Seller will not be making any repairs

4671 Cliffs City Rd, Chestertown

Listing courtesy of Cummings & Co. Realtors. Contact:

Selling Office: Unrepresented Buyer Office.

$800,000

Extraordinary development opportunity in downtown historic Chestertown. Large parcel of land (1.56+/- acres) zoned C-2 (half R1 and half R5 zoning) many permitted uses such as Muliple-Family dwelling, Townhouses, professional and business offices, non-profit museums, and others. Includes 1 building (Warehouse) and property fronts on three streets. Excellent location-- just a few blocks to the Chester River water frontage, Parks, shops, restaurants, galleries and Washington College.

206 Cannon St, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented Buyer Office.

$795,000

Discover the charm of this exquisite transitional Victorian home nestled just off the beaten path in downtown Chestertown. Built in 2011, this stunning residence boasts meticulously maintained living space, featuring an open floor plan that seamlessly blends comfort and style. The interior showcases beautiful wood floors, exposed beams, and an abundance of natural light from skylights and double-pane windows, creating an inviting atmosphere throughout. The owner's suite is located on the main floor with a beautiful new ensuite bathroom. On the second floor, you will find another living area with an additional 3 bedrooms and bathroom. Cozy up in the living area by the Vermont Castings pellet stove, perfect for creating lasting memories. The main floor laundry adds convenience to your daily routine. Step outside to enjoy the wrap-around porch, screened porch, and balcony, all overlooking the beautifully landscaped yard, ideal for entertaining or simply unwinding in your private oasis. The attached garage and paved driveway provide ample parking for you and your guests. Encapsulated crawlspace with room for storage. This home is just a short walk from historic downtown with all of the amenities like shopping, dining, farmers market and theater.

4 Beds ⋅ 3 Baths

Discover the charm of this exquisite transitional Victorian home nestled just off the beaten path in downtown Chestertown. Built in 2011, this stunning residence boasts meticulously maintained living space, featuring an open floor plan that seamlessly blends comfort and style. The interior showcases beautiful wood floors, exposed beams, and an abundance of natural light from skylights and double-pane windows, creating an inviting atmosphere throughout. The owner's suite is located on the main floor with a beautiful new ensuite bathroom. On the second floor, you will find another living area with an additional 3 bedrooms and bathroom. Cozy up in the living area by the Vermont Castings pellet stove, perfect for creating lasting memories. The main floor laundry adds convenience to your daily routine. Step outside to enjoy the wrap-around porch, screened porch, and balcony, all overlooking the beautifully landscaped yard, ideal for entertaining or simply unwinding in your private oasis. The attached garage and paved driveway provide ample parking for you and your guests. Encapsulated crawlspace with room for storage. This home is just a short walk from historic downtown with all of the amenities like shopping, dining, farmers market and theater.

201 Radcliffe Dr, Chestertown

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

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$775,000

Handsome farmhouse on 36 acres. House maintains much of its original character. Spacious rooms and beautiful views.

4 Beds ⋅ 3 Baths

Handsome farmhouse on 36 acres. House maintains much of its original character. Spacious rooms and beautiful views.

8293 Brices Mill Rd, Chestertown

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

Selling Office: Unrepresented Buyer Office.

$750,000

Nestled along the tranquil western shore of the Chester River, this beautiful townhome in Chester River Landing offers an unparalleled waterfront living experience with direct water access and captivating water views. Just a short stroll from the historic heart of Chestertown, MD, it combines modern luxury with timeless charm. This elegant 3-bedroom, 2.5-bath residence is designed to maximize comfort and style. The spacious living areas are bathed in natural light, enhancing the serene ambiance of this waterfront haven. The open-plan living and dining areas flow seamlessly into the well-appointed kitchen, equipped with top-of-the-line appliances and ample storage. The master bedroom is a true retreat, with easterly river views and an ensuite bath. The additional bedrooms are generously sized, perfect for family or guests. The 3.5 baths are elegantly designed, featuring modern fixtures and finishes. One of the standout features of this home is its perfect vantage point for watching the daily sunrise. Imagine starting your day with a cup of coffee on the balcony, as the first light of dawn reflects off the calm waters of the Chester River while rowing teams begin their daily workout. Whether you're seeking a peaceful waterfront retreat or a picturesque spot to entertain, this townhome offers it all. The community amenities of Chester River Landing further enhance the lifestyle, with walking paths, swimming pool, private pier with available boat slips for purchase or lease, outdoor grilling and beautifully landscaped common areas. Discover the unique blend of history, luxury, and natural beauty at this waterfront home on the Chester River.

3 Beds ⋅ 4 Baths

Nestled along the tranquil western shore of the Chester River, this beautiful townhome in Chester River Landing offers an unparalleled waterfront living experience with direct water access and captivating water views. Just a short stroll from the historic heart of Chestertown, MD, it combines modern luxury with timeless charm. This elegant 3-bedroom, 2.5-bath residence is designed to maximize comfort and style. The spacious living areas are bathed in natural light, enhancing the serene ambiance of this waterfront haven. The open-plan living and dining areas flow seamlessly into the well-appointed kitchen, equipped with top-of-the-line appliances and ample storage. The master bedroom is a true retreat, with easterly river views and an ensuite bath. The additional bedrooms are generously sized, perfect for family or guests. The 3.5 baths are elegantly designed, featuring modern fixtures and finishes. One of the standout features of this home is its perfect vantage point for watching the daily sunrise. Imagine starting your day with a cup of coffee on the balcony, as the first light of dawn reflects off the calm waters of the Chester River while rowing teams begin their daily workout. Whether you're seeking a peaceful waterfront retreat or a picturesque spot to entertain, this townhome offers it all. The community amenities of Chester River Landing further enhance the lifestyle, with walking paths, swimming pool, private pier with available boat slips for purchase or lease, outdoor grilling and beautifully landscaped common areas. Discover the unique blend of history, luxury, and natural beauty at this waterfront home on the Chester River.

212 Landing Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

Selling Office: Unrepresented Buyer Office.

$749,500

3 Beds ⋅ 3 Baths

6 Byford Ct, Chestertown

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

Selling Office: Cross Street Realtors LLC.

$740,000

Tremendously charming historic house, sensitively restored, a short distance from Great Oak Marina. Beautiful original 18th century pine floors, mantel pieces, six-panel doors and built-in cupboard. House was originally two small historic houses located in the village of Church Creek, Dorchester County, Maryland, moved to current location ca.1980. Private yard and garden. Chestertown and Rock Hall nearby. House has upgraded electric and Best Available Technology (BAT) septic system. Well water filtration system. First story bedroom and guest bedroom, additional bedrooms up. Modern kitchen with new Whirlpool brand stainless steel appliances, gas cookstove opening to family/entertaining area. Formal parlor with gas fireplace. Sunroom with skylights, tile floor, ceiling fan, overlooking garden. Most rooms have plantation shutters. Spacious closets. New recessed lights. If owner wants to join marina with pool and beach, it is believed that current fee is $100; additional dock fee if new owner has a boat and desires slip. $350/year road maintenance.

4 Beds ⋅ 3 Baths

Tremendously charming historic house, sensitively restored, a short distance from Great Oak Marina. Beautiful original 18th century pine floors, mantel pieces, six-panel doors and built-in cupboard. House was originally two small historic houses located in the village of Church Creek, Dorchester County, Maryland, moved to current location ca.1980. Private yard and garden. Chestertown and Rock Hall nearby. House has upgraded electric and Best Available Technology (BAT) septic system. Well water filtration system. First story bedroom and guest bedroom, additional bedrooms up. Modern kitchen with new Whirlpool brand stainless steel appliances, gas cookstove opening to family/entertaining area. Formal parlor with gas fireplace. Sunroom with skylights, tile floor, ceiling fan, overlooking garden. Most rooms have plantation shutters. Spacious closets. New recessed lights. If owner wants to join marina with pool and beach, it is believed that current fee is $100; additional dock fee if new owner has a boat and desires slip. $350/year road maintenance.

10230 John Carvill Rd, Chestertown

Listing courtesy of Shoreline Realty. Contact:

Selling Office: Cross Street Realtors LLC.

$730,000

Experience the warmth and charm of in-town living in this beautiful residence in Chestertown's Historic District. Just a few blocks from the waterfront, shops, galleries, and restaurants, it offers the perfect balance of walkability and tranquility on one of the district's quietest streets. The thoughtfully designed layout makes excellent use of every square foot, while tasteful updates fill the home with natural light. A spacious screened porch extends from the dining room, offering a peaceful place to relax and enjoy the character of the neighborhood. The fenced backyard is a gardener's dream, featuring lush landscaping, vibrant plantings, and beautiful hardscaping that create a private outdoor sanctuary. A rear entrance with off-street parking adds everyday convenience while preserving the home's charming streetscape. This exceptional historic property offers an outstanding lifestyle less than two hours from Washington, DC, and Philadelphia.

4 Beds ⋅ 3 Baths

Experience the warmth and charm of in-town living in this beautiful residence in Chestertown's Historic District. Just a few blocks from the waterfront, shops, galleries, and restaurants, it offers the perfect balance of walkability and tranquility on one of the district's quietest streets. The thoughtfully designed layout makes excellent use of every square foot, while tasteful updates fill the home with natural light. A spacious screened porch extends from the dining room, offering a peaceful place to relax and enjoy the character of the neighborhood. The fenced backyard is a gardener's dream, featuring lush landscaping, vibrant plantings, and beautiful hardscaping that create a private outdoor sanctuary. A rear entrance with off-street parking adds everyday convenience while preserving the home's charming streetscape. This exceptional historic property offers an outstanding lifestyle less than two hours from Washington, DC, and Philadelphia.

210 N Queen St, Chestertown

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

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$725,000

Built in 1780/1840, "Highcroft" is in the heart of the Historic District near the Chester River. A rare in-town property that offers a 2-car garage with a second floor and a long driveway for tons of off-street parking. 3 bedrooms, 4 full baths and 1 half bath. Primary bedroom has his and hers private baths. 8.2 kw solar array on the garage. EV level 2 charger. Easy room flow from front to back for entertaining. Just steps to restaurants, bars, and shops. This is an ultra efficient "green" house.

3 Beds ⋅ 5 Baths

Built in 1780/1840, "Highcroft" is in the heart of the Historic District near the Chester River. A rare in-town property that offers a 2-car garage with a second floor and a long driveway for tons of off-street parking. 3 bedrooms, 4 full baths and 1 half bath. Primary bedroom has his and hers private baths. 8.2 kw solar array on the garage. EV level 2 charger. Easy room flow from front to back for entertaining. Just steps to restaurants, bars, and shops. This is an ultra efficient "green" house.

407 High St, Chestertown

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

Selling Office: Cross Street Realtors LLC.

$705,000

***OFFER DEADLINE FOR HIGHEST & BEST IS MONDAY, 8/10 @ 5PM--SELLER RESERVES THE RIGHT TO ACCEPT AN OFFER AT ANY POINT PRIOR TO THE DEADLINE AT THEIR SOLE DISCRETION*** This exceptional property offers classic charm, thoughtful updates, and a highly desirable location in a neighborhood where homes rarely become available. No trendy updates here-timeless, classic elegance and warmth invite you home and will stand the test of time. Situated on a beautifully landscaped 0.88-acre lot with mature trees, this home is just minutes to the Country Club (close enough to walk) and a few minutes drive to downtown Chestertown. The main level features a spacious and well-designed layout with 3 bedrooms, 2 full baths, and 1 half bath. The renovated kitchen is complete with a large island, new granite countertops, lovely cabinetry, gas cooking, under-cabinet lighting, and recessed lighting. A bright dining room with custom built-ins and bay window flows into the formal living room with French doors. The great room offers a warm and inviting space with a gas fireplace, beautiful brick surround and chimney hugged by timeless built-ins on each side, with another bright bay window. The main-level primary suite includes access to the rear deck, a renovated en-suite bath with pocket door, and a walk-in closet. Two additional bedrooms, a full hall bath, laundry room, and a convenient half bath complete the main level. The second level provides incredible flexibility with two finished rooms, a bonus room that could serve as a potential 4th bedroom and another room, ideal for an office, recreation, or hobby space. An additional half bath is located on the upper level, and an extensive unfinished storage space & room is awaiting your vision. Additional features include a basement and crawlspace, water softener system, reverse osmosis kitchen faucet, sump pump, and dehumidifier, attached 2 car garage & potting shed, just to name a few. Outdoor living is equally impressive with a covered front porch, large rear deck, lawn irrigation, and meticulously maintained landscaping. A rare opportunity in a sought-after location—schedule your showing soon. Please do not enter the property without an appointment. Most of the furnishings and decor are negotiable and available for purchase. Being Sold As-Is.

3 Beds ⋅ 4 Baths

***OFFER DEADLINE FOR HIGHEST & BEST IS MONDAY, 8/10 @ 5PM--SELLER RESERVES THE RIGHT TO ACCEPT AN OFFER AT ANY POINT PRIOR TO THE DEADLINE AT THEIR SOLE DISCRETION*** This exceptional property offers classic charm, thoughtful updates, and a highly desirable location in a neighborhood where homes rarely become available. No trendy updates here-timeless, classic elegance and warmth invite you home and will stand the test of time. Situated on a beautifully landscaped 0.88-acre lot with mature trees, this home is just minutes to the Country Club (close enough to walk) and a few minutes drive to downtown Chestertown. The main level features a spacious and well-designed layout with 3 bedrooms, 2 full baths, and 1 half bath. The renovated kitchen is complete with a large island, new granite countertops, lovely cabinetry, gas cooking, under-cabinet lighting, and recessed lighting. A bright dining room with custom built-ins and bay window flows into the formal living room with French doors. The great room offers a warm and inviting space with a gas fireplace, beautiful brick surround and chimney hugged by timeless built-ins on each side, with another bright bay window. The main-level primary suite includes access to the rear deck, a renovated en-suite bath with pocket door, and a walk-in closet. Two additional bedrooms, a full hall bath, laundry room, and a convenient half bath complete the main level. The second level provides incredible flexibility with two finished rooms, a bonus room that could serve as a potential 4th bedroom and another room, ideal for an office, recreation, or hobby space. An additional half bath is located on the upper level, and an extensive unfinished storage space & room is awaiting your vision. Additional features include a basement and crawlspace, water softener system, reverse osmosis kitchen faucet, sump pump, and dehumidifier, attached 2 car garage & potting shed, just to name a few. Outdoor living is equally impressive with a covered front porch, large rear deck, lawn irrigation, and meticulously maintained landscaping. A rare opportunity in a sought-after location—schedule your showing soon. Please do not enter the property without an appointment. Most of the furnishings and decor are negotiable and available for purchase. Being Sold As-Is.

7903 Radcliffe Rd, Chestertown

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

Selling Office: Unrepresented.

How much is your home worth?

How much is your home worth?