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$3,995,000
3 Beds 4 Baths
Every so often a property like 240 Round Top Landing Road, Chestertown hits the market that checks all the boxes. This Chester River waterfront estate is situated on 10 acres , offering deep water, pier, 25' x 50 ' in-ground pool, screened porch , 3 bedroom/3.5 bath main house and a carriage house. The architectural design and the superb craftsmanship are evident as soon as you enter the driveway. Beautiful trees(Peach,Pear, Pines, Poplars, Sycamores, Magnolias' Crepe Myrtles) enhance the park-like setting. Notable features are geo-thermal heat; gas and wood burning fireplaces, chef's kitchen; first floor spacious primary bedroom suite , and open living areas. As far as the exterior, the stucco siding is either over brick or block so no stucco is over frame. Some poplar siding on main house and cedar siding on carriage house.

240 Round Top Landing Rd, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 673-3344

$2,700,000
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 wellness center, complete with a café, wellness-related offices, and a spectacular studio. 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 fourth 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:

$1,870,000
Radcliffe Mill presents an exceptional opportunity for a savvy investor looking for value and a one-of-a-kind investment with endless possibilities. Transformed in a major restoration in 2007 The Mill building features four floors of office space and a 70+ seat restaurant. 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 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 and has a long-term lease in place. All of the major restaurant equipment is included in the sale. The 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 being offered for sale separately, or the entire property can be purchased as a package. The sale of either 860 or 870 High Street individually is contingent on a lot line adjustment. Buyers requesting additional information must sign a Non-Disclosure Agreement.

870 High St, Chestertown

Listing courtesy of Taylor Properties. Contact:

$1,650,000
4 Beds 5 Baths
SMITH-RINGGOLD HOUSE. ca. 1750 OWNER IS MEETING THE MARKET for this rare property WITH PRICE NOW AT $1,6500,000. This exceptional property is a rare find: an authentic waterfront 18th century home with 21st century comfort in heart of Historic Districtnof Chestertown on Maryland's Eastern Shore. Originally a merchant’s home , the Smith-Ringgold house has been tastefully modified representing four defined periods and enlarged over the course of its 250-year history. William Ringgold added rooms toward the River in about 1759 that doubled the space. (Often, one would find 18th c. additions such as this creating a telescope style design. ) The present owner took two-years to restore the home from foundation to attic. A river-side sun-porch/breakfact room was added. ,The cedar shingle roof, , plumbing, wiring, heat and A/C systems were added or replaced. Wood floors throughout the house have been beautifully restored. Modern storm windows are energy efficient and all but eliminate street sounds. Aside from your own personal touches, this house awaits our arrival anf iss prepared for the next century. The ground floor has a large double parlor, serene sitting room, formal dining room, breakfast room, and a stunning Chef’s kitchen. An important feature is the hand painted dining room mural by noted artist Jack Schroeder. The front hall, redesigned in about 1860, replaced a steep stairway with a grand and gracefully curving staircase. The second floor contains three large en-suite bedrooms and a laundry room that is also accessible from the kitchen via a “secret” staff stairway. The third floor has a large sitting room, bathroom, and fourth bedroom. A setion of the home’s original c. 1750 roof has been restored forming a unique design element. The backyard was extensively terraced, probably in the late 1700s, in descending levels down to the Chester River eliminating the fear of flooding. The free-standing brick garage dates from the early 20th century, when car garages replaced horse barns. This structure could easily be repurposed as an artist’s studio or home workshop. A wide driveway area provides additional off-street parking. Truly an inviting residence for intimate family evenings or grand parties. Perfect setting for one's collection of antiques or for the simplicity of contemporary furniture which emphasizes the wonderful architecture. CHESTERTOWN IN THE COUNTY OF KENT Chestertown was founded in 1706 on the broad Chester River and served as an important shipping hub for trade with England and between the colonies. As the U.S. population center moved westward, Kent County settled into two hundred years of quiet agricultural and commercial fishing activities. Chestertown is home to a surprisingly large number of elegant, historical Georgian homes as well as Victorian “painted ladies.” With a population of 5,600, Chestertown is only an hour from Annapolis or Wilmington, about two hours from Baltimore, Philadelphia or Washington, and under four hours from New York City. Chestertown in the County of Kent is "a place where one would rather be". Centrally located Washington College (founded in 1782 with the personal support of George Washington) provides Chestertown a mix of athletic competitions, music and drama, adult education, and visiting speakers. The town boasts a weekly Farmers Market, excellent coffee bars, restaurants, and art galleries—but no big box stores. The Chester River Yacht & Country Club offers an 18-hole golf course as well as a sailing program. The whole community supports major events like the annual Tea Party, commemorating a Revolutionary War protest; a Dickens Christmas Street Fair; and Down-rigging Weekend, when tall ships offer tours and sails on the Chester River. Today, Chestertown, is a vibrant mix of old families, newcomers, college students, full time residents with children, and involved weekenders.

201 N Water St, Chestertown

Listing courtesy of Maryland Heritage Properties. Contact: (443) 480-7342

$1,449,000
3 Beds 4 Baths
Introducing a stunning new construction waterfront home in Chestertown's prestigious waterfront community, Chester River Landing. Hands down, one of the best lots in the community! The Schooner model is an exquisite three-bedroom, three-and-a-half-bath home that offers luxurious living and breathtaking, panoramic views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious layout provides ample room for relaxation and entertaining. With high-end finishes and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Little Harbor Way Unit #1, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665

$1,300,000
5 Beds 5 Baths
Step into a world of timeless elegance and tranquility with this meticulously maintained retreat. As you turn into the Fairgale Subdivision, it feels as though you are entering an estate, with majestic trees lining both sides of the paved road, creating a sense of grandeur and privacy. Nestled on the shores of an oversized pond, this exquisite home offers not only stunning views but also exclusive access to a community dock and dedicated boat slip with a lift onto Fairlee Creek. Originally built in 2000 and impeccably maintained and updated, this home welcomes you with a beautifully designed foyer that sets the bar for living beautifully. The living room, open to a gracious dining area, exudes warmth and hospitality, making it the perfect setting for gatherings with loved ones. French doors beckon you to the covered patio, where you can bask in the serene ambiance and enjoy the sights and sounds of nature. Below, the guinite pool invites you to relax and unwind, surrounded by ample space for poolside lounging and entertaining. The main level boasts four bedrooms, including a luxurious owner's suite complete with a cozy gas fireplace and direct access to the pool area. The master bath is a sanctuary in itself, featuring separate vanities, a spacious walk-in shower, a soothing soaking tub, and generous storage space. The second bathroom, versatile in its design, offers built-in bookshelves and two closets, making it ideal for use as an office or guest suite. A convenient half bath, with access to the pool, adds to the home's functionality and convenience. The recently updated kitchen is a Cook's delight, equipped with an island, ample storage, and all the necessary appliances. Adjacent to the kitchen, the family room beckons with built-ins, a fireplace, and abundant natural light, creating a cozy yet inviting atmosphere. The Florida Room, bathed in sunlight, offers a perfect spot for plants and relaxation, with seamless access to the pool area. Two additional bedrooms, one with an attached sitting room, and a full bath complete the main level, ensuring comfort and convenience for all. Downstairs, a newly added bedroom and bathroom, along with a spacious great room, provide endless possibilities for entertainment and recreation. The expansive storage room offers potential for additional living space or customization to suit your needs. Upstairs, the attic boasts a large cedar room for storage, with even more space available if needed. The quality of construction is evident throughout, ensuring durability and longevity for years to come. Don't miss this opportunity to experience the beauty and serenity of waterfront living at its finest. Schedule a viewing today and make this exquisite property your own slice of paradise in this great neighborhood.

22956 Fairgale Farm Ln, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$949,900
4 Beds 4 Baths
Introducing a stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. The Sultana model is an exquisite four-bedroom, two-and-a-half-bath home that offers luxurious living and breathtaking views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious layout provides ample room for relaxation and entertaining. With high-end finishes and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Landing Ln Unit #25, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665

$879,000
4 Beds 4 Baths
A stunning renovation in the historic district! This stately brick colonial overlooks the meticulous campus green at Washington College; a view that invites a walk to downtown Chestertown, and a location that gives you a front row seat to college activities and events. It is also one short block to the University of Maryland Shore Medical Center. A desirable rear alley, provides access to the home's private off-street parking space and the carriage-styled garage, which can accommodate a SUV. Located on the first floor off the center hall, is the living room, dining room, kitchen, den/office, half bath, all- season sun room, and inside stairs to the full basement, The new custom kitchen showcases an individually handcrafted brick floor and an imported Spanish tiled backsplash. Wrap around natural lighting, open shelving, oversized island and walk in-pantry make this kitchen one of a kind, and completes the first floor. The second floor begins with the original grand stairway and a cozy sitting area in the window nook at the end of the catwalk. The primary bedroom comes with a five piece luxury en-suite bath, while two additional bedrooms share a full bathroom off the landing. The dedicated laundry room, also on the second floor, has storage cabinets, room for ironing and folding and a cleaning supply niche.  The third floor garret-studio apartment completes the living areas inside this home. This spacious studio has a full bathroom, dedicated cooking & eating area and independent climate control. A comfortable sitting area and separate sleeping space, and separate desk space round out this studio. There is also a  full basement of approximately 1100 square ft with both interior access and a highly coveted exterior access. 7.5 foot high basement ceilings, provide an excellent opportunity to design an additional apartment, fitness studio, family room, wood shop etc.  Exterior and mechanical upgrades include: a new roof, gutters & downspouts, a new front landing with oversized walkways and raised brick landscape beds. Significant wiring upgrades include a new electrical service and wiring for new electrical components. Plumbing upgrades include a new main shut off valve and a new water line between the house and street. Replacement of most of the interior plumbing was done to accommodate updated fixtures. The one-car, carriage styled garage has been placed for optimum versatility. It makes a charming extension of the outdoor entertaining space to effortlessly plan for changeable Chesapeake-country weather. Simply move the car, open the barn doors, turn on the the oversized crystal chandelier and the tone is set for gatherings protected from the elements! With the double barn doors opened,  the terraced courtyard can be incorporated into any event. This property is fully fenced & gated providing privacy for outdoor activities and security for family pets. This brick center-hall colonial  has been extensively renovated and is turn-key!  Square footage is estimated: buyer to verify. A complete upgrade record is available upon request. Talk to your agent about possible owner financing on this home.

307 Washington Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$864,000
3 Beds 3 Baths
Welcome home to this stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. This exquisite three-bedroom, two-and-a-half-bath home offers luxurious living and breathtaking views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious, open floorplan layout provides ample room for relaxation and entertaining. With high-end finishes including granite countertops, luxury vinyl and tile flooring, Hardie plank siding, stainless steel appliances, etc. and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Little Harbor Way Unit #19, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665

$860,000
The Annex/Seed House at Radcliffe Mill is a stunning, one of a kind space. Fully restored in 2007, with additional work done in 2017 to add a built out cafe space, The Annex/Seed House now houses a wellness center, complete with a café, wellness-related offices, and a spectacular studio. The property's zoning allows for a wide array of uses. Keep the space in its current configuration or build out into a full scale restaurant or transform it into office space or apartments. 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. Five of The Seed House offices are on the ground floor, with a sixth office on the second floor, along with additional storage and laundry facilities. 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 as well as together. The sale of 860 High Street alone is contingent on a lot line adjustment. Tax amounts will be adjusted upon completion of the lot line adjustment. Buyers requesting additional information must sign a Non-Disclosure Agreement.

860 High St, Chestertown

Listing courtesy of Taylor Properties. Contact:

$854,000
3 Beds 3 Baths
Welcome home to this stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. This exquisite three-bedroom, two-and-a-half-bath home offers luxurious living and breathtaking views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious, open floorplan layout provides ample room for relaxation and entertaining. With high-end finishes including granite countertops, luxury vinyl and tile flooring, Hardie plank siding, stainless steel appliances, etc. and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Little Harbor Way Unit #20, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665

$805,000
3 Beds 4 Baths
Check out Chester River Landing's newest construction! This three bedroom, three and a half bath, townhouse is a spacious end unit with incredible views of the Chester River and is built with the finest finishes. The main first level includes a large open floorplan design great for socializing and entertaining guests and a study off of the front foyer. Upstairs includes three bedroom suites all with their own bath. The primary bedroom has panoramic views of the river and sliding glass doors to the balcony. This home is built with an elevator shaft for future use if necessary. Enjoy all that the community has to offer, clubs and social gatherings, bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short ways up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Landing Ln Unit #11, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665

$799,000
3 Beds 3 Baths
Welcome home to this stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. This exquisite three-bedroom, two-and-a-half-bath home offers luxurious living and breathtaking views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious, open floorplan layout provides ample room for relaxation and entertaining. With high-end finishes including granite countertops, luxury vinyl and tile flooring, Hardie plank siding, stainless steel appliances, etc. and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Landing Ln Unit #40, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665

$785,000
3 Beds 3 Baths
Welcome home to this stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. This exquisite three-bedroom, two-and-a-half-bath home offers luxurious living and breathtaking views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious, open floorplan layout provides ample room for relaxation and entertaining. With high-end finishes including granite countertops, luxury vinyl and tile flooring, Hardie plank siding, stainless steel appliances, etc. and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Landing Ln Unit #41, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665

$725,000
3 Beds 3 Baths
Welcome home to this stunning new construction in Chestertown's prestigious waterfront community, Chester River Landing. This exquisite three-bedroom, two-and-a-half-bath home offers luxurious living and breathtaking views of the Chester River. Nestled in a serene setting, this property blends modern design with coastal charm. The spacious, open floorplan layout provides ample room for relaxation and entertaining. With high-end finishes including granite countertops, luxury vinyl and tile flooring, Hardie plank siding, stainless steel appliances, etc. and attention to detail, this home promises a lifestyle of comfort and sophistication. Immerse yourself in the beauty of the waterfront community, enjoying the bbq/picnic area, shell walking paths, community pool and the deep-water community dock. The Chester River Yacht and County Club is a short way up the road to play a round of golf, fine dining and social events or head into historic downtown Chestertown just minutes away for shopping, restaurants, plays, farmer's markets and more!

Landing Ln Unit #37, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665

$699,999
3 Beds 4 Baths
Welcome to 101 Landing Lane, an exquisite residence offering exceptional living in the prestigious Chester River Landing Community. Boasting an expansive 3,300 square feet of meticulously designed living space, this home features luxurious amenities and elegant finishes across three levels, ensuring comfort and style at every turn. Step inside to discover the warmth of hardwood floors that flow seamlessly throughout the home. The main level features a spacious guest bedroom and a full bath, perfect for accommodating visitors with style and ease. A well-appointed study on this level offers a quiet retreat for work or relaxation, ensuring a versatile and functional living space. The lower-level deck is perfect for relaxing with a good book, overlooking the scenic community pond, and the attached one-car garage provides parking and storage space. The second level's open floor plan integrates the kitchen, living room, and dining room, creating an inviting space ideal for modern living and entertaining, with hardwood floors throughout. The gourmet kitchen is a chef’s dream, showcasing rich wood cabinets, stone countertops, and stainless steel appliances. The living and dining areas extend effortlessly to an upper-level balcony, perfect for al fresco dining and providing serene views of the community pond. The primary bedroom on this level offers a luxurious sanctuary with a large walk-in closet and beautifully finished bathroom The third level is designed for leisure and entertainment. Here, you’ll find an additional bedroom and a versatile game room, perfect for family fun or casual get-togethers. The game room can be adapted to suit your lifestyle needs, whether as a media room, playroom, or hobby space. Residents enjoy easy water access and exclusive use of the community’s private dock and swimming pool. The swimming pool offers a refreshing escape during the warmer months, perfect for relaxation and recreation. Experience the epitome of elegant living in a vibrant and friendly community in this move-in ready home. Don’t miss the opportunity to make 101 Landing Lane yours. Schedule a private tour today and discover all the exceptional features this property has to offer.

101 Landing Ln Unit #39, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453

$695,000
3 Beds 2 Baths
Eastern Shore of Maryland Waterfront Cottage is perched on the banks of Rosin Creek in Queen Anne’s County. Cozy, comfortable home welcomes you with wrap-around waterviews in a serene wooded setting. With convenient single level living, the three bedroom one-and-half bath home offers an open flowing floorplan bright with natural light and custom wood detail. Relax and enjoy views from the large screened porch or stroll down to your dock and floating dock for boating, fishing and water activities. Located in the popular waterfront community of Chester Harbor you are a walk away from the community dock and picnic area. This property is a little gem located just 3-miles from downtown historic Chestertown. Chestertown is located about 90 minutes from Washington, D.C. and Philadelphia. Founded in 1706, it is set on the banks of the Chester River and is home to Washington College and the University of Maryland Shore Medical Center. The walking town features beautiful period homes, sought after shops, galleries, live theater and waterfront park. Dining options include an oyster bar, bakery, cafes, luncheonette and fine dining restaurants. The landing at the foot of High Street leads to the Chester River Walk where you can take a river cruise on the Chester River Packet. Annual events include the Chestertown Tea Party and Tall Ship Downrigging Weekend. Residents and visitors alike enjoy the vibrant arts community, the Saturday Farmers/Artisan Market, waterfront park, rails-to-trails and water activities.

415 Fairview Dr, Chestertown

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

$515,000
4 Beds 3 Baths
Welcome to a captivating opportunity to reside in the idyllic neighborhood of The Grove in picturesque Queen Anne's County. Prepare to be enchanted by this charming abode, where every detail exudes warmth and comfort. Step inside and be greeted by the timeless elegance of hardwood floors and plush carpeting, inviting you to kick off your shoes and make yourself at home. The heart of the main floor boasts a cozy gas fireplace, creating a cozy ambiance perfect for intimate gatherings or quiet evenings curled up with a good book. With four bedrooms and 2.5 baths, there's ample space for your family to spread out and relax. The open floor plan seamlessly connects the living spaces, allowing for effortless flow and easy entertaining. The kitchen, a culinary haven, beckons with its modern amenities and ample counter space, inspiring culinary creativity and culinary delights. Recent updates abound in this haven of comfort and style, including new skylights that bathe the interiors in natural light, and a spacious deck where you can savor morning coffee or evening cocktails while overlooking your fenced backyard and the serene vistas of rolling farmlands. Venture downstairs to discover a sprawling recreation room, offering endless possibilities for entertainment and relaxation. Whether you envision a home theater, a game room, or a fitness area, this versatile space is ready to fulfill your every need. A separate office provides a quiet retreat for work or study, while an additional bedroom offers flexibility for guests or extended family. Storage woes are a thing of the past, with plenty of space to stow away your belongings or unleash your creativity to reimagine the possibilities of each room. Embrace the quintessential charm of country living while still enjoying the convenience of modern amenities. The Grove offers a tranquil escape from the hustle and bustle of city life, with its tree-lined streets and sense of community. Don't miss your chance to make this enchanting retreat your own. Schedule a viewing today and embark on a journey to a life of comfort, convenience, and timeless elegance in The Grove.

112 Sheaffer Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$498,000
2 Beds 3 Baths
Welcome to your tranquil retreat at Orchard Hill, where modern sophistication meets peaceful living on 1.89 acres of beautifully landscaped grounds. This stunning Cape Cod style home offers an abundance of amenities and thoughtful details throughout. As you step inside, you're greeted by the grandeur of vaulted ceilings that create an open and airy atmosphere. The ground floor primary bedroom provides convenience and luxury, complete with a upgraded kitchen featuring granite countertops, quality stainless steel appliances, an island with a gas cooktop, and a built-in wine refrigerator. The primary bedroom is a true sanctuary, featuring a luxury primary bath with a jetted tub and a stylish tile shower with glass doors. The main level's open layout is perfect for entertaining, with the added convenience of a bar with a sink. The second floor offers a guest bedroom, a full bath, and a loft that could easily be converted into a third bedroom or utilized as a versatile space according to your needs. Outdoor living is equally impressive, with a screened porch, large composite deck with a retractable canopy, a gazebo, and beautiful English cottage gardens featuring many native plants. The expansive outdoor space is perfect for gardening, outdoor activities, or simply enjoying the serene surroundings. Backing to trees and farmland, this property provides a peaceful backdrop and ample privacy. It's truly a must-see for those seeking a blend of modern luxury and peaceful countryside living. Schedule a showing today to experience the beauty and serenity of this exceptional property at Orchard Hill.

8757 Orchard Dr, Chestertown

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

$497,000
Last waterfront parcel available in subdivision! Discover the opportunity to claim your own piece of history with this 2.3 acre waterfront parcel on Truslow Farm, the beloved namesake of Truslow Rd., now available for sale for the first time. Situated amidst the serene beauty of this cherished farm, these parcels represent a few of the last untouched waterfront canvases on the Chester River, eagerly awaiting your imagination to bring them to life. For years, the Truslow family has nurtured this land, and now it's your turn to write the next chapter. These parcels offer the perfect opportunity to build your dream home and waterfront escape. Located just across the river from the vibrant events of the Sultana, Downrigging, Tea Party festivals, and more, you'll have a front-row seat to the action from your comfortable spot across the river. Immerse yourself in the excitement while still enjoying the tranquility of your own private retreat. Don't miss out on this exclusive opportunity to own a piece of Truslow Farm and become part of its storied history. Schedule your showing today and start envisioning the endless possibilities that await on this remarkable waterfront property, exclusively offered for the first time.

Truslow Farm Ln Unit #LOT 2, Chestertown

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

$450,000
4 Beds 3 Baths
This beautiful custom home on an acre of land has 4 Beds and 2.5 baths. There is an eat-in-Kitchen with granite countertops that is completed by the Maple Wood Island, Gas cooking, and stainless steel appliances, soft close cabinets and 2 pantry's. This home has a Large living and Dining room too! The 'Florida Sunroom' allows could be an office or a place to read a book in the sunshine and the double doors lead out to your fenced in yard. Acacia hardwood floors throughout! This home boasts a new water treatment system (owned) and gutter guard system so you don't have to worry about all the trees that make this home your private oasis in the woods. Upstairs the primary bedroom has a beautiful ensuite bath with separate jetted tub, shower and a double vanity. It also has walk in closest with a window as well as an additional large closet. There is a dedicated laundry room upstairs, ample closet space and 3 other bedrooms that share an updated bathroom. Don't forget the garage and storage room with 2 decks outside! Schedule your showing today!

8500 Broad Neck Rd Sw, Chestertown

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005

$425,000
7 Beds 4 Baths
Looking for something truly special? Don't miss this unique offering, located in the vibrant heart of Chestertown's Historic and Arts & Entertainment Districts! Boasting a legacy of over half a century under the stewardship of one devoted family, this multi-family property presents a rare opportunity for visionary investors and passionate renovators alike. Situated on a generous lot, steeped in the rich history of Chestertown and prominently featured on historic maps as the Laurence Lots, this property offers a canvas brimming with potential. Whether you envision revitalizing it into a majestic single-family residence or retaining its current configuration with a townhouse on one side and two apartments on the other, the possibilities are boundless. While the property stands as a testament to enduring charm and character, it's essential to note that significant settling has occurred over the years. As such, unlocking its full potential will necessitate considerable renovation efforts. This property is a bona fide fixer-upper and is exclusively offered in its current "as is" condition, awaiting the transformative touch of its next custodian. With its prime location , this property represents not only an investment opportunity but a chance to become part of Chestertown's storied legacy. Seize the chance to breathe new life into this home and craft a future brimming with possibility. Embrace the challenge, unleash your creativity, and make your mark on Chestertown's captivating tapestry of history and culture. Schedule your viewing today and prepare to embark on an unforgettable journey of restoration and renewal!

349 High St, Chestertown

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

$425,000
Looking for something truly special? Don't miss this unique offering, located in the vibrant heart of Chestertown's Historic and Arts & Entertainment Districts! Boasting a legacy of over half a century under the stewardship of one devoted family, this multi-family property presents a rare opportunity for visionary investors and passionate renovators alike. Situated on a generous lot, steeped in the rich history of Chestertown and prominently featured on historic maps as the Laurence Lots, this property offers a canvas brimming with potential. Whether you envision revitalizing it into a majestic single-family residence or retaining its current configuration with a townhouse on one side and two apartments on the other, the possibilities are boundless. While the property stands as a testament to enduring charm and character, it's essential to note that significant settling has occurred over the years. As such, unlocking its full potential will necessitate considerable renovation efforts. This property is a bona fide fixer-upper and is exclusively offered in its current "as is" condition, awaiting the transformative touch of its next custodian. With its prime location , this property represents not only an investment opportunity but a chance to become part of Chestertown's storied legacy. Seize the chance to breathe new life into this home and craft a future brimming with possibility. Embrace the challenge, unleash your creativity, and make your mark on Chestertown's captivating tapestry of history and culture. Schedule your viewing today and prepare to embark on an unforgettable journey of restoration and renewal!

349 & 351 High St, Chestertown

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

$415,000
2 Beds 1 Baths
A stately 1800’s waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own ground level storage. This is a unique setting offering waterfront living in downtown historic Chestertown and includes off street parking. Walk to downtown restaurants and shops. Beautiful southeast views of the Chester River with spectacular sunrises and plenty of year-round sunshine. Take in the all of the nearly year-round waterfront activities from your own back yard, including Chestertown Tea Party, 4th of July fireworks and Sultana down rigging weekend. Located on Maryland’s scenic eastern shore less than 85 miles from Washington DC to the south or Philadelphia to the north, this home is the perfect meeting spot for those living in the Mid-Atlantic region. This unit offers a 2 Bed 1 bath has a brand new kitchen, with island and upgraded bathroom along with up and down river views.

117 Water St N Unit #2A, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact: