Chestertown MD Homes For Sale

Chestertown MD Homes For Sale

View all the homes for sale in ChestertownMD at a median listing home price for all budget. See pricing and listing details of Chestertown real estate for sale.

Chestertown MD Homes For Sale

$342,000
3 Beds 2 Baths
Price Improvement - Welcome to this delightful brick rancher, offering over 1,500 square feet of comfortable, inviting living space. This home boasts 3 spacious bedrooms and 2 full baths, perfectly designed to accommodate a variety of lifestyles. Step inside and be greeted by the open floor plan, where the brick fireplace in the living room adds both charm and warmth—an ideal gathering spot for cozy nights. The country kitchen features a large island, separate pantry, and plenty of storage, making meal prep a breeze. At the rear of the house, you’ll find the primary suite—a private retreat with an ensuite that includes a newly updated shower. Original hardwood floors, elegant and timeless, flow throughout the home, adding warmth and character to every room. Newer windows and an encapsulated crawl space boost energy efficiency while filling the home with natural light. This home also includes a mudroom/laundry area and an attached one-car drive-thru garage for added convenience—perfect for busy families or car enthusiasts. Additionally, the property features a separate workshop shed (18x22) with a garage door, ideal for hobbyists and extra storage. Out back, relax on the patio surrounded by mature plantings, providing a peaceful escape with scenic views of the farmland behind the home. For added convenience, the property offers a 2-car drive pad for ample guest parking, and the rear enclosed porch with heat is perfect for year-round enjoyment—a versatile space for relaxation or entertaining.

24291 Chestertown Rd, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453

$660,000
4 Beds 3 Baths
UNIQUE 4 BEDROOM/3 BATH CUSTOM BUILT CONTEMPORARY on a corner .37acre lot in the highly desirable neighborhood of Mile Tree Village. This gorgeous, meticulously maintained home offers all on one floor living in light-filled, easy care, open floor plan comfort. Features include cathedral and vaulted ceilings in the main living area and master bedroom; handsome light-toned maple flooring throughout the central living area; a glass doored corner gas fireplace in the living room; ample cabinet, pantry, storage and closet space; an oversized attached two car garage; roofed, sitably sized front and side porches; a lovely large rear patio with awning; and a custom-built stone terrace with a waterfall fountain. Additional household amenities are extensive, including like-new stainless kitchen appliances; induction cooktop and double wall ovens; a kitchen prep sink; custom granite and Corian counters in the kitchen and bathrooms, a soaking tub and glass walled walk-in shower in the Primary Bathroom ; hardwired home security and fire alarm and sprinkler systems ; a whole house generator, a surround sound system; a central vacuum system; multiple phone lines; automatic garage door; invisible fencing for pets, and the list goes on. The house has two sets of solar panels installed on the rear roof: one owned by the Sellers and the other subject to a power purchase agreement with TESLA. Both sets of panels convey with the house. Sellers are billed monthly for power generated by the TESLA owned system and receive approximately $6o/year from SOLSYSTEMS for power generated by the panels they own. Professionally maintained landscaping that includes a variety of lovely mature flowering shrubs, perennials and trees and an in-ground watering system surround the house. A trim lockable garden shed sited in a wooded area at the back of the house provides out of the way storage for lawn mowers and garden equipment and supplies. In addition to its many on-site pluses, this wonderful home offers convenient, quick and easy access to Washington college, area schools, parks, doctors, churches, Historic downtown Chestertown, waterfront recreational facilities and shopping centers. SIGNIFICANT PRICE REDUCTION! MOTIVATED OWNERS!

110 Birch Run Rd, Chestertown

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

$579,000
2 Beds 3 Baths
Discover the epitome of luxury living in this exquisite townhome nestled within the prestigious water-oriented community of Chester River Landing. Designed with elegance and comfort in mind, this residence offers an unparalleled lifestyle that combines sophistication with the serene beauty of waterfront community living. The heart of the home, the open kitchen is designed for both functionality and style. It features sleek countertops, ample cabinet space, and a large island that doubles as a breakfast bar, making it perfect for meal preparation and casual dining. Enjoy the convenience and efficiency of top-of-the-line appliances throughout the home, including a stainless steel refrigerator, oven and dishwasher. Open room on first floor could be used for a third bedroom for guests. Enjoy the sunset from the upper deck or below on the screened in porch by the pond with fountain. The porch was renovated this spring with high tech flex screens and ceiling was waterproofed providing for increased time for usage while keeping the area dry. Chester River Landing is nestled along the serene Chester River, this charming waterfront community exudes a perfect blend of relaxation and recreational opportunities. The centerpiece of the community is a picturesque floating pier that gently sways with the rhythm of the water. This well-maintained pier offers numerous available slips, making it an ideal haven for boating enthusiasts who enjoy easy access to their watercraft. Enjoy the community pool during the day then take in the sunset on the pier with picnic tables and a gas grille. As the day transitions into evening, the fire pit area becomes a popular gathering spot. Encircled by cozy adirondack chairs, the fire pit offers a warm and inviting ambiance, perfect for sharing stories, roasting marshmallows, and enjoying the company of neighbors under the starlit sky. All of this while located in the Historic Town of Chestertown, known for its waterfront charm, restaurants, and weekend festivals! Don't miss your chance to make this remarkable property your own!

103 Landing Ln, Chestertown

Listing courtesy of Coldwell Banker Realty. Contact: wpeach@cbmove.com

$394,900
3 Beds 2 Baths
Where Shore living begins! Welcome to 201 Princess Anne, located on the Queen Anne's County side of the Chester River Bridge. This well maintained home is established on just over 3/4 of an acre within the quiet subdivision of Kingstowne Manor. Offering 3 bedrooms, 2 baths, attached garage and comes equipped with a fully floored attic for all of your storage needs! A new roof system was installed April of 2024. This system has a transferable 10 year warranty! The asphalt driveway will ensure a smooth transition home and offer plenty of area for parking. This attached garage provides ample space to keep your vehicles, toys or projects out of the weather and well protected. Equipped with a propane heater and 220 AMP service, you can comfortably stay busy year round. The spacious kitchen provides under cabinet lightening, beautifully crafted seamless quartz countertops and conveys all kitchen appliances. The Living Room and Primary Bedroom are both generous with the space they provide. New carpeting in Primary was installed April of 2024. All 3 bedrooms have desirably spacious closets with ceiling fans throughout. Stepping outside, you'll find plenty of backyard seating and shade underneath the recently installed gazebo. The patio here will also provide ample space for grilling and gathering. The fenced in back yard offers a worry free option of allowing your children (four legged or two) to play freely. Home is equipped with top of the line Fiber Optic Internet services. The Septic System has also been updated with an additional 80' drain field to support any of your in home services.

201 Princess Anne Dr, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$399,900
3 Beds 3 Baths
Come By this brand new Cape Cod nestled in charming Pear Tree Point! This 3-bedroom, 3-bathroom haven offers the tranquility of coastal living with the ease of new construction. Step inside and discover the warmth of this open floor plan luxury vinyl plank flooring flowing throughout the main level. Unwind in the light-filled living area, perfect for entertaining, or retreat to the inviting main-floor primary bedroom suite, designed for ultimate relaxation. This private sanctuary boasts an attached bathroom with modern fixtures and finishes, and spacious walk-in closets. Unleash your inner chef in the stunning kitchen, featuring stylish shaker cabinets, gleaming granite countertops, and a suite of stainless-steel appliances. Extend your living space onto the expansive patio, perfect for al fresco dining or simply soaking up the tranquility of your waterfront surroundings. Modern finishes throughout and ample storage space completes this lovely home. But the best part? Pear Tree Point offers a vibrant community atmosphere with water access, marinas, and nearby parks. Don't miss this opportunity to own a brand-new waterfront haven! Contact us today to schedule your private showing .****Special Discounted Financing in available for this home, with rates in the low 5's are available**** Contact for details, rates subject to change, subject to loan qualification.

473 Pear Tree Point Rd, Chestertown

Listing courtesy of RE/MAX Executive. Contact: (443) 292-9250

$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:

$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:

$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. Located squarely in the Arts & Entertainment District and Enterprise Zone, both residential and commercial uses are permitted. 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:

$649,000
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

$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:

$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. Located squarely in the Arts & Entertainment District and Enterprise Zone, both residential and commercial uses are permitted. 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:

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