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$3,250,000
Historic Radcliffe Mill, located on the Eastern Shore of Maryland, dates back to 1891 and is on the National Register of Historic Places. Restoration of the flex complex was completed in 2007 and is comprised of the 4-story mill building and the annex/seed house. Set in Chestertown on 2.3-acres next to Radcliffe Creek, the site has been important to Kent County agriculture since 1694. (Main photo courtesy of Tyler Campbell Photography). The main building features a reception area with an elevator leading to business offices, while the sushi-thai restaurant, is just off the main lobby. Radcliffe Studios is located in the Seed House offering a yoga studio, cafe, and several small wellness businesses. Property amenities include a 61-car park, a loading dock and an original grain elevator. South Fork Studio Landscape was part of the design team working on the project. The convenient location is within walking distance of Washington College and the Wayne Gilchrest Walking Trail and is just one-mile from downtown Chestertown. Founded in 1706, Chestertown is set on the banks of the Chester River. Stroll the brick sidewalks lined with lovely period homes, shops, theatre, galleries and dining options including an Oyster Bar, cafes and restaurants. Residents and visitors alike enjoy the farmers market, Fountain Park, Chester River Walk, annual Tea Party Festival and public cruises on the Chester River Packet. Chestertown is located about 90 minutes from Washington, D.C. and Philadelphia, and 1-hour from Wilmington.

860 High St, Chestertown

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

$799,999
3 Beds 3 Baths
This listing offers the unique opportunity to own two waterfront parcels, one improved by a beautiful 3-4 bedroom cape, and an adjacent perc approved lot all located less than a mile from Chestertown. The addresses are 121 Lyons Ln. which is 1.9 acres, 118 Lyons Ln. which is 1.2 acres and 117 Lyons Ln. which is .44 for a total of 3.5 acres. They are being sold together and the tax information is for all three lots. The cape is on the 1.9 acre wooded lot and features premium materials and finishes. There are yellow pine floors reclaimed from Camden Yards, crown moulding, wainscoting, panel doors, fireplace, sun room and a master bedroom on the first floor. The second floor has two bedroom and a third room which could be a bedroom, office or 2nd floor family room. The second floor bathroom is huge and has just been remodeled. There is also a separate studio or home office, also recently remodeled, in the rear yard with AC/Heat. A Williamsburg inspired garden surrounds the studio and the rear yard is partially fenced. The waterfront is a quiet creek right across the Chester River from the historic district. The owners have a permit for a new dock and it will convey. By the water is a large screened in Gazebo perfect for crab feasts or for enjoying the abundant wildlife. The second waterfront lot is 1.2 acres, not buildable, but it does allow for more water access. The third lot is .44 acres, perc approved, level, cleared but with some mature trees . A second home could be built for a family compound or a carriage house, guest house or barn. Or, simply hold on to it as an investment. Lots of options so come take a look!

121 Lyons Ln, Chestertown

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

$750,000
3 Beds 3 Baths
This custom home is one of a kind and perfect for the golf enthusiast! Here you can walk out your back door to holes 14, 15, and 17 of the Chester River Yacht and County Club golf course. This home was built by Darling Construction eight years ago and is in immaculate condition. In this home you'll enjoy cooking and entertaining in the large, upgraded kitchen with a wet bar, granite countertops, soft close cabinets, pot filler over the stove, and stainless-steel appliances. Enjoy your days in the sunroom... full of windows and light and your evenings in the living room by the gas floor to ceiling stone fireplace. This home has a formal dining room with French glass doors, separate office, two guest bedrooms with a Jack and Jill bath and large primary suite. The primary bedroom has two walk-in closets, laundry area, and connected to the primary bath with heated floors, dual sinks, and a walk-in shower with dual showerheads. Park your car in the oversized, side entry three car garage that leads into the house with a guest bath and pantry. A spectacular feature of this home is that it is completely handicap accessible. Wide halls, large doorways, zero steps, roll in shower and handrails. This property has all the upgraded features including, a geothermal system, crown molding and chair railing, recessed lighting, tray ceilings, 9'+ ceilings, tankless hot water heater, full concrete crawlspace, lawn sprinkler system, and so much more! Be sure to schedule your showing right away because this home is hard to find!

25731 Collins Ave, Chestertown

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

$749,000
This property backs to Kent Countries largest industrial park which has several buildings constructed and occupied and many under construction. This Industrial is changing the business climate of Chestertown tremendous growth is in process. Pizza Hut restaurant has recently closed and contains an already in place layout for a new restaurant to re-brand this location. The building has the additional potential to be renovated into a mixed use facility with a single or multiple MEDICAL tenants. The location is nearby to town, which is home to Washington College, and is located only 90 minutes from Baltimore, Philadelphia and Washington,D.C. This property backs to Kent Countries largest industrial park which has several buildings constructed and occupied and many under construction.

903 Washington Ave, Chestertown

Listing courtesy of EXIT On The Bay. Contact: (410) 304-2011

$668,000
5 Beds 5 Baths
Eastern Shore home, c.1890 is located in the heart of Chestertown’s historic district and is just a short stroll from the Chester River Walk, Fountain Park, shops, dining and walking trails. Every modern-day amenity has been incorporated into this lovingly renovated home while preserving the original charm. Skylights and windows let in an abundance of natural light to showcase the lovely heart pine floors and detailed millwork. The home spans three levels and greets owners through a gracious foyer opening to the library with its reading nook bookcase and fireplace. The first floor open design also features a well-appointed kitchen, breakfast room, dining room, living room and two powder rooms. The second floor is designed with two ensuite bedrooms and the top floor offers three bedrooms and a powder room. Adding to the welcoming ambiance of the property is the recently built carriage house used as a workshop/studio and an english gatehouse serving as a potter’s shed. The enchanting garden features a goldfish pond, stone walls, planting beds, and a pergola with climbing rose vines. Founded in 1706, Chestertown is set on the banks of the Chester River and is home to Washington College. Brick sidewalks are lined with lovely period homes, shops, a bakery, galleries, theatre, oyster bar and restaurants. Residents and visitors alike enjoy the river walk, parks, farmers market, walking trails, community activities and annual festivals. River cruises are available on the Chester River Packet and Schooner Sultana. Chestertown is located about 90 minutes from Washington, D.C. and Philadelphia and 1-hour from Wilmington.

111 S Mill St, Chestertown

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

$495,000
1 Baths
A unique opportunity! This charming brick building was originally built in the 1800s as a chapel named Mowbray Chapel, eventually abandoned and then the interior was completely rebuilt in 2021 with electric, utilities, a new well and septic. A SIMPLY STUNNING light filled space that has been used as a residence and entertaining venue. Completed with the highest quality of materials and a brand new kitchen, full bath room and laundry room as well as a gas wood stove yet blended with the large windows, gorgeous brick walls, high ceilings and substantial woodwork. A true blend of old world elegance and modern amenities. Nestled among the mature trees on a 3+ acre property, there is also good outdoor space with a lawn, woods and a pond combined to offer spectacular outdoor areas year round.

5179 Quaker Neck Rd, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$410,500
4 Beds 2 Baths
This pristine 4BR, 2BA brick rancher in Kingstown Manor is ready for it's new owners. 1,792 sq ft finished living space - glowing hardwood floors throughout - updated bathrooms with travertine tile backsplash & flooring - new HVAC 2021 - dry bar - meticulusly maintained - The large living room is warm and inviting open to the formal dining room. A spacious breakfast area looks out to the backyard and flows into the kitchen where you’ll find lots of counter space, moveable island, granite countertops, stainless steel appliances and nice pantry. 2 car attached Garage with inside access - asphalt driveway - 2 large utility/storage sheds with electric - NO HOA - Walking or biking distance to downtown Chestertown; Farmers Market every Saturday morning, Arts & Entertainment district, Washington College, restaurants, local shops, and much more.

240 Duke Of Kent St, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453

$369,900
3 Beds 2 Baths
**REDUCED $30k!!** This spacious 3 bedroom, 2 bath rancher has all of the makings of a terrific home! Well-situated at the end of a cul-de-sac, the back yard has room to spread out and play or enjoy the open view of it from the screened porch. Built by well-regarded local builder, Buzzy Lane, the vaulted ceilings give the home an airy, spacious feeling. The large Main Bedroom is placed on the opposite side of the home from the other two generously-sized bedrooms for extra privacy in a layout that will accommodate a variety of living needs. The Great Room has a cozy gas fireplace and connects to both the Kitchen and Dining Room. An oversized garage offers ample storage for all of your stuff. The location is on the edge of Chestertown but close to everything this historic college town has to offer. The area is a boater's dream as well. You will love living here!

1005 Twin Ct, Chestertown

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

$349,990
5 Beds 4 Baths
This move-in ready Verona, a 2,302 square foot, three-story home, offers five bedrooms, and three and a half bathrooms. This well-designed home has an inviting foyer that opens to the spacious family room. The family room is open to the dining space and the family-friendly kitchen with stainless steel appliances, beautiful white cabinets, a large corner pantry and a peninsula with additional room for seating. A powder room is conveniently located on the first floor tucked away in a private nook. This roomy floor plan allows you to live comfortably with the ideal amount of space and room for flexibility. The upstairs owner's bedroom with an en suite bathroom and a walk-in closet sits in the back of the home for privacy. There are three additional bedrooms and a secondary bathroom on the second floor. The third floor offers the fifth bedroom and a third full bathroom, as well as a finished flex room. The Verona includes a washer and dryer, a white window treatment package, and the exclusive Smart Home® Package giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

104 Silver Heel Dr, Chestertown

Listing courtesy of DRH Realty Capital, LLC.. Contact: (667) 500-2488

$339,990
4 Beds 3 Baths
The Sidney is a 1,849 square-foot move-in ready two-story home that features four bedrooms, and two and a half bathrooms. A welcoming foyer with a coat closet greets you as you enter your home from the cozy front porch. This open floorplan allows you and your loved ones to spend quality time together in the spacious family room, casual dining area, and kitchen. The well-appointed kitchen showcases an abundance of sarsaparilla cabinetry, a sizeable peninsula island, stainless steel appliances and a large corner pantry. The laundry room is conveniently located off the kitchen on the first floor. Exit through the sliding glass doors in the dining room to enjoy your quiet patio at the back of the home. Also located on the first floor are the powder room, storage closet and an additional coat closet. Upstairs you will find the owner's suite complete with its private, double bowl vanity bathroom and walk-in closet. The additional three bedrooms allow for everyone in your family to have their own space. The Sidney includes a white window treatment package and the exclusive Smart Home® Package giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

208 Silver Heel Dr, Chestertown

Listing courtesy of DRH Realty Capital, LLC.. Contact: (667) 500-2488

$339,900
3 Beds 2 Baths
Price adjustment!! Great Value for this like new Rancher in Chestertown, Queen Annes County! Built in 2018 this lovely home has 3 bedrooms and 2 full baths. The owner's suite is secluded on the left side of the home to provide privacy and the other 2 bedrooms are on the right side with a hall bath. Owners' suite includes a generous walk in closet and large bath with double vanity and tiled walk-in shower. Carpets keep the bedrooms cozy while the Open Plan Living Area showcases beautiful Hardwood floors and a Vaulted Ceiling that makes this home have a wonderful spacious feeling! The Kitchen has beautiful white soft close cabinets with granite counters, an Island with seating, matching white appliances and opens to the Dining and Living rooms. Great for entertaining! Slider doors open to the back yard and shows views of trees and pasture. New Landscaping and trees with a beautiful lawn and a garden shed out back to hold your tools. Two car garage has been updated with insulation, drywall, storage shelves and an epoxy floor. There is a water softener (owned) and an encapsulated crawl space. Just down the street is the Deep Landing Boat Ramp. This 0.65-acre facility on the Chester River has a 14-foot-wide boat launching ramp. This landing is one of the premier boat ramps on the Queen Anne’s County side of the upper Chester River. The cement ramp is adequate for vessels up to 25 feet. No HOA means you can store your boat at home. Beautifully maintained and still like new, this home is move in ready!

724 Deep Landing Rd, Chestertown

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

$339,000
3 Beds 2 Baths
Welcome to 119 Wood Duck Lane in Chestertown, MD. Enjoy peace and quiet in your less than a year old home! This home is MOVE IN ready! Before you enter the home, notice the beautiful view out the front door- wide open and relaxing! As you enter the home you will find an open concept layout with vaulted ceilings. The living room is bright and open to the kitchen. The kitchen is large, offering plenty of counter and upgraded cabinet space. You can choose to sit at the eat-in kitchen bar, or dine at the table where you have views of the large backyard. Same level living provides 3 LARGE bedrooms, huge closets, and 2 full bathrooms. Each bedroom is a great size and the closets are all over sized! This home offers a separate laundry room- no walking through the laundry to reach the garage! Oversized garage fits 2 large vehicles with ease. Owners add a new water softener system, and a brand new 100ft well. Moving outback you have a HUGE private yard with tree lines or fence giving you that extra privacy! The yard is great! Perfect for playing, entertaining , or just relaxing and enjoying your new home!! You have options of parking in the driveway out front or driveway out back. This is a MUST SEE!!!

119 Wood Duck Ln, Chestertown

Listing courtesy of RE/MAX Executive. Contact: (443) 274-1900

$329,990
5 Beds 4 Baths
This move-in ready Verona boasting 2,302 square feet is a three-story home that offers five bedrooms, and three and a half bathrooms. This well-designed home has an inviting foyer that opens to the spacious family room. The family room is open to the dining space and the family-friendly kitchen with stainless steel appliances, a large corner pantry and a peninsula with additional room for seating. A powder room is conveniently located on the first floor tucked away in a private nook. This roomy floor plan allows the entire family to live comfortably with the ideal amount of space and room for flexibility. The upstairs owner's bedroom with an en suite bathroom and a walk-in closet sit in the back of the home for privacy. There are three additional bedrooms and a secondary bathroom on the second floor. The third floor offers the fifth bedroom and a third full bathroom, as well as an option flex or storage room. The Verona includes the exclusive D.R. Horton Smart Home® Package through ADT giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

112 Silver Heel Dr, Chestertown

Listing courtesy of DRH Realty Capital, LLC.. Contact: (667) 500-2488

$329,990
5 Beds 4 Baths
Available move-in ready home in The Village at Chestertown! The Verona, a 2,302 square foot, three-story home, offers five bedrooms, and three and a half bathrooms. This well-designed home has an inviting foyer that opens to the spacious family room. The family room is open to the dining space and the family-friendly kitchen with stylish gray cabinets, stainless steel appliances, a large corner pantry and a peninsula with additional room for seating. A powder room is conveniently located on the first floor tucked away in a private nook. This roomy floor plan allows the entire family to live comfortably with the ideal amount of space and room for flexibility. The upstairs owner's bedroom with an en suite bathroom and a walk-in closet sits in the back of the home for privacy. There are three additional bedrooms and a secondary bathroom on the second floor. The third floor offers a fifth bedroom and a third full bathroom, as well as a flex room that could be used for storage. The Verona includes a washer and dryer, a white window treatment package, and the exclusive Smart Home® Package giving you complete peace of mind living in your new home. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built.

110 Silver Heel Dr, Chestertown

Listing courtesy of DRH Realty Capital, LLC.. Contact: (667) 500-2488

$319,000
4 Beds 2 Baths
Welcome to 626 High St, she is just adorable. The hardwood floors throughout this 3 level home have withstood the test of time and are gorgeous! You immediately feel at home! Lovely fixtures, which are probably original to this home add to the charm. The dining room is very generous in size. The main level has an office, powder room, a nice kitchen with an eat in breakfast bar. There are four bedrooms, and 1.5 baths all total. This home has been a rental for a few years, but the owners have maintained it very well. There are just a couple of tweaks to be made, and the owners are working on that as well. The owner has explored the possibility of a possible building lot on the Lynchburg side. There may be a possibility of that with local zoning approval. Nothing is set in stone, but the new owner could explore further, if desired. In the historic district, four blocks to downtown, but close to Chestertown's Rail for Trails, which is a nice, paved path through Chestertown. Enjoy Washington College and all it has to offer to the community, local restaurants, a thriving artists community, music, the farmer's market, artisans, charming shops, and friendly welcoming people! There is a health food store, coffee shops, two grocery stores, hardware store, a local golf course at Chester River Yacht and County Club, bocci and pickle ball teams you can join! Like to kayak and canoe? You can easily do both on the Chester River, or Radcliffe Creek.

626 High St, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact: