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

4 Beds 4 Baths
Beautiful home with stately presence on a large corner parcel within Chestertown's Historic District. Mill Street offers privacy and quiet living in the heart of town. Lovely landscaped courtyard and a sunny patio/deck. Gracious flowing floor plan with beautiful, large, squared rooms that retain many of their original design elements. The original part of the house dates to the 1840's . You will love the wood floors throughout, large gourmet kitchen with soapstone countertops and ample storage, including a spacious walk-in pantry. Formal dining and sitting room with a fireplace, as well as flex room for entertaining. Upstairs there is a large primary bedroom with a walk-in closet, a smaller bedroom with a connected bathroom, as well as a third bedroom and additional full bath. This second level also boasts an office and library or tv room. The third floor has a large fourth bedroom and plenty of attic space for storage. The property offers the rare in-town feature of an enchanting courtyard/garden which leads to an oversized garage/workshop. Plenty of off-street parking with an additional driveway facing Cannon street. 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. Stroll down to the Chester River waterfront, the farmers market on Saturday morning, or Zelda’s Speakeasy and multiple restaurants in the evening. Just a block from the Chestertown's Rail Trail, which connects multiple parks and is great for walking or biking.  A short walk to wonderful shops, restaurants, bakeries and less than a block to a natural foods grocery store, this corner home on Mill Street offers privacy and spacious living, yet is only steps away from all Chestertown has to offer. Chestertown is located about 90 minutes from Washington, D.C. Philadelphia and South Jersey, and 1-hour from Wilmington.

112 S Mill St, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

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:

6 Beds 4 Baths
Welcome to the former historic HILLTOP HOTEL! A charming estate which underwent significant renovations in 2021 while preserving many of the original characteristics the home has to offer. This property is unlike any other - offering historic charm, tranquil atmosphere, ample privacy, outdoor living & entertaining as well as turnkey amenities. The property sits perched high above the hillside of the Eastern Shore providing for stunning sunsets as you relax on the wraparound porch feeling the gentle breeze from the Chesapeake Bay. As you enter and proceed up the gravel driveway you are greeted by a large circular drive, beautifully manicured lawn, 4.74 acres of mature landscaping and the grandeur of the 3 story historic home. The first and second floors have been updated to include bright new paint throughout, remodeled kitchen offering an abundance of natural light, all new appliances, french doors were installed off the kitchen and study leading out to a new beautiful brick terrace overlooking scenic countryside views, updated powered room on the first floor, primary second floor bath has been completely remodeled to include updated amenities. The second floor offers 3 bedrooms, 2 full baths along with a spacious laundry room. As you make your way up to the third floor you immediately noticed the extensive renovations. Every aspect of the third floor was meticulously remodeled and redesigned including new insulation, new plumbing, new electric, new drywall, new commercial grade HVAC system and all 14 windows throughout the third floor were replaced. The third floor offers 3 bedrooms, 1 full bath and large beautiful living area. All hardwood floors throughout the home were refinished to their original beauty. New commercial grade water treatment system was installed. The wraparound porch was completely painted and all porch columns were wrapped. The exterior back of the home was sealed and painted. New roof installed. Both chimneys were repointed. Dual zone HVAC. This is a COMMERCIALLY ZONED property - Zoned Crossroads Commercial. Perfect for B&B or commercial use. Centrally located between historic Chestertown, MD and Rock Hall, MD. Owners are open to selling property furnished with the exception of several items.

7979 Sandy Bottom Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

4 Beds 5 Baths
SMITH-RINGGOLD HOUSE. This exceptional property is a rare find: an authentic waterfront 18th century home with 21st century comfort. Originally a merchant’s home in the heart of historic Chestertown, the Smith-Ringgold house has been modified representing four defined periods and enlarged over the course of its 250-year history. The present owner took two years to restore the home’s structural integrity from the foundation to the attic, adding a river-side addition and porch, replacing the cedar shingle roof, and completely redoing the plumbing, wiring, heat and A/C systems. The wood floors throughout the house have been beautifully restored. Modern storm windows are energy efficient and all but eliminate street noise. Aside from your own personal touches, this house is move-in-ready. The ground floor has a large double parlor, cozy 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 bedroom, with part of the home’s original c. 1759 roof forming a unique design element. The backyard was extensively terraced, probably in the late 1700s, in descending levels down to the Chester River. 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. 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

4 Beds 2 Baths
Your dream house awaits in the most perfect location! This delightful custom built home, being offered on one of the most sought after streets in Downtown Chestertown, and perfectly situated at the 'quiet end' of Queen Street, is only one block to the Marina, restaurants/shops, and overlooks Wilmer Park, with the Chester River beyond. Although this home has the true look of a an Period Colonial Home, it was actually newly constructed in 2006, on the original footprint of an older historic home. The owners have not only built , but meticulously cared for, and loved it throughout the years, being located so conveniently to all the things everyone loves about Historic Chestertown. As you walk up to the house you will find the porches very inviting and you will get so much enjoyment being out there at any time of day. As you come in you will find a front living room with a wood burning fireplace that adds warmth and enjoyment to the whole home. through to a cozy dining room or extended living room . Next, a pristine kitchen, refreshing and full of light, which offers plenty of storage and counter space. There's a main level laundry offered and then what could be a Primary Bedroom at the back of the house (with a full bath), or it can be used as a family room, as it is currently now. Through out the house which is not standard, but was thoughtfully and custom added, are very ample, oversized closet spaces for plenty of storage. You will also find an upstairs staircase to the floored attic that allows plenty of room for all your additional storage needs. On the second floor you have the option for a very spacious primary bedroom at the back of the house and an additional 2 rooms which have been a guest room and office . Through out the house you will find gorgeous plantation shutters to help allow the sun in when you want or help keep it out. Very tastefully done. As you settle into the heart of downtown you will be able to enjoy the Traditional Farmers Market on Saturdays , The well known Tea Party Festival , The Dickens Holiday Celebration and Down Rigging Weekend, just to name a few. The Garfield Center is always a favorite with a line up of theatrical shows and musical attractions. You will quickly fall into your favorite enjoyments and pass times that Chestertown has to offer . Some of the favorites of downtown will be the coffee spots, eateries and dining options which can all be with in within a few minute walk. Many details about this house can still be shared but come see and feel the welcome and the ease of a well built costume home that has been well taken care off and ease of low maintenance.

223 S Queen St, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

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