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$3,000,000
87-acre tract located Northwest of Chestertown.  Land tract was annexed into the town of Chestertown and is served with municipal services.  The property is zoned residential (R-3 and R-4) and has been previously studied for residential development.  The land is approximately 44 acres of tillable and 48 acres of timber.  The farmland is surrounded by a forested buffer and may nicely serve the future layout and privacy of a residential community.  Site plans and previous preliminary designs are available to review to guide future planning on the property and can be provided.

Flatland Road, Chestertown

Listing courtesy of The Land Group. Contact: (410) 934-3478
$2,900,000
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:

$1,800,000
5 Beds ⋅ 5 Baths
Beautiful Dutch Colonial on 3 Acres with 500 +/- feet of waterfront overlooking Worton Creek. Near Worton Creek Marina and only a short drive to Historic Chestertown or Rock Hall. Enjoy the wildlife, rural setting, and inground pool. Native plants create a very nicely landscaped home. All wall paneling is Western Red Cedar and the wood floors are 150+ years old heart pine. The game room could be used as bedroom #5. The family room has a brick wood burning fireplace, table space , breakfast bar, and exposed wood beams. Sign posted.

22900 Handy Point Road Handy Point Rd, Chestertown

Listing courtesy of Davis Real Estate, Inc.. Contact: 410-778-2610
$1,725,000
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
$1,499,000
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
$1,095,000
3 Beds ⋅ 2 Baths
"Strawboard Mill" offers 2 brick, townhomes (each townhouse has 2 units), with metal roofs, 1 efficiency apartment and a 3 bedroom, 2 bath residence. The brick townhomes were built in 1902+/- and were used as housing for mill factory workers. There are two, 2 bedroom, 1 bath units in each townhome. Each townhome unit has washer and dryer. The efficiency unit also has a washer and dryer. All units are leased on a month to month basis. All townhome units have Lead Free Certificates from MDE. The main house, which houses the efficiency unit over the garage, was built in 2005. Current monthly rental income is $5,225 with the potential to increase to market level of about $6,500+/- and even more if you rent out the main house. The owners live in a well appointed Cape Cod that offers the possibility of a 1st floor bedroom, kitchen and family room as well as office space, 2 additional bedrooms on the second level with a "Jack n Jill" bathroom setup. There are laminate floors throughout most of the house as well as wood ceilings in most rooms. There are actually 2 garage spaces however one has been transformed into an exercise room. The rear deck overlooks the private backyard and offers a gazebo on the deck. Do you need a separate office? You are in luck! There is an attached office space with a mini split system for heating and cooling. The sellers live in the Cape Cod however you could easily rent the house to gain more income. There is potential to increase the current rent rolls to meet current rental market values. This is a rare opportunity to own, arguably, one of the finest rental properties in Chestertown!

131, 133 and 129 Flatland Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$1,095,000
"Strawboard Mill" offers 2 brick townhomes, with metal roofs, 1 efficiency apartment and a 3 bedroom, 2 bath residence. The brick townhomes were built in 1902+/- and were used as housing for mill factory workers. There are two, 2 bedroom, 1 bath units in each townhome. Each townhome unit has washer and dryer. The efficiency unit also has a washer and dryer. All units are leased on a month to month basis. All townhome units have Lead Free Certificates from MDE. The main house, which houses the efficiency unit over the garage, was built in 2005. Current monthly rental income is $5,225 with the potential to increase to market level of about $6,500+/- and even more if you rent out the main house. The owners live in a well appointed Cape Cod that offers the possibility of a 1st floor bedroom, kitchen and family room as well as office space, 2 additional bedrooms on the second level with a "Jack n Jill" bathroom setup. There are laminate floors throughout most of the house as well as wood ceilings in most rooms. There are actually 2 garage spaces however one has been transformed into an exercise room. The rear deck overlooks the private backyard and offers a gazebo on the deck. Do you need a separate office? You are in luck! There is an attached office space with a mini split system for heating and cooling. The sellers live in the Cape Cod however you could easily rent the house to gain more income. There is potential to increase the current rent rolls to meet current rental market values. This is a rare opportunity to own, arguably, one of the finest rental properties in Chestertown!

131, 133 and 129 Flatland Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$995,000
3 Beds ⋅ 4 Baths
Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away.

230 S Water St Unit #1, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$995,000
3 Beds ⋅ 4 Baths
Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. A short walk to downtown shops and restaurants.

226 S Water St, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$950,000
4 Beds ⋅ 4 Baths
This remarkable 4BR/3.5BA waterfront home boasts historic elegance and beautiful water views! The best of both worlds, this property is located on the Chester River, offering the relaxing water-oriented lifestyle while also being walkable to all the great restaurants and shops that downtown Chestertown has to offer! This historic gem, built in 1900, sits on a .22-acre lot, offering you space and privacy in the heart of Chestertown. Step inside and be awestruck by the expansive foyer leading to the great room with its soaring ceilings, creating an open and inviting atmosphere. Stained glass doors and windows, 2 fireplaces with Quimper and Delft tiled surrounds, and original hardwood flooring are some of notable details throughout this special home. With over 5,400 square feet of living space, there's room for everyone to enjoy and endless potential! An unexpected treat, the home has an indoor pool for year-round relaxation and entertainment. Additionally there is an attached 2-car garage, a very rare find in downtown. The large covered brick patio is ideal for outdoor entertaining overlooking the lawn and Chester River.

205 N Water St, Chestertown

Listing courtesy of Washington Fine Properties. Contact: info@wfp.com
$950,000
3 Beds ⋅ 4 Baths
Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away.

228 S Water St, Chestertown

Listing courtesy of Gunther-McClary Real Estate. 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
$899,000
Don’t miss out on the opportunity to own this restaurant and bar located in Historic Downtown Chestertown. 98 Cannon offers both indoor and outdoor dining with panoramic views of the Chester River. Ideally located next to the Chestertown Marina so patrons can dock and dine. Ample parking---13 owned spots, 26 shared spots, plus on-street parking. Chestertown’s only restaurant on the River. Unlimited potential for year-round income. Chestertown is located 90 minutes from Baltimore, DC, and Philadelphia and less than 1 hour from Annapolis. Enterprise Zone tax credits available. Buyers requesting additional information must sign NDA. Property is being sold as-is.

98 Cannon St, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 643-3033
$895,000
Commercial Development Site on busy MD Rte 213, Prime location across from Washington College Campus. Approx 1 acre, zoned C-3. Suitable for retail, restaurant, service uses. Water and sewer available.

515 Washington Ave, Chestertown

Listing courtesy of EShore. Contact:

$815,000
3 Beds ⋅ 4 Baths
Check out Chester River Landing's newest construction! This middle unit, three bedroom, three and a half bath townhouse is spacious and has incredible views of the Chester River. 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 #12, 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
$750,000
4 Beds ⋅ 4 Baths
This former horse barn was converted in 1990 into a well-crafted personal residence. In early 2018, the current stewards retained acclaimed contractors Taylor Loughry to apply their craftsmanship to a large portion of the house. The most delightfully unique characteristic of this 4-5 bedroom, 3 and 1/2 bath home with attached two car garage is its' private, landscaped lot accessed by a gravel driveway on North Water Street. A pair of new wood gates define the entry to the oasis. The redesigned flow of the first floor provides well for the intended purpose of both entertaining and home comfort. A den, powder room, and elevator adjoin the two-story, sun-filled foyer. A large living room with gas fireplace and separate dining room (with doors to the rear brick patio and raised beds) provide the pathway to a beautifully designed large island kitchen with breakfast area with bay window. Mudroom with sink, full sized washer and dryer and storage is adjacent to a side entry and double garage with EV charging station. Floor two comprises mostly a primary suite that includes bath, large office and exercise space with access to a very large, insulated and conditioned storage space (easily repurposed to a games room or home theatre), a guest bedroom and hall bath. The third-floor features two additional bedrooms and bath with large amounts of closet space. Recently installed solar panels, discreetly positioned, have resulted in nearly net zero energy expense.

106 Water St N Unit #1/2, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453
$739,900
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:

$739,900
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:

$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
$699,900
4 Beds ⋅ 2 Baths
Holiday special! For the month of December, sellers are offering a $20,000 credit toward the buy down of your mortgage rate or towards closing costs. Offer is valid until December 31st! Wait until you see this beautiful renovation! No detail has been overlooked in this open-concept historic Chestertown gem. The owners were able to achieve the perfect balance of updating the living space while maintaining the charm and character of the original house. Tall ceilings and thick moldings with high-end modern amenities give this property a one-of-a-kind feel. New kitchen with a large island, quartz countertops, gorgeous GE Cafe appliances. Both baths have been renovated and are some of the most beautiful we've seen. New HVAC, new roof and flashing. off-street parking with a garage/shed. The first floor features a living room, an open kitchen and dining area, a full bath, and a huge laundry/mud room. Doors lead out to the fenced-in yard and new patio. Behind the yard is an alley with off-street parking and the renovated garage/shed. The second floor has 3 bedrooms, an additional room that could be a bedroom if desired, and another stunning full bath. An additional bedroom or bonus room on the finished 3rd floor. Much of the original hardwood flooring remains. Fireplaces are non-functional but gas inserts could be added. Walking distance to all that historic Chestertown has to offer.

207 N Queen St, Chestertown

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

$497,000
Located on a highly traversed main road, this unassuming yet strategically located commercial office building offers a blend of functionality and convenience--reflected in the interior's generously sized offices and a conference room. The building's practicality extends to its exterior with room for ample parking and opportunities to install suitable landscaping. This property is all about getting the job done efficiently while maintaining a prominent presence on a main road for visibility and accessibility, making it an excellent choice for businesses of all types.

830 High St, Chestertown

Listing courtesy of SVN/Miller Commercial Real Estate. Contact: 410-543-2440
$460,000
4 Beds ⋅ 3 Baths
Great home located in desired Coventry Farms community of Chestertown. This home offers plenty of space for entertaining boasting 4 bedrooms, 21/2 baths, master suite, large open kitchen with breakfast/sunroom, large family room, deck, inground pool, large two car garage, large level lot and more. This home also offers a full unfinished basement which could give you an additional 1200 Sq. Ft. of living space. Home is located within Chestertown limits offering plenty of entertainment, shopping, parks, beaches and more. Home shows well and is ready for its new owner. Don't miss out on this great find. All reasonable offers will be considered.

248 Devon Dr, Chestertown

Listing courtesy of Douglas Realty LLC. Contact: (410) 255-3690
$449,900
Whether you envision building your dream home or are seeking a hunting retreat, this secluded lot offers options. Situated on 42.598 acres of select cut woodland, this property is a nature lover's dream, offering endless outdoor recreation possibilities and abundant wildlife. Existing house and barns are tear downs, do not enter. Make it yours today!

8220 Airy Hill Road, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453
$429,900
3 Beds ⋅ 3 Baths
Introducing this stunning new construction home just outside of Chestertown, MD in the Blakefield community ( QA Side) Boasting 3 bedrooms and 2.5 baths, this modern residence offers a perfect blend of style and functionality. The open-concept floor plan allows for seamless flow between the spacious living areas, while the gourmet kitchen features high-end appliances and sleek finishes. Retreat to the luxurious primary suite with its own private bath, creating a serene oasis. Enjoy the convenience of a two-car garage that is insulated and drywalled. Located within minutes of Chestertown's charming downtown area, shops, restaurants, and recreational options are just minutes away. Don't miss out on the opportunity to own this exquisite new construction home

215 Blakefield Dr, Chestertown

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

$429,900
5 Beds ⋅ 4 Baths
Bask in the beauty of this incredible 1920s home in downtown Chestertown! At 2890 square feet, this freshly painted 5 bedroom, 3.5 bathroom property has tons of space and an oversized lot featuring a secluded backyard with mature trees, fire pit, and off-street parking, most of which are very rare to find downtown! The many updates include a brand new HVAC system and hot water heater; updated electric, new slider doors, cooktop, combination wall ovens, dishwasher, and 2nd floor bath fixtures along with a meticulously restored stairway in the entry hall. Other features include original hardwood floors on the first floor & stairway & newel post, some original windows, refinished floors on first floor, original hardwood floors on the second floor, freshly painted and repaired dormers, privacy fence, revitalized front door, and much more! Aside from the fantastic interior space, you'll fall in love with the charming front porch and lovely balcony off the second story primary bedroom. The exterior is further improved with new topsoil, grass seed, fertilizer, straw, and flowers. 204 N Mill is located on a quiet street close to downtown shops, Washington College, waterfront, restaurants, farmer's market and shopping. Whether a residence or an AirBnb, this home has endless possibilities!

204 Mill St, Chestertown

Listing courtesy of RE/MAX Chesapeake. Contact:

$395,000
2 Beds ⋅ 3 Baths
Welcome to 101 S. Kent St! Prepare to be charmed by this beautifully updated and lovingly maintained historic home, located on a peaceful and quaint street. Built in 1880, this 2 bedroom, 2.5 bath property combines classic charm with modern comfort situated in the heart of downtown Chestertown. You're just a leisurely walk away from the waterfront, shops, restaurants, and Washington College! The current owners have had this property as a profitable Air BnB/short term rental (profit & loss statement available). Features include a private patio ideal for outdoor entertaining, original hardwood flooring, built-in bookcases, wood-burning stove, exposed interior brickwork, traditional brick sidewalks. Don't miss this perfect home in charming Chestertown!

101 S Kent St, Chestertown

Listing courtesy of Washington Fine Properties. Contact: info@wfp.com
$340,000
3 Beds ⋅ 3 Baths
Spacious, well-situated 3 or 4 bedroom, 2.5 bathroom rambler on almost 3/4 of an acre just outside downtown Chestertown. Sit on the front or back porches and enjoy the peace and quiet of country living. Backyard has plenty of room to play or just sit and enjoy the trees, birds or picturesque farmland views. Home features a spacious kitchen/dining room combo; front living room with built-in bookcases and wood-burning fireplace; primary bedroom with en-suite bath; pantry; and laundry room. Formal dinning room could also be a fourth bedroom. Back screened in porch just off the kitchen and dining room. Spacious garage has room for two cars and all your things. Well-built home from local contractor Crossley & Sons. Located on a quiet cul-de-sac street and backs to open farmland. Just on the edge of Chestertown but close to everything you need. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic architecture, local shopping, restaurants, art galleries, and waterfront walkways and parks. Chestertown is home to many festivals and an award winning Farmer's Market on Saturdays. Brand new YMCA with full gym, racquet sports, lap pool, sauna, etc. Enjoy country living on the Eastern Shore.

1006 Twin Ct, Chestertown

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

$334,900
3 Beds ⋅ 2 Baths
Endless possibilities for this centrally located property in Chestertown, across from Kent Plaza Shopping Center and close to Washington College and the newly built YMCA. In its past it has been a single family home, business offices, and most recently a 2 dwelling rental unit. Would also make a perfect home business with high visible road frontage and a quiet studio apartment in the rear, or a 2 bedroom home with an in-law/nanny suite at year. Either way it is easily turned back into a single family home. So many possibilities! Front Unit: 2 bedrooms, 1 full bath, large kitchen with attached laundry, separate dining room and large Living room. Entrance and parking in front. Back Unit: One bedroom efficiency with kitchenette and full bathroom. Entrance and parking in rear. Hardwood floors throughout both units except bathrooms and Kitchen. New bathroom and kitchenette in back unit. New gutters, paint and HVAC. Driveway has been extended to make 2 entrances and wrap around building for ease of getting in and out. Plenty of parking in front and rear. *Both units have active leases in place *Property could easily be turned back into a single family home by knocking through one wall as it was originally.

866 Washington Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$334,900
Endless opportunities for this centrally located property in Chestertown, across from Kent Plaza Shopping Center and close to Washington College, Dixon Valve, and the new YMCA. In its past it has been a single family home, business offices, and now a 2 dwelling rental unit. Would also make a perfect home business with high visible road frontage and a quiet studio apartment in the rear. Front Unit: 2 bedrooms, 1 full bath, large kitchen with attached laundry, separate dining room and large Living room. Entrance and parking in front. Back Unit: One bedroom efficiency with kitchenette and full bathroom. Entrance and parking in rear. Hardwood floors throughout both units except bathrooms and Kitchen. New bathroom and kitchenette in back unit. New gutters, paint and HVAC. Driveway has been extended to make 2 entrances and wrap around building for ease of getting in and out. Plenty of parking in front and rear. *Both units have active leases in place *Property could easily be turned back into a single family home

866 Washington Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact: