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

This building has been converted into 4 apartments. All units are currently rented. Limited interior photos to respect tenant privacy. Landlord pays all utilities. 128 North Queen Street, built in the beautiful Queen Anne style is one of the finest 19th-century houses in the Chestertown Historic District. The house is a block from the Chester River, close to Washington College and two blocks from downtown, shops, and the Chestertown Marina. It was designed by Baltimore Architect ,Benjamin Owens. The building served as the Methodist Parsonage for the Christ Methodist Church on High Street soon after he designed the church in 1887. The multi-gabled house is asymmetrical, filled with light from large double-hung windows, with a three-story turret in one corner large enough for a desk from where you can view the Chester River. Hardwood floors are located throughout. A beautiful original polished staircase with turned and polished wood balustrades rises from the central hall. Original stained glass windows shimmer with color in the main staircase and a second-floor bathroom which retains an amazingly large claw foot bathtub with polished wood surround. A slate surround and carved wood fireplace mantel center the den and living area on the first floor. The building is heated by a one year old boiler and cooled by a one year old heat pump system. Unit 1 is an efficiency. Rent $980 Unit 2 is 2 stories and 2 bedrooms with a washer/dryer. Rent $1850 Unit 3 is a 1 bedroom with a turret. Rent $1300 Unit 4 is a 1 bedroom with a turret. Rent $1200 Last year's electric: $4331 Last year's oil: $3215

128 N Queen St, Chestertown

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

4 Beds 3 Baths
Welcome to your peaceful retreat in the quiet community of Kingstown on the Queen Anne's side of Chestertown! This stick-built rancher by Alton Darling offers a serene setting with its backing to woods and open space, ensuring tranquility and privacy. Step inside to discover one level living that features four bedrooms with two bedrooms with attached private bath for ultimate convenience and comfort. The screened-in back porch invites you to relax and enjoy the natural beauty that surrounds you. This home received an upgrade in '17, ensuring efficiency and cost savings. The roof, replaced within the last ten years, provides peace of mind for years to come. Recent upgrades include new carpet in the living areas and bedrooms, as well as new flooring in the bathrooms, adding a fresh and modern touch. All major repairs have been completed, leaving the opportunity for the new owner to personalize and add their final touches to make it their own. Queen Anne's County offers extensive park and recreational programs, perfect for outdoor enthusiasts. Meanwhile, Chestertown boasts a vibrant cultural scene with fine dining options, theaters, a farmer's market, Washington College, and access to the scenic Chester River. Be sure to mark your calendars! Photos will be uploaded next week, and the house is expected to go live on 4/12. Don't miss the chance to experience this delightful property firsthand at the Open House on 4/13 from 11-2. Schedule your visit today and envision the peaceful lifestyle that awaits you in this charming home.

109 Coleman Dr, Chestertown

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

5 Beds 4 Baths
Welcome to your future haven in the picturesque community of Crestview! Nestled in the heart of Chestertown, this magnificent home at 207 Pondview Ct offers a harmonious blend of natural beauty and modern luxury, creating an unparalleled living experience. Upon arrival, you'll be captivated by the tranquility of the serene community pond that gracefully borders this residence. Imagine starting your day with the calming sight of water views right from your backyard, a serene oasis that beckons relaxation and peaceful moments. This spacious home features 4+ bedrooms and 3.5 baths, offering ample room for comfortable living and entertaining. The main level boasts a luxurious primary bedroom complete with a spa-like bath featuring a soaking tub, separate shower, and three spacious closets. A cozy sitting room off the primary bedroom leads to the inviting living room, adorned with a wall of windows that showcase mesmerizing pond views. Glass French doors seamlessly connect the living room to the formal dining room, creating a perfect flow for hosting gatherings and creating cherished memories with family and friends. The well-equipped kitchen is a chef's delight, boasting abundant cabinet space, a convenient breakfast bar, and a charming dining area perfect for casual meals. Step outside through the sliding door to the deck, where you can bask in the beauty of the pond and enjoy alfresco dining in a serene setting. Ascending the stairs to the second floor, you'll find a loft area that overlooks the living room and offers more breathtaking pond views. To the left of the loft is one of the three guest bedrooms, complete with a private bath. On the right side of the loft, you'll discover the second guest bedroom and a guest hall bath. At the end of the hall awaits the third guest bedroom, accompanied by an additional bonus room ideal for a hobby room, game room, or studio—a versatile space limited only by your imagination. The finished walkout basement provides even more opportunity for leisure and entertainment, with additional living space that can be customized to suit your preferences. There's also a workshop area and ample storage in the unfinished basement, along with plumbing in place for an additional bath if desired. With its desirable location and unparalleled amenities, including the captivating pond view, 207 Pondview Ct presents an extraordinary opportunity to own a home that combines comfort, style, and natural beauty. Don't miss out on this chance to experience the charm and tranquility of Crestview living at its finest. Schedule a viewing today and make this dream home yours!

207 Pondview Ct, Chestertown

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

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

349 & 351 High St, Chestertown

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

List price to be opening bid at online only auction. Auction to take place to the Auctioneer's website. Bidding begins Saturday, April 6th & ends Thursday, April 11, 2024 at 12:00 pm. Exceptional opportunity to purchase a 12-Unit Apartment Complex comprised of 3 adjacent buildings. 11 out of 12 units are currently rented. Location: Chestertown is in Kent County; the apartment complex is conveniently located just a few blocks over the Chester River Bridge (Rte 213). The property has a convenient location near dining, shopping, schools, recreational facilities, and access to transportation routes. The building is located blocks away from Washington College, the University of MD Medical Center and the Downtown Historic District. **Current Gross Monthly Scheduled Rent of $14,044** **Current Annual Gross Scheduled Rent of $168,528** Each Unit is a 1 bedroom, 1 bath single level apartment. Rent Roll: 321 Calvert St rented for $1050/month. 323 Calvert St rented for $920/month. 325 Calvert St rented for $1150/month. 327 Calvert St rented for $1300/month. 329 Calvert St rented for $900/month. 331 Calvert St currently vacant. 333 Calvert St rented for $1180/month. 335 Calvert St rented for $1299/month. 337 Calvert St rented for $1445/month. 339 Calvert St rented for $1400/month. 341 Calvert St rented for $1200/month. 343 Calvert St rented for $1200/month. Annual expenses are approximate: $4,200 for insurance, $4,000 for water/sewer, $1,200 for lawn care, $2,500 for maintenance $1,600 for Gas/electric.

343 Calvert St, Chestertown

Listing courtesy of Alex Cooper Auctioneers, Inc.. Contact:

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

22956 Fairgale Farm Ln, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

3 Beds 2 Baths
Price Reductions!!! This deal just got a good bit sweeter...Escape to the Country! This home is perfect for the outdoor enthusiast. Bring the horses, dogs, chickens, hunters, hobbyist, name it. 15 acres, with small pond and open areas for your animals, sports field, fire pit or huge gardens. Chicken coop, air rifle only shooting range, basketball court, wooded acreage with walking or biking trail and hunting possible all part of what makes this place a dream come true. In the home enjoy large family room with propane fireplace, beautiful kitchen with stainless steel appliances and granite counters. Custom cabinets and built-ins, wood, laminate, and tile floors throughout. Entry level and second level bedrooms. Ready to relax head to the screened porch for quiet evenings. Hot tub hookup in place. Shed and outbuilding provide endless hobby, farm, or craft options. The 30 x 36 metal building has a large open space with multiple smaller rooms with electric and heat. Working at home? Talkie WiFi is available. RV hook-up at both the house and the outbuilding. Underground dog fence and 2 collars will stay . Metal building is in good shape but being sold “as is”. Abandoned underground oil tank on site. This type of property does not often come to market. DONT MISS IT! Home is on a shared R-O-W. No drive-bys. Pets on site so please provide as much notice for showings as possible.

118 Westwood Ln, Chestertown

Listing courtesy of Berkshire Hathaway Homeservice Homesale Realty. Contact: (800) 383-3535

3 Beds 3 Baths
Discovery your sanctuary on this 6 plus acre property, nestled on the outskirts of Chestertown. The property houses an abundance of wildlife such as deer, turkey, fox, and ducks! You might even find a beaver swimming up the creek. Thoughtfully updated, you won’t want to miss this a little over 1600 sq ft 3 bedroom 3 bath home, which includes two en-suites. A 420 sq. ft addition was completed in 2023, which boasts white oak flooring, high end bathroom finishes and a tranquil master bedroom. Additionally, you will find a brand-new kitchen where modern elegance meets farmhouse charm. Adorned with shiplap accents, a farmhouse sink, and stunning two-tone cabinets, this culinary haven is as stylish as it is functional, including new stainless steel appliances. It doesn’t stop there, the remainder of the home includes refinished hardwood floors, new tile throughout the kitchen and hall bathroom, all new baseboard, window and door trim, updated light fixtures as well as finishes. In 2022, the exterior received a complete makeover with a new deck, sheathing, vinyl siding, upgraded soffits, and exterior doors, while brand new Jeld Wen windows adorned with sleek black trim enhance both style and functionality. New insulation was added to the attic to create an efficient home. Utilize the unfinished basement (1200 sq ft), located within the footprint of the original home, for plenty of storage space to accommodate your belongings and keep your living areas clutter-free. Stay connected to the world with access to two fiber internet services, ThinkBig and Talkie. Whether you're working from home or streaming your favorite shows, lightning-fast connectivity is always at your fingertips. Centrally located, this property is just 42 miles to Dover, Delaware, and 53 miles to Annapolis, Maryland. For boat enthusiasts, it's a mere 4 miles to Jellyfish Joel's or Tolchester Beach, and less than 10 miles to Rock Hall, providing easy access to some of the area's most popular waterfront destinations.

9816 Fairlee Road, Chestertown

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

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

8757 Orchard Dr, Chestertown

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

3 Beds 2 Baths
Don't miss your chance to own this charming rancher located in the sought-after community of The Grove. With over 2000 sq. ft., three bedrooms, two bathrooms, and an open floor plan that bathes the space in natural light, it's a perfect blend of comfort and privacy. Nestled in a sprawling 1.23-acre yard, partially fenced for added privacy, this residence is a haven in a quiet cul-de-sac within the renowned Queen Anne's County school district. The well-designed layout ensures privacy with the primary suite and en-suite cleverly separated. The primary suite, featuring an en-suite bathroom and walk-in closet, provides a tranquil retreat. The modern kitchen sets the stage for culinary delights and lively gatherings and is perfect for culinary adventures. The attached 428ft garage, equipped with a generator, has been converted to add additional living space perfect for an entertainment, theatre, or game room. What sets this home apart? A detached garage/versatile pole barn adds both functionality and charm, perfect for any enthusiastic hobbyist! Restaurants, beaches, and marinas are all within 2 miles, offering plenty of sunshine fun! Perfectly positioned just a few short miles from Centreville or Downtown Chestertown showcasing festivals, farmer markets, restaurants, walking trails, parks, and artisan stores galore! Minutes to 301 for easy commuting to Annapolis, Baltimore, DC or Delaware.

209 Myers Rd, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453

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

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

201 N Water St, Chestertown

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

Start Your Search