The median home value in Chestertown, MD is $269,990.
This is
higher than
the county median home value of $249,900.
The national median home value is $308,980.
The average price of homes sold in Chestertown, MD is $269,990.
Approximately 44% of Chestertown homes are owned,
compared to 42% rented, while
14% are vacant.
Chestertown real estate listings include condos, townhomes, and single family homes for sale.
Commercial properties are also available.
If you like to see a property, contact Chestertown real estate agent to arrange a tour
today! Learn more about Chestertown Real Estate.
9 year old cape with wonderful open floor plan. Nestled in the woods for privacy. Bay water privileges and marina nearby. This property is part of Tolchester Estates.
(Pics are from a prior listing. New pics on the way) Escape to the Country! This home is perfect for the outdoor enthusiast. Bring the horses, dogs, chickens, hunters, hobbyist,...you 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 âas isâ. 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. OPEN HOUSE SAT THE 23RD 12- 2 PM. Pets on site so please provide as much notice for showings as possible.
Situated on 3.28 acres in a "park-like" setting that overlooks the stocked fish pond, is a Ranch-style turn-key home in excellent condition! **Detached two car garage (2019) with electric & new epoxy flooring + 2 additional storage sheds... Al fresco dining on the deck anyone? There's ample room for entertaining! WHAT YOU DON'T SEE - 2023 "all house" Generac Generator, High Speed Fiber Wifi through Talkie, Roof - 2019, Sidewalk - 2019, brand new Gutter Guards, A/C Unit - 2023, Primary Bath Remodel - 2019... The Solar Panels are owned and practically eliminate your electric bill. Have you ever had a $14.00 electric bill?
This fixer upper is a great chance to have a house on a large lot in a prime area just outside of Chestertown. The house itself needs serious renovation and has evidence of smoke/fire damage however has a septic system, well, and great bones. The lot provides 2.4 acres of privacy and tranquility among nature but with the culture and amenities of the town just a short drive away. The property is of an estate and is being sold as-is. Chestertown is located only 90 minutes from DC, Philadelphia, and Baltimore and just an hour from Wilmington.
Well maintained 2 bedroom 1 bath Colonial on .69 acres with winter water views of Fishing Creek! Features Include: Screened Porch * 1-Car Attached Garage * Tilt-in Insulated Double Pane Windows * Large Living / Dining Room Combo with Brick Accented Gas Fireplace * Updated Kitchen with Stainless Steel Appliances * Separate Laundry Room off Kitchen * 2 Generous Sized Upper Level Bedrooms + a Large Bathroom with Separate Make-Up Table. * Dual Zone Central Air, Dual Zone Hot Water Baseboard Heat * Full RV Hookup with Water, Sewer & Electric in Back Yard. *Conveniently located just minutes from all the shops and restaurants Chestertown has to offer, this quaint property offers a little rural lifestyle without the isolation!
Welcome to 27370 Morgnec Rd. Conveniently located and Nestled on .95 acres, this home Features 3 Bedrooms, 1.5 Baths with beautiful Hardwood Oak Floors throughout. Perfect for those seeking the convenience of main level living. Situated just a few miles from the charm of Downtown Chestertown or just minutes away of quick access to US-301. This spacious yard offers a great canvas to create your own outdoor living area and provides ample room to entertain family and friends. From the back deck, experience peace in nature within the surrounding woods. A partially fenced in yard serves the ideal area for your four-legged friends. The 23'X23' Garage offers enough room for your vehicle or space needed to work on projects. This garage is heated with a woodstove and will keep you warm in those cold winter months. Bring your own creativity and this property will facilitate lasting memories for years to come. Showing Times are limited, please call or schedule your tour online. Hope to see you soon!
Fantastic opportunity for instant equity. This property requires renovation but is more than worth the time and the effort. Great house (potential) and a Great neighborhood . Main level has a formal dining room, family room that opens to the kitchen and a living room off the family room for entertaining. Basement is unfinished with high ceilings and lots of potential for additional living space once finished. Upper level has a primary bedroom with a walk in closet and a primary bath in the bedroom as well as 2 additional generous sized bedrooms. This is a great deal for owner occupants and investors alike, Prices to sell quickly, this one will not last. Do not miss out.
Eastern Shore Waterfront Home is set on 5-acres on Rosin Creek in Queen Anneâs County, Maryland. The home is located in a peaceful, wooded setting with lovely long water views, yet it is only a 10-minute drive to Chestertown. Enjoy the private dock for fishing and water activities, or, head out for a 10-minute boat ride up the Chester River to historic Chestertown. Downstairs, the main living area offers a first floor bedroom, full bath, lovely sunroom overlooking the creek, and living room with a fireplace and wood-burning stove. Upstairs are three bedrooms, a full bath and bonus room. The house has an attached garage and also a separate garage and workshop. Set in the quiet community of Royston Shores, Roundtop park is nearby with a basketball court, tennis courts, pickle ball courts and pavilion. Chestertown is located on The Eastern Shore of Maryland, about 90 minutes from Washington, D.C. and Philadelphia. Founded in 1706, it is set on the banks of the Chester River and is home to Washington College and the University of Maryland Shore Medical Center. The walking town features period homes, shops, galleries, live theater and waterfront park. Dining options include an oyster bar, bakery, cafe, luncheonette and fine dining restaurants. The landing at the foot of High Street leads to the Chester River Walk and the Chester River Packet offering public river cruises. Annual events include the Chestertown Tea Party and Tall Ship Downrigging Weekend. Residents and visitors alike enjoy the vibrant arts community, the Saturday Farmers/Artisan Market, parks, rails-to-trails and water activities.
(3 rooms still being renovated - pictures to come March 17th. Living room, laundry and front sitting room) Welcome to this cozy 3 bedroom, 1 bath completely remodeled home with views of the Chester River and a lovely yard full of mature gardens. New heating/air conditioning mini splits, new siding, windows and doors. New electric tankless hot water heater, new washer & dryer, LVP floors, new carpet, new stainless-steel appliances, fresh paint, plantation shutters and new window treatments throughout, electric with solar panels to help absorb energy costs. New front steps, seamless gutters and new lighting. Located in Queen Anne's County, Chestertown MD on a dead-end dirt road. Home has a 12 x 16 treated lumber deck at rear entry and a 10 x 12 shed matching siding, new windows, and new tin roof Enjoy peaceful days and night as this home is located on a no outlet dirt road. The yard is abundant with flowering trees, shrubs and flowers to enjoy your morning coffee or evening sunsets. Annual events include the Chestertown Tea Party and Tall Ship Down Rigging Weekend. Residents and visitors alike enjoy the vibrant arts community, restaurants, shopping, the Saturday Farmers/Artisan Market, parks, rails-to-trails and water activities. Just 25 minutes to the Bay bridge or Middletown, De. Must See!
Modern Cape Cod style home in peaceful Orchard Hill sitting on 1.89 acres. Interior boasts vaulted ceilings, ground floor primary bedroom , upgraded kitchen offering granite counter tops, quality stainless appliances, island with gas cooktop and built-in wine refrigerator. The Primary bedroom includes a luxury primary bath with a jetted tub and stylish tile shower with glass doors. The openness of the mail level is conducive to entertaining and includes the convenience of a bar with sink. Outdoor space is abundant and includes a screened porch, large composite deck with retractable canopy, gazebo and beautiful English cottage gardens which include many native plants. This property provides ample space for gardening or play and offers a peaceful backdrop backing to trees and farmland. It's a MUST SEE.
Be sure to check out the photos - this home has real charm and character! This well-maintained house has been home to the same family since 1975: blacktopped driveway resealed in 2022, new roof 2017, new well 2016, quarterly Pest Service and mature landscaping with a fenced backyard. New washer and dryer and a full tank of propane for use of the attractive oak fireplace. Both bathrooms completely updated 2024. Both large upstairs bedrooms have double windows which allow for maximum light during the day. The property sits on four lots for a total of .69 acres. The quiet community of Chester Harbor has a voluntary HOA which allows for Chester River water access and use of the community area located at the end of Fairview Drive. Round Top Park is close by - ball courts, playground and a pavilion. Close to historic Chestertown and just 45 minutes to Middletown and tax-free shopping!
Price Improvement! Don't miss your chance to own this charming rancher located in the sought-after community of The Grove. With over 2200+ square feet this property offers the perfect blend of comfort and privacy. Three bedrooms, two bathrooms, and an open floor plan create a bright and inviting space. The well-designed layout ensures privacy with the primary suite and en-suite cleverly separated. The modern kitchen 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. Situated on 1.23 acres, partially fenced for privacy, this home is nestled in a quiet neighborhood on a cul-de-sac within the esteemed Queen Anne's County school district. Fenced lot offers additional storage with a 25x32ft detached garage/pole barn perfect for any enthusiastic hobbyist! Restaurants, beach, and marinas are all within 2 miles, offering plenty of sunshine fun! Within Queen Anne County school district and 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.
1900's Bungalow sitting on a 4 Acre Lot out in the country. The dwelling is in need or major repairs or replacement. The property is mostly wooded. Has a new electric service, working well and a existing septic on the property.
This charming 3-bedroom 1 bath home is well maintained and conveniently located - within walking distance to historic downtown Chestertown with its' charming shops and restaurants. Washington College, the hospital and the farmers market are close as well. New carpet and paint and fenced backyard with shed. Priced to sell!
This barely lived in rancher, located in a cul-de-sac, offers breathtaking sunrises and sunsets with amazing panoramic farm views. The open floor plan offers a spacious kitchen, living and dining room combination with a split bedroom configuration. The many windows and cathedral ceiling provide an abundance of light even on the cloudiest of days! Heat pump and electric baseboard heat allow for rooms to be heated separately. Laminated plank flooring is throughout making for easy cleanup and maintenance. 36" wide doorways and grab bars allow for some handicap accessibility. Home has many upgrades that include but are not limited to extra insulation in walls, remote holders in all rooms, thermostats in every room, soft heat electric baseboard units in addition to heat pump, power sliding glass door shade, all upgraded light switched and dimmers, 16'x12' rear deck, water softener and more!
Two perfectly adorable cottages in Tolchester. Both were completely remodeled. The cottages sit on 3 lots totaling about .46 acres. Each has one bedroom, a full bath, kitchen and living areas. The front cottage also has an additional "sleeping loft". Tolchester Beach is located on the Chesapeake Bay and has a beautiful beach and boat ramp. Walking distance to The Shanty Beach Bar and the Tolchester Marina. A great place to enjoy live music, great food and drinks. Each unit has new mini-split systems for heating and cooling. These would be a perfect vacation home or you could live in one and rent out the other. These would also make good airbnb or vrbo properties. The front cottage is approximately 400 sq ft. The back cottage is approximately 750 sq ft. Come check them out!
Prime Location Alert! Nestled along one of Chestertown's bustling thoroughfares, this delightful 3-bedroom, 1-bathroom bungalow exudes charm and possibility. Boasting a coveted Intense Village zoning, this property opens doors to a myriad of opportunities, whether for residential bliss or a variety of commercial endeavors. Step inside to find a generous family room seamlessly connected to the galley kitchen, offering a cozy yet functional layout. Relax and unwind in the screened-in porch or take advantage of the detached 2-car garage, complete with abundant off-street parking. Recent upgrades add to the allure, including a new heat pump with central air in 2021, a fresh roof installment 2022, and plush new carpetingâeach enhancing both comfort and aesthetics. Location-wise, convenience reigns supreme, with proximity to Chestertown's treasures such as Washington College, the hospital, local boutiques, the newest marina, eclectic dining options, and much moreâall just a stone's throw away, promising a lifestyle of ease and accessibility. Overflowing with potential, this property beckons for visionaries and dreamers alike. Please take note, there's an existing lease in place, expiring on December 31, 2024. Don't miss out on this golden opportunity!
"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!
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.
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. Owner Agent.
Welcome to this newly renovated home with stunning upgrades throughout! This charming, easy-living home, in Chestertown, MD has all new LVP flooring, paint and drywall, a brand-new kitchen featuring sleek grey cabinets, stainless steel appliances, a deep sink, backsplash, and quarts countertops. The bathroom boasts a beautifully tiled shower. New washer and dryer on the main floor, and beautiful windows to let in an abundance of natural light. Enjoy almost an acre of land with plenty of room to enjoy the quiet outdoors. This home is located in Queen Anneâs County, close to rt 301, making for a short commute 25 minutes to Middletown, DE, 35 minutes to the Chesapeake Bay Bridge, and lots of local amenities near by.
SMITH-RINGGOLD HOUSE. This exceptional property is a rare find: an authentic waterfront 18th century home with 21st century comfort. Originally a merchantâs 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 homeâs 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 chefâs 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 âsecretâ staff stairway. The third floor has a large sitting room, bathroom, and bedroom, with part of the homeâs 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 artistâs 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 âpainted ladies.â 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 galleriesâbut 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.
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!
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!
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!