The median home value in Chestertown, MD is $379,989.
This is
higher than
the county median home value of $301,300.
The national median home value is $338,100.
The average price of homes sold in Chestertown, MD is $379,989.
Approximately 42.33% of Chestertown homes are owned,
compared to 50.71% rented, while
6.96% are vacant.
Chestertown real estate listings include condos, townhomes, and single family homes for sale.
Commercial properties are also available.
If you see a property you’re interested in, contact a Chestertown real estate agent to arrange a tour today!
Lovely all one floor living in quiet neighborhood with updated features throughout! Brand new gorgeous kitchen with white shaker cabinetry featuring dovetail construction soft close drawers, solid butcher block countertops, tile backsplash, large island, brand new stainless steel appliances and much more! eng hardwood flooring, recessed lighting, vertical custom ship lap, gas fireplace, screened porch opportunity and much much more! ABSOLUTE MUST SEE MOVE IN READY HOME!
Prime Investment Opportunity in Chestertown with Leases In Place!!! This duplex property offers versatility, upgrades, and endless potential in a central Chestertown location. Conveniently situated across from Kent Plaza Shopping Center, near Washington College, and just minutes from the YMCA. This property is perfect for live-in owners, investors, or those seeking multi-use functionality .Excellent potential for a home business, in-law suite, or rental income from one or both units! With a prime location, countless upgrades, and flexibility, this diamond in the rough is ready to shine. Don't miss the opportunity to make it yours! Unit A: Bright & Spacious 2 Bed / 1 Bath This well-appointed 2-bedroom unit offers a comfortable and inviting living space. Large Living Room Area Updated kitchen with new Vinyl flooring and fixtures, perfect for cooking and separate Dining area. Convenient in-unit laundry with a stackable washer/dryer to simplify daily life. Refinished oak floors complemented by new ceiling fans, faucets, lights, receptacles and Freshly Painted for a polished look. Recently upgraded bathroom featuring Vinyl floor and a fresh design. Dedicated front parking for convenient and private access. Unit B: Modern 1 Bath Studio with Private Access This updated studio unit is ideal for a tenant seeking comfort, privacy, and convenience. With thoughtful renovations and modern upgrades. Private parking area with a safety light for added security and convenience. Dedicated side entrance featuring a new porch with safety rails and a durable cement base. Vinyl flooring throughout for a fresh and modern feel. Fully renovated kitchenette and bathroom, providing all the essentials in a sleek design. Exterior Highlights Newly installed apron driveway allows for seamless in-and-out access and parking around the house. Regraded landscaping with underground drainage ensures quick water management. New siding, trim, and gutter-guard gutters offer low-maintenance protection. Dependable pest/termite policy transferable to the new owner. Shed for additional storage Septic pumped and Well sealed in January 2025 for peace of mind. Registered with separate addresses for county emergency services. A wall divides the units but includes an existing door for easy conversion back to a single-family home if desired. Excellent potential for a home business, in-law suite, or rental income from one or both units!
2-acre wooded parcel on L Road. Short distance to Chestertown and amenities. See Documents for additional information.
Chesapeake Landing offers a voluntary Home Owners Association. At $40 annually, community members have access to both Worton Wharf and Mill Creek Marinas. Ramps provide small craft access to Worton Creek. Lot failed percolation Test in March of 1989.
Nestled along the tranquil western shore of the Chester River, this beautiful townhome in Chester River Landing offers an unparalleled waterfront living experience with direct water access and captivating water views. Just a short stroll from the historic heart of Chestertown, MD, it combines modern luxury with timeless charm. This elegant 3-bedroom, 2.5-bath residence is designed to maximize comfort and style. The spacious living areas are bathed in natural light, enhancing the serene ambiance of this waterfront haven. The open-plan living and dining areas flow seamlessly into the well-appointed kitchen, equipped with top-of-the-line appliances and ample storage. The master bedroom is a true retreat, with easterly river views and an ensuite bath. The additional bedrooms are generously sized, perfect for family or guests. The 3.5 baths are elegantly designed, featuring modern fixtures and finishes. One of the standout features of this home is its perfect vantage point for watching the daily sunrise. Imagine starting your day with a cup of coffee on the balcony, as the first light of dawn reflects off the calm waters of the Chester River while rowing teams begin their daily workout. Whether you're seeking a peaceful waterfront retreat or a picturesque spot to entertain, this townhome offers it all. The community amenities of Chester River Landing further enhance the lifestyle, with walking paths, swimming pool, private pier with available boat slips for purchase or lease, outdoor grilling and beautifully landscaped common areas. Discover the unique blend of history, luxury, and natural beauty at this waterfront home on the Chester River.
Prime Commercial Space located on a highly visible and well traveled main road in Chestertown, MD! This versatile 2064 sqft office space offers a fantastic opportunity for a wide range of businesses to serve the local communities as it is zoned CC. This opportunity could be perfect for an investor or business owner looking to purchase a cash flowing asset with favorable returns. Previously set up as a medical office, this property boasts a spacious waiting room, front desk and office, private kitchen/break area, billing room/private office, 3 patient rooms, 2.5 bathrooms and a wheelchair accessible ramp. The parking area allows for 8 cars to be parked comfortably for employees and clients. The roof was replaced less than 5 years ago & the shed is included for additional storage space. With a little cosmetic work (paint, etc) to make it your own, this property could be ready for your business to open its doors in no time!
Welcome to 317 Union Church Rd, Stunning Custom Built Farmhouse with all the bells and whistles perfectly sited on over 1 acre. Open concept yet defined spaces allow this home to function wonderfully for entertaining and everyday living...The home exudes style and hospitality from its covered wraparound plantation porch through to the welcoming extra wide entry, seamlessly flowing to the gorgeous light filled designer kitchen (breakfast island, SS appliances, quartz countertops, farm sink and a custom pantry by California Closets), adjoining dining area and a spacious living room with cathedral ceiling. The sleeping zone offers 4 comfortable size bedrooms and 3.5 baths. The primary bedroom is enhanced with a trayed ceiling, walk-in closet, lavish bath with tiled shower and double vanity. Other highlights of the home include custom bench/locker area, Jack & Jill bath, separate laundry room, powder room, LED designer lighting throughout, paddle fans, recessed lighting, black windows, USB outlets, back patio and to top it off a climate controlled garage. Just a few miles from picturesque historic Chestertown, easy commute to Easton, Annapolis and MD/DE beaches! Come enjoy the Eastern Shore -fishing, crabbing piers, playgrounds, bike/walking trails, parks and so much more! This home will be love at first sight, put this on your MUST SEE list!! Schedule your showing today!! Professional pictures coming soon. Note - current photos are from new build in 2021.
Discover the perfect blend of modern design and rustic charm at 204 Pine Cove Lane, a stunning 3-bedroom, 2.5-bathroom home built in 2021. Tucked away on a secluded lot and surrounded by picturesque farmland, this property offers unparalleled privacy and tranquility—a true sanctuary for those seeking a peaceful retreat. Step inside to be greeted by a thoughtfully designed interior, featuring sleek, contemporary finishes and an open-concept layout that effortlessly combines style and functionality. Expansive windows frame the idyllic countryside views, filling the home with natural light and creating a warm, inviting atmosphere. Situated just minutes from Chestertown’s historic downtown, with its charming shops, restaurants, and waterfront attractions, this home perfectly balances rural serenity with modern convenience. Experience the beauty of country living with all the modern comforts you desire at 204 Pine Cove Lane—a home where every day feels like a retreat.
Your dream home is waiting! This remodeled home is waiting for you in the serene water-privileged community of Chesapeake Landing, just minutes from downtown Chestertown. The community offers exclusive access to a boat ramp, a small marina with boat slips, picnic area, and picturesque walking trails. This inviting 3-bedroom, 2-bath residence offers an ideal blend of comfort, convenience, and outdoor living. New luxury vinyl plank flooring has been installed in the living areas and upstairs bedrooms. The kitchen has been remodeled with brand new countertops and a designer sink and faucet, along with newer appliances. Additional updates include a new hot water heater, water softener, and whole house water filter. The side entry door has been replaced, and much of the home has been freshly painted. The rear deck and yard are perfect for your summertime barbecues, or just sipping a morning cup of coffee. Need storage for those outdoor activities? The expansive shed is ideal for storing kayaks, bicycles, lawn equipment, and more. INCLUDES A 1-YEAR HOME WARRANTY. The HOA is voluntary and less than $50 per year. Don't miss this opportunity to own a charming home with modern updates, lovely outdoor space, and unique community amenities. Contact us today to schedule a private tour and experience the tranquility and charm of this exceptional property.
Welcome to the historic Fannie Stuart home, c 1885 - a delightful Victorian home, with the perfect blend of classic elegance and modern comfort, blocks to downtown historic Chestertown and all it has to offer. This special residence boasts four spacious bedrooms, and two beautifully renovated bathrooms, offering ample space for relaxation and entertaining. Step inside to discover a warm and inviting interior featuring traditional wood floors, crown moldings, period touches throughout, and built-ins that enhance the home's character. Natural light pours in through the oversized windows, creating a bright and cheerful atmosphere throughout. You'll be pleasantly surprised by the tastefully updated chef's kitchen - where everyone will want to be - a sunny and comfortable living room, banquet sized dining room, a handsome full bath, and an added bonus room that could be used as a sun room, den, or even a 5th bedroom. The upper levels include 4 generous bedrooms with tree top views, and the other full bathroom. The exterior of the home is equally appealing, with an inviting front porch - a window to the neighborhood - that welcomes neighbors to join you. The low-maintenance lot, which is fenced in the rear and wonderful for pet parents, is adorned with trees and lush greenery providing a tranquil setting for unwinding after a long day. Enjoy peaceful views of the garden from one of two patios, making it an ideal spot for morning coffee or evening relaxation. Additional features include easy parking behind if you choose not to park out front, and storage space in an outdoor shed. With its timeless charm and modern amenities, this Victorian gem is ready to welcome you home. The Chester River, theater, weekly Farmer's Market, boutique shops, popular town events, and dining are all within a few blocks. Don’t miss the opportunity to make this enchanting property your own!
Welcome to this charming 3-bedroom, 2-bathroom rancher, offering the perfect blend of comfort and convenience with one-level living in the desirable Chester Harbor community. Set on a spacious .76-acre lot on the Queen Anne's side of the Chester River, this home is ideally situated in a water-oriented neighborhood, perfect for boating enthusiasts and nature lovers alike. The home boasts a large primary bedroom with its own private bath and an impressive walk-in closet, which includes a cedar section for added storage and warmth. The kitchen and dining area, featuring newer flooring (installed just two years ago), create a modern, inviting space for meals and family gatherings. The kitchen is equipped with updated appliances, ensuring a functional and stylish area for cooking. Outside, the fenced yard—perfect for both kids (two- or four-legged)—provides a safe and spacious environment to play and explore. The fence, installed just four years ago, adds a secure touch to the property. Additionally, the detached two-car garage offers ample storage for vehicles, tools, or water toys.
This end unit waterfront condo in Scott's Point has beautiful water views up and down the Chester River! It is a light filled gem with water views from every window. It has been impeccably maintained and offers wood floors, fireplace, plantation shutters, gourmet kitchen, front and back porches, second and third floor balconies and much more. There are two deeded slips (4ft. MLW) at the community dock, one with a 7 1/2 ton lift. The first floor open floor plan has a kitchen, living room, dinning area, den and half bath. The master bedroom and bath are on the second floor with two walk in closets. There is also a laundry room and home office. The third floor has two bedrooms, two full bathrooms and a sitting room with kitchen conveniences. There is plenty of storage on all three levels. Come and enjoy the water, the views and the conveniences of living in historic Chestertown!
Move-in ready and waiting for you! Start the new year in this charming 3-bedroom, 1-bath rancher. The brand-new kitchen is a showstopper, featuring sleek granite countertops, stylish new cabinets, and stainless steel appliances. Durable and attractive LVP flooring flows seamlessly throughout the home, creating a low-maintenance living space. Freshly painted from top to bottom, this home feels brand new. Enjoy your mornings or evenings on the new paver patio or front covered porch perfect for relaxing or entertaining and make use of the 8x8 shed for all your storage needs. With an HVAC system, roof, and BAT septic system just 9 years young, this home offers peace of mind for years to come. Situated in a water-oriented community, the optional $25 HOA grants access to community water privileges and park access. Conveniently located just minutes from Chestertown and within walking distance to Round Top Park, this is a must-see property! Whether you're starting fresh, downsizing, or seeking a perfect getaway spot, this home checks all the boxes. Schedule your showing today!
? Just Renovated Creekside Beauty – Move-In Ready! ? Discover your dream home with this beautifully renovated 4-bedroom, 2.5-bath gem that overlooks a serene creek. Perfectly blending modern upgrades with cozy charm, this property has everything you need and more! ? Key Features: Spacious 2-Car Garage Bonus Room: Use as a 4th bedroom, home office, or entertainment haven! Brand New Roof for peace of mind. Updated Bathrooms with modern finishes. Fully renovated kitchen with quartz countertops and stainless steel appliances. New HVAC systems with dual zones for ultimate comfort upstairs and downstairs. All New Flooring and freshly painted throughout. Step outside to enjoy your restored decks with stunning water views – perfect for relaxing or entertaining. Conveniently located near shopping, restaurants, and more! Don’t miss this opportunity to own a slice of paradise. Schedule your showing today! ??
ONLINE AUCTION: Bidding begins 2/28/2025 @ 10:00 AM. Bidding ends 3/4/2025 @ 12:20 PM. List Price is Suggested Opening Bid. Lot of Land located in Chestertown, Maryland within Kent County. Property is in close proximity to all the attractions in Chestertown, Maryland. Property is Vacant. Easy Access to Major Traffic Artery Chestertown Road. Deposit: $5,000.
ONLINE AUCTION: Bidding begins 02/28/2025 @ 10:00 AM. Bidding ends 03/04/2025 @ 12:15 PM. List Price is Suggested Opening Bid. Lot of Land located in Chestertown, Maryland within Kent County. Property is in close proximity to all the attractions in Chestertown, Maryland. Property is Vacant. Easy Access to Major Traffic Artery Chestertown Road. Deposit: $5,000.
ONLINE AUCTION: Bidding begins 02/28/2025 @ 10:00 AM. Bidding ends 03/04/2025 @ 12:10 PM. List Price is Suggested Opening Bid. Lot of Land located in Chestertown, Maryland within Kent County. Property is in close proximity to all the attractions in Chestertown, Maryland. Property is Vacant. Easy Access to Major Traffic Artery Chestertown Road Deposit: $5,000.
Welcome to Chester Harbor. Great starter or downsizer, 3 bed 2 bath rancher awaits new owners. The floor plan includes generous Eat -in kitchen and large living room, separate laundry, and a huge screened in porch for picking crabs, parties, or just relaxing. New flooring , fresh paint, and new kitchen counters are a few of the recent updates. Tree lined rear yard and front holly hedge provide surprising privacy. Close to Historic Chestertown and many local points of interest. Easy drive to tax free DE shopping. Voluntary HOA is $25 a year and provides for community water access and park privileges. Shed is " AS IS".
Discover serenity in this charming 2-bedroom, 2-bath oasis with 1,272 sq ft of living space. Nestled in the Chesapeake Landing community, enjoy proximity to Worton Creek's stunning views and easy access to the Chesapeake Bay. This home boasts enchanting features, including a captivating spiral staircase and elegant galvanized tray ceilings that enhance the vibrant, light-filled living area. Relax on the easterly front porch or open side deck, surrounded by nature's beauty and wildlife. With a fully encapsulated crawlspace, tankless hot water heater, and a well-equipped kitchen, this home is truly move-in ready for your peaceful Eastern Shore retreat.
Two secluded wooded lots with approximately an acre total. The existing homes on the property are of little value. There appears to be electric run to the brick house. The county does not have well or septic records so buyer would need to perform perc test to build. There is a 16' right of way to access which has not been maintained. Buyer to do any due diligence. Could be a great hunting property!
Brick rancher located on the corner of Greenwood and Glen Street in College Heights offers a large screened porch, eat-in kitchen and dining room. Home is convenient to downtown historic Chestertown , Washington College and hospital. Property is served with public water/sewer. Underground oil tank has been removed and the crawlspace is encapsulated.
An adorable cottage with water views of the Chester River! Nicely maintained cottage featuring 3 bedrooms, 2 full baths with all the big ticket items completed. Newer Well and Septic, HVAC and newer Metal Roof just leaves you with finishing touches on the interior as you see fit. Currently used as a rental. Also features a detached workshop and detached garage. If you are a boater, bring your boat and the Deep Landing Boat Ramp is just minutes away . Very affordable home in our area, don't wait on this one! Back on the market at no fault of the seller! Schedule your showing today!
This prime commercial lot offers an exceptional opportunity for your next business venture. Situated on Haacke Drive, this 0.96+/ -acre parcel is zoned C-1, which allows for a variety of commercial uses. With limited commercial land available in the town and county, this is a rare find in a desirable location with great potential for visibility and customer traffic. There is also potential for R-4 (Residential) zoning, depending on the town's planning and zoning approval. Ideal for retail, office space, or service-oriented businesses, the property is ready for development. Buyers are encouraged to check with the town regarding specific zoning regulations, potential use, and public water/sewer hook-up fees to ensure a smooth development process. Whether you’re looking to expand your business or invest in a growing area, this lot offers the perfect foundation for success. Don’t miss out on this rare opportunity!
A highly coveted Chester River waterfront just minutes from Historic Downtown Chestertown. This large home has an ample sunroom overlooking the yard to the Riverfront, an in-ground pool within the 100' buffer, a dock with 3+ MLW, an expansive primary suite with sweeping water views, a private space for a home office, playroom, or in-law suite, and a detached three car garage for toys, vehicles, and storage. All situated on almost one full acre. Brand new upgrades since Sept '24 include central AC, roof, refinished hardwood floors, and paint throughout. With easy access to Morgnec Rd, Rt. 301 is only 12 minutes away... which leaves you only an hour's drive from Wilmington, DE or Philadelphia, PA. And into the heart of NYC in less than three hours. Escape to the Eastern Shore lifestyle!
Welcome to Chester Harbor - a family oriented place to live! The Chester Harbor Community has a voluntary HOA of $30/year, which offers water access, a beach, community events, and a playground. Close by is Round Top Park offering tennis, pickleball, and basketball courts, a playground, and a pavilion. Minutes from Chestertown's historic waterfront, restaurants, shopping, and marinas. Queen Annes County Schools! Comfortable serene and convenient - this well cared for home has hardwood floors and a new hot water heater and water tank on 3/11/2023 and an attached workshop!
