The median home value in Chestertown, MD is $380,000.
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 $380,000.
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.
Welcome to your new home in the vibrant community of Chestertown! This beautiful 3-bedroom, 3.5-bath townhome features an open layout perfect for modern living. The heart of the home is the stylish kitchen, equipped with contemporary finishes and ample storage. Enjoy relaxing in the spacious living area or step outside to your private deckâideal for entertaining or soaking up the sun. The attached garage offers convenience and additional storage. Located just minutes from the new YMCA and other local amenities, this home is perfect for those seeking an active lifestyle. Plus, with solar panels installed, you'll enjoy energy efficiency and lower utility bills. Don't miss this opportunity to own a piece of Chestertownâs growing charm! Schedule your tour today!
Eastern Shore of Maryland Waterfront Cottage is perched on the banks of Rosin Creek in Queen Anneâs County. Cozy, comfortable home welcomes you with wrap-around water views in a serene wooded setting. With convenient single level living, the three bedroom two bathroom home offers a flowing floor plan bright with natural light and custom upgrades. Relax and enjoy views from the private walkout deck or stroll down to your dock for boating, fishing and water activities. Located in the popular waterfront community of Chester Harbor you are a walk away from the community dock and picnic area. This property is a little gem located just 3-miles from downtown historic Chestertown. Chestertown is located 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 beautiful period homes, sought after shops, galleries, live theater and waterfront park. Dining options include an oyster bar, bakery, cafes, luncheonette and fine dining restaurants. The landing at the foot of High Street leads to the Chester River Walk where you can take a river cruise on the Chester River Packet. 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, waterfront park, rails-to-trails and water activities.
Discover this nearly new, beautifully maintained home in Chestertown. Featuring luxury vinyl flooring throughout, white cabinets, granite countertops, a spacious living room, an eat-in kitchen area, and a covered patio, this home offers a comfortable and stylish living space. The large primary bedroom suite and additional spacious bedrooms provide ample room for relaxation and privacy. Enjoy the convenience of living close to Historic Downtown Chestertown, where you'll find a variety of amenities, including shops, restaurants, cafes, art galleries, and the picturesque Chester River waterfront. Take advantage of special financing programs, such as zero-down payment loans and closing cost assistance, to make homeownership more affordable
Hidden within the wandering gardens, you will find this meticulously maintained home with seasonal water views of the Chester River in a quiet family-friendly community just minutes from Chestertown. The spacious front and back yards are private oases with just about every tree or plant one can think of; a true gardner's dream. Enjoy the fall colors from the back screened-in porch. Inside you will find hardwood floors throughout the entire home. The open concept kitchen features custom maple cabinets, marble countertops, island with hanging pot rack and flows naturally into the dining room and back porch. The kitchen and breakfast nook truly celebrate the views of the backyard gardens. The main floor also features a large living room with wood burning stove and a spacious primary bedroom and full bath. Four more bedrooms upstairs and a sixth in the full basement. The full basement has tons of storage space and room for a workshop. The current owner did a major renovation in 2016: Architectural shingle roof, completely redone kitchen, and heating/air. 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 parks. Chestertown is home to many festivals and an award-winning weekly Farmer's Market. See it today.
This 1500 sq. foot rancher sits on a nice open lot with plenty of parking and room to grow and make your own . Main level offers eat in kitchen, an oversized living room with fireplace , four bedrooms and two full baths. One of the bedrooms could make a perfect home office. This home has been freshly painted and new flooring. This will get the new owners a fresh start while they decide on other updates along the way. The basement has been fully waterproofed and has had extensive work completed with a transferable warranty to the new owners. You have a full space to finish off as you would like. Come see, bring your ideas, and make your own.
Well Maintained rancher with major renovations. Updating Kitchen including recently new stainless steel appliances and cabinets, Bathrooms, HW flooring refinished, fresh Paint throughout, move-in condition. New boiler, new water heater & new central A/c in 2011. Full basement -Office/den in basement w/ built-in book shelves and tile floor that has a separate entrance. Laundry area in basement. Partially fenced in rear of property. Attached garage with storage room. Blacktop drive & new landscaping. Located close to Chestertown, Rock Hall and easy drive to Middletown, De.
From the moment you drive up to this beautiful home, you are struck by the beautiful landscaping that complements the home, includes a rain garden, cutting garden, wildflower garden and a walkway that leads to an outdoor patio that provides such a great space for outdoor living. The orchard has peaches, plum, apple trees as well as berries and grapes. The enclosed screen porch overlooks the patio and provides a great space to enjoy the outdoors. There is a 2.11 additional parcel, deeded separately surrounding the property that has walking paths. Hunting is allowed, or just enjoy the beauty and solace of a forest walk. Wildlife is plentiful. Quaker Neck Landing is about 1.5 miles away on the Chester River and offers docks and a boat launch. Continuing inside, there is a covered porch at the entrance and the gracious foyer showcases the open living space that is so welcoming. The kitchen is open to the living room, the dining area, but there is a tucked away office providing another getaway area. Two bedrooms, one full bath on the main level, an amazing kitchen with all the bells and whistles, a laundry room complete with a kitchen garden window, and a screened in porch. This home offers a second level with a primary bedroom, walk in closets, additional walk in storage areas and an amazing master bath. The den/library is just waiting for you to appreciate! Improvements include a fully inspected and pumped BAT system in 2024, There is a new Trane high efficiency heat pump, a new electric water heater and a whole house Generac generator. The crawl space has been fully encapsulated and there is a dehumidifier in the crawl space. The 20x40 Amish built pole barn/garage boasts a wood working shop, two garage spaces, RV doors and tons of storage in the loft area, accessed by steps. This home with all the amenities is a must see, just minutes from Chestertown, but such a peaceful setting.
Welcome to this lovely home with a detached garage in the community of Woods Edge in Kent County! The home features three spacious bedrooms with built-in closets, a full bath with dual vanities and a soaking tub, a family room with a fireplace that opens to the kitchen with appliances and wooden cabinets, and a sunroom with tiled floors and a sliding door that leads to the backyard. The home is located near the Chesapeake Bay and is just a 10-minute drive to the beaches and marina. Additionally, it is 9 minutes away from the ACME market and local restaurants.
This fabulous craftsman style 3 bedroom home, is perfectly situated to enjoy the beauty and tranquility of the East fork of Langford Creek/Bay with approximately 150' of shoreline and sandy beach. Great room was added in 2001, with a loft and cat walk to offer added living area. Updated kitchen in 2022 The subject property is one of 5 waterfront properties that belong in the Cacaway Farm Cooperative Housing Corporation, an exclusive farm housing community. Experience the same benefits of a fee simple ownership but share the cost of expenses. Enjoy privacy and the use of your own waterfront with sandy beach by way of a gentle slope to the water, launching kayaks or canoes while deep water slip at the community dock is also included. A south facing direction on the water side offers wonderful & welcoming breezes throughout the summer. It is improved by 2 car heated garage built in 2006 plus a smaller area for storage with a bonus area above. The area above has radiant floor heat. A BAT septic was installed in last 4 years, with a new shared sewage disposal area maintained by the county. Please do not drive down Cacaway Farm Lane without an appointment. This is a private lane.
Ranch home located in Primrose Point neighborhood( Queen Anne's County with Chestertown address), only ten minutes from downtown Chestertown. This home offers large rooms that could be modified to create a formal dining room and seperate family room if desired. The swimming pool has not been used for two years. This property is being sold "AS-IS". Sign posted.
Tucked away in a wooded setting in a quiet neighborhood just a block off the Chester River you will find this well built welcoming home. The well designed main floor layout includes a living room, dining room, and eat in kitchen plus a year round spacious sunroom overlooking the back yard and the open space beyond. This split level has the ideal arrangement with just 3 steps down to the lower level with family room, laundry room and full bath and just 9 steps up to the bedroom level with 3 bedrooms and full Jack and Jill style bath between Primary Bedroom and the hallway to the other 2 bedrooms. The home has been well maintained with recent updates including a new roof, new water heater, and an encapsulated crawl space complete with dehumidifier. Outside you will find numerous shade trees, native plantings and brick pathways that lead you through the fenced yard. There is even a chicken coop out back if you want to have fresh eggs every day! Less than a 5 minute drive to Historic downtown Chestertown with its unique shops, dining options, and numerous activities!
This charming 2-bedroom, 1-bath villa was beautifully renovated in 2020 and offers low-maintenance living on one-level. Step onto the welcoming front porch and enjoy the oversized corner lot with a fenced-in backyard, perfect for outdoor relaxation. With ample storage space and a deeded parking spot, this home is both practical and inviting. Located just 5 minutes from Rock Hall and close to the Chesapeake Bay and Tolchester Marina, this property is a fantastic opportunity in Kent County for under $200K. Don't miss out on this gem!
This charming Cape Cod is situated on a desirable corner lot in Kingstown, from here you can walk or bike ride from historic Chestertown. The home features a modernized kitchen, a spacious living room, and a dining/family room, along with a convenient first-floor bedroom. The second-floor houses two additional bedrooms and a full bath. Outdoors, you can unwind on a 14 x 10 deck, set in a private backyard enclosed by a privacy fence. An oversized three-car detached garage offers approximately 900 sq ft of space, complete with a storage loft andelectricity.. Although the property has a Chestertown address, it is actually on Queen Anneâs County side of the Chester River. The area is rich with activities, including a weekly farmers market, local events, boating opportunities, dining, shopping, and access to the YMCA. Plus, it is close to Washington College, adding to the areaâs vibrant community life. Electric to Garage applied for and awaiting final permit. Seller offering $2,500 for carpet replacement
Chester River Waterfront with dock and 4-5â water depth. Enjoy sunsets and western views over the upper Chester River while having the opportunity to crab and fish from your own Dock! 5 bedroom and 3 full baths, sunroom, spacious kitchen with island, and spacious lot. Reasonably priced waterfront under $500,000.00. Great vacation home opportunity! All improvements being sold in "AS-IS" condition.
Now offered at $789,000, this coastal waterfront condo with expansive views of the river is located in Kent County's coveted Chester River Landing where homeowners enjoy exclusive amenities such as a private marina, community pool, fire pit, gas grills, and kayak launch. If you like entertaining, you will LOVE the spacious kitchen with LARGE center island. This turn-key unit is upgraded throughout and offers a deeded deep water boat slip, 2-car garage, and 2 covered balconies! Make the most of Downrigging weekend this year by enjoying the festivalâs fleet of Tall Ships from your very own home. A mere 3/4 mile away is Chestertown's historic downtown, host to our local speakeasy, nationally recognized farmers' & artisans' market, fine dining, walking/jogging path, eclectic shops, a plethora of activities and events throughout the year, and so much more. Summer is just around the corner and there is no better place to be than here on The Chester.
Welcome to 116 Pine Chip Road, a beautifully renovated Cape Cod in the heart of Chestertown, MD, Queen Anne's County. This 3-bedroom, 1 1/2-bathroom home has undergone a complete transformation, boasting new siding, windows, doors, and drywall throughout. The modern upgrades continue inside, where you'll find stunning LVP flooring on all three levels. The main level features two spacious bedrooms, each with double closets, and a full bathroom. The custom kitchen is a chef's dream, featuring a gas stove, upgraded quartz countertops, solid wood cabinets, and stylish open shelving. Upstairs, the primary bedroom offers a private retreat with a mini-split AC/heat unit, a large dressing room, and a convenient 1/2 bath. The finished basement is perfect for entertaining, complete with surround sound, a laundry room, and a utility room. The outdoor space is equally impressive, with a newly installed privacy fence surrounding the backyard. The fence includes three personal gates and one large gate for vehicle access. Additionally, the property features a shed and a detached garage, providing ample storage and workspace. This home is move-in ready and offers a perfect blend of modern amenities and classic charm. Don't miss the opportunity to make 116 Pine Chip Road your new home!
Welcome to your dream home in the charming sought after community of Chester Harbor! This delightful property boasts 3 spacious bedrooms and 2 full updated bathrooms, perfectly designed for comfort and modern living. Step into the huge master bedroom, perfect for all buyers. The finished basement provides versatile additional living spaceâideal for a family room, home office, or play area. The recently renovated kitchen is a culinary enthusiastâs dream, featuring contemporary finishes and high-end appliances that make meal prep a pleasure. Outside, the great yard is perfect for entertaining, gardening, or simply enjoying the serene surroundings. Enjoy the HUGE garage located in the rear of the property. Chester Harbor Community has a voluntary HOA ($30/year), which offers water access, a beach, community events, and a playground. Just around the corner is Round Top Park offering tennis, pickleball, and basket ball courts, a playground, and pavilion. Minutes from Chestertown's historic waterfront, restaurants, shopping, and marinas
UNIQUE 4 BEDROOM/3 BATH CUSTOM BUILT CONTEMPORARY on a corner .37acre lot in the desirable neighborhood of Mile Tree Village. This gorgeous, meticulously maintained home offers all on one floor living in light-filled, easy care, open floor plan comfort. Features include cathedral and vaulted ceilings in the main living area and master bedroom; handsome maple flooring throughout the central living area; a glass doored corner gas fireplace in the living room; ample cabinet, pantry, storage and closet space; an oversized attached two car garage; roofed, sitably sized front and side porches; a lovely large rear patio with awning; and a custom-built stone terrace with a waterfall fountain. Additional household amenities include like-new stainless kitchen appliances; induction cooktop and double wall ovens; a kitchen prep sink; custom granite and Corian counters in the kitchen and bathrooms, a soaking tub and glass walled walk-in shower in the Primary Bathroom ; hardwired home security and fire alarm and sprinkler systems ; a whole house generator, a surround sound system; a central vacuum system; multiple phone lines; automatic garage door; invisible fencing for pets, and the list goes on. The house has two sets of solar panels installed on the rear roof: one owned by the Sellers and the other subject to a power purchase agreement with TESLA. Both sets of panels convey with the house. Professionally maintained landscaping that includes lovely mature flowering shrubs, perennials and trees and an in-ground watering system surround the house. A lockable garden shed sited in a wooded area at the back of the house provides out of the way storage for lawn and garden equipment and supplies. In addition to its many on-site pluses, this wonderful home offers convenient, quick and easy access to Washington college, area schools, parks, doctors, churches, Historic downtown Chestertown, waterfront recreational facilities and shopping centers. APPRAISAL- BASED PRICE REDUCTION! MOTIVATED SELLERS!
Nestled in a prime suburban commercial zone, this versatile property offers 1,300 sq ft of living space, perfect for both residential and/or commercial use. The freshly resealed driveway accommodates up to 6+ vehicles, with the potential for parking lot expansion, ensuring ample space for guests or clients. The property features two inviting front entries: one through an 8x16 sunporch, ideal for enjoying morning coffee or greeting visitors, and another through the welcoming living room with a large bay window that floods the space with natural light. The rear entry provides convenient access to the kitchen and basement. The kitchen is equipped with all essential appliances and features laminate countertops and durable vinyl flooring. A pass-through window connects the kitchen to the sunroom, enhancing the open and airy feel of the building. The basement, with its poured concrete floor and perimeter trench leading to the sump pump, offers potential for additional storage or workspace. The single level structure includes a spacious full bath and three generously sized bedrooms, perfect for a family or for converting into office spaces. This property blends functionality and charm, making it a unique opportunity for those looking to live and work in a suburban setting.
Built in 2005, this like-new home boasts an open floor plan with inviting, bright spaces. The residence features 3 bedrooms, 2.5 bathrooms, and 1,222 square feet of low-maintenance living. Enjoy the convenience of two dedicated parking spots right in front of the home, as well as no outside maintenance. The half bath comes equipped with a stacked washer and dryer for added ease. The spacious living room and dining room seamlessly flow to a sliding door that opens to a rear porch and common grounds, perfect for relaxing or entertaining. Located in Chestertown, this home is in close proximity to Washington College, Chester River Hospital Center, and the Chestertown walking trail, making it an ideal location for both convenience and leisure.
Charming Historic Chestertown investment opportunity! Once updated this building can accommodate two street-front shops and a spacious apartment upstairs. The back of the building has extra living space with a private entrance and full bathroom. The attic is flooded with natural light! One could use the attic as-is for extra storage, or it could be renovated, adding additional living space. Back deck overlooks sweet courtyard, perfect for relaxing. GREAT location and tons of character - enjoy the Chestertown Farmer's Market year round, the Chester River just a few blocks away, shops and restaurants right down the street - you cannot beat this Historic District location and opportunity. Seller has removed plaster walls downstairs and updated the electric. Other updates include: exterior painting, new metal roof and a new deck with entry to second floor apartment.
****BACK TO ACTIVE****** The property is back on the market after the previous deal fell through due to the buyer's inability to secure financing. This now opens up a great opportunity for new potential buyers to step in and make an offer on this desirable home. Seller will consider concessions to the buyer to make the deal work. This is a Charming 2-Bedroom Home on 1 Acre with Scenic Farm Views! This delightful 2-bedroom, 1-bathroom home offers a perfect blend of comfort and charm, nestled on just over 1 acre of lush greenery. As you step inside, youâll be greeted by a spacious formal living room that invites relaxation and gatherings with loved ones. The eat-in kitchen is a cozy space, perfect for casual meals and culinary creativity, while the sun porch provides a bright, cheerful spot to enjoy your morning coffee or unwind with a good book. For those lovely evenings, the screened-in sun porch allows you to soak in the gentle breezes without the worry of pesky insects. With expansive outdoor space and picturesque views of the adjacent farm, this property is ideal for anyone seeking tranquility and a connection to nature. Donât miss your chance to own this charming home in a serene setting!
Welcome to your private oasis! This charming home boasts mature landscaping that provides both beauty and privacy on a large corner lot. . Custom built Cape Cod offers a first floor primary suite, living room with fireplace and built ins, formal dining room and a kitchen with granite counters and updated appliances. Thereâs an open area on the 2nd level ideal for reading or watching TV. Plus 2 more bedrooms and an office. Enjoy the serene ambiance from the large deck, overlooking a picturesque pond with not one, but two enchanting waterfalls. The soothing sound of cascading water creates a tranquil atmosphere, perfect for relaxation and unwinding. This property is a true retreat, offering an idyllic escape right in your backyard. Located just minutes from the Chester River and Chestertownâs historic district.
Spec home located in small 12 home development (to be built). Prestwick offers the best in eastern shore living with the small town charm of Chestertown, MD, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington, DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board or kayak at the new town marina or the many county owned ramps. Design and build the home you want with one of the area's finest builders