The median home value in Chestertown, MD is $380,000.
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 $380,000.
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!
The attention to detail, superior craftsmanship and high end finishes gives this home an "Oh Wow" factor! Located on a point of land overlooking the Chester River Yacht and Country Club's pond and golf course, the views are beautiful and peaceful. The backyard patio with its fire pit and grill allows you to soak up the setting and enjoy the wildlife. There are solid cherry wood floors, marble and butcher block counter tops, large copper kitchen sink, a wood burning fireplace and many other features that enhance the interior living space. The open floor plan makes if perfect for entertaining. There is one bedroom and full bath on the first floor and two bedrooms and two full baths on the second floor. The master bathroom has a jacuzzi tub and shower with its own separate Rennie tankless hot water heater. The master bedroom has a private balcony overlooking the water and manicured lawns. A lovely home in a lovely setting just about a mile from the Historic District of Chestertown.
Welcome to your serene getaway nestled on 2.62 acres of partially wooded land on Urieville Lake! This stunning 4-bedroom, 3.5-bathroom home offers the perfect blend of comfort and privacy, making it an ideal retreat for families and nature enthusiasts alike. With an option of a first floor bedroom there are currently three bedrooms on the second floor and one unofficial bedroom in the basement, thereâs plenty of space for family and guests. The open-concept living area is perfect for gatherings, featuring ample natural light and gorgeous views of the surrounding landscape & lake! Enjoy convenience and comfort with two full bathrooms on the second, one full bath on the lower level and an additional half bath on the first, designed with modern fixtures and finishes. The finished walk-out basement provides excellent additional living space, bath/bedroom & perfect for a game room, entertainment area, or a private office. It also offers direct access to the beautiful outdoors. The property spans 2.62 acres, providing ample room for outdoor activities, gardening, or simply unwinding in nature. The partially wooded area enhances your privacy while allowing for serene nature walks right in your backyard & along the Lakes edge! Located on Urieville Lake, enjoy fishing, boating, and other recreational activities just moments from your doorstep. This private setting is perfect for those looking to escape the hustle and bustle of city life. Urieville Lake is about 35 acres in size and is shaped like the letter Y. The average depth is about 3 feet and supports a standard bass/bluegill fishery and is managed accordingly. Anglers may also occasionally catch other species including pumpkinseed sunfish, brown bullhead catfish, golden shiners and common carp. Interior pictures and layout coming soon!
Nestled on 10 scenic acres just outside of Chestertown, this spacious 3,280 sq ft home offers incredible potential for those looking to earn a little sweat equity. This home is ready for a buyer looking to uncover its true potential. Boasting 3 large bedrooms, a very large room on 2nd level could be a bedroom ? game room ? you decide, 3 flexible spaces that can be used as offices, dens, or multi-purpose rooms, and oversized rooms throughout that offer endless possibilities for customization. Rich hardwood floors and custom doors and woodwork add character and charm, while a full-length sunroom across the front of the house provides stunning views of the surrounding landscape. The spacious kitchen features Amish-built cabinetry, offering both craftsmanship and timeless appeal, along with a large pantry for added storage. The generously sized laundry room offers added convenience. There is so much storage space offered throughout this home. walk in closets, etc. The property includes an outdoor wood furnace (central boiler system), a whole-house propane generator, a shed, large circular driveway and several outbuildings one with small studio space providing ample space for storage, workshops, or hobbies. There is also future development potential with upcoming zoning changes from Rural Character to Community Residential - think subdivision . Please verify all zoning and development opportunities directly with the County. This is a unique opportunity to invest in a property with endless potentialâwhether you're looking for a personal retreat , a large piece of land to call your own, or a long-great investment. Donât miss your chance to make this property your own! Home is being sold AS IS.
Pretty wooded parcel recently surveyed with stakes clearly showing property boundaries. SEE DOCUMENTS for plat and aerial view. Property already has a sewer allocation. Tax record shows 3 acres but recent survey confirms 2.356 acres. There is an old collapsed trailer on site that did have electric at one time. Seller is in the process of removing the trailer and any debris around the trailer so the property will be back in pristine condition soon! This area has also been know for excellent hunting (owner recently took down a couple of deer). Property sits back off the road with a wide gravel right of way back to the parcel. The seller will meet interested parties on Georgetown Rd where a chain is across the right of way. Do not walk the property without the seller or his agent, especially during hunting season.
This impeccably maintained home is a true standout and has it ALL! With 5 spacious bedrooms - with both main level & upper level primary suites - and 3.5 baths, including a main level primary suite with a walk-in closet featuring a premium wood built-in system, dual vanity, and a double-headed walk-in tiled shower. This home offers both luxury and convenience. The updated kitchen is an ideal space, with granite countertops, stainless steel appliances, a stylish tile backsplash, and 2015 KraftMaid cabinetry in a stunning navy blue. Every room is thoughtfully painted and wallpapered, adding character to the gleaming hardwood floors and plush, high-quality carpets throughout. The home also boasts an updated HVAC system and a brand new asphalt driveway. The finished basement includes a rec room and ample storage space, while the expansive 0.8-acre lot overlooks serene pastoral farmland, with a beautiful hardscaped patio perfect for outdoor entertaining. Best of all, this home is located under 1.5 miles from the heart of downtown Chestertown, so youâre just minutes away from shopping, dining, and all the charm the town has to offer.
Adorable and Affordable in Chester Harbor community! This 4-bedroom 2 bath home is ready for you! situated on a .8-acre level lot that backs to trees and open fields, this home offers a private retreat in a sought-after Water oriented community. There is a large Country Kitchen with room for table and chairs. Laundry in Kitchen is convenient and easy to access. Main level has two bedrooms and 2 baths while the finished lower level offers plenty of space and 2 bedrooms. Come and enjoy the tranquil and walkable neighborhood that is close to Chestertown and offers Queen Annes County Schools!
ONLINE AUCTION: Bidding begins 11/19/2024 @ 10:00 AM. Bidding ends 11/21/2024 @ 11:30 AM. List Price is Suggested Opening Bid. Lot of land in Tolchester Beach, Maryland located within Kent County. Nearby attractions include Tolchester Marina and +/- 7 miles to all the attractions in Rock Hall, Maryland. Easy Access to Major Traffic Artery Rock Hall Road. Deposit: $5,000.
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!
This beloved waterfront property has been a treasured family gathering place for over twenty four years. There have been numerous updates throughout that time, including the spectacular shoreline area which offers a private dock with about 5 feet MLW, bulk-headed shoreline, several boat lifts, water slide and sandy beach. From the homesite, you can walk down the well constructed stairs or you can take a golf cart down the convenient ramp area beside the steps. This home was designed for entertaining family and friends inside and out with an outdoor covered deck, expansive lawn and amazing sunset views. The large updated Gourmet kitchen opens into a spacious dining and sitting area overlooking the water and adjoins a media/entertainment room. There are 5 bedrooms, a large laundry and storage room, recent BAT upgraded septic system, and an oversized double plus garage. This location affords you protected water on Fairlee Creek for your boat but easy access to the Chesapeake Bay. With membership in GOCA, the volunteer Civic association, for $100 per year the Marina has graciously granted certain privileges that have been enjoyed by the membership, dating back to the 1980's. They include access to the marina grounds and facilities, swimming pool, golf course, boat ramp, and beaches. There is no other community like Great Oak!
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.
Welcome home this beautiful end unit townhome in the newer community of The Village At Chestertown. This 3 bedroom, 2.5 bath townhome looks out over the beautiful pond with fountain, and a great walking path around the pond and community. Furry friends are welcome at the nearby dog park as well. This home is less than a year old and has had some upgrades added since the purchase, such as the maintenance free fully fenced back yard, ceiling fans, upgraded light fixtures, upgraded bathroom vanities, kitchen faucet, hardware, and more! Easy commute to Rt. 301, and the brand new YMCA is right around the corner! Enjoy Chestertown with it's small town charm, great restaurants, artistic venues, and close to Washington College. Schedule your tour today!
Almost new home in Chestertown! Modern three bed, two bath rancher with split floor plan. Open kitchen living space features LVP flooring, kitchen island, stainless steel appliances, and large windows with lots of sunlight streaming in! Come check it out today!
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. Under Contract, but taking back up offers.
Great opportunity to own in the College Heights subdivision across from Washington College. A few improvements would make this rancher a cozy home. One level living offers a living room, kitchen, 3 bedrooms and 1 bathroom. 2 enclosed porches present additional living space for an office, family room or game room. The exterior is brick with a newer roof. The home is situated on a large, level lot, partially fenced. A $175 fee will be charged to the buyers agent at settlement. Escrow money should be 1% of the sale price or a minimum of $2,000. All offers are to be submitted online directly to prop offers. Lock box is located on the side door. Please make sure the home is locked when leaving.
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.
Great investment property, currently rented with long term tenants. Located in town with schools nearby. Being sold as is, needs some tlc.
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.
**Seller has purchased a new dishwasher and it will be installed in the coming days. 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!
Located in a desirable community, this charming 3-bedroom, 1-bath home offers the perfect blend of comfort, convenience, and style. Situated on a generous lot, the property provides ample outdoor space for relaxation or entertaining, making it ideal for families or anyone who enjoys the outdoors. As you step inside, you'll be welcomed by a spacious living room featuring vaulted ceilings that create an open, airy atmosphere. The cozy fireplace adds warmth and charm, making it the perfect spot to gather during cooler evenings. The updated kitchen is a true highlight, offering modern appliances, stylish finishes, and plenty of counter space to prepare meals with ease. Whether you're hosting friends or enjoying a quiet meal at home, this kitchen is both functional and inviting. Outside, the paved driveway provides ample parking, with space for multiple vehicles. The home's exterior complements its inviting interior, creating excellent curb appeal. This home is perfect for first-time buyers, downsizers, or anyone looking for a cozy retreat within a welcoming community. Schedule your showing today!