The median home value in Chestertown,
MD is $257,000.
the county median home value of $192,000.
The national median home value is $231,815.
The average price of homes sold in Chestertown,
MD is $257,000.
Approximately 43% of
Chestertown homes are owned,
compared to 42% rented, while
15% are vacant.
Chestertown real estate listings include condos, townhomes, and single family homes
Commercial properties are also available.
If you like to see a property, contact Chestertown real estate agent to arrange a tour
Learn more about living in Chestertown.
Coveted private waterfront home!! Walk into Chestertown, yet have all of the privacy as if you were miles away. Chestertown, founded in 1706, is a quaint town filled with arts, entertainment, fine restaurants, shops, old inns and home to one of the best farmer's market in MD. You can walk to the parades, Chestertown Tea Party Festival and summer concerts along the brick paved walkways and enjoy the water views and boats coming in. This home sits at the end of a culdesac on a very quiet street. Watch the sunrise and the moon reflect on the water. This home was dubbed "moon river" retreat . Over 1.6 acres and just shy of 3,000 sq ft. This rancher is waiting for an update . Wooden floors and huge glass doors looking over the river will make you fall in love. A built in pool and a yard to hold family gatherings, weddings, and a place to make incredible memories awaits you. Don't delay if you want this piece of paradise because it will be gone in a flash. Check out the approx. floor plan here https://youriguide.com/8_byford_ct_chestertown_md/doc/floorplan_imperial.pdf
Coming Soon! Victorian style house located the historic district of Colonial Chestertown. Random width flooring. Details like crown molding and chair railing, high ceilings and slate fireplaces. Lovely patio. Detached garage and driveway. New roof in 2019. 1 1/2 blocks to Chester River.
Eastern Shore Waterfront Retreat. Inviting home is set on the banks of Rosin Creek in the quiet community of Royston Shores in Queen Anne~s County, Maryland. The stunning stone fireplace anchors the open living spaces evoking a casual cottage ambiance with lovely water views throughout. The first floor master suite opens to the screened porch and water views of Rosin Creek. The dock offers 3-~~ MLW and boat enthusiasts can head out Rosin Creek right to the Chester River with numerous waterways to explore. Downtown historic Chestertown, home to Washington College, is just a 10-minute drive across the Chester River bridge. Enjoy visiting shops and cafes and taking a stroll down to the Chester River Walk, waterfront dining and Wilmer Park. Located about 90-minutes from Philadelphia and Washington, D.C.
Charming historic home featuring high ceilings, hardwood on every floor, covered front porch, formal dining or sitting room with pocket doors, detailed trim and so much more! Recently replaced hot water heater, electrical panel and HVAC systemic . This property is zoned Residential/Business (RB) and can be used as a single family home or as professional offices. Located one block from the Chester River waterfront. Seller Assistance considered. 1 parking space behind rear porch and numerous street spaces directly in front of the home.
This waterfront condo has the wow factor! As you enter your eye is drawn to the the Chester River. The living area is cozy with a gas fireplace. Fabulous kitchen with two islands features a Verona 5 burner gas stove, GE Profile appliances incl a wine fridge, Diamond self closing cabinets and two pantry cabinets. The dining area is at the front and has two built ins. Gleaming wide plank pine floors are found throughout the condo. The 2nd floor has two master suites. The 3rd floor has a large open space as well as a bedroom with full bath. Porches on all three levels for outdoor entertaining or a place to relax and enjoy your morning coffee. Other features include spray foam insulation, Noritz tankless water heater, Lutron Connect for 1st floor lighting and Water Cop. This beautifully finished condo was completed in 2017 by local builder Alden Yetman. Experience the joy of small town living on the Eastern Shore. Walk to the shops, parks and restaurants of Chestertown from this in town location.
BRAND NEW CONSTRUCTION 3 BR Cape Cod in quiet, waterfront community of Chesapeake Landing located just off Worton Creek in beautiful, historic Chestertown. A short drive to the restaurants and shops of Rock Hall on the Chesapeake Bay. Excellent area schools, parks and community center. 1st level Master BR with full bath. Upstairs, 2 BR and full bath. Large, eat in kitchen. Living Room. Separate front room for dining, office or family room needs. Back patio is perfect for entertaining. Community is water access with 2 marinas, boat slips and docks. A perfect location to keep your boat for a weekend away on the beautiful Eastern Shore or to make this your permanent home.
"Walnut Point Farm" ~ Exquisite 300+ Acre Waterfront Farm with over a mile of Shoreline is the perfect Eastern Shore Retreat! The Estate offers a 7,500+/- Main House with indoor and outdoor pools, Pier with Grand Boathouse and lift with 7ft+/- MLW, Large 3 bedroom Historic Guest House, Waterfront Caretakers Home, Large Barn for all farming equipment, Covered Bridge with many other outbuildings and blinds plus a few waterfowl ponds. This Estate is perfect for those looking for and escape from the hustle and bustle of the metropolitan lifestyle that would like to take in all that nature offers with a plethora of high end amenities. Please See Truplace Interactive Tour For more Photos and Floorplan at https://mls.TruPlace.com/property/406/84311/
3D Tour: https://unbranded.youriguide.com/165_char_nor_manor_blvd_chestertown_mdWelcome to 165 Char Nor Manor Blvd on the QA County side of Chestertown!!! Looking for water views that are basically water front??? This is the ONE!!! Unobstructed Chester River views without the waterfront price tag!!! Enjoy the peace and serenity that this property has to offer. This is a one of a kind property. Situated at the end of the waterfront street, this home is boasting over 2200 sq ft with an attached 2 car garage. No neighbors to your right and nothing behind you but water!!! When you enter this home you will notice that the entire home has been freshly painted, brand new carpet installed, new tile floor installed, and is ready for you to call it home! Entering the foyer you have a nice tile floor that leads to GORGEOUS hardwood floors through out the main level of the home. The Family Room is to the left and is open to the kitchen, giving this home an open, airy feel. The family room is large with an abundance of windows bringing in all the natural light and nature this property offers and it boasts a wood burning fireplace! From the family room you have 2 wide open entrances into the MASSIVE kitchen. The kitchen is gorgeous and offers water views that no other home has to offer!!! The kitchen offers you a large island with bar seating and pendant lighting, and abundance of countertop space and cabinet space, gorgeous hardwood floors, stainless steel appliances, an eat in table area, and the VIEWS are amazing!!! New tiles have also been installed in front of the sliding glass door leading to the deck. Finishing off the main level is the updated half bathroom, massive laundry room, which has plenty of room for storage also, and the entrance to the 2 car garage!!! Moving upstairs you will find 4 freshly painted LARGE bedrooms with great closet space. and brand new carpet throughout the entire second level. There is a bonus room off of the 4th bedroom that could be a possible 5th bedroom, playroom, office, etc. Endless possibilities with the bonus room!! Moving down the hallway you will find an updated, large full bathroom for the bedrooms boasting tile floors, fresh paint, and updated fixtures. Moving into the Master Suite!! AHHH peace and relaxation in this room!! Large bedroom with vaulted ceilings, fresh paint, new carpet, and it's own balcony so you can soak up those water views EVERY SINGLE MORNING!!! Wake up to the sounds of nature and water!!! Moving into the master bathroom you will find upgraded tile floors, upgraded fixtures, a HUGE Master Closet, a separate shower and 2 windows bringing in all the natural sunlight with water views. This master suite is one of a kind!!! You won't see these views anywhere else!!! Moving outback, you will find a freshly painted deck all overlooking the backyard, water, and nature. These views, this setting, you can't and won't find anywhere else!!! Privacy and water for a fraction of the price!!! The home is a convenient location to all major routes, only minutes to Downtown Chestertown, minutes to Centreville, short easy commute to Middletown, Dover, Annapolis, DC, the Beaches. AND you get the all the benefits from QA County and the QA County Schools!!! Put this home on your list today so you don't miss out on an almost waterfront property without the price tag!!!
Lovely Victorian with many original details. Beautiful wood floors, fireplace, updated kitchen and baths, new carpet in master bedroom and fresh paint throughout. Third floor bedroom could be home office. The porches and patio provide nice outdoor living space.Located in Chestertown's Historic District it is within walking distance to Washington College, shopping, restaurants and the Chester River.
Premium materials and finishes, including yellow pine floors reclaimed from Camden Yards, really set this waterfront cape apart. Crown moulding, wainscoting, panel doors, fireplace, sun room and master on first floor are among the many amenities. Studio or home office with AC/Heat is surrounded by a Williamsburg Garden and a gazebo sits waterside. Very private. Adjacent .44 perc approved lot can be purchased separately. Walk to C-town.
Completely renovated & move-in ready! This home is just minutes from Downtown Chestertown, located in the desirable Quaker Neck area. With upgrades JUST finished... your new home is BRAND NEW! Stainless steel appliances, granite countertops, upgraded flooring, tiled bathrooms, and a master with en suite bath. All in a lovely setting with fresh landscaping. Can't ask for much more... snag it soon!
NEW CONSTRUTION UNDERWAY. 1 ACRE LOT BACKS TO FARM LAND. 3 BEDROOM 2 BATH RANCHER WITH CATHEDRAL CEILING IN FAMILY ROOM. UPGRADED FLOOR AND STAINLESS STEEL KITCHEN APPLINACES. KITCHEN ISLAND WITH ROOM TO EAT AT. GRANITE COUNTER TOP IN KITCHEN AND ON ISLAND. STOP OUT AND TAKE A LOOK. OPEN FLOOR PLAN. YOU COULD PICK OUT THE COLORS AND MAKE THIS ONE YOUR OWN.
Buyer's situation changed, but their loss is your gain! This property checks all the boxes! Updated home offering a well appointed kitchen with Shaker wood cabinetry, stainless steel appliances, luxury vinyl plank flooring, and a large kitchen island. The open floor plan connects the kitchen and dining areas to the huge living room with beautiful hardwood floors and a wood burning fireplace. The refinished hardwood floors continue down the hall and into each of the three bedrooms. The master suite includes a stunning bathroom offering a subway tiled open shower with marble floor, double vanity with quartz counters, and tiled floors. A full, unfinished basement adds additional storage and usable space. With a fantastic location, convenient to Downtown Chestertown, a private, partially wooded lot backing to trees, and no HOA, this beautiful home is move-in ready!
Very well maintained and updated, this home on Lovely Lane is a must see. There is a new BAT system, new well , new windows and an encapsulated crawl space. The kitchen and bathrooms are updated, there is a tankless hot water system, hard wood floors throughout and a new family room addition. The detached garage has room for a shop, loads of storage space upstairs and another room for an office or game room. There is plenty of room for your boat or RV. Close to Chestertown, shops, restaurants and Washington College and the drive down Broad Neck is beautiful. Ready to move right in!
Unique and charming home within walking distance of downtown Chestertown and the river! Lovingly restored in 2013, the home features hardwood floors throughout, fresh paint in many rooms, a spacious screened porch and two master suites. The second floor features a spacious bedroom with a walk-in closet, a separate dressing room & laundry area next to the full bath with double vanity. The third floor features a cozy suite with bedroom, sitting area, and another full bath! From the screened porch, walk down the garden path to the incredible two story garden house. This is a rare find that can be whatever you want it to be: art studio, office, or guest quarters! Come see this wonderful home and all it has to offer!
Offered AS-IS and is eligible under the Freddie Mac First initiative through 4/24/2020- owner-occupant buyers and qualified non-profits. Investor offers are eligible for review after 20 days of the listing date. Brand new roof but house needs attention cash or 203k loans only.
This is a rehab project, with lots of space to work with. Four bedrooms, 2 baths, kitchen, separate dining room, living room, converted 2 car garage as a rec room. Sellers put on a porch addition, but needs work. Subject to a short sale with third party approval from the mortgagor. Well & Septic . The back yard has a deck area.
Great home! Master bath updated in 2020 and kitchen was completely updated in 2016. Both are beautiful!! Wood burning fireplace in the family room, overlooking a great back yard! There is a deck, a play ground area, a privacy fence makes this even more of an oasis. There is a fire pit, grilling area, you are all set! Inside, the wood floors on the first floor, an built ins are terrific. You have an updated kitchen in 2016 with stainless steel appliances to cook in! Upstairs is a huge master suite, and three additional bedrooms. There is a study nook in the hallway, Bathrooms total 2.5, and the garage is side face entry. Come check out this home. There is NO HOA and no front footage fee. This home is in the original section of Coventry farms. Encapsulated crawl space 2010
Construction Complete, Move Right In! Quality built Cape Cod on over ONE ACRE wooded yard. Three bedrooms and two bathrooms with bonus bedroom/den/office or nursery. Stainless steel appliances, recessed lighting, 2X6 walls, York high efficiency heat pump system. Extra storage in eves. Nice deck overlooking stream and environmentally protected area. Mature trees, creates privacy from the road. 2 miles from Chestertown and close to Rt 213 for easy commuting. Owner/Agent. Immediate occupancy!
Very well maintained home with an open floor plan that is perfect for entertaining. Sun room off the kitchen and rear deck overlook woods and nicely landscaped yard. Wood floors, fireplace in the living room, master bedroom on the main level and huge partially finished basement are just a few of the amenities. Located in Coventry Farm you are just minutes from Chestertown's historic district, shopping, restaurants and Washington College.
Impeccably maintained charming home with a water view of the Chester River. First floor open floor plan is perfect for entertaining. Living room with fireplace flows into a gourmet kitchen and right into the dinning area. Beautifully restored staircase takes you to a landing with bookcases and three bedrooms with two baths. The full basement with interior and exterior access is dry and great for storage. Property is nicely landscaped with a brick patio in back and fencing. Most furniture and the contents are negotiable so this can be a turnkey property. Want to escape the city and enjoy small town living? Come visit this lovely home and all it has to offer. If you can't visit, a virtual tour will be coming soon.
Location, Location, Location! Historic downtown home situated literally in the heart of everything Chestertown has to offer....one block from the Chester River and newly renovated Chestertown Marina, one block from all the shops and restaurants, and one block from Wilmer Park! Property is well appointed for an older home with potential first floor master, 3 further bedrooms and full bath on 2nd floor and 2 further potential bedrooms on 3rd floor. Recently painted inside and out with newer roof and updated gourmet kitchen including stainless appliances, induction cook top and wall oven. The perfect low maintenance garden with raised planting beds, fire pit and entertaining area. Fenced in back yard with shed and much sought after off street parking. What more could you ask for!
TO BE BUILT - List price reflects the lot & lot development with the Haydn model. There are many other floor plans and upgrades available with Caruso Homes, however there is no builder tie-in. All on two parcels totaling approximately 1.81 Acres on a quiet street among well-kept homes and manicured lawns. The second parcel is located on Elm St which allows access from the front or back of the property. This property also includes a paid sewer allocation! Just steps from the Tolchester Marina & The Shanty and only a quick drive to Rock Hall or Chestertown.
New Listing ~ The Cuff House ~ an impeccably restored historic home with modern amenities and substantial upgrades located on Cannon Street in Chestertown with water views from the front porch and a short distance to downtown. This period home dates to the mid 1700~s and has seen a remarkable transformation over two renovations preserving its architectural significance while providing the comforts and convenience of modern living. Turnkey in every aspect and finished to the highest standard, this property is sure to please the discerning buyer. Two bedrooms and two- and one-half baths are in the main residence along with a two-car garage and loft apartment found across a beautifully appointed brick courtyard. Off-street access and parking, irrigation, radiant patio heat for snow and ice control, Lutron lighting system and many more innovative features set this home apart from the crowd. Contiguous unimproved parcels available separately. Call for more information and to schedule a tour by appointment only.Historic Reference from Maryland Historic Trust Document K-545 dated 5.14.02 ~ The Thomas Cuff House~The Cuff House was probably built by the mid-eighteenth century, a dating supported by Kent County Wills and Land Records for that site, remaining interior woodwork, and an archeological survey. The house was restored in 1987. On the exterior deteriorated circular-sawn siding was replaced by new beaded siding corresponding to old siding fragments found under the eaves. The deteriorated tin roof was replaced with a wood shingle roof similar to several shingles found under old flashing around the chimney. The house as restored is a simple frame, two-story structure, with a central doorway, flanked on each side by 6/6 windows. Two similar windows are on the second story front and three on each gable, one on each floor. The door and window frames have a simple ovolo backhand molding. The rear of the house, invisible from the street, is a modern frame wing with similar windows and siding. The original interior plan of the front four rooms, up and down, remains. There are two rooms on each floor, each with a fireplace built into the large central chimney. The partitions between the rooms are vertical beaded board paneling, probably original to the house. The upstairs room on the right retained all the original woodwork, window and door frames with simple molding, simple mantel with shelf, and exposed beaded corner posts. The room below also retained an early mantel - a shelf supported on a simple molding and flat pilasters between the opening surround and the bottom of the shelf. The original stairway had been built around the corner of this room but had been removed. A fragment of the railing - simple with a beaded edge along the bottom - was found during the archeological exploration. The left-hand rooms had lost in a fire all original wood trim except the paneling. Locally found K-545 replacement mantels from the late 18th or early 19th century have been installed, as well as corresponding period corner cupboards in each of the first-floor rooms. One original door remained, with four raised panels, cross-pieces mortised together and fastened with wooden pegs and the shadow of HL hinges. Other doors were reproduced to match it. In the course of re-building the unstable rear wing, the remains of a brick pavement were found back of the first-floor room on the right side. This was left exposed, with shattered bricks replaced. The new rear wing has a three-story hall with staircase rising against four walls from first floor to third, where the attic is lighted by a 616 window at each end. A large new room was built across the back, trimmed with an early Federal style fireplace (from a demolished late 18th century house near Kenton, Delaware), flanking bookcases with keystone arches, and jib doors leading to a screened/glassed-in porch.~