The median home value in Chestertown,
MD is $240,000.
the county median home value of $207,500.
The national median home value is $266,648.
The average price of homes sold in Chestertown,
MD is $240,000.
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.
Move in ready & low maintenance home all within town limits! Well maintained end unit with 3 beds, 1 1/2 baths has an open kitchen/dining with a covered porch to enjoy the great outdoors. Central air/heat make this home extra comfortable. Located on a dead end street just a few minutes away from Downtown Chestertown and the many public boat ramps, restaurant's, marinas & shopping!
"Langford Creek Farm" As Exquisite as Rare, this unique offering boasts 790+/- Total Acres with over 4 Miles of Western Facing Shoreline, 7ft+/- mlw, over 500 acres of Mature Forest, 150 +/- tillable acres, a Large 3 bedroom Historic Farm House, a 2nd Waterfront Home Site, Several Large Ponds and 2 Large Barns. This Magnificent Farm boasts the Oldest Second Growth Forest on the Eastern Shore and is the culmination of 13 total contiguous parcels. Amazing deer and waterfowl hunting await you at this Pristine Nature Sanctuary.
Charming country home minutes from downtown Chestertown! Located in the desirable Quaker Neck area and nearly 4.5 acres, it is only 1.5 miles from Quaker Neck Landing and the Chester River. The previous structure was torn down and it was fully renovated with a new well, BAT septic system and foam insulation in 2013. Talkie internet and Direct TV hooked up. New carpets in all bedrooms. HVAC â central air/heat. 9ft ceilings on first floor, granite counter tops in kitchen and bathrooms, walk-in pantry, woodstove in grand living room with vaulted ceilings, oak floors, oversized master suite on 2nd floor with walk-in closet. A bonus room used as a guest room/office/den. French doors to screen porch overlooking gorgeous brick patio and landscaping. Electric inground dog fence. Large 2-bay garage with workshop area and lots of storage space. Electric is hooked up. Water-line in place to be hooked up. This is a must see!
Gorgeous and rare 5 bedroom, 3 bath brick rancher in walking distance of historic downtown Chestertown. Large windows bring tons of natural light to every room. Fully fenced, large backyard includes a fantastic in-ground swimming pool surrounded by lush landscaping. Large Florida room just off the pool deck makes this home an entertainerâs delight. Updated baths, including a recently added full bath on the lower level. Tax record is incorrect. This home actually includes almost 3500 finished square feet. Oversized 2 car side entry garage and large paved driveway provides ample parking. Beautiful eat-in kitchen with a large number of cabinets and counter space. Welcome Home! Pictures are from the prior listing. House in same condition but now with a 5th bedroom and 3rd full bath! 5k credit being offered.
PENTRIDGE WOODS FARM, in an unspoiled corner of MarylandÃ¢ÂÂs Eastern Shore, could be a weekend refugeÃ¢ÂÂor your forever family home. On almost 170 private acres, with a modern and comfortable main house and a contemporary guest cottage down the road, this low-maintenance property has tilled fields, two ponds, and a dense forest. Pentridge Lane neighbors are a friendly community of mostly waterfront homes. Nearby Chestertown offers cultural and athletic events at Washington College, golf and sailing at the informal country club, a renowned farmers market on Saturdays, live music and theatre venues, a hospital, good schools, coffee shops and restaurants, and a thriving arts community. The area has long been a major sailing and cycling destination and is rapidly becoming an equestrian center. While Kent County fiercely preserves its agricultural heritage, it is less than a two-hour drive from Washington, Baltimore or Philadelphia and not much farther from the NYC area. The main house, designed by a Yale Architecture School grad as a modern farmhouse with a full basement, has four bedrooms, 2 ÃÂ½ baths, a large detached garage, and an interior courtyard garden. The center of the soaring open-plan main floor is a massive double-sided Finnish soapstone fireplace that divides the kitchen from the sitting area, with French doors opening onto the deck and brick courtyard. This floor also has a dining room/library, two bedrooms and a study/fourth bedroom. The second floor consists of a huge media room or studio and a large en-suite master bedroom. The distinctive two-story guesthouse (a short drive or ten minute walk from the main house) has a large deck and windows that wrap around the corners of the cube-shaped building. The guesthouse is currently a rental property but could easily revert to the owner's personal use. About eighty acres are farmed under a shared profit/loss arrangement by a local farmer (qualifying the owner for agricultural property tax benefits). The forest is prime deer-hunting terrain, also generating revenue. Because strict Kent County zoning laws protect agricultural land and the Chesapeake Bay watershed, this farm can never be subdivided and the deed also designates the woods as an avian refuge. As a result, the farm is home to resident and migratory birds, an oversupply of deer, as well as foxes, rabbits and other small animals. Weekend residents can enjoy all the farm offers with hardly any work, as the farming and garden maintenance are now done by trusted local people. But Pentridge Woods Farm would welcome more active participation by engaged owners, who might want to add an organic vegetable garden, experiment with different market crops, build a stable and keep horses, or establish their own vineyard. The possibilities are endless. Note: the listing agentÃ¢ÂÂs website has an aerial video and more info/photos. PLEASE NOTE; All Buyer agents MUST attend all showings and inspections before and after Contract. All appointments must to requested by AGENT, not clients.
Formerly used as a house of worship, this property is zoned Village which could allow for many different uses including a residence. The building is almost 2000 sq. ft. with a large open room and raised stage with a ramp. There are no stairs or pews. There are men's and women's restrooms with double vanities and the other rooms that could be bedrooms or kitchen. The parking lot is located in the rear. It is situated on 1.9 acres, backs to the trees and the views from the front are farm fields. There are many possible uses for the property including, but not limited too, single family dwelling, offices, retail, restaurant, personal service establishment and many more. Some uses are subject to a site plan review.
Coventry Farms Rancher! Enjoy one level living in the 3 bedroom 2 bath rancher with attached garage, and rear screened in porch. This home is close to the waterfront college town of Chestertown, with shops, and restaurants a short drive away. This is a Fannie Mae home. Submit all offers on Homepath site.
Nice rancher with three bedrooms, 1.5 bathrooms, nice living room , kitchen, family room. and CAC/Heat. Affordably priced and just needs some TLC from you to turn this into a wonderful home. This property cannot be purchased with any type of government financing due to the condition of the roof on the detached garage.
Completely renovated 1,280 sq ft 3BR Townhome in the heart of historic Chestertown on residential street with little traffic. Well maintained home has been completely updated. All new high quality plush carpet in all bedrooms. Modern durable plank vinyl flooring brightens the first floor living area. Kitchen has been completely remodeled with gorgeous granite counters, spacious white cabinets and all new appliances. Townhome has both living room and family room areas. Upstairs bathroom has also been updated with all new fixtures and finished tile. Family room opens to private fenced backyard and back patio. Home is within walking distance of local shopping area.
Updated two bedroom, one bath townhome that shows great! There is a community sports court on the common areas, a small playground area, high speed internet is available at a discount if you sign up prior to your settlement. These properties are updated beautifully, and very low maintenance. The new metal roof ensures you won't be replacing it for a good long time! There is a washer/dryer, full size, microwave, refrigerator, and stove. Plenty of countertop space and cabinetry. This is the nicest property at this price in our county! Come see it. There are only six townhomes left!
Location, location, location! Wonderfully maintained one story brick rancher. Flexible floor plan allows for in-home office, primary bedroom with views of the water, fireplace, jacuzzi, skylights. Hardwood floors throughout and a brick floor screened porch with water views. This property has the best of both worlds, in town living and water views! A must see!
The Chester River is just across the open space of Wilmer Park, from this townhome! The living room, with vaulted ceiling, fireplace and sky lights, is bright and roomy. Relax on the rear deck, tend to your flowers in the tidy garden or sit in your rocker on the front porch and watch people as they enjoy Wilmer Park. Gleaming wood floors are throughout the main level. There is a main level bedroom and full bath on main level. There is a den area on 2nd level that would make a great office or open up the wall and have sitting room off of the bedroom, as it was originally designed. Easy stroll to the Chester River and the Chestertown Marina. This is a great place to hang your hat part time or full time.
*NEW CONSTRUCTION* To be built. Lot cleared and ready! Quiet and peaceful Eastern Shore living. 4 Bedroom 2 Full baths. Wonderful price in this competitive market to get what you want. You choose siding, shingles, cabinets, flooring and more. Very open floor plan with the entry, living room, dinning room and kitchen. Lot conveniently located to all the major routes, only minutes away from Downtown Chestertown and Centreville. A short easy commute to Middletown, Dover, Annapolis, DC, and the beaches. Located in QA County school district. Lot size not accurate. A bit over .5
Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your private dock and sandy beach. Exposed beams, scalamandre wallpaper, and multiple fireplaces. First floor owners suite featuring private laundry area, walk-in closet, gas fireplace and remodeled bath with soaking tub. Second floor owner's suite with additional laundry area and remodeled bath. Breezeway to the garage. House has had major remodels in 2000 and 2020. Town sewer. Not far from town but the property has a private feel. Come and be amazed!! All buyers must be pre-approved.
Photos are of model home. Lot is cleared, and footers are being put in. Your very own chance to own new construction, at a great price. Open kitchen, dining, and living area. 4 bedrooms, 2 full baths. Front, side, and back door. Very clean layout. Kitchen appliances included, wonderful laundry area. The sooner you act, the more options of specifications you may choose. Located 45 minutes from the bay bridge, in a rural area. Quiet and peaceful living! . A short easy commute to Middletown, Dover, Annapolis, DC, and the beautiful beaches. Located in QA County School District. Minutes away from downtown Chestertown and Centreville.
Don't miss your chance to own in Great Oak Landing. Make this summer a new beginning by the Bay. Play a round on the 9-hole executive golf course or enjoy the summer heat at the pool. Ask friends to join you for a drink at The Landing Restaurant or Jellyfish Joel's Beach Bar before heading to the sandy beach for a sunset bonfire. This is the the Eastern Shore Bay life at its best, just 20 minutes from historic Chestertown and 1.5 hours from Philadelphia. Access to amenities is optional HOA. Spacious colonial with wrap around porch and all the southern charm you need. Large living room with brick fireplace and eat in kitchen with Corian Counters. Off the kitchen there's a sunroom and a separate screened porch for afternoons in. First floor also features a formal dining room, laundry room and full bath. Upstairs you'll find 2 bedrooms, a large hall bath and the master suite with private bathroom and walk in closet. The property also has a 2 car garage with extra 3rd bay perfect for storage or a hobby room.
Take a look at this beautiful model home located in Tolchester Village! One of 23 available duplexes and townhouses that have been completely remodeled!! Featuring a terrific galley kitchen with all major appliances, nice living room/dining room combination with a slider to the patio. Bedrooms have vaulted ceilings! Tolchester Village is a community with completely updated 3 bedroom and 2 bedroom units to choose from. The three bedroom units are priced at $129,900 and the two bedroom units are priced at $119,900. Thoughtfully remodeled and they show great! Common areas include a playground!!! For qualified buyers your mortgage payment could be $900+/- per month. There is HOA fee of $40.00 per month, and all units are served by public water and sewer. Affordable, beautiful, and low maintenance!! What could be better?
A blank canvas with strong bones... The home was taken down to the studs, beams stabilized, windows restored, Spanish Cedar front door, restored staircase restored... ENTER AT YOUR OWN RISK, INDEMNIFICATION AGREEMENT MUST BE SIGNED PRIOR TO ENTRY.
Updated home.. fenced back yard with a storage shed, zoned heat pumps. There is a patio and a third floor deck overlooking the semi private back yard. Brand new carpet throughout. Tiled floors in kitchen and Florida room, and fresh paint, inside and out. This home is adorable, just a couple of blocks from the wonderful historic Chestertown Shopping Area, and Washington College. One of the rooms upstairs has "cut outs" overlooking the stairway and owner will close those off to make another bedroom if desired. Shows well, no fridge or stove at present.
Presenting "Honest Point Farm" - Embrace the finest of Eastern Shore Living, Serenity and Nature at Honest Point Farm. Three Waterfront homes in Chestertown's Estate area all situated on 26 acres. This rare property consists of a beautifully maintained and updated main estate residence with breathtaking views and two charming guest homes- Winter Cottage and Summer Cottage. The main residence boasts 5 bedrooms (4 en-suite) a recently added expansive gourmet kitchen, renovated bathrooms, refinished hardwood floors, generator, 3 new heat pumps and a recently refinished waterside gunite pool. The guest homes each boast 2 bedrooms and one bath, perfect for company or as rentals. Ideally located, each dwelling has its own privacy and gorgeous views. Grounds also include an orchard, garden, wooded area, dock, in ground pool, barn, pond, various outbuildings with approximately 20 acres of woods. Given the acreage and all the fabulous amenities, this property is an exceptional offering! **Property Video in Virtual Tours**
A real restoration opportunity on Water St. This Victorian is a project for someone who has a love of old houses.It needs attention. This house has a Mansard roof is covered in pressed tin. Hardwood floors throughout and high ceilings. Crown moldings, chair- railings built-ins and fireplaces. There is a total of 5 bedrooms and 3.5 baths. Wide covered porch in the front. Screened porch in the rear. 2 car garage and driveway for off street parking. Heat is not functioning, needs a new roof(part is covered with a tarp). Partial central air. Some views of the river over the 18th century houses from the second and third floors. This house has great potential and is a rare find for Water St. It is waiting to be restored to its former glory. Property is being sold in as-is condition; some restoration plans available.
Solid investment property. Property is currently leased for a year through 5/15/2021. Rental market is strong because of close proximity to College and downtown. Fenced in rear yard allows privacy and shed has ample storage for yard accessories. If your are looking to add to your investment portfolio, take a look as this has positive cash flow. 24 hours showing notice required because house is tenant occupied. Lister must accompany. There is no sign on property.
Welcome to the historic John . Stam house, the only "A-rated" Victorian in Chestertown according to the Secretary of the Interior. This property has so much to offer. A Gothic Revival Victorian with painted fire places, a double parlor with pocket doors, and entrance hall. Features such as hand painted plastered ceilings, Jenny doors, and original medallions, make this a one of a kind home. Dado chair rail and paneling, Bradbury and Bradbury Art Wallpapers, Soapstone fireplaces, China closet, and the list goes on. The details are such that the property really needs to be seen to be appreciated. Kitchen is completely upgraded with Delohghi stove and sub zero refrigerator. Waterfall in the back yard with gracious gardens make for a charming outdoor oasis. "Carriage slate "architectural shingle roof. Currently run as a bed and breakfast. Additional buildable lot at the rear of the property included in the sale which makes the total property approximately 1.3 acres. . Driveway with 6-8 parking spaces makes hosting guests easy.
Beautiful, well maintained 3 bedroom end unit townhome. Just minutes from downtown Chestertown. Features freshly refinished hardwood floors, new carpet, new roof, vaulted master bedroom, soaking tub and separate shower in the master bath, 9 foot ceilings on the first floor, walk out second story deck, and an over-sized garage with a workshop. The home is very close to shopping and restaurants. A perfect place for weekends or year-round lifestyle living.
This downtown Chestertown house with good bones is priced right for an updated renovation. Surprisingly quiet for Maple Avenue. Currently a single residence but could be a two unit building. Nice sized rear yard. Short walk to Chester River and downtown Chestertown.