The median home value in Chestertown, MD is $225,000.
the county median home value of $183,500.
The national median home value is $185,800.
The average price of homes sold in Chestertown, MD is $225,000.
Approximately 41.87% of Chestertown homes are owned,
compared to 42.32% rented, while
15.82% 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!
Learn more about Chestertown Real Estate.
Pride of ownership is evident the moment you walk through the door! The living room opens up to the dining area in the kitchen. The hall bath offers double sink & the master bath has easy step in shower. Owner has added some crown moldings & a rear deck that overlooks the backyard where deer & turkey visit periodically. Located near the end of the street so there is little traffic that passes by!
Custom Chesapeake Bay View Cape constructed in 2000, features main level master suite w/luxury master bath, Florida room off of the living room, spacious kitchen with breakfast nook, separate dining room and full basement. The lush landscape consists of fig trees and persimmon, grape arbor, and more! Just around the corner from The Shanty at Tolchester Marina.
Nice one story home Located in a great neighborhood, featuring 3 split bedrooms, large updated eat in kitchen with SS appliances, fireplace, living and dining room with wainscoting and stenciled lower walls, updated bath, seasonal blooming perennial flowers, and shaded screened in porch
One of Chestertown's most prestigious addresses. Located on the river halfway between town and "The Club". 1.48 acres of privacy. Professionally maintained and landscaped. The house has had one addition and two remodels. Large open floor plan,pool, guest/in-law suite,golf, gazebo, boating all make for endless entertaining possibilities.
Updated & clean, this saltbox style home was remodeled in 2014 with wood floors, new kitchen & baths, & new carpet in the bedrooms. A newer heat pump & vinyl windows make this an efficient, affordable home to operate. There's plenty of space with 4 bedrooms, plus 2 full baths. A full basement provides storage space too. You''ll enjoy views of the farm across the street & relaxing on the rear deck
Bachelors Hope Farm, available for the first time in 50+years, is a once-in-a-lifetime waterfront & hunting farm. 9600 sq.ft., 7bed Main Home is situated within feet of the Chester River. 420' dock has 8' MLW, water & electric, w/ railway. 3000'+ of River frontage w/ 1400'+ revetment. 164+ acres: 96 tillable, 43 wooded & 3 ponds. 4bed Farm Home & barn. Exquisite & prestigious Quaker Neck locale.
Just like new!This 3 BD 2 BA in the water privilege community of Tolchester has new roof, new windows, new carpet, new appliances, fresh paint and more.Mature trees and back deck with built in bench provides great bird watching.The community beach and all the amenities the Tolchester Marina offers are both within walking distance.Perfect starter home, weekend get-away or those looking to downsize.
Walking distance from Historic Chestertown, this 4BR, 3.5BA, three-story waterfront end unit townhome in the secluded community of Chester River Landing faces Northeast towards the Chester River and brand new Washington College boathouse. Soaring 10' ceilings on the first floor maximize bright, airy views of the river enjoyed throughout an open floor plan, with gourmet kitchen, dining and living rooms, and decks all facing the water. Built for year-round living, the main floor design elements include 6' wainscoting, hardwood floors, gas fireplace, 3-story elevator, office/den, powder room, and generous closet space for gear. For those who love to cook, eat, chat, or just sit and look at the water, the custom kitchen with granite counter tops, custom cabinetry, GE Monogram appliances and wrap-around breakfast bar has something for everyone. From the kitchen and living room, a cozy outdoor deck leads to full dock for fishing, canoeing, kayaking or bird watching. Upstairs, the second floor offers two en suite bedrooms. First, an oversized master with full closets, own deck, and luxurious bath with double vanity, walk-in shower and whirlpool tub overlooking the river provides a quiet, comfy retreat. A full sized laundry closet with stacked washer/dryer, extra storage closet, and a second bedroom with full bath and queen bed complete this level. The third floor bunk room, which easily handles two sets of double-bunk beds and another queen bed, can sleep 10 comfortably. This room shares a full bath with another bedroom, currently used as a rec room with oversized, wrap-around couch and TV. In addition to ample living, sleeping, and storage space inside, this unit offers a separate garage and a deeded boat slip at the community dock (valued at 35,000. Common area amenities also include a fire pit with Adirondack chairs, grilling area and pool. Less than a mile from the home, Historic Chestertown offers great dining, shopping, farmers markets, and of course, Washington College. Easily accessible from Philadelphia, Wilmington, Washington D.C., Baltimore and Annapolis, this home provides weekend or year-round convenience, comfort, and amenities on Maryland's beautiful Eastern Shore. Owner would be interested in selling this home furnished-please inquire. So many more community amenities available - Waterpark, crabbing and fishing pier etc. See Covell Communities Chester River Landing website for more.
3-story waterfront end unit T/H in secluded community & walking distance to Historic Chestertown was built for year-round living. Open floor plan with bright, airy views of the river, elevator, hardwoods, custom kitchen and more. Outdoor deck leads to full dock with a deeded boat slip. Many community amenities available-waterpark, crabbing & fishing pier. Please inquire for full list.
Beautifully maintained, spacious rancher in Country Club Estates. Nearly 3900 square feet, boasting 4 bedrooms, 3 baths, a private entrance in-law suite, hardwood and ceramic tile floors, granite gourmet kitchen and screened porch. Minutes from historic Chestertown and within walking distance of Chester River Yacht & Country Club.
House completely remodeled in 2014: new roof, insulated windows, heating and air conditioning, plumbing, insulation, and electrical. New kitchen with custom cherry cabinets and stainless steel appliances. Underlying commercial zoning allows a variety of uses. Detached block building (28X30) with potential for business and/or apartment.
3Bedroom 2 Bath on end lot of rural subdivision convenient to Chestertown and Rt. 301 Hardwood flooring, vaulted ceilings, Deck and Sunroom overlooking built in saltwater pool Stainless appliances, HVAC,and pool filtering equipment all updated in the last 2 yrs
GREAT NEW BUILD! OPEN DESIGN W/ LARGE KIT & LIVING AREA. $4500 UPGRADED FLOORING & STAINLESS KITCHEN PACKAGE SEP. LAUNDRY/UTILITY ROOM. SPLIT BEDROOM DESIGN. SIMILAR MODEL CAN BE VIEWED AT 913 ROUND TOP RD. NEW MODEL WILL NOT HAVE SIDE DOOR BUT WILL HAVE STEPS FROM SLIDER. EXTERIOR COLOR MAY VARY. END OF YEAR DELIVERY. BUYER PAYS ALL REC & TRANSFER. MHBR #3717. PICS ARE OF PREVIOUS HOME
Beautiful home in excellent condition with plenty of living and entertaining space. Low maintenance exterior, hardwood and carpet floors, granite counters, large master bedroom with full bath and walk in closet, office, family room, living room, breakfast nook and separate dining room. Full finished basement with a game room, full bath, crafts/hobby room, lounge, large built in bar and storage.
Good clean listing. This home has been updated along the way and well cared for. It is a must see listing if your in the market for something that is all finished and ready to move into. Not a handyman need on this one. It's already been done for you.The pictures give a good idea but come see in person. Great place to call home.
Spectacular waterfront home located on the Chester River! Enjoy the beautiful sunset right from the family room! 2 large decks with screened in porch, large dock, new kitchen, new cork floors, upgrades throughout, detached 1 garage with unfinished space above. Master on main level, waterfront view from each bedroom!! Come and get this beautiful retreat!
Hurry to this Unique Opportunity!! Over 21 Acres Ready for your Horses & Existing Vineyard- Entertainer's Delight- Nearly 5600 sq ft, 5 Bedrooms, 3.5 Baths. In-Ground Pool, Large Patio. Fenced Pasture. Large Outbuilding with 2 Stalls, Main-Level Master Suite w/ ADDITIONAL Potential In-Law Bedroom/Rec Room w/ Access to 1/2 Bath & Washer/Dryer, 3- Car Side-Load Garage,. 3 LARGE upper-level Bedrooms!
Built in 1735 and completely restored in 1977, the Buck-Bacchus House is rich with history and detail. Situated one block off the Chester River this house features hardwood floors, original fixtures and lots of character! The living room boasts a large wood burning fireplace with a Tuscan grill. The cellar is complete with heating & air and a workshop. One of Chestertowns most distinguished homes!
A diamond in the rough! Older farmhouse on quiet street 15 minutes outside of Chestertown and within minutes from Chesapeake Bay, marinas/restaurants. House is in need of major repairs, or possibly tear down and build the home of your dreams. Public water/sewer is a big plus! Whether you are looking for a little fixer-upper or you're a seasoned investor, this would be a great spot to call home
First floor has been completely updated with a new bath, new kitchen, new flooring, fresh paint. Super cute one bedroom chalet with an outdoor shower, a one car garage, but two bays, and one is a workshop area. Stack washer/dryer, and water conditioner located in workshop area on main level. Very cute home, slider to outside as well. Limited peek of water & access thru private beach. .
Recently renovated home in Chestertown. Enjoy your morning coffee in a charming breakfast room, with tons of natural light or grab your favorite book from one of the built-ins. Quick walk to nearby restaurants, easy commuter location, perfect starter home. Ask your agent how to get a $10,000.00 credit towards your purchase!
An upgraded colonial home on revitalized Cannon Street. This home features hardwood floors throughout, upgraded kitchen and baths, vaulted ceilings, central HVAC, first floor powder room, and a Tulikivi pizza oven! Outside is a custom two story workshop with electric, gardens, and fenced backyard. Property also has rear alley access. A must see to appreciate! Offered below the appraised value.
This is it!! Fabulous Custom-Built Home to the highest standards boasting a modern open floorplan, Chef's Designer kitchen including, What! - 3 Ovens!!, Outer Banks inspired wall of glass in family room w/FP, 5367 sf + 2500 sf basement & woodstove, 20x22 screened porch, second floor balcony overlooking FR & kit, gleaming hardwood flrs, Awesome home for entertaining perched on over 13 acres-Hurry!
The peaceful setting & glorious garden of this post and beam reflect the civilized pace of the Eastern Shore while modern conveniences & quality details let you enjoy the rustic setting w comfortable ease. The cathedral ceiling gives a lodge feel to the LR & the brick FP ensure a cozy backdrop for every cool or snowy day. A kitchen renovation added shaker style cabinets and granite counters.
Located in an exclusive water-oriented community, this magnificent home offers an open plan design for those who enjoy entertaining and being active. The prominent eye-catching architectural style of the interior accents a classic paint scheme throughout. Various seating spaces, lavish main level master suite, large kitchen, sunroom, bonus room, 4 zones, 3-bay garage, deeded boat slip with 4' MLW